How To Train Yourself To Excel In Uncomfortable Situations

Over time, leaders learn to stretch their comfort levels and modify circumstances to make tricky situations less tricky.

How To Train Yourself To Excel In Uncomfortable Situations
[Photo: Benoit Daoust via Shutterstock]

We’ve all been there: You’re feeling out of your comfort zone at work. Your face is flushed, your heart is racing, and your mind is a jumble. Everyone’s waiting for you to get it together. Then someone else jumps in, taking control with confidence and utter calm.


Why are you so flustered while some of your colleagues can handle these situations with grace? Chances are they feel many of the same emotions. The difference is just that they’ve learned to get comfortable with the uncomfortable. That takes practice, not inborn talent. Over time, leaders learn to stretch their comfort levels and modify their environments so it’s easier to respond to tricky situations. This enables them to manage tough circumstances better and to spot and confront challenges earlier. Here are three steps to help you do all that.

1. Surround Yourself With Diverse Thinkers

It’s easy to isolate yourself in a “good news cocoon” where everyone says things are fine and no one challenges your ideas or asks tough questions. This can be a comfy position, but it’ll be short-lived. When team members aren’t free to ask difficult questions, the organization and its leader develop dangerous blind spots. Encourage challenges to your judgment, don’t shirk from them. Leaders who invite probing questions are much better equipped to manage threats and spot opportunities.

In a recent interview for the MIT Leadership Center video series, David Markert, director of business development at Progeny Systems, told me that identifying those you can count on to challenge you starts with a simple, honest self-evaluation. What are your strengths and weaknesses? Where are your blind spots? If you can answer these questions, you’ll be more apt to recognize people who can help you fill the gaps. You can rely on them to think differently and offer fresh solutions.

2. Probe Your Assumptions

Early European sailors exploring the American West traveled up the Gulf of California. They assumed–because of its length–that the gulf stretched all the way through the continent, making California an island. Confident of this, the explorers turned around and reported their findings back home. Thrilled with the new discovery, European royalty declared California an island and had cartographers draw it accordingly.

Image: Stanford Libraries via Stanford News

A few years later, other explorers found that California was in fact connected with the larger North American continent. But since it was frowned upon to challenge royalty at the time, it took another 100 years for cartographers to connect California back to the mainland.

Whether royalty or a C-suite executive, leaders should urge team members to challenge them. Jason Whaley, CEO of Manus Biosynthesis, admitted to his employees that he sometimes jumps to conclusions. Whenever Whaley or another team member suspects that’s happening in the course of a conversation, they’re empowered to interject, “Already listening!” The phrase is a verbal cue that prompts everybody to take a step back, reset, and move forward with an open mind. “Just having a label for it makes it easier to identify, diagnose, and do something about it,” Whaley says.

It may feel uncomfortable at first, but by acknowledging biases and misguided judgments–and by giving employees the language and autonomy to surmount them–leaders like Whaley reduce the risk of making errors as big and intractable as thinking California an island.

3. Commit To The Uncomfortable

It’s only by extensive training and experience that firefighters manage to perform with clarity and precision in life-threatening circumstances. Business leaders seldom, if ever, do anything as deadly as racing into a burning building, but there’s no reason they shouldn’t take a similar approach to self-preparation. Volunteer for projects that are especially challenging–those where you know your current strengths and experiences won’t help you much. You’ll have to learn how to put out fires, so to speak, in real time, and you’ll get better with practice.


Manijeh Goldberg, CEO of Privo Technologies, shares with me that by learning to be a “firefighter,” she developed the capacity to be comfortable with almost anything. She often volunteered for the projects nobody else wanted–the ones where, she says, “it should have been done yesterday, it’s late, and people aren’t getting along.” But over time she learned to handle these situations by saying, “Everybody, let’s be transparent. This is where we are; let’s try to make it work.”

Willingly seeking out the uncomfortable is hard. It might make you sweat and shake your confidence in the leadership qualities where you excel. But that’s precisely the point. The more you offer yourself measured doses of unfamiliar, high-pressure experiences, the better your chances of overcoming them. After all, chances are your next real-life, heart-racing situation is just around the corner. Run to meet it.

Hal Gregersen is executive director of the MIT Leadership Center and a senior lecturer in leadership and innovation at the MIT Sloan School of Management. He is the author of the bestselling The Innovator’s DNA.