Do I have what it takes to do tough things as a leader?

Three hacks to make your hardest leadership moments (a little) easier

Just imagine. You’re in the room with Vladimir Putin, trying to figure out his next move.

Or you’re sitting across the table from Nobel-award winning physicists, and it’s your call whether or not they get a $17 million telescope.

That’s just a small sampling of the tough decisions and situations Condoleezza Rice has navigated every day of her incredible career, both as U.S. Secretary of State and now as the Director of the Hoover Institution at Stanford.

She joined me last month on my podcast, How Leaders Lead. It’s an incredible conversation, and you owe it to yourself to listen.

But ever since then, I’ve been thinking about the tough decisions leaders have to make.

Of course, they may not involve Russian intelligence or multi-million-dollar space exploration, but every leader has to step up and do hard things – practically every day.

So I thought I’d share some of the best exercises and mental “hacks” I’ve learned over the years to equip you for the toughest situations.

Whether it’s conflict with a team member, letting someone go, or just making a difficult call, I want you to walk into those situations feeling prepared and confident.

So if you’re ready to be the kind of leader who’s ready for the big moments, keep reading. I’ve got three practical strategies you can use to lead well in difficult situations.

Tough situation #1: Making an unpalatable decision

We all love a win/win situation. But sometimes, that’s just not possible. We know whatever choice we make will create a clear winner and a clear loser. Or we find ourselves with only terrible options to choose from.

When we face those kinds of unpalatable decisions, it’s human nature to start procrastinating, overthinking, and second-guessing.

But I’ll level with you: you can’t be a leader unless you can make tough decisions. Some days, that’s just the job.

If you’re dragging your feet on an unpalatable decision, here’s my advice to help you make it and move on.

Try this: Reframing the outcome

Ask yourself this question: “What happens if I don’t make this tough decision?”

See, people make decisions based on two things: pain and pleasure. We want to do what gives us pleasure. We want to avoid what gives us pain.

So lean into the pain. Run through what happens if you don’t take action on this key decision. How will it get worse – for you and for others? When you really spell out the painful effects of inaction, you’ll be motivated to make the decision and get it behind you.

In fact, here’s one possible – and very painful – outcome for leaders who can’t make the tough calls. Someone else is going to make it for you. And eventually, that’s the person who’ll have the leadership role, not you.

Don’t forget: Accountability

If you really want to stop dragging your feet on tough calls, do what Jamie Dimon, the CEO of JPMorgan Chase, does.

Every Sunday night, he makes a list of the tough stuff he’s avoiding. He has trusted people who know what’s on that list. When there’s something difficult that needs to get done, they keep him accountable.

Tough situation #2: Conflict with a defensive team member

We all have to give negative feedback to our team members from time to time. Most people listen, take responsibility, and move forward.

But every once in a while, someone hears that critical feedback and gets defensive. They push back, make excuses, and start pointing fingers.

Suddenly a tough situation has gotten even more precarious. How do you handle it?

Try this: My “Victimitis” exercise

I’ve been in this exact situation. One time, I gave some tough feedback publicly to a president of one of our divisions. It needed to be said, and I'm glad I said it.

But the person who received that feedback did not respond well. Instead of taking responsibility, she came into my office in “woe is me” mode. She was ready to tell me all the reasons I was wrong.

This is the perfect time to use my “Victimitis” exercise. Here’s how it worked in this situation.

I asked my employee to tell me why she was a victim. I told her to lay out everything in her head that made her feel like she’d been wronged by my public feedback.

Next, it was my turn to share why I thought I’d been victimized by her reaction.

Then, I asked her to go back and consider what she could have done differently so she wasn’t a victim.

And I did the same.

When you both look at the situation this way, three things happen.

First, you develop empathy for each other’s viewpoints. Second, you both realize how you could have been more accountable. And third, there’s just something that changes when people listen to themselves complain. They recognize how it sounds, and it cues them to move on from that victim mindset and start taking responsibility for what they could have done differently.

Don’t forget: Vulnerability

The goal of this exercise is to create vulnerability. You want to let that person in on what you’re thinking. Show them you’re not above their criticism. That kind of honesty builds trust. You both walk out with a much better understanding of how to move forward together more productively.

Tough situation #3: Letting someone go

We’ve all tossed and turned at night, thinking about some project or part of our organization.

But in my experience, the business results rarely got to me.

It was the people issues that were the toughest.

Having to look a person in the eyes – someone that you hired – and tell them they’re not cutting it is one of the hardest things I’ve ever done.

In all my time spent interviewing leaders, I’ve never spoken to a single person who found a dismissal conversation easy. They just aren’t.

In fact, a lot of us put off that conversation or even go into denial about it altogether.

So, what mentality shifts can help you use to help you develop the courage you need to let someone go?

Try this: Think of everyone else

When you have to let someone go, think of the greater good.

If a person on a team is performing below the standard, everyone else on that team is usually aware of it, too. By not making the tough call, you’re demotivating everyone else. You’re also signaling that it’s okay to have below-standard performances.

If the person who isn’t performing well is in a leadership role, it’s all the more true. By letting them stay in the job longer, you're penalizing everyone else who works for that person, too.

And finally, imagine what will be different if you can get someone in that role who can really do the job. What kind of growth is possible? What else might change? Focus on the greater good, and you’ll find the courage you need to have that tough conversation.

Don’t forget: Respect

Most of the time, these conversations happen when you’ve got a terrific person who’s just not a terrific fit at your organization. Bring that sense of respect and empathy to that hard conversation. And remember, this is as a tough but necessary step on their path to a role where they can really contribute and shine.

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As a leader, it’s your job to assume responsibility for the tough stuff – conversations, decisions, and conflict.

It’s human nature to avoid them or rationalize them away. And that may work for a little while. But these situations don’t age well. They tend to get worse and snowball if you don’t take action. And eventually, someone else will come along who is willing to step into those tough situations and do what’s hard.

Don’t let that happen to you. Save these mental shifts and exercises. Reference them the next time you face a tough situation. You’ll feel more confident and courageous to lead well, even when it’s hard.

March 7, 2023