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Are leaders asking the right questions?
The water of the Ohio River was colder than I expected that morning in Louisville. Not the bracing cold that shocks you into clarity, but the kind that seeps into your bones slowly, the kind that whispers that this might not be your day. The year prior, the water was choppy, with a murky, oily taste. Yet, here I am again.
It wasn’t my first time in these waters. In 2017, I had stood at this same starting line, my training plan meticulously documented, every workout logged, every interval timed. I made it 80 miles on the bike before my body simply refused. The following year, I returned. Previously, I had struggled to begin the swim portion of the race. Two DNFs. Two “Did Not Finish” stamps on my carefully constructed identity as someone who completes what they start.
Bob Hurley, the legendary high school basketball coach, keeps his practice plans for years. He files them away to compare his current quality of practice against previous seasons. Not to romanticize the past, but to ask himself the most essential question a leader can ask: Is the issue before us real?
That’s the first question on the whiteboard in my office. I use this first question as a gauge to stop me from spiraling into solutions for problems that exist only in our anxious imagination, or worse, before we ignore problems that are catastrophically real.
Standing in that cold water for the second time, I had to ask myself: was my issue real, or was I manufacturing drama around discomfort and the unknown? The cramping was real. The hypothermia was real. My sore body pulsed with each heartbeat. But were these the actual issues, or were they symptoms of something deeper—something I hadn’t yet named?
The Practice of Honest Examination
Hurley teaches that you can’t wing practices, that you must plan in advance, and critically, that you must stick to what you write down. There’s a discipline to this that borders on the spiritual. In a world that celebrates pivoting and adapting, there’s something almost countercultural about committing to a plan and seeing it through—not out of stubbornness, but out of respect for the process itself.
But here’s what I learned in those cold waters: sticking to the plan is not the same as refusing to see what’s true.
My first two attempts at triathlon were failures not because my training plans were wrong, but because I had never truly asked: What is the issue and challenge before me? I had conflated the distance with the difficulty. I had assumed that more volume, more miles, more suffering in training would equal success on race day. I had treated my body like it was simply a matter of will, as if I could bully it into submission through sheer determination.
For me, it wasn’t fitness. It was fueling. It wasn’t mental toughness. It was pacing. I had been practicing the wrong things, with great discipline, for years.
When The Issue Appears
Hurley splits practice time: two-thirds on individual skills, one-third on team concepts. He knows that the team cannot rise above the sum of its parts if those parts haven’t been properly developed. But he also knows something else—something that took me two failures to understand: When is the issue most present?
In my case, the magnified issue appeared at mile 80 on the bike—but it didn’t originate there. It originated in training sessions where I pushed through hunger, where I told myself that eating was for the weak, where I confused deprivation with dedication. The issue was most present in the glamorous moments of race day, but it was born in the unglamorous moments of Tuesday morning training runs.
Leaders often mistake the battlefield for the war room. We believe issues and challenges arise during the crisis, in the big presentation, and in the championship game. But Hurley knows better. He runs special-situation practices every two weeks, cycling through twenty different scenarios. He’s not waiting for the issue to appear in the game. He’s summoning it in practice, where the stakes are lower and the learning can be pure.
After my second DNF, I changed my approach entirely. I started eating during every training ride over two hours. I practiced taking nutrition at race pace. I made fueling a skill, not an afterthought. I treated it with the same respect I gave to my intervals and tempo runs.
This is what it means to ask: How do I address the issue to overcome the challenge? Not theoretically, not in the abstract, but in the daily grind of practice where no one is watching and there are no finisher medals.
Ownership and Accountability
Hurley has a concept I deeply value: players are responsible for the mood and for correcting mistakes.
Who addresses the issue? Who owns the issue?
These questions live right next to each other on my whiteboard because they’re inseparable. For too long, I had treated my coaches, my training partners, my online communities as the owners of my success. I showed up to group rides and let others set the pace. I followed training plans without understanding the principles behind them. I had surrounded myself with expertise but had never taken ownership. Worse yet, I did not honor and humble myself to the journey.
When I toed the line for the second time in Louisville, ownership now means standing on business, knowing exactly why I was there and what I needed to do. Every decision was mine. I cannot hide. Presence matters. Effort matters. Ownership matters.
The Question of Importance
Why is this issue important to address?
I’ve come to believe this might be the most dangerous question on the whiteboard—dangerous because it can so easily become an excuse for inaction. We can convince ourselves that some issues aren’t worth addressing, that some problems are simply the price of doing business, that some failures are acceptable.
Hurley would say: practice to improve the team first, focus on your opponent second. There’s a priority structure here that’s easy to miss. The issue is important to address because it will make you more of what you’re meant to be. I didn’t need to complete an Ironman. My life would have gone on. My worth as a person wasn’t tied to a finisher’s medal. But the issue and challenge were important to address because of what they revealed about how I approached difficulty and how I responded to failure. The issue is important to address, not because we might fail, but because if we don’t address it, we’ll never know what we’re capable of.
The Mathematics of Impact
How many people are impacted by the issue?
When I didn’t finish my first triathlon, I told myself it only impacted me. When I didn’t finish my second, I started to see the truth: my family had rearranged their schedules to be there. My training partner had invested hours in my preparation. Despite the extensive investment in preparation, including podcast listening and reading, the outcome was still failure.
Leadership isn’t a solitary endeavor, even when it feels like one. Even in an individual sport like triathlon, we are never truly alone. The question isn’t whether others are impacted—they always are. The question is whether we’re willing to see them, to acknowledge that our issues ripple outward in ways we can’t fully predict.
The Cost of Inaction
What would happen if we did nothing?
The final question on the whiteboard. The one that strips away all pretense.
If I had done nothing after my second DNF—if I had simply accepted that Ironman racing wasn’t for me—my life would have moved forward. I would have found other challenges, other ways to test myself. But I would have carried something with me: the knowledge that when things got hard, when I faced something that required fundamental change rather than incremental improvement, I folded.
Hurley would understand this. He teaches that everything else you practice is worthless if you can’t take advantage of scoring opportunities. It’s a brutal calculus, but it’s true. You can drill for hours, you can perfect your technique, you can build team chemistry—but if you can’t finish, none of it matters.
The water in Louisville on my second attempt was still cold. My body still hurt. Doubt still whispered in my ear at mile 80. But this time, I had done something different: I had asked the questions. I had named the issues. I had taken ownership. I had made the necessary changes.
The Gift of Completion
When I crossed that finish line—14 hours and 36 minutes after starting—I didn’t feel the euphoria I’d imagined. I felt something quieter, something more durable: I felt like someone who had finally learned to ask the right questions.
Hurley ends each practice on a positive note, rewarding players for effort. He starts and ends each day with a meeting—starts on a positive note, ends on a positive note. There’s wisdom in this ritual that goes beyond motivation. It acknowledges that the work is never done, that tomorrow we’ll face new issues, that completion is not the same as perfection.
The blog post you’re reading now is less about a tutorial on how to finish an Ironman. It’s about how to lead when the plan isn’t working. It’s about the difference between documentation and examination, between training hard and training smart, between finishing and quitting.
The water will always be cold. The distance will always be far. The issues will always be real. But the questions—those nine questions on my whiteboard—they’re the map. And sometimes, that’s the only distance that matters: the space between the question we’re afraid to ask and the truth we’re finally ready to hear.
Dr. Darryl S. Diggs, Jr.
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“I always feel like it’s two key ingredients when it comes to following your dreams, making something happen that the average person deems difficult. If you truly believe it, that’s step one. Step two, is, you know, the hard work that goes along with it.” – J.Cole
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