6 Uncomfortable Leadership Decisions

The longer you’re in a leadership position, the more decisions you will have to make. These decisions… They’re not always going to be easy.

In fact, many of the decisions you’re going to make as a leader will be uncomfortable.

Your decisions become uncomfortable when they impact the livelihood of those you lead, the organization’s health, and more. The decisions keep coming; the uncomfortableness keeps piling on.

6 Uncomfortable Leadership Decisions

What uncomfortable decisions may come your way? I’ve found many common decisions aren’t easy to make. They’ll make you squirm, procrastinate, and maybe even cry to your momma.

Let’s look at 6 of these leadership decisions you’ll face.

1. Firing an employee:

We may think that firing an underperforming employee will be the easiest decision to make. It’s not.

You may empathize with the employee and their situation. There’s an understanding that someone will hurt while trying to find a new position.

Yet, two things happen when you have to let an employee go.

The first: You free up your team to move forward. Sometimes, these underperforming employees are not holding themselves back; they’re holding the whole team back.

The second: You free the employee up to find a career path that fits them. Often, a fired employee will see your actions as the blessing they need. You allowed them to get out and experience something new.

While firing an employee is an uncomfortable decision, it’s a decision you’ll have to make.

2. Allowing your team to fail:

No one wants their team to fail. You want to see success after success.

Yet, there will be times when your team makes a wrong decision. They’re going to find themselves struggling and there’s nothing you can do to help them.

This is a time you’ll have to let your team fail.

The good news is that failure isn’t fatal. Failure is a time to learn and grow and find ways to improve.

Help your team see the positive side of failing.

3. Staying the course:

You’ve made a decision. The decision seemed like the right one at the time you made it. It still does, but it’s causing issues.

You now have an uncomfortable decision to make. Do you stay the course or do you change directions?

Changing directions is easy when things are difficult. Staying the course is uncomfortable when you know there’s an easier way.

However, staying the course can lead to outstanding outcomes. Don’t change directions just because the course you’re on is uncomfortable.

4. Telling the truth:

Telling the truth should be simple. You tell it like it is, right?


Telling the truth can be very uncomfortable. Think about when your boss has greenery stuck in her teeth. Do you tell her immediately, try to find a polite way to let her know, or ignore the situation?

The truth isn’t always comfortable. However, the truth is always appropriate.

5. Setting deadlines:

I hate setting deadlines. Yet, I know that deadlines help us get things done.

The decision can be uncomfortable when we place a timeframe around a project. You may feel like you don’t have all the information or freak out if the project goes over.

A deadline is a good thing. Remember that. A deadline is uncomfortable to set but it is easier to decide when you realize the deadline can be flexible!

6. Evaluating yourself:

This may be the most uncomfortable decision you have to make. Evaluating yourself can be extremely difficult.

We see through tinted glasses when we look at ourselves. All of our perfections fade away and we’re blemish free. Now, we look at someone else and the blemishes are front and center.

Remember this when you go to evaluate yourself. You’re more likely to forgive your faults than you are of others.

Be uncomfortable. Look at yourself through a truth-filled lens. Be willing to accept the uncomfortable truth that you need to improve.

Make The Uncomfortable Decisions

Just because a decision is uncomfortable doesn’t mean you don’t need to make the decision. Stop putting off the difficult decision and make a move. You’ll be glad you did. Not only will you have chosen action, but you will also have moved forward. Stop letting uncomfortable decisions hold you back.

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