The Difficult Conversation You're Avoiding
From avoidance to action: Why most 'difficult' conversations aren't actually difficult
There's a conversation you need to have. You know exactly what it is and who it's with.
You've been putting it off for days, maybe weeks. Every time you think about it, you feel a knot in your stomach. You've rehearsed it in your head dozens of times, imagining how it might go wrong.
So you delay. You hope the situation will improve on its own. You tell yourself you'll do it next week when things are less busy.
But the problem isn't getting better. It's getting worse. And now you're losing sleep over it.
Why Managers Avoid Difficult Conversations
🎭 Fear it will be confrontational You imagine shouting, tears, or awkward silences. You worry about damaging the relationship or making the person defensive.
🤷 Not knowing what to say You don't have a script. You're worried you'll say the wrong thing, make legal mistakes, or handle it badly.
⏰ Hoping it will resolve itself Maybe they'll realise the problem and fix it without you having to say anything. Maybe they'll leave. Maybe it will just go away.
😰 Fear of making it worse What if they get upset? What if they argue back? What if other people find out? What if it affects team morale?
The Reality About Difficult Conversations
Most difficult conversations aren't difficult.
They're uncomfortable, yes. But confrontational? Rarely.
Often, the employee knows there's an issue. They might even be relieved you're finally addressing it. They certainly respect you more for having the courage to lead.
The conversation you're avoiding is rarely as difficult as you think it will be. But avoiding it definitely makes everything worse.
How to Have the Conversation
📊 Start with facts, not feelings "You've been late four times this week" not "You seem to have a time management problem." "You interrupted Sarah three times in yesterday's meeting" not "You're being disrespectful." "Your report was submitted two days after the deadline" not "You don't seem to care about deadlines."
Facts are hard to argue with. Feelings and interpretations create defensiveness.
🎯 Focus on impact, not intent "When you're late, it delays the team meeting and affects everyone's schedule" not "You don't care about the team." "When reports are late, it delays the client presentation" not "You're letting everyone down." "When people are interrupted, they can't contribute their ideas properly" not "You're being rude."
You don't know their intent, but you can see the impact. Focus on what you can observe and measure.
✅ Be clear about expectations "I need you to be here by 9am every day" not "Try to be more punctual." "In meetings, please let people finish their point before responding" not "Be more respectful." "Reports must be submitted by the deadline we agree" not "Try to be more organised."
Vague requests get vague results. Specific expectations get specific changes.
Three Steps to Have Any Difficult Conversation
🗓️ Schedule it properly Don't ambush them. "Can we have a chat about punctuality? Are you free for 15 minutes this afternoon?" gives them time to prepare mentally.
🎯 Keep it focused One issue per conversation. Don't bring up everything they've ever done wrong. Deal with the specific behaviour that needs to change.
👂 Listen to their response There might be something you don't know. Personal issues, work challenges, or misunderstandings. Listen first, then work together on solutions.
What Usually Happens
In most cases, the person will:
- Acknowledge the issue
- Explain any circumstances you weren't aware of
- Agree to change the behaviour
- Thank you for being direct rather than letting it fester
The dramatic confrontation you imagined rarely happens. What you get instead is clarity, respect, and usually quick improvement.
The Cost of Continuing to Avoid It
Every day you don't have the conversation:
- The behaviour continues or gets worse
- Your stress increases
- Other team members notice your inaction
- Your credibility as a leader decreases
- The conversation becomes harder to have
The longer you wait, the bigger the issue becomes and the more difficult the conversation actually gets.
The Reality Check
You're not paid to avoid difficult conversations. You're paid to have them.
Leadership isn't about being liked. It's about being effective. Sometimes that means saying things people don't want to hear.
Your team needs you to address issues. They need to see that standards matter and that poor behaviour has consequences.
The conversation you're avoiding right now? It's probably not as difficult as you think.
But it's definitely necessary.
Schedule it. Have it. Move on.
Your team - and your peace of mind - will thank you for it.
Got a difficult conversation you've been putting off? The longer you wait, the harder it gets and the more it affects your credibility as a leader. If you need help planning your next steps then send me a DM.
