Yes, YOU … every leader has one.
A conversation they’ve rehearsed dozens of times in their head, but never had.
It may be addressing poor performance. Challenging the behaviour of a high performer. Confronting a colleague whose attitude has changed. Or naming the issue everyone else can already see, but no one is willing to say out loud.
The conversation itself may be short, but living with it can take months.
Research suggests that avoiding difficult workplace conversations comes at a cost. Leaders experience increasing stress and mental load. Teams lose trust, clarity and momentum. The person being avoided is often left confused, unaware of the issue, or uncertain how to improve. Conversely, leaders who address conflict constructively help reduce workplace stress and restore a greater sense of control for everyone involved.¹²
Avoiding the conversation doesn’t remove the cost. It simply delays it—and usually asks everyone to pay something, even the leader.
There are excellent books that teach leaders how to have these conversations. Crucial Conversations, Radical Candor and Candid Conversations all offer practical frameworks for speaking with greater skill and confidence.
But before asking how to have the conversation, I wonder if we should first ask something else.
What is stopping us from having it? When waiting is wisdom... and when it isn’t
Research suggests leaders often postpone difficult conversations for reasons that sound entirely reasonable.
· “It will sort itself out.”
· “I don’t want to damage the relationship.”
· “Now isn’t the right time.”
· “They’ll realise it themselves.”
· “I need a little more time to think.”
Sometimes those reasons are valid.
An emotionally charged conversation rarely ends well. There are moments when more information is needed, emotions need to settle, or the other person simply isn’t in a position to hear what needs to be said.
Good leaders don’t rush difficult conversations. But neither do they hide behind good reasons indefinitely. The difference lies in the purpose of the delay. Waiting creates the conditions for a better conversation. Avoidance protects us from having one.
One of the privileges of coaching leaders is that I get to sit with them beneath the surface of the problem. Interestingly, the conversation they think they’re avoiding is often not the real issue. As we explore what’s happening, something more personal frequently emerges.
Sometimes the conversation we keep postponing isn’t exposing the weakness of the employee. It’s exposing the fear of the leader.
Perhaps they’re afraid of damaging a relationship they’ve worked hard to build. Perhaps they don’t want to be seen as harsh or unfair. Perhaps they’re worried they’ll handle the conversation badly. Perhaps they’re wrestling with the uncomfortable reality that the issue should have been addressed months ago.
Notice what has happened. The focus has quietly shifted. The conversation is no longer just about the employee. It’s about the leader.
That’s why one question has become increasingly important in my own coaching.
Not: “What should you say?”
But: “What is your silence protecting?”
Because every avoided conversation serves something.
· Comfort
· Approval
· Certainty
· Control
None of those make us weak. They make us human. But they can also quietly undermine our leadership.
The difficulty with avoidance is that it doesn’t even really protect the leader. While we experience temporary relief, everyone else begins carrying the consequences. The team wonders why obvious issues are left untouched.
Standards become blurred. Trust weakens because people no longer know what will—or won’t—be addressed. The individual who most needs feedback loses the opportunity to grow.
Meanwhile, the leader continues carrying the emotional weight of a conversation that becomes heavier with every passing week.
The silence that once felt protective gradually becomes exhausting.
One of the biggest myths in leadership is that courageous leaders are fearless. I don’t believe they are. I think courageous leaders become curious. Curious about the stories they are living from.
· The story that conflict damages relationships.
· The story that kindness means avoiding discomfort.
· The story that good leaders shouldn’t upset people.
· The story that every difficult conversation has to be handled perfectly.
Those stories often begin with good intentions. But there comes a point where they cost more than they protect. When leaders begin letting go of those old assumptions, something remarkable happens. Conversations become clearer because they are no longer carrying weeks of anxiety. Accountability becomes more consistent because expectations are spoken instead of assumed. Trust grows because people know where they stand. Teams spend less energy navigating uncertainty and more energy achieving meaningful results. And leaders often discover that the very stress they were trying to avoid begins to disappear.
The difficult conversation hasn’t changed. The leader has.
If this article has caused you to reflect on conversations you postpone, perhaps the next step isn’t simply learning another communication technique. Perhaps it’s understanding what your avoidance has been protecting—and whether it’s still serving you.
If you’re ready to explore that journey, I’d love to support you on it. Together we can uncover the assumptions that may be keeping you stuck, restore the confidence and clarity to lead difficult conversations well, and create a team characterised by greater trust, healthier accountability, stronger performance, and a leader who no longer carries unnecessary stress alone.
References
National Centre for Social Research. (2025, November 19). How do UK workers experience, respond to, and resolve conflict in the workplace?
MIT Press Journals. (2012). A helping hand? The moderating role of leaders’ conflict management behavior on the conflict-stress relationship of employees. Negotiation Journal, 28(3), 253–279.
Own Your Leadership. (2026, April 5). Why leaders avoid difficult conversations
