26 Questions to Ask Before Hiring a Marketing Agency
Choosing a marketing agency means committing real budget to a partner whose work you often can’t evaluate properly until months in. These 26 questions come from agency founders, CMOs, and business owners who have sat on both sides of that table: the people writing the retainer checks and the people cashing them.
One business here paid $6,000 a month for four months before realizing the reports tracked clicks, not booked jobs. A clinic owner discovered weeks after signing that the analytics access she’d handed over reached patient data she had no right to share. Neither problem was expensive to prevent. Both were expensive to unwind.
Nobody asks 26 questions in a discovery call. Read them, then pick the five that match your real exposure: budget, regulation, in-house capacity, or how badly you’d be hurt if the relationship ended in month four.
Part 1. Diagnosis: Do They Understand the Problem?
Before anyone proposes tactics, find out whether they can name what’s actually wrong. Agencies that skip straight to deliverables are selling what’s easy to sell, not what you need.
What do you believe is limiting our growth?
Before hiring an agency, the better question is what they believe is limiting growth. Too many engagements begin with activity when the smarter starting point is a clear diagnosis. If an agency cannot name the bottleneck, they may treat symptoms instead of causes. A useful partner should explain what they would investigate first and why.
The strongest agencies are precise before they become busy. They should explain which signals they trust and which ones may be misleading. That conversation shows whether they think like operators or simply act like vendors. A strong agency should bring a clear point of view because clarity leads to better decisions than constant motion early.
Mark Bietz
CMO, Halloween Costumes
What has to be true about my website before your plan produces results?
Most agencies sell what is easy to sell. A content calendar looks like progress, so that is what lands in the proposal. The uncomfortable answer is that content on a technically broken or thin site does very little, and you end up paying twice, once for the content and again when you fix the foundation and re-evaluate everything that underperformed.
The red flag is a content plan proposed before anyone has looked at whether your service pages are even eligible to rank. That should worry you.
I have seen businesses with eighty blog posts and a core service page so thin it did not explain what they actually offered. All that spend, almost nothing to show for it in the queries that drive real inquiries.
So the question I wish more owners asked up front is simple. Before we make more, what do we need to fix in what we already have? An agency that has a real answer is worth hiring. One that pivots straight to volume is not.
Trevor Gage
Director of Marketing, Webserv
What will you stop us from doing?
Most agency relationships begin with promises about what gets added: more ads, more content, more channels, more reporting. Mature strategy is often subtraction before expansion.
I have seen companies grow faster when someone removes noise, conflicting offers, weak landing pages, vanity metrics, and poorly timed campaigns. A strong agency should identify where the brand is diluting trust or splitting intent before trying to scale traffic. That answer reveals whether the team understands economics, not just execution. The best partners protect focus, because disciplined omission usually creates more profit than a longer marketing checklist.
Jason Hennessey
CEO, Hennessey Digital
How will you learn enough about our customers to market us accurately?
At Mills Shelving, our customers aren’t simply searching for shelves. They may be fitting out a new store, replacing an ageing system, working around unusual floor dimensions or trying to display a particular product range more effectively. An agency can understand marketing extremely well and still miss those commercial nuances.
Before hiring, I’d ask the agency to explain how they’ll learn the business, customers and buying process before they start executing. The best marketing should sound like it comes from people who understand why customers buy from you, not just which keywords they search.
Neil Webster
CEO, Mills Shelving
What internal truth do you need from us to succeed?
Too many relationships fail because agencies receive polished stories instead of real business details. Growth work becomes harder when partners only hear the version a company shares with investors or customers. The strongest agencies ask for honest inputs early.
They want to know where margins are weak and which segments churn. They also need to understand where teams disagree and what cannot scale behind the scenes. We have learned that clean messaging built on messy economics can create false confidence. A serious agency should explain which business truths matter most and why.
Chirag Kulkarni
Founder & CEO, Taco
What are you assuming about our business that we haven’t told you?
Most agency conversations focus on plans, timelines, and expected results. Few take time to discuss assumptions about our audience, buying intent, team capacity, or how quickly we can handle change. Those assumptions shape every recommendation and can affect the work.
When those assumptions stay unspoken, both sides can feel aligned while working toward different outcomes. That is where frustration can begin. A thoughtful agency should explain what needs to be true for its strategy to work and what could cause problems. Asking those questions early helps us choose an agency for clear thinking rather than confidence.
Sahil Kakkar
CEO / Founder, RankWatch
Part 2. People: Who Is Actually Doing the Work?
