Seasons of Leadership

Jun 17, 2024

My church just turned 40. I was around in the early days—back when we were meeting in a smelly, noisy, junior high cafeteria. This was long before we had a building, paid staff, and parking problems. Recently, the church asked me to come talk to the 300-plus members of staff. 

It felt a bit like one of the famed “Talks at Google.” The group was young, hungry, and full of energy. Our directional pastor wanted to help them grow as both shepherd leaders AND enterprise leaders (concepts I have written about). 

It was a fun experience for me because I got to use my skills as an executive coach and my perspective as a long-term member of the church to speak to a group I really cared about on a topic I’m increasingly passionate about: seasons of leadership.

I’ve been passionate about that topic for decades. Leaders who are worth their salt know that they have to keep growing. New teammates come aboard, new competitors enter the market, new resources become available, new conversations dominate the culture, and new challenges arise. You are changing, and your situation is changing.

Both individual leaders and organizations can’t stop growing. Old leaders often over-trust their past successes, while new leaders over-trust their intuition. Old organizations lean on their reputation, while new organizations can over-lean on their culture. New or old, leader or organization, we must continue the growth through every season of leadership.

That’s the point I wanted to get across to these young leaders. Here were the big ideas I shared that day:

1. Organizations go through seasons and cycles like humans.

It’s been four decades since I read my first book on organizational life cycles, Barbarians to Bureaucrats by Lawrence Miller. It was an eye-opener for me. Miller tracked the idea of an organization going through the process of birth > infancy > toddlerhood > adolescence > young adulthood > maturing adulthood > aging decline. It’s a bell curve, and as you can see, it maps to human life. Although many new books have been written on the topic, they generally all conceptually agree on four main stages in the life of any organization:

  • Introduction (birth)
  • Growth (adolescence)
  • Maturity (adulthood)
  • Decline (aging)

Now, here is the big aha. Humans can’t hack the bell curve, but organizations can. In other words, we humans are born, grow, mature, and die. How we as humans embrace aging gracefully is a whole other conversation. But organizations can jump the S-curve, beat death, and actually become multigenerational. They can “reinvent” themselves time after time. We have seen this happen repeatedly with not-for-profits, churches, small family businesses, and multinational giants.

Good leadership recognizes the organizational season you’re in and asks questions like, “How do we hold onto some of the past but also let go of things that we need to let go of?”

2. Different seasons invite require a different kind of leadership from us.

I’m in my 6.0 season. Some call it the fourth quarter. Some call it landing the plane. But as for me, I’m focused on words like leverage, harvest, transfer, and galvanize. Those are very different words than the words that steered my 2.0 or 4.0 season. I’m not shutting it down, but I am attempting to age with grace and confidence

My friend Fred Smith releases a weekly article that I enjoy. Hear his thoughts on this very idea. 

“Too often, we can get stuck in being the person we have always been and fail to adjust to the next season. We cling to control too long when the organization needs a delegator. We delegate too much when a season of transition necessitates us stepping back into the day to day to reinforce culture. We fail to give seasoned employees the trust and responsibility they’ve earned or don’t alter our leadership style to handle the new high performers on the team.”

Are you adapting and advancing your leadership maturity, or are you just getting older? Are you leading differently than you were five years ago? Then, look to the present. What season of life and work are you in? What are the unique opportunities that it affords? What will change over the next 10 months and 10 years? What won’t you be able to do in the next season that you can do now?

Psalm 78:70-72 has steered my life and work since I was in my twenties: “[God] chose David his servant and took him from the sheep pens; he brought him from tending ewes to be shepherd over his people Jacob—over Israel, his inheritance. He shepherded them with a pure heart and guided them with skillful hands.”

David’s leadership journey was remarkable. He went from being a shepherd of animals to a shepherd of people to an enterprise leader of an entire kingdom. Just think about what it takes to be an effective leader in each of those different assignments. And I am certain he grew and adapted as he transitioned to new leadership stations.

3. My primary assignment in each season is to be faithful and fruitful. 

As we weave our way through the Bible cover to cover, we see a consistent and implied theme connected to leadership. The primary assignment of leadership, no matter the season of life and work, is to be faithful and fruitful. Not successful or efficient or accomplished. Faithful and fruitful. That’s the big idea.


I’m convinced that great leaders—and this is true whether they identify as followers of Jesus like I do or not—are motivated by stewardship, by the sense that what they have is something to be used for the good of others and not themselves. As Woodrow Wilson said, “You are not here merely to make a living. … You are here to enrich the world.”

Faithfulness means I have tapped into my God-given superpowers and am using them to direct the way I do my life and work. Faithfulness means I am constantly creating both a greenhouse and a launching pad for the people in my leadership orbit. Faithfulness means I am performing every day regardless of my title and address (that is, where my work takes place) for the primary audience of One (God).


Leaders cannot totally engineer success or fruit. We like to think we can, and the multibillion-dollar self-help industry is designed to sell that notion. But, we're not totally in control. Remember that verse in 1 Corinthians 3:5-10: “I planted, Apollos watered, but God gives the growth.” That said, we should have a bit of discontent if there is no impact from our labor, no positive change, no fruit. 

John 15:5 gives us a graphic image of the fruit-bearing process: “I am the vine; you are the branches. The one who abides in me and I in him produces much fruit, because you can do nothing without me.”

Francis Chan said it this way: “There are periods that we forget that in the pursuit of fruit, that if we just abide in Him, then fruitfulness is a guarantee.


I don’t know what season of life and work you find yourself in—perhaps you’re just getting started and finding your footing as a leader. Or perhaps you’re in hypergrowth. Life is full, busy, heavy and just one constant roundabout. Some of you might be in the maturity season. Things are full, but you have them under control (or at least you think so). And then some of you are at the sunset of a leadership career.

In each season, my words to you are “faithful” and “fruitful.” Are you viewing your role as a caretaker of what you’ve been given, and are you desiring and strategizing and working for fruit? And, in all of it, are you recognizing the unique season you’re in and the unique leadership that requires? Press on.

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