15 Questions to Ask a Fractional CMO (With Red Flag Answers)

Interviewing fractional CMO candidates is tricky. Unlike hiring a junior marketer where you can test specific skills, you're evaluating strategic thinking, leadership ability, and fit with your company—often in just an hour or two of conversation.

The questions you ask matter enormously. Generic questions get generic answers. Strategic questions reveal how candidates actually think and work.

This guide provides 15 essential questions to ask fractional CMO candidates, explains why each question matters, and helps you identify red flag answers that should make you think twice.

Experience and Track Record Questions

Question 1: "Walk me through a marketing strategy you developed from scratch. What was the situation, what did you build, and what results did you achieve?"

Why this matters: You need to know they can create strategy, not just execute someone else's plan. This question reveals their strategic thinking process and whether they can articulate clear outcomes.

What to listen for:

• Structured approach to assessing the situation
• Clear link between insights and strategy choices
• Specific, quantifiable results
• Honest acknowledgment of challenges or failures

Red flag answers:

• Vague results: "We saw significant improvement in brand awareness"
• Taking credit for team wins: "I" statements for everything
• No mention of how success was measured
• Strategy that sounds like tactics (campaigns, not direction)

---

Question 2: "Tell me about a marketing initiative that didn't work. What happened and what did you learn?"

Why this matters: Everyone has failures. How they handle them reveals self-awareness, learning ability, and honesty. Someone who claims no failures is either lying or hasn't taken enough risks.

What to listen for:

• Genuine ownership of the failure
• Clear analysis of what went wrong
• Specific lessons learned and applied
• No blame-shifting to team, budget, or circumstances

Red flag answers:

• "I can't really think of any major failures"
• Blaming others: "The team didn't execute" or "Leadership didn't give enough budget"
• Shallow lessons: "I learned to plan better"
• Defensive body language or tone

---

Question 3: "How do you approach the first 30 days with a new client?"

Why this matters: Their onboarding process reveals how they actually work. A structured approach indicates experience; a vague answer suggests they're winging it.

What to listen for:

• Clear phases (assessment, strategy, execution)
• Emphasis on understanding before acting
• Specific deliverables or milestones
• Stakeholder engagement plan

Red flag answers:

• "I jump right in and start optimizing"
• No mention of learning the business first
• Focus only on tactics, not strategy
• Unable to describe a clear process

---

Strategic Thinking Questions

Question 4: "If you could only use three metrics to measure marketing effectiveness for a company like ours, what would they be and why?"

Why this matters: This reveals whether they understand what actually matters for your business type. A B2B SaaS CMO should talk about different metrics than a consumer brand CMO.

What to listen for:

• Metrics aligned with your business model
• Balance of leading and lagging indicators
• Explanation of why each metric matters
• Follow-up questions about your specific situation

Red flag answers:

• Generic metrics without business context
• Focus only on vanity metrics (followers, impressions)
• Inability to explain how metrics connect to business outcomes
• Rigid answers without asking about your business

---

Question 5: "Our current marketing budget is $X. How would you prioritize spending?"

Why this matters: Budget allocation reveals strategic thinking and priorities. You'll see whether they can work within constraints and make tough tradeoffs.

What to listen for:

• Clarifying questions before answering
• Recognition that priorities depend on your goals
• Willingness to cut things to focus resources
• Understanding of what's realistic at your budget level

Red flag answers:

• Answering without asking about your goals or current state
• Spreading budget across too many channels
• Immediately suggesting you need more budget
• Pet projects pushed regardless of your situation

---

Question 6: "How do you balance brand building with demand generation?"

Why this matters: This is one of marketing's eternal tensions. Their answer reveals marketing philosophy and whether they understand both sides.

What to listen for:

• Acknowledgment that both matter
• Framework for deciding the balance
• Understanding of how company stage affects the balance
• Specific examples from past experience

Red flag answers:

• Dismissing one or the other entirely
• "Brand doesn't matter, only leads count"
• "We don't do demand gen, that's sales' job"
• Inability to articulate how to measure brand impact

---

Working Style Questions

Question 7: "How do you typically structure your time with clients? What does a typical week look like?"

Why this matters: Fractional CMOs juggle multiple clients. You need to understand how much attention you'll actually get and how accessible they'll be.

What to listen for:

• Clear allocation of hours to different activities
• Defined availability and response time expectations
• Honest discussion of other client commitments
• Flexibility to accommodate your needs

Red flag answers:

• Vague: "I'm available whenever you need me"
• Unable to articulate typical time split
• Avoiding questions about other clients
• Over-committing (promising 40 hours when they have multiple clients)

---

Question 8: "How do you handle disagreements with founders or leadership about marketing direction?"

Why this matters: Conflict is inevitable. You need someone who can push back professionally while ultimately supporting decisions.

What to listen for:

• Experience navigating disagreements
• Balance of advocacy and flexibility
• Emphasis on data and evidence
• Ultimate respect for founder's decision-making authority

Red flag answers:

• "I usually just go along with what the founder wants"
• "I'm the expert, they should trust my judgment"
• No examples of successful resolution
• Adversarial framing

---

Question 9: "What's your approach to managing and working with marketing teams or agencies?"

Why this matters: Many fractional CMOs work with existing teams or agencies. Their leadership style needs to fit your situation.

