The board thought they had found the perfect CEO. Two successful exits. A scaled multinational division. References that read like a character witness: decisive, commercially sharp, a natural leader. In the interview he was confident, fluent, convincing on growth and culture and transformation. The appointment was unanimous. Twelve months later the same board was negotiating his exit. Revenue targets had been missed.
There’s one question almost every HR-led interview process insists on. “Tell me about a time you failed.” At junior level, it sometimes earns its keep. At C-suite, it’s a junk question. And it’s almost always the wrong thing to ask in the room. I’ll explain why I won’t ask it. And then I’ll tell you what I ask instead.
Most succession planning assumes someone is ready to step up. But what happens when the obvious successor is the one who leaves? A look at why heir apparent plans fail, the real cost of an unplanned leadership transition, and how boards build genuine continuity.
I was briefing a candidate last week. On paper, exceptional. A consulting career at one of the global firms, then a move into a chief of staff role at the global level, leading strategy and go-to-market across multiple regions. The kind of profile that makes you sit up.
Some companies are so successful that they never have to be brilliant. Think about the organisations that dominate their markets so completely that urgency simply does not exist. The revenue keeps coming. The brand carries weight. The infrastructure is established. And somewhere inside that comfort, the standard of leadership quietly settles into something unremarkable.
Succession planning too often rewards visibility over viability. The squeaky wheel gets noticed, but the quiet engine actually keeps the organisation moving. In many businesses, the squeaky wheel ends up on the succession plan simply because it is easier to see. That shortcut is getting riskier. With employers expecting nearly 40% of workers’ core skills to change by 2030, the signals we use to identify future leaders need to change as well.
I interviewed someone this week who has spent 31 years at the same organisation Fast tracked early in his career. Senior roles. MBA. Extremely well qualified. Articulate. Impressive in every measurable way. He was positioning himself as a transformation leader. Now, I’m not in the game of criticising anyone, or framing things negatively for my own gain. But my own personal observation here could save a board millions and years of wasted momentum.
Consider the last board meeting where AI featured in the strategy deck. The slides were polished. The use cases were compelling. The vendor had impressive references. Perhaps you even approved the budget.
Your next great leader may not be the sharpest speaker, but they will almost certainly be the best listener. We are good at measuring technical skill and cognitive ability. These are the table stakes for any executive role. Yet we still hire leaders with flawless resumes who create dysfunctional teams. This gap between competence and effectiveness is where value is destroyed.
Leadership performance in 2025 is being judged on evidence, not assertion. Boards, people leaders, and investors now have clearer data on where executive hiring is failing and which traits genuinely correlate with success. We can also see how inclusive hiring is evolving and how UK plc is progressing on representation.
You would not launch a new product without first understanding the user. So why build or sustain a leadership team without anchoring it around the customer? In too many organisations, the executive team still debates internal capacity or delivery dates. The people who pay your bills exist only as abstract figures in presentations. That kind of disconnect costs more than time. It weakens outcomes and magnifies wasted investment. Let's explore what a better approach looks like in practice.
Trust in senior leaders is also under strain. Only 14% of UK workers say they have faith in senior leaders’ decisions. That erosion shows up in slower adoption of change, more challenge behind the scenes and ultimately a higher cost of making anything stick. In this environment, the most important question is not "Is our strategy right?". A better question is, "Is the leadership system at the top capable of delivering it?".
When your business faces a critical inflection point, whether it’s a digital transformation, a turnaround, or a scale-up that has just secured funding, you can’t afford 12 months of drift. Spending that time recruiting, onboarding, and hoping the new hire finds their feet will only slow you down. What you need is precision. What you need is fractional firepower.
Mis-hiring is the silent landmine beneath your high-performing team. It’s not just a bad hire. It’s a culture destabiliser. A trust eroder. A progress killer. It may feel safe to chalk it up as “just one wrong person,” but recent data suggests the financial and relational toll is far heavier. A mis-hire can cost up to 30 % of the employee’s first-year earnings, including lost productivity, recruitment, onboarding, and disruption. So when an executive does not fit and the cracks start showing.
What’s 2+2 in leadership hiring? The answer isn’t always 4. Especially when you forget to account for the hidden variables: character and context. Almost 50–70% of new executives fail within 18 months, not for lack of skill but because hiring often overlooks character, cultural fit, and adaptability. We often think of hiring as a simple maths problem. You line up competence with experience and expect to find your next great leader. Except it rarely works out that neatly.
Are you hiring for comfort or for progress? It’s an easy trap to fall into. You sit across from a candidate who reminds you of yourself ten years ago. Or maybe they mirror someone on your team who’s been successful. They “just feel right.” That’s the comfort zone of culture fit. It feels safe. It feels smooth. But here’s the risk: If everyone looks the same, thinks the same, and solves problems the same way, fresh ideas never surface.
The executive mirage is what happens when we confuse presence with potential. It’s the polished speech, the poised manner, the confident stride into the boardroom that convinces us we’re looking at a high-impact leader. Traditionally, these signals have been held up as markers of leadership. Commanding tone. Sharp delivery. Decisiveness in meetings. These behaviours feel reassuring, especially under pressure.
Something that I firmly believe is an investment for any company's future is leadership development. As you will go on to read, I'm clearly not alone in that opinion. It’s common sense that training people to be better, more diligent, more focused and finding gaps in their skills is always a positive thing. It's also one of the first things to go when budget constraints are required. So, the big question: is leadership development really worth the money?
Imagine a busy international airport suddenly losing its air traffic controller. Planes are circling, communication is strained, and there’s a very real risk of collision. Who steps in? Not someone you’ll hire after six months of interviews… but a seasoned professional who can slot in now, restore order, and keep everything safely moving. Interim leaders are your organisational air traffic controllers, parachuting in when the stakes are high and time is tight.
We all know the phrase “culture fit”... it’s been baked into hiring decisions for decades. But here’s an uncomfortable truth, when overused or misunderstood, cultural fit can become a Trojan horse for unconscious bias. And the result? Leadership teams filled with people who look, think, and lead a lot like… well, you. That’s not cultural alignment. That’s cultural stagnation.
Over the years, I’ve seen plenty of leadership teams that look great on paper, strong CVs, strategic minds, ambitious plans. And yet… performance still drags. It’s a bit like driving a high-spec sports car with the handbrake half on. You can move forward, but the engine’s straining, the wheels don’t spin freely, and sooner or later, something burns out. So what’s holding these teams back?
I've been taking a hard look at the executive job market lately, and let me tell you, it's a fascinating beast in 2025. It's a bit like diagnosing a patient, we need to health-check the industry to really understand what's going on, both for the amazing candidates out there and for us in executive search trying to connect them with the right opportunities. Frankly, it’s a real mixed bag. Some sectors are booming, others are holding steady, and everyone's scrambling to adapt to this new world.
We spend so much time evaluating candidates on what's visible, but it's what lies beneath that truly determines their ultimate success.
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