Four contributors raised versions of this question independently, from four different industries. That’s not a coincidence. The gap between the person who pitches you and the person who executes is the most reliable failure point in agency work.
Who is the actual person doing the work, and what percentage of their time goes to us?
The retainer scope looked airtight until month three, when we realized “unlimited revisions” meant unlimited rounds on one asset at a time, not the eight concurrent projects we had running.
At 3D Studio we hire subcontractors and outside agencies for specific campaigns, and the question I wish I had asked upfront was: who is the actual person doing the work, and what percentage of their time goes to us? The account manager on the sales call is never the person building your assets. Finding out our “dedicated team” was one junior contractor splitting time across eleven clients explained a lot about the response times.
The mechanism that kills most agency relationships is the handoff gap. You’re sold by someone senior, then quietly transitioned to whoever has capacity. No one announces it. The quality drift is gradual enough that you rationalize it for two or three months before realizing you’ve paid for a service that stopped existing around week six.
Ask them to name the specific person doing the work and show you their current client load. Ask what happens to your account when that person leaves. If the answer is vague, the accountability is vague.
Siim Kostabi
Founder, 3Dstudio.co
Who on your team will touch my account day to day?
I ran a social media agency for years, grew it to 10 employees and 150 clients, and the question I almost never got was who on our team would actually touch their account day to day. Clients hired the agency’s name and got whoever had capacity that month. Ask for the specific person, not the case study logo wall. I sold the company to my business partner, and the accounts that lasted longest were the ones where the client had built a relationship with one person, not with us.
Einav Biri
Owner, Angel Number Guru
Can I talk directly to the person opening my Seller Central account?
After ten years running an Amazon-focused agency, the question I wish more business owners asked before signing is: who exactly will be touching my account day to day, and can I talk to that person directly? Agencies sell you on the founder or the sales lead during the pitch, then hand you off to a junior account manager you’ve never met. Ask for the name and experience level of the person who will actually open your Seller Central account.
Second, ask how they define success before they define it for you. An agency can lower your ACOS by turning off Sponsored Products campaigns entirely, but that also lowers your sales. I tell prospective clients to ask any agency whether they optimize for ACOS, TACOS, or net profit after Amazon fees, because those three metrics can point in different directions.
Third, ask who owns the account data and creative assets if you leave. Some agencies build their reporting and keyword research inside tools you never get access to, which makes switching painful later.
Last, ask about their SP-API and Advertising API access setup specifically, since that tells you whether they’re running real account-level automation or just logging into the dashboard manually like everyone else.
Jimi Patel
Director, eStore Factory LLC
Who on your team actually posts online, and has anything they made gone viral under their own name?
Most agencies sell you a process and a reporting dashboard, but marketing today is about taste and being native to the platform, and you can’t outsource taste to someone who’s never felt the dopamine of a post popping off. If nobody on the team lives on X or TikTok, they’ll hand you safe, forgettable content that checks every best-practice box and moves nothing.
I’d also ask them to show real organic wins, not paid impressions. Anyone can buy reach. The hard part is making something people share for free. Ask for the actual posts, the actual numbers, and whether the work was funny or just polished. If their portfolio is all logos and “brand awareness” with no receipts, run. You want a partner who can make people stop scrolling, not one who makes a pretty slide about it.
Jason Levin
CEO/Founder, Memelord.com
How does your team develop judgment internally?
Business owners often evaluate pitch quality, past results, and pricing, but overlook the internal culture producing the work. Growth outcomes are shaped by the daily decisions of people interpreting signals, prioritizing actions, and communicating tradeoffs under pressure.
We tend to trust partners more when their leadership model creates self-aware operators, not just skilled specialists. Teams with strong internal coaching usually escalate problems faster, collaborate better across functions, and make fewer ego-driven decisions when results fluctuate. That has a direct commercial effect because disciplined judgment protects execution quality at scale. In a market where discovery is fragmented and attention is expensive, the agency’s internal maturity often becomes the unseen advantage that determines whether performance compounds or plateaus.
Marc Bishop
Director, Wytlabs
What percentage of our deliverables will be AI-generated, and will you tell us when that changes?
Most owners assume the answer is zero, or they assume the question is rude to ask. Neither assumption serves them. Nearly every agency is using these tools now, the honest ones have a written policy and the rest have a habit they would rather not discuss on a sales call.
I run an AI-powered agency, so my position here is not neutral. Around 95 percent of our blog content starts with AI, and we say so in writing. What matters is the review layer, who reads the output before it reaches a client, and whether that person has the standing to throw it out.
