Complex characters

Dealing with difficult individuals is one of the most challenging and draining aspects of leadership. It is not the occasional disagreement or personality clash that concerns me, but the persistent behaviours that, if left unaddressed, begin to shape the culture in ways no leader should accept. Sometimes that behaviour is overt, such as public pushback in every meeting. Other times it is quieter, like a refusal to collaborate, the slow drip of negativity, or subtle resistance to change. Regardless of the form, the impact is the same: trust erodes, productivity drops, and the team begins to feel it.

The first step is always diagnosis before action. People rarely set out to be difficult. Misalignment, burnout, fear, lack of clarity, or feeling undervalued often sit beneath the surface. I have had situations where a leader’s perceived resistance was actually the result of being overwhelmed, or where frustration stemmed from a disconnect between how they measured success and the company’s priorities. Starting with curiosity and asking direct, open questions has consistently given me better insight into whether the challenge is about capability, mindset, or environment.

Once I understand the “why,” I can shape the “how.” That starts with timely, candid feedback. Waiting too long only normalises the behaviour. I focus on being precise, using specific incidents, tangible impact, and a clear picture of what good looks like. Instead of saying “be more collaborative,” I describe the observable behaviours I expect, such as contributing without interrupting, engaging constructively with differing views, and following through on joint deliverables. Whenever possible, I pair this with data such as 360 feedback, engagement scores, or missed delivery milestones, so the conversation is grounded in more than my perspective.

From there, I like to move into structured support that includes measurable objectives, regular check-ins, and, where appropriate, peer or skip-level coaching. This is also where I align with HR or my leadership peers to ensure the loop is kept tight, and the situation is not carried by me alone. Having consistent expectations reinforced from multiple angles reduces the risk of the individual rationalising away the feedback.

If progress is made, I recognise it openly. It is important for both the individual and the team to see that change is possible. If there is no movement, I escalate with transparency. That can mean formal performance management, role changes, or, in some cases, separation. I have had to make the difficult call to move on high performers who were cultural liabilities. It is never easy, but protecting the trust and cohesion of the wider organisation outweighs the short-term pain of losing output.

One trap I see leaders fall into, and one I experienced earlier in my career, is holding onto the problem for too long in the hope that coaching will eventually work. Inaction is a decision in itself, and teams notice what you tolerate. The moment that inaction starts to erode psychological safety or slow execution, the problem is no longer an individual performance issue but a leadership credibility issue.

At this level, dealing with difficult individuals is not simply about conflict resolution. It is about cultural stewardship and organisational health. It involves diagnosing root causes, delivering feedback with clarity and fairness, aligning with stakeholders, tracking progress objectively, and taking decisive action when it is clear that change will not come. All of this must be done in a way that reinforces the values you expect the rest of the organisation to live by.

The most rewarding moments are when someone takes the feedback, commits to the change, and flourishes. The hardest times are when you need to part ways. In both cases, the responsibility remains the same: lead with empathy, act with decisiveness, and protect the environment your teams need to thrive.