John, Anne, and Sean have worked together for over five years in the same building. They have the same job but manage different teams. They often go out to lunch and talk about their children, partners, and major life events. But there is one thing they never talk about: their leadership struggles. 

Why Don’t Leaders Feel Comfortable Sharing Work Challenges?

I’ve discovered, in my many years of working in Lean HR, that some of the following reasons often get in the way of these important conversations:

  • Leaders think they are the only ones struggling to lead their teams
  • They believe they should be better at leading than they are
  • Sharing struggles requires vulnerability 

Most leadership teams I’ve encountered don’t realize that others are experiencing the same challenges … until something happens that causes them to share. The problem is rooted in the fact that most workplaces don’t value sharing and don’t encourage vulnerability.

Vulnerability Does Not Mean Inadequacy 

Work culture fosters the unspoken expectation that leaders should be able to lead their teams with minimal, if any, support. If they’ve made it this far, they should be able to do it on their own, right?


To lead a team well is anything but easy. Successfully leading a team requires a wide range of abilities, including: 

  • Creating a vision of success
  • Motivating the team to reach goals and targets
  • Ensuring expectations are clear and understood
  • Providing effective training
  • Consistent coaching and mentoring
  • Prioritizing positive and constructive feedback 

Leading teams and working with people requires a lot of different skills, especially when it comes to a coaching style of leadership. As I discussed in my last blog, coaching isn’t just hard; it’s really hard.

People almost always underestimate the difficulty of coaching versus problem solving. Many leaders believe they were put into their role due to their problem-solving abilities. The team who depends on their leader to solve problems is an underdeveloped one. This approach creates a dependent workforce and an overwhelmed leader. 

Leadership Support Optimizes Potential 

Many organizations want to move to a coaching style of leadership, but struggle to support their leaders. The idea is not complex, but the implementation certainly is. Providing space and time for leaders to share their struggles is essential in developing leaders who coach. 

No matter the struggle (addiction, weight loss, leadership), when people can come together to share challenges and gain support, they do better. There is something comforting about realizing that you aren’t the only one who struggles with a certain problem. 

When a company believes in optimizing the talent of their people, they’ll need to start with a robust support system as a foundation. While the workplace is not a support group, organizations that can find a way to support leaders in sharing their challenges during and through the transition to coaching will be more successful in developing a competent team.  

If you would like to learn more about how your organization can foster a supportive, coaching environment for your leaders, contact me here.

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