ChatGPT Ads Agency Selection: 10 Questions to Ask Before Hiring in 2026

The inbox notification arrives at 9:47 AM: "We need to be on ChatGPT ads—yesterday." Your CEO forwards the OpenAI announcement. Your CMO schedules an emergency strategy call. Your board wants projections by Friday. Welcome to January 2026, where the advertising landscape just fractured again, and everyone's scrambling to figure out how conversational AI advertising actually works. The problem? There are maybe two dozen agencies worldwide who genuinely understand this space, and hundreds claiming expertise they don't have. The gold rush has begun, and the snake oil salesmen arrived first.

Choosing the wrong ChatGPT ads agency isn't just an expensive mistake—it's a strategic setback that could cost you six months of first-mover advantage while your competitors establish dominance in conversational search. The agencies pitching you today fall into three categories: the genuine pioneers who've been preparing for this moment since 2024, the traditional PPC shops hastily rebranding their Google Ads services, and the outright frauds who couldn't explain the difference between a conversational query and a keyword if their survival depended on it. This article gives you the ten questions that separate expertise from expensive theater.

Unlike traditional agency selection where you're comparing execution quality on established platforms, hiring for ChatGPT ads means evaluating strategic vision for a medium that's still defining itself. The agencies who succeed here won't be the ones with the biggest client rosters or the fanciest case studies—they'll be the ones who understand that conversational AI advertising requires completely different mental models than search advertising, display advertising, or social advertising. They'll be the strategists who recognized months ago that "keywords" are dead and "contextual intent signals" are everything. Let's identify them.

Question 1: How Long Have You Been Preparing for Conversational AI Advertising?

The official ChatGPT ads program launched testing on January 16, 2026, but the agencies worth hiring saw this coming years ago. The question isn't whether they have clients running ChatGPT ads today—almost nobody does yet, since the program is in limited beta—but whether they've been actively researching, theorizing, and building frameworks for conversational advertising since at least mid-2024. The best answer you can hear is something like: "We've been running experimental campaigns on conversational AI platforms since early 2025, testing different approaches to intent recognition and response-based targeting."

Look for agencies that can show you their preparation timeline. Did they publish thought leadership about conversational advertising before it was profitable to do so? Have they been attending AI conferences, participating in OpenAI developer forums, or conducting internal training sessions on large language model behavior? The fundamental architecture of large language models differs radically from traditional search algorithms, and agencies that understand these differences have been studying them for months, not days.

Red flags emerge when agencies claim they "pivoted quickly" after the January announcement. Conversational advertising isn't a pivot—it's a completely new discipline that requires deep understanding of natural language processing, contextual inference, and conversation flow dynamics. An agency that started learning about this three weeks ago cannot possibly compete with one that's been building expertise for eighteen months. Ask them directly: "Show me the earliest internal document, blog post, or strategy memo you created about conversational AI advertising." If they can't produce something dated before December 2025, you're talking to opportunists, not pioneers.

The truly sophisticated agencies will discuss their experiments with conversational interfaces across multiple platforms. They'll mention testing advertising approaches on Google's Gemini platform, exploring sponsored responses in AI-powered search experiences, and even running informal tests to understand how users interact with AI-generated recommendations. They'll speak fluently about the differences between interruption-based advertising (traditional display) and integration-based advertising (conversational AI). They'll reference academic research on human-AI interaction patterns and explain how those patterns influence advertising effectiveness.

This question also reveals the agency's resource allocation priorities. Preparing for a new advertising medium before it's profitable requires investment—in training, research, tool development, and strategic planning. Agencies that made those investments demonstrate vision and confidence in their ability to master emerging platforms. Agencies that didn't make those investments demonstrate they're reactive rather than proactive, which means they'll always be six months behind the curve. In a space evolving this rapidly, six months behind might as well be six years.

Question 2: What's Your Philosophy on Contextual Targeting Versus Keyword Targeting?

This question separates the agencies who understand conversational AI from those who are trying to force traditional search advertising frameworks onto a fundamentally different medium. ChatGPT ads don't work like Google Ads. There are no keyword auctions. There are no search terms reports. There are no exact match, phrase match, or broad match modifiers. Instead, ads appear based on conversational context—the entire flow of the dialogue, the user's apparent intent, the semantic meaning of their queries, and the AI's interpretation of what would be genuinely helpful at that specific moment in that specific conversation.

The right answer to this question involves the agency explaining why keyword thinking is obsolete in conversational advertising. They should articulate that when someone asks ChatGPT "I'm planning a two-week trip to Japan in April with my elderly parents—what should I know about accessibility?" they're not searching for keywords like "Japan travel" or "accessible tourism." They're having a conversation with an intelligent system that understands context, nuance, intent, and constraint. An ad that appears in that moment needs to respond to the entire contextual situation, not just surface-level keywords.

Expert agencies will discuss natural language processing techniques and how they inform targeting strategies. They'll explain that conversational AI advertising requires understanding semantic relationships, entity recognition, sentiment analysis, and intent classification. They'll describe how they map client offerings not to keywords but to "conversational scenarios"—specific types of discussions where the client's product or service would genuinely add value to the user's inquiry. They'll show you frameworks for identifying these scenarios and strategies for positioning ads that feel like natural extensions of the conversation rather than intrusive interruptions.

Watch for agencies that keep trying to translate everything back to search advertising analogies. If they say "it's basically like Google Ads but in a chat interface," run away immediately. That statement reveals fundamental misunderstanding. Conversational advertising is not search advertising in a different wrapper—it's an entirely new medium with its own rules, dynamics, and success metrics. The agencies who succeed here will be those who can think natively in conversational context, not those who keep trying to retrofit twenty-year-old search advertising playbooks onto a medium that doesn't work that way.

Ask them to walk through a specific example: "If our company sells ergonomic office furniture, what conversational scenarios would you target, and why?" The sophisticated answer won't mention keywords like "office chair" or "standing desk." Instead, it will describe conversations about remote work setup, back pain solutions, productivity optimization, or home office design—scenarios where furniture recommendations would emerge naturally from the discussion. They'll explain how they'd craft ad messaging that responds to the specific concerns raised in each conversational context, not generic product pitches that could appear anywhere.

Question 3: How Do You Measure ROI When Traditional Attribution Breaks Down?

Traditional advertising attribution relies on clicks, impressions, and conversion tracking pixels. Conversational AI advertising operates in a fundamentally different environment where those metrics become muddy at best and meaningless at worst. When someone has a twenty-minute conversation with ChatGPT that mentions your brand three times, sees your ad twice in different contexts, and then visits your website four days later, how do you attribute that conversion? The agencies claiming they can simply apply traditional attribution models are lying to themselves and to you.

The best agencies acknowledge this complexity upfront and present sophisticated approaches to measurement that go beyond last-click attribution. They'll discuss "conversation influence tracking"—methods for understanding how brand mentions, ad appearances, and conversational context contribute to eventual conversions even when the path isn't linear. They'll explain how they use probabilistic attribution models, incrementality testing, and brand lift studies to understand campaign effectiveness when traditional tracking breaks down. They'll be honest about what they can measure precisely and what requires estimation and modeling.

Look for agencies that have developed proprietary frameworks for tracking conversational advertising performance. They might describe using unique UTM parameters that encode conversational context, implementing server-side tracking methods that don't rely on browser cookies, or conducting regular brand awareness surveys to measure lift among ChatGPT users versus control groups. They'll discuss the importance of tracking assisted conversions, view-through conversions, and conversation-influenced conversions—not just direct response metrics that capture only a fraction of the value.

The sophisticated agencies will also explain how they establish baseline performance metrics before launching campaigns, so they can measure incremental impact. They'll describe methodologies for A/B testing conversational ad strategies, running holdout groups to understand organic versus paid influence, and using causal inference techniques to isolate advertising effects from other marketing activities. They'll acknowledge that measurement in conversational advertising is part science, part art, and entirely different from anything that came before.

Red flags appear when agencies promise "complete attribution" or claim they can "track every conversion." These promises are either dishonest or naive. Conversational advertising operates in a privacy-conscious environment where OpenAI doesn't share detailed user interaction data with advertisers. You'll get aggregated performance metrics, not individual user tracking. Agencies that promise traditional PPC-level tracking granularity either don't understand the platform's privacy constraints or are deliberately misleading you about what's possible. The honest agencies will explain the limitations, then show you how they work within those constraints to deliver meaningful performance insights.

Question 4: What's Your Approach to Creative Development for Conversational Contexts?

Creating effective ads for conversational AI requires completely different creative approaches than traditional advertising. Your ChatGPT ad isn't a banner, a video, or a sponsored post—it's a tinted text box that appears within an ongoing conversation, and it needs to feel like a natural, helpful contribution to that dialogue rather than an intrusive commercial message. The creative challenge is enormous: you need to be promotional enough to drive action but contextual enough to feel appropriate, brief enough to be digestible but informative enough to be valuable.

The best agencies will describe their creative development process in detail, emphasizing how they craft multiple ad variations for different conversational contexts. They should explain that a single product might require twenty or thirty different ad versions, each optimized for specific types of conversations. An ad for project management software appears differently in a conversation about remote team coordination than in a conversation about personal productivity or startup operations. The messaging, tone, and call-to-action need to adapt to the conversational context.

Ask them to show examples of how they structure conversational ad copy. Look for agencies that understand the importance of leading with value, not product features. In traditional search ads, you might lead with "50% Off Project Management Software!" In conversational advertising, that approach feels jarring and salesy. Instead, effective conversational ads might say something like "For remote team coordination, many companies are finding success with tools that integrate communication and task management..." followed by a specific mention of your product as an example worth exploring.

The sophisticated agencies will discuss their research into conversational user interfaces and how people respond to different messaging approaches in dialogue contexts. They'll explain their testing methodologies for determining which tone, length, and structure work best for different audience segments and conversational scenarios. They'll show you frameworks for balancing promotional content with genuine helpfulness—the core tension in conversational advertising. They'll describe how they collaborate with copywriters who understand dialogue writing, not just marketing copy.

