All good things do come to an end . . . including all executive leadership roles. This post takes readers behind the curtain to understand the complexities and dynamics and benefits of engineering a great ending. Michael Le Roy Associates and MyNextSeason work in partnership to plan and support boards and presidents who want to finish well.

Executive advising is the “art of accompaniment” provided by someone who listens well, asks probing questions, and draws on a significant experience in a complex leadership role. Leadership is profoundly challenging work, but it can also be rewarding work if you decide you aren’t going to do it alone. The post below describes my work with three leaders to understand the practical aspects and benefits of having an executive advisor accompany you on your leadership journey.

Mature leaders seek out advisors when they step into a leadership role, and boards should view a leader’s desire to have one or more trusted advisors as an indicator of humility and strength. Many of the most experienced and accomplished leaders I know have one or two advisors they continue to retain across multiple roles in different organizations. Overly insecure or arrogant leaders simply don’t seek out an advisor.

As I moved into leadership roles and started working with people making big decisions about “retirement,” I realized I was making some significant, erroneous assumptions about the meaning of this concept. As an early and mid-career professional, I understood retirement as “the act of leaving one’s job and ceasing participation in the workforce.” Without examining my assumptions, I imagined retirees as people with almost unlimited discretionary time, low golf handicaps, and time to work through a great reading list in sunny places while the rest of us worked through the winter. But just as the red maple leaf is not nature’s only harbinger of Fall, retreat from the workforce describes only one aspect among many possibilities.

With the long, intense days of work that begin early and end late, travel across time zones over a short number of days, evening events and activities, nonstop mobile communication, and all the burdens and worries associated with leading a large organization it surprises me that any leader can sleep at all. I certainly struggled with this as well. Sleep deprivation erodes the executive function of the brain, and it also erodes an executive’s ability to function.

In 2018, six years into a college presidency and thirteen years into my work as a senior leader in higher education, I took a long walk. I walked out my front door and then seven miles to the airport in Grand Rapids with my backpack on, my phone turned off, and the hope that I could walk 542 miles from the French-Spanish border to the Atlantic Ocean.