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Lenny Comma

Lenny Comma’s Leadership Lessons | ExCo Insights

April 29, 2024

This series explores some of our executive coaches’ and mentors’ most important lessons and insights. The ExCo Group executive coach and mentor, Lenny Comma, Director at Burger BossCo. Holdings Inc. and former Chairman & CEO at Jack in the Box Inc., shares his lessons, including the significance of leadership as an act of service, the value of strong relationships, and more leadership insights.

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The greatest lesson I learned early in my career is that leadership should be an act of service. There’s a lot behind that statement. Often, people desire a leadership role because it comes with prestige, a title, or something that will stroke their ego. But you find that those positions can be extremely exhausting unless you have the right motivation.

You should have a fundamental desire to care for people. If you do not feel that way, people will exhaust you, their issues will exhaust you, their emotions will exhaust you.

You should have a fundamental desire to care for people. If you do not feel that way, people will exhaust you, their issues will exhaust you, their emotions will exhaust you. You’ll see it as a chore. But if you fundamentally care about people and how they’re doing, you’ll want to create an environment where they can do their best work and bring their authentic selves to work. Then, you will find the job challenging but extremely fulfilling.

Of course, leadership is also results. There will be times when driving results may seem to be in conflict with what an individual desires. So you must be a pragmatist and step back and say,  what’s the greater good here? How do I make an elegant decision that serves the organization in the best way? You must have conviction, a path, and a vision for the organization, but how you get there is somewhat malleable. That requires humility to acknowledge that you may have made a mistake or that things aren’t working out quite how you intended and that you need to change direction. People respect that. Leaders aren’t expected to be all-knowing.

A second key leadership lesson is to lean on your strengths and only try to mitigate your weaknesses. Early in my career, there was a heavy emphasis on 360-degree appraisals and understanding your strengths and weaknesses through all these assessments. I found that people would take the results and then hyper-focus on their weaknesses. If you could fix all these things about yourself and develop all these new skills, you would be a better professional and a better leader.

That actually proves to be largely untrue. I’m not saying that it’s okay to cop out on those things that need fine-tuning. You can’t let something that’s fundamentally required in the job get in the way of performing well. I am saying that leaders have certain fundamental strengths that come naturally to them and that they should lean heavily on those to get the job done. They should also be very transparent and humble about their weaknesses, and they should only try to mitigate them by putting processes and people in place to help them. Then, you can focus your energy on building your strengths and how to use those strengths to drive your success and the organization’s success.



One common theme is around relationships. It’s amazing to see how many leaders have reached high-level positions without yet learning the value of strong relationships with their colleagues. Instead, they’re very transactional, and that’s the feedback others give them—that they see people as a means to an end. They don’t really want their feedback. They don’t really want others to be part of their thought process. As a result, people don’t feel valued or respected; their defenses go up, so they aren’t inclined to help them.

So, I advise them to invest more time in getting others’ input early in the process. What do you think about this idea? If you were to do it, how might you approach it? Do you think I’m headed in the right direction? Too often, they don’t do any of that. Instead, they have a plan and want people to follow it. When they don’t get help, they tend to write off their colleagues as unhelpful rather than reflecting on what they could have done differently.

Another big theme concerns senior executives who are trying to find a fulfilling way to transition into the last chapter of their careers. They usually look at about five to seven years, likely their highest potential for earning money. This is also the period when they’re likely to have the greatest impact and influence as leaders in their organizations.

But this period also often coincides with them no longer feeling fulfilled and purposeful in their careers. It can be challenging for them to find the right motivation and reframe their expectations. So, I advise them to see work through a different lens and to start thinking about legacy. That means taking a step back from their specific job and thinking about when they felt most fulfilled in previous roles or their personal lives. That helps clarify what’s really important to them and what adjustments or changes they can make. And how flexible is their organization in terms of being willing to bend to some of their needs?

At the risk of oversimplifying, there are three possible solutions. One is to change your role in ways that give you more fulfillment. The second is to find some things outside your job that will help fill in some gaps and help you feel more fulfilled. Or if you feel your current situation is untenable, you will have to leave your company and do something else.

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