Watch for agencies that show you traditional display ads or search ads as examples of their creative work. That's a massive red flag indicating they haven't actually developed conversational advertising creative yet. The creative requirements are so different that showing traditional advertising examples demonstrates they're still thinking in old paradigms. You want agencies showing you text-based, conversational ad examples that feel like natural dialogue contributions—even if those examples are from experimental campaigns or internal testing rather than live client work.

Question 5: How Do You Handle Brand Safety in AI-Generated Conversations?

Brand safety in conversational AI advertising presents challenges that don't exist in traditional advertising. When your ad appears next to a Google search result, you know the context—it's the search query. When your ad appears in the middle of a ChatGPT conversation, the context is an entire multi-turn dialogue that might have taken unexpected turns. What happens when your family-friendly brand's ad appears in a conversation that started innocuously but evolved into something controversial or inappropriate? This isn't theoretical—it's a genuine risk that requires sophisticated mitigation strategies.

The best agencies will explain their brand safety frameworks in detail, including both preventive measures and reactive protocols. They should discuss how they work with OpenAI's safety filters and category exclusions to prevent ad appearances in high-risk conversational contexts. They'll describe their processes for defining prohibited conversation topics, sensitive subject areas, and contextual red flags that should trigger ad suppression. They'll explain how they monitor campaign performance not just for clicks and conversions but for brand safety incidents and contextual appropriateness.

Look for agencies that have developed detailed brand safety guidelines specific to conversational advertising. These guidelines should go beyond traditional brand safety concerns (avoiding placement near violent or sexual content) to include conversational-specific risks like appearing in debates, controversial political discussions, or emotionally charged personal advice scenarios. The agency should show you their taxonomy of conversational contexts and explain which ones are appropriate for your brand and which ones require exclusion regardless of potential reach.

The sophisticated agencies will also discuss the philosophical tension in conversational advertising between reach and safety. Aggressive brand safety filters might eliminate 40% of potential ad placements, reducing campaign reach significantly. More permissive filters increase reach but elevate risk. The best agencies help you find the right balance for your brand's risk tolerance and reputation requirements. They'll present options, explain tradeoffs, and recommend strategies based on your industry, brand positioning, and competitive context.

Red flags emerge when agencies dismiss brand safety concerns or claim "the AI handles all that automatically." While OpenAI certainly implements safety measures, advertisers need additional brand-specific protections that go beyond platform defaults. Agencies that haven't thought deeply about brand safety in conversational contexts are agencies that will learn those lessons using your budget and your brand reputation as the testing ground. You want agencies who've already worked through these challenges, either through client work or through extensive pre-launch strategic planning.

Question 6: What's Your Relationship with OpenAI and Access to Beta Features?

The ChatGPT advertising program is still in early stages, with limited access and frequent feature updates. Your agency's relationship with OpenAI—and their access to beta features, early documentation, and direct support channels—can provide significant competitive advantages. Agencies with strong OpenAI relationships often get earlier access to new targeting options, measurement tools, and creative formats. They receive more responsive support when troubleshooting campaign issues. They get invited to advertiser summits where platform roadmaps are previewed months before public announcement.

Ask agencies directly about their OpenAI relationship status. Are they official beta partners? Do they have a dedicated OpenAI account representative? Have they been invited to advertiser advisory councils or early access programs? The answers reveal whether the agency is considered a strategic partner by the platform or just another advertiser with an API key. Strategic partners get better support, earlier feature access, and more direct influence on platform development—all of which translates to better campaign performance for their clients.

The best agencies will describe specific interactions with OpenAI that demonstrate partnership depth. They might mention participating in closed beta tests for new ad formats, providing feedback that influenced platform development, or attending invitation-only sessions where OpenAI executives preview upcoming features. They'll show you documentation proving their partner status and explain what that partnership means for your campaigns. They'll describe how they leverage their OpenAI relationships to solve client problems faster and more effectively than agencies without those relationships.

However, also watch for agencies that exaggerate their OpenAI connections. Some agencies claim "exclusive partnerships" that don't actually exist or imply special access they don't have. Verify their claims by asking specific questions: "Who's your OpenAI account manager?" "What beta features are you currently testing?" "When was your last meeting with OpenAI's advertising team?" Legitimate partners will answer these questions with specific names, features, and dates. Fraudulent claims will be vague and unverifiable.

Consider also that some excellent agencies might not have strong OpenAI relationships yet simply because they're newer to the space or smaller in size. What matters more than current partnership status is their plan for building that relationship and their track record of developing strategic partnerships with other advertising platforms. Agencies that have historically become Google Premier Partners or Facebook Marketing Partners demonstrate they know how to build platform relationships that benefit their clients. Those same relationship-building skills will serve them well with OpenAI.

Question 7: How Do You Approach Testing and Iteration in Such a New Medium?

Traditional PPC campaign management relies on decades of accumulated best practices, benchmark data, and proven strategies. Conversational AI advertising has none of that. Every campaign is essentially an experiment, and success requires agencies that are comfortable with ambiguity, rapid iteration, and learning from failure. The question isn't whether the agency will make mistakes—they will, because everyone will—but whether they have systematic approaches to learning from those mistakes and improving performance over time.

The best agencies will describe detailed testing frameworks that balance exploration with exploitation. They should explain how they allocate budget between proven strategies (even if "proven" just means "worked last week") and experimental approaches that might unlock breakthrough performance. They'll discuss their hypotheses development process—how they generate ideas for new targeting strategies, creative approaches, or bidding tactics to test. They'll show you documentation templates for recording test results, analyzing performance, and extracting learnable insights.

Look for agencies that think in terms of "learning velocity"—how quickly they can run experiments, gather meaningful data, and apply those learnings to improve campaign performance. In a rapidly evolving medium like conversational advertising, the agencies that learn fastest will dominate. Ask them how many distinct experiments they can run simultaneously, how they prioritize which tests to run first, and how they determine when they've gathered sufficient data to make confident decisions. The sophisticated agencies will have clear answers to all these questions, backed by methodologies adapted from statistical experimentation best practices.

The sophisticated agencies will also discuss their approach to documenting and sharing learnings. Since conversational advertising is so new, the agencies that systematically capture insights and build institutional knowledge will compound their expertise over time. Ask them: "How do you document campaign learnings?" "How do you share insights across clients?" "How do you train team members on emerging best practices?" You want agencies that are building knowledge repositories, not just running individual campaigns in isolation.

Red flags appear when agencies claim they "already know what works" or present rigid strategies without acknowledging uncertainty. In January 2026, nobody knows with certainty what works in ChatGPT advertising—the medium is too new and evolving too rapidly. Agencies claiming certainty are either lying or delusional. The honest agencies acknowledge uncertainty while presenting structured approaches to reducing it through systematic experimentation. They'll say things like "our hypothesis is X, and here's how we'll test it" rather than "we know X works because we've always done it that way."

Question 8: What Industries or Use Cases Do You Think Are Best Suited for ChatGPT Ads?

Not every business should be advertising on ChatGPT, at least not yet. Conversational AI advertising works brilliantly for some industries and use cases while delivering mediocre results for others. The best agencies have developed clear perspectives on where conversational advertising excels and where it struggles. They should be able to articulate not just why your business might succeed on the platform, but also which of your competitors might struggle and why. This strategic perspective—knowing where the medium works and where it doesn't—is what separates consultants from order-takers.

Expert agencies will typically identify several high-opportunity categories for conversational advertising. Software and SaaS companies often perform well because users frequently ask ChatGPT for tool recommendations and comparisons. Educational products and services benefit from the advice-seeking nature of many conversations. Complex products that require explanation rather than impulse purchase—financial services, B2B solutions, healthcare offerings—can use conversational ads to provide the detailed information users need. The agencies should explain the underlying reasons why these categories work, not just list industries randomly.

They should also identify categories that face challenges in conversational advertising. Low-consideration impulse purchases might not justify the cost of conversational ad placements. Highly regulated industries like pharmaceuticals might struggle with the lack of precise control over ad context and messaging. Local businesses with limited geographic reach might find the audience targeting too broad for efficient campaigns. The agencies willing to discuss where conversational advertising doesn't work demonstrate intellectual honesty and strategic sophistication—they're trying to help you succeed, not just sell services.

Ask them specifically about your industry and business model: "Given what you know about our company, why do you think we should or shouldn't be advertising on ChatGPT right now?" The best answer might actually be "you shouldn't—yet." An agency that tells you to wait six months until the platform develops better features for your specific use case, or until industry benchmarks emerge that justify the investment, is an agency that prioritizes your success over their revenue. That's the kind of partner you want.

The sophisticated agencies will also discuss timing and sequencing. They might recommend starting with small experimental budgets to test hypotheses before scaling, or focusing initially on specific product lines or audience segments where success seems most likely. They'll explain how they'd sequence campaign development, starting with highest-confidence opportunities and expanding into more speculative areas once they've established baseline performance. This strategic thinking about prioritization and sequencing demonstrates they're thinking about your success holistically, not just about launching campaigns quickly.

Question 9: How Do You Stay Current as the Platform Evolves Weekly?

ChatGPT advertising is evolving at unprecedented speed. New targeting options launch monthly. Creative specifications change based on user feedback. OpenAI releases new features, deprecates old ones, and modifies platform policies faster than most agencies can update their documentation. In this environment, staying current isn't a nice-to-have capability—it's a core competency that directly impacts campaign performance. An agency that's three weeks behind on platform updates is an agency that's missing opportunities and wasting your budget on obsolete strategies.

The best agencies will describe systematic approaches to monitoring platform evolution. They should explain who on their team is responsible for tracking OpenAI announcements, how frequently they review platform documentation, and what processes they use to rapidly implement new features in client campaigns. They might mention participating in OpenAI developer forums, subscribing to official update channels, attending platform webinars, or maintaining relationships with other agencies to share intelligence about platform changes.

