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BECOME THE LEADER YOU’D FOLLOW
Derek’s passion in life is to help you become the…
Derek’s passion in life is to help you become the…
Articles by Derek
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Derek Deprey posted thisThe 5-Second Leadership Habit This weekend, Mia and I were on the road for club basketball. Between games, we stopped at a coffee shop to grab a drink. A mom walked in with her two daughters. They ordered, waited, picked up their drinks, and then started heading for the door. But before leaving, the mom stopped and looked at the two baristas behind the counter. She smiled and said, "We're really glad you're here. You're both day-makers." I have no idea what those baristas specifically do for that family every time they walk in. But I do know this... They make a difference. They make an impact. And they help create a moment that matters. Consistently. Think about it. Every day we cross paths with people who are doing important work that often goes unnoticed. Most people notice mistakes. Leaders notice people. Who is someone in your life that deserves a quick note of appreciation? Don’t think about it too long. Send it!
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Derek Deprey shared thisThe Leadership Skill Nobody Schedules: Slow Down to Speed Up A lot of leaders don’t have a delegation problem. They have a speed problem. Most managers don’t struggle with caring. They struggle with making space. Space to think. Space to learn. Space for someone else to wrestle with the problem long enough to grow. Think about it. When a team member asks a question, the leader brain often goes: "I can solve this in five minutes." And you probably can. But what leaders forget is the hidden cost. If you solve it in five minutes, you might buy yourself relief… and sell your team’s development for cheap. The leaders who get the best long-term results do something that feels almost painful in the short-term. They stand next to the person and work through it. They let it take twenty minutes. They embrace the silence. They ask a few questions instead of delivering the answer. That’s support mode, not rescue mode. Support mode builds capability and confidence. Rescue mode builds dependency and learned helplessness. And the easiest way to tell which mode you’re in is simple... Are you teaching in a way that makes you less needed next time? Or are you “helping” in a way that makes you the permanent solution Where do you need to slow down to speed up your team? What’s one situation where you could trade a quick fix for a better coach moment?
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Derek Deprey shared thisThe Human Element Still Wins 🤷♂️ One of my favorite parts of this work is what happens *after* the keynote title slide disappears. You get beyond the polished conference bios and into the real conversations. At the Wisconsin Association of Colleges & Employers (WI-ACE) Spring Conference in Middleton, I had the chance to spend time with professionals from universities, technical colleges, and employers across Wisconsin talking about leadership, students, hiring, AI, burnout, communication, and the future of workforce development. The most encouraging part of the day wasn’t the keynote itself. It was hearing story after story about small actions making a massive impact. A handwritten encouragement card to a student. A recruiter consistently following up with interns after events. A colleague reminding someone to breathe during a stressful week. A housekeeper who knows every student by name. A leader who trusts people instead of micromanaging them. Nobody described a “perfect leader.” But people kept describing leaders who were present. That matters! Especially in a world obsessed with speed, AI, automation, optimization, and doing more with less. Technology will absolutely continue to change education and hiring. But the human element still wins! One participant said: “Leadership isn’t a title but everyday action.” Another wrote: “I wasn’t sure what to think at first because sometimes motivational speeches can feel fake, but the actionable steps behind becoming a better leader were genuinely relevant and helpful.” Leadership is rarely one giant moment. Most of the time, it’s a thousand small interactions people never forget. What’s one small action someone took that made a lasting impact on you? Huge thank you to Toni Stangohr, Juan Ramirez, the WI-ACE team, and everyone who showed up fully engaged throughout the day.
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Derek Deprey posted thisYou Don’t Need a Team to Be a Leader I was coaching someone in a transition season. He’d just handed off operations. No more team. No more direct reports. He was gearing up to move across the country to rebuild a failing branch… solo. “So I guess I’m not really leading anyone right now,” he said. I paused... Then asked, “Who told you leadership requires a direct report?” That moment unlocked the rest of our session. We started listing the people he was already influencing: 1️⃣ A peer he’s coaching from afar 2️⃣ A cross-functional teammate he’s mentoring 3️⃣ A warehouse leader he’s championing, even though he’s not their boss 4️⃣ Future teammates who’ll join the team he’s building from scratch This is exactly why I wrote the book, Everyday Leaders: Small Actions, Big Results. Leadership is influence, not titles. It’s presence, not position. You don’t need a dotted line to lead someone. You just need a moment and the intention to make it matter. Who’s watching you right now? Who could use your support, even if they don’t report to you?
