The Conversation You’re Avoiding Is Probably the One You Need to Have

Why clarity, kindness, and difficult conversations are part of good leadership.

I don't think of performance feedback as a difficult conversation.

That may sound strange, but when feedback is given with the intent to coach someone and help them be successful, it doesn’t have to feel confrontational. If someone isn’t meeting expectations, they deserve to know. They can’t grow, change or make a different choice if no one is willing to tell them what’s not working.

The conversations I find harder are often the messier ones. Conflict between people. Behaviors affecting a team. Situations where everyone knows something isn’t working, but getting to the crux of why isn’t easy.

Those are also the conversations that can be tempting to put off. I’ve learned that’s usually a mistake.

Nice and kind aren’t the same thing

As leaders, I think we sometimes confuse being nice with being kind.

Being nice can mean avoiding the uncomfortable thing. Giving someone the benefit of the doubt one more time. Softening the message so much that the person doesn’t actually understand it. Hoping a situation will work itself out.

In the moment, that can feel empathetic. But who are we really protecting?

Being kind is about intent. It’s doing what’s best for the person, the team and the organization, even when it’s difficult and even when emotions are likely to come with it.

Sometimes kindness is encouragement and support.

Sometimes kindness is saying, “This isn’t working.”

Being direct is often the kinder and more respectful choice.

The cost of the conversation we’re not having

I’ve learned this one the hard way.

Earlier in my leadership journey, I’ve waited too long to address egos, “diva” behavior or someone who simply wasn’t performing.

There are lots of reasons we do this. Maybe they’re incredibly talented. Maybe we believe we can coach around the behavior. Maybe we don’t have all the information yet. Maybe we want to give someone another opportunity to turn things around.

Or maybe we just don’t want to deal with the conflict.

The problem is that while we’re waiting, the rest of the team is experiencing it.

They’re compensating for the person who isn’t performing. They’re navigating the behaviors we’re avoiding. They’re watching what gets tolerated. And eventually, what started as an issue with one person can begin to change the culture of an entire team.

That’s when I realized that avoiding a difficult conversation isn’t neutral.

Choosing not to address something is still a leadership decision.

And sometimes that decision has a much bigger impact than the uncomfortable conversation would have had.

When is it time to have the conversation?

I don’t believe every disagreement needs to become a big conversation.

People have bad days. Teams disagree. We misunderstand each other. Sometimes something really does work itself out. For me, the threshold is fairly simple.

• Will avoiding this conversation cause harm?

• Will having it remove a barrier or create the opportunity for positive change?

• Can the situation actually improve if we talk about it?

If the answer is yes, I probably need to have the conversation.

Putting it off rarely makes it easier.

Start with the outcome, not the discomfort

One of the books that has influenced how I approach these situations is Difficult Conversations. A lesson I’ve carried with me is to think carefully about what I’m trying to accomplish before I walk into the conversation.

I don’t want the goal to be “give difficult feedback” or “address the conflict.”

What’s the positive change I’m hoping comes from this?

Maybe I want two people to understand each other’s perspectives and find a way to work together. Maybe someone needs to understand how their behavior is affecting the team. Maybe expectations need to be clearer. Or maybe we need to acknowledge that something simply isn’t working.

Starting with the desired outcome changes how I approach the conversation. It moves me away from proving a point and toward trying to improve the situation.

Prepare for the reaction you hope you don’t get

I also spend time thinking about how the conversation might go.

• What’s the best-case scenario? What if the person is receptive and we have a productive conversation?

• And what’s the worst-case scenario?

• What if they’re angry? Defensive? Hurt? What if they disagree completely with my perspective?

I don’t do this because I want to script every possible response. People aren’t that predictable.

I do it because I want to be prepared enough that their reaction doesn’t become my reaction.

If I’ve already considered that someone might become defensive, I’m less likely to be caught off guard when they do. I can stay focused on why we’re having the conversation in the first place.

That matters because difficult conversations aren’t just about saying the difficult thing.

They’re also about making room for the other person’s response.

Agreement isn’t always the goal

I think we sometimes judge difficult conversations by whether everyone walks away agreeing.

That’s not always realistic.

Two thoughtful people can look at the same situation and see it very differently. Someone can disagree with my feedback. I can disagree with their interpretation. Leaders can challenge each other and still have tremendous respect for one another.

For me, a successful conversation is much more about preserving trust while getting to clarity.

• Did we both get to say what needed to be said?

• Did we listen?

• Do we understand each other’s perspective better?

  
  

And most importantly, can we align on how we’re going to move forward?

We don’t have to agree on everything to move forward together.

Clarity is a form of respect

I think this is ultimately why difficult conversations matter so much to me.

People deserve to know where they stand.

If someone isn’t meeting the needs of the team, withholding that information doesn’t give them a chance to change. If there’s conflict between people, ignoring it doesn’t give them a chance to repair the relationship. If a behavior is hurting the team, tolerating it sends a message to everyone else that the behavior is acceptable.

That isn’t kindness.

Kindness is caring enough about someone to tell them what they need to hear, while also caring about how they hear it.

It’s going into the conversation hoping for a better outcome—not hoping to win.

It’s being willing to sit in some discomfort because something better might exist on the other side of it.

And it’s remembering that our responsibility as leaders isn’t to make sure no one ever feels uncomfortable.

It’s to create an environment where people can trust each other enough to have the conversations that help all of us get better.