How to hire a Special Operations veteran into an executive role, and five ways companies get it wrong

Most of these hires that fail do not fail at the interview. They fail eight to fourteen months in, and when you take them apart the cause is almost never the candidate’s capability. It is a decision the company made before the person started.

Five failure modes, in rough order of how often we see them.

One: hiring for the story

The background is genuinely impressive. That is the problem.

A panel that has spent an hour listening to somebody describe a career most people cannot imagine comes out energized, and the energy gets recorded as fit. Nobody writes down “we liked the narrative”; they write down “strong leadership presence.” Two quarters later the company has an impressive person in a seat that needed a specific operating skill they were never asked about.

The test: can you say, in one sentence that does not mention the military, why this person beats the other finalist for this job? If you cannot, you have not finished interviewing. That sentence is available for good candidates — “she has run a multi-site finance function at this scale and closed the books through an ERP migration” — and it is conspicuously unavailable for the ones you like for the wrong reasons.

Two: a seat with responsibility and no decision rights

The most common structural error, and the most expensive, because it destroys good hires rather than surfacing bad ones.

This population has spent fifteen or twenty years being trusted to decide with incomplete information and being held accountable for it. Put them in a role that owns an outcome but has to route every real decision through a committee, and they will not complain about it. They will work the problem, conclude the organization does not actually want the thing it hired them for, and leave inside a year — usually with a polite explanation that tells you nothing.

The test, before you post the role: what are three decisions this person can make on their own, and what is the largest dollar amount they can commit without asking? If the honest answer is “they would run everything past the founder first,” you are hiring an analyst and describing a VP.

This is worth doing even if the answer is uncomfortable. A candidate told “your authority is bounded here and here” will make an informed choice. A candidate who discovers it in month three will make a different one.

Three: pricing the offer against the wrong reference

Two mistakes pull in opposite directions and both lose the candidate.

Underpricing, because a military pension is visible and somebody reasons it reduces what the person needs. It does not reduce what the role is worth, it is frequently the compensation for a twenty-year career rather than a subsidy for this one, and a candidate who works out that the offer was built on that reasoning does not come back. It also poisons the reference: this is a community that talks.

Overpricing on the wrong axis, usually a title. Companies sometimes reach for a bigger title in place of money, and a title without the authority in failure mode two is the worst of both.

The test: price the role. Then ask whether you would make the same offer to a candidate with an identical commercial record and no military background. If not, work out which direction you moved and why.

Four: onboarding that assumes they will ask for help

They will not ask. Not from pride — from a professional norm in which figuring it out is the job and escalating a problem you have not tried to solve is a failure of initiative.

So the standard onboarding, which is a week of orientation followed by an open door, produces somebody who is three months in, has quietly built their own mental model of a business they do not yet understand, and has not told anybody which parts they are unsure about.

What works instead is specific and slightly unusual:

• Assign a peer, not a mentor. Somebody at their level who is required to have a weekly conversation. The requirement matters — an optional one does not get used.
• Name the things they are not expected to know yet. “You will not understand our commercial terms with the top five customers for two months, and that is expected” gives permission that an open door does not.
• Ask for a thirty-day read-out on what is broken. They will have noticed things. Asking in a structured way stops it arriving as a surprise in month six, and it uses the thing this hire is genuinely best at.
• Tell them the political map. Which relationships are load-bearing, who has history with whom. They will otherwise find out by walking into it.

We stay engaged after the start date for exactly this period, and it is the part of the engagement clients use least and benefit from most.

Five: the first ninety days problem in reverse

The failure mode nobody warns about: the hire is too effective, too early.

An operator arriving in a mediocre process will fix it. Correctly, quickly, and often before the organization has agreed the process was broken. The fix is right and the sequencing is wrong, and what gets remembered is that the new person went around three people in their second month.

What to do: say it out loud in week one. “In your first sixty days I want you to find the problems and not solve them yet.” Most will find this counterintuitive and all of them will comply, because a clearly stated intent is the thing this population is best at executing. Then in week nine, when you ask what they found, you get the list and the organization’s buy-in to act on it.

The best question in the interview for this is what they did in their first ninety days of their first civilian job. Somebody who has already made this mistake once has usually learned it.

What a good process looks like

Short version, because the five above are the substance:

Screen on the commercial record, not the service record. The service record tells you about character under load. The commercial record is what predicts the next eighteen months, and it is the one a hiring manager can actually evaluate.

Put them in front of people who will work with them, not just the panel. This population reads rooms extremely well and will tell you things after meeting the team that they would not say to a panel.

Check references properly, and ask the awkward question. “Where did they struggle?” is worth more than any other reference question, and in this community you frequently get a straight answer, because the referee is also from a culture where a useless reference is a disservice to everyone.

Decide quickly. Not because of competition, though there is some. Because a drawn-out process with unexplained gaps reads, to somebody used to clear decisions, as an organization that cannot make them — and that impression is hard to reverse.

If you are working a role like this and want a second read on a shortlist, tell us the role. We would rather tell you a candidate is wrong for the seat than place them into one of the five above.