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Derek Deprey shared thisMindset changes everything. Some people look for the quickest way through the work. Others look for ways to improve, contribute more, and raise their own standard — even when no one is asking them to. The people who grow the most are usually the ones willing to stay humble, stay coachable, and keep learning after others become comfortable. Confidence is important. But growth often starts with the willingness to ask, “How can I get even better?”
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Derek Deprey shared thisYou’re Not Rambling. You’re Protecting Yourself. A theme that surfaced over and over in coaching surprised a few people in the room. Most over-explaining isn’t about lack of knowledge. It’s about protection. When leaders feel challenged, evaluated, or questioned, something subtle happens. Detail becomes armor. They add context to show they’ve thought it through. They add history to prove experience. They add explanation to avoid being misunderstood. And suddenly a 30-second answer becomes three minutes. It’s not random. It’s human. But clarity under pressure requires a different kind of discipline. One shift we worked on: Answer first. Then add context if needed. Then stop. It feels abrupt at first. It feels exposed. But it forces confidence. If you find yourself starting responses with “Well…” or “It depends…” pause and ask yourself what you’re about to protect. Sometimes the clearest answer is also the bravest one. Where do you feel the need to prove instead of serve?
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Derek Deprey posted thisThe Promotion Timeline Isn’t the Hard Part In a coaching call, a leader shared something that hit me right between the eyes. “The date is official. The transition is happening. It’s real." That is what a coaching client excitedly said to me. Most people think that’s the finish line. It’s not. The promotion timeline is the easy part. The hard part is everything that happens around it. People adjusting to new lanes. Old habits dying slowly. Team members still expecting you to carry the same load… even when you’ve clearly stepped into a new role. Here’s the tension. When you start leveling up, you have to stop doing work that made you “useful” so you can start doing work that makes you “necessary.” And that transition is messy. Not because your team is bad, but because humans are wired to keep the system the way it’s always been. If you lead people, ask yourself: Where are you still rescuing because it’s faster, easier, or “that’s how we’ve always done it”? And if you’re the one getting promoted, what do you need to stop doing so your team can finally grow into its full potential?
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Derek Deprey shared thisShe Heard What I Didn’t Say ☕️ I rolled into the Missouri Athletic Club late the night before a speaking event. The morning came quickly, and I looked like I had gone 12 rounds with a pillow that fought back. I’m also a bit of a coffee snob. “Hotel room” coffee? Not happening. If you know, you know. So I wandered down to the front desk, hoping for something fresh. Tyra smiled and said, “We don’t have coffee out until 7am.” All good. Life on the road teaches you to adjust quickly. I pulled up my phone, opened Lyft, and started planning a quick trip to Starbucks so I could caffeinate and prep before heading to speak for the Club Management Association of America St. Louis Chapter at Greenbriar Hills Country Club. Before I could finish booking it, Tyra said, “Sir, just give me 5 minutes.” She disappeared… and came back with a great cup of coffee from another floor, handing it to me right there in the lobby. Because of her, I stayed. I studied my presentation. I got into the right headspace. And I walked into that session ready. My topic that morning was "Leadable: Be Coachable. Become Unstoppable." -- the third book I’m writing and plan to publish in 2027. In the keynote, I teach listening... but not the kind of listening most people think about. Connection listening isn’t just hearing. It’s anticipating. It’s noticing what someone is about to need—before they have to ask. No policy told Tyra to do that. No script was required. She just paid attention. We talk a lot about “going above and beyond.” This is what it actually looks like. We need more Tyra’s in the world. Where can you anticipate a need, before it’s spoken? Sometimes the smallest move changes someone’s entire day. Special thank you to Andy Crowe, Rodney Stoyer, and Laura Hodges for having me. Grateful for the opportunity to be with your group.
