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Leaders Must Become Comfortable With Being Uncomfortable

September was a great start to my fall, hopefully it was for you, too.

It was a great start for me because I got to offer my favorite program to two different groups, “Influencing With Integrity & Confrontation Without Conflict.”

In both training programs, which combined totalled about 40 people, most everyone agreed that the strategies I was teaching and asking the participants to practice and apply in their leadership roles were difficult and made them “uncomfortable.”

Both the “Influencing” and “Confrontation” programs teach participants how to create a relationship in which challenging conversations can take place, and then we provide actual verbiage and scripting to facilitate those discussions.

But, again, everyone agreed even with those tools, the conversations were often, still uncomfortable. There is no doubt about it, they are.

Last week my colleague, Jim Smith, the co-creator and my partner in “The Leadership Series” product, wrote a blog post titled, “If You’re Not Uncomfortable, You’re Not Leading.” (with his permission his blog post is reprinted below)


People don’t like to be uncomfortable. I cannot recall the last time I had a conversation a leader where the subject of “difficult conversations” about performance did not come up as one of their most feared situations. Second to that is concern about telling people that “change is coming.” Meanwhile, we face the reality that forward progress inevitably requires change, and change itself is uncomfortable. What’s a leader to do?

If you want to be effective as a leader, you’ve got to get over yourself. While you may prefer to spend all your time in a happy, comfortable world where everyone does their job well and processes always work, that is, in the end, a fantasy world in which your role is unnecessary. The raison d’être – the core justification – for your job is to solve problems, to declare new futures, to reallocate resources, and to name the elephants in the room.

In other words, your role by definition requires that you create discomfort, both for you and for others. I’m not advocating for “control freaks” or for those with anger issues to run amok in the workplace, because those behaviors create a dysfunctional form of discomfort. I’m simply reminding you that you must, in today’s fast-moving world, continually stir the pot of change, and regularly challenge your team members to step up their game – and hold people accountable for delivering on their commitments.

In order to create discomfort, you must regularly practice that emotional state; you must become friends with unease, concern, nervousness, and even trepidation. When you become intentionally familiar with those emotions in small doses, you will gradually strengthen your ability to manage them. You will find yourself more capable of holding difficult conversations because you’ll be confident in your ability to “live through the experience.

How do you “practice” feeling comfortable with discomfort?

1. Start by having small conversations about minor concerns. Address little performance issues as they occur, so that the conversations can be about improvement versus “your job is in jeopardy.”

2. Rehearse your conversations with a coach or colleague. Many times the fear of delivering a difficult message dissipates when you speak it aloud in a practice session – so by the time you have the ‘real’ conversation, your system is already used to the message.

3. When a change is imminent, start talking with people about the high-level issues and direction even before you know all the details. By the time the final details emerge you and the team will have already gotten gradually used to the idea(s).

4. Have difficult conversations as quickly as you can after an issue emerges. 90%+ of the “drama” and discomfort comes not from the issue but from your thinking (and thinking and thinking) about it, and creating stories about what might happen. Act before your imagination freaks you out.

Remember: Leadership is not about a title. Anyone can be a leader who can step into the discomfort of a difficult conversation, knowing that on the other side of that discomfort lays greater potential for progress, accomplishment, and a more positive workplace experience.


’til next time, make it a great week!

skip weisman, helping leaders motivate employees to improve organizational performance

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