What Great Leaders Struggle With – But Are Scared to Admit

I recently gave a keynote to a room filled with hundreds of leaders from around the world. These were people with prestigious positions and reputations for excellence, and I was humbled and honored to be in their presence.

After my keynote a crowd gathered at the back of the room, where I was signing my new book. Speaking with these accomplished leaders one on one, I began to notice a pattern. Many of them were using the content of my talk as a springboard to talk about their struggles—struggles they were scared to admit to others, especially their colleagues, their teammates, and their boards. The nature of their struggles fell into a few broad categories.

1. They were grappling with loneliness and isolation. We think of business leaders as being surrounded by people all the time, but the old adage is true—it really is lonely at the top. In a recent study, 61 percent of C-suite leaders believed isolation hindered their performance. That’s a significant proportion of top executives who are suffering—and not performing at their peak. The sense of isolation is even more pronounced, and its effects more significant, during challenging times. Those who are dealing with loneliness and isolation need to know they aren’t alone. Finding ways to let people in may mean overcoming the myth that we need to do it alone, but it’s the best cure for loneliness and isolation.

2. They were wrestling with self-doubt and feelings of inadequacy. From time to time we all feel inadequate. or suffer from self -doubt, but leaders tend to see it through the lens of their team and the others who are counting on them, and it leaves very little room for even questioning yourself. In an unfamiliar situation or one with no easy answers, even if they have the necessary skills to arrive at a solution, they may start to question and mistrust themselves. As I discuss in my latest book, The Leadership Gap, tapping into your capabilities and competencies can provide the confidence you need to overcome times of self-doubt.

3. They were fearful of letting people down. Like the rest of us, most leaders ascribe to a set of rules and standards, and they hope people are pleased with the work they do. But if it’s done right, leadership involves risk and courageous decisions, and one of the hazards is that sometimes you let others down and have to face their disapproval. Especially when you’re trying to achieve something significant, it’s important to remember that you can’t always please others (or even yourself) and free yourself to make tough choices in light of the big-picture priorities and your goals for your team and organization.

4. They were afraid of public failure. We may teach that failure is a component of eventual success—and it is—but it’s still something that everyone dreads. And when you fail as a leader, you fail big. Especially for a group of people who tend to have healthy egos, it can be rough. It may be easier said than done, but when you’ve wiped out is the time to get out of your own head and look objectively at failure as a learning experience.

5. They were scrambling to get everything accomplished. We all tend to have a lot to do on any given day. That daily pressure is magnified for leaders, who have their own things to accomplish and have to make sure everyone on their team is performing well. It’s a big burden, and the only way through is to focus on what you need to accomplish as a leader, do it with excellence and make sure you are surrounded by the right people doing their right jobs in the right way.

6. They were laboring over their weaknesses. Most people hate to admit they have weaknesses. My keynote took this as a topic, with the gist being that while most leaders are working to find their strengths, I’m a big believer in identifying your weaknesses and leveraging them. That same message is an important part of The Leadership Gap.

7. They struggled with criticism. Leaders learn early on that everyone has an opinion about their actions and thoughts. All feedback is good, but it’s hard to listen to critical opinions, especially when they seem poorly thought through or mean spirited. As a leader, you need people to share information with you, and that means managing your emotions when you hear things seem unfair.

8. They were wrestling with the best way to handle confrontation. Few of us enjoy confrontation, but it’s a necessary skill if you want to challenge those you lead. The reality of leadership is that there are times when you have disagreements where you have to stand up and challenge someone. Confrontation is where the skill of true leadership lies, because the best leaders learn how to question and tackle challenge with a humble and sincere approach.

What I came to realize that day is that it doesn’t matter what position you have or whether you lead a team of one or a company of thousands. Struggle is a part of leadership, it brings lessons to be learned and opportunities to be shared. If you can find meaning in your struggle you will succeed as a leader.

Lead from within: When leaders can battle the struggles of the present they will learn to unlock the success in their future.


N A T I O N A L   B E S T S E L L E R

THE LEADERSHIP GAP

What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Photo Credit: Getty Images


Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness is being released by Portfolio May 2017.

6 Responses to “What Great Leaders Struggle With – But Are Scared to Admit”

  1. MaryAnn Means-Dufrene

    16. Jan, 2018

    Lolly, thank you for this post. It’s interesting to hear top executives’ reactions to your book. I’m a little over halfway through The Leadership Gap right now and am really identifying with a couple of the archetypes. My response to these 8 common issues leaders are grappling with: Every leader really needs an executive coach!

    Thank you for your important work.

    MaryAnn

    Reply to this comment
    • lollydaskal

      17. Jan, 2018

      Mary Ann, Thanks for your comment, well everyone can use a coach regardless of their position. Don’t you think? Lolly

      Reply to this comment
    • lollydaskal

      21. Jan, 2018

      MaryAnn Thanks for leaving a comment, The Leadership Gap is written about CEO’s but it’s really all our struggles.

      Reply to this comment
  2. Ron MacKnight

    19. Feb, 2018

    “If you can find meaning in your struggle you will succeed as a leader.”

    This one sentence stood out as I completed reading your article. I, like many others, have been led to believe many of the struggles we face as emergency services leaders are unilateral in nature. However, as one grows professionally, it is incumbent upon us to distance ourselves from dogmatic thinking, embrace the struggles, and see them as valuable lessons. As it turns out, we manifest our leadership abilities through the same struggles as private-sector CEO’s.

    Thank you for the insight and I look forward to reading The Leadership Gap!

    Reply to this comment

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