Leadership: The Secret Existential Crisis Entrepreneurs Never Talk About

At some point in your journey as an entrepreneur, if you’re lucky, you’re going to face an existential crisis. It’s something few of us talk about but many of us have faced. But if you know it’s coming and you’re prepared, you can get through it with as little pain as possible.

You see . . .

When you start a business or side hustle your work is about two things
Doing great work and/or providing a valuable service or product
Finding customers and helping them understand the value of what you have to offer

These two things are not small, easy, or simple to figure out, but they are at least straightforward. Your work needs to be good and you need customers who see that…

But as you grow and get more customers, offer more complex services, and start to hire people to support you or do some of the work for you, your role begins to change.

You go from being a person who does great work to being a person who creates great work.

And this transition is challenging. Doing great work is simple, you sit down and do your best. Creating great work is more complicated, you are planning, leading, and assuring that great work is getting done.

The skills are different, the former is about keeping track and executing. The latter is about defining and communicating what is good, and then making sure “good” is happening.

I remember when I worked as a house manager at a music venue and the boss asked me to come downstairs. “What’s wrong with this picture?” I looked and everything looked fine to me. “It’s too bright in here,” she clapped back in my silence. “Oh?”

“How dark should it be?” She groaned and lowered the lights. “I can’t tell you everything, you’re just going to have to figure it out.”

I felt discouraged. What she was saying was somewhat helpful. Most places lower the lights at a certain time of night. It increases the vibe, encourages people to buy drinks, and makes it feel less harsh when you come in from the night. But it’s not something I had ever thought about before.

It was good she wanted to teach me, but this was the WORST way to do it. Instead of helping me learn and giving me some guidelines, she just got mad at me. What was OBVIOUS to her was NOT obvious to me.

This is essentially a failure in leadership and it’s something I see founders, entrepreneurs, and owners do ALL the time with new team members.

It all starts with What Can’t They Just!

Often when I listen to founders and entrepreneurs complain about their team members at some point they’ll say Why Can’t They Just . . .
Send me the updates I need
Answer this email
Make a decision on their own

The underlying assumption is that other people SHOULD think like you think. They should be capable, they should be leaders, and they should know what you know and act how you act.

But if your team simply duplicates your skill then
You need more skills
You’re not hiring the right people

The best people bring new ideas and talents to the table. The best people approach problems differently. The best people create things but not the way you will.

The hard thing for most leaders is that they don’t understand how to get good work out of people who are different from them.

So they expect what they would produce and then get upset when they don’t get it.

Next Level Leadership

This isn’t really leadership it’s cloning.
So if you want to be a better leader you’re going to have to let go of this strategy.

The question you should ask yourself is how do I get the best work out of the people I have?
NOT how do I get them to think like me?

The reason why this is so hard for most leaders is that it requires a shift in identity.

You start with the identity of I’M GREAT AT DOING THIS
to I MAKE OTHER PEOPLE GREAT AT DOING THIS

And that shift in identity is hard.

It’s why so many founders end up writing code, getting on sales calls, or micro-managing people on their team.

They don’t trust what other people do and they are unwilling to let anyone else be better than they are.

So as you grow your business get ready for this.

At some point, YOU’LL HAVE TO LET GO OF ALMOST EVERYTHING THAT MADE YOU FEEL CONFIDENT IN YOURSELF WHEN YOU GOT STARTED.

It’s a key initiation as a leader. And a threshold you need to cross if you want to truly become a great leader.