The Art of the Difficult Conversation

I’ve always been a people pleaser. I hate making people uncomfortable. I hate delivering news that might hurt their feelings or make them sad. I hate breaking up with people, whether in business or my personal life. In a nutshell, I really dislike difficult conversations. Which can make owning a business tricky.

You see, life hands you lots of situations where you can either have a difficult conversation or you can be angry and resentful about someone else’s behavior, or behave in a passive-aggressive manner, or swallow your concerns and be miserable. And sometimes, in business, keeping your mouth shut can result in you allowing a bad decision by a partner or employee go too far, and can cost you everything you’ve worked so hard to build.

In light of that realization, I’ve spent the past year forcing myself to get better at difficult conversations, whether business or personal. Through actually having those moments, I’ve come up with some tips to make the process easier, if never exactly pleasant.

  1. Follow Thich Naht Hanh’s advice. Hanh is a Vietnamese Buddhist monk, teacher, author, poet and peace activist. In my quest for strength in the face of conflict, I turned to some of his teachings. He repeats, time and again, that before you say ANYTHING to another person, you should ask yourself three questions. Is it true? Is it necessary? Is it kind? If you can answer yes to all three of those questions, then the conversation might be difficult, but you are coming to it from a place of care, not scorn. And the end result is that the person to whom you are speaking will have a better chance of realizing that you mean well, and the only reason you are speaking to them about this issue is because you care about them, the issue and your ongoing relationship.
  2. Keep the sarcasm at bay. I was raised in a household of sarcasm and point-scoring. We loved each other, but part of growing up was learning how to be sharp-tongued and witty. But that’s never productive in a situation where you are trying to have a serious, well-intentioned conversation with another person. Being sarcastic or sharp will only serve to raise their defenses and then, in turn, shut you out.
  3. Never be passive-aggressive. Be direct. If you truly have an issue, a concern, a problem with a decision or the actions of another person, be absolutely direct with them. Say, to their face, in a calm moment, “Bob, I saw what happened out there and frankly, it concerns me.” Or, “Bob, we’ve been discussing this acquisition for some time and I have deep concerns I’d like to discuss with you.” Etc. Beating around the bush just leads to confusion and frustration.
  4. Don’t wait. The best time to discuss an issue is as soon as possible. If you have concerns, letting them stew isn’t going to help, and the person about whom you are concerned may continue that behavior, to the detriment of everyone involved. Pull the person aside, have the conversation, and clear the air.
  5. Do wait. Don’t have these conversations when you are angry or upset, if you can help it at all. Heightened emotions rarely lead to rational discussions. If you charge directly at someone in a lather, not only are you less likely to clearly articulate your concerns, you are also MORE likely to cause them to shut down to the point that they no longer listen to you, which is counter-productive.
  6. Don’t beat a dead horse. Once you’ve said your piece, move on. If the issue is resolved, fantastic. If the issue isn’t resolved and the person is a subordinate, disciplinary measures need to be invoked. If the issue isn’t resolved and there’s literally nothing else you can do about it, let it go. Continuing to turn the situation over and over in your head will only make it worse. Other things should occupy your time.
  7. Realize that you can’t please everyone. And that it isn’t your job to please everyone. Your job, as a leader, is to be an effective leader with the interests of your enterprise held first and foremost. Not everyone is going to be happy when you have a tough conversation with them. But that shouldn’t stop you. If you follow the principles I’ve outlined here, everyone should walk away from the conversation understanding that there is mutual respect and consideration for all parties, and that the issue wasn’t personal, at all.

What I’ve found, over the course of the past six months, is that with these tools in my back pocket, I’ve been able to confront the issues that face me more easily. I still have significant heartburn about confrontation or difficult conversations, BUT, I know now that I can face them, express myself in a productive way, and usually get the result I need or want out of the situation. And that’s a much better feeling than just being afraid to talk to someone because they might get mad or dislike me in the future.


by Lacy Starling, President and Fearless Leader