THE LEADERSHIP BLOG
Reflections on Leadership, Clarity, and Growth
Derek’s blog is where he shares reflections on leadership as it is lived: practical insights, real moments, and ideas leaders can return to when they need perspective. Many ideas shared here connect directly to Derek’s books, speaking topics, workshops, and the Lead on 3 framework. Readers often use these reflections as a place to pause, reset, and refocus.
What 1,800 Cups of Coffee Taught Me about Connection
I've probably purchased around 1,800 cups of coffee from the same place over roughly eight years. My order isn't complicated. Black coffee. One day, a barista looked at the name that appeared with my order and simply said, “Thanks, Derek.” It was a tiny moment, but I noticed it.
Be More Interruptible
I've had moments when Ellie or Mia interrupted me while I was working and, even if I didn't say anything, my body language probably communicated exactly what I was thinking: Can't you see I'm busy? Most leaders know that feeling. You're focused, moving fast, and finally getting something done when someone appears.
The Star of the Team Is the Team
During my time as Coordinator of Basketball Operations at Marquette University, there was a banner associated with our program that carried a simple message:
THE STAR OF THE TEAM IS THE TEAM.
Tom Crean used the phrase, and I've never forgotten it.
Stop Chasing Work-Life Balance
For years, I chased work-life balance. I also spent a lot of time frustrated that I couldn't seem to find it.
The picture made sense in my head: work on one side, life on the other, and somehow keep both sides of the scale perfectly level.
Then I tried to actually live that way.
Eventually, I realized I was working with the wrong picture.
Clarity Isn't About Saying More
During a Speak with Impact experience with Hawkes Learning, a participant shared a communication challenge that captured something I see leaders do all the time. The message had technically been communicated, but an important piece of context was missing. The words themselves weren't necessarily wrong; the listener simply didn't have enough information to understand what those words actually meant. That's a clarity problem.
You Can't Train From a Distance
Imagine a basketball coach trying to develop players without ever watching them play. No practices. No games. No film. No conversations about what happened. Just occasional instructions from a distance followed by an expectation that everyone should improve. It would be ridiculous in sports, yet leaders sometimes try to develop employees in a surprisingly similar way.
When Helping Becomes the Problem
A leader once described a problem to me that I hear in different forms all the time. “I keep being asked to help. And the problem is...I always do.” At first, that doesn't sound like much of a leadership problem. Helping people is good. Being responsive is good. Supporting your team is part of the job. The problem is when helping quietly becomes rescuing.
When Everything Is a Priority, Nothing Is
I've asked leaders to look at a list containing 20 goals, projects, responsibilities, and commitments. Usually, the challenge isn't that any one item is unimportant. The problem is that all 20 supposedly are.
Where Change Actually Breaks
One of the easiest mistakes leaders make during organizational change is forgetting how long they've already been living with the change. Senior leaders may have spent six months discussing it. They've reviewed options, debated risks, asked questions, changed their minds, looked at drafts, worked through concerns, and gradually arrived at a decision they're ready to implement.
Performance Management Shouldn't Feel Like Judgment Day
For a lot of employees, the annual performance review feels less like development and more like judgment day. They walk into a room knowing they're about to hear an official assessment of work they've been doing for the last 12 months, sometimes wondering whether they're about to learn something their leader has been thinking for months.
The Scholarship Wasn't Earned Today
We tend to notice the promotion, the successful presentation, the big client win, or the team that suddenly seems to be performing at another level. We see the leader confidently navigating a difficult conversation and assume confidence simply showed up. What we don't see are all the repetitions that came first.
One Team, One Canoe
Different departments naturally experience the organization from different seats. Sales has goals and pressures. Operations has its own. Clinical Care sees things through another lens. Each group has responsibilities, expertise, and priorities that legitimately matter. Problems begin when people become so focused on their seat that they forget they're sitting in the same canoe.
The “Good Job” Trap
During a leadership workshop with a group from the building industry, we were talking about feedback when a participant offered three words that captured one of its biggest problems:
“Good job at what?”
The Leadership Blind Spot
I was facilitating a leadership workshop when our conversation turned to feedback. One participant said something remarkably honest: “I take it personally.”
What the Boxcars Can Still Teach
In 1933, Joseph Siwek lost his railroad job. It was the middle of the Great Depression, and families in Minnesota needed firewood to heat their homes. Joseph started dismantling old wooden boxcars, pulling nails, and selling the scrap wood as firewood.