The Art of Making Hard Calls: Why Great Leaders Must Embrace Failure

I used to be paralyzed by big decisions. Not the easy ones—everyone can handle those. I'm talking about the decisions where you don't have enough information, the stakes are high, and you need to move fast. The kind where your name gets attached to the outcome, and if it goes wrong, everyone knows it was your call.

For years, I did what most people do: I hedged my bets. I involved so many people in decisions that if things went south, the blame would be diffused. I asked for more data, more time, more consensus. Anything to avoid being the person whose decision failed.

Then I learned something that changed how I think about leadership entirely: the most respected leaders aren't the ones who never fail—they're the ones who own their failures and learn from them publicly.

Why We Avoid Making Hard Calls

Let's be honest about what we're really afraid of. It's not the decision itself—it's the possibility of being wrong. When you put your name on a decision and it bombs, your name is on it. Everyone sees it. Your boss sees it. Your team sees it. And in a world where people are trying to keep their jobs and advance their careers, that exposure feels dangerous.

So we develop elaborate strategies to avoid accountability. We form committees. We ask for more research. We delay until the decision makes itself or someone else is forced to make it. We convince ourselves this is prudent leadership when really it's just fear.

But here's what I've learned after making plenty of wrong calls: life generally goes on. The first time one of my decisions really backfired, I thought it might be career-ending. Instead, I discovered something unexpected. When I stood in front of my team and said, "I made that decision, it didn't work, I own it, and here's what I learned," the respect in the room was palpable.

People don't lose confidence in leaders who make mistakes—they lose confidence in leaders who can't make decisions at all.

What Makes a Decision "Hard"

Not every difficult decision is what I consider a "hard call." Hard calls have two specific qualities that make them particularly challenging: they have to be made quickly, and you don't have enough information to be certain you're right.

This is different from complex decisions where you have time to gather data, consult experts, and build consensus. Those are hard work, but they're not hard calls. Hard calls happen when market conditions are shifting, when competitors are moving, when opportunities have expiration dates.

If you've ever worked for someone who couldn't make yes-or-no decisions under these conditions, you know the particular pain it causes. Teams get stuck. Momentum dies. Opportunities slip away while everyone waits for a decision that never comes.

I call this quality "edge"—the ability to make a decision and make it quickly when the situation demands it. If you don't develop this capability, you'll get a reputation as someone who can't lead when it matters most.

The Power of Pattern Recognition (And When It Fails)

People often talk about "going with your gut" in decision-making, but I think that's misleading. Your gut isn't some mystical force—it's pattern recognition. When you've seen similar situations before, your brain connects the dots and suggests what's likely to happen next.

This works great when you're dealing with familiar patterns. If you've launched products before, managed similar teams, or navigated comparable market conditions, your pattern recognition can be incredibly valuable.

But here's the problem: in today's business environment, we're constantly facing situations with no clear pattern. Technology is changing the rules, markets are shifting in unprecedented ways, and what worked last year might be completely irrelevant now.

When there's no pattern to recognize, you can't rely on gut instinct alone. You need systematic ways to think through decisions.

My Framework: The 10-10-10 System

After making some spectacularly bad decisions early in my career, I started looking for better ways to approach hard calls. I experimented with various frameworks until I found one that consistently helped me make better decisions: the 10-10-10 system.

It's embarrassingly simple, which is probably why it works. Here's how it goes:

First, I write down all the realistic options. Not just the obvious ones, but the creative alternatives that might not be immediately apparent. Sometimes the best decision is option D that nobody initially considered.

Then, for each option, I think through the consequences across three time horizons:

• Ten minutes (immediate consequences)
• Ten months (medium-term implications)
• Ten years (long-term impact on what we're trying to build)

The specific timeframes aren't magic—they're directional. The point is to force yourself to think beyond just the immediate impact and consider how each choice affects your longer-term goals.

I create a simple grid and fill in the consequences for each option across all three timeframes. Then I step back and ask: given our values as an organization and what we're trying to achieve, which option best aligns with our goals?

Why This Framework Actually Works

What I love about this approach is that it forces you to be explicit about your assumptions. When you write down that Option A will lead to X outcome in ten months, you're making your reasoning visible to yourself and others.

This is particularly powerful when you're working with a team. People can push back on your assumptions. "You're saying that's going to happen in ten months, but I don't think that's realistic based on what we've seen before." Having everything laid out makes it easier to test your thinking and catch blind spots.

It also helps you understand the trade-offs you're making. Maybe Option A looks great in the short term but creates problems down the road. Maybe Option B is painful now but sets you up for long-term success. The framework doesn't make the decision for you, but it helps you see the full picture.

When You Need More Structure: Decision Trees

For particularly complex decisions—especially ones with significant financial implications—I sometimes use decision trees. These are more sophisticated tools that map out all possible branches of a decision and their potential outcomes.

You start with the main decision node, then branch out to show all your options. From each option, you create sub-branches showing all the possible things that could happen next, along with their probabilities and financial impacts.

This sounds complicated, and it can be. Some decision trees are massive, with dozens of branches and sub-branches. But the process of building one forces you to think through scenarios you might otherwise miss.

The good news is that technology has made this much easier. There are software tools that help you build decision trees, and AI is making them even more powerful by helping identify scenarios and calculate probabilities.

The Importance of Wallowing (Before You Decide)

I want to be clear about something: moving fast doesn't mean moving recklessly. Before I make any significant decision, I spend time "wallowing" in it—gathering different perspectives, especially from people who might disagree with my initial instinct.

I'll often tell my team, "This is what I'm seeing. What am I not seeing?" I want to hear the counterarguments, the potential downsides I haven't considered, the alternative approaches I might have missed.

But—and this is crucial—after you've gathered the input and done the analysis, you have to actually make the call. The wallowing phase has to end. You can't stay in research mode forever.

What Happens When You Get It Right

When you develop a reputation for making good decisions quickly, several things happen. Your team starts trusting you more because they know you won't leave them hanging when tough choices need to be made. Your superiors start giving you more responsibility because they know you can handle pressure situations.

But perhaps most importantly, you become more confident in your own judgment. Each decision you make—whether it works out or not—teaches you something about how to think through complex situations.

And when you do make mistakes? You own them, learn from them, and move on. Your team sees that failure isn't the end of the world, which makes them more willing to take risks and make their own hard calls.

The Meta-Skill of Leadership

At the end of the day, decision-making is the meta-skill of leadership. You can be brilliant at strategy, amazing with people, and expert in your field, but if you can't make hard calls when they're needed, you'll never be truly effective as a leader.

The irony is that getting comfortable with hard decisions requires accepting that you'll sometimes be wrong. The leaders who never make mistakes are usually the ones who never make decisions that matter.

Work is just one decision after another—about pricing, about people, about priorities. The organizations that move forward are led by people who can navigate uncertainty and make calls without perfect information.

That's not a natural talent—it's a skill you can develop. You just have to be willing to put your name on some decisions that might not work out. And when they don't, you have to be ready to own the outcome and learn from it.

That's how you build edge. That's how you become someone others trust to make the hard calls.