How to Have a Difficult Conversations

We all have them, or at least we should be having them. Difficult conversations are essential for a successful manager but they can be the last thing we want to do.

I had a long history of avoiding difficult conversations. Like most, I dreaded them because they always seem to go poorly.  The employee inevitably leaves in tears, the door would slam on the way out, you get the picture. A few years ago I heard a rumor that one of my remote employees was working out of his house instead of our offsite office. Even though I thought I was prepared with lots of evidence of his wrong doing, I didn’t really think through how the conversation would actually. By the time it happened, it was pretty emotional on both sides and very unproductive. It consisted mostly of: “I can’t trust you,” “You can’t be trusted,” “I can’t trust that I can trust you,” basically the same conversation my mom had with me when I was nine and skipped Sunday school. My employee probably felt like he was being treated like a nine year old and I felt pretty bad afterwards as well. In the end our relationship never recovered (with my employee that is, my mom forgave me).

Things changed for me after I read the great book “Difficult Conversations – How to Discuss What Matters Most.”  In the book, the authors give great advice and guidelines for practical use.  The five points that resonated most with me were:

  • Look at how the problem may be threatening your identity. Having difficult conversations can be very anxiety producing, not just because we have to confront the other person, but also ourselves.  For me, the incident with my employee was threatening my competency as a manager.
  • Try and learn their story. If I had done that, I would have learned that the remote office was really horrible and not conducive to work. There were people yelling at each other next door, the air conditioner didn’t work, and the internet was always down.  In truth, it would be hard to ask anyone to work in those conditions.
  • Begin from the third-party perspective. Think what a neutral observer would say, and approach the conversation that way. In this case, a third-party would have pointed out: there was an agreement on the use of the office; however, there were serious issues with the space. Instead of communicating the issues, the employee thought he could make his own decision to stop using it.  The boss sees this as a trust issue, trust issues are central to his being, caused by a tragic Sunday school skipping incident.
  • Express your views and feelings. Most of the time we never talk about our feelings in these situations. You’re going to have them, so best to just get them out there. Just label them and move on, no need to have them hover and cloud up the conversation. I was pretty pissed at this guy for violating my trust, and thought the situation was pretty serious. It showed in my body language and tone of voice, which killed any hope of coming to a decent resolution. It would have been better to just put get the feelings out and move on to resolving the problem.
  • These situations are opportunities for growth. The goal is to make all difficult conversations “learning conversations.” In the end, there should be lessons learned by both parties and progress made to positive change. I like the quote from Richard Bach – “There is no such thing as a problem without a gift for you in its hands. You seek problems because you need their gifts.”

I would love to hear about conversations you dreaded that turned out well.

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