Look for agencies that have formalized their learning and implementation processes. They might describe weekly platform update meetings where the team reviews changes and discusses implications for client campaigns. They might show you internal documentation systems where they track feature releases, performance changes, and emerging best practices. They might explain their rapid response protocols for implementing new features—how quickly they can test a new targeting option after it launches and roll it out to appropriate client campaigns if it proves effective.

The sophisticated agencies will also discuss their participation in broader AI and advertising communities. They'll mention attending relevant conferences, following AI researchers and advertising technologists on social media, reading academic papers about conversational interfaces and user behavior, and engaging with thought leaders who are shaping the future of AI advertising. They understand that staying current on ChatGPT advertising requires staying current on AI development generally, since platform evolution is driven by broader technological advances in large language models and conversational interfaces.

Red flags emerge when agencies can't articulate specific mechanisms for staying current. Vague answers like "we keep up with industry news" or "we read blogs" suggest they don't have systematic processes for platform monitoring. In a space evolving this rapidly, unsystematic approaches to staying current guarantee the agency will fall behind. You want agencies that treat platform monitoring and rapid learning as core operational capabilities, with dedicated resources and formal processes ensuring they're always working with the latest platform knowledge.

Question 10: Can You Explain Your Pricing Model and Why It's Structured That Way?

Pricing structures reveal an agency's fundamental business philosophy and their confidence in delivering value. For ChatGPT advertising—where performance benchmarks don't exist, best practices are still emerging, and campaign management requires significantly more strategic thinking than traditional PPC—pricing models vary wildly across agencies. Some charge traditional percentage-of-spend fees, which can create perverse incentives when the goal should be efficiency, not spending. Others charge flat monthly retainers that might not scale appropriately with campaign complexity. The best agencies have thought carefully about pricing models that align their success with yours.

Expert agencies will explain their pricing rationale in detail, connecting their fee structure to the specific value they deliver and the work required for ChatGPT advertising. They might argue for higher fees than traditional PPC management because conversational advertising requires more strategic input, creative development, and custom analysis. They should be able to break down where your money goes: what percentage covers platform management, what portion funds creative development, how much supports strategic consulting and performance analysis. This transparency demonstrates they've thought carefully about value delivery, not just set arbitrary prices.

Look for agencies willing to discuss pricing flexibility and performance incentives. The best arrangements often include base fees that cover essential management work plus performance bonuses tied to achieving specific outcomes. These performance incentives align agency success with client success—the agency makes more money when you make more money. Ask them: "What portion of your fee is at risk based on performance?" and "What metrics determine performance bonuses?" The answers reveal whether they're confident enough in their capabilities to put their compensation at risk.

The sophisticated agencies will also discuss pricing evolution as campaigns mature. They might propose higher initial fees during the learning phase when campaigns require intensive optimization and experimentation, with fees decreasing once best practices are established and campaigns run more efficiently. Or they might propose the opposite: lower initial fees during proof-of-concept testing with increases as campaigns scale and complexity grows. Either approach can be valid—what matters is that they've thought about how pricing should evolve with campaign maturity and can justify their approach.

Red flags appear when agencies can't clearly articulate their pricing rationale or when their pricing seems disconnected from the work required. If an agency charges the same percentage of spend for ChatGPT advertising as for Google Ads management, they're likely either overcharging for Google Ads or undercharging for ChatGPT advertising—because the work requirements are dramatically different. If they can't explain why their fees are higher or lower than competitors, they probably haven't thought strategically about pricing. You want agencies that can defend their pricing based on specific value delivered, not just market rates or historical precedent.

Why This Decision Matters More Than You Think

Choosing a ChatGPT ads agency isn't just selecting a vendor to manage another advertising channel—it's choosing a strategic partner who will shape how your brand participates in the biggest shift in digital marketing since social media. The decisions your agency makes in these early months will establish patterns, relationships, and positioning that compound over years. An agency that helps you establish thought leadership in conversational AI advertising creates advantages that persist long after campaigns launch. An agency that wastes six months pursuing ineffective strategies while your competitors learn and optimize puts you at a disadvantage that's difficult to overcome.

The strategic implications extend beyond advertising performance to broader business positioning. As conversational AI becomes the primary interface between consumers and information, brands that establish authoritative presence in these conversations gain structural advantages. They become the companies people think of first when they need solutions in your category. They build trust through repeated helpful appearances in valuable conversations. They gather insights about customer needs, concerns, and decision processes that inform product development, not just advertising. Your agency partner either helps you capture these strategic advantages or squanders the opportunity.

Consider also the talent implications of this decision. The best people in advertising want to work on cutting-edge challenges, not manage mature platforms with established playbooks. Hiring an agency that's genuinely pioneering conversational AI advertising gives you access to top-tier strategic talent who are attracted to the problem's complexity and novelty. Hiring an agency that's just rebranding their traditional PPC services gives you access to whoever they can staff on the account—likely not their best people, since the best people are working on the most interesting challenges.

The financial stakes are also higher than they appear. Industry observers suggest that conversational AI advertising will capture significant market share from traditional search advertising over the next three years. Early movers who establish effective campaigns now will ride that growth wave with steadily declining acquisition costs as they optimize. Late movers will enter a more competitive market with higher costs and more established competitors. The agency you choose now determines whether you're an early mover capturing growth opportunities or a late mover fighting for expensive scraps.

The Questions Behind the Questions: What They're Really Revealing

Each of these ten questions serves double duty—the surface question evaluates specific expertise, but the meta-question evaluates how the agency thinks, learns, and operates. When you ask about their preparation timeline, you're not just learning when they started studying conversational advertising—you're learning whether they're proactive or reactive, whether they invest in future capabilities or only respond to immediate market demands. When you ask about measurement approaches, you're learning whether they think rigorously about complex problems or prefer simple answers to complicated questions.

The best agencies reveal themselves not just through their answers but through how they engage with your questions. Do they welcome difficult questions or seem defensive? Do they acknowledge uncertainty or pretend to know everything? Do they ask clarifying questions to understand your specific situation or deliver generic presentations? Do they challenge your assumptions when appropriate or just agree with everything you say? These behavioral signals often matter more than the content of their responses, because they reveal the agency's culture, values, and operating philosophy.

Pay attention to whether agencies customize their responses to your specific business context or deliver the same pitch to everyone. The best agencies will ask detailed questions about your business model, competitive position, customer acquisition economics, and strategic objectives before proposing specific ChatGPT advertising approaches. They'll explain why certain strategies make sense for your situation and why others don't. They'll show you how they'd adapt their standard approaches to your unique requirements. This customization demonstrates they're thinking about your success specifically, not just selling a standard service package.

Also notice whether agencies educate or sell. The best agencies spend significant time teaching you about conversational AI advertising, explaining concepts, sharing frameworks, and helping you develop sophisticated understanding of the medium. They know that educated clients make better decisions, provide better feedback, and achieve better results. Agencies that rush through education to get to pricing and contracts are agencies that prefer uninformed clients who won't question their recommendations—not a dynamic that leads to exceptional outcomes.

Red Flags That Should End the Conversation Immediately

While the ten questions above help you identify excellent agencies, certain red flags should disqualify candidates immediately, regardless of their answers to other questions. If an agency guarantees specific performance outcomes in ChatGPT advertising, end the conversation. Nobody can guarantee performance in such a new medium with limited historical data and rapidly changing dynamics. Guarantees are either dishonest or backed by such conservative targets that they're meaningless. Ethical agencies discuss expected performance ranges based on assumptions while acknowledging uncertainty, not make promises they can't keep.

Similarly, if an agency claims they can "game the algorithm" or "hack ChatGPT's targeting," run away. These claims reveal fundamental misunderstanding of how AI systems work and demonstrate unethical approaches that will eventually backfire. Conversational AI advertising requires working with the platform's design, not against it. Agencies that think in terms of manipulation rather than optimization will waste your budget pursuing tactics that don't scale and might get your campaigns suspended when OpenAI's fraud detection systems catch them.

Watch for agencies that can't articulate clear differences between conversational advertising and traditional search advertising. If they keep saying "it's basically the same" or use Google Ads analogies for everything, they don't understand the medium well enough to manage campaigns effectively. The platforms are fundamentally different—different user behaviors, different intent signals, different measurement challenges, different creative requirements. Agencies that don't recognize these differences will keep trying to force square pegs into round holes until your budget runs out.

Be wary of agencies that criticize all other agencies or claim they're the only ones who truly understand ChatGPT advertising. The reality is that dozens of smart agencies are working hard to master this medium, and many are developing genuine expertise through different approaches. Agencies that position themselves as uniquely enlightened are usually covering for lack of substantive differentiation. The best agencies acknowledge that multiple valid approaches exist and explain why their particular approach fits your needs, not why everyone else is wrong.

Finally, distrust agencies that rush the decision process or pressure you to sign contracts quickly. They'll claim you need to "move fast before competitors gain advantage" or "lock in early adopter pricing before rates increase." These pressure tactics suggest the agency prioritizes closing deals over ensuring good fit. The best agencies want you to take time making informed decisions, talk to multiple candidates, and choose the partner that's genuinely right for your situation. They're confident enough in their capabilities to let you conduct proper due diligence rather than rushing you into commitments.

Building a Successful Agency Partnership Beyond the Selection Process

Choosing the right agency is crucial, but it's only the beginning of the relationship. The agencies that deliver exceptional results aren't just technically skilled—they're also effective collaborators who know how to work productively with clients. As you evaluate agencies, assess not just their ChatGPT advertising expertise but also their communication styles, reporting practices, and collaborative approaches. The most knowledgeable agency in the world won't help you if they can't effectively communicate insights or incorporate your feedback.

Discuss upfront how the agency approaches client collaboration. How frequently will you meet? What information will they need from you regularly? How do they handle strategy disagreements? What decision rights do they expect to have versus decisions that require your approval? The best agencies propose clear governance structures that balance their need for execution autonomy with your need for strategic control. They'll suggest regular strategy reviews where major decisions are discussed and debated, while delegating day-to-day tactical decisions to their team.

