Questions to Ask a CMO
For an employee, a vendor, or a peer with time in front of a chief marketing officer. 37 questions on where customers actually come from, what the budget funds, which numbers they trust, positioning, the sales handoff, agency mix, and where the team is thin.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
How would you describe what we sell to someone who's never heard of us?
Why ask it
The unscripted version tells you whether positioning has settled. If the answer differs noticeably from the website, the company is running two stories at once, and everyone below is choosing between them.
Where do most of our customers actually come from today?
Why ask it
Ask for the ranking, not the strategy. In many companies the top source is something unglamorous, referrals, an old partnership, branded search, that receives a small fraction of the attention and the budget.
What's taking most of the budget this quarter?
Why ask it
Spend is the honest plan. When the largest line does not match the priorities just described, something is either inherited, contractually locked, or protected by someone senior, and it is worth knowing which.
Which part of the funnel worries you most right now?
Why ask it
The named stage tells you where the pressure will land next: awareness problems become campaign work, conversion problems become website and pricing work, retention problems become product work that marketing cannot fix alone.
How do you know what's working? What does attribution look like here?
Why ask it
Listen for the acknowledged limits: last touch overweighting search, offline channels that cannot be measured cleanly, a long sales cycle that outruns the reporting window. A leader with no caveats is either not looking closely or not saying.
Who do we lose to, and what do those customers say about us?
Why ask it
Loss reasons in the customer's own words are the most useful marketing asset a company has, and often nobody collects them. If the answer is only about price, ask whether anyone has actually called the people who said no.
What are we claiming that customers don't quite believe?
Why ask it
Every company has one: the support promise, the ease of setup, the integration that technically exists. A CMO who names it is working on the gap; one who denies any gap has not read the review sites recently.
Which piece of work from the last year are you proudest of, and which would you take back?
Why ask it
The regret is the informative half, and it is a safe question because everyone has one. Note whether the regret is about the work itself or about the process that produced it, since the second is the one that repeats.
How much of this year's plan is already committed?
Why ask it
Sponsorships, event contracts, agency retainers, and annual tool licenses can consume most of a budget before the year starts. The uncommitted remainder is the only part where a new idea, including yours, can land.
Where does marketing end and sales begin here?
Why ask it
Ask for the handoff mechanics: who owns follow-up, what the response commitment is, what happens to leads nobody calls. The vaguer the boundary, the more of the pipeline is being lost in it.
What do you need from product that you aren't getting?
Why ask it
The answer names the constraint marketing cannot solve by spending more: a missing feature competitors lead with, unreliable onboarding, no roadmap visibility. It also tells you how these two functions talk to each other.
Which number are you reporting that you don't fully trust?
Why ask it
Almost every dashboard contains one figure everybody knows is soft. A CMO willing to name it understands their own instrumentation, and the answer tells you which claims elsewhere in the business to treat carefully.
What's the smallest change that made the biggest difference recently?
Why ask it
These stories are usually specific and unglamorous: a form field removed, a headline rewritten in customer language, an email sent two days earlier. They show whether the team tests things or only launches them.
How is the work split between the in-house team and agencies, and how's that going?
Why ask it
The friction points are informative: agencies retained for capacity rather than skill, work reviewed by nobody with the time to review it, briefs written after the work started. Ask when each retainer comes up for renewal.
Where's the team stretched thinnest?
Why ask it
The gap is usually a single person holding something critical: the one designer, the only analyst, whoever knows how the marketing automation is wired. That is where the next delay comes from, whatever the plan says.
What would you do with ten percent more budget, and what would go if you lost ten percent?
Why ask it
Asking both directions forces a real ranking. The cut list is more revealing than the wish list, because it shows what is genuinely believed to be working versus what is being kept for internal reasons.
What's the thing about our customers you keep having to repeat internally?
Why ask it
Every marketing leader has one fact colleagues will not absorb: how long the decision takes, who actually signs, what the product gets used for in practice. The repetition tells you where the company misreads its own buyers.
What did you push back on this year?
Why ask it
A campaign asked for by a founder, a sponsorship someone's contact suggested, a rebrand at the wrong moment. Whether they pushed back, and how it ended, tells you how much authority the function actually holds.
How much of your week is spent on things you'd rather someone else did?
Why ask it
The list is usually approvals, internal communications, and reporting requests. It shows you where the function is under-resourced, and if you work with this person, where you can be useful without being asked.
If I wanted to help, what's the thing nobody ever offers to do?
Why ask it
A closing question that produces something concrete: customer interviews, tidying up case studies, sitting in on sales calls, writing the thing everyone avoids. It also converts a pleasant conversation into a next step.
How do you decide the split between brand spend and performance spend?
Why ask it
Anyone can recite that both matter. The useful part is the mechanism: a fixed ratio, a payback threshold, a share of voice model, or a fight with finance every quarter. If there is no mechanism, the split is being set by whoever argues hardest.
What is the longest you have kept funding something before you could show it was working?
Why ask it
Brand, content, and community take quarters to register. This question surfaces both their patience and their political capital, since holding a line item with no near term proof means they had someone's trust.
