Team leadership for introverts


Hi Reader,

As a natural introvert, I was someone who went to conferences and talked to no one.

So it’s kind of crazy that now I regularly speak on stage in front of large audiences.

Sometimes, that audience is my own company.

This week, I’m on a team retreat with most of our 83-person team.

At ConvertKit (soon to be Kit), we host two annual retreats every year. It’s an important part of our company culture, especially as a fully remote team.

I was thinking back to our first retreat in 2016 when we had just 21 team members.

We were all sitting around a giant living room in a cabin, and I thought, “Wow, it's so great that we're all here together! Someone should probably kick this thing off…”

Then I realized that person was me.

That’s the moment I realized I’m no longer just a coder or designer behind the scenes. I actually need to lead.

I wasn’t born knowing how to be an effective leader.

There’s a common idea that leaders are extroverts; they’re charismatic, energetic, and leadership just comes naturally to them.

But introverts can be leaders too. Some of the greatest ones are.

Whether you’re introverted or extroverted, it doesn’t matter. Nobody is born a leader. It’s a skill anyone can develop.

A big part of building the skill of leadership is simply having courage, because you have to be willing to make mistakes. Expect it to feel unnatural at first.

I still make dumb mistakes, but I remind myself: I led the company to this point and a lot of brilliant people trust me to take us to the next level.

While mistakes are inevitable, I also try to learn as much as possible from those who have done it before.

In addition to learning from peers and books, I also invest in leadership development in the form of executive coaching—not only for me but for everyone on the leadership team.

We work with a company called Reboot, and they have some incredible coaches. One of the things they like to say that has stuck with me is, “Take your seat as the leader.”

Something they observed early on is I was so keen on listening to everyone in an attempt to make them all feel heard, I would end up making a collective decision that actually left everyone feeling unsettled.

I had this idea in my head that if I made a decision counter to what another executive or leader in the company said, that it meant I didn’t hear them. Which, of course, is not only untrue but also not good leadership.

One of many things I had to learn was to embrace my role as CEO and decision maker; making sure to listen to those with key input but ultimately, taking my seat as the leader.

Being a leader is exciting, challenging, and definitely stressful at times. But I wouldn’t change it for anything.

If you’re introverted, you absolutely can run a company, and you can be a great leader. Your ability to thoughtfully reflect can be a major advantage. Everyone has things to work on and weaknesses to improve.

But you do have what it takes. You can do it if you want to.

All you need is a willingness to step up.


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5 Best Strategies to Scale Creator Products FAST | Startup Investor Reveals

This week, I spoke with John Durant, the founder of Wild Ventures and a prolific investor in the health and wellness space.

John led seed investments into top consumer startups, such as Thrive Market, Primal Kitchen, Magic Spoon, LMNT, and more. These are many companies that I talk about in my Billion Dollar Creator content.

In this episode, he shares:

  • A crucial step for founders when building a team
  • Proven strategies to take your niche brand mainstream
  • Key mistakes to avoid when launching creator-led products

Tune in to hear us discuss common pitfalls that both struggling and successful companies encounter and strategies for scaling a business from a niche audience to a mass-market brand.

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27-year-old Isaac French shares how he built Live Oak Lake—a resort with seven luxury cabins in the heart of Texas. In just the first year, they did $1M in bookings, netting nearly $600K with 80%+ direct booking rates.

There’s a lot that goes into finding the right location, understanding real estate finance, and streamlining operations and bookings…

But the biggest factor in Isaac's success? It all comes down to storytelling.

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Have a great week!

—Nathan

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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