Great Leaders are Always Learning

Learning Sign in Silver Letters on Concrete WallGrowth of your organization is tightly tied to your growth as a leader especially if you’re an entrepreneur. Overcoming the challenges to your personal growth will, in turn, help you kick-start your company’s growth.

Today’s post is by Michael Dermer, author of The Lonely Entrepreneur (CLICK HERE to get your copy).

There’s a powerful book called Leading at the Speed of Growth: Journey from Entrepreneur to CEO by Katherine Catlin and Jana Matthews. It addresses the long-standing belief that entrepreneurs who start a business do not possess the skills to help a business grow. It challenges this notion and argues that entrepreneurs have enormous talent that simply needs to be applied differently at various stages of the business. In other words, the unique talents entrepreneurs possess—drive, passion, creativity, the stomach for risk and uncertainty—can’t remain static or be applied with cookie cutter repetition to distinct and evolving stages of your business.

No matter how much talent you bring to the table, to achieve success you can’t remain satisfied with your own status quo. Your skills and perspective must be adaptable and flexible as you grow your business. This had a profound impact on me. It was as though someone said to me, “If you are as good as you think you are, you need to change.” Initially, this really challenged me—though I’m sure it was my ego talking.

Then I realized how much a change in my own perspective could help my company. What an opportunity. I also didn’t realize was how empowering it was to be challenged, to acknowledge shortcomings and to grow.

Change in the midst of calm seas is one thing. Change in the middle of a hurricane is another. If you can come out the other side, imagine what that would feel like. When someone asks you, “How is your company going?” you probably answer with a description that includes the word crazy or chaotic or nutty or something unprintable. Wouldn’t it be something to be able to say “We have everything under control?” When my company was acquired, one of the sales team members of the company that acquired us said to me “Every time I interact with your business or your people, you are organized, structured and efficient.” What a message to be able to share with your team. It still makes me proud.

Humility is a trait of strong leaders—the type of leaders employees want to work for and investors want to fund. In my book – The Lonely Entrepreneur – I wrote that one of the most important days in the history of my company was when I realized being a CEO was a skill that needed to be developed with the same perseverance, ferocity and willingness to learn that athletes apply to their training. It was no different than ballet or working on your golf game. This is one of those skills that must be genuinely developed.

Take the example of how to get team members aligned to a plan or objective. Let’s say your team is skeptical of your perspective on how to release the beta of your product. There are two ways you can handle the same issue. One approach would be to tell them what to do. Another approach would be to introduce the topic and say something like “I was wrong about how to approach our alpha version and wanted to make sure we got it right this time. My initial gut is that we should launch in the summer, but what do you think?” Express to team members that you would like everyone’s feedback on the approach.

There are many funny (and not so funny) crazy entrepreneurial stories I lived through. Being humble and acknowledging the error of your ways is also a great way to build trust and credibility helped. I’ve had first-hand experience with this dynamic. We’d been selected as a finalist for an RFP for a large health plan to be their incentive vendor and I was leading the presentation. During a break, one of their employees directed me to the restroom and said “Do you know how to get back? It’s hard to make your way around here because all the halls look the same.” I said I was fine. After about a half hour of walking around while my team was presenting, I walked in the door. Everyone smiled with that sheepish look of “we told you so.” They asked if I was okay and I said, “If the CEO of your vendor can’t find his way back from the bathroom, I don’t think you should hire us to run your incentive programs.” Everyone laughed and we moved on. We wound up winning the RFP. I’m sure that was not the reason why, but I think they knew they were partnering with someone who was real.

When you demonstrate humility and embrace learning, you can unlock great things in your team. However, humility has to be balanced. First, it has to be balanced with a sense of confidence. If this humility is not balanced with strength, you can undermine the team’s belief in you and in the business. The key is finding the right mix.

Second, humility has to be genuine and never used to manipulate. When team members see their leaders genuinely willing to acknowledge mistakes or deficits in a particular area, it inspires them to discover their own confidence to act, take risks, and evaluate their own deficits. This leads to genuine improvement and self-development that will have many positive impacts for your company. But don’t forget, it starts with you.

There is a famous line in the John Lennon song “Borrowed Time”—“The more I see the less I know.” Once you accept this, it is easier to see that your perspective is both the cause of your company’s problems, and its best opportunity for success! Embrace the gift of growth and learning. You may tap potential you didn’t know you had.

The Lonely Entrepreneur– Michael Dermer is the founder/author of The Lonely Entrepreneur (CLICK HERE to get your copy), a methodology to help entrepreneurs with the struggle. He discovered this methodology when the company he built for a decade – the first to provide rewards for healthy behavior – was nearly destroyed by the 2008 financial crisis. He not only overcame this to become an industry pioneer, but discovered this methodology to help entrepreneurs with the struggle and is now a professional speaker, consultant, and coach for startup businesses and entrepreneurs. Learn more at

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Photo: Classic Learning by Alan Levine

2 Responses to “Great Leaders are Always Learning”

  1. I can relate with this book a lot as I am have been mostly a serial entrepreneur with more failures. Lately my recent venture is going well. I will definitely would like to read the insight of Mike in the book. Such works keeps coming from various people so that new leaders can arise in different sectors. Thank you.

  2. Las says:

    It is an absolutely true article. Everyone of Us of the world has to learn not only the leaders. But as a good saying is: “Leaders are Readers”. I loved it

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