Small problems rarely stay small
Most workplace problems don’t suddenly appear overnight; they more than likely have been bubbling away for a while. And many of them could have been nipped in the bud early on, but an avoidant manager may not have wanted to tackle it head on, instead ignoring it or waiting to see if it disappears. Poor behaviour gets ignored. A performance issue isn’t addressed early enough. Tension starts building between team members but nobody really wants to tackle it. Leaders often hope things will just settle down on their own.
You’ve probably seen it happen yourself, most leaders have. The interesting thing is that many of the bigger people problems inside organisations don’t come from one major event. They come from smaller conversations that never happened when they should have. And while avoiding those conversations might feel easier in the short term, it usually creates far more work in the long run.
One of the tests of a good leader when something uncomfortable needs to be addressed and the leader has to decide whether to lean into the conversation or step around it.
Why leaders avoid difficult conversations
A lot of leaders convince themselves they’re avoiding conflict to protect the relationship. The problem is, silence creates ambiguity and uncertainty. People feel uneasy working for leaders who are known not to have direct and honest conversations, not to give honest feedback. People like to know where they stand. In effective leadership there is no room for avoiding difficult conversations. As Brené Brown says:
“Clear is kind. Unclear is unkind.”
Good teams operate well when expectations are clear, standards are consistent and feedback happens early enough to be useful. But difficult conversations are still something many leaders avoid. Why?
Sometimes it’s because they don’t want to upset someone. Sometimes they’re worried about the reaction. Sometimes they don’t quite know how to start the conversation. And sometimes, if we’re honest, it’s simply because uncomfortable conversations are uncomfortable and we tend to put them off.
The real cost of avoidance
The trouble is that unresolved issues rarely stay small. Left alone, they tend to grow quietly in the background. The behaviour continues, frustration starts building within the team and before long good people begin wondering why certain things are being tolerated while other standards still apply to everyone else.
Most leaders have probably experienced this at some point. What could have been handled with a straightforward conversation early on slowly becomes a much bigger issue requiring far more time, energy and emotional effort to manage later.
And that’s where the real cost starts to show up. Avoiding conversations creates work. Teams end up revisiting the same problems, correcting the same mistakes and dealing with the same frustrations over and over again because the issue was never properly addressed in the first place. A simple conversation delayed for weeks or months can eventually create hours of rework, confusion and unnecessary tension across the team.
No leader really needs the extra admin of unaddressed problems in today’s workplace. There’s already constant change, nonstop communication, uncertainty around the economy and now the growing pressure surrounding AI and technology changes.
Many leaders are feeling tired themselves, which probably explains why difficult conversations are becoming even easier to postpone. But that’s usually when leadership matters most. Brené Brown makes a good point when she says:
“You can choose courage or comfort. You cannot have both.”
Sometimes you need to jump into short-term discomfort in order to create longer-term clarity, trust and stability for the team.
Healthy teams talk early
Some leaders still think a healthy workplace is one where nobody disagrees or challenges anything. More often than not, it simply means people have stopped speaking up.
Healthy teams are not conflict-free teams, they are teams where people know issues can be discussed early, honestly and respectfully without someone feeling attacked or humiliated in the process. You can care about people and still address behaviour, performance or expectations clearly. In fact, avoiding the conversation is often less caring in the long run because everyone around the issue can usually see it anyway.
And when leaders stay silent, people naturally start filling the silence with their own conclusions.
Another pearler from Brené Brown is:
“Courage starts with showing up and letting ourselves be seen.”
Sometimes good leadership is simply being willing to have the conversation everybody else is hoping to avoid.
Practical Ways to Approach Difficult Conversations
- Address issues early
Small conversations are nearly always easier than delayed ones. Waiting rarely improves the situation. - Focus on behaviour, not personality
Talk about observable actions and their impact rather than labelling the person. Instead of saying: “You’re unreliable” try: “The last few deadlines were missed and it impacted the rest of the team.” People respond far better when they don’t feel personally attacked. - Stay curious
Some of the best leadership conversations start with genuine curiosity. Questions like: “Can you help me understand what’s been happening?” or “What challenges are you dealing with at the moment?” can completely change the tone of the discussion. - Regulate your own emotions first
If emotions are running high, pause before having the discussion. Difficult conversations rarely go well when people are reactive. - Normalise feedback
If feedback only appears when something has gone badly wrong, people naturally become anxious about it. The healthiest teams are usually the ones where feedback is part of everyday leadership rather than a once-a-year event.
How are you showing up for the hard conversations? I’d love to hear from you. Don’t let the conversations you avoid today become the bigger problem you have to deal with tomorrow.
Rod Matthews