Leadership Tip: Lead Difficult Conversations


Have you avoided a difficult conversation and inadvertently caused the situation to worsen?


Leading difficult conversations is a leadership challenge that’s so daunting many avoid it. Yet, if you don’t do it as a leader, you frankly don’t deserve your job. These conversations are not something you can neglect, even if you’re convinced you can work around them or they’re not that important, given your long to-do list.


You have to practice, role-play, and rehearse these conversations repeatedly. Unlike the countless other leaders who are well-intentioned but never exercise the courage to be honest, you can change the entire trajectory of someone’s life.


Consider the following “dos and don’ts” for holding difficult conversations:


- Don’t get stuck in the preparation phase. Practice is vital, but don’t use it as an excuse not to hold the real conversation.
- Don’t use comparative language: “You should write your reports the way Emily does.”
- Don’t assume you have all the facts. It’s possible there’s a story behind the story, and while it may not change the feedback you offer, the additional context may change how you deliver it.
- Do Think Win-Win. Make sure your motives are genuine.
- Do describe your concerns. Use terms like “I was surprised to hear…” or “I’m concerned about…”
- Do give specific examples. Focus on facts versus your opinions.
- Do listen. Concentrate and reflect on the way the other person feels.
- Do ask open-ended questions: “People are perceiving you this way — can you tell me why you think that’s happening?”
- Do be as specific as possible without violating the person’s privacy. It’s a delicate balance that requires sophistication and genuine care.


Successful leaders can learn to lead difficult conversations from colleagues who are senior, peers, other team members, and specialists. Sit down and share the situation with someone at the right organizational level and ask how they’d handle the conversation.



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