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Derek Deprey

@derekdeprey

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Last AAU tournament ever with both of my girls playing in the same event. Won’t lie. It hit me. You don’t always realize it’s the last time… until it is. That’s how life works. Seasons change. Grateful for every car ride, game, and moment we shared on this ride together. 😭❤️🏀 taken in Spooky Nook Sports Champion Mill by @derekdeprey

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a year ago

Most people say, “It’s just a game.” But most people don’t see what we’ve seen.

They don’t see the 7-hour car rides that somehow fly by because we’re talking hoops and life… father to daughter, coach to player, heart to heart.

They don’t see us finding a gym in every city, just to get shots up before the next game… because routine matters, and passion doesn’t rest.

They don’t see the non-negotiable postgame ice cream stops… our little tradition, win or lose.

They don’t see the constant communication with college coaches… navigating hopes, dreams, and unknowns with a lump in your throat, hoping you’ve done enough.

They don’t see the hours, the tears, the effort, the joy.

They don’t see the bond this game built between us.

They don’t see a dad coaching his daughter for the very last time.

This game, this journey, has given us more than I ever imagined.

It gave us time. It gave us something to chase together. It gave us moments I’ll replay in my mind forever.

And to end it with 6 straight wins and a Select 40 championship? That was the dream finish to a story I’ll never stop telling.

What a ride. What a team. What a daughter. What a gift. 🏆❤️

@wisconsin_lakers @elliedeprey @selecteventsbasketball taken in Spooky Nook Sports Champion Mill by @derekdeprey

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a year ago

👉 When was the last time you allowed yourself to be a beginner? What did you learn from that experience?

True leadership isn't about having all the answers—it’s about having the courage to start, make mistakes, and grow. It’s about stepping into the unknown and embracing the learning process.

Every great leader started somewhere. Today is your chance to begin, too. Will you take that first step?

🚀 10 DAYS UNTIL BOOK LAUNCH 🚀 by @derekdeprey

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2 years ago

When you get to Louisville early for your last AAU tournament of the year and only have one game on the schedule, you figure you’ll find a gym and get some shots up.

Well... that didn’t work out. The expo wasn’t open to the public yet. The health clubs were too far away. The community center was closed for gym resurfacing.

So we pivoted. Instead of a shooting workout, Mia and I ended up with an impromptu “daddy-daughter day.”

We walked around Churchill Downs 🐎, checked out the Louisville football stadium, and, according to Mia, saved the best for last... her first-ever trip to Swig. Apparently Wisconsin isn’t cool enough to have those yet.

It’s funny how often life works this way. You make a plan, it falls apart, and sometimes you end up with something even better.

In a few short years, these AAU tournaments will be over. The games, the hotels, the road trips, and the countless hours in the car will become memories. I’m grateful this one came with a reminder that sometimes the best moments aren’t on the schedule.

Now it’s time for one last tournament of the summer. Let’s make it a good one! ⛹️‍♀️🏀💪 taken in Churchill Downs by @derekdeprey

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a day ago

The Problem Isn’t Always the Employee

One of the most honest leadership conversations I’ve had lately centered around a struggling manager.

At first, the conversation sounded familiar: “They’re disorganized.” “They’re frustrating the team.” “They’re not leading well.” “They keep dropping the ball.”

Then I paused and asked a better question: “Who is actually developing them?”

Silence...

That’s the part organizations skip all the time. We blame the manager while ignoring the leadership system surrounding them.

No onboarding. No coaching rhythm. No leadership training. No consistent feedback. No modeling. No clear expectations.

Then six months later everyone acts shocked that the person is struggling.

Gallup has shared for years that managers account for roughly 70% of the variance in team engagement. That’s massive!

Weak leadership systems don’t just create frustrated employees. They create frustrated managers too.

Another leader I work with said, “We keep promoting people and hoping leadership magically appears.”

Exactly! Being good at the work and being good at leading people are two completely different skill sets.

One of the biggest mindset shifts leaders can make is moving from “What’s wrong with this person?” to “What support, clarity, accountability, or coaching is missing here?”

That question changes the conversation fast. Sometimes the employee isn’t the main issue at all.

What leadership gap is your organization still treating like a people problem? by @derekdeprey

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a day ago

Leadership Development Is a Team Sport

The best leadership development experiences don't start when the facilitator walks into the room. And they certainly don't end when the workshop is over.

Over the past several months, I had the opportunity to partner with @wctcedu - Waukesha County Technical College on a leadership development experience focused on performance management.

What made this experience successful wasn't just the workshop content or the group coaching sessions. It was the partnership.

Long before we ever gathered in the room, Katie DeRemer and her team shared organizational priorities, provided cultural context, and helped ensure the experience connected to the realities their leaders face every day. As a result, we weren't talking about hypothetical leadership challenges. We were talking about real ones.

How do we make feedback less intimidating? How do we create accountability without creating fear? How do we make performance conversations something people actually look forward to?

Then came my favorite part... watching leaders continue the conversation during group coaching. That's where the learning moved from concepts to commitments. Leaders shared wins, discussed challenges, and held themselves accountable to putting the work into practice.

