Problem Solving: Why the Best Leaders Don’t Wait for the Answer
“We cannot solve our problems with the same thinking we used when we created them.”
- Albert Einstein
Problem solving isn’t a bonus skill—it’s the job. And if you’re in a leadership role, hoping someone else will make the tough call, you’re already behind. The real leaders don’t sit back and wait for the storm to pass—they walk straight into it with clarity and command.
Every organization has friction. Every mission faces resistance. The difference lies in how quickly and effectively it gets resolved. Elite problem solvers don’t need all the information to act. They’ve built the instincts to move when it counts. The rest? They wait, they waffle, and they wonder why momentum keeps stalling.
Great Problem Solvers Keep the Machine Moving
People think leadership is about inspiration. But when pressure hits, what they really want is certainty. A great problem solver brings that certainty, not through perfection, but through decisiveness. They don’t flinch. They don’t over-explain. They move. And because they move, the machine continues to move. There’s no meeting backlog. No confusion spreading like a virus. Just steady progress because someone had the guts and the reps to step up and solve what needed solving.
That’s what Dwight D. Eisenhower understood on the eve of D-Day. Thousands of lives, years of preparation, and the entire momentum of the war rested on a single call—and he made it. He didn’t delay. He didn’t deflect. He acted. Not because it was easy, but because the machine couldn’t afford to stall. That one decision—to move forward despite uncertainty—kept the largest military operation in history on pace and intact. Eisenhower wasn’t revered for his speeches. He was respected for his clarity when it mattered.
In sports, that same clarity has kept Bill Belichick’s teams competitive for decades. He doesn’t coach through slogans or emotion. He coaches through structure. His players never wonder what’s expected—they know. Systems are in place. Roles are defined. Chaos gets neutralized before it spreads. When a problem hits, Belichick doesn’t crowdsource solutions—he solves it. The result? Teams that move with efficiency even when the play breaks down or the moment gets big.
Trust flows to those who carry the burden of responsibility without hesitation. The faster you can identify the right move and execute it, the more faith your people will place in your leadership. That faith isn’t built on charisma. It’s built on consistent execution in high-pressure moments. And it’s reinforced every time the leader at the top refuses to flinch when the stakes are high and the fog rolls in.
Boyd’s OODA Loop: Decision-Making at Combat Speed
John Boyd (Boyd: The Fighter Pilot That Changed the Art of War) didn’t build theory in a classroom—he built it under fire. As a fighter pilot, he created a decision-making loop that military leaders and corporate strategists still lean on to this day: Observe. Orient. Decide. Act.
· Observe: see the problem
· Orient: understand what the main issues of the problem are
· Decide: decide what is the best course of action
· Act: put into action the solution that you came up with
Boyd’s brilliance was speed. The fighter who moved through this loop faster didn’t just survive. He dominated. He got inside the opponent’s mind, disrupting them before they could even react. He modeled this off the German Blitzkrieg strategy: strike fast, disrupt the system, and never give the enemy time to catch up.
Slow pilots were dead pilots. In business, slow decision-makers will kill their company.
You Can’t Learn This in a Classroom
There’s a reason books and lectures can’t teach real problem solving. They offer templates, not timing. They show scenarios, not stress. The only way to lead through conflict is to be in it, over and over again. Great leaders solve the small stuff daily, not because it’s fun, but because it prepares them for when the big problems show up without warning.
That’s why detachment kills leadership. If you’re not in the meetings, not reading the room, not paying attention to the moving parts, you’ll always need secondhand information to catch up. And by then, the problem’s already compounded.
In football, coaches use scrimmages to teach their players to move and react at near-game speeds. It is easy to sit in a temperature-controlled meeting room in a big, cushy seat with a bottle of water in your hand and tell a coach what you “would” do in a specific situation. But what happens when you make it a blizzard in Buffalo, it’s the fourth quarter, and you need a stop? How does that change the problem-solving time clock?
You want speed? Then stop making the problem solver comfortable. Put them in stressful situations in real time, in real conditions. This is where you will find your leaders.
Decision-Making Is a Muscle
The best problem solvers aren’t guessing. They’re trained. They’ve built this skill by leaning into the gray areas, making uncomfortable calls, and learning from every outcome. They don’t panic because they’ve been here before. And the people who work for them can feel it. The calm. The clarity. The control.
Contrast that with the leader who’s constantly blindsided. The one who needs a slide deck and three analysts before making a move. While they’re processing, their competition is executing. While they’re looking at trend lines, their team is losing faith.
Problem solving is a contact sport. You only get better by being in the arena—so if you’re asking how to strengthen that skill, stop looking for simulations and start building it in real time:
Trust YOU: Make the small decisions yourself, especially when they’re messy or unclear. That’s where instinct sharpens.
CSI Everything: Run post-mortems after both wins and losses, not to relive the result, but to dissect the process.
Communicate: Speak with the people closest to the issue, not those who are polishing the summary. That’s where the truth lives.
History Rewards the Bold, Not the Hesitant
Boyd’s OODA loop wasn’t theory—it was survival. It was clarity under pressure. And in leadership, that same clarity separates those who talk from those who act.
We live in a world addicted to certainty. Leaders wait for clean data, perfect timing, or someone else to flinch first. But by the time it’s safe, it’s often too late. In war, hesitation costs lives. In leadership, it costs trust, opportunity, and momentum you can’t get back.
I’ve seen it firsthand.
At one of my coaching stops, we had a culture problem brewing. It wasn’t loud, but it was leaking. The team leaders weren’t aligned. Some were loud, charismatic, and individualistic. The others were quiet, disciplined, and focused. I knew the tension was real, and I believed that the organization's leadership would make the bold choices. I waited. I rationalized. I took care of my room.
Then we didn’t make the play-offs. Not because of talent. Because of fractures. Divided leadership. Unspoken resentment. And that’s what still bothers me. I tried everything in my power to right the ship, but the decision makers blinked. They didn’t cut out the weeds, and eventually, they choked out the focused leaders.
Great leaders don’t wait for consensus. They don’t take attendance before they take action. They don’t hope it will fix itself. They move. They make the hard decisions. Make the deep cuts. All to save the culture.
Reps Build Readiness. Readiness Solves Problems.
You want to be a great problem solver? Then earn it.
Step into chaos with confidence.
Cut through noise with clarity.
Make the call (with confidence) when no one else will.
Reps build readiness. Readiness builds trust. And trust wins games, builds businesses, and saves teams from collapse.
You’ll never have all the answers. You’ll rarely have ideal timing. But if you’ve put in the reps—and you’ve built the courage—then you don’t need perfect conditions. You just need the next step.
The real leaders don’t freeze. They decide. They act. They keep the mission moving forward.