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Derek Deprey posted thisThe Little Things AI Can’t Do Today, I picked Mia up from school and dropped her off at the gym to lift. It was one of those perfect Wisconsin days, so instead of joining her inside, Rachel and I decided to go for a walk outside. On our way back, I spotted someone I hadn’t seen in a couple years… my friend Chris Murphy, owner of Eddie Martini's. It was around 4:30pm, so Chris was dressed sharp in his suspenders getting ready for a packed night at the steakhouse. But what caught my attention had nothing to do with the restaurant itself. His back was turned to us out near the landscaping and flower beds, and he was bent over picking up a random styrofoam to-go box somebody had tossed on the property. Nobody around. No customers yet. No employees watching. No knowledge about a social media post coming about his courageous trash pickup leadership moment either. 😂 Just quietly doing the right thing. We talked for a while and caught up on life, leadership, and his new pickleball hobby that apparently every adult over 40 is now legally required to take up. Somewhere in the conversation, he mentioned remembering an article I wrote about an airport attendant who created memorable moments because she decided to put her personal stamp on the job and make people feel seen. Then Chris said something I haven’t stopped thinking about: “I’m not worried about AI… at Eddie Martini’s, we do the little things AI can’t do.” The little things nobody claps for are usually the things people remember most. How you greet people. How you handle details. How you treat someone when there’s nothing to gain. The standards you hold when nobody’s watching. That stuff still matters. More than ever. Rachel and I celebrated our 10th anniversary at Eddie Martini’s years ago. Hard to believe I blinked and our 20th anniversary is coming up on June 4th. I think it’s pretty obvious where we should celebrate again. 🥩🍽️ What’s a small leadership moment you observed recently that stuck with you?
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Derek Deprey liked thisDerek Deprey liked thisWe’re proud to see our CEO, Pat Kressin, featured on 620 WTMJ sharing insights on GRAEF’s leadership, the impact of our work in shaping communities, and what’s ahead for development in Milwaukee. It was a great conversation! Listen to the full interview here: https://lnkd.in/gV6tqPXu
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Derek Deprey liked thisAn exciting year ahead! I'm glad to be part of a group with such intelligent & enthusiastic leaders -- it definitely makes my job enjoyable. If you're a procurement leader in the Chicagoland area, we'd love to welcome you to our next event.Derek Deprey liked thisGreat conversations and exciting momentum at tonight’s ISM Chicago Board Meeting! Our board and committee leaders came together to discuss ISM Chicago’s strategic vision for 2026–2027 and share innovative ideas that will continue to strengthen value for our members and the procurement community. From professional development opportunities to networking events and new initiatives, there is a lot to look forward to in the coming year. A big thank you to our dedicated board members and committee volunteers for their leadership and collaboration that helps advance the procurement profession in Chicagoland and beyond. We’re excited about what’s ahead and look forward to continuing to build meaningful opportunities for you! #ISMChicago #Leadership #StrategicPlanning #Procurement #SupplyChain #ProfessionalDevelopment #Networking
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Derek Deprey liked thisDerek Deprey liked thisACI Solutions will be at AFCEA TechNet Cyber 2026 in Baltimore, June 2 to 4. Our President, Peter Martess, will be on the ground connecting with military, government, and industry leaders as they tackle one of the most critical conversations in federal IT right now: how to build resilience, defend networks, and dominate the digital battlespace. Exactly the kind of dialogue ACI Solutions is built for. If you will be there, reach out. We would love to connect. #TechNetCyber #AFCEA #Cybersecurity #GovCon #FederalIT #ACISolutions
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Derek Deprey liked thisDerek Deprey liked thisThis week I met with a CPA (Gretchen Vickney), an attorney (Rob Sullivan), a benefits consultant (Deena (Seehafer) Brown, PHR, MS), and a business investor (Shane Haness). No, it’s not the setup to a joke 🤣 it’s a reminder that the best people in business share the same values: ✔ High‑quality service ✔ Integrity ✔ A heart for small business ✔ A belief in collaboration over competition Two new connections. One follow‑up. One reunion after 20+ years. All proof that when you surround yourself with the right people, the work gets better —> and so does the journey. Here’s to building networks full of high‑quality professionals and future opportunities to work together for the benefit of our clients & network. #aHRrowLLC #smallbusiness #networking
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Derek Deprey liked thisDerek Deprey liked thisExciting things ahead! After nearly 13 years in my VP- Consumer Banking regional leadership position at Johnson Financial Group, I’m pleased to share that I’ll be stepping into a Vice President- Private Banking role. Over the past decade+, I’ve had the opportunity to manage and support branch leaders in Hayward, Spooner, and Rice Lake, and have thoroughly enjoyed helping coach and develop their teams. The addition of my new role as our first dedicated Private Banker for the NW Region of JFG has been long-awaited, and I am thrilled to provide concierge-level service to our Private Banking clients across the NW part of our state. Grateful for the relationships and friendships made, ones yet to be built, and such a wonderful organization to be a part of! https://lnkd.in/gWnzwCQXBrooke Harycki | VP Private Banking | Rice Lake, WIBrooke Harycki | VP Private Banking | Rice Lake, WI
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Derek Deprey liked thisDerek Deprey liked thisCheers to the Class of 2026! 🎓✨ From high school diplomas to advanced degrees, your hard work and investment in yourself has paid off. Whether your next chapter keeps you close to the Community First family or takes you on a brand new adventure, #TeamCFCU is incredibly proud of you.
