The Paradox of Certainty

In the realm of leadership, the pressure to appear infallible can be daunting. But if we’re honest with ourselves, how often are we sure that every decision is the right one?

Leaders face relentless pressure to project certainty. Yet, despite the rewards of appearing sure, this doesn't always translate into effective leadership.

In my 40 years of navigating tough challenges in my career, I've learned that one of the most powerful phrases a leader can utter is:  "I don't know." This simple admission can unlock the potential for growth, innovation, and collaboration.

Saying “I don’t know” has never been easy for me. There were many times in my career that those three words ought to have been my response, but the pressure to deliver certainty prevented me from having the courage to say it. 

Yet, some of the best work I’ve ever done in my life almost always included acknowledging my own limitations so that the gifts of others could help solve the problem at hand. When leaders admit "I don't know," they can shed their "heavy armor," leading to deeper trust and better decision-making.

My Own Leap into the Unknown

Co-founding Civilla marked a significant shift from my role as CEO of a stable, 150-year-old nonprofit. This leap was driven by a shared belief that meaningful change was possible in addressing complex social issues. As I embarked on this journey with the Civilla team, I found myself in unfamiliar territory, facing challenges I had never encountered before.

I quickly realized there was much I didn't know:

• How to build an organization from the ground up
• How to effectively collaborate with co-founders in this new venture
• How to drive large-scale change with a small, dedicated team

These unknowns were daunting, but they also became opportunities for growth. By realizing my limitations, I opened myself up to learning from others and discovering new approaches. 

For instance, when it came to partnering with co-founders, I had to set aside my previous experiences as a CEO. Instead of assuming I had the answers from my previous role, I focused on helping build an environment where everyone could contribute to the strategic direction of Civilla. By doing so, we fostered a culture where leadership responsibilities were shared, and innovative ideas could flourish from all corners of our organization. This approach not only led to more robust decision-making and aligned project work, but also allowed each team member to grow as leaders.

These experiences at Civilla reinforced my belief in the power of admitting uncertainty, a perspective that would prove to be important throughout the years.

The Impact of Embracing Uncertainty in Leadership

There are many examples that highlight the importance of this perspective. Consider these scenarios:

• LEGO's Near-Bankruptcy Turnaround: When LEGO was near bankruptcy in 2004, new CEO Jørgen Vig Knudstorp admitted he didn't know how to save the company. This led to extensive customer research and a successful refocus on LEGO's core product. Today, Lego is over a $65 Billion company.
• Pixar's "Braintrust": Pixar's leadership established a culture where it's okay to say "I don't know how to fix this story problem." This led to the creation of their "Braintrust" meetings, where frank discussions about story issues have resulted in numerous successful animated films including Toy Story, Ratatouille, and the Incredibles. 
• Google's 20% Time: Google's policy of allowing engineers to spend 20% of their time on personal projects stemmed from leadership admitting they didn't know where the next big innovation would come from. This led to the creation of Gmail, Google Maps, and AdSense.

These examples show that it’s important for leaders to strike a delicate balance between admitting uncertainty and maintaining confidence and direction. This skill is rarely taught but rather learned through experience. Whether you’re launching a new organization or leading a mission-critical initiative, knowing when to say "I don't know" can benefit everyone involved. It creates space for collaborative problem-solving and fosters a culture of openness and continuous learning.

Methods to Explore the Unknown

I have learned that leadership isn’t about having all the answers—it’s about cultivating curiosity and seeking the perspectives of others. Leaders who actively embrace uncertainty and garner the wisdom of others not only empower themselves but also set a powerful example for others.

Below are some methods that leaders can consider to help guide them through uncertainty and into effective problem-solving. 

• Become a Student: Adopting a beginner’s mindset helps keep our certainty in check and opens the door to curiosity. Leaders benefit from remembering what it feels like to be on something new. Why? Because it keeps us humble and encourages us to ask better questions. This openness allows leaders to loosen their grip while creating space for others to share their insights and talents. In the end, this mindset leads to even stronger solutions. 
• Ask a Follow Up Question: Saying “I don’t know” is a start, but it isn’t enough on its own. I have discovered that asking a simple follow-up question is a strong path to better answers – “I don’t know AND what do you think?” Challenge yourself to ask an “and” question that could lead down a new path of clarity.
• Explore a Prototype: The fastest, quickest, and cheapest way to learn is to follow your curiosity. Act on it, even when unsure. Prototyping a hunch will help a leader learn by testing, piloting the idea, and assessing results to gain more clarity around a decision before going for a full launch. 
• Stay Close to the End User: Leaders often become disconnected from the core issues they need to address. The key to finding effective solutions lies with the end user, the person closest to the issue, who is frequently the most overlooked expert. By prioritizing their insights, leaders can gain important perspectives that drive meaningful progress. Engaging with and listening to end users not only enhances understanding but also leads to more effective and durable results. After all, they are the ones who truly know the most important challenges that need to be addressed.

A Call to Action

Leaders often possess powerful visions that move the world forward. But executing these visions is never a solo endeavor. I strive to challenge myself to have the courage to admit when I have reached my own limits of expertise and understanding. I know I am at my best when I remain open to discovering new ways of knowing. Perhaps this approach could help you too.

Sometimes, you have nothing to lose by saying “I don’t know”. And sometimes, you have everything to lose by pretending otherwise. Consider this your permission slip to say: “I don’t know, what do you think?”

- Michael J. Brennan