Becoming Comfortable with Uncomfortable Conversations

Each Monday, PSP has a company-wide conference call. These meetings serve many purposes but learning from one another is one of the most important reasons to hold these meetings.

Not long ago, company President, Brigham Dickinson, said something that was particularly intriguing. He said, “Get comfortable with uncomfortable conversations”. My immediate reaction was, “What? Huh?”.

After some thought, I realized that in business, we frequently must have conversations that are uncomfortable because we are dealing with human beings. We are never going to agree all the times on every issue.

Add to that, when we employ others, we must lead the way to communicate clearly, set goals and guide others to work toward those goals. That doesn’t always happen.

A Tale of Two Employees

Years ago, I worked for a company that was having problems with a couple of people who struggled to work together amicably. In fact, there was so much acrimony between them that those of us who were privy to the situation, avoided dealing with either of them. How was the problem solved? Each of them had a different boss.

The two bosses got together, formed a solution and sat down with the individuals involved. Their solution? Quite genius, really. They were both told that they had 30 days to figure out a way to get along with each other. If they did not accomplish that, they would both be fired. Imagine THAT uncomfortable conversation.

On, Laura Comacho addresses how to become comfortable with uncomfortable conversations by following these steps:

  1. Before having the conversation, write down, specifically, what you want to accomplish with the conversation. Write down the goal.
  2. If you cannot relax, pretend that you are relaxed. Fake it ‘til you make it.
  3. Use contrasting in the conversation. This is what I want. This is what I don’t want.


Still sounds hard? Comacho also suggests that we accept that “you just need to do it”. Either it’s your job as an employer or as a friend. Perhaps you are the only person who CAN have this conversation. Accept that and do it.

Sometimes we worry so much about having to have an uncomfortable conversation that we procrastinate. Far too often, we assume the worst, that the talk won’t go well, that we will make things worse.


Be open to see the situation from the other person’s point of view. Families can be especially challenging when we need to discuss something difficult. Heard a friend say that she and her brother were having a difficult time having an uncomfortable conversation after the death of their parents.

As they talked, her brother brought up a point that she had not considered before. She did not agree but she had a new understanding of where he stood. With this new understanding, they resolved the difference without harming the relationship.

It can also help to have those uncomfortable conversations away from the office. Starbucks, Einstein’s Bagels, Chik-fil-a, during non-peak hours, are all good places to have those conversations. Being away from the office can help both people in the conversation to relax and be more open and honest.

Knowing When to END the Conversation

In politics, we frequently see conversations that go on and on with no resolution or agreement. Knowing when to end the conversation is an essential step when embarking on uncomfortable conversations.

One of the ways to know it’s time to end it is when one party or the other becomes so emotional that they are no longer thinking straight. Emotions can get in the way and rescheduling for a better time can be a helpful tool.

Of course, there are some people for whom there is never a good time to have an uncomfortable conversation. Allow them to own their discomfort, their emotions, their frustration. You remain calm and rational, moving forward as best as possible.

Getting comfortable with uncomfortable conversations can be done when you know how to approach them.

Mary Burkett was born in Southern New Jersey, raised in Southern California, Mary Burkett is a graduate of the University of Utah.

Like many Americans, she has had more than one career, including being a Marketing Director in the shopping center industry, being a coach with Power Selling Pros and owning a Business and Personal Development coaching company.
She has six grown children, expects her 24th grandchild later this year, is active in her community, reads a lot, writes her own personal blog and works on special projects for Power Selling Pros.
Mary and her semi-retired husband live in Southern Utah.