Futures, Fruit Trees, and the Hardest Question a Leader Can Ask
I’ve just returned from my second residency in the Doctor of Executive Leadership program at the University of Charleston, and like the first one, it cracked something open in me. Residency isn’t just a week of classes; it’s a full-immersion leadership reset. It pulls you out of your daily life, drops you into a room with brilliant humans from across industries, and pushes you to think bigger, deeper, and more honestly about who you are as a leader and who you’re becoming.
This time, three big takeaways landed with force…
Actually, make that four.
Many futures are possible—and I’m already shaping them.
One of the most powerful ideas this week came from recognizing how many possible futures exist at any moment. There isn’t just one inevitable future waiting for us. There are dozens. Maybe hundreds. Futures we intentionally create… and futures we drift into without realizing it.
The uncomfortable truth I had to swallow:
I’m already shaping futures, even the ones I didn’t consciously choose, agree with, or fully understand.
We all are.
Every decision, every habit, every conversation, every assumption we leave unchallenged—it all nudges the future in one direction or another. Leadership isn’t just about making choices; it’s about recognizing the quiet ways we’re influencing outcomes all the time.
Residency forced me to confront my own patterns:
Where am I choosing deliberately?
Where am I choosing by momentum?
Where am I avoiding choices altogether—and still shaping the future anyway?
This idea alone was worth the trip. It reminded me that leadership is inherently moral work. Whether we like it or not, we’re building pathways for others to walk. And if we don’t take responsibility for that, someone else eventually will.
Don’t plant crops. Plant trees. (Thank you, Elton.)
A metaphor from my classmate Elton hit me like a lightning bolt.
Some leaders plant crops - quick wins, immediate results, the kind of work that feeds an organization for a season.
Other leaders plant trees - the kind of long-term development that grows leaders who go on to grow more leaders. Fruit trees that keep producing long after you’re gone.
Crops = performance management, checklists, tactical wins
Trees = people development, mentorship, leadership pipelines, capability-building
Both matter. But only one leaves a legacy.
It made me ask myself, bluntly:
Am I planting crops? Or am I planting trees?
In my work across restaurant, retail, franchise, and hospitality brands, this metaphor reframed something I’ve believed for years: the best leaders don’t produce more followers, they produce more leaders.
Thank you, Elton, for giving language to what so many of us intuitively feel but couldn’t articulate.
Crops feed people for a season.
Trees feed people for generations.
Master the ability to think about what you’re thinking about.
Metacognition, the ability to think about what you’re thinking about, is a leadership superpower.
Residency forced that internal work in a way I wasn’t expecting. Long days of deep conversation and honest reflection made me confront the reality that leadership often comes down to noticing:
Why did that comment trigger me?
Why did that idea energize me?
Why did I avoid that topic?
What assumptions am I carrying without examining them?
If you can observe your thinking, you can change it.
If you can change your thinking, you can change your behaviour.
If you can change your behavior, you can change your future.
Every leadership skill rests on the foundation of being able to step outside yourself and actually see how you’re thinking.
“What does it feel like on the other side of me?” (Thank you, Antwan.)
This one… hit with fire. Truly.
One of our third-year students, Antwan, asked a question that hit with the force of truth:
“What does it feel like on the other side of you?”
Not:
What do you intend people to experience?
What do you hope they experience?
What do you tell yourself they experience?
But what do people actually feel when they interact with you?
Do they feel heard?
Safe?
Inspired?
Rushed?
Dismissed?
Pressured?
Expanded?
Interrupted?
Empowered?
This is the leadership question that slices through every illusion.
It ties directly to the other three takeaways—because you cannot plant trees, shape futures, or examine your thinking unless you’re willing to understand the emotional wake you leave behind.
This question is staying with me.
It’s confronting. It’s clarifying. It’s necessary.
Thank you, Antwon, for this one. It’s already changing me.
The power of being together: Year One meets Year Three
Another gift of residency was the people.
Connecting with the new Year One cohort reminded me of the wonder, energy, and optimism that mark the start of this journey.
Spending time with those entering Year Three—deep in dissertation work—showed me exactly what this program is shaping me toward.
It’s rare in life to be surrounded by people who are all pushing themselves mentally, emotionally, morally. That environment changes you. It elevates you.
And this time, something deeply personal and unexpected happened.
Being selected as the George Walker Fellow (WOW!)
I am still absorbing this.
Being named the George Walker Fellow is one of the greatest honors of my academic and professional life. This fellowship recognizes students who embody leadership excellence, character, contribution, and the potential to lead at the highest levels.
To be selected from among such extraordinary leaders is both humbling and energizing. It feels like a profound affirmation of the work I’ve dedicated my life to.
It’s an honor I will carry with deep gratitude.
Receiving my first challenge coin
As if the fellowship wasn’t enough, something else happened that I will never forget.
A decorated member of the military, someone I deeply respect, gave me a challenge coin and told me he respected my leadership.
For those who haven’t lived in military or policing circles, a challenge coin isn’t a trinket. It’s a symbol of respect, values, service, and earned trust. It’s given deliberately. Sparingly. Meaningfully.
Receiving one is rare.
Receiving one in this context… left me speechless.
It is one of the great honors of my career.
Learning alongside active-duty military and veterans
One of the things I value most about the University of Charleston is that it’s one of the most chosen institutions in the U.S. by active-duty military and veterans.
To learn beside people who have lived leadership in environments where stakes are literally life or death—people who understand service, responsibility, and discipline at the highest level—elevates every conversation.
It is a privilege to learn with them and from them.
Closing reflection
Residency 2 didn’t just teach me something.
It changed something in me.
It sharpened how I see the future I’m shaping.
It reminded me to plant trees, not just crops.
It deepened my ability to observe my own thinking.
And it left me with the hardest, truest leadership question of all:
“What does it feel like on the other side of me?”
If I can live into that question with honesty and courage… the rest will take care of itself.