The uncomfortable part is that I did not always know what my own team was using. There was a stretch where people were working with a tool I had not approved, and I found out late. That is not a story I enjoy repeating, but it is why disclosure stopped being a marketing position for me and became an operating requirement.
Then ask the follow-up, which matters more than the first question. What does a human actually add? If the answer is proofreading, you are paying agency rates for a prompt. If the answer is strategy, judgment, and knowing when the output is confidently wrong, that is worth a retainer.
The test I use is straightforward: would I be comfortable if the client saw exactly how this was made? An agency that hesitates at that question has already answered it.
Carlos Rios
Founder, Tabula
Part 3. Measurement: How Will You Know It’s Working?
Almost every contributor who described a failed engagement traced it back to measurement that was agreed too loosely, or never agreed at all.
What exactly will you measure, how often will you report it, and how does each number connect to sales?
A $6,000 a month engagement went for four months before anyone noticed the agency was reporting clicks and impressions, not booked jobs or qualified leads. If they can’t map activity to outcomes like cost per lead, lead-to-sale rate, and revenue by channel, the reporting will usually stay at the vanity level.
A trades business with about 25 staff changed agencies after asking for that link. The new team set up call tracking, form attribution, and a basic CRM pipeline view. Cost per lead came down from about $118 to $72 in three months, and about 35 per cent of new jobs could then be traced back to Google Ads and organic search instead of guesswork.
I’d ask that before anything else because most agency problems start with misaligned measurement. Good creative and media buying help, but if success isn’t defined in commercial terms from day one, it’s hard to know whether the agency is helping or just staying busy.
Josiah Roche
Fractional CMO, JRR Marketing
How do you define a qualified lead, and what happens when a channel isn’t converting?
I wish I had asked more directly how an agency defines success before we ever signed on. Early on, we cared about more traffic or more followers, when what actually mattered was whether the leads coming in were the kind our team could close. An agency that measures activity instead of qualified leads will happily report good numbers that never turn into real orders.
The other question I would ask now is how quickly they adjust when something is not working. Some agencies will keep running the same approach because it is easy to report on, not because it is producing results. I want to know upfront how a partner handles being told a channel or a tactic just is not converting for us.
Eric Turney
President / Sales and Marketing Director, The Monterey Company
How do you define wasted spend, and will you report it separately from Google’s Optimization Score?
I audit Google Ads accounts for a living, and the gap between those two numbers is where most retainers hide. One account in this corpus held a 99.1% Optimization Score while 18.7% of spend still went to zero-conversion search terms and CPC sat 14% above the vertical median. Another account in the same niche scored 48.8% and was the leanest in the set, with 8.9% waste and CPC 64% below median. If an agency cannot explain waste without pointing at Google’s own score, you are buying a dashboard, not accountability.
Igor Ivitskiy
Founder, Doctor Ads
Can you show the exact KPIs you improved for a business like ours?
Ask for evidence of measurable success with businesses that match your model and markets, not just polished case studies. Insist on examples showing the exact KPIs they improved (conversion, AOV, unsold inventory reduction), the tactics used, and the reporting cadence so you can verify progress.
From running MusaArtGallery, I value partners who share concrete metrics and a repeatable process because that’s how we validated a pricing project that cut unsold inventory and improved margins.
THERY Jean Christophe
CEO, MusaArtGallery
How many closed deals in my local market do you generate per month?
I am very adamant that when I meet with any marketing company to discuss marketing, I always ask the question of how many local real estate deals they generate per month. I tend to steer clear of generic marketing agencies. Most of them attract useless out-of-market leads. If they can’t produce proof of local sellers and buyers converted into deals, I won’t do business with them.
Geremy Yamamoto
Founder, Eazy House Sale
What is your strategy for how AI models describe our brand?
Most founders ask a lot about rankings for traditional search. But if an agency optimizes only for Google’s traditional search engine, your business may vanish from the conversation. This is because, unlike traditional search, where users scan multiple results, AI assistants (like ChatGPT, Perplexity, Google AI Overview, etc.) provide synthesized answers, usually just one or two. If your brand isn’t proactively shaping the information available about it, the AI may scrape outdated information, fragmented messaging, and competitor-driven content.
Make sure that any agency you interview has this AI monitoring and feedback loop in place. Do they test what ChatGPT says about your brand? Do they have a Generative Engine Optimization (GEO) strategy to be cited in the output of AI models?
It’s too late after an AI engine hallucinates negative content about your company. The ones that win are those that can steer how AI interprets, trusts, and recommends them.
