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A Tool For How To Handle Uncertainty In Leadership


When I talk about my definition of leadership, I think it sometimes catches people off guard. In my mind, leadership is not about telling others what to do or taking command of a room. Leadership is the boundary between certainty and uncertainty.

The best leadership traits are not what you might think.

For those in leadership positions, there are specific things that we know, can bet on, and are confident about. These things are certain, and we can be decisive about them. But there are also plenty of things we don’t know. These need to be researched, explored, and experimented with. They’re uncertain.

One of the best leadership traits you can have is the ability to identify what’s certain versus what’s uncertain and then communicate that to your team. Many people wrongly assume that strong leadership is about being certain in all situations. And while decisiveness is an essential leadership trait, there is a time and place for it.

There will always be uncertainty in leadership—good leaders understand this and face it head on, while bad leaders will simply brush past the uncertainty and move forward regardless. They may be acting decisively, but they’re likely going to cause problems in the future by not addressing the uncertainties in their path.

As a result, many people think that showing uncertainty in leadership is a weakness—when it’s the exact opposite.

Knowing when and how to admit your own uncertainties is one of the best leadership traits you can have. Great leaders will tell you when they’re uncertain. They lean on their teams and the experts around them to help them clarify those uncertainties and make the right decisions.

I believe that anyone who wants to become a better leader needs to shift their thinking around uncertainty and leadership. Instead of thinking about how to handle uncertainty in leadership, you need to be thinking about how to embrace uncertainty in leadership!

Possibilities are uncertain.

We’ve recently introduced a new tool to some of our Strategic Coach entrepreneurs that revolves around possibilities, but it’s also closely related to uncertainty in leadership. To make the connection, let’s consider for a moment what a “possibility” really is.

For me, possibilities are things that we keep coming back to in our minds but haven’t communicated to anyone or taken action on. They’re persistent thoughts, and they’re so important that we don’t want to mess them up by starting in the wrong way. They stay in the back of our minds because we want to act on them some day, but we delay taking action because we’re uncertain of what will happen.

Most entrepreneurs have many possibilities in the back of their mind but they don’t feel comfortable communicating them because there are so many uncertainties.

They feel like they can’t share these possibilities with anyone until they figure out how to handle them. But it’s a catch-22, because they can’t figure out how to handle them unless they get help from others!

And that’s why learning how to handle uncertainty in leadership (or embrace uncertainty in leadership) is so important. If you want to make your possibilities into reality as an entrepreneur, you need to be able to embrace uncertainty. Your team will help you gain certainty around your ideas—but only if you let them.

The tool we recently introduced has one simple purpose: to help entrepreneurs organize and communicate all of the possibilities in their minds, including all the uncertainties that come with them. Although it wasn’t intended at the time to be a leadership tool, it helps to instill one of the greatest leadership lessons you can learn: being uncertain is not a problem. It’s only a problem if you don’t voice your uncertainties.

Voicing my own uncertainties.

When my book Who Not How became a bestseller, I was thrilled. When it became an eight times bestseller, I knew this concept was going to be bigger than the book itself. The concept of Who Not How has been a game changer for entrepreneurs everywhere and for Strategic Coach as a company. It’s a leadership principle, a vehicle for expanding your capabilities, and a mindset that can help anyone build their ideal lifestyle.

Who Not How has already helped thousands of entrepreneurs discover practically endless possibilities for their lives and businesses, and I’m no exception. With the popularity of Who Not How, I saw a new possibility for Strategic Coach where this one concept could be at the center of nearly everything we do and teach. It’s already a core concept, but I want to take it a step further by incorporating it into all of our messaging, marketing, and materials.

This shift could open up many new possibilities for Strategic Coach, but it also complicates things. We already had our busiest year ever, and this type of switch would affect nearly everyone who works at Strategic Coach—from the leadership team to coaches, salespeople, Program Advisors, and more. It would involve a lot of teamwork complexity, which is not my area of expertise.

As a result, I was very uncertain about this new possibility. And like many entrepreneurs, I didn’t immediately share it with my team due to all of the uncertainties that surrounded it. But I took a dose of my own medicine and chose to share this new possibility with my leadership team and others in the Strategic Coach community.

The feedback I got has been fantastic, and although we’re still undecided about how to move forward, it’s shown me the value of embracing uncertainty in leadership.

Honesty, transparency, and uncertainty.

Learning how to handle uncertainty in leadership really comes down to being honest and transparent with yourself and your team. Entrepreneurs have a tendency to look past uncertainty and just “go for it.” But this is not a good leadership trait, and this type of thinking can destroy companies.

When you’re honest and transparent about your uncertainties as a leader, you get buy-in from your team. Instead of following orders, they’re now in a position to help you and collaborate on how to make your possibilities into a reality. They become the Whos for your Hows.

Not only does it make your job as a leader easier, but it gives purpose to your team members and it helps you turn your possibilities into realities.

About the Author

Dan Sullivan is the world’s foremost expert on entrepreneurship in action. He is the founder of The Strategic Coach Inc. and creator of The Strategic Coach® Program. Visionary, creative, wise, playful, and generous, he is a true champion of entrepreneurs worldwide.

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