Marketing Questions to Ask

The questions

Open any question to see why it works.

1. 1

   Who are you trying to reach, and who have you decided not to chase?

   The exclusion is the harder half and the more revealing one. Any team can describe a target customer; only a team with a real strategy can name the segment it deliberately walks away from. If nobody has been ruled out, budget is almost certainly spread thin across audiences that convert at very different rates.

2. 2

   What is the one number you are held to this year?

   A single answer means the function has priorities. Five answers usually mean the metrics were assembled to make the team look busy, and that whichever number is failing at review time becomes the one that mattered. Ask who set it and whether the team believes it is reachable, since a target nobody believes in produces short-term tactics.

3. 3

   Which channel is working, and how do you know it is the channel rather than something else?

   The second clause separates measurement from belief. Branded search, email to an existing list and retargeting all take credit for demand created elsewhere, and a team that cannot discuss that is probably over-investing in whatever is easiest to attribute. Listen for anyone who has run a holdout or paused a channel to see what happened.

4. 4

   What did you stop doing in the last year, and why?

   Marketing functions accumulate activity, so the ability to name something killed is a sign of discipline. Watch for a stop that was really an abandonment: nobody decided, the person who ran it left. A team that has stopped nothing is running last year's plan plus additions, whatever the strategy document says.

5. 5

   How would you describe what you sell in one sentence, without adjectives?

   Strip out leading, innovative and seamless and either something concrete remains or it does not. Ask two people separately and compare, because divergence at this level explains a great deal of inconsistent messaging downstream. Long answers usually mean the positioning has never been settled, only decorated.

6. 6

   What do customers get wrong about you before they buy?

   Requires the team to have talked to customers rather than to have read a persona document. The common misconceptions are where messaging has the most leverage, and a team that knows them can usually tell you which page or which sales call corrects them. No answer here means nobody is listening to sales calls.

7. 7

   What have you learned from customers recently that changed a decision?

   Insisting on a decision that changed filters out research that was performed and shelved. Good answers are small and specific: a word removed from a headline, a pricing page reordered, a segment dropped. Answers that describe a report with no consequence tell you research here is a ritual.

8. 8

   How do you decide what to make next?

   You are looking for whether a process exists or whether the loudest request wins. Listen for who can put work into the queue: if the answer includes the founder, the sales team and whoever asks most persistently, the strategy is decorative. Also ask what was declined recently and how that was communicated.

9. 9

   Where does the budget actually go, roughly, and what would you cut first?

   The split between media, people, tools and production tells you what kind of function this is, and the cut question reveals what is protected. Someone who would cut the thing they cannot measure is being honest about their evidence, while someone who would cut headcount first may be signalling a team they did not choose.

10. 10

    How long does it take to get from an idea to something a customer can see?

    Cycle time predicts how much the team can learn in a year, and it is rarely tracked. Ask for the last three things shipped and how long each took from first conversation. Long timelines usually trace to approval layers rather than to the work itself, which is worth knowing before you propose more work.

11. 11

    What does the team do itself, and what do you buy in?

    Reveals both capability and dependency. Agencies holding the strategy while the internal team executes is a fragile arrangement, and so is the reverse. Ask what would happen if a particular supplier stopped tomorrow, since the answer often names a single freelancer who holds something important.

12. 12

    Where do you and the sales team disagree, and how does that get settled?

    Every organization with both functions has friction, so a claim of perfect alignment means either the answer is polite or the two teams do not talk. Expect lead quality, pricing or messaging. What matters is whether disagreements resolve in a meeting with data or by whoever has more influence that quarter.

13. 13

    Which report do you genuinely act on?

    Most teams produce far more reporting than they use, and naming the one that drives action shows what is really being managed. If the honest answer is none, the numbers are being assembled for other people's meetings. Ask what decision the report changed most recently.

14. 14

    What does your data not tell you, and how do you work around it?

    An honest answer here is a strong signal, because everyone's attribution is incomplete and only some people will say so. Listen for practical workarounds: asking new customers how they found you, running geographic tests, comparing periods with a channel switched off. Certainty about every number is the worrying answer.

15. 15

    What happens when a campaign underperforms in the first two weeks?

    This exposes the real decision culture. Killing everything early looks decisive and prevents learning anything that takes time to appear; defending everything wastes budget. Ask about a specific recent case, including who made the call and what evidence they had.

16. 16

    How much of your growth comes from customers you already have?

    Teams under acquisition pressure often ignore retention, expansion and referral, which are usually cheaper than new demand. If nobody owns the existing base, that is both a gap and the fastest available improvement. Ask whether anyone is measured on repeat purchase or renewal.

17. 17

    What would you do differently with half the budget?

    Forces a ranking that a normal planning conversation never produces, and the first thing they would protect is their honest view of what works. Someone who says the whole plan would fail has not separated what matters from what is simply habit, which is worth knowing before the next budget cycle does it for them.

18. 18

    What will you not do, even when it would probably work?

    Draws out where judgment and limits sit: claims that cannot be substantiated, tactics that annoy existing customers, discounting that damages pricing, data practices they are not comfortable with. A team with no such line will eventually cause a problem that marketing cannot fix afterwards.

19. 19

    What piece of work are you proudest of, and what did it cost?

    Pairing pride with cost prevents the polished award-entry answer. Some of the best answers are cheap and unglamorous, and hearing someone describe the effort, the internal resistance and what they would change tells you more about how they work than the outcome does.

20. 20

    What would you want fixed before you add anything new?

    The most useful closing question, because it surfaces the constraint the team already knows about: a slow website, a broken handoff to sales, a missing analyst, a positioning argument nobody has settled. If the answer is nothing, either the function is unusually healthy or the person is telling you what they think you want.