Ulf Lonegren
Executive Director of AI, Sōvyn
Part 4. Commercials: Incentives, Money, and Time
The next two answers point in opposite directions, and the tension between them is worth sitting with. One contributor argues that any agency willing to commit to specific outcomes isn’t serious. The other argues you should hand over your margins and make them forecast a return before you sign. Both are describing the same risk from different sides: an agency that promises numbers it can’t control is a liability, but an agency that won’t model the economics at all may not understand them. What you’re testing for is whether they can reason about your unit economics out loud, not whether they’ll guarantee a result.
Give us your margins: what should blended ROI be, and how do you get there?
Give them your gross product margins and net margins, and ask them to do a quick forecasting exercise: what should blended ROI be based on their targets, and how do they get there? Ask for the media plan. If they go through this exercise, then you can hire them.
Ask if they have worked with similar-size companies. If you are a startup and need scale from ground zero, you need an agency that knows how to operate with limited budgets.
Meet their team before signing the contract.
Donnie Strompf
Founder & Marketing Strategist, Good At Marketing
Do you prioritize results or the steps that produce them?
No one can guarantee anything, especially not an agency tasked with delivering certain results. Sure, they can aim for a goal, but guaranteeing something is, to me, a sign that they’re not really serious. The best agencies take the necessary steps to ensure they meet their goals, and the results usually follow, not the other way around. If an agency is focused on doing the right things to help you grow, they’re already ten times better than another agency promising results with no actionable steps.
Gabriel Shaoolian
CEO and Founder, Digital Silk
How do you decide when less activity is the better recommendation?
I wish more owners asked how the agency handles conflicting incentives. The agency may be rewarded for increasing activity, while the business actually needs better efficiency, retention, or stronger commercial outcomes. Those goals can look aligned initially and drift apart as the relationship grows.
One revealing question is how the team decides when less activity is the better recommendation. If the answer is vague, the commercial model may be encouraging volume rather than judgment. A sustainable partnership works when the agency can reduce unnecessary work without feeling financially punished for doing so. Alignment becomes much easier when both sides benefit from better decisions, not simply more deliverables.
Dawood Bukhari
CEO, Digital Web Solutions
What do you need from us each week, in hours and by name, and who chases us when we’re late?
I have hired agencies for content, paid media and store work, and the brief always covers what they will deliver. It rarely covers what they need back. Every campaign needs product photography, a claims check, someone to approve a subject line, a founder to answer the question only the founder can answer. If nobody has costed that, the work stalls on your desk and both sides end up disappointed.
Our first content retainer ran for weeks producing almost nothing, and the agency was not at fault. Drafts sat in my inbox waiting for a compliance read that only I could do. I worked out I was giving it about 6 hours a week of my own attention, which neither side had budgeted for, and those hours were coming out of the parts of the business only I could run.
Now I ask two things before signing. What do you need from us each week, in hours and by name? And who chases us when we are late? Because an agency that quietly waits is an agency that will bill you for a month of nothing.
The good ones welcome that conversation. They have lost more accounts to client bottlenecks than to poor work, and they know it.
Neill David Watson
Founder, APMZEE
If success takes longer than expected, how will confidence be protected on both sides?
That gets overlooked, yet many agency relationships fail during the gap between early effort and visible outcome. When expectations are not grounded in real timelines, normal variance starts to feel like underperformance, and trust erodes before the strategy has time to mature.
That question reveals whether the agency knows how to manage uncertainty with clarity and evidence. It also shows whether they can explain progress in a way that keeps decisions rational under pressure. I have learned that client confidence is not a soft factor. It directly affects patience, consistency, and the quality of every next decision.
Brian Hansen
President, Rocket Pilots
Part 5. Exit: What Do You Keep?
Ask these before you sign, because they are almost impossible to negotiate once the relationship is already deteriorating.
What knowledge, accounts, data, and working assets will we own when the engagement ends?
An agency can deliver good work while leaving the client dependent on the people who performed it. The risk often appears later. Campaign history sits in an agency-controlled account, decisions were made in calls without a written record, source files are unavailable, or nobody inside the business understands why a channel was chosen.
I now treat knowledge transfer as part of the deliverable. Before work starts, I want ownership clarified for advertising accounts, analytics, domains, creative files, customer research, reporting definitions, automation, and documentation. Access should be created in the client’s name where practical, with the agency receiving the permissions it needs.
