There are two things that many leaders do not like to do:

  1. Have difficult conversations
  2. Make difficult decisions

Both of these are essential to excellent leadership.

Dan Rockwell shares some very helpful thoughts on stepping into difficult conversations.

Guest Post by Dan Rockwell

It’s stressful to host a crucial conversation. Not having it is worse. Every day is dark when you delay difficult conversations, but most of us do. It’s not caring to tolerate the unacceptable. Timely action increases success and lowers stress.

Before difficult conversations:

  1. Aim for the best outcome. Know what you want. What does it look like if things go perfectly?
  2. Engage in negative thinking. Design a one sentence response for any bad incident. What will you do, for example, if someone starts yelling?
  3. Seek to advantage others.
  4. Document disappointments.
  5. Show up curious. Hold back your conclusions and judgements. Be certain you understand what’s happening. Assumptions are deadly.One of my coaching clients shared his approach during a recent crucial conversation.

    #1. Meet face-to-face. Don’t use email. Use a neutral place.

    #2. Share the agenda before people show up. Reduce uncertainty.

    #3. Include others. When someone’s supervisor or manager is involved, include them.

    #4. Project minutes on a big screen. Let everyone see the situation in writing.

    #5. Design a clear action plan. Be helpful and expect commitments.

    #6. Explain consequences. “If we can’t resolve this our next steps are….”

    “If we can’t resolve this the outcome is….”

    #7. Set the follow-up meeting.


Get your thoughts out of your head and down on paper. Your brain feels better when it sees you writing. It’s okay to imagine the worse as long as you prepare for it. Negative imaginings defeat without positive action plans. Choose to challenge and support. Keep the goal in mind and stay flexible. It probably won’t go as planned.

People wait for the leaders to deal with painful situations.

Still curious:

6 Power Tips for Having a Tough Conversation

7 Tips for Difficult Conversations