How to Have Difficult Conversations

If the reason you avoid difficult conversations is that you think you’re not being nice, think again. You’re like a surgeon. In every surgery, there is some pain involved, but it’s good pain; it’s pain that helps and heals, not pain that damages.

Recently, I spent time with a CEO whose company had let five relatively senior people go within the previous six months. I asked him to bring out their “coach and connect” forms (a quick performance review) and discovered that all of them had been rated as “A” players prior to their release. He immediately called in the senior managers responsible for these fires, and asked, “What gives? How did these people get great scores from you, and then get fired after receiving their great reviews?”

The managers hung their heads and generally looked sheepish. As we talked further, the truth came out. For various reasons, none of them felt comfortable having the tough conversations. There were many reasons, but at bottom, they came down to just one thing. They felt that engaging in difficult conversations wasn’t a nice thing to do. People’s feelings were sometimes hurt in the process, and it was uncomfortable for everyone involved. My advice to them was the advice I’m also going to give to you. Change the tapes that play in your mind surrounding having challenging conversations.

We’ve been taught to believe that these sorts of conversations should be adversarial, confrontational, and unpleasant. That’s not how I approach them at all. I view myself as a coach, who is trying to remove obstacles so the person I’m coaching can succeed and be the very best version of him or herself.

I know that when I’m addressing difficult issues, I’m actually being kind. I’m giving the person a chance to make a shift that could change everything for the better. If I decide to take the easy way out and avoid the conversations, his or her career probably will take a bad turn. Maybe he or she will end up being fired, and hurt and bitter. I have an opportunity to help him or her change all of that.

With that in mind, here’s how I suggest you approach your next difficult conversation.

  1. Adjust your attitude. Make sure you’re having the conversation because you want to help the person. If you’re angry and want to hammer him or her, take some time to process your emotions so you’re in a place where you really do want him or her to win. Begin the conversation by saying the words, “I want to help you win.’ If the person you’re talking with believes that you’re against him or her, or don’t like him or her, you won’t achieve much. He or she needs to know that you care. Make sure you do.
  2. Adjust your paradigm. Change the conversation from “understand what I have to say to you” to “help me understand what’s going on in your life.” Let’s say a person who was once engaged at work now seems distracted and unengaged. You really have no idea what’s going on in the subtext of his life. Maybe he’s going through a difficult time at home. Maybe he’s struggling with health issues. Maybe something is happening at work that you’re unaware of that is discouraging him. You just don’t know. Whatever the reality is, until the person you’re coaching feels fully understood, you won’t make progress with him. Use phrases such as “please elaborate,” “tell me more,” “help me understand.”
  3. Don’t assume motives. At some point, you will need to bring up the uncomfortable issue that has necessitated the conversation in the first place. But if you lead with, “I can see that your attitude stinks,” you’ll only encounter resistance. Instead, withhold judgment and discipline yourself to cite objective, observed behaviours. Don’t cite rumors or tell them your guesses. “I note that you’ve been late for three shifts this week” will get you a lot further than “Why are you being so sloppy?”
  4. Brainstorm together to discover mutually acceptable solutions. Remember, you’re a coach. You’re there to help remove obstacles that could hinder people’s success. Once you fully understand the situation from their perspective and have had a chance to share yours in a non-judgmental way, it’s time to come up with solutions. Work together to come up with some solutions both of you can live with, and that you can hold them accountable to fulfilling.

If the reason you avoid these conversations is that you think you’re not being nice, think again. You’re like a surgeon. In every surgery, there is some pain involved, but it’s good pain; it’s pain that helps and heals, not pain that damages. Once you understand that your intervention could save this person from serious harm, you’re going to find it easier to have those conversations. But your own mental narrative must change before any of that happens. The first sale is always to yourself.

Trevor Throness is the author of “THE POWER OF PEOPLE SKILLS: How to Eliminate 90% of Your HR Problems and Dramatically Increase Team and Company Morale and Performance (Career Press, August 2017). He is a veteran business coach who specializes in working with growing businesses.


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