How Senior Executives Actually Find Mentors That Work | Key Search

The standard “find someone a few levels above you” advice breaks down once you’ve run out of rungs
Structured arrangements consistently outperform informal ones, for multiple reasons
There are three distinct types of mentoring relationship worth building, and most executives have none of them
The best time to start is before you need it

The standard mentoring advice doesn’t apply once you’ve run out of rungs.

Identify someone a few levels above you, ask for a coffee, build the relationship over time. That works reasonably well (for some people) on the way up. At the top, the pool of people who’ve faced what you’re currently facing is genuinely small. They’re running their own organisations. They’re not waiting to be found.

What I see instead is executives drifting toward three poor substitutes. Their board, which has governance obligations and its own agenda. Their peer network, which is mostly people in competing positions. Their executive team, where candour is compromised because the relationship is evaluative.

None of them will tell you what you’re getting wrong when the stakes are high enough that everyone else has quietly decided not to.

The time problem comes first

Before the question of who, there’s the question of when.

Most CEOs and senior executives are running flat out. The idea of identifying the right person, finding a way to approach them, framing what you actually need, and then building something that isn’t just another item on an already full calendar, feel near right impossible. And is at the very least easy to defer. And deferral, repeated often enough, becomes the default option.

This is one reason structured programmes outperform informal arrangements at this level. The FTSE 100 Cross-Company Mentoring Programme, founded by Peninah Thomson, has placed approximately 250 senior executives as mentees. 48 subsequently joined FTSE 100 boards or executive committees. The structure removes the activation cost. You don’t have to figure out who to approach or how to frame it. The relationship has a container, and both parties know what they’re committing to. Informal mentoring, however well-intentioned, tends to drift because neither party ever quite prioritised it when it mattered.

Peer advisory groups work for the same reason. The format does the work of keeping the relationship alive. Vistage tracks member company performance against Dun & Bradstreet benchmarks: during COVID, member CEOs grew annual revenue by 4.6% while comparable non-member businesses declined by 4.7%. During the 2008 recession, the gap was fifteen points. Whether you attribute that entirely to the peer group or not, the mechanism is straightforward: a small group of leaders who aren’t competing with each other, meeting regularly, with accumulated trust. Most executives don’t have that outside of a structure that creates it.

The three types worth building

A veteran outside your sector. The instinct is to find someone who’s done exactly what you’re doing. Usually the wrong instinct. Your existing network is already full of people who came up through a similar context. They share your assumptions. They’ll confirm your instincts.

Suzanne de Janasz and Maury Peiperl spent two years studying 45 CEOs with formal mentoring arrangements. Most deliberately crossed industry lines when choosing mentors. Crossing that line was the point.

A peer cohort. Already covered above on the performance data, but worth adding: the longitudinal element is what most people underestimate. An advisory group accumulates shared history. That’s what makes the harder conversations possible. A one-off call with an impressive person you found on LinkedIn typically doesn’t get you there.

A reverse mentor. Most senior leaders haven’t considered this. Jack Welch started it at GE in 1999, pairing 500 executives with younger employees to learn about the internet. PwC, Microsoft, BNY Mellon and others have since built formal programmes around it.

Kaše, Saksida, and Mihelič studied 750 participants in a digital skills programme, published in Human Resource Management in 2019. Younger mentors described the experience as “rare, privileged and hard to replicate.” BNY Mellon tracked 96% retention among the 77 millennials in their programme.

For the senior leader, the value runs deeper than staying up-to-date on technology. Someone who grew up with fundamentally different assumptions will notice things you’ve stopped noticing. That’s typically hard to get from someone who came up the same way you did.

When to do it

Michael Watkins at IMD found that senior leaders go through an average of 13.5 major transitions over an 18-year career. Roughly one every 14 months. These transition points are natural moments to seek outside perspective, when the usual certainty is briefly disrupted. Most executives don’t take advantage of this. The ones who do tend to navigate transitions faster and make fewer mistakes early on.

The other thing I’d say: building a mentoring relationship during a crisis is harder than it looks. The trust that makes difficult conversations useful takes time. You can’t borrow it when something has already gone wrong.

The executives with the most useful mentoring relationships built them long before they needed them. How? By being generous in the moments they had the bandwith. By freely sharing knowledge and building relationship with the people around them.

The uncomfortable bit

Most senior executives allocate more time and resources on how to develop their teams than about how to develop themselves. They commission leadership assessments. They think carefully about coaching budgets and succession planning. Then they make the majority of their own decisions in a largely unreviewed environment, with feedback loops that are long and heavily filtered.

The Consortium for Research on Emotional Intelligence tracked this across more than 1,000 professionals: the higher the rank, the wider the gap between self-assessed and externally assessed leadership performance.

The leaders who are thriving and hard to replace tend to share one thing: they have someone in their corner who will say what nobody inside the organisation will, or see what nobody inside the organisation can. Do you have someone like that in yours?

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