One reminder from this experience. Great leadership development isn't something you deliver. It's something you build TOGETHER.

Thank you to Katie and the entire WCTC leadership team for your preparation, engagement, and commitment to developing your leaders. It was an honor to be part of your leadership journey.

Now I'd love to hear from you. What's one thing you've found helps learning continue long after a workshop or conference ends? taken in WCTC - Waukesha County Technical College by @derekdeprey

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2 days ago

The Promotion Gap Nobody Talks About

A leader I met was frustrated. Not because things were going badly. Actually, things were going really well!

More responsibility. Bigger projects. Greater influence. Increased visibility. On paper, everything looked like growth. 🚀🚀🚀

He said, “I think my team misses the version of me that had more time.” That’s a weird realization as a leader because most of us assume growth automatically feels exciting.
But growth often creates tension too. The better you perform, the more you’re trusted. The more you’re trusted, the more you carry. And if you’re not intentional, your team can quietly interpret that shift as: "He’s not as available anymore." "She'’s checked out." "He doesn’t care as much."

Not because your heart changed. Because your capacity changed.

Leadership isn't just about growing your responsibilities. It’s helping people understand the transition while still making them feel seen along the way.

Sometimes leaders don’t need to work harder. They need to communicate the shift better.

What changes in your leadership when your role gets bigger? by @derekdeprey

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4 days ago

The people you lead aren't just completing tasks. They're growing, learning, and becoming.

Take time to coach, encourage, and challenge them. The impact of great leadership isn't measured only by what gets accomplished today, but by who people become because they worked with you. by @derekdeprey

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5 days ago

The “Good Job” Trap

One thing I noticed during a leadership workshop with managers in the building industry…
Almost everybody agreed that feedback matters. But once we started talking about what feedback actually sounds like day to day, the room got quiet for a second.

Because a lot of leaders realized they default to: “Good job.” “Nice work.” “Appreciate it.”
Nothing wrong with those phrases. But one participant said something that immediately changed the conversation: “Good job at what?”

Generic praise feels good for about three seconds. Specific feedback actually teaches people what success looks like.

One manager talked about simply complimenting one person every day, even if it’s quick while walking by. Another shared how handwritten notes can stick with employees for years. We even joked about complimenting a coworker’s hairline.

But underneath the humor was a real leadership pattern. The best leaders don’t just encourage people. They help people understand *exactly* why their contribution mattered.
Specificity builds confidence. Specificity builds culture. Specificity helps people repeat winning behaviors.

Your employees shouldn’t have to guess what “good” looks like.

What’s one piece of specific positive feedback you could give somebody today? by @derekdeprey

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8 days ago

The Leadership Blind Spot Nobody Loves Talking About

A leadership pattern surfaced during a training session that almost every manager in the room quietly related to. Most leaders say they want feedback... until the feedback actually arrives.

One participant admitted, “Sometimes I take it too personally and stop listening to the whole statement.” Another leader talked about wanting more negative feedback instead of only hearing the positive. Someone else joked that if they sent an anonymous survey, they’d immediately want to know who wrote the criticism. The whole room laughed because, honestly, we’ve all been there.

But that was the deeper lesson. A lot of leaders want growth without discomfort. And the irony is that the people asking employees to be coachable sometimes struggle to be coached themselves.

One of the best comments from the discussion was, “You really want to understand why they’re saying what they’re saying.”

That’s leadership maturity. Not reacting immediately. Not defending yourself immediately. Not shutting down. Just staying curious long enough to learn something.

The strongest leaders I know are not the ones who avoid criticism. They’re the ones willing to hear it fully before deciding what to do with it. by @derekdeprey

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11 days ago

People grow faster when they feel seen.

Take time to recognize strengths, celebrate progress, and remind people of the value they bring.

Sometimes the greatest gift a leader can give is helping someone see in themselves what they couldn't see on their own. by @derekdeprey

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12 days ago

The Fastest Way to Lose a Room

A participant in a workshop I led shared a moment. She talked about sitting in meetings with programmers and technical experts where everyone else seemed fluent in a language she didn’t understand.

So what did she do? She nodded, pretended to follow along, and waited for it to end.
Honestly, most of us have probably been there at some point. The dangerous part is that many leaders mistake silence for understanding.

But confusion rarely raises its hand. Disengagement doesn’t usually announce itself. People often smile politely while mentally checking out 20 minutes earlier.

One of the fastest ways to lose connection with people is speaking over them instead of speaking with them. I mean, it happens everywhere. Leaders using company jargon nobody understands. Presenters trying too hard to sound impressive. Experts forgetting what it feels like to be new. And meetings packed with acronyms and complexity.

Clear communication is not “dumbing things down.” It’s respecting the room.
The best communicators don’t make people feel small. They make people feel included.

Think about it. If people constantly need a translator to understand you, the connection is probably already gone.

What’s the worst example of “corporate language” or confusing jargon you’ve ever heard in a meeting? by @derekdeprey

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15 days ago