Why leadership teams fail

Being invited to write about why leadership teams fail has sparked more reflection than I expected. What does it mean for a leadership team to fail?

Failure is rarely sudden. It sneaks in quietly, unobtrusively - sometimes barely noticeably. It also occurs to me that success and failure in leadership teams isn’t binary - there aren’t just teams who succeed and teams who fail, they live on a continuum of effectiveness, of impact, of aliveness. At the one end, there are those rare teams that function as high trust, high impact collectives. At the other end, there are those that damage and erode the organisations they are meant to steward. Most fall in the middle - muddling through, functional enough to keep going, but far from fulfilling their potential.

Sometimes, in fact, failure is necessary. As Nassim Nicholas Taleb reminds us in Antifragile, certain systems - when exposed to stress or even collapse - rebuild stronger. Leadership teams aren’t exempt from this logic. There are times when failure isn’t a sign of dysfunction, but of recalibration. That is the systemic view. Healthy systems need to regenerate, and failure may well be part of that cycle.

It’s not hard to find examples in the business world: big brand retailers like Woolworths, British Home Stores and Thomas Cook, slow to adapt, eventually collapsed under the weight of their own inertia. Their leadership teams didn’t necessarily implode overnight - they failed to evolve, to listen, to learn. And in doing that, they created space for newer, more agile systems to emerge.

It goes without saying that many failures aren't useful. In many leadership teams, failure takes a more insidious form. It's not the spectacular fall that grabs headlines; it's the slow erosion of trust, clarity, and purpose.

The warning signs are often familiar. Endemic mistrust. Quiet or overt sabotage. Competing agendas instead of collaboration. A fixation on internal dynamics at the expense of the wider stakeholder system. The absence of a shared vision or collective endeavour. What emerges is a kind of hollow busyness - people circling each other, retreating into silos, speaking in code, or avoiding the conversations that matter most. We know it when we feel it. We sense it in the room. We see the shoulder shrugs, the tight jaws, the politeness that covers up something far more brittle.

In these environments, individualism thrives. People work to protect themselves, not to advance shared goals. Feedback becomes rare, slow, or weaponised. Conflict is either buried or incendiary. Decisions take too long - or worse, are made without genuine alignment, only to unravel in execution. Over time, the emotional cost rises, and the organisation and its people feel the ripple effects.

And yet, it’s important not to conflate failure with difficulty. Leadership - real leadership - is hard. The work of holding paradox, engaging difference, making trade-offs, and staying in relationship through tension is inherently challenging. A healthy leadership team doesn’t eliminate difficulty; it embraces it as part of the job. As systems thinkers remind us, the essence of health is not ease, but responsiveness. A living system is one that adjusts, metabolises stress, and evolves. Leadership teams are no different.

McKinsey’s research, as outlined in this article from October 2024, Go teams, when teams get healthier, the whole organization benefits echoes this: healthy teams generate measurable improvements in organisational performance, but health isn’t about harmony - it’s about the ability to navigate complexity with resilience. That requires a culture where feedback flows, conflict is purposeful, and team members know what they are engaged in together.

Conversely, the signs of a healthy leadership team are just as palpable. There is contact - frequent, honest, and unguarded. Avoidance is low. Respect is high. Differences are not merely tolerated but appreciated. There’s a rhythm to decision-making, a speed to feedback, and perhaps most importantly, a kind of penumbra of trust surrounding the team. People feel it. They may not name it, but they move differently because of it - more openly, more creatively, more responsibly.

That trust isn’t sentimental. It doesn’t mean everyone agrees, or that tension disappears. It means there’s enough safety to tell the truth. And enough shared purpose to stay in the room when it gets hard.

So why do leadership teams fail?

Leadership teams fail because trust is hard to build and easy to erode. Because ego often triumphs over empathy. Because organisations often reward technical skill over relational intelligence. Because leaders get tired, or scared, or stuck in old patterns. Because no one ever really taught them how to lead together - only how to lead individually.

But perhaps most of all, leadership teams fail when they lose sight of the system they serve. When the focus turns inward - on personalities, politics, or position - teams disconnect from their wider purpose. They stop listening. They become reactive. And slowly, sometimes imperceptibly, they begin to fail.

Not every team can be extraordinary. But every leadership team can be more conscious. It starts with telling the truth - about what’s working, what isn’t, and who they want to become together. Failure may not be binary, but awareness often is. Either a team is willing to look in the mirror - or it isn’t.

And so, the real question becomes: what kind of team are we willing to be - when nobody's watching, and everything is at stake?