 Many organizations have formal mentorship programs, especially for employees showing potential for leadership roles. And I’m not knocking that. I’ve seen some great mentor-mentee relationships come from structured pairings. But I’ve also seen some forced matches that feel more like a corporate version of speed dating: awkward, ineffective, and destined to fizzle out by Q2.
So let’s talk about the mentor side of that equation. According to the dictionary, a mentor is “an experienced and trusted adviser.” Not just someone who knows the ropes, but someone the mentee trusts to help them navigate the climb. That second part, the trust, can’t be assigned. It has to be earned. And that’s where some programs miss the mark. Let me share a story. While serving as a superintendent at the Air Force leadership school in Florida, I also taught martial arts a couple nights a week. One of my students worked in Security Forces; the Air Force’s military police, and also my old stomping grounds. This young airman had mentioned a few times how disconnected he felt from leadership. He didn’t feel like anyone really had his back. Then one night, around 10 or 11pm, he called me. He was going through some personal challenges and just needed someone to talk to. So I said, “Come on over.” We sat and talked for hours, about his professional frustrations, his personal life, and how all of it was starting to bleed into his performance. I knew exactly what he meant when he said Security Forces could be unforgiving. We had a reputation of “eating our own” when someone was struggling. I’d seen it. I’d lived it. And I wasn’t going to let him go through it alone. I gave him some guidance. Not “fix it all” advice, but real talk; how to approach leadership, how to advocate for himself, and how to handle the personal side so it didn’t derail his career. We stayed in touch long after I retired. We still talk today. He didn’t stay in the military like I did, but he’s doing big things now; he started a tech company that helps transitioning service members. In other words: he’s mentoring people who need it, just like he once did. Now, here’s the thing: I was never officially his mentor. Nobody assigned me. We didn’t fill out any forms or schedule quarterly check-ins. He found someone he connected with, someone who understood his goals, his struggles, and the context he was operating in. That made all the difference. That’s why I believe mentorship works best when it’s mutually chosen. When the mentee finds someone who aligns with their values, goals, and personality, and when the mentor genuinely wants to help that person succeed on their terms, not just turn them into a carbon copy of themselves, that’s when growth happens. Sure, structured programs have their place. But, if you’re serious about developing real leaders, make room for the kind of mentorship thats built on connection…not convenience. The right mentor doesn’t just show up on a roster…they show up when it matters most.
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 Every year, like clockwork, my wife Melissa has made sure each of our four kids started the school year with a new backpack and a new lunchbox.
Now, we’ve been married nearly 30 years, and while I’ve always admired how intentional and thoughtful she is as a mother, I’d sometimes joke and ask, “Why do they need a new backpack and lunchbox again? Last year’s still looks fine!” Sure, I understood the new pencils, folders, and notebooks, those get used up. But backpacks? Most of them were still in good shape. So why spend the extra money? It took me a while to fully understand what Melissa already knew. It’s not about the backpack. It’s about how it makes them feel. That new backpack says to a child: “You matter. This year is a fresh start. You can do this.” Even something as simple as a new lunchbox can give a child a spark of confidence. And when they feel better about themselves, it shows. They walk into that classroom a little taller. They participate more. They feel prepared, and not just with supplies, but with a sense of identity and self-worth. I’ve seen it happen. A new year, a new backpack, and suddenly the same child who was withdrawn or struggling last year seems more motivated and engaged. It’s not magic—but it is meaningful. It’s a reset button. If the last school year ended with tough grades, social struggles, or bullying, a fresh start, symbolized by something as simple as a new backpack, can offer quiet reassurance: You’re not stuck in last year’s story. And Melissa didn’t stop at just the backpack and lunchbox. Every day, she tucked a note of encouragement or affirmation into our kids’ lunchboxes. Nothing long, just something timely and relevant. A “good luck on your test today,” or “Have a great day. I love you.” Little things with big impact. When our kids opened their lunchbox, they weren’t just fed…they were seen and supported. The Leadership Lesson in Parenting As parents, we sometimes default to logic, if it still works, why replace it? But kids don’t just operate on logic. They operate on emotion, identity, and encouragement. Sometimes, the best parenting decision isn’t about function, it’s about what fuels their spirit. And here’s something I’ve learned over the years as a father, martial arts instructor, and leadership coach: When people feel prepared and valued, they show up differently. That applies to our kids too. When they believe they’re stepping into something new, something they have control over, they carry themselves with more confidence. The ROI on That $25 Backpack Let’s be real, a new backpack or lunchbox each year isn’t a necessity. But if it motivates your child to engage more, stand taller, try harder, or believe in themselves just a little more…is it really unnecessary? In our home, Melissa never saw it as just a purchase. She saw it as a message: one of love, belief, and possibility. And if you ask me, that’s the kind of leadership our kids need most from us.  When I volunteered for recruiting duty in the Air Force, it was pitched as a prestigious position. One of the best sales schools in the country. High autonomy. Big impact. All true. What wasn’t included in the sales pitch? The pressure. The long hours. The emotional drain. Or the fact that it was one of the most stressful assignments outside of combat operations.
Still, I thrived in it. But I’ll never forget one particular quarter when I had a spike in cancellations; applicants who had to drop out due to things completely out of my control: injuries, legal issues, pregnancies. Even though I had no hand in those outcomes, they still counted against me. That’s how the system worked. Because of that spike, a training team from headquarters scheduled a visit to “evaluate” my situation. That really meant: they were coming to see if I’d done anything wrong. The day before their visit, I had a 101-degree fever. When I woke up the next morning, still at 99, I suited up and went in anyway. That’s just who I am. My supervisor, who was ordered to be present, was already sitting at my desk when I walked in. He looked at me and said, “You look sick.” I replied, “I am.” And then he said something I’ll never forget: “You know what you need to do?” “What?” “Make goal…so you can take some time off.” Now, I made goal that quarter. The training team came and went. But that moment stuck with me. I thought about the fact that he could have, and should have sent me home. He had access to all the data. He knew I hadn’t dropped the ball. And if he had stepped in for me, I would’ve been out a day or two at most, instead of potentially sidelined for much longer. Fast forward a few months: another office on our 10-person team was about to miss goal again. My supervisor called me up and said, “I know you already made goal. Do you have any applicants you can send up so we can make mission?” Now here’s the thing, any good sales person knows the game. You don’t use up next month’s numbers unless you have a reason. I had a couple applicants ready. But I remembered how he treated me when I was sick. I remembered how he looked out for himself instead of his people. So I told him I didn’t have anybody to send. Here’s the Leadership Lesson: Your people might respect your position, but they won’t go the extra mile for you just because of your title. They go the extra mile when they know you’ll do the same for them. That’s how trust and influence are built. Not in the big motivational speeches, but in the small, human moments where you prove you’re in it with them. Had he done the right thing back then, sent me home and stepped up, I likely would’ve gone out of my way to help him hit his goal. Instead? He missed it. And I took a well-earned day off. |
AuthorCliff Kinchen is a lifelong martial artist and seasoned leadership trainer who blends combat discipline with real-world leadership insight. With decades of experience—from Air Force instruction to corporate boardrooms—he helps others grow through confidence, character, and challenge. His writing sparks reflection, inspires action, and invites readers to lead from the inside out Archives
September 2025
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