Why Leadership Teams Fail; And What Wellbeing Has to Do With It 

By: Keith Burnet, Chief Adventurer, The Alchemist & Adventurer

Leadership team failure rarely announces itself. It doesn’t usually arrive as a dramatic collapse or public crisis. More often, it unfolds slowly, through the erosion of trust, clarity and connection; until the culture becomes brittle and wellbeing quietly deteriorates. 

Leadership effectiveness exists on a continuum. At one end are teams characterised by trust, vitality and shared purpose. At the other are teams that drain energy from the organisations they lead. Most sit somewhere in between: functional, but fatigued; busy, but disconnected. 

Sometimes failure is part of renewal. Systems, including leadership teams, can strengthen through stress if they are able to reflect, adapt and regenerate. But many leadership teams don’t fail productively. Instead, failure becomes chronic and cultural. 

The warning signs are familiar: mistrust, competing agendas, avoidance of difficult conversations and an inward focus that eclipses the organisation’s wider responsibilities . Over time, this creates environments of constant low-level stress. People remain task-focused but emotionally disengaged. The work continues, but wellbeing erodes. 

These cultures are exhausting to inhabit. Feedback becomes unsafe. Conflict is either buried or explosive. Decisions take too long or unravel later because alignment was never real. Leaders become reactive rather than reflective. The emotional cost accumulates; not just for the team itself, but for the organisation watching from below. 

It’s important to distinguish failure from difficulty. Leadership is inherently demanding. Holding paradox, managing trade-offs and staying in relationship through tension is part of the role. Healthy leadership teams don’t avoid difficulty – they metabolise it. From a wellbeing perspective, health is not the absence of pressure, but the ability to recover, adapt and stay connected under it. 

Healthy leadership teams are recognisable. There is honest contact. Avoidance is low. Differences are explored rather than suppressed. Feedback moves quickly. Decisions have rhythm. Most importantly, there is psychological safety; the foundation of both wellbeing and good leadership. 

That safety doesn’t eliminate tension. It creates the conditions for truth. People can name what’s not working without fear. They stay engaged when conversations get uncomfortable. As a result, trust deepens and collective resilience grows. 

So why do leadership teams fail? Often because relational wellbeing is deprioritised in favour of technical competence. Because ego overrides empathy. Because leaders were trained to perform individually, not to lead collectively. And because exhaustion narrows perspective, making reactivity more likely than reflection. 

Most critically, leadership teams fail when they lose sight of the system they serve. When attention turns inward — to politics, personalities or power — wellbeing declines and purpose fragments. Urgency crowds out care. Connection thins. Culture deteriorates. 

Not every leadership team will be exceptional. But every team can be more conscious. It starts with telling the truth; about how people are really experiencing the work, how the culture feels under pressure, and what kind of leadership environment they are creating together. 

Failure may not be binary. But awareness is. Either a team is willing to look honestly at its culture and wellbeing, or it isn’t. And in workplaces today, that choice has never mattered more. 

Disclaimer: The views expressed in this opinion piece are those of the author and do not necessarily reflect the views of The Well Crowd. This content is for information and discussion purposes only and should not be taken as medical, health, or professional advice.