"We need a CEO who's scaled a SaaS business from £10 million to £50 million before," the PE partner insisted. "Someone who's been there, done that."
"So you want someone willing to do the same job twice?" I asked.
He looked puzzled. "What's wrong with proven experience?"
"High-performing CEOs don't repeat jobs - they take on bigger challenges. The ones responding to your 'been there, done that' requirement? They're often the ones who struggled the first time."
I learned this lesson the hard way, running restaurants. We hired an ex-PizzaExpress GM to run our site. On paper, perfect experience. In reality? Complete failure. He couldn't market an unknown brand, relied entirely on PizzaExpress's systems, and was unable to adapt to our different context.
Stanford's James G.March captured this paradox perfectly: "On the one hand, experience is described as the best teacher. On the other hand, experience is described as the teacher of fools." The difference lies in whether experience creates just horizontal expertise (more skills and techniques) and also vertical sophistication (the cognitive ability to synthesise, adapt, and apply that knowledge in entirely new ways).
March’s point was that experience only helps if it deepens how you think, not just what you know.
Roger Kneebone frames the same distinction through the progression from apprentice to journeyman to master. Apprentices copy, journeymen repeat, but masters adapt, teach, and lead. PE-backed CEOs need to be masters, not journeymen recycling old playbooks.
Why Experience is an Imperfect Teacher
March identified four fundamental reasons why experience systematically misleads us:
First, history is complex. We create simple cause-and-effect stories from what are intricate, intertwined factors. My PizzaExpress GM attributed his past success to "strong operational discipline", when it was actually the result of established brand recognition, refined corporate systems, and proven market positioning working together.
Second, history is subject to stochastic uncertainty. Experience contains weak signals embedded in substantial noise, making it nearly impossible to distinguish meaningful patterns from random fluctuations. Was his restaurant's performance due to his management or favourable market conditions? The signal-to-noise ratio was impossible to determine.
Third, endogeneity and adaptation. Our actions change the environment itself. The GM's "proven" marketing tactics had trained competitors to respond, making those same tactics less effective in new contexts. What worked once might fail precisely because it worked before.
Fourth, a constructed and limited history. We build narratives from small samples shaped by subjective interpretation. One successful restaurant scaling doesn't constitute a reliable pattern; it's a sample size of one, filtered through a personal perspective.
The fundamental distinction is between horizontal learning (skills and techniques) and vertical development (evolving how we think and make sense of complexity). Most "experienced" candidates have accumulated horizontal learning within familiar contexts. However, PE-backed CEOs require vertical development: the ability to navigate unprecedented challenges and ambiguous environments where their existing playbooks are ineffective.
This is where Kneebone’s metaphor of “crossing the ha‑ha” becomes so powerful. A ha-ha is a hidden ditch in a landscaped garden, invisible until you’re upon it. From the perspective of the journeyman — the expert with deep horizontal experience — the new challenge looks like familiar, smooth grass. They don't see the hidden drop. But navigating today's complex environments requires vertical development. Hiring for experience is a bet that the old playbook is sufficient, assuming the candidate can simply stroll across. Hiring for attributes, however, is a search for a leader with the developmental agility to navigate the unforeseen gap when that playbook inevitably fails.
The High-Performing CEO Paradox
After coaching over 30 CEOs, I've observed that the highest performers rarely face similar scaling challenges. They get promoted to bigger, more complex businesses. They're recruited for step-up opportunities, not lateral moves. They seek new mountains to climb because they understand what March revealed: experience generates confidence more reliably than it creates competence.
The filter effect of "exact experience" requirements attracts CEOs who couldn't advance beyond similar-stage companies, misses those building category-defining businesses, and creates false confidence that "they've done it before" equals "they can do it here."
But here's the crucial insight: the breakthrough CEOs often come from adjacent contexts - different industries but similar scale, the same industry but at a different stage, or a smaller company with a bigger responsibility leap. Why? Because they've developed the vertical capacity to think differently about problems, not just horizontal skills in executing familiar solutions.
The CEO who scaled three identical businesses using the same playbook demonstrates horizontal expertise. The CEO who took a £2 million company to £25 million in an entirely new market demonstrates vertical development — the developmental muscles that matter when facing unprecedented challenges.
