
Why “I don’t know” may be one of the most consequential expressions of executive judgment
Several years ago, I interviewed former WD-40 Company CEO Garry Ridge on the Get Hired Up podcast.
Garry and I had met previously in San Diego, and by the time he joined me on the podcast, I was already familiar with his philosophy of leadership, accountability and organizational culture.
But one of the simplest things he said during our conversation has stayed with me. Reflecting on becoming CEO, Garry described realizing that there were things he simply didn’t know.
Eventually, he became comfortable saying three words:
“I don’t know.”
That may sound unremarkable. For a senior executive, it isn’t.
The further someone progresses in leadership, the more people expect answers. Employees look for direction. Boards expect command of the business. Investors test assumptions. Executive teams bring increasingly complicated problems to the CEO.
And somewhere along the way, experience can create a subtle pressure to know. But perhaps one of the most important forms of executive judgment is knowing when you don’t.
The boardroom question nobody wanted to ask
Garry illustrated the point with a terrific story. He was sitting in a boardroom listening to a consultant deliver a presentation he couldn’t understand. He looked around the room and sensed that others might be struggling with it as well. So he raised his hand.
He essentially said: I have no idea what you’re talking about.
The reaction around the room confirmed his suspicion. Other people hadn’t understood either. When Garry told me the story, I remember thinking that what he was describing wasn’t incompetence at all. It was confidence.
There is a significant difference between not knowing something and being unable to acknowledge that you don’t know it. The first is inevitable. The second can become dangerous.
Experience can create its own blind spot
Senior leaders rarely arrive in consequential roles accidentally. They have accumulated experience, pattern recognition, technical knowledge, relationships and judgment over many years, and that experience matters. But it can also create an interesting leadership paradox, because the more accomplished someone becomes, the more expensive it can feel to reveal uncertainty.
A newly appointed CEO may hesitate to tell the board that she doesn’t yet understand an issue. A founder may continue relying on assumptions that helped build the company even though the market has changed. An executive considering a major career move may believe that decades of experience should make the answer obvious.
A board director may remain silent rather than ask the question everyone else appears to understand. And a leader surrounded by experts may confuse access to expertise with personal understanding. In each situation, the problem isn’t the absence of knowledge, but rather it’s the possibility that the leader will make a consequential decision without recognizing what remains unknown.
“I don’t know” is only the beginning
Of course, uncertainty isn’t a leadership strategy. A CEO cannot respond to every difficult question with a shrug and celebrate intellectual humility. The value of I don’t know is what happens next.
- What do I need to understand?
- Who knows more about this than I do?
- What assumptions are we making?
- What evidence would change my mind?
- What happens if we’re wrong?
- Who in this room sees the problem differently?
These are not signs that judgment has been suspended, but rather they are how judgment becomes more rigorous. And they become especially important when the executive is operating in unfamiliar territory.
When the role gets bigger
One of the recurring patterns in our work at Westgate involves senior leaders whose careers have expanded beyond the environments in which they originally developed their expertise.
- A functional executive becomes an enterprise leader.
- An executive becomes a CEO.
- A founder becomes an investor.
- An operator joins a fiduciary board.
- A CEO begins working with a new board.
An owner approaches an exit and discovers that questions about wealth, succession, family and identity now sit alongside questions about the business. The résumé may be exceptional. But the decision environment has changed, and the knowledge that produced success in one context doesn’t automatically answer the questions presented by the next.
This is where experience must sometimes give way to curiosity. Not because experience has become irrelevant. Because the stakes have changed.
Values can reduce the burden of knowing
There was another part of my conversation with Garry that I appreciate even more today. At WD-40 Company, Garry described values not as words displayed on a wall, but as a decision-making system. And, people throughout the organization were empowered to make decisions provided they used the company’s values as their guiding framework.
He gave examples of employees deciding whether a meeting warranted travelling in person or whether participating virtually would accomplish the objective. Rather than requiring the CEO to make every judgment, the organization’s values helped people make those judgments themselves.
That distinction is important, because strong leadership isn’t demonstrated by becoming the person who possesses every answer. Sometimes it is demonstrated by building an environment in which good decisions don’t require your answer. That is a very different conception of authority.
The CEO as learner
Garry’s own career illustrates it beautifully. When he was offered the opportunity to lead WD-40 Company, he didn’t respond by assuming that his previous success had prepared him for everything the position would require. He went back to school. He studied executive leadership at the University of San Diego, where he met Ken Blanchard. Their relationship eventually led to teaching, collaboration and their book Helping People Win at Work. Garry went on to build a leadership philosophy around helping people succeed rather than simply evaluating whether they had.
There is something instructive about that progression.
Responsibility increased; therefore, therefore learning increased. It could easily have gone the other way.
Responsibility increased; therefore certainty increased.
Those are very different leadership trajectories.
The questions become harder near the top
As careers progress, the questions confronting leaders often become less technically answerable.
- Should we replace a CEO?
- Should I accept this board seat?
- Is this the right successor?
- Should I sell the company?
- Can I trust this investor?
- Is the problem our strategy or our leadership?
- Should I remain in this role for another three years?
- What responsibility do I have when I believe the board is getting something wrong?
These aren’t questions answered simply by accumulating more information. They require judgment. And judgment becomes particularly important when information is incomplete, authority is constrained, interests diverge or the consequences of being wrong are significant.
That is increasingly where our work at Westgate is situated. We advise senior leaders navigating consequential career and leadership transitions. Frequently, the executive doesn’t need another person pretending to know the answer either. The more valuable work begins by identifying what decision is actually being made, what is known, what remains uncertain, and what assumptions may be distorting the view. Sometimes the most important discovery is that the question itself has been wrong.
Confidence without arrogance

Garry used a wonderful phrase when introducing himself during our conversation. He described himself as: “consciously incompetent, probably wrong and roughly right.” It was funny, but underneath the humor was a sophisticated leadership principle. The objective isn’t to diminish expertise or become chronically uncertain. It is to develop enough confidence that your identity no longer depends upon always being right.
- It builds capacity.
- It makes room for advisors.
- It makes room for the director who sees something differently.
- It makes room for the employee who possesses information the CEO doesn’t.
And it makes room for the possibility that the evidence has changed. In other words, “I don’t know” can create the conditions for better knowing.
Seven years later
My own relationship with Garry contains a small piece of Westgate history. I first met him in San Diego in March 2019. He had generously given me access to his corporate rate at the Westgate Hotel, where I stayed during the trip. At the time, I was wrestling with questions about the future of my own firm.
That experience stayed with me. About a year later, when the business was rebranded, Westgate became its name. I eventually told Garry the story when we recorded our podcast together.
Today, Westgate is evolving again. Our work is moving more deeply into career governance and leadership transition advisory, and I’ve found myself returning to some of the questions Garry and I discussed years ago.
- What does responsible leadership require?
- How should accomplished people make decisions when the answer isn’t obvious?
- What happens when the role changes but the person must continue evolving?
- And how do leaders create environments in which other people can exercise sound judgment too?
Perhaps that is why his three words have stayed with me. As leaders accumulate experience, the temptation may be to become increasingly certain. Executive judgment asks something harder.
Know what you know. Know what you don’t. And know the difference.
Author’s note
This article was inspired by my conversation with Garry Ridge on Get Hired Up and by the leadership example he has shared throughout his career. Garry is the former Chairman and CEO of WD-40 Company, co-author with Ken Blanchard of Helping People Win at Work, and an executive coach, teacher and speaker.
