Long before I became a CEO, I played international cricket for the United States. The lesson I draw on most in business is this: Before deciding how aggressively to play, you have to read the pitch.
In cricket, the pitch is the strip of ground at the center of the field. Its condition can change the game. On one surface, 200 runs might be an excellent score. On another, 400 may be achievable. You have to judge the surface, the opposition, and your team.
Misread it, and you can execute exceptionally well and still lose. You might reach the target you set, only to discover you aimed far too low.
CEOs face a similar risk. We spend enormous energy asking whether teams are performing and plans are being executed. Those questions matter, but they come after a harder one: Have we correctly understood what is possible?
A CEO’s highest-leverage contribution is setting the right ambition. That requires three judgments.
1. Identify the few decisions that actually change the game
CEOs don’t create value by making the most decisions. If an organization works properly, people make thousands of decisions about products, customers and operations every day. The CEO’s disproportionate value often comes from a few choices that determine where all that execution is directed.
I faced one within my first few months at Bluebeam. There was pressure to move more aggressively from 2D into 3D. Newer technologies were attracting attention, and it was reasonable to ask whether our established approach would remain relevant. I had to decide without anything close to perfect information.
I had customer conversations, research, and pattern recognition from other industries, where technologies sometimes remain valuable long after people predict their replacement. I came to believe 2D was not a declining market we needed to escape. It was a growing market where Bluebeam already had a significant advantage.
We made two deliberate choices: stay focused on 2D rather than aggressively pursue 3D, and resist becoming a broader platform company. That simplified our strategy and freed resources to invest in what we did well. We chose where our innovation could matter most.
The results reinforced our conviction. When we made that decision in September 2023, Bluebeam had more than 3 million users worldwide. By the fourth quarter of 2025, that number had reached 4 million. Bluebeam also experienced approximately 45% new-user growth from 2024 to 2026.
No single decision explains a company’s growth, and user counts alone don’t show what caused it. But the results strengthened my belief that focusing on a proven strength could be more valuable than chasing an adjacent opportunity simply because it was attracting attention.
I knew the decision carried real risk. Had I misread the market, we might have directed the organization away from its future. But that is exactly where CEOs have to add value: choosing among plausible paths when information is incomplete and waiting for certainty has a cost of its own.
Organizations naturally gravitate toward visible problems: a struggling product, a weak geography, a missed target. The most visible problem, though, is not always the largest opportunity. Sometimes the best allocation of leadership attention is to contain a weakness and put disproportionate resources behind a strength.
2. Decide what the conditions actually support
When I joined Bluebeam, I had to determine not simply whether the company was performing well, but what it could become. Those are different questions.
I looked at the market, product, team, and broader environment and believed the company had more potential than we were asking of it. The cricket analogy I used internally was simple: We were playing as though we were on a 200-run pitch. I believed it was a 400-run pitch.
So we raised the ambition. Importantly, much of the same team began performing against a higher bar. That experience reinforced a mistake leaders can make: confusing limited ambition with limited capability.
Leaders’ instinct is often to change the people, rewrite the strategy, or reorganize. Sometimes that is necessary. But a company can hit its plan and still underperform its opportunity.
“Think bigger” is not a strategy. Ambition must be grounded in what the market, product, and organization can support. Sometimes the right diagnosis requires lowering expectations. Other times, the greater failure is asking too little of a capable team.
3. Know what would prove your diagnosis wrong
Experience makes those calls possible. Over time, leaders build a library of patterns from markets that turned, products that succeeded, and strategies that failed. But experience can also become a trap. You begin seeing the same pattern everywhere.
I try to treat pattern recognition as a hypothesis, not a verdict. The question is not only why I believe I am right, but what evidence would change my mind.
When we made the 2D decision, I knew which signals to watch. If customer conversations shifted decisively toward other needs, or sales and revenue failed to respond, we would need to reconsider our judgment.
But once a strategy has been funded, presented to a board and communicated to employees, reversing course becomes psychologically expensive. Leaders can end up defending the plan rather than testing its assumptions.
The answer is not to react to every new data point. Constantly changing direction makes sustained execution impossible. It is to distinguish noise from evidence, and conviction from stubbornness.
Execution starts with diagnosis
Cricket taught me that before deciding how aggressively to play, you must understand the game in front of you. Business leadership is much the same.
Before concluding a team is underperforming, ask whether the objective is right. Before fixing the most obvious weakness, ask whether a bigger opportunity deserves your attention. And before celebrating that the company hit its plan, ask whether the plan captured the opportunity in the first place.
Sometimes the most consequential thing a CEO can do is see the same company and the same market everyone else sees — and recognize that they are playing a 200-run game on a 400-run pitch.
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