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Why Every Entrepreneur Needs to Rethink ‘Leadership’

Why Every Entrepreneur Needs to Rethink ‘Leadership’

I need to get something off my chest.
It’s something I have been feeling for a decade. Something I would try to articulate to others but they would just reframe or dismiss it. Something that goes against what is so ingrained and celebrated in our culture that it’s almost blasphemous.

I hate leadership.

I hate it. I hate hearing about it. I hated being told to be a leader growing up. I am the CEO of a company and I still don’t want to be a leader.

Now, I’m not saying that we never need leaders. Maybe if you adjusted the definition, I could get on board with it. There are times when all of us who want to accomplish something with our lives or ideas will need to exhibit leadership. But I think we need a different mindset that will help us better solve the problems that lie ahead in the 21st century.

We don’t need more leaders. We need more designers.

Leader Vs. Designer Mindset

“Your thoughts construct patterns like scaffolding in your mind. You are really etching chemical patterns. In most cases, people get stuck in those patterns, just like grooves in a record, and they never get out of them.” – Steve Jobs

While this is not true of all leaders, I think there are some patterns and mindsets that have developed over time around the world “leader” that need to be challenged by the designer mindset.

“Leader Mindset”


No matter how many words we attach to leadership like “Servant Leadership” or “Team Leadership,” leadership seems to always naturally gravitate toward hierarchy. Author of “Mapping Innovation,” Greg Satell, says that, “Today, we are undergoing a transformation every bit as dramatic, a shift from hierarchies, strategies and tactics to networks, platforms and movements.”


Americans love them some certainty. We like leaders who are bold, tell us the “right” answers and have a black-and-white view of solutions. But the world is becoming less and less predictable and certainty is becoming more and more of a pipe dream. Rationality has its limits and when it has reached them, design will be there to help by embracing both the arts and science, logic and emotion, critical thinking and intuition.


Most “good” leaders really can talk like there is no tomorrow. Give them a microphone and they will grace it with their words. Extroversion is so imbedded in what we expect of leaders Susan Cain’s book “Quiet” calls Harvard Business the “spiritual capital of extroversion.”

“Designer Mindset”


Education expert Parker Palmer says that the best way to learn is from a “subject-centered” paradigm. This is where the subject is in the middle and each person around the subject brings their expertise, ideas and abilities to understanding it better. The “leader” in this model plays the role of facilitator synthesizing the learnings from everyone in the group.

Collaboration is not just a buzzword, it is the future of work.

Embracing the Unknown

If we really want to do anything innovative, we must first detach ourselves from certainty. Certainty is the companion of stagnation. Design understands this well. This is why iteration is so important to good design. Our brilliant co-founder (and my wife) Hillary routinely calls this “try, fail, learn.” But before we can arrive at any sense of certainty, we must first wade into the unknown, be willing to fail and pivot quickly. Design—and design thinking—is a great paradigm for embracing the unknown.


Listening takes humility and the ego is not a huge fan of humility. The design mindset is focused on listening and empathizing with the people who they are building the solution with. Leaders make things for people. No matter if you are introverted or extroverted, designers listen and build solutions with their stakeholders.

So maybe you are like me and haven’t ever really connected with leadership.

Maybe instead of trying to be a “leader,” you should consider looking to the designer’s mindsets and tools to guide how you solve challenges.

This was a freeing moment for me when I decided that I didn’t have to be a leader.

Maybe you don’t need to be a leader either. Maybe you are a designer. I think that’s a good thing, because guess what?

Leadership is dead. Designers are taking over.

This article was originally posted at Used with permission.

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