3 Scary Moments Every Leader Faces

Forget ghosts and goblins! 👻 👹 Here’s how to overcome the leadership challenges that really keep you up at night.

Happy Halloween!

How are you celebrating today? Are you going to hand out candy to a few adorable ghosts and goblins? Or maybe you’ve got plans to watch your favorite zombie movie!

It’s a fun day for all things eerie and scary. But for leaders, it’s not the thought of ghosts and goblins that keeps us up at night.

Leadership comes with plenty of frightening moments—no zombies required!

After all, the very definition of leadership requires us to forge a path into the unknown.

Today, I want to walk you through the three leadership situations that can feel a little frightening.

Stay in a leadership role long enough, and I can guarantee you’ll face one (if not all!) of these.

But these “scary” moments of leadership don’t have to fill you with fear. In this article, I want to arm you with insights and strategies so you feel ready to overcome them.

That way, when one of these situations pops up, you won’t feel afraid. You’ll feel prepared and confident that you’ve got what it takes to manage it well.

Let’s jump in!

1. Letting Someone Go

One of the toughest things you have to do as a leader is to let someone go, especially when it’s a talented person.

I faced this “scary” situation a few times in my career when my company was restructuring and reducing costs.

And I’ll be honest: there is no advice in the world that can make letting a good person go feel “easy.” It’s just not possible.

But I can give you a few tips I’ve learned to help you lead well in these moments.

First, be direct. Take the time to gather your thoughts ahead of time so you can communicate succinctly and clearly. In tough conversations like these, clarity is kindness.

Second, let the person know why the decision is being made. Be honest and transparent as you talk about the factors that are driving the decision.

Third, be kind. Share one or two meaningful things you admire about that person’s work. If it’s appropriate, offer specific ways you can help them land on their feet, whether that’s through a reference or your own network.

Finally, leave space to listen. The person sitting across from you may have questions or frustrations to voice. Be present as they talk. Resist the urge to start preparing your response in your head. If you’re not sure how to answer, it’s okay to simply say as much. Just make sure you follow up later.

Of course, it’s also tough to fire someone for performance reasons. That’s why I devoted an entire article to it earlier this year. Read “Is It Time to Fire that Person?” here!

2. Navigating a Crisis

By their very definition, crises are unpredictable. You never know when they’re going to pop up, and that makes them scary!

But here’s a harsh reality: when it comes to crises in leadership, it’s not a matter of if they happen. It’s when.

That’s why I’m so grateful for my friend Jonathan Blum. He’s one of the foremost experts on crisis management. He was the Senior VP of Public Affairs for Yum! Brands, where he and I worked together, and he even served in the Carter administration.

He was kind enough to join me for a conversation during the COVID-19 pandemic to help leaders respond and serve their teams well.

His three rules of crisis management apply to all kinds of crisis situations. Understand these rules today, and you’ll be ready to lead your team well whenever the unexpected arises.

Here they are:

First, be truthful and say what happened. A lot of leaders make the mistake of being too vague or oblique about the situation. As Jonathan puts it, “People will forgive you if you’re honest with them and tell them the truth.”

Next, say what you’re doing about it. According to Jonathan, you’ve got to be specific. Get into the details and share what actions you’re taking to mitigate the situation.

Finally, say how you’re going to prevent it from happening going forward. Lay out a clear action plan so you give people some assurance that you won’t have the same issue again in the future.

It’s a simple playbook, but it’s incredibly effective. The crisis itself will be difficult, of course, but knowing these rules will help you feel prepared (not scared) to be a steady hand at the wheel.

3. Giving a Big Speech

Did you know that America’s biggest phobia isn’t creepy clowns or zombies?

It’s public speaking!

About 25% of Americans say they’re afraid of getting up in front of a crowd to speak.

If you count yourself in that number, I can relate. These days, I love getting up in front of a crowd, but that wasn’t always the case.

Early in my career, I gave my first big business presentation. I was so nervous. I got in that room and must have said “you know” a million times. I kept telling stupid jokes to try to relax, but that just made it worse. I was truly terrible, and I knew it.

To be honest, it took me years to get over it.

But eventually, I did. How? Well, I hired a coach to help me, and it was a game changer. If you fear public speaking, invest in some coaching. He or she can help you build your know-how, face your fear, and boost your confidence.

My other piece of advice comes from Jessica Kim, the co-founder and CEO of ianacare, when she joined me on my podcast, How Leaders Lead.

“When you are public speaking,” she told me, “you are really just reaching other people's hearts. It's not necessarily the exact words that you are sharing, or how you articulate it. But it's actually the feeling that people have when they listen to you.”

Focus on the opportunity you have to share your audience. Consider the time and effort they took to be there, and lean into the opportunity you’ve been given to help them move forward.

When you reframe public speaking as an opportunity to connect with people and serve them, it can help you find the calmness and confidence you need to deliver a great talk.

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Leadership is inherently full of uncertainty.

In every tough decision and new strategy, you’re always venturing into the unknown.

That’s why so much of a leader’s job can feel scary.

But situations feel a lot scarier when we’re not prepared for them.

So if you’re reading this, you deserve BIG kudos! You’re investing in your own development by reading and learning from other leaders. I hope these insights boost your confidence and make all that “unknown” stuff feel a little more “known” (and a lot less scary as a result.)

Learning and preparation are key, but they’re also not quite enough.

You also need courage—and lots of it.

True leadership thrives on courage.

In every scenario I’ve talked about today—letting someone go, leading in a crisis, walking on stage—you’ll face that still, small moment where it’s up to you to take a deep breath and step into the unknown.

It's not about the absence of fear but the triumph over it! So cultivate your courage, too, and you’ll inspire and empower others to go along with you.

Now, I’d love to hear from you! What’s the scariest moment you’ve faced in leadership, and what did you learn?

Share your thoughts in the comments so I can learn from YOU!

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