How Can Serving Entrepreneurs Build a Lasting Leadership Legacy?

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How Can Serving Entrepreneurs Build a Lasting Leadership Legacy?

How Can Serving Entrepreneurs Build a Lasting Leadership Legacy?

How does a serving entrepreneur build a lasting leadership legacy? When is the best time to pass your business on to the next generation? How do you help your successor get off to a great start? So many questions, so little time. As I write this, several thousand baby boomer entrepreneurs are deciding to leave their organizations.  It’s their next transition and may be more challenging than their other transitions. For my serving leader clients, it can be even more challenging because they are so intimately connected to their mission, vision, and values. On this Labor Day, I thought I’d share my thoughts on how you can successfully move on to the next stage of your life.  I hope to provide you with several ideas on how to get started.  I spend most of my time working with entrepreneurs on exit and succession strategies, so believe me, I have a few ideas!

There are several key strategies an entrepreneur can use to help them through this next challenge. The first key is making a decision to work on the process with the same energy and focus that you used to build your business. Many leaders I know spend more time planning their vacation then they do developing their exit and succession strategies.  This is because many entrepreneurs fear the unknown until they know they can control it.  To be a successful serving entrepreneur, you’ve learned to reduce your risks.

The second key strategy for serving entrepreneurs is to understand that you want to be in charge of the decision. Another way to put this, you want to make it a matter of choice not chance when you choose to move on. Serving leaders have been successful because they have a finely tuned sense of risk and reward.   They understand how to mitigate risk and leverage potential upside. They are used to making quick decisions and then acting on them.  In this situation, however, a quick decision and then agility may not be your best course of action. Here’s why, you will not be in control of your organization’s future direction.  To have a successful leadership succession, you must be willing to let go and let others control the direction your organization goes in.

The third key strategy for serving entrepreneurs is to understand you must be willing to recreate yourself for the fourth quarter of your life.  That being said, it’s no wonder why serving entrepreneurs have such a challenging time. If you are successful, and most of you are very successful, it’s against human nature to want to change. If something is going wrong, it’s easy to change, correct the course or set a new direction.  At least, it seems that way.  If you’ve been successful, it may because you are incredibly agile and opportunistic in seeing and then seizing potential opportunities. Depending on what you want next, it may require different skills and strategies.

Serving entrepreneurs are very capable of mastering change.  I know what you’re thinking, “I’m not all that flexible. I have a clear vision of what I want and I go after it.” You do, you just don’t always have a great memory!  Just kidding, but the truth is you’ve made many small changes required along the way to be successful. People who succeed are great re-tellers of their history.  We all romanticize the journey.  For many, it’s why we have succeeded beyond our wildest dreams.  We are driven to succeed.

I know several of you are thinking I remember my history; I don’t need to sugarcoat things.  Try this experiment, ask your wife if you’ve ever missed an anniversary or ask your child if you ever missed an important event in their lives. I bet you’ll be surprised by the answer.  I bet more than one time if you are a successful serving entrepreneur. To be a serving entrepreneur requires sacrifice, both from your family and yourself.

If your interesting in learn more about life planning you might also enjoy Does Your Life Need a Business Plan?

Over the next two weeks, I share with you several ways to make this transition easier for you.  Now that we have a foundation in the subject, I discuss a proven framework that helps you continue achieving your goals in your fourth quarter.  See you then.

About the Author

Tripp Braden partners with entrepreneurs and senior executives on their high engagement C-Suite communication and content marketing strategies.

He believes client education is the best way of building trust and long term sustainable growth.

His consulting practice focuses on second stage entrepreneurs, technology organizations, and senior level business executives. Tripp partners with clients to develop high impact C-Suite communication and account based marketing strategies.

If you’re interested in learning more, contact Tripp at or send him an invite on LinkedIn. You can find Tripp’s business growth blog at Market Leadership Journal.

Tripp Braden – who has written posts on Empowering Serving Leaders.

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