The journey’s end

Nov 03, 2024

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When the time comes, the best thing you can do for yourself, your legacy, and your organization is to end the journey well.

One day it will all be over. The thought of some finality to your leadership journey could either be very comforting or perhaps a little unsettling. If you are fresh into your leadership journey, you may want to come back to this article in a few years and give it a read. But if you’ve been at this a while and are starting to realize that this thing is really headed somewhere, then we need to discuss the end of the journey.

It was frighteningly easy to start the business that would eventually consume the prime decades of my life. I remember that it cost us almost no money to get a couple of cell phones, print off some business cards, and obtain a tax ID number from the government. Many of you had a similar experience with your own start-up venture. We really didn’t have the bandwidth to think about anything more than the present moment and next week’s payroll. But our business was no more than two years old when we started getting our first offers to sell, followed up with the question, “What is your exit strategy?”

It was initially easy for me to dismiss these kinds of questions, as I had much more pressing concerns and an endless vision for the future of our burgeoning enterprise. However, with growth and maturity came perspective, and I began to realize that there really would be an end to the road ahead. As I ruminated on this idea it became very clear to me that navigating the end of the journey would be a much more difficult task than the start. Of course, there was always the option to close the doors and walk away, but I am talking about ending the journey with dignity and excellence.

How will you know when the end is near? It’s a good question, probably one that most leaders wrestle with often along the journey. A lot of that answer depends on your goals, both professionally and personally. If you circle back to your leadership philosophy, you’ll find some great guidance in getting to the answer. Your reason for getting into leadership and pursuing the journey should line up well with your reasons for it to end. Nevertheless, there are a couple key road signs that a good leader should look out for as their journey progresses:

  • You are no longer able or motivated to grow your leadership. Your leadership, wherever you may be, has a ceiling. One of my leadership bibles is John Maxwell’s 21 Irrefutable Laws of Leadership, a book that was a gift from my wife when I was first promoted to a management position early in my career. John Maxwell devotes an entire chapter in his book to the “Law of the Lid.” I refer to it often and I believe it to be leadership canon. When your leadership ability starts to hit its natural ceiling, your organization will start to show signs of weakness and distress. This is inevitable, because your organization is constantly growing, and with that growth, problems and issues are a natural occurrence. If your leadership is unprepared and unable to navigate these issues, then you have two choices: you can grow your leadership or let the trainwreck pile up behind you.
  • You begin to lose influence in the organization. Leaders have followers and followers are attracted to strong leadership. If you put two potential leaders in front of people, they will naturally opt to follow the stronger and more capable leader. If another stronger and more capable leader emerges in your organization, it may be time to give the organization the gift of your humility and step aside for the greater good. I started my business with a partner who was nearly 13 years older than me. At the time, he possessed more wisdom and life experience than me, so it was a no brainer for him to become president. About seven years later our small two-man operation had grown into a multi-million-dollar enterprise with 50 mouths to feed. I remember distinctly sitting across the table from my partner when he told me that he recognized that my influence and leadership had surpassed his own, and it was time for me to take the reins. It was also time for him to start the slow process of winding down. It was absolutely the right move, but it is only in reflection that I can understand the courage and humility it took to make that simple decision. It was a pivotal moment for both of us, and our organization benefited from the new life of a higher ceiling of leadership.
  • You no longer have the passion to keep going. After years and years, the pressures of leadership will take their toll. Have you ever gone back and looked at the photos of U.S. presidents before and after serving in office? It’s staggering the toll that the highest levels of leadership can levy on a person’s body and soul. You may still have a high ceiling and you may still carry a tremendous amount of influence, but the head cannot function in a place where the heart does not want to dwell. I’ve seen it happen to many leaders in my time. At first, I used to judge these people as perhaps weak or selfish, but as with most lessons in life I now respect those leaders who will listen to their hearts even when there are calls from the organization for them to continue to lead.

Although I can’t capture every sign that points to the journey’s end, I hope you are starting to understand the inevitable nature of this road: one day it will end. Therefore, the best thing you can do for yourself, your legacy, and your organization is to end the journey well.

Take five minutes and consider, “Am I approaching the end of my journey? Do I see a clear and obvious end to this leg of my journey, and am I willing to move on so that the organization can continue to grow and increase its influence in the world?”

Endings are sometimes hard. In fact, until you really start to plan the exit, you have almost no idea what it’s going to take for you to end your journey. Let me encourage you to pay attention to the road signs along the way. If you are wise, you can use these as a guide to set your organization on the right path to success beyond your years and leave a legacy of leadership that will continue long after you are gone. 

Brandon Pinkerton, PE is the founder and CEO of HP Engineering. Contact him at bpinkerton@hpengineeringinc.com.

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