The fastest way to tell a hands-on operator from a slide-deck advisor is to ask questions that can only be answered with specifics: what they shipped, which numbers they trust, how they run agencies, and exactly what your fee buys. Below are 25 questions grouped by what each reveals, with strong and weak answers, red flags, reference checks and a weighted scorecard. I sell this service myself, so use every one of them on me too.
How to run the evaluation in two calls
Two calls are enough: one tests depth, the other tests how the candidate thinks about your business.
Call 1 (45 minutes): depth and accountability. Use the hands-on and measurement questions. Ask them to screen-share something they built recently, such as a campaign structure, dashboard or email flow, with client details hidden.
Between calls: send a data pack. Twelve months of revenue and marketing spend by channel, funnel conversion rates, and screenshots or read-only access to your main ad account and analytics.
Call 2 (60 minutes): working session and terms. Spend half on your data: what they would check first, what looks broken, what they would do in week one. Use the rest for team, agency and contract questions.
Four rules keep the comparison fair:
- Ask every candidate the same questions in the same order.
- Score right after each call.
- Bring a second person to at least one call, usually whoever owns sales or finance.
- Follow any general answer with “Can you give me a specific example?” Score the second answer, not the first.
Questions that test hands-on experience
These separate people who run marketing from people who review it.
1. What did you personally build or change in an ad account, CRM or website last month?
- Strong: a specific change, the reason and the result. “I consolidated a client’s prospecting campaigns because budget was spread too thin to exit the learning phase.”
- Weak: “My team handles execution; I focus on strategy.”
2. Walk me through the last campaign you launched, from brief to first optimization.
- Strong: who wrote the brief, which conversion event it optimized for, how creative was chosen, what changed after week one.
- Weak: a story that jumps from “we launched” to “results were great.”
3. Which of our channels would you touch first, and which would you leave alone?
- Strong: a hypothesis with caveats, including something they would not change.
- Weak: everything needs an overhaul, or no hypothesis until you buy an audit.
4. Tell me about a test that failed. What did you do next?
- Strong: the hypothesis, the kill criteria, the decision and where the budget went.
- Weak: no failures, or failures blamed on the client.
5. What would you do yourself in the first two weeks, and what would you delegate?
- Strong: a concrete split. “I’d fix conversion tracking myself and brief your designer on the landing page.”
- Weak: “I’d assess the situation and put together recommendations.”
6. Which tools do you log into every week?
- Strong: a short list tied to real work: GA4, Google Ads, Meta Ads Manager, HubSpot or Klaviyo.
- Weak: only slides, project management and video call tools.
7. Show me something you built. What would you change about it now?
- Strong: shares a screen and explains both the decisions and the flaws.
- Weak: promises to send a case study PDF after the call.
Some fractional CMOs only direct; others build as well, which is how I run fractional CMO and Head of Growth engagements. Neither is wrong, but know which one you are buying.
Questions about measurement and accountability
Someone who can’t reconcile numbers can’t make budget calls.
8. Our ad platforms claim more conversions than our CRM or store shows. How would you handle that?
- Strong: explains attribution windows, view-through credit and double counting, then says which number drives which decision.
- Weak: “We’ll set up proper attribution,” or quoting platform ROAS as fact.
9. Which single metric should we judge you on, and what would you expect it to do in 90 days?
- Strong: one metric tied to revenue (qualified pipeline, new customers or contribution margin) and a range with conditions.
- Weak: traffic and engagement metrics, or a guaranteed number before seeing data.
10. How do you tell whether a channel is actually incremental?
- Strong: holdout or geo tests, controlled pauses, watching blended efficiency, and knowing when a test is too small to read.
- Weak: “The platform’s attribution shows it’s working.”
11. What does your weekly report look like?
- Strong: shows one that leads with the primary metric, then spend and efficiency, then decisions.
- Weak: a dashboard of impressions, clicks and engagement rate.
12. When did you last recommend cutting budget?
- Strong: a specific cut, the reason and where the money went.
- Weak: every recommendation was to spend more.
13. How do clients see what you did each week?
- Strong: a written log of what shipped, what’s next and what’s blocked.
- Weak: “Clients see it in the results.”
Questions about working with your team and agencies
14. How would you brief our paid media agency in week one?
- Strong: a written brief: one target, budget guardrails, reporting format, and what needs approval.
- Weak: “I’d set up a call to get aligned.”
