Great leaders make bold moves

The power of putting yourself out there on a daily basis

Photo by Kyle Kesterson

Here’s a quick idea I want to share: Boldness is one of the greatest areas of untapped potential for most leaders. 

The question every leader should be asking themselves is this: How many uncomfortable, bold moves are you making daily?

Bold moves, in my observation, are highly correlated with how successful you are as a leader. 

What exactly is a bold move? Let’s break it down. 

A bold move is an action that requires you to put yourself out there in ways that most people would find uncomfortable—doing the thing that the average person wouldn’t want to do. Maybe you’re asking for opportunities that most people would shy away from asking for. Or perhaps you need to voice an unpopular opinion or deliver negative feedback. Whatever the situation, you’re edging into discomfort and risking failure and rejection for the greater good of your company, your mission, and ultimately yourself. 

Bold moves might also look like: 

• Saying the hard thing

• Taking a big shot

• Proposing a collaboration 

• Making a strong request 

• Negotiating hard 

• Going for it, even if you’re feeling unsure  

• Taking an action that pushes you past your edge 

This applies to situations both within and outside your company. Let’s play out some scenarios: A bold move in business could be asking for a sale. Putting pleasantries aside and asking for a potential partner to join forces with you. Going to the press and sharing something bold. Asking for something big in a negotiation. Firing someone who hasn’t been performing. Sharing feedback that is difficult to deliver to a teammate who needs to know that information.

Why should you be doing this on a daily basis?

A true leader is someone who’s able to embrace discomfort. As the leader of a company, your business directly benefits from the number of uncomfortable, bold moves you make. Sometimes you’ll fall flat, other times you’ll win big—that’s why the frequency matters here. If you’re only making a couple of bold moves each month or year, you will lose out to someone who isn’t afraid to pick up the phone whenever needed and ask for something big. If they’re met with rejection, they know it’s just part of the process. They get up the next day and make another bold move. 

We humans are wired to seek out comfort, so we find all kinds of ways to avoid taking risks, being vulnerable, and rocking the boat. This makes it harder and harder over time to make those kinds of moves, and to do it well. Getting comfortable with discomfort is a muscle to be flexed with daily repetition. The more comfortable we can become in pushing past our limits, the more we (and our businesses) grow. 

For any leader or high performer, working hard is a given. But working hard is not enough. Working hard isn’t an edge. Can you work hard and make bold moves consistently? That’s the juice. That’s the edge. That’s how you make the quantum leap from where you are now to where you want to be. 

Bold moves unlock major progress. They provide the potential for game changers to happen to you and your business. As it’s often said, you take the first big step and the universe will take a thousand steps to meet you. This is how we unlock serendipity, magical occurrences, and what most people call “luck.” 

I met my wife because I made the uncomfortable, bold move of walking up to her and striking up a conversation, risking rejection and humiliation. I landed a million-dollar investment in my first business because I asked my dad to connect me to some of his friends, there was a ton of awkwardness and a risk of embarrassment. I helped raise over $10B for charity because many times a day for several years I dared to ask very successful entrepreneurs to commit to giving some of their equity to charity if they sold their company.

Take an inventory of your history and habits around bold action. What’s your relationship with discomfort? How often are you making bold moves? What bold moves have you made in the past that have served your growth?