Early in my fractional career, I walked into a CEO interview with the mindset of a full-time COO. Strategy, frameworks, org design, the way I’d think about the business if I were the one running it day to day.
He didn’t ask about any of that.
He asked what I’d actually done at my last company that drove the product launch. Not the plan. The specific decision, and why I made it that way instead of the obvious alternative.
I hadn’t prepared for that question. I answered it anyway, because it was the one thing I knew cold: what I’d done, and why I’d done it.
I still don’t know exactly why I got the engagement. I didn’t have the mindset of a fractional executive yet, not really. But looking back, that interview taught me something it took years to fully act on: a CEO doesn’t hire a fractional executive for strategy in isolation. They hire someone who can hold the strategy and still point to what they actually did with it.
I’ve sat on the other side of that table many times since, vetting fractional executives for companies I’m working with. The pattern holds. Ask someone what they did and why, not what they’d recommend, and you find out in about ninety seconds whether you’re talking to an operator or someone who’s very good at sounding like one.
If you’re hiring a fractional COO or CMO, skip the strategy question. Ask what they actually did last time, and why. If the answer is vague, that’s your answer.