The Leaders Playbook: Difficult Conversations

There are times as a leader when you have to sit down and have a difficult conversation with a teammate.  Whether it’s feedback or a career course correction, it can be a challenge and painful, especially when the employee is trying hard but just not hacking it.  It is part of the job and we owe it to our teams to be good at it. 

In advance of having one of these conversations you must be clear on “why” you are speaking with them, “what” you are going to say to them, and perhaps most importantly “how” you are going to say things.  Never forget that it is possible to have a difficult conversation with an employee and still leave them with their dignity intact. 

Don’t walk into these conversations cold. Take some time to prepare. Sit down and write out the major points you want to make.  Be clear in your mind on how you intend to flow the conversation and think through the contingencies that could come up during your talk.   If needed, consult with HR or legal before you have the conversation, especially if you are making a job change for someone who did not expect it.

When you do sit down, be calm, collected, polite, but clear in the message you need to send. Listen with your ears and your eyes and never forget to leave someone with their dignity and self-respect intact as much as possible. Summarize at the end of the conversation the action points you are taking, the due dates, and next steps.

There are some good books on this topic that I recommend. One I recommend is “Difficult Conversations- How to discuss what matters most” by Stone, Patton, and Helen.

Good luck and lead well.

The Author is currently serving as an active-duty military officer. Any comments or recommendations on this post or on this site are solely and expressly my personal views and do not represent the position of any branch of the United States Government, the Department of Defense, or the Department of the Air Force.