What to listen for:

• Experience with various team structures
• Emphasis on enablement, not just direction
• Ability to work through others, not just do everything themselves
• Track record of developing junior team members

Red flag answers:

• "I prefer to do everything myself"
• Dismissive of agencies or junior team members
• No examples of developing others
• Command-and-control mindset

---

Industry and Functional Questions

Question 10: "What marketing channels or tactics have you seen work best for companies similar to ours?"

Why this matters: Relevant experience accelerates results. Someone who's done it before in your industry brings immediately applicable insights.

What to listen for:

• Specific examples from relevant companies
• Understanding of why certain channels work
• Acknowledgment that results depend on execution
• Honest assessment of their depth in your space

Red flag answers:

• Recommending channels they always recommend
• No relevant experience but claiming universal applicability
• Unable to discuss specifics
• Overpromising results based on other contexts

---

Question 11: "How do you stay current with marketing trends and best practices?"

Why this matters: Marketing evolves rapidly. You need someone who's actively learning, not relying on approaches from five years ago.

What to listen for:

• Specific resources they use (publications, communities, courses)
• Recent examples of learning something new
• Balance of trend-watching and fundamentals
• Healthy skepticism of hype

Red flag answers:

• Unable to name specific resources
• "I've been doing this so long I don't need to keep learning"
• Only follows trends, no grounding in fundamentals
• Dismissive of new platforms or technologies

---

Question 12: "What marketing technology are you most experienced with?"

Why this matters: Marketing runs on technology. Their tech experience indicates whether they can hit the ground running with your stack.

What to listen for:

• Experience with major platforms in their areas of focus
• Understanding of how tools connect and integrate
• Ability to evaluate and implement new tools
• Recognition that tools serve strategy, not vice versa

Red flag answers:

• Limited to one ecosystem or vendor
• Out of date on current tools
• Over-reliance on specific tools
• Unable to articulate how tech serves marketing goals

---

Results and Expectations Questions

Question 13: "What results can we realistically expect from working together, and in what timeframe?"

Why this matters: You need to understand expectations upfront. This question reveals honesty and ability to set realistic expectations.

What to listen for:

• Clarifying questions about your situation
• Realistic timelines (marketing takes time)
• Distinction between quick wins and longer-term results
• Acknowledgment of variables that affect outcomes

Red flag answers:

• Guaranteeing specific results without knowing your situation
• Promising unrealistic timelines ("Double revenue in 90 days")
• No mention of what factors affect success
• Overpromising to close the sale

---

Question 14: "How do you report on progress and results?"

Why this matters: Ongoing communication and accountability are essential. Their reporting approach shows whether they'll keep you informed.

What to listen for:

• Regular cadence and clear format
• Balance of metrics and narrative
• Proactive issue flagging
• Willingness to customize reporting to your needs

Red flag answers:

• Vague: "I'll send updates as needed"
• Resistance to regular reporting
• Metrics-only without context
• Waiting until asked for updates

---

Question 15: "What would you need from us to be successful?"

Why this matters: This shows whether they understand the two-way nature of the engagement. It also surfaces their requirements upfront.

What to listen for:

• Reasonable access and support needs
• Clear communication expectations
• Understanding of typical friction points
• Specific requests tied to their ability to deliver

Red flag answers:

• "Nothing, I'm totally self-sufficient"
• Excessive demands that indicate high maintenance
• Inability to articulate their needs
• Blaming past clients for failed engagements

---

Bonus Questions for Specific Situations

If you're an early-stage startup:

"Tell me about your experience building marketing from zero. What would you do in the first 90 days with no existing marketing infrastructure?"

If you have an existing marketing team:

"How do you work with in-house teams without creating friction? What does the reporting relationship typically look like?"

If you're preparing for fundraising:

"What role have you played in investor communications and fundraising support? Can you share examples of marketing materials you created for fundraising?"

If you're in a regulated industry:

"What experience do you have with compliance and legal review in marketing? How do you balance speed with compliance requirements?"

How to Evaluate Responses

Strong Candidates Will:

• Ask clarifying questions before answering
• Give specific examples, not abstract principles
• Acknowledge nuance and tradeoffs
• Be honest about limitations or gaps
• Demonstrate genuine curiosity about your business
• Connect their experience to your specific needs

Weak Candidates Will:

• Give one-size-fits-all answers
• Speak in generalities without specific examples
• Never admit to failures or limitations
• Focus only on what they've done, not what you need
• Oversell and overpromise
• Avoid direct answers to direct questions

Frequently Asked Questions

How many of these questions should I ask?

For a 60-minute interview, plan to cover 8-10 questions thoroughly, plus time for their questions. Quality of discussion matters more than quantity of questions.

Should I share these questions in advance?

For senior roles like fractional CMO, sharing general topics (but not specific questions) is reasonable. It's not a "gotcha" interview—you want thoughtful responses.

What if their experience doesn't match my industry?

Adjacent experience can be valuable. Focus on transferable skills (strategy development, team leadership, metric types) and assess their ability to learn your industry quickly.

How much should I weigh gut feeling vs. interview performance?

Some excellent CMOs aren't great interviewers. Weight references and past work heavily. But if something feels off, investigate further before proceeding.

Should I involve my team in interviewing?

Yes, especially anyone who will work directly with the CMO. Different perspectives help catch things you might miss, and buy-in from the team matters for success.

Find Your Fractional CMO

Armed with these questions, you're ready to conduct substantive interviews that reveal whether a candidate is truly right for your needs—beyond their polished pitch.

Need help finding candidates to interview? FractionalChiefs maintains a curated network of vetted fractional CMOs. Browse our CMO network or describe your needs and we'll match you with pre-qualified candidates.