Four Attributes of Successful Leaders with Jon Macaskill, Retired Navy SEAL Commander

What are some attributes that successful leaders and teams share?

Jon Macaskill is a retired Navy SEAL commander who served in the military for almost 24 years. He joins me to discuss four attributes of successful leaders he has witnessed throughout his career.

Today, Jon uses his experience and personal stories to help organizations overcome some of their day-to-day challenges. He is also the host of the ‘Men Talking Mindfulness Podcast,’ where he brings mindfulness and meditation practices to high-performing teams.

Read on to learn more about the challenges Jon had to overcome, his advice on team building, and how to recognize a confident leader.

Jon’s Background and Leadership Journey

Growing up, Jon used to spend the summers down on the Gulf Coast. He had always loved swimming, so he knew what he wanted to do after finishing high school: join the Navy Seals.

Jon got denied the first time he applied to get into the Naval Academy. However, he knew he wouldn’t give up on his dream.

He enlisted in the Navy, where he finally got picked up to go into the Naval Academy.

Jon graduated in the class of 2001 and got selected out of that group. The rest is history; Jon served in the SEAL teams from around 2003 until August of 2020.

Jon’s role changed over the years as he rose through the ranks. During this time, he got to learn valuable lessons on team-building and leadership skills.

Jon likes to compare the enlisted men on a SEAL team to the players on a football field. They’re the ones out there doing the actual work, getting the job done.

On the other hand, you can think of the officers as being the offensive and defensive coaches. These are leaders who support their team by sharing their advice and knowledge with them. But at the same time, they’re confident enough to admit they don’t have all the answers.

For Jon, the ability to admit you don’t know it all is the trademark of a true leader.

That may be one of the reasons, so many military leaders do well in corporate America. They have learned to rely on the input from those around them. Their ultimate goal is to empower their teams the best they can – pretending to know it all goes against this goal.

The Challenges of Managing in Organizations

Today, Jon is an organizational cultural consultant. His role requires him to look at an organization through a different optic than most leadership consultants.

He doesn’t look at finances or numbers at all. Jon’s primary goal is to offer solutions on improving the organization’s culture – which can sometimes be challenging.

Jon has identified two recurrent issues that are invariably detrimental to an organization: pride and toxicity.

Let’s start with pride. We’ve already discussed how essential it is for a leader to allow themselves to be vulnerable. However, it’s common to find proud leaders who think they know it all. Their lack of emotional intelligence makes them feel their way is the only way.

So, be a leader who wants to learn from their people, someone who admits when they’re wrong. Your people will want to work for you because they’ll see you as a human being rather than just a position.

Now, let’s talk about toxicity. Unfortunately, there’s much toxicity in the workplace these days. Having discussions on sensitive topics like religion and politics will only harm a company’s culture. So, Jon believes that such arguments don’t belong in the workspace.

Toxicity can also happen when you’ve got cliques forming around an organization’s different departments and divisions.

Here, Jon’s solution is to get those departments and divisions to work together. Let your team learn how other departments work. Let them get to know each other. You’ll help your team develop respect and admiration for the different departments and their people.

Having team-building exercises or team-building retreats is one of the best strategies to eliminate toxicity in an organization.

The Four Traits of Successful Leaders

In his time in the SEAL teams and the organizations he has worked with, Jon has identified four attributes successful leaders and teams share.

1. Preparedness

Preparedness is being able to plan for the foreseen and unforeseen. You need to know where you are and what you need to get where you want to go.

In the military, they say hope is not a course of action. You can’t hope your way to success. You’ve got to build your way to success.

Prepared leaders leverage their strengths to solve problems proactively. They don’t wait for issues to come up to start acting. They’re also in touch with the organization, so they are aware of potential problems that could arise.

2. Resilience

Resilience is the ability to bounce back once you get knocked down. You’re going to get knocked down; there’s no way around it.

Remember Jon’s first attempt to join the Naval Academy. While he got rejected, his determination helped him find a way to fulfill his dream.

Successful leaders don’t get discouraged when things go wrong. Instead, they view failures as lessons that will ultimately help them succeed.

3. Grit

For Jon, grit is setting goals and then working to achieve those goals.

To succeed in an organization, you need to build a high-performing team. To do that, you might have to make some hard decisions. But if you have a clear view of your goals, the process will be much easier.

For example, firing someone is a hard decision. However, hiring the wrong person will only be detrimental to an organization reaching its goals.

If you think someone will be toxic in the culture, you’ve got to cut them out. Otherwise, you’re going to be on a sinking ship.

4. Compassion

Compassion is about understanding what your people need and what you need.

Vulnerability leads to compassion. Vulnerability is a strength, but most times, fear keeps us from being vulnerable.

We’re afraid that we’ll be perceived as weak. However, not overcoming that fear – that is the weakness.

It’s essential to be vulnerable enough to know that you have a weakness and express that. Only then can you lean on somebody else who has that as a strength.

Key Takeaways

– Why Jon decided to join the Navy (02:27)
– Why military leaders do so well in the corporate world (07:53)
– The challenges of managing in organizations (11:02)
– The traits of high-performing leaders and teams (14:08)
– How to recognize a genuinely confident leader (18:19)
– Dealing with toxic team members (24:02)
– A look into Jon’s ‘Men Talking Mindfulness’ podcast (25:51)

Leadership Resources

How are the leaders at all levels of management tackling the toughest challenges each day? Learn more at: https://sartoleadershipgroup.com

About the host, Rob Fonte

Rob Fonte is the founder and President of Sarto Leadership Group, whose reputation has been built on being a transformational leader and inspirational coach with a passion for developing others. His twenty-year career spans across multiple disciplines including leading award-winning sales teams. Rob is an academically trained Executive Coach certified by The University of Texas and the International Coach Federation.