Ask about their reporting philosophy and what metrics they'll track. In conversational advertising where traditional metrics are less reliable, reporting becomes more complex and more important. You want agencies that provide context around numbers, explain performance trends, highlight learnings from experiments, and connect campaign metrics to business outcomes. Avoid agencies that dump spreadsheets of raw data without interpretation or those that cherry-pick metrics to make performance look better than it actually is. You need honest, insightful reporting that helps you understand what's working and why.

Consider also how the agency approaches knowledge transfer. The best partnerships involve teaching you about conversational advertising so your internal team develops expertise over time. Agencies confident in their ongoing value aren't threatened by client learning—they welcome it because educated clients provide better feedback and make better decisions. Agencies that hoard knowledge and keep clients dependent are agencies you'll eventually outgrow or resent. Look for partners who actively work to increase your team's sophistication, not those who prefer keeping you in the dark.

Frequently Asked Questions About Hiring ChatGPT Ads Agencies

How much should I expect to pay for ChatGPT ads management?

Pricing varies significantly based on campaign complexity, ad spend, and agency positioning. Most agencies charge either flat monthly retainers ranging from $3,000 to $15,000 for small-to-medium campaigns, or percentage-of-spend fees typically between 15-25% of ad spend. Given the strategic complexity and experimental nature of conversational advertising, expect to pay premium rates compared to traditional PPC management. Agencies charging significantly below market rates likely lack genuine expertise or will underinvest in your campaigns.

Should I hire a specialist ChatGPT ads agency or a full-service digital agency?

For now, specialist agencies with deep ChatGPT advertising focus generally deliver better results than full-service agencies dabbling in the space. Conversational advertising requires such different approaches from traditional channels that generalist agencies struggle to develop genuine expertise while managing multiple platforms. However, if you need integrated campaigns spanning multiple channels, look for full-service agencies that partner with ChatGPT specialists rather than claiming in-house expertise they don't yet have.

How long does it take to see results from ChatGPT advertising?

Initial performance signals emerge within 2-4 weeks as campaigns gather data and agencies complete initial optimizations. However, truly optimized performance typically requires 8-12 weeks as agencies test different approaches, identify winning strategies, and scale what works. Be suspicious of agencies promising immediate results—conversational advertising requires learning periods that can't be rushed. Set expectations for a 90-day optimization cycle before evaluating whether campaigns are succeeding.

Can I manage ChatGPT ads in-house instead of hiring an agency?

In-house management is possible if you have team members with time to develop expertise, appetite for experimentation, and comfort with ambiguity. However, most companies benefit from agency expertise during at least the first 6-12 months. Agencies working across multiple clients learn faster than any single company can and bring pattern recognition that accelerates your optimization. Consider starting with an agency and transitioning to in-house management once you've established baseline performance and developed internal capabilities.

What questions should I ask about data privacy and user information?

Ask agencies how they handle any user data they might access through campaign management, what data security protocols they follow, and how they ensure compliance with privacy regulations like GDPR and CCPA. Confirm they understand OpenAI's data usage policies and advertiser data restrictions. Reputable agencies will have clear data governance policies and be willing to sign data protection agreements. They should also explain what user information you will and won't receive from ChatGPT advertising campaigns.

How do I know if an agency is actually getting results or just spending my money?

Establish clear success metrics upfront that connect to business outcomes, not just vanity metrics. Insist on regular reporting that shows not just impressions and clicks but conversions, cost per acquisition, customer lifetime value, and return on ad spend. Ask for transparency into optimization actions—what experiments they're running, what they're learning, how they're applying those learnings. Request access to the advertising dashboard so you can verify their reports. Strong agencies welcome accountability and proactively demonstrate value.

Should I hire an agency that also offers traditional PPC services or a ChatGPT-only specialist?

Both models can work depending on your needs. Agencies offering both traditional PPC and ChatGPT advertising can help you optimize budget allocation across channels and develop integrated strategies. However, ensure their ChatGPT team is distinct and sufficiently staffed—not just their Google Ads team learning on the side. ChatGPT-only specialists often have deeper expertise but may lack perspective on how conversational advertising fits into broader paid media strategies. Evaluate based on the specific expertise of the people who'll work on your account.

What's a reasonable test budget for initial ChatGPT advertising campaigns?

Most agencies recommend initial test budgets between $5,000 and $25,000 per month for at least three months. This provides sufficient data to test multiple targeting approaches, creative variations, and bidding strategies while drawing meaningful conclusions. Smaller budgets risk insufficient data for optimization decisions. Larger initial budgets risk overspending before learning what works. Start conservative, establish baseline performance, then scale budget as you identify winning strategies that justify increased investment.

How do I evaluate an agency's creative capabilities for conversational ads?

Ask to see examples of conversational ad copy they've created, even if from test campaigns or theoretical exercises. Evaluate whether the copy feels natural and helpful rather than salesy and promotional. Ask about their creative development process, how many variations they typically test, and how they adapt messaging to different conversational contexts. Strong agencies have copywriters who understand dialogue writing and can create ads that enhance rather than interrupt conversations. Request sample campaigns for your specific business to assess their ability to understand your value proposition.

What should I do if campaign performance is disappointing after three months?

First, ensure you had realistic expectations given the experimental nature of conversational advertising. Review whether the agency conducted systematic testing, documented learnings, and applied insights to optimization. If they can show clear learning progression and reasonable optimization actions, consider extending the test period—some strategies take longer to prove out. If they can't demonstrate systematic learning or if their approach seems haphazard, it may be time to find a new agency. Conversational advertising is difficult, but good agencies show clear progress even when absolute performance is still building.

Can ChatGPT advertising work for local businesses with limited geographic reach?

Geographic targeting in ChatGPT advertising is still evolving, making local campaigns challenging in early 2026. However, for businesses in major metropolitan areas or those serving specific regions, conversational advertising can work if targeting strategies focus on local intent signals beyond just geography. Discuss with agencies whether they can target conversational contexts that indicate local intent—people discussing moving to your area, asking about local services, or mentioning nearby landmarks. Local success requires creative targeting approaches until platform geo-targeting capabilities mature.

How important is industry experience when selecting a ChatGPT ads agency?

Industry experience matters less for ChatGPT advertising than for mature channels because best practices are still emerging across all industries. An agency with deep expertise in conversational advertising mechanics can likely succeed in your industry even without prior category experience. However, agencies with relevant industry knowledge can ramp faster and bring valuable perspective on competitive dynamics, customer psychology, and effective messaging. Prioritize conversational advertising expertise first, industry experience second—but the combination of both is ideal when available.

Making Your Decision: A Framework for Final Selection

After conducting interviews and evaluating multiple agencies against these ten questions, you'll likely have several qualified candidates. Making the final selection requires weighing multiple factors—expertise, cost, cultural fit, capacity, and strategic vision. Create a structured evaluation framework that scores agencies across the dimensions most important to your situation. Don't rely on gut feeling alone, but also don't ignore it entirely—your instinctive sense of which agency "gets it" and which ones are performing often proves accurate.

Consider conducting a paid pilot project with your top two or three candidates before committing to long-term contracts. A four-week strategy development engagement where each agency creates detailed ChatGPT advertising plans for your business reveals far more about their capabilities than any interview process. You'll see how they think, how they work, and what level of strategic sophistication they bring. The investment in multiple strategy projects pays for itself by dramatically reducing the risk of selecting the wrong long-term partner.

Don't underestimate the importance of team chemistry and communication compatibility. You'll be working closely with this agency during a period of rapid learning and frequent strategy adjustments. Agencies that communicate in ways that match your preferences, respond to feedback constructively, and engage collaboratively rather than defensively will deliver better outcomes than slightly more expert agencies that are difficult to work with. The best technical expertise in the world doesn't help if you dread every meeting and communication breaks down under pressure.

Finally, trust your assessment of the agency's learning velocity and adaptability. In such a rapidly evolving medium, the agency that's best today might not be best in six months if they can't keep pace with platform evolution. Choose agencies that demonstrate systematic learning approaches, intellectual curiosity, and comfort with ambiguity. These qualities predict success in dynamic environments better than current expertise alone. You want partners who will evolve with the platform, not ones who'll be obsolete by the time they finally master the current state.

Conclusion: The Strategic Advantage of Choosing Well

The agency selection decision you make in early 2026 will echo through your marketing strategy for years. Choose well, and you'll establish dominant position in conversational AI advertising while competitors are still figuring out whether to participate. You'll build institutional knowledge, capture early-mover advantages, and develop sophisticated capabilities that compound over time. Choose poorly, and you'll waste six months and significant budget learning lessons you could have avoided while competitors pull ahead. The stakes justify investing serious time and energy in this decision.

The ten questions presented here aren't just an interview script—they're a framework for understanding what genuine expertise in conversational AI advertising looks like. Agencies that answer these questions well demonstrate they've thought deeply about the strategic, technical, and operational challenges of this new medium. They've invested in building capabilities before it was profitable to do so. They've developed sophisticated perspectives on what works and why. They're prepared to be true strategic partners, not just vendors executing your instructions.

Remember that you're not just hiring advertising management services—you're choosing a partner who will help you navigate one of the most significant shifts in digital marketing history. The rise of conversational AI as the primary interface between consumers and information fundamentally changes how brands build awareness, establish authority, and drive consideration. Your agency partner either helps you capitalize on this shift or becomes another expense line while competitors capture the opportunity. Make the choice that sets you up for long-term strategic advantage, not just short-term campaign execution.

As you move forward with agency selection, revisit these questions regularly. The right answers will evolve as the platform matures and industry best practices emerge. An agency that gives excellent answers today should give even better answers six months from now as they accumulate experience and insights. Regular reassessment ensures your agency partner continues delivering value as both your needs and the platform itself evolve. The goal isn't finding perfection today—it's finding a partner committed to pursuing excellence over time as you build conversational advertising capabilities together.

