Questions to Ask a CMO
For an employee, a vendor, or a peer with time in front of a chief marketing officer. Twenty 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.
The questions
Open any question for the note
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.
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 twenty 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.