What Questions Should I Ask When Interviewing a Fractional Executive?
Interviewing a fractional executive? Don’t just check for skills—look for mindset, leadership style, and cultural fit. This guide shares key questions to ask, and why the right exec should reflect your vision for the future.
Hiring a fractional executive isn’t just about filling a gap—it’s about inviting someone into your inner circle. The right questions help you uncover not just what they’ve done, but how they think, how they lead, and whether they’ll move your company in the right direction.
Yes, technical skills matter. But they’re not enough. Some execs chase short-term wins and quarterly KPIs. Others build durable systems, grow people, and leave your business stronger than they found it. You need to know which type you’re talking to.
Here’s how to ask—and listen—for what really matters.
🔍 Start with the basics: scope and skill
These establish whether the person can technically do the job.
- What type of companies have you worked with that are similar to ours?Look for stage, size, and industry relevance—not just logos.
- What was your role in that engagement—and what changed while you were there?You’re looking for outcomes and ownership, not fluff.
- What kind of systems or frameworks do you usually bring in?Great execs have playbooks. They’ll also know when not to use them.
- How quickly can you start, and what does your availability look like week to week?Make sure their bandwidth and responsiveness fit your team’s rhythm.
🧠 Then go deeper: mindset and leadership
This is where the real signal lies.
- What part of your work gives you energy?Someone who talks only about deliverables may lack leadership depth. Someone who lights up about people or systems that last often has better long-term impact.
- What would your past clients say you’re best at—and where do you tend to push them most?This tests self-awareness and reveals how they challenge teams.
- What kind of companies or leadership styles do you not work well with?If they say “I work with everyone,” be cautious. Great execs know where they fit—and where they don’t.
- How do you handle disagreements with founders or CEOs?You’re hiring a sparring partner. Make sure they know how to disagree with clarity and care.
🤝 Finally: cultural and strategic alignment
This part often gets skipped—and it’s the most important.
- What’s your long-term view on leadership in small and mid-sized companies?Do they believe in coaching people up, or replacing them? Are they chasing exits, or building resilience?
- What do you want to leave behind when your engagement ends?Great fractional execs think beyond their own timeline. They’ll talk about systems, habits, culture, and confidence—not just metrics.
Why this matters
Some fractional execs are laser-focused on process. Others on people. Some drive short-term growth at all costs, even if it means the team burns out six months later.
That’s why cultural alignment and shared vision matter as much as skill. You’re not hiring a contractor. You’re hiring a temporary version of what leadership looks like in your company.
Make sure they reflect the future you want to build.
My personal take
I’ve worked in growth roles across consumer brands, retail, and luxury goods. But the work I’m proudest of? Helping teams become stronger after I leave.
I believe fractional work isn’t about doing more with less. It’s about doing better—with focus, clarity, and trust. That only happens when the client and exec share values—not just goals.
So if we’re talking about working together, I’ll ask just as many questions of you. Not to qualify the deal—but to make sure we both believe in where we’re going.
Written by Remco Livain
Fractional CMO & Growth Leader | Focused on Long-Term Impact, Not Quick Wins