The inbox notification arrives at 9:47 AM: "We need to be on ChatGPT ads—yesterday." Your CEO forwards the OpenAI announcement. Your CMO schedules an emergency strategy call. Your board wants projections by Friday. Welcome to January 2026, where the advertising landscape just fractured again, and everyone's scrambling to figure out how conversational AI advertising actually works. The problem? There are maybe two dozen agencies worldwide who genuinely understand this space, and hundreds claiming expertise they don't have. The gold rush has begun, and the snake oil salesmen arrived first.

Choosing the wrong ChatGPT ads agency isn't just an expensive mistake—it's a strategic setback that could cost you six months of first-mover advantage while your competitors establish dominance in conversational search. The agencies pitching you today fall into three categories: the genuine pioneers who've been preparing for this moment since 2024, the traditional PPC shops hastily rebranding their Google Ads services, and the outright frauds who couldn't explain the difference between a conversational query and a keyword if their survival depended on it. This article gives you the ten questions that separate expertise from expensive theater.

Unlike traditional agency selection where you're comparing execution quality on established platforms, hiring for ChatGPT ads means evaluating strategic vision for a medium that's still defining itself. The agencies who succeed here won't be the ones with the biggest client rosters or the fanciest case studies—they'll be the ones who understand that conversational AI advertising requires completely different mental models than search advertising, display advertising, or social advertising. They'll be the strategists who recognized months ago that "keywords" are dead and "contextual intent signals" are everything. Let's identify them.

Question 1: How Long Have You Been Preparing for Conversational AI Advertising?

The official ChatGPT ads program launched testing on January 16, 2026, but the agencies worth hiring saw this coming years ago. The question isn't whether they have clients running ChatGPT ads today—almost nobody does yet, since the program is in limited beta—but whether they've been actively researching, theorizing, and building frameworks for conversational advertising since at least mid-2024. The best answer you can hear is something like: "We've been running experimental campaigns on conversational AI platforms since early 2025, testing different approaches to intent recognition and response-based targeting."

Look for agencies that can show you their preparation timeline. Did they publish thought leadership about conversational advertising before it was profitable to do so? Have they been attending AI conferences, participating in OpenAI developer forums, or conducting internal training sessions on large language model behavior? The fundamental architecture of large language models differs radically from traditional search algorithms, and agencies that understand these differences have been studying them for months, not days.

Red flags emerge when agencies claim they "pivoted quickly" after the January announcement. Conversational advertising isn't a pivot—it's a completely new discipline that requires deep understanding of natural language processing, contextual inference, and conversation flow dynamics. An agency that started learning about this three weeks ago cannot possibly compete with one that's been building expertise for eighteen months. Ask them directly: "Show me the earliest internal document, blog post, or strategy memo you created about conversational AI advertising." If they can't produce something dated before December 2025, you're talking to opportunists, not pioneers.

The truly sophisticated agencies will discuss their experiments with conversational interfaces across multiple platforms. They'll mention testing advertising approaches on Google's Gemini platform, exploring sponsored responses in AI-powered search experiences, and even running informal tests to understand how users interact with AI-generated recommendations. They'll speak fluently about the differences between interruption-based advertising (traditional display) and integration-based advertising (conversational AI). They'll reference academic research on human-AI interaction patterns and explain how those patterns influence advertising effectiveness.

This question also reveals the agency's resource allocation priorities. Preparing for a new advertising medium before it's profitable requires investment—in training, research, tool development, and strategic planning. Agencies that made those investments demonstrate vision and confidence in their ability to master emerging platforms. Agencies that didn't make those investments demonstrate they're reactive rather than proactive, which means they'll always be six months behind the curve. In a space evolving this rapidly, six months behind might as well be six years.

Question 2: What's Your Philosophy on Contextual Targeting Versus Keyword Targeting?

This question separates the agencies who understand conversational AI from those who are trying to force traditional search advertising frameworks onto a fundamentally different medium. ChatGPT ads don't work like Google Ads. There are no keyword auctions. There are no search terms reports. There are no exact match, phrase match, or broad match modifiers. Instead, ads appear based on conversational context—the entire flow of the dialogue, the user's apparent intent, the semantic meaning of their queries, and the AI's interpretation of what would be genuinely helpful at that specific moment in that specific conversation.

The right answer to this question involves the agency explaining why keyword thinking is obsolete in conversational advertising. They should articulate that when someone asks ChatGPT "I'm planning a two-week trip to Japan in April with my elderly parents—what should I know about accessibility?" they're not searching for keywords like "Japan travel" or "accessible tourism." They're having a conversation with an intelligent system that understands context, nuance, intent, and constraint. An ad that appears in that moment needs to respond to the entire contextual situation, not just surface-level keywords.

Expert agencies will discuss natural language processing techniques and how they inform targeting strategies. They'll explain that conversational AI advertising requires understanding semantic relationships, entity recognition, sentiment analysis, and intent classification. They'll describe how they map client offerings not to keywords but to "conversational scenarios"—specific types of discussions where the client's product or service would genuinely add value to the user's inquiry. They'll show you frameworks for identifying these scenarios and strategies for positioning ads that feel like natural extensions of the conversation rather than intrusive interruptions.

Watch for agencies that keep trying to translate everything back to search advertising analogies. If they say "it's basically like Google Ads but in a chat interface," run away immediately. That statement reveals fundamental misunderstanding. Conversational advertising is not search advertising in a different wrapper—it's an entirely new medium with its own rules, dynamics, and success metrics. The agencies who succeed here will be those who can think natively in conversational context, not those who keep trying to retrofit twenty-year-old search advertising playbooks onto a medium that doesn't work that way.

Ask them to walk through a specific example: "If our company sells ergonomic office furniture, what conversational scenarios would you target, and why?" The sophisticated answer won't mention keywords like "office chair" or "standing desk." Instead, it will describe conversations about remote work setup, back pain solutions, productivity optimization, or home office design—scenarios where furniture recommendations would emerge naturally from the discussion. They'll explain how they'd craft ad messaging that responds to the specific concerns raised in each conversational context, not generic product pitches that could appear anywhere.

Question 3: How Do You Measure ROI When Traditional Attribution Breaks Down?

Traditional advertising attribution relies on clicks, impressions, and conversion tracking pixels. Conversational AI advertising operates in a fundamentally different environment where those metrics become muddy at best and meaningless at worst. When someone has a twenty-minute conversation with ChatGPT that mentions your brand three times, sees your ad twice in different contexts, and then visits your website four days later, how do you attribute that conversion? The agencies claiming they can simply apply traditional attribution models are lying to themselves and to you.

The best agencies acknowledge this complexity upfront and present sophisticated approaches to measurement that go beyond last-click attribution. They'll discuss "conversation influence tracking"—methods for understanding how brand mentions, ad appearances, and conversational context contribute to eventual conversions even when the path isn't linear. They'll explain how they use probabilistic attribution models, incrementality testing, and brand lift studies to understand campaign effectiveness when traditional tracking breaks down. They'll be honest about what they can measure precisely and what requires estimation and modeling.

Look for agencies that have developed proprietary frameworks for tracking conversational advertising performance. They might describe using unique UTM parameters that encode conversational context, implementing server-side tracking methods that don't rely on browser cookies, or conducting regular brand awareness surveys to measure lift among ChatGPT users versus control groups. They'll discuss the importance of tracking assisted conversions, view-through conversions, and conversation-influenced conversions—not just direct response metrics that capture only a fraction of the value.

The sophisticated agencies will also explain how they establish baseline performance metrics before launching campaigns, so they can measure incremental impact. They'll describe methodologies for A/B testing conversational ad strategies, running holdout groups to understand organic versus paid influence, and using causal inference techniques to isolate advertising effects from other marketing activities. They'll acknowledge that measurement in conversational advertising is part science, part art, and entirely different from anything that came before.

Red flags appear when agencies promise "complete attribution" or claim they can "track every conversion." These promises are either dishonest or naive. Conversational advertising operates in a privacy-conscious environment where OpenAI doesn't share detailed user interaction data with advertisers. You'll get aggregated performance metrics, not individual user tracking. Agencies that promise traditional PPC-level tracking granularity either don't understand the platform's privacy constraints or are deliberately misleading you about what's possible. The honest agencies will explain the limitations, then show you how they work within those constraints to deliver meaningful performance insights.

Question 4: What's Your Approach to Creative Development for Conversational Contexts?

Creating effective ads for conversational AI requires completely different creative approaches than traditional advertising. Your ChatGPT ad isn't a banner, a video, or a sponsored post—it's a tinted text box that appears within an ongoing conversation, and it needs to feel like a natural, helpful contribution to that dialogue rather than an intrusive commercial message. The creative challenge is enormous: you need to be promotional enough to drive action but contextual enough to feel appropriate, brief enough to be digestible but informative enough to be valuable.

The best agencies will describe their creative development process in detail, emphasizing how they craft multiple ad variations for different conversational contexts. They should explain that a single product might require twenty or thirty different ad versions, each optimized for specific types of conversations. An ad for project management software appears differently in a conversation about remote team coordination than in a conversation about personal productivity or startup operations. The messaging, tone, and call-to-action need to adapt to the conversational context.

Ask them to show examples of how they structure conversational ad copy. Look for agencies that understand the importance of leading with value, not product features. In traditional search ads, you might lead with "50% Off Project Management Software!" In conversational advertising, that approach feels jarring and salesy. Instead, effective conversational ads might say something like "For remote team coordination, many companies are finding success with tools that integrate communication and task management..." followed by a specific mention of your product as an example worth exploring.

The sophisticated agencies will discuss their research into conversational user interfaces and how people respond to different messaging approaches in dialogue contexts. They'll explain their testing methodologies for determining which tone, length, and structure work best for different audience segments and conversational scenarios. They'll show you frameworks for balancing promotional content with genuine helpfulness—the core tension in conversational advertising. They'll describe how they collaborate with copywriters who understand dialogue writing, not just marketing copy.

