3 Strategies To Overcome The Uncomfortable Parts of Leadership

Motorcycle approaching a turn in the road


My husband and I took a two-week motorcycle trip out west in August.  With plenty of seat time to think, I discovered four unexpected leadership lessons that seem particularly relevant as we are preparing for life in the Next Normal. This is lesson #4.   Links to previous lessons can be found at the bottom of this post. Read Lesson 1.


Riding nearly 3,000 miles on a motorcycle isn't the most comfortable way to travel, especially when you're the one on the back.  I'd be lying if I didn't tell you that I had more than a little stiffness in the back and legs along with some numbness in the seat on this trip.


But there are plenty of reasons why it was worth it:

  • You're more in touch with your surroundings. You notice things you wouldn't otherwise. The sights, sounds and smells along the way are much more intense.
  •  You have greater freedom.  Because a bike is so nimble, you can easily navigate roads other vehicles have difficulty with. You have more options for the roads you take and can make last-minute adjustments to avoid traffic.
  • Your load is lighter. Since you can't fit a lot in motorcycle saddlebags, packing is pretty simple and a lot less stressful. 

I thought about this notion of comfortableness and had to admit that I had worried about this in advance. How would I stay warm or cool enough? What if it rained (or snowed, which it did one day)? Could I make it the whole two weeks riding as much as nine hours a day on the bike? 


While it helps to think about these things in advance to plan appropriately, the worry was unfounded.  We packed for changing weather, we took breaks throughout the day whenever we wanted them, and at some point, I simply adapted. 


Being comfortable is not the goal


It made me think of how much we worry about being uncomfortable in life and leadership and, perhaps, how misplaced that worry is. It's human nature to seek a pleasant path, of course. But being comfortable is not the goal of leadership. And it shouldn't be our focus.


If you're like me, I suspect there are many times as a leader you've been tempted to prioritize being comfortable over a lot of other things:

  • Avoiding conflict even though it would be more helpful to address it;
  • Saying something nice instead of saying what needs to be said;
  • Playing it safe instead of taking a risk that might be a game-changer.

I can recall many sleepless nights I've had, lying awake for hours thinking through a difficult decision or complex situation I needed to deal with. Inevitably I would wonder if there wasn't an easier solution – those options always seemed a lot more attractive! But in the end, I knew they weren't the best ones. 


Almost always, the bigger challenge was accepting that I needed to forgo feeling comfortable in order to do the right thing.


Choosing a more comfortable path isn't necessarily wrong. But most of the time it's not the most productive option. And many times, it can make matters worse:

  • The conflict you put off resolving today can escalate into the loss of a client.
  • By softening your words too much, an employee never fixes a problem that is derailing their career.
  • The safer choice can lead to irrelevance for you, your team and even your organization.

What you gain by being uncomfortable

It's ideal when you can enjoy being a leader. But leadership often means you must do hard things, make difficult decisions and accept responsibility when things go wrong.


I am confident you have come to grips with this reality long ago, and you are probably even more aware of this requirement of leaders now. 2020 certainly brought more than its share of discomfort to leaders everywhere. 


But I am also confident you have realized some significant benefits for yourself and your team this year as a result of your willingness to lead in exceedingly uncomfortable times:

  • You've developed new capabilities – and empowered others to do the same.
  • You've allowed your courage to elevate your thinking instead of letting your fears to limit it.
  • You've discovered how resilient you can be and inspired those around you to rise to the challenge.
  •  You've helped others envision a brighter future – and showed them how to make it a reality.

As you look ahead, I'd like to share three ways you can continue to deal with the inevitable discomforts of leadership, particularly as you plan for the Next Normal. I hope these practical strategies are useful not only for your own day-to-day leadership but also as you coach your team to hang in there through the uncomfortableness of this unique moment. 


1.     Lead with a growth mindset

Very often leaders shrink back from uncomfortable situations out of fear. They hesitate to make a difficult decision for fear of being judged or criticized. They are unwilling to move outside their comfort zone because they may look foolish in their attempt. Or perhaps they fear making a mistake is a commentary on their intelligence. 


These are fears that stem from a fixed mindset, or the belief that our abilities and intellect cannot be markedly improved, so therefore we should avoid being in situations that make us uncomfortable.


