Leadership Courage: Having the Hard Conversations You'd Rather Avoid

linnearader
Mar 23
7 min read

Many years ago I worked with someone who had some trouble with their supervisor. It was always something. The supervisor prepared a performance improvement plan and implemented it with this employee and worked their way through it.

Shortly after the PIP was in place, the supervisor started singing graces. They thought the employee did a direct about face and was headed down the right path. Birds sung, sun shone through the air, it was magical.

Then the employee made a mistake. One. Mistake.

The supervisor lost it. They wanted to fire that employee on the spot. They didn't care about the situation, the reasons. They didn't even want to ask questions. They wanted that person fired. Immediately.

I stood my ground and stood against that decision. This termination would have been emotionally driven, not reason. It was a tough stand, but I believe one that was meaningful and the best for everyone involved.

That's courage. Not the absence of fear or discomfort but doing the right thing even when it's hard.

The Hardest Conversation I've Ever Had

I had to fire a friend once. Not like a friend I kind of knew. Like someone I had, at one time, considered a very good friend.

They had made several poor decisions and gone down a bad path or two, or more, and didn't react to correction. It was hard. I lost more hours of sleep than I can count, both before and after.

What made it hard was the people portion of it. Even if they hadn't been my friend, firing someone is very hard. It doesn't matter, even if you don't like the person at all, firing someone is difficult. It's miserable for everyone involved.

I hate firing people. I'm not even a fan of the difficult conversations associated with discipline. What I am a fan of is accountability and I know that as a leader, it's my job to have those difficult conversations whether I like them or not.

In the case of firing my good friend, and in every employment termination, I have to break down the facts of the issue. What do I know. What options do we have. What have we tried. Is there another option that could work.

When it gets to the point where the best option is termination, I have to have that conversation. And while they stink and I'll never get used to having them, getting to the facts of the issue, making sure I'm clear on the decision, and getting to the point relatively quickly are ways to make it easier.

Courage comes from knowing it's the right thing to do, even if it's the hard thing to do.

What happened? It stunk. It wasn't easy. But it was still the right answer to the situation.

Why Waiting Makes It Worse

"I don't want to do something wrong for months. I want to correct it and grow from it immediately."

Here's the thing. Procrastinating having a difficult conversation doesn't make it easier. It actually makes it harder.

Most of the time, the conversations aren't those that I didn't have, because I am not afraid to have a difficult conversation. It's that I waited too long to have it.

Let's use a performance matter as the example. Then let's put ourselves in the shoes of being the person with the performance issue. How would you feel if your boss came to you and told you they've had an issue with the way you've performed for the last six months.

All those days, weeks, months of thinking you're doing a good job, that you're successful, only to find out that you've been making errors for six months. I would be mortified.

So from that perspective, when should you have that conversation? If it's a conversation with me, have it right away. I don't want to do something wrong for months. I want to correct it and grow from it immediately.

And if I'm truly honest, I think most people feel that way. They would rather know they aren't performing up to snuff rather than find out months later.

That takes courage too. Not just having the conversation, but having it when you need to instead of when it's convenient or comfortable.

What Scares Me Most

Having the wrong answer doesn't scare me as a leader. Conflict doesn't scare me either. Public criticism is an everyday occurrence almost, so it doesn't affect me like it used to either.

What scares me is letting my team down.

I do a lot to make sure my team has everything they need. Even when I'm busy, have a ton of irons in the fire, everything is going on at once, what they need matters.

I once had a team member come to me and say my team felt neglected. I. Was. Devastated.

I was in the midst of helping do training and there were lots of different things going on and I'd let my team down. They weren't my focus. That was the worst feeling.

I won't tell you facing that was or has been easy. It's something that can happen easily when things get busy. But it's very important to recognize it. And to have a team that will tell you when it happens.

That took courage on their part to tell me. And it took courage on my part to hear it, accept it, and change.

When Courage Means Standing Alone

Standing alone is tough, but necessary at times.

Going back to that supervisor who wanted to fire the employee on the spot. That wasn't an easy conversation for me to have.

The supervisor was upset. They were emotional. They wanted action. And I was telling them no.

It would have been easier to just go along with it. To let the emotion drive the decision. To take the path of least resistance in that moment.

But that would have been wrong. For the employee. For the organization. For the supervisor, even if they couldn't see it in that moment.

Sometimes courage means standing up against people on your own team. Against decisions that would be easier to just let happen. Against emotional reactions that feel justified in the moment but would cause more damage in the long run.

That's hard. Really hard. But it's part of leadership.

What Courage Isn't

Courage isn't about not being scared. I was scared when I had to fire my friend. I'm scared every time I have to let someone go or have a really difficult conversation.

Courage isn't about being aggressive or confrontational. You can have a hard conversation with kindness and respect. In fact, you should.

Courage isn't about always knowing you're right. Sometimes you have to make the courageous call and then find out later you were wrong. That's okay. You adjust.

Courage is about doing what needs to be done even when you'd rather not. Even when it's uncomfortable. Even when you'll lose sleep over it. Even when it would be easier to avoid it.

Building Your Courage

"Practice on smaller conversations."

If having hard conversations doesn't come naturally to you, here's what helps:

Get to the facts. What do you actually know? What are the real issues? Strip away the emotion and the assumptions and focus on what's true. This makes the conversation clearer and less overwhelming.

Ask yourself what options you have. Is this conversation necessary? What have you tried? What else could work? Sometimes going through this process shows you a different path. Sometimes it confirms you need to have the hard conversation.

Get to the point relatively quickly. Don't drag it out. Don't spend 20 minutes on small talk before you get to the real issue. Respect the other person enough to be direct.

Remember that waiting makes it worse. Every day you avoid the conversation is another day the problem continues. Another day the person doesn't know they need to improve. Another day you're not being honest.

Practice on smaller conversations. Every time you have a mildly uncomfortable conversation instead of avoiding it, you build your courage muscle. Start there and work your way up.

The Gift of Honesty

Here's what I've learned about having hard conversations: they're actually a gift.

When you tell someone they're not performing well, you're giving them the chance to improve. When you address a problem directly instead of letting it fester, you're giving the relationship a chance to survive. When you stand up against a bad decision, you're giving the organization a chance to do better.

It doesn't feel like a gift in the moment. For you or for them. It feels hard and uncomfortable and terrible.

But think about the alternative. Think about letting someone continue down a path that's going to end badly for them. Think about avoiding a conversation for six months while someone thinks they're doing fine. Think about letting emotion drive decisions that will damage people and organizations.

That's not kindness. That's cowardice disguised as kindness.

Real courage is caring enough about people to have the hard conversations. To tell them the truth. To hold them accountable. To stand up for what's right even when it's easier not to.

Why This Matters

Your team needs you to be courageous. They need you to have the hard conversations instead of avoiding them. They need you to stand up for what's right even when it's unpopular. They need you to tell them the truth even when it's uncomfortable.

Because when you don't, when you avoid the hard conversations or let emotion drive decisions or stay silent when you should speak up, you're not protecting anyone. You're just making things worse.

I still hate having to fire people. I still lose sleep over hard conversations. I still get scared that I'm letting my team down.

But I have the conversations anyway. I make the hard calls. I stand up when I need to.

Not because I'm brave. Because it's my job. Because it's the right thing to do. Because courage isn't about not being scared. It's about doing what needs to be done anyway.

That's leadership. And it takes courage every single day.

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Next in the series: Curiosity - Staying Relevant as a Leader

As always, carry social kindness with you everywhere you go. The world needs you and your positive mindset!