4 Leadership Strategies of Great CEOs

As a CEO of a large organization that has grown quickly (from zero to $200 million+), I have a lot of POVs on leadership strategies that lead to strong internal culture and business results.

Here are a few concepts that I don’t see too many others talking about:

1. Look out for the “iceberg”

I stood in front of my entire company last September and rolled out a new vision for how we’re going to service clients, and 98% of them thought I was out of my mind. They didn’t believe in what I was saying at all.

Some of them thought I was like the “crazy founder” who has wild ideas on marketing opportunities that can’t actually be implemented in reality.

But I wasn’t upset about it. The truth is, if you have full, 100% buy-in from your employees, you’re in a dangerous spot.

There should be some sort of friction between a CEO or founder who sees everything that’s ahead and the people who are in the trenches. They both have different mindsets, experiences, and factors to take into account in their day-to-day.

The best analogy I can give is looking out for an iceberg.

As the captain of the ship, I’m at the top watching for icebergs and letting everyone know what we should do to avoid them. But if my employees are downstairs, they’re not seeing the same thing I see and they might disagree.

Leaders need to understand what’s happening next. Employees execute on the current and overvalue the past.

That’s something that should be expected. If you’re a leader, it’s your job to communicate.

2. Understand you’re a parent, not a babysitter

This is a huge difference between great CEOs and ones that aren’t. Great CEOs understand that they’re a parent, bad CEOs think they’re babysitters.

For example, I let people in my company do their thing. I don’t micromanage. I’m just watching and supporting as time goes on. 

With my management style, my biggest vulnerability is creating entitlement. In other words, my ability to create top-line revenue and fix problems can sometimes give leaders within my company a false sense that they’re the ones executing and getting results within their departments.

As a “parent”, I always think a lot about giving people room to try, fail, and learn – but at the same time, helping them be capable of executing at high levels on their own so that they can still win without me.    

Great CEOs sometimes seek out difficult situations and make decisions that the organization isn’t ready for. They might even make decisions that they themselves aren’t ready for.

If you’re a leader, it’s your job to make those moves that you know are right for the company in the macro, even if it causes some tension with executives or team members in the micro.

3. Make your employees feel safe

This is the number one thing I try to do as a leader. I try to make people feel safe around me.

Safety helps create speed in business for a couple of reasons:

First, when people aren’t spending time thinking how to navigate a situation, they’re spending time executing. When they’re executing, the entire machine moves faster and produces higher output.

Second, people are able to get to the punchline much faster than they otherwise would which helps me save time.

For example, there are a lot of meetings I sit in that I know are just  “disguises” for an ask or a sale on the back end. When I feel that’s the case, I immediately try to make the other person feel comfortable asking me for what they want right away.

I don’t need people to spend 45 minutes on a “set up” for a sale – I need them to be honest about the expectations they have of me.

It’s on me to create a safe environment where they feel comfortable sharing their intentions up front.

4. Understand that you work for your employees, they don’t work for you

This one is hard for a lot of leaders to understand.

Most new managers think that becoming a manager is the “graduation.” Truth is, it’s the reverse.

Leaders work for their employees.

That means you have to understand what your employees want at a deep level. You have to be constantly adapting to their needs and what they want from the organization.

For example, one of my employees might want higher pay when he’s 24. But maybe he falls in love at 28 and decides he wants to spend more time with his family. Another might be more interested in a fancy title. Another might want to get access to me and build a relationship.

Another might want to go to one of our international offices and work there.

There are a million different variables, and it’s on you as a leader to adjust to reality as it changes.

When you go from being someone who “executes” to someone who’s managing a team, you go from trading on IQ to trading on EQ. You go from doing the actual work to listening to employees, catering to what they want, taking blame, and being the bigger person.

The best managers are actually the best mentors.

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