Which channel have you cut, and what finally convinced you to cut it?
Why ask it
Cutting is harder than launching because someone owns the channel and its numbers. The evidence they accepted, and how long it took, says more about their standards than any success story.
What marketing number do you report to the CEO, and what do you watch that never makes the board deck?
Why ask it
The private metric is the one they actually trust. A gap between the two, reported pipeline versus something like organic branded search, tells you where they think the public number is soft.
How do you handle a quarter where marketing missed the number?
Why ask it
Listen for whether they describe explaining the miss, or diagnosing it. The best answers separate the parts of the funnel they controlled from the parts they did not, without shifting all of it to the market.
How do you and the head of sales settle disagreements about lead quality?
Why ask it
This argument exists at nearly every company. A concrete answer names a shared definition, a service level agreement, or a weekly review; a vague one about partnership usually means the fight is unresolved and ongoing.
What do you do when the product team ships something you cannot position?
Why ask it
Marketing gets handed features that solve no stated customer problem. The answer shows whether they have real influence upstream in the roadmap or are limited to making the best of what arrives.
What kind of research has actually changed your mind, and what mostly confirms decisions already made?
Why ask it
Almost everyone runs research; far fewer can name a decision it reversed. A specific reversal is evidence they can be argued out of a position with data.
How has your view of positioning changed since you started leading marketing?
Why ask it
Positioning statements are easy to write and hard to hold. Ask what they got wrong the first time, because most leaders can point to a message the market simply refused to repeat back to them.
What has a reputation problem taught you about how quickly to respond?
Why ask it
The instinct is to respond fast, and experienced leaders often say the opposite: verify first, then speak once. The example they choose also shows how much of crisis work is legal and internal rather than public.
Which piece of your marketing technology has earned its cost, and which is on probation?
Why ask it
Tool sprawl is expensive and rarely audited. Being able to name a system that is under review, and the criteria it is failing, is a sign someone is watching the spend.
What did the last agency relationship you ended get wrong?
Why ask it
You learn their standard for outside partners and how they handle a relationship going bad. An answer that blames only the agency, with nothing about the brief or the internal owner, is a partial account.
How do you hire for a role you have never done yourself?
Why ask it
Modern marketing spans lifecycle, analytics, brand, and technical work that no one leader has done all of. Look for borrowed judgment: work samples, trusted reviewers, paid exercises, rather than instinct.
What do you look for in a new marketer's first ninety days?
Why ask it
This is the clearest picture of what they reward day to day. Some want a shipped project, some want a written point of view on the market, and the difference predicts what working for them is like.
Which part of the job surprised you most when you went from running one function to owning all of marketing?
Why ask it
Specialists who get promoted usually name the same shock in different words: they now defend budgets for work they cannot personally evaluate. The answer shows what they had to learn fast rather than what they were already good at.
What part of this job do you expect to look unrecognisable in three years?
Why ask it
Their answer reveals where they are placing bets, and whether they are describing the industry's talking points or something they are already reorganising around.
If you were starting in marketing again now, what would you not spend your first five years on?
Why ask it
More useful than asking for advice, because it forces a subtraction. The specifics, a certification, a channel, a title chase, tend to be the things they are still slightly annoyed about.
Talking to a CMO
Practical guidance for the conversation itself
Match the questions to your seat
If you work there
Use the time on the reasoning behind a decision that shaped your work, not on the decision itself. Bring one example and ask what tradeoff it was solving. You will learn more, and you will not spend the meeting being defended at.
If you're selling
Ask what is already committed and when the relevant contract renews before you pitch anything. Most marketing budgets have almost no free space mid-year, and a good vendor conversation is about displacing a line item, not adding one.
If you're interviewing for the team
Ask what the last two people in this role did well and badly, how work gets approved, and which number the team is judged on. Then ask what happens when that number is missed for two quarters.
Getting past marketing language
- Ask for the number and the date. Strategy answers become checkable when tied to spend and a month.
- Ask for the customer's words rather than the segment name. Real quotes travel; personas rarely survive contact.
- Ask what was stopped. Every marketing leader can list launches, and fewer can list what was retired to make room.
- Ask who disagreed with the decision internally. The dissent explains the compromise you are looking at.
- Ask what would have to be true for the current plan to be wrong. It is a fair question and produces the most thoughtful answers.
What the answers tend to expose
- A company whose largest customer source gets the smallest share of attention, usually because it is hard to attribute.
- Positioning that lives in one person's head and has never been written down for sales to use.
- Attribution that stops at the first form fill in a business where decisions take six months.
- A brand budget kept alive to protect a relationship rather than because anyone measured it.
- One overloaded specialist who is quietly the dependency for every campaign.
Common mistakes
- Asking about trends. It invites a positioning answer and tells you nothing about this company.
- Critiquing the current campaign in the first meeting. Ask what constraint produced it before deciding it was a mistake.
- Treating the CMO as the owner of everything customer-facing. Pricing, product, and support often sit elsewhere and shape the results they are judged on.
- Asking 37 questions when three would do. Pick the ones you can act on, and leave time for the answers.
- Failing to write down the specific numbers you were given, which are the things you can revisit next quarter.