Are you avoiding a tough conversation with someone at work?

As soon as you read that question, someone’s name and face may have come to mind. You might have developed a gnawing feeling in the pit of your stomach. You may have started to sweat or felt your heart rate increase.

If we were honest, many of us would share at least one conversation we’re avoiding at work. As a leader responsible for others, you might have more than one tough conversation you’re putting off.

The Consequences of Avoidance

Have you ever considered the consequences of avoiding that conversation?

-You’re walking on eggshells while you ignore the problems in the relationship.
-You’re hoping other people don’t notice the elephant in the room between you and the other person.
-You’re spending a lot of time (more than you realize) managing around the conversation we’re avoiding.
-You’re hoping the bad situation doesn’t get worse before you’re ready to deal with it.

If we gathered everyone who has read this article and began sharing about the tough conversations we’re avoiding, I think we’d be surprised by what we heard. While the characters involved might be different, the scenarios would have a lot in common.

Why We Avoid Tough Conversations

There’s a payoff for avoiding tough conversations and a pathology to our thinking as leaders.

Why We Avoid Tough ConversationsWe think we have too much to lose.

Many of us avoid the conversations because we’re afraid. We might not struggle the teeth-chattering kind of fear, but we are scared to have a tough conversation. The potential fallout of a negative reaction or outcome is too much to bear. So, in the words of one leader, we avoid the conversation and trade short-term discomfort for long-term dysfunction.

We have negative experiences in the past.

If we’ve been in a tough conversation, which went poorly, we may not want to repeat the experience. We often let one or two negative experiences prevent us from ever getting to a positive experience.

We haven’t been trained in or seen healthy modeling for successful tough conversations.
It’s tough to teach this stuff in a college classroom. Too few of us have mentors who showed us the way in this area. We feel like we’re walking blind and alone into these situations. We don’t know what we’re doing, and we don’t know whom to turn to for assistance.

We work in a passive-aggressive culture where confrontation is devalued or avoided.

For years, I avoided tough conversations with those I oversaw because my organization did not reward me for leading in this manner. I knew the outcomes, which were possible from those tough conversations, and I knew I didn’t have support to lead through them.

We come from a family environment, which predisposed us to avoid confrontation or abuse one another.

Many of us grew up in families, which either fought poorly or avoided fighting entirely. We didn’t learn how to have a tough conversation about issues and ideas without making attacks on people. If we don’t have experience to draw from or we want to avoid becoming like our families in this area, we may avoid these conversations entirely.

We make hope into a strategy.

We naively hope things will improve in the future. The problem is hope is not a strategy. It’s a helpful mindset for a leader, but our strategy for leading others needs to be motivated by hope, not completely defined as hope. Without an aligned action plan, hope is a lackluster option in the face of problematic behavior or an unsustainable action by one of our team members.

My Greatest Regrets as a Leader

I’m a young leader, so you might wonder if I have led long enough to have regrets. And the answer is I have! My experience has validated what we know about regret from research.

From experience, we know regret becomes more powerful (and even paralyzing or crushing) when we feel like we have decreasing resources or opportunities. This is the lesson the research of Cornell social psychologists, Tom Gilovich and Vicki Medvec, confirms for us. Gilovich and Medvec found the nature of what we regret changes over time. In the short term, we obsess over failure. These would be bad decisions, choices when we were young and stupid, and moments we didn’t achieve our goals.

As a leader, my greatest regrets are the conversations I didn’t have, not the ones that went poorly.


However, in the long term, regret shifts away from failures, and we begin to lose sleep over missed opportunities. By the time we’re in the final years of our lives, we don’t regret the shots we missed – we regret the ones we didn’t take.

As a leader, my greatest regrets are the conversations I didn’t have, not the ones that went poorly. I regret the times I chickened out and didn’t have a tough conversation, which could’ve helped our team or changed the trajectory of someone’s work. I wish I had more courage and urgency in those moments. The taste those memories leave in my mouth motivates me, even as I type these words today.

The Truth About Tough Conversations

Let’s be totally honest. Do those tough conversations ever go away when we ignore or avoid them? 99.99% of the time, the answer is no. They linger and worsen over time. It is incumbent on us as leaders to jump into them, even if we’re scared and feel inadequate.

One of the things I’ve learned about tough conversations is when a leader is avoiding them, the people under that leader are watching and waiting for the tough conversation to happen. I learned this later in my leadership journey than I’d like to admit. I had no idea people were waiting on me to lead because they were directly or indirectly being impacted by fear of confrontation. Then, I remembered leaders I followed who I lost respect for when they avoided tough conversations. Shocked, I realized I was at risk of becoming that leader myself.

Tough conversations are tough, hence the name! But they can be a win for everyone. I recently wrote an article for my personal website, 10 Ways to Make Tough Conversations a Win for Everyone, based on recent experience and reading in my personal leadership.

In my first year of being the senior leader in my organization, I’ve had more tough conversations than any other year in my life. And while I haven’t led in all of those perfectly, I’ve been surprised how many of them led to positive outcomes for everyone involved.

What Tough Conversation Do You Need to Have Today?

I cannot guarantee the conversation you’ve been thinking about as you read this article is going to end well. All of your worst fears may actually come true. The person could blow up; lash out at you and the organization. They could make things worse, not better. You could lose your temper and not lead the conversation in a healthy manner. You might need to bring your supervisor or HR into the conversation and create more work for yourself.

But I wonder if you’d respect yourself more as a leader afterward. I wonder if someone on your team would come knocking on your door to say thank you, sharing why they appreciate having a leader who has the courage to do hard things. Maybe your team dynamics would improve with that behavior pattern addressed or that problem member working for another department or organization. Maybe performance would improve with workarounds eliminated.

If you’re avoiding a tough conversation, I encourage you to take four steps today.

  1. Name the tough conversation you need to have.
  2. Invite someone to hold you accountable for taking action and tell them when you’re taking action.
  3. Begin preparing for the conversation. (Check out my ten-point checklist.)
  4. Initiate contact with the person(s) and have the conversation.

Tough conversations are never easy. But they never get better by avoidance, and this is why we are leaders. We serve others with courage and compassion, even when we’re afraid!

Photo by Dmitry Ratushny on Unsplash


Writer Scott Savages takes a look at why we avoid tough conversations and how leaders can stop avoiding and start talking.