Having Difficult Conversations

Larry Tucker

We all seem to be similar in some ways. One very common characteristic among leaders and managers is our allergic reaction to difficult conversations. My limited perspective indicates that this is even more prevalent in nonprofits, where being empathetic to others’ situations is the “minimum requirement” for a leadership role, so creating conflict and hurting someone’s feelings are not outcomes we typically try to achieve.  

You’re probably familiar with this “phobia”: You’ve been meaning to have this conversation for a while, but dread it. Meanwhile, this person’s inappropriate activities have been accumulating. You are ready to burst, and in fact, you’re a little afraid that when you have the conversation, you may overreact…spill out everything in a waterfall of past transgressions and ill feelings that could flood the whole relationship. This could be a situation with a peer, a boss or a subordinate. 

You may have talked yourself out of having this conversation: It won’t help. Now’s not the right time. It’s not my problem.

The bad news is that I don’t have a silver bullet. You will feel uncomfortable in this conversation, and someone may leave this conversation feeling “wounded”. The good news is that there are some “templates” that will help guide you through conversations like this. One excellent source is the book Difficult Conversations by members of the Harvard Negotiation Project.  

If you are a manager, you must have these conversations. If you have been avoiding them, start researching and practicing. As an executive director, you will likely have these conversations with employees, volunteers, board members, and maybe even donors.  

Here are a few ideas to start you on this path:   

  • If you aren’t sure if this situation merits a conversation, ask some others. Get some objective views.  
  • Don’t let it build. Say something early on.  
  • If you are a manager, don’t save all your comments for the annual performance review. Find reasons to have conversations frequently.  
  • For a manager, the best approach is direct and time-sensitive. Have the discussion soon after the event in question, BUT wait until the next day. Think about how you want to approach the discussion. 
  • Start the conversation with questions.  
  • Remember and recognize the person’s strengths and the value that he/she has added to the organization.  

This can be a noble goal for you: Initiate one difficult conversation in the next month. The first one is the toughest.

Author:  Larry Tucker,  Executive Coaches of Orange County,  www.ECofOC.org