The Servant Leadership framework I fought for 20 years

Steinberg-Dietrich Hall, first floor lecture hall. I was an eager, hungry Wharton freshman. I came in with guns blazing, ready to be a Wall Street baller.

I sat in my Management 100 course, a leadership training course where we discussed the different leadership types: pacesetting, autocratic, democratic, laissez-faire… These all made sense to me.

Then came SERVANT leadership??!

It didn't compute. I wanted to run shit, not serve.

Fast forward to my own journey as a CEO. Once the company got to about 10 people, I emailed my old professor to see if she could resend me our course’s management material.

I went through them and decided that pacesetting and coaching leadership modes were more my style. Off I went with those approaches.

Servant leadership still made no sense to me.

Then, in 2018, I hit a low point. The business had a lot of success, but I was feeling as empty as ever.

As I examined my own motivations, I realized that money and status were "dirty fuel," unhealthy and unsustainable motivators. I asked Dave, my coach, "What is clean fuel?"

"I can't say for sure, Jesse, but it’s anything that gives you energy,” he replied.

“The two most common I've seen are activities that you really enjoy. And… serving others!"

There it was again.

I've talked a lot about "energies I enjoy" or "Zone of Genius," and I've spent a lot of time ensuring I keep my time in my Zone of Genius. And now I find myself in an interesting role.

I'm not the CEO of any of my businesses. Those CEOs make the decisions. My job is to influence, guide and… SERVE.

But what about service? This is a bit of a different email for me because it’s something I'm starting to unpack, versus something I already know well.

After my first meeting with Ric Elias where he tore into my financial plan, I was surprised that I felt… loved? Over dinner, I asked him about it.

He said, "Jesse, I don't care about your business results. They won't make or break me. I care about you and helping YOU level up."

I connected an important dot: As a leader, you can serve people by giving them tough feedback or "tearing into their plans" and it can still feel great for them.

If your heart is focused on helping them, that IS service.

As a leader, I was often (and still am) NOT present. I’d be on my phone, going through Slack while on a Zoom or even just thinking about my last meeting while on the current one.

Lack of presence invariably had me focus on myself and not the person I was with. It creates a selfishness that is hard to shake because if you can't be present, it’s impossible to tune into the other person.

So before you can serve, you must be present. Once you are present, you can tap into what that other person needs.

That brings me to my next learning. When I used to think of service, I thought of going to a soup kitchen or helping a nonprofit.

THEY are serving people — we are just over here being dirty capitalists. What I'm learning now is that service is a MINDSET you can bring to every interaction, every day.

I start my days by asking, "How can I serve the Universe/God?" The answer is always the same: serve each person and thing you interact with.

Well, those are my wife, my kids, a random person I walk by, all my colleagues and even my tennis opponent. I just say in my mind, "How do I serve you?"

The answer can be: tough feedback, praise and love, simply problem solving OR leaving them to solve the problem themselves.

When I'm present, everything becomes rooted in service.

I used to think generosity meant giving people money or things. And it does.

But there are SO many other ways to be generous… A helpful introduction. 5-10 minutes of a quick phone call. A brief observation. A laugh. Sharing something vulnerable. The list goes on.

One simple rule for me is: If I spot a chance to be generous, I take it.

I tip a lot. I've favorably changed deal arrangements with partners without being asked (if I thought it was generous and right). Giving was scary at first.

I was afraid I'd be taken advantage of or be a chump. But I realized that I feel better doing it and that it creates lots of trust.

I still don't fully embody it, but it’s starting to click. One important thing to point out is that it doesn't mean kowtowing to every demand of your team or business partners.

In some sense, it means quite the opposite.

I love this metaphor from the book Radical Acceptance: “Have a soft front but a firm back.” You can still share your wants and guide the ship with leadership and vision WHILE being a servant.

I'd love to hear your learnings on this and any practices that have transformed how you lead.

-jesse