Boards spend weeks diligencing a company’s financials before an acquisition and twenty minutes diligencing the operator they’re about to hire to run it. That imbalance is backwards, and it is fixable with better questions.
Boards routinely spend weeks on financial diligence before an acquisition and a fraction of that time diligencing the operator they are about to hire to run the thing they just bought. That imbalance is backwards. The operator’s judgment will shape the financials for years after the deal closes. Most search processes still test for responsibility — did this candidate meet the duties of their prior roles — rather than accountability, and the interview format itself rewards responsible-sounding answers because that is the register most executive candidates have been trained their whole careers to speak in.
Three questions that actually test for it
First: ask for a specific enforcement decision they made that cost something real — a relationship, a timeline, someone’s role. Then listen for whether they distance themselves from the cost as they describe it, or own it plainly as part of the story. A candidate who can only describe enforcement decisions that turned out clean and easy has probably never enforced anything that actually mattered.
Second: ask what they do when a metric has looked clean for an unusually long time. Do they take the clean result at face value, or do they go looking for what the metric might have stopped measuring? I once inherited a self-assessment that had produced zero failures for years — not because the underlying standard was being met, but because the test itself had quietly stopped testing anything real. I reinstated a version of it that the organization could not prepare for in advance. The candidates worth hiring are the ones who, unprompted, describe a version of that same instinct from their own experience: distrust of an unexplained clean run, not comfort with one.
Third: ask them, without prompting, what they would personally check in their first thirty days in the seat. A candidate with a real operating standard already knows the specific answer to this. A candidate without one will describe a listening tour, a strategy review, or a culture assessment — all reasonable-sounding, all a version of telling you what a good new leader is supposed to say, none of it a specific test they intend to actually run.
What the wrong answers sound like
On the first question, the wrong answer names the cost as something that happened to the organization, not something the candidate did — “we had to make some difficult changes” rather than “I made this specific call and here is exactly what it cost.” On the second, the wrong answer treats a long clean streak as validation rather than as a question — “the numbers speak for themselves” is precisely the sentence that should make a board slow down, not relax. On the third, the wrong answer is fluent, reasonable, and entirely generic — it would work for any company in any industry, which is exactly how you know it isn’t specific to this one.
Why this matters more at the top
The higher the seat, the less anyone above the candidate is actually positioned to test their claims after the fact. A board that hires a divisional CEO or an operating partner is, in a real sense, running its last rigorous test of that person’s instincts before those instincts become the organization’s only check on itself. Get the diligence right here, and the organization inherits a leader who tests their own results. Get it wrong, and the organization inherits a leader who tells the board what the board wants to hear — competently, confidently, and for exactly as long as it takes for that to become expensive.
Trust what’s tested. Not what’s told — including, and especially, in the room where you are deciding who to trust with the rest of the organization’s judgment.
Scott Pleus is an operating executive who has built his career on a single conviction: an organization’s confidence in its own readiness is only as good as the last time someone actually tested it. If nobody told you your numbers were good, would you still believe them? That conviction was forged over three decades of command in the United States Air Force, retiring as a Lieutenant General and the longest-serving Acting Vice Chief of Staff in the role’s 79-year history. His command experience is the civilian equivalent of running large, high-consequence operations at every level of scale — from a single division, to a joint international operation, to the number-two position in a 680,000-person global organization. In every one of those roles, the product was readiness, and there was no such thing as a plausible excuse for being wrong about it. His standard, in his own words: accountable, not responsible. That is the experience most executive backgrounds don’t have, and it is what any organization needs when it wants to know — not hope — that it can perform under pressure. Early in his career, he noticed something worth learning from: a self-assessment that had never once produced a failure. Rather than take that as good news, he treated it as a signal that the test itself needed to evolve. He built a new version of the check — one that measured real readiness instead of rehearsed readiness — and kept refining it, even when the organization pushed back, because he was committed to the standard underneath it, not just the version of it that was easiest to pass. That same instinct shaped how he led. He made a habit of showing up unannounced, not to catch anyone, but to see the organization as it actually ran day to day — and to ask the one question a prepared briefing never answers. That habit paid off when he inherited a struggling unit: he gave its two senior leaders a clear deadline and clear ownership of the turnaround, and in sixty days, the unit had rebuilt the standard for itself. The stakes in his operating environment left no room for a wrong answer — there was no version of a readiness failure that was merely inconvenient. That is precisely why the discipline transfers: an executive who has enforced a verification standard with zero margin for error brings a rigor to operating risk that most executive backgrounds never have to develop. Trust what’s tested. Not what’s told.