The agency should also explain how decisions will be recorded. A monthly report can show activity without preserving the reasoning behind it. I want to know what was tested, what assumption informed the test, what was learned, and what the next decision will be. That record lets the business compound learning instead of restarting whenever a person or partner changes.
This does not mean the client should demand every internal agency template or proprietary method. The agency deserves to protect its own intellectual property. The boundary is whether the asset or knowledge is necessary for the client to operate, evaluate the work, or transition responsibly.
There is a tradeoff. Thorough documentation adds time, and small engagements can become inefficient if every minor action requires a formal record. I focus on decisions, access, reusable assets, and anything that would be expensive to reconstruct.
The failure mode is treating ownership language as protection against a poor fit. A contract cannot fix unclear goals, weak communication, or a mismatch between the agency’s strengths and the company’s actual problem. I ask who will do the work, how success will be judged, and what the first review point is.
A good agency relationship should leave the business more capable, even if the partnership continues. The client should understand its customers, channels, and choices better than before. If ending the engagement would erase that understanding, the business has rented activity rather than built a marketing asset.
Raj Baruah
Co-Founder, VoiceAIWrapper
Who owns the lead list, and do I get a full export the day I leave?
Owners sign on, hand over calendars and contact lists, and later find out none of it is theirs to keep. Ask upfront who owns the lead list, who owns the ad account, and whether you get a full export the day you leave. Ask about contract length too. Long lock-ins let an agency stall past the slow months before you can walk.
Ask how you’ll see the work, not just hear about it. A real report shows call-by-call detail, not a slide deck built to look good on a Friday. My own service runs month to month, cancel by email, no contract, because that’s the setup that keeps an agency honest. Ask what happens if the numbers don’t move in the first month. A vague promise to keep trying isn’t good enough. I want a real answer, in writing, before I sign anything.
Victor Smushkevich
Founder, Call Setter AI
Who on your team will be inside our systems, and will you sign a business associate agreement?
The question I wish I had asked first was not about strategy or price.
I run a primary-care practice, so anything touching patient information carries obligations that do not disappear because the work was outsourced. On our first search I sat through polished pitches about funnels and content calendars, signed with the agency that sounded most confident, and found out weeks later that the analytics access we had handed over reached data we were not free to share. Unwinding that was my problem, not theirs.
Now the question goes on the first call, ahead of everything else. Adding it removed 4 names from our shortlist before we saw a single proposal, which told me how common the gap is. The follow-ups matter as much: who does the work day to day, is it the person in this meeting or somebody I will never meet, and what happens to the accounts, the content and the data if we stop working together.
Any owner in a regulated field should ask it. Owners outside one should ask it too, because your customer list is the asset you are handing over, and the contract is the only place its handling is ever written down.
Anna Evans
Founder, Interlinked Wellness
Four Questions Nobody Raised (But You Should)
The 26 questions above came from operators describing what they’d learned the hard way. A few obvious gaps stood out by their absence:
“How exactly do you charge?” Retainer, hourly, or percentage of ad spend. A percentage-of-spend model rewards an agency for spending more of your money, which is the incentive conflict several contributors describe without naming its most common cause.
“Can I speak to a client who left you?” References are curated by definition. A churned client will tell you more in ten minutes than five case studies will.
“Do you work with our competitors?” Sector expertise and conflict of interest are the same fact viewed from two angles. Find out which one you’re getting.
“Do you subcontract or offshore any of this work?” Distinct from the AI disclosure question, and just as rarely volunteered.
The Bottom Line: What These Questions Really Test
Read together, these questions have less to do with marketing skill than you’d expect. Almost none of them ask whether the agency is good at advertising. They ask who does the work, what gets measured, what gets left behind, and whether the agency will tell you something you don’t want to hear.
That’s because agency relationships rarely fail on craft. They fail on ambiguity: an undefined lead, an unnamed account manager, an unbudgeted six hours a week of your own time, a data export nobody thought to ask about until the day it mattered. Every question here is an attempt to close one of those gaps in writing, before either side has a reason to be defensive about it.
Pick your five. Ask them on the first call. The answers you get, and how comfortable the agency is giving them, will tell you more than any proposal.
Author
Carlos Rios
Carlos Rios is the Founder of Tabula. Before starting the agency, he spent his career inside companies — reporting to leaders who had no patience for vanity metrics and wanted straight answers about what was working and why. He built Tabula around that same standard: a marketing system the client owns, powered by AI and led by experts who explain the plan in plain language. Carlos studied philosophy for six years at York University and holds a Master's in Marketing from the Schulich School of Business.
