How To Have a Constructive Conversation With a Difficult Colleague or Team Member

Every leader has a situation they hope will quietly resolve if they give it a little more time. A behaviour that isn’t quite right, a pattern that keeps repeating, or a comment that crosses a line. You wait, partly because you’re busy, partly because you want to give the person the benefit of the doubt, and partly because you’re not entirely sure how to raise it. But as the days slip by, the behaviour continues, the team notices, and the weight of the unspoken conversation grows heavier. 

If this feels familiar, it’s not a sign of poor leadership. It’s a sign that you’re human. Even experienced leaders find these conversations challenging, partly because they rarely involve simple feedback. They come with history, emotion and unspoken expectations, which can make them feel heavier than they look on paper. 

Difficult conversations are one of the most challenging parts of stepping into leadership, particularly if you’re early in your career or managing people you’ve previously worked alongside. 

It’s Not Usually About “Difficult People” 

A helpful shift in perspective is to recognise that the issue rarely lies with a “difficult person.” More often, the difficulty sits in the dynamic between you, your role and the behaviour you need to address. That dynamic can feel personal and complicated, which is why these conversations carry emotional weight long before they begin. You are not the problem, but you are the leader, which means the responsibility for addressing the situation rests with you. 

Why Middle Leaders Often Hesitate 

There are many understandable reasons leaders delay these conversations. They don’t want to damage a relationship or appear heavy-handed. They worry about getting it wrong or making matters worse. Some have had difficult experiences in the past, while others feel younger or less experienced than the colleague they’re managing. Many are unsure whether senior leadership will support them, and plenty simply don’t have the emotional bandwidth to deal with conflict at the end of a long week. 

When these factors combine, hesitation is completely normal. But avoiding the conversation doesn’t make it disappear. In most cases, it quietly grows. 

The Cost of Avoiding the Conversation 

When issues remain unaddressed, the impact shows up gradually. Tension within the team increases. Standards slip. Tasks begin to drift back onto the leader, who feels increasingly overloaded. Resentment can develop among colleagues who notice the behaviour but don’t see it being tackled. And leaders often experience a loss of confidence in their own authority. 

Highlighting these consequences isn’t about blame. It’s about recognising why addressing the issue matters. 

Focus On What You Need To Talk About 

Before thinking about how to phrase things, it can help to focus on what you need to talk about. A simple starting point is to prepare for the behaviour, not the person. Identify the specific behaviour that needs to change, why it matters and what “better” would look like. Many conversations become muddled because the leader hasn’t reached clarity themselves before walking into the room. Starting with clarity rather than emotion makes the discussion far more grounded. 

This is only one piece of the wider skillset, but used consistently, it gives leaders a steadier foundation to work from. 

The Real Gap: Knowing vs. Doing 

This is the part most leadership advice tends to gloss over. Knowing the steps is rarely the challenge. The difficulty lies in putting them into practice, calmly, confidently and consistently, when the situation feels awkward or emotionally charged. Leaders often understand the theory, but they don’t feel equipped or supported enough to act on it. 

This gap between knowledge and practice is where most leaders feel stuck. 

How To Lead with Impact  

This is why we created Lead with Impact.  

Our 12-week virtual leadership programme helps middle leaders develop the confidence and clarity to inspire their teams and drive performance. The programme is designed not to give leaders more information, but to provide structured, supportive space to practise the parts of leadership that feel hard.  
It’s a practical, confidence-building approach for leaders who want to do more than understand leadership, they want to feel able to live it day to day. 
 
If you’ve been avoiding a difficult conversation, Lead With Impact will help you approach  it with more clarity, confidence and support. 

Find out more, and sign up here