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Derek Deprey liked thisDerek Deprey liked this📣 As May comes to a close, we’re proud to recognize incredible team growth through new hires & internal promotions at Midtown Athletic Clubs! We’re thrilled to welcome Katie Hunt, Digital Marketing Manager; Carley Mahoney, Social Media Manager; and Aman Kaur, Revenue Operations Specialist to our Corporate Marketing team! We can’t wait to see the impact they’ll make as they begin their journey with Midtown. 🚀 In addition, we’re thrilled to celebrate two well-deserved promotions! Vadym Stolyaryk has been promoted to Facilities Manager at our Midtown Weston, FL location. Since joining Midtown, Vadym has successfully led multiple large-scale projects, improved vendor relationships and services, & helped build out a strong facilities team. Joe Culotta has been promoted to Facilities Manager at Midtown Palatine. Since joining Midtown, Joe has since strengthened vendor accountability, brought a significant amount of preventative maintenance in-house, and built strong rapport with the senior leadership team & members. Please join us in congratulating, welcoming, and celebrating all! 🎉 #WelcomeToMidtown #MidtownTeam #MarketingCareers #Newhires #Careergrowth #FitnessCareers #Hospitality #GrowthAtMidtown
Experience & Education
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Volunteer Experience
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Keynote Speaker - Annual Fittest Exec's Awards Ceremony
BizTimes Media LLC
Health
Live Well, Lead Well: 5 Practices to Feel Better In Work and Life
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Speaker - Lunch and Learn
ASQ
Health
Live Well, Lead Well: 5 Practices to Feel Better In Work and Life
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Speaker - Women's Leadership Committee
Wauwatosa Chamber of Commerce
Health
Live Well, Lead Well: 5 Practices to Feel Better In Work and Life
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Speaker - National School Leadership Conference
WELS
Health
Live Well, Lead Well: 5 Practices to Feel Better in Work and Life
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Keynote Speaker - Annual Top 8th Graders Luncheon
WAUWATOSA ROTARY FOUNDATION INC
Education
Stand Out, Don't Fit In
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Speaker - Annual BizTimes Expo
BizTimes Media
Education
Developing the Leaders Around You: How to Help Others Reach their Full Potential
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Keynote Speaker
Career Renewal
- Present 8 years 2 months
Everyone Communicates, Few Connect: What the Most Effective People & Teams Do Differently
Languages
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English
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Organizations
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Society for Human Resources Management (SHRM)
Member
- PresentThe Society for Human Resource Management (SHRM) is the world’s largest HR professional society, representing 300,000 members in more than 165 countries. For nearly seven decades, the Society has been the leading provider of resources serving the needs of HR professionals and advancing the practice of human resource management. SHRM has more than 575 affiliated chapters within the United States and subsidiary offices in China, India and United Arab Emirates.
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National Speakers Association - Wisconsin Chapter (NSA-WI)
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National Speakers Association (NSA)
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- PresentThe National Speakers Association (NSA) is a collective of more than 3,400+ members whose skills, expertise and experience power the most recognized and respected professional speakers organization in the industry. Founded in 1973 by Cavett Robert, CSP, CPAE, NSA has the comprehensive resources, cutting-edge tools, insightful education and productive events that speakers need to develop their brands and grow their businesses. NSA’s members include experts in a variety of industries and…
The National Speakers Association (NSA) is a collective of more than 3,400+ members whose skills, expertise and experience power the most recognized and respected professional speakers organization in the industry. Founded in 1973 by Cavett Robert, CSP, CPAE, NSA has the comprehensive resources, cutting-edge tools, insightful education and productive events that speakers need to develop their brands and grow their businesses. NSA’s members include experts in a variety of industries and disciplines, who reach audiences as speakers, trainers, educators, humorists, motivators, consultants, authors and more. We have 35 independently run state and regional chapters throughout the U.S.
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International Health, Racquet & Sportsclub Association (IHRSA)
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- PresentIHRSA’s mission is to grow, protect, and promote the health and fitness industry, and to provide its members with the benefits that will help them be more successful. IHRSA and its members (health clubs and fitness facilities, gyms, spas, sports clubs, and industry suppliers) are dedicated to make the world healthier through regular exercise.
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