It’s a figure that’s stuck with me for years, one of those uncomfortable truths that data sometimes throws in your face. When we look at bringing in senior leaders from outside, folks who are meant to slot into relatively significant roles, the success rate hovers around 50/50. Fifty-fifty. Think about that. You’re essentially flipping a coin on whether a key leadership hire will truly take root and flourish. Now, I’m not one for hyperbole, but those aren’t odds that inspire a great deal of confidence if you’re trying to build something for the long haul. It’s led me to think that perhaps we’re often better off acting more like patient gardeners than frantic shoppers in the talent market, a conclusion that AI-powered hiring tools, which make external sourcing faster and cheaper, have done little to alter.

I've spent a good chunk of my life in and around software businesses, coaching dozens of Business Units, and I've seen this play out time and again. We’d get excited about a "star" candidate, someone with a glittering CV from a big, recognisable name in the industry. They’d interview like a dream, full of talk about “transformational strategies” and “leveraging synergies.” We’d bring them in, often at considerable expense, to head up a division or a key initiative. And then, more often than you’d like, things would start to go sideways.

Six months, maybe a year down the line, you’d find morale dipping. Good, solid people who understood the nuts and bolts of our particular niche might start looking elsewhere. The promised transformation? It often looked more like confusion. The numbers, which were meant to soar, would often stagnate or even decline. What went wrong? More often than not, the transplant simply didn't take to the new soil.

Our company culture, like that of many successful long-term enterprises, is a peculiar ecosystem. It’s evolved over decades, shaped by a philosophy of decentralisation, autonomy for our Business Unit managers, and a relentless focus on profitable, sustainable growth in often unglamorous vertical markets. We expect our leaders to be deeply embedded in their businesses, to understand the customers, the quirky economics, and the people. They need to be comfortable with a high degree of independence and accountability, often without the vast central resources or hierarchical command structures they might have been used to elsewhere.

The "star" from outside, for all their brilliance, often struggled with this. They were used to a different kind of gardening: perhaps one with richer soil, more fertiliser, or a more regimented layout. They might try to implement the playbook that worked wonders in their last role, only to find it sputtering here. It’s not necessarily their fault, nor ours. It's simply that a plant evolved for one climate and soil type can't always thrive when abruptly moved to another. Interviews, no matter how rigorous, can only tell you so much. AI-powered assessment tools, for all their analytical sophistication, have not, in my view, fundamentally changed this. Past performance is a data point, not a guarantee, especially when the underlying system changes.

Growing from Within

Contrast this with the individuals we’ve cultivated from within. I’m thinking of someone, let’s call her Donna. She might have joined one of our Business Units as an analyst, or perhaps came in with a small acquisition. She was bright, certainly, but more importantly, she was curious and willing to learn. She asked questions. She listened. Her manager, a good gardener themselves, spotted that potential and gave her a small patch to tend: a project, a new responsibility. She made mistakes, of course. We all do. That’s part of how roots grow stronger.

Over years, not months, Donna grew. She learned our businesses from the ground up. She understood the customers not as abstract market segments but as real people with real problems our software helped solve. She absorbed the culture, the unwritten rules, the way we make decisions. When the time came for her to lead a Business Unit, and later a portfolio of them, she wasn't a transplant. She was a mature plant, perfectly adapted to our soil, with a root system that ran deep into the organization. She didn't need a manual on how we operate; she was how we operate. The "long runway" we provided allowed her to reach her potential, and in turn, she made our garden more productive.

She wasn't a transplant. She was a mature plant, perfectly adapted to our soil, with a root system that ran deep into the organization.

I think about this whenever I see another AI-powered recruitment platform claiming to eliminate bias from hiring decisions or to surface the ideal candidate from a global pool of applicants. These tools are genuinely impressive at what they do: screening CVs at scale, identifying credential matches, perhaps even predicting performance against certain measurable benchmarks. But the quality Donna brought (a particular kind of rootedness, a deep absorption of institutional culture, an understanding of the unwritten rules of how we operate) cannot be derived from any external candidate pool, however algorithmically well-curated. You can recruit for skills; you can recruit for track record. You cannot recruit for the decade of accumulated, context-specific judgment that comes from simply having been there. AI-powered hiring tools make external recruitment faster and cheaper. My experience, and that 50/50 success rate, suggests that faster and cheaper is not always what the situation actually requires.

When to Look Outside

Now, I'm a practical sort. I know that sometimes you do need to bring in expertise from outside. If you need a specialist in a cutting-edge technology or a very specific financial domain, and you don't have that skill internally, then looking externally makes sense. A new plant, carefully chosen for a specific purpose and integrated thoughtfully, can sometimes enrich the garden.

But for core leadership, for the people who will manage our Business Units and make the critical day-to-day decisions, my strong bias is towards those who’ve grown with us. They possess an institutional knowledge that’s incredibly hard to replicate or acquire quickly. They understand the "why" behind our methods, not just the "what." This fosters a level of loyalty and deep business understanding that is, frankly, invaluable. They are also more likely to be the kind of leaders who, in turn, become good gardeners themselves, spotting and nurturing the next generation.