Watch for agencies that show you traditional display ads or search ads as examples of their creative work. That's a massive red flag indicating they haven't actually developed conversational advertising creative yet. The creative requirements are so different that showing traditional advertising examples demonstrates they're still thinking in old paradigms. You want agencies showing you text-based, conversational ad examples that feel like natural dialogue contributions—even if those examples are from experimental campaigns or internal testing rather than live client work.

Question 5: How Do You Handle Brand Safety in AI-Generated Conversations?

Brand safety in conversational AI advertising presents challenges that don't exist in traditional advertising. When your ad appears next to a Google search result, you know the context—it's the search query. When your ad appears in the middle of a ChatGPT conversation, the context is an entire multi-turn dialogue that might have taken unexpected turns. What happens when your family-friendly brand's ad appears in a conversation that started innocuously but evolved into something controversial or inappropriate? This isn't theoretical—it's a genuine risk that requires sophisticated mitigation strategies.

The best agencies will explain their brand safety frameworks in detail, including both preventive measures and reactive protocols. They should discuss how they work with OpenAI's safety filters and category exclusions to prevent ad appearances in high-risk conversational contexts. They'll describe their processes for defining prohibited conversation topics, sensitive subject areas, and contextual red flags that should trigger ad suppression. They'll explain how they monitor campaign performance not just for clicks and conversions but for brand safety incidents and contextual appropriateness.

Look for agencies that have developed detailed brand safety guidelines specific to conversational advertising. These guidelines should go beyond traditional brand safety concerns (avoiding placement near violent or sexual content) to include conversational-specific risks like appearing in debates, controversial political discussions, or emotionally charged personal advice scenarios. The agency should show you their taxonomy of conversational contexts and explain which ones are appropriate for your brand and which ones require exclusion regardless of potential reach.

The sophisticated agencies will also discuss the philosophical tension in conversational advertising between reach and safety. Aggressive brand safety filters might eliminate 40% of potential ad placements, reducing campaign reach significantly. More permissive filters increase reach but elevate risk. The best agencies help you find the right balance for your brand's risk tolerance and reputation requirements. They'll present options, explain tradeoffs, and recommend strategies based on your industry, brand positioning, and competitive context.

Red flags emerge when agencies dismiss brand safety concerns or claim "the AI handles all that automatically." While OpenAI certainly implements safety measures, advertisers need additional brand-specific protections that go beyond platform defaults. Agencies that haven't thought deeply about brand safety in conversational contexts are agencies that will learn those lessons using your budget and your brand reputation as the testing ground. You want agencies who've already worked through these challenges, either through client work or through extensive pre-launch strategic planning.

Question 6: What's Your Relationship with OpenAI and Access to Beta Features?

The ChatGPT advertising program is still in early stages, with limited access and frequent feature updates. Your agency's relationship with OpenAI—and their access to beta features, early documentation, and direct support channels—can provide significant competitive advantages. Agencies with strong OpenAI relationships often get earlier access to new targeting options, measurement tools, and creative formats. They receive more responsive support when troubleshooting campaign issues. They get invited to advertiser summits where platform roadmaps are previewed months before public announcement.

Ask agencies directly about their OpenAI relationship status. Are they official beta partners? Do they have a dedicated OpenAI account representative? Have they been invited to advertiser advisory councils or early access programs? The answers reveal whether the agency is considered a strategic partner by the platform or just another advertiser with an API key. Strategic partners get better support, earlier feature access, and more direct influence on platform development—all of which translates to better campaign performance for their clients.

The best agencies will describe specific interactions with OpenAI that demonstrate partnership depth. They might mention participating in closed beta tests for new ad formats, providing feedback that influenced platform development, or attending invitation-only sessions where OpenAI executives preview upcoming features. They'll show you documentation proving their partner status and explain what that partnership means for your campaigns. They'll describe how they leverage their OpenAI relationships to solve client problems faster and more effectively than agencies without those relationships.

However, also watch for agencies that exaggerate their OpenAI connections. Some agencies claim "exclusive partnerships" that don't actually exist or imply special access they don't have. Verify their claims by asking specific questions: "Who's your OpenAI account manager?" "What beta features are you currently testing?" "When was your last meeting with OpenAI's advertising team?" Legitimate partners will answer these questions with specific names, features, and dates. Fraudulent claims will be vague and unverifiable.

Consider also that some excellent agencies might not have strong OpenAI relationships yet simply because they're newer to the space or smaller in size. What matters more than current partnership status is their plan for building that relationship and their track record of developing strategic partnerships with other advertising platforms. Agencies that have historically become Google Premier Partners or Facebook Marketing Partners demonstrate they know how to build platform relationships that benefit their clients. Those same relationship-building skills will serve them well with OpenAI.

Question 7: How Do You Approach Testing and Iteration in Such a New Medium?

Traditional PPC campaign management relies on decades of accumulated best practices, benchmark data, and proven strategies. Conversational AI advertising has none of that. Every campaign is essentially an experiment, and success requires agencies that are comfortable with ambiguity, rapid iteration, and learning from failure. The question isn't whether the agency will make mistakes—they will, because everyone will—but whether they have systematic approaches to learning from those mistakes and improving performance over time.

The best agencies will describe detailed testing frameworks that balance exploration with exploitation. They should explain how they allocate budget between proven strategies (even if "proven" just means "worked last week") and experimental approaches that might unlock breakthrough performance. They'll discuss their hypotheses development process—how they generate ideas for new targeting strategies, creative approaches, or bidding tactics to test. They'll show you documentation templates for recording test results, analyzing performance, and extracting learnable insights.

Look for agencies that think in terms of "learning velocity"—how quickly they can run experiments, gather meaningful data, and apply those learnings to improve campaign performance. In a rapidly evolving medium like conversational advertising, the agencies that learn fastest will dominate. Ask them how many distinct experiments they can run simultaneously, how they prioritize which tests to run first, and how they determine when they've gathered sufficient data to make confident decisions. The sophisticated agencies will have clear answers to all these questions, backed by methodologies adapted from statistical experimentation best practices.

The sophisticated agencies will also discuss their approach to documenting and sharing learnings. Since conversational advertising is so new, the agencies that systematically capture insights and build institutional knowledge will compound their expertise over time. Ask them: "How do you document campaign learnings?" "How do you share insights across clients?" "How do you train team members on emerging best practices?" You want agencies that are building knowledge repositories, not just running individual campaigns in isolation.

Red flags appear when agencies claim they "already know what works" or present rigid strategies without acknowledging uncertainty. In January 2026, nobody knows with certainty what works in ChatGPT advertising—the medium is too new and evolving too rapidly. Agencies claiming certainty are either lying or delusional. The honest agencies acknowledge uncertainty while presenting structured approaches to reducing it through systematic experimentation. They'll say things like "our hypothesis is X, and here's how we'll test it" rather than "we know X works because we've always done it that way."

Question 8: What Industries or Use Cases Do You Think Are Best Suited for ChatGPT Ads?

Not every business should be advertising on ChatGPT, at least not yet. Conversational AI advertising works brilliantly for some industries and use cases while delivering mediocre results for others. The best agencies have developed clear perspectives on where conversational advertising excels and where it struggles. They should be able to articulate not just why your business might succeed on the platform, but also which of your competitors might struggle and why. This strategic perspective—knowing where the medium works and where it doesn't—is what separates consultants from order-takers.

Expert agencies will typically identify several high-opportunity categories for conversational advertising. Software and SaaS companies often perform well because users frequently ask ChatGPT for tool recommendations and comparisons. Educational products and services benefit from the advice-seeking nature of many conversations. Complex products that require explanation rather than impulse purchase—financial services, B2B solutions, healthcare offerings—can use conversational ads to provide the detailed information users need. The agencies should explain the underlying reasons why these categories work, not just list industries randomly.

They should also identify categories that face challenges in conversational advertising. Low-consideration impulse purchases might not justify the cost of conversational ad placements. Highly regulated industries like pharmaceuticals might struggle with the lack of precise control over ad context and messaging. Local businesses with limited geographic reach might find the audience targeting too broad for efficient campaigns. The agencies willing to discuss where conversational advertising doesn't work demonstrate intellectual honesty and strategic sophistication—they're trying to help you succeed, not just sell services.

Ask them specifically about your industry and business model: "Given what you know about our company, why do you think we should or shouldn't be advertising on ChatGPT right now?" The best answer might actually be "you shouldn't—yet." An agency that tells you to wait six months until the platform develops better features for your specific use case, or until industry benchmarks emerge that justify the investment, is an agency that prioritizes your success over their revenue. That's the kind of partner you want.

The sophisticated agencies will also discuss timing and sequencing. They might recommend starting with small experimental budgets to test hypotheses before scaling, or focusing initially on specific product lines or audience segments where success seems most likely. They'll explain how they'd sequence campaign development, starting with highest-confidence opportunities and expanding into more speculative areas once they've established baseline performance. This strategic thinking about prioritization and sequencing demonstrates they're thinking about your success holistically, not just about launching campaigns quickly.

Question 9: How Do You Stay Current as the Platform Evolves Weekly?

ChatGPT advertising is evolving at unprecedented speed. New targeting options launch monthly. Creative specifications change based on user feedback. OpenAI releases new features, deprecates old ones, and modifies platform policies faster than most agencies can update their documentation. In this environment, staying current isn't a nice-to-have capability—it's a core competency that directly impacts campaign performance. An agency that's three weeks behind on platform updates is an agency that's missing opportunities and wasting your budget on obsolete strategies.

The best agencies will describe systematic approaches to monitoring platform evolution. They should explain who on their team is responsible for tracking OpenAI announcements, how frequently they review platform documentation, and what processes they use to rapidly implement new features in client campaigns. They might mention participating in OpenAI developer forums, subscribing to official update channels, attending platform webinars, or maintaining relationships with other agencies to share intelligence about platform changes.

