The Corporate Alumni Trap - Why the Obvious Hire Often Isn't

There's a specific kind of hire that goes wrong in predictable ways. And it happens often enough in mid-market businesses that I've stopped being surprised by it.

The scenario is familiar: a growing business reaches the point where it needs a serious technology leader. The board looks for reassurance - and reassurance usually arrives in the form of a familiar logo. A CV with fifteen years at a FTSE 100 bank, or a global manufacturer, or a well-known retailer lands on the table. The thinking is: this person has operated at scale, they know what good looks like, they'll bring grown-up discipline to a business that needs it.

Twelve months later, it hasn't worked and the appointment is being unwound. And almost nobody goes back and asks the right question about why.

The question isn't whether the person was capable. They usually are - often highly so. The question is whether the job they did before actually maps onto the job they're being asked to do now. And more often than people realise, it doesn’t.

I was reminded of this recently in a conversation with someone close to a building society's executive team. Their observation: the C-suite had been deliberately built from senior managers and directors at large high-street banks. The logic made sense on paper - these were people who understood what good looked like at scale, brought in at the right level for a smaller institution.

Yet, in practice, several of them were struggling. The specific complexities of a building society - the member-owned governance, the different regulatory posture, the smaller resource pool, the pace of decision-making - had been systematically underestimated.

This isn't an argument against hiring from large corporates. It's an argument for being honest about what a CV actually tells you, and what it doesn't. And it’s an argument for understanding what Boris Groysberg calls the portability of talent.

Groysberg's research at Harvard Business School - published as his book, Chasing Stars - found that star performers who switched firms saw their performance meaningfully decline after the move. The factors weren't about individual capability. They were about context: the systems, colleagues, and relationships the star had built their success within. Often the star was inseparable from the setting.

And this principle cuts the other way too. There's a reverse snobbery I hear regularly from scale-up and PE-backed CEOs: "we don't want anyone from [insert corporate] - they sit in ivory towers, and have every resource in the world handed to them." Sometimes that's fair and often I’m the one making that argument.

But the best corporate operators have handled complexity that simply doesn't exist anywhere else - standing up a new bank in a region with no precedent, navigating regulation across multiple jurisdictions, running a programme with a budget that would buy the whole scale-up three times over. To discount an entire candidate pool based on a logo, is its own kind of mistake.

So if the logo isn't the answer, what is?

The honest response is that you're looking for evidence of portability. Signs that a candidate has already made the leap between two very different operating contexts, or is capable of making it. That's harder to read from a CV than a brand name. But, in my experience, it shows up in three specific places if you ask the right questions.

The first is in the word "hands-on." It's probably the most abused phrase in executive search, because everyone uses it and almost nobody defines it. In a FTSE 100 function, hands-on might mean chairing a weekly delivery council and personally reviewing architecture decisions. In a PE-backed mid-market business, it could mean jumping on a plane to sit with the engineering team in Munich for three days to understand why the integration is slipping. Both are legitimate. They are not the same job. Qualify what hands-on actually means to the candidate you’re interviewing.

The second is in how a candidate talks about teams they've inherited. This is one of the more revealing conversations you can have with a leader. What did they do in the first three to six months with the people who were already there? In practice, answers sit on a continuum - from working with who's on the bus at one end, to rebuilding the function at the other. Neither end is universally right, but a candidate whose answer is the same regardless of context should make you pause.

The third is in the relationship between governance and pace. It’s one thing aiming for grown-up process and operational discipline. It’s another thing applying ITIL, TOGAF, or a Gartner framework to the letter of the law. I’ve seen it grind businesses to a halt. The leaders who succeed in these environments hold a different relationship with governance. They see it as an enabler of scale and resilience, not as an end in itself. They know which frameworks to apply fully, which to apply lightly, and which to leave on the shelf until the business has earned the right to worry about them.

None of these three tests require the candidate to have worked at a company that looks like yours. But no single alumni pool comes with a guarantee either.

Which brings us back to the appointment being unwound twelve months in.

Hiring teams generally feel like they’ve been thorough. The CV was strong. The interview went well. The references checked out. The PE-firm was onboard. By every conventional measure, this was a good hire. But nobody ever really got under the skin of portability.

And sadly the cost of getting this wrong is rarely just the twelve months and the pay off. It's the eighteen months of drift before and after - the decisions that didn't get made, the team that lost momentum, the programme that slipped a year. By the time the appointment is unwound, the real damage is already done.

It's worth the extra week or two at the front of a search to ask the right questions, and to ask them properly.