Difficult Conversations at Work

Whether it's giving critical feedback, addressing performance issues, negotiating salary, or confronting a problem colleague, difficult workplace conversations are unavoidable. Most men either avoid them entirely or handle them poorly: too aggressive, too passive, or too vague to accomplish anything. Neither approach works. Avoidance lets problems grow. Aggression damages relationships. Vagueness wastes everyone's time.

The skill of having direct, respectful, productive difficult conversations is one of the most valuable professional abilities you can develop.

Why We Avoid Hard Conversations

• Fear of conflict or confrontation
• Worry about damaging the relationship
• Uncertainty about how to say it
• Hope that the problem will resolve itself
• Past experiences that went badly

Every day you avoid the conversation, the problem grows and the conversation gets harder. What feels like keeping the peace is actually letting things get worse. Address it early, address it directly, move forward.

How to Have the Conversation

Prepare: Know what you want to say and what outcome you want.

Be direct: Get to the point. Don't bury the message in pleasantries.

Be specific: Address concrete behaviors or issues, not vague complaints.

Be respectful: Direct doesn't mean harsh. You can be clear and kind.

Listen: Make space for their perspective.

Focus on solutions: What happens next matters more than who's to blame.

Your Action Steps

This week: Identify a conversation you've been avoiding at work.

This month: Prepare for and have that conversation.

This quarter: Build the habit of addressing issues early rather than letting them fester.