Look for agencies that have formalized their learning and implementation processes. They might describe weekly platform update meetings where the team reviews changes and discusses implications for client campaigns. They might show you internal documentation systems where they track feature releases, performance changes, and emerging best practices. They might explain their rapid response protocols for implementing new features—how quickly they can test a new targeting option after it launches and roll it out to appropriate client campaigns if it proves effective.

The sophisticated agencies will also discuss their participation in broader AI and advertising communities. They'll mention attending relevant conferences, following AI researchers and advertising technologists on social media, reading academic papers about conversational interfaces and user behavior, and engaging with thought leaders who are shaping the future of AI advertising. They understand that staying current on ChatGPT advertising requires staying current on AI development generally, since platform evolution is driven by broader technological advances in large language models and conversational interfaces.

Red flags emerge when agencies can't articulate specific mechanisms for staying current. Vague answers like "we keep up with industry news" or "we read blogs" suggest they don't have systematic processes for platform monitoring. In a space evolving this rapidly, unsystematic approaches to staying current guarantee the agency will fall behind. You want agencies that treat platform monitoring and rapid learning as core operational capabilities, with dedicated resources and formal processes ensuring they're always working with the latest platform knowledge.

Question 10: Can You Explain Your Pricing Model and Why It's Structured That Way?

Pricing structures reveal an agency's fundamental business philosophy and their confidence in delivering value. For ChatGPT advertising—where performance benchmarks don't exist, best practices are still emerging, and campaign management requires significantly more strategic thinking than traditional PPC—pricing models vary wildly across agencies. Some charge traditional percentage-of-spend fees, which can create perverse incentives when the goal should be efficiency, not spending. Others charge flat monthly retainers that might not scale appropriately with campaign complexity. The best agencies have thought carefully about pricing models that align their success with yours.

Expert agencies will explain their pricing rationale in detail, connecting their fee structure to the specific value they deliver and the work required for ChatGPT advertising. They might argue for higher fees than traditional PPC management because conversational advertising requires more strategic input, creative development, and custom analysis. They should be able to break down where your money goes: what percentage covers platform management, what portion funds creative development, how much supports strategic consulting and performance analysis. This transparency demonstrates they've thought carefully about value delivery, not just set arbitrary prices.

Look for agencies willing to discuss pricing flexibility and performance incentives. The best arrangements often include base fees that cover essential management work plus performance bonuses tied to achieving specific outcomes. These performance incentives align agency success with client success—the agency makes more money when you make more money. Ask them: "What portion of your fee is at risk based on performance?" and "What metrics determine performance bonuses?" The answers reveal whether they're confident enough in their capabilities to put their compensation at risk.

The sophisticated agencies will also discuss pricing evolution as campaigns mature. They might propose higher initial fees during the learning phase when campaigns require intensive optimization and experimentation, with fees decreasing once best practices are established and campaigns run more efficiently. Or they might propose the opposite: lower initial fees during proof-of-concept testing with increases as campaigns scale and complexity grows. Either approach can be valid—what matters is that they've thought about how pricing should evolve with campaign maturity and can justify their approach.

Red flags appear when agencies can't clearly articulate their pricing rationale or when their pricing seems disconnected from the work required. If an agency charges the same percentage of spend for ChatGPT advertising as for Google Ads management, they're likely either overcharging for Google Ads or undercharging for ChatGPT advertising—because the work requirements are dramatically different. If they can't explain why their fees are higher or lower than competitors, they probably haven't thought strategically about pricing. You want agencies that can defend their pricing based on specific value delivered, not just market rates or historical precedent.

Why This Decision Matters More Than You Think

Choosing a ChatGPT ads agency isn't just selecting a vendor to manage another advertising channel—it's choosing a strategic partner who will shape how your brand participates in the biggest shift in digital marketing since social media. The decisions your agency makes in these early months will establish patterns, relationships, and positioning that compound over years. An agency that helps you establish thought leadership in conversational AI advertising creates advantages that persist long after campaigns launch. An agency that wastes six months pursuing ineffective strategies while your competitors learn and optimize puts you at a disadvantage that's difficult to overcome.

The strategic implications extend beyond advertising performance to broader business positioning. As conversational AI becomes the primary interface between consumers and information, brands that establish authoritative presence in these conversations gain structural advantages. They become the companies people think of first when they need solutions in your category. They build trust through repeated helpful appearances in valuable conversations. They gather insights about customer needs, concerns, and decision processes that inform product development, not just advertising. Your agency partner either helps you capture these strategic advantages or squanders the opportunity.

Consider also the talent implications of this decision. The best people in advertising want to work on cutting-edge challenges, not manage mature platforms with established playbooks. Hiring an agency that's genuinely pioneering conversational AI advertising gives you access to top-tier strategic talent who are attracted to the problem's complexity and novelty. Hiring an agency that's just rebranding their traditional PPC services gives you access to whoever they can staff on the account—likely not their best people, since the best people are working on the most interesting challenges.

The financial stakes are also higher than they appear. Industry observers suggest that conversational AI advertising will capture significant market share from traditional search advertising over the next three years. Early movers who establish effective campaigns now will ride that growth wave with steadily declining acquisition costs as they optimize. Late movers will enter a more competitive market with higher costs and more established competitors. The agency you choose now determines whether you're an early mover capturing growth opportunities or a late mover fighting for expensive scraps.

The Questions Behind the Questions: What They're Really Revealing

Each of these ten questions serves double duty—the surface question evaluates specific expertise, but the meta-question evaluates how the agency thinks, learns, and operates. When you ask about their preparation timeline, you're not just learning when they started studying conversational advertising—you're learning whether they're proactive or reactive, whether they invest in future capabilities or only respond to immediate market demands. When you ask about measurement approaches, you're learning whether they think rigorously about complex problems or prefer simple answers to complicated questions.

The best agencies reveal themselves not just through their answers but through how they engage with your questions. Do they welcome difficult questions or seem defensive? Do they acknowledge uncertainty or pretend to know everything? Do they ask clarifying questions to understand your specific situation or deliver generic presentations? Do they challenge your assumptions when appropriate or just agree with everything you say? These behavioral signals often matter more than the content of their responses, because they reveal the agency's culture, values, and operating philosophy.

Pay attention to whether agencies customize their responses to your specific business context or deliver the same pitch to everyone. The best agencies will ask detailed questions about your business model, competitive position, customer acquisition economics, and strategic objectives before proposing specific ChatGPT advertising approaches. They'll explain why certain strategies make sense for your situation and why others don't. They'll show you how they'd adapt their standard approaches to your unique requirements. This customization demonstrates they're thinking about your success specifically, not just selling a standard service package.

Also notice whether agencies educate or sell. The best agencies spend significant time teaching you about conversational AI advertising, explaining concepts, sharing frameworks, and helping you develop sophisticated understanding of the medium. They know that educated clients make better decisions, provide better feedback, and achieve better results. Agencies that rush through education to get to pricing and contracts are agencies that prefer uninformed clients who won't question their recommendations—not a dynamic that leads to exceptional outcomes.

Red Flags That Should End the Conversation Immediately

While the ten questions above help you identify excellent agencies, certain red flags should disqualify candidates immediately, regardless of their answers to other questions. If an agency guarantees specific performance outcomes in ChatGPT advertising, end the conversation. Nobody can guarantee performance in such a new medium with limited historical data and rapidly changing dynamics. Guarantees are either dishonest or backed by such conservative targets that they're meaningless. Ethical agencies discuss expected performance ranges based on assumptions while acknowledging uncertainty, not make promises they can't keep.

Similarly, if an agency claims they can "game the algorithm" or "hack ChatGPT's targeting," run away. These claims reveal fundamental misunderstanding of how AI systems work and demonstrate unethical approaches that will eventually backfire. Conversational AI advertising requires working with the platform's design, not against it. Agencies that think in terms of manipulation rather than optimization will waste your budget pursuing tactics that don't scale and might get your campaigns suspended when OpenAI's fraud detection systems catch them.

Watch for agencies that can't articulate clear differences between conversational advertising and traditional search advertising. If they keep saying "it's basically the same" or use Google Ads analogies for everything, they don't understand the medium well enough to manage campaigns effectively. The platforms are fundamentally different—different user behaviors, different intent signals, different measurement challenges, different creative requirements. Agencies that don't recognize these differences will keep trying to force square pegs into round holes until your budget runs out.

Be wary of agencies that criticize all other agencies or claim they're the only ones who truly understand ChatGPT advertising. The reality is that dozens of smart agencies are working hard to master this medium, and many are developing genuine expertise through different approaches. Agencies that position themselves as uniquely enlightened are usually covering for lack of substantive differentiation. The best agencies acknowledge that multiple valid approaches exist and explain why their particular approach fits your needs, not why everyone else is wrong.

Finally, distrust agencies that rush the decision process or pressure you to sign contracts quickly. They'll claim you need to "move fast before competitors gain advantage" or "lock in early adopter pricing before rates increase." These pressure tactics suggest the agency prioritizes closing deals over ensuring good fit. The best agencies want you to take time making informed decisions, talk to multiple candidates, and choose the partner that's genuinely right for your situation. They're confident enough in their capabilities to let you conduct proper due diligence rather than rushing you into commitments.

Building a Successful Agency Partnership Beyond the Selection Process

Choosing the right agency is crucial, but it's only the beginning of the relationship. The agencies that deliver exceptional results aren't just technically skilled—they're also effective collaborators who know how to work productively with clients. As you evaluate agencies, assess not just their ChatGPT advertising expertise but also their communication styles, reporting practices, and collaborative approaches. The most knowledgeable agency in the world won't help you if they can't effectively communicate insights or incorporate your feedback.

Discuss upfront how the agency approaches client collaboration. How frequently will you meet? What information will they need from you regularly? How do they handle strategy disagreements? What decision rights do they expect to have versus decisions that require your approval? The best agencies propose clear governance structures that balance their need for execution autonomy with your need for strategic control. They'll suggest regular strategy reviews where major decisions are discussed and debated, while delegating day-to-day tactical decisions to their team.

