Most of us learn leadership the hard way, one painful lesson at a time, over years. My guest has thirty of those years, and he's here to hand you the shortcuts. In this episode of Leadership Happy Hour, I sit down with Kevin Gregar, a retiring Army colonel who spent more than three decades getting the best out of people, to talk about what actually changes when you lead for that long.
We get into how to pull real value from different perspectives when you're solving hard problems, what worked thirty years ago that would fail badly today, and the moment Kevin learned that rigorous process means nothing without genuine care for people. He also makes the case that too many leaders are bolting AI onto broken process, and what to do instead.
Grab a drink and pull up a seat. You'll leave with one move you can make this week.
In this episode
- The shift from doing the work to leading the people
- Bringing in different perspectives when you're solving complex problems
- Using difference when the stakes are high and the clock's running
- What worked thirty years ago that fails today
- Why process means nothing without genuine care for people
- Where to start with AI if you feel behind, and why process comes first
- The one painful lesson you can skip
Timestamps
00:00 Welcome to Leadership Happy Hour00:42 Meet Kevin Gregar01:33 Looking back after thirty years in uniform02:19 The shift from doing to leading: empower, then get out of the way05:50 Why consistency and having their back changes everything07:48 Solving complex problems: bringing in different perspectives10:20 Using difference when the stakes are high14:33 What worked thirty years ago that fails today18:56 Process versus people: when process alone isn't enough24:34 AI: where to start if you feel behind27:11 Get the process right before you add AI28:07 The one painful lesson you can skip30:17 Thanks and close
About the guest
Kevin Gregar is a retiring U.S. Army colonel who spent more than thirty years in uniform, twenty-six as an officer, leading everything from small teams to large global commands, including running a $5.4 billion industrial operation across 23 facilities. He pairs rigorous process and accountability with genuine care for the people doing the work, and he's an early adopter of AI in enterprise operations.
About the host
Alesia Briggs is a Certified Executive Coach and founder of Briggs Consulting. Leadership Happy Hour is her show where leaders pour a drink, skip the theory, and talk about what actually makes them better. Find her at coachbriggs.com.
Links
Work with Alesia: coachbriggs.com | New episodes every week