As we so often learn, our fears are largely unfounded and driven by our inner critic. A fixed mindset holds us back from leading courageously. By adopting a growth mindset, you can learn to view challenges differently and tackle them with greater confidence. 


Growth mindset, a term coined by Stanford professor and psychologist Carol Dweck, is the understanding that your skills and abilities can change. Working through difficult situations can help you learn and grow. Being willing to be uncomfortable can offer an opportunity to develop new skills or become more resilient.


Here are a few strategies that will help you adopt a growth mindset in uncomfortable situations and allow you to lead with more courage and confidence.

Develop an if/then statement

It can be helpful to plan in advance what you will do in a difficult situation so you can move forward in spite of any hesitations.  For example: "If I'm worried about getting push-back for a difficult decision I need to make, then I will remind myself that earning self-respect is more important than seeking approval from others."


Ask yourself one question

Instead of telling yourself "I'm not good at this," ask "What am I missing?" The shift will open your mind to help you see potential where you couldn't before.


Try a new path

Drawing inspiration from motorcycling, when one strategy isn't getting you where you want to go, try a different route to get there. Almost always, you have more options than you think you do. 


2. Stay close to the front lines of your business

It can be hard to know what's going on in your business in times of uncertainty. Signals are confusing, rules are changing, and your attention is often divided between multiple crises happening sometimes all at once. Uncertainty breeds uncomfortableness.


In these situations, it is tempting to rely on your team to deal with the nitty-gritty so you can stay clear of the chaos happening on the front lines. While you want to empower your team to help you make sense of what's happening, you must stay close to the front lines yourself. If you don't, you'll miss sensing important shifts that could substantially impact your company's future.


Plus, you bring some valuable things to the table in uncertain and uncomfortable situations:

  • More than your team does, you see broadly across the business and have the advantage of this more strategic perspective.
  • Likely you have wisdom and institutional knowledge that could bring forward lessons learned from similar situations.
  • Best of all, you have an opportunity to coach your team by asking them good questions that allow them to discover and leverage their own insights.


Here are a few suggestions for how you can stay close to the front lines and more in touch with what's going on.

Check-in with key clients 

Schedule a top-to-top call/video meeting periodically to ask what their pain points are and what you can do for them professionally or personally. 


Review ongoing customer feedback

Access regular feedback through call centers, customer-service platforms, or social media. Look for patterns, emerging topics, or trends that could spark a new use for a product or service.

  • Get some perspective – Talk to friendly industry colleagues to compare experiences and find out what's working for them. It can be helpful to know how others are dealing with similar situations.
  • Shadow your front-line team members – Not that you want to do this often, but every now and then it could help you to hear what they are hearing and debrief with them on new ideas or solutions.


3.     Get clear about your purpose. 


2020 has been a challenging year. But it has also been a time of meaningful reflection for many leaders to consider how and why they lead. If it's this hard, is it really worth it?


One thing is clear: It can't be all about the money, fame and power. These things are nice and they are just rewards for the hard work of leadership. But they don't always materialize. If they do, they don't last. And ultimately, they don't satisfy. There must be something more.


The more meaningful rewards of leadership are the intrinsic ones – the chance to have an impact, to be a catalyst, to make positive change, to create something from nothing, to feel a sense of satisfaction from achieving challenging goals. Sometimes these rewards require you to be uncomfortable in the process. But they are well worth whatever discomfort must be endured.


One of the best strategies for dealing with the challenges of leadership is having a clear sense of purpose about why you lead. If you're not sure, take a moment to answer these questions:

  • What do I want my legacy as a leader to be?
  • What intrinsic rewards are motivating to me?
  • What is my ultimate destination as a leader and am I on the right path to get there?


These questions allow you to step back and think more broadly about your leadership journey.  I hope they help you clarify your purpose for leading and allow you to see the positive impact and influence you can have – not only on your team and your organization, but also on your community, your industry and the world.


If you haven't already, I encourage you to read the first three installments in this series. Part one, 4 Unexpected Ways to Navigate the Next Normal, part two, We Grow Most When We Are Challenged: Practical Ways to Expand Your Leadership Skills For the Next Normal and part three, The Greatest Potential Lies in the Less Obvious


Written By

Elise Mitchell

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