A few weeks ago, on a Teams call regarding a large portfolio I'd been brought in to help stabilize, someone referenced a process everybody was treating as settled. I asked a couple of questions that weren't clever: how does this actually work? What's the business logic behind this particular step? I'm not afraid to ask the stupid question (I mean that literally, not trying to be humble). Most people are afraid to do that - they'd rather nod along than be the one who admits something isn't obvious to them. But I missed the memo on that one, so I just go ahead and ask. And nobody in that meeting had a clean answer.
The Operator Vacuum != A Power Grab
The obvious question is whether letting a gap pull you in like that creates a slippery slope toward a power grab. Here's what this actually looks like on the ground.
At an early-stage vehicle marketplace, I was hired as a project manager. I got there and found what you might expect from a company that young: no real thesis, barely a roadmap, a prototype further along than the thinking behind it, and a tech lead already on the way out with a replacement who hadn't started yet. The CEO was sharp but green, and his instinct when something feels unmanaged was the instinct a lot of first-time founders have: hire someone tactical. Except there wasn't enough of a defined project yet to actually manage, so I started asking the same kind of "stupid" questions I'd ask years later on that Teams call. What's the actual plan here. Who owns this decision. What happens after this ships.
Over the next several months, one gap led to the next: the roadmap that didn't exist, then the process to build one, then the people to run it, then the daily operational load nobody else had the capacity to absorb.
By the time it settled, I was covering the operation end to end, with a title of Fractional CPO. And the CEO got to spend those months doing what he actually needed to be doing: working with the board on strategy.
At an ecommerce company, I was hired for one month, specifically for a holiday conversion campaign. That project was genuinely self-contained. But what I noticed and flagged during that one month, mostly about gaps around the campaign rather than inside it, is what got me invited to stay. The CTO had been trying to hold the operator seat himself on top of his actual job, the way a lot of technical leaders do when nobody else is doing it.
I filled it properly instead: a CMS overhaul, installing real experimentation practice, running the search for a permanent product director. He got to go back to being a CTO (and finally take a breath) instead of burning the candle at both ends.
That's what I mean by the Operator Vacuum: not scope creep, not me angling for more territory, just a gap nobody else was positioned to see. Once you see it, you either say something or you don't. I keep saying something.
Different companies, different industries, same shape. But none of this makes me the captain. I remain the first officer, spending months making sure the captain's thinking actually made it into what happened day to day, so they could spend their time on the part of the job only they could do. That's the actual function: right hand, not replacement, channeling their strategy into what ships.
The Tell
If you're trying to work out whether someone is actually driving from the Operator Seat, or just sitting in it, here's a question that tends to answer it fast: when was the last time they told you something you didn't want to hear, and did the working relationship survive it?
If the honest answer is never, you don't have someone managing your outcome. You have someone managing your feelings.
That question is the closest thing to a shortcut I've got. It won't fully derisk this for you; hiring always requires some leap. But if you're evaluating me specifically, I've done this enough times to know the shape it takes: the person who brought me in ends up with more of their actual job back, not less.