15. Have you ever replaced an agency? How did you decide and hand over?
- Strong: clear criteria, a notice-period plan and a handover list covering account ownership, tracking and creative files.
- Weak: never, or no mention of the handover.
16. How do you work with a founder who wants to approve everything?
- Strong: proposes written decision rights, for example budget moves under an agreed threshold without sign-off.
- Weak: “I’m flexible,” which usually means proposals waiting in your inbox.
17. What would you need from our sales team?
- Strong (B2B): agreed lead stage definitions, closed-lost reasons, pipeline by source and time listening in on sales calls.
- Weak: nothing, or only “faster follow-up on leads.”
18. How would you evaluate our in-house marketers?
- Strong: against clear goals after a few weeks of direction, with honest feedback to you.
- Weak: judging people in week one, or avoiding the question.
19. What stays with us when the engagement ends?
- Strong: playbooks, tracking documentation, reports, and every account owned by your company.
- Weak: vague, or tools and accounts set up under their own business.
Questions about scope, hours and contract terms
20. How many hours a week will we get, and when are you reachable?
- Strong: a number or tight range, fixed meeting days, response times and time-zone overlap.
- Weak: “As much as you need.”
21. What exactly is included, and what costs extra?
- Strong: a written scope: leadership, hands-on work, channels, and whether ad spend, tools and freelancers are extra.
- Weak: scope defined only by the monthly fee.
22. How many other clients do you have right now?
- Strong: a number and how they protect focus.
- Weak: evasion.
23. What are the minimum term and notice period?
- Strong: a short first phase, then monthly, with clear notice terms.
- Weak: a long lock-in before any results.
24. Do you receive referral fees or commissions from agencies or tools you recommend?
- Strong: a clear no, or full written disclosure.
- Weak: hesitation.
25. What would make you tell us this isn’t working?
- Strong: specific conditions. “If you can’t fund execution beyond my fee, or decisions keep stalling, I’ll say so in month one.”
- Weak: “It always works.”
For my own fees, see the pricing page.
Red-flag answers
Any of these should end the conversation or trigger a hard follow-up:
- Guarantees a specific result before seeing your data
- Talks only in frameworks, never tools or numbers
- Wants your ad accounts, domain or tracking set up under their own accounts
- Proposes more spend before anyone has checked the tracking
- The first deliverable is a long strategy document due in six weeks
- Undisclosed commissions from vendors they recommend
Reference-check questions
Ask for two references, one current and one ended engagement, and speak to the founder or CEO.
- What did they ship in the first 30 days?
- How much did they build themselves, and how much did they direct?
- How did they handle a number going the wrong way?
- How many hours did you actually get, and were they reachable when it mattered?
- What did they leave behind: documentation, dashboards, hires?
- Why did the engagement end, or why does it continue?
- Would you hire them again for the same problem?
Compare the answers with what a fractional CMO 90-day plan should deliver.
Candidate scorecard template
Score each criterion 1 to 5, then multiply by the weight. The maximum total is 5.0.
| Criterion | Weight | What a 5 looks like | Questions | Score (1-5) | Weighted |
|---|---|---|---|---|---|
| Hands-on execution | 30% | Showed recent work, clear do-versus-delegate split | 1-7 | ||
| Measurement and accountability | 25% | Reconciles numbers, one agreed metric, has cut budget | 8-13 | ||
| Team and agency leadership | 20% | Written briefs, decision rights, clean handovers | 14-19 | ||
| Scope and terms | 15% | Hours, scope and conflicts in writing | 20-25 | ||
| Working session on your data | 10% | Useful hypotheses from your numbers within 30 minutes | Call 2 |
Adjust the weights: with a strong in-house team that only needs direction, move 10 points from execution to team leadership.
A worked example with made-up scores: candidate A scores 5, 3, 4, 4, 4 for a total of 4.05. Candidate B scores 2, 4, 5, 5, 3 for 3.65. B looks better on process and terms, but A is the one who will ship.
| Weighted total | What it means |
|---|---|
| 4.0 or higher | Strong fit: run references, then agree terms |
| 3.0 to 3.95 | Possible fit: start with a fixed-scope project |
| Below 3.0 | Pass |
A red-flag answer on account ownership, guarantees or commissions is a pass regardless of score.
Get it built
If you want to put me through all 25 questions, book a call and bring your data pack. To test the fit first, start with the fixed-price $1,500 Growth Audit, credited if we continue. See pricing for the options, or get in touch.