Ask about their reporting philosophy and what metrics they'll track. In conversational advertising where traditional metrics are less reliable, reporting becomes more complex and more important. You want agencies that provide context around numbers, explain performance trends, highlight learnings from experiments, and connect campaign metrics to business outcomes. Avoid agencies that dump spreadsheets of raw data without interpretation or those that cherry-pick metrics to make performance look better than it actually is. You need honest, insightful reporting that helps you understand what's working and why.

Consider also how the agency approaches knowledge transfer. The best partnerships involve teaching you about conversational advertising so your internal team develops expertise over time. Agencies confident in their ongoing value aren't threatened by client learning—they welcome it because educated clients provide better feedback and make better decisions. Agencies that hoard knowledge and keep clients dependent are agencies you'll eventually outgrow or resent. Look for partners who actively work to increase your team's sophistication, not those who prefer keeping you in the dark.

Frequently Asked Questions About Hiring ChatGPT Ads Agencies

How much should I expect to pay for ChatGPT ads management?

Pricing varies significantly based on campaign complexity, ad spend, and agency positioning. Most agencies charge either flat monthly retainers ranging from $3,000 to $15,000 for small-to-medium campaigns, or percentage-of-spend fees typically between 15-25% of ad spend. Given the strategic complexity and experimental nature of conversational advertising, expect to pay premium rates compared to traditional PPC management. Agencies charging significantly below market rates likely lack genuine expertise or will underinvest in your campaigns.

Should I hire a specialist ChatGPT ads agency or a full-service digital agency?

For now, specialist agencies with deep ChatGPT advertising focus generally deliver better results than full-service agencies dabbling in the space. Conversational advertising requires such different approaches from traditional channels that generalist agencies struggle to develop genuine expertise while managing multiple platforms. However, if you need integrated campaigns spanning multiple channels, look for full-service agencies that partner with ChatGPT specialists rather than claiming in-house expertise they don't yet have.

How long does it take to see results from ChatGPT advertising?

Initial performance signals emerge within 2-4 weeks as campaigns gather data and agencies complete initial optimizations. However, truly optimized performance typically requires 8-12 weeks as agencies test different approaches, identify winning strategies, and scale what works. Be suspicious of agencies promising immediate results—conversational advertising requires learning periods that can't be rushed. Set expectations for a 90-day optimization cycle before evaluating whether campaigns are succeeding.

Can I manage ChatGPT ads in-house instead of hiring an agency?

In-house management is possible if you have team members with time to develop expertise, appetite for experimentation, and comfort with ambiguity. However, most companies benefit from agency expertise during at least the first 6-12 months. Agencies working across multiple clients learn faster than any single company can and bring pattern recognition that accelerates your optimization. Consider starting with an agency and transitioning to in-house management once you've established baseline performance and developed internal capabilities.

What questions should I ask about data privacy and user information?

Ask agencies how they handle any user data they might access through campaign management, what data security protocols they follow, and how they ensure compliance with privacy regulations like GDPR and CCPA. Confirm they understand OpenAI's data usage policies and advertiser data restrictions. Reputable agencies will have clear data governance policies and be willing to sign data protection agreements. They should also explain what user information you will and won't receive from ChatGPT advertising campaigns.

How do I know if an agency is actually getting results or just spending my money?

Establish clear success metrics upfront that connect to business outcomes, not just vanity metrics. Insist on regular reporting that shows not just impressions and clicks but conversions, cost per acquisition, customer lifetime value, and return on ad spend. Ask for transparency into optimization actions—what experiments they're running, what they're learning, how they're applying those learnings. Request access to the advertising dashboard so you can verify their reports. Strong agencies welcome accountability and proactively demonstrate value.

Should I hire an agency that also offers traditional PPC services or a ChatGPT-only specialist?

Both models can work depending on your needs. Agencies offering both traditional PPC and ChatGPT advertising can help you optimize budget allocation across channels and develop integrated strategies. However, ensure their ChatGPT team is distinct and sufficiently staffed—not just their Google Ads team learning on the side. ChatGPT-only specialists often have deeper expertise but may lack perspective on how conversational advertising fits into broader paid media strategies. Evaluate based on the specific expertise of the people who'll work on your account.

What's a reasonable test budget for initial ChatGPT advertising campaigns?

Most agencies recommend initial test budgets between $5,000 and $25,000 per month for at least three months. This provides sufficient data to test multiple targeting approaches, creative variations, and bidding strategies while drawing meaningful conclusions. Smaller budgets risk insufficient data for optimization decisions. Larger initial budgets risk overspending before learning what works. Start conservative, establish baseline performance, then scale budget as you identify winning strategies that justify increased investment.

How do I evaluate an agency's creative capabilities for conversational ads?

Ask to see examples of conversational ad copy they've created, even if from test campaigns or theoretical exercises. Evaluate whether the copy feels natural and helpful rather than salesy and promotional. Ask about their creative development process, how many variations they typically test, and how they adapt messaging to different conversational contexts. Strong agencies have copywriters who understand dialogue writing and can create ads that enhance rather than interrupt conversations. Request sample campaigns for your specific business to assess their ability to understand your value proposition.

What should I do if campaign performance is disappointing after three months?

First, ensure you had realistic expectations given the experimental nature of conversational advertising. Review whether the agency conducted systematic testing, documented learnings, and applied insights to optimization. If they can show clear learning progression and reasonable optimization actions, consider extending the test period—some strategies take longer to prove out. If they can't demonstrate systematic learning or if their approach seems haphazard, it may be time to find a new agency. Conversational advertising is difficult, but good agencies show clear progress even when absolute performance is still building.

Can ChatGPT advertising work for local businesses with limited geographic reach?

Geographic targeting in ChatGPT advertising is still evolving, making local campaigns challenging in early 2026. However, for businesses in major metropolitan areas or those serving specific regions, conversational advertising can work if targeting strategies focus on local intent signals beyond just geography. Discuss with agencies whether they can target conversational contexts that indicate local intent—people discussing moving to your area, asking about local services, or mentioning nearby landmarks. Local success requires creative targeting approaches until platform geo-targeting capabilities mature.

How important is industry experience when selecting a ChatGPT ads agency?

Industry experience matters less for ChatGPT advertising than for mature channels because best practices are still emerging across all industries. An agency with deep expertise in conversational advertising mechanics can likely succeed in your industry even without prior category experience. However, agencies with relevant industry knowledge can ramp faster and bring valuable perspective on competitive dynamics, customer psychology, and effective messaging. Prioritize conversational advertising expertise first, industry experience second—but the combination of both is ideal when available.

Making Your Decision: A Framework for Final Selection

After conducting interviews and evaluating multiple agencies against these ten questions, you'll likely have several qualified candidates. Making the final selection requires weighing multiple factors—expertise, cost, cultural fit, capacity, and strategic vision. Create a structured evaluation framework that scores agencies across the dimensions most important to your situation. Don't rely on gut feeling alone, but also don't ignore it entirely—your instinctive sense of which agency "gets it" and which ones are performing often proves accurate.

Consider conducting a paid pilot project with your top two or three candidates before committing to long-term contracts. A four-week strategy development engagement where each agency creates detailed ChatGPT advertising plans for your business reveals far more about their capabilities than any interview process. You'll see how they think, how they work, and what level of strategic sophistication they bring. The investment in multiple strategy projects pays for itself by dramatically reducing the risk of selecting the wrong long-term partner.

Don't underestimate the importance of team chemistry and communication compatibility. You'll be working closely with this agency during a period of rapid learning and frequent strategy adjustments. Agencies that communicate in ways that match your preferences, respond to feedback constructively, and engage collaboratively rather than defensively will deliver better outcomes than slightly more expert agencies that are difficult to work with. The best technical expertise in the world doesn't help if you dread every meeting and communication breaks down under pressure.

Finally, trust your assessment of the agency's learning velocity and adaptability. In such a rapidly evolving medium, the agency that's best today might not be best in six months if they can't keep pace with platform evolution. Choose agencies that demonstrate systematic learning approaches, intellectual curiosity, and comfort with ambiguity. These qualities predict success in dynamic environments better than current expertise alone. You want partners who will evolve with the platform, not ones who'll be obsolete by the time they finally master the current state.

Conclusion: The Strategic Advantage of Choosing Well

The agency selection decision you make in early 2026 will echo through your marketing strategy for years. Choose well, and you'll establish dominant position in conversational AI advertising while competitors are still figuring out whether to participate. You'll build institutional knowledge, capture early-mover advantages, and develop sophisticated capabilities that compound over time. Choose poorly, and you'll waste six months and significant budget learning lessons you could have avoided while competitors pull ahead. The stakes justify investing serious time and energy in this decision.

The ten questions presented here aren't just an interview script—they're a framework for understanding what genuine expertise in conversational AI advertising looks like. Agencies that answer these questions well demonstrate they've thought deeply about the strategic, technical, and operational challenges of this new medium. They've invested in building capabilities before it was profitable to do so. They've developed sophisticated perspectives on what works and why. They're prepared to be true strategic partners, not just vendors executing your instructions.

Remember that you're not just hiring advertising management services—you're choosing a partner who will help you navigate one of the most significant shifts in digital marketing history. The rise of conversational AI as the primary interface between consumers and information fundamentally changes how brands build awareness, establish authority, and drive consideration. Your agency partner either helps you capitalize on this shift or becomes another expense line while competitors capture the opportunity. Make the choice that sets you up for long-term strategic advantage, not just short-term campaign execution.

As you move forward with agency selection, revisit these questions regularly. The right answers will evolve as the platform matures and industry best practices emerge. An agency that gives excellent answers today should give even better answers six months from now as they accumulate experience and insights. Regular reassessment ensures your agency partner continues delivering value as both your needs and the platform itself evolve. The goal isn't finding perfection today—it's finding a partner committed to pursuing excellence over time as you build conversational advertising capabilities together.