And as Kneebone stresses, true experts never believe they’ve arrived. They’re restless, dissatisfied, and constantly aware of how much further they have to go. That’s the mindset PE firms should be screening for: the CEO who treats expertise as a journey, not a finished state.
The Attribute Assessment Framework
This is why Graham Weaver at Alpine Investors (a top-performing US PE house) urges: hire for attributes, train for skills. Experience still matters but on its own, it is not sufficient. In PE-backed environments, experience provides valuable context and confidence; yet, it is attributes that determine whether a leader can adapt, learn, and succeed in a volatile, uncertain, complex and ambiguous (VUCA) environment. That balance shapes the framework I use when assessing CEOs.
What does vertical development capacity actually look like? In my experience, it reveals nine foundational attributes for a CEO that serve as "Gate 1" screening criteria—the table stakes before assessing specific PE competencies.
These attributes aren't 'nice-to-haves'; they are the predictive indicators of a leader's developmental capacity to operate under the specific pressures of a PE-backed environment, organised across three tiers:
Tier 1: The Foundational Character - INTEGRITY, HUMILITY, RADICAL RESPONSIBILITY.
Tier 2: The Inner Engine - HUNGER, RESILIENCE, INTELLECTUAL HORSEPOWER, CURIOSITY.
Tier 3: The Applied Abilities - PEOPLE SMARTS, LEADERSHIP.
A humble, hungry, curious CEO with radical responsibility will develop the sophistication to figure out SaaS scaling, even without sector experience. An experienced but incurious CEO lacking intellectual horsepower will apply outdated mental models to new situations, no matter how impressive their CV appears.
To assess this vertical development, I use what I call 'career archaeology', questions that reveal how someone has grown from their experiences:
"Tell me about your biggest professional failure and how it changed your thinking"
"Describe a time you succeeded in something you'd never done before"
"What's the steepest learning curve you've navigated, and how did it change your approach?"
Look for evidence of personal growth and developmental maturity, not just skill accumulation. The fundamental challenges of leadership — building teams, making decisions under uncertainty, and driving execution — require vertical development that transfers across any context.
This is what educational psychologist Lev Vygotsky called the “zone of proximal development” — the space where someone can stretch into new capability with support. Attributes, not experience, signal whether a leader can make that stretch.
From Hiring Framework to Development Playbook
Hiring for attributes isn't just about making better selections; it's about enabling faster and more effective development post-hire. When you hire a leader who demonstrates humility and curiosity, you've hired someone coachable. The board or PE firm can then step into the role of the "master," guiding their new CEO.
Kneebone's work provides the playbook:
Mind the "Ha-Ha": The board must recognise the invisible gap between their expert knowledge and the new CEO's initial perspective. They must translate their expertise rather than expect it to be understood.
Provide "Scaffolding": A skilful board provides temporary support and guidance in the CEO's "zone of proximal development" - the area where they can succeed with expert help.
Know What Not to Point Out: An effective board, like a master teacher, resists the urge to swamp a new leader with an endless list of improvements, focusing instead on the vital few issues that will unlock the next level of performance.
This approach turns a high-potential hire into a high-performing leader far more effectively than hiring an experienced journeyman who is resistant to new learning.
The Value Creation Imperative
As March's research reveals, "Experience is likely to generate confidence more reliably than it generates competence and to stop experimentation too soon."
This is the hidden danger of experience-based hiring — it creates a false certainty that kills the very experimentation and adaptation that uncover the non-obvious growth levers your Value Creation Plan depends on. It invites a CEO to default to their old playbook while your hold period extends and your IRR decays.
While your competitors fight over the same "experienced" talent pool, you can hire for the developmental sophistication that drives the step-change in value that separates a good investment from a top-quartile return. The most dangerous candidate has extensive experience but limited personal growth. The most promising have strong attributes and know how to treat their past as data, not doctrine.
As Kneebone puts it, expertise is like rowing against a current: stop moving and you drift backwards. The best CEOs understand this and build organisations that learn as relentlessly as they do.
And that’s the ultimate lesson: “been there, done that” is a false comfort. The CEOs who will create real value for your portfolio are not the ones repeating yesterday’s job — they are the ones capable of mastering tomorrow’s challenges.
Mark Farrer-Brown, a former top-decile PE partner turned CEO mentor, created the FOCUS methodology to bring investor-grade discipline to hiring — a system designed to consistently identify A-Player leaders who drive alpha.