Leading Through the Uncomfortable Moments to Achieve Something Greater

In this episode, we’ll chat about how uncomfortable it can be to lead, whether you are leading yourself or others or an entire organization, there’s an inherent discomfort - and an awkward kind of feeling - that comes with leadership. And we’ll talk about the 1 most important thing that keeps us moving forward, through the uncomfortable spaces.

If you’ve led anything (and if you’re listening to this podcast, you definitely have), you know that great things happen when we lead ourselves and others into the discomfort of something new - through the awkward spaces – and to the other side.

I’m going to share with you a couple of recent examples of this that I’ve encountered: one is personal and the other is work related.

I’ll start with the personal example: I have 3 daughters, ages 16, 14, and 8, and I’ve seen each of them grow in their leadership this past week, deal with discomfort, and stay in it until they move through it. 

My middle daughter’s example was one in which she led herself and I'm sharing about it here because the leadership principles are the same as when you’re leading others: Your ability to lead others starts with how well you lead yourself. (Note: my daughter, Laney, gave me permission to share this story with you.)

To set the stage for what happened last week, Laney has been on a hearty journey lately. In April, she told us she is bisexual.

For me, this has been one of the greatest silver-linings of Quarantine because – as she said – everything slowed down so much that she was able to answer this question about herself. She told me later that she’d been wondering about it for years. As a mom, I really only care that she is healthy and happy and with people who treat her well.

Laney is introverted and shy, and in her own quiet way, she is figuring out who she is… discovering what is true for her, and is learning how to stay true. She is beginning to lead her own life.  Last week, she decided to cut her hair short. Coco Chanel once said “a woman who cuts her hair is about to change her life.” I agree with this statement, in essence. I think a woman who decides to go from long to short hair is already in the midst of changing her life and the hair is an outward expression of it.

Yes, I’m talking about a haircut in a leadership podcast, but if you're a woman who has ever gone from long hair to short, you know this is a bold move.

At 2:00 on Friday, Laney had long hair and was excited to get it cut, and at 3:00 on Friday, she had short hair and absolutely loved it. At 7:00 Friday night, she was not so excited, not so in love with it, doubting it, not wanting to leave the house. To me, this is what it’s like sometimes to lead… to make change happen, to lead into the discomfort and move through the awkwardness of it, and keep moving forward.  

The next day, she seemed a little at home with the change… seemed to be settling into her new groove, ventured out of the house, and just kept moving forward.

When we lead a change – with ourselves and others – we don’t do it for the change itself, we do it for something greater. I asked her why she wanted to cut her hair in the first place and (after she said she said, “Because I want to”), she said she wanted to not be weighed down; she wanted to feel freer.

Also in the past week, I’ve started working with someone who is leading a new company-wide initiative. She’s a seasoned leader with a strong track record for producing results. One of her ways of working is to have people who directly, and wholly, work for her, and if she needs more help, she taps on other people around her who are all too willing to help because they like working with her. But these other people don’t report to her; they report to someone else. They have their own designated roles and responsibilities that then don’t happen on time because they’ve been helping this woman.

For years, this way of working has been mostly acceptable, and at times it's been tolerated. If I’d have asked the people who worked with or around her: what’s one thing she does that’s frustrating? They would have said it was this way of working. They’d have also said she got away with it because she’s a great results-producer.

But now, this woman is leading a new company-wide initiative and her decades-old way of working doesn’t work. It 100% does not work. She hit a full-on wall with it and had to face some wide-ranging negative side effects.

I’ve witnessed her questioning if she’s doing things the right way, making the right decisions. ...I know we all have those questions on a daily basis, but there are times, when we’re in the midst of changing ourselves, that the questions and doubt are way more pronounced. It’s an uncomfortable, awkward space to move through.

When I talked with her last week, she spoke for the first time since taking on this new initiative with total clarity about how she needs to work differently with people, in particular, to bring a clear respect to people’s designated roles and responsibilities.

This is like a tiger changing her stripes.

She said that her #1 focus was the success of the company, so she is fundamentally changing how she works with the people around her.

This is when I knew the change will be sustainable because we’re able to move through the discomfort and awkward feelings of change when we are focused on something bigger, greater, that is worth it all.

For this woman executive, it’s the success of the company that she cares deeply about. For my daughter, it’s feeling free.

The thing is, when we change something that’s normal and historical for us, it feels uncomfortable, and awkward at first… maybe for a few days or a few weeks. We can’t tell if we’re doing things right, making the right decisions, how people will think of us. But if we can stay focused on the higher goal, what’s really more important, we can use that focus to pull us through the uncomfortable and awkward spaces to something truly great.