You can spot a leader with real judgment from across the room. They’re the ones who somehow know exactly how long that integration will actually take (spoiler: longer than engineering thinks), when to push the team harder, and when to step back and let them breathe. They set ambitious goals that feel impossible but turn out to be just barely achievable with the right effort and focus.
Then there are the other leaders. The ones who promise the moon by next Tuesday, ignore their teams feedback when reality hits, and wonder why morale keeps tanking.
The difference isn’t talent. It’s judgment. And judgment doesn’t come from an MBA or a promotion—it comes from years of getting things wrong, learning why, and building instincts you can’t teach in a classroom.
Experience Builds the Judgment Muscle
I’ve watched this pattern play out for twenty years across Microsoft, startups, and enterprise companies. The leaders who consistently deliver aren’t the smartest people in the room or the best at PowerPoint presentations. They’re the ones who’ve been through enough product cycles to recognize the patterns.
They know that the “quick integration” will uncover three other systems that need updating. They’ve seen what happens when you push a burned-out team past their breaking point versus when you can rally them for one more sprint. They understand the difference between a stretch goal that energizes people and an impossible target that just breeds cynicism.
This judgment comes from making mistakes across different contexts. Leading a team at a 50-person startup teaches you different lessons than managing product strategy at a Fortune 500 company. Working with a scrappy engineering team that ships fast and fixes later gives you different instincts than leading enterprise software development where downtime costs millions.
The leaders with the best judgment? done both. They’ve felt the pressure of running out of runway at a startup and the complexity of coordinating across multiple business units at a large. They’ve learned when each approach works and when it doesn’t.
The Wild Ass Goal Paradox
Here’s what separates great product leaders from the rest: they know how to set what I call “intelligent impossible goals.” These are targets that sound crazy but are actually grounded in deep understanding of what their team can accomplish
A leader with good judgment looks at a team that’s been shipping incremental improvements for months and says, “What if we rebuilt this entire user experience in six weeks?” They know it’s technically possible because they understand the codebase, the team’s capabilities, and exactly where the current bottlenecks are. More importantly, they know their people are ready for a challenge that will push them to think differently.
A leader without judgment looks at the same situation and says, “Let’s launch in three different markets simultaneously while also rebuilding the.” They’re not considering dependencies, resource constraints, or whether the team has the bandwidth to execute well on multiple fronts.
The first goal energizes the team because it feels hard but achievable. The second one creates stress and eventual failure because it ignores reality.
When Inexperience Becomes Dangerous
I’ve seen too many promising leaders derail their teams because they never developed this judgment. They came up through one company, in one role, with one type of product. When they finally get the chance to lead, they apply the same playbook regardless of context.
They set deadlines based on what they think should be possible rather than what actually is possible. When their teams miss these arbitrary targets, they double down—demanding hours, more meetings, clearer accountability. They treat execution problems as motivation problems.inely don’t understand why their approach isn’t working. In their limited experience, pushing harder always worked. They never read the difference between a team that needs motivation and a team that needs realistic expectations.
Building Judgment Deliberately
The good news is that judgment can be developed, but it requires intentional effort. You can’t just wait for experience to happen to you.
Seek diverse contexts. If you’ve only worked at large companies, spend time understanding how startups operate. If you’ve only done consumer products, learn enterprise software. Each context teaches you different lessons about what’s possible and what isn’t.
Study your failures deeply. When a project goes sideways, don’t just fix it and move on. Understand why your initial estimates were wrong. What signals did you miss? What assumptions proved false? The patterns you identify become the foundation of better judgment.
Learn to read your team’s capacity. This is more art than science, but you better at it. Pay attention to how people respond when you propose aggressive timelines. Watch for the difference between healthy stress and destructive pressure. Notice when pushing harder actually slows things down.
Question your own certainty. Leaders with poor judgment are often the most confident ones. They’ve never been wrong enough times humility. When youd yourself absolutely certain about a timeline or approach, that’s exactly when you should seek other perspectives.
The Long Game
Building real judgment takes time—usually decades. There’s no shortcut to understanding how different teams respond to pressure, how various technical architectures affect development speed, or how market conditions change what’s possible.
But here’s what you can control: the diversity of your experience and how deeply you learn from it. Every project that goes differently than expected is data. Every team that responds unexpectedly to your leadership is feedback. Every market that doesn’t behave as predicted is education.
The leaders who develop the best judgment are the ones who collect this data systematically and let it change how they think. They don’t just accumulate years of experience—they accumulate years of learning from experience.
That’s how you build the inst you set those intelligent impossible goals, the ones that push your team to achieve things they didn’t think they could do. And that’s how you avoid becoming the leader who promises the impossible and then wonders why everyone stopped believing in the vision.