Effortless Leadership
“Great leaders don’t see themselves as great. They see themselves as human.” – Simon Sinek
This week's issue is centered around a fun story about the process of becoming a leader.
People so often think of leadership development as a matter of working ever harder to adhere to an idealized vision of leadership with increasing precision. But in my experience, and in that of the great leaders I know and have worked with, it's actually the exact opposite.
“I want to grow into the best leader I can be.” The founder oozed ambition and conviction.
“Fantastic,” I replied. “What makes a good leader, to you?”
I could see him considering. Leadership, I’ve learned, is a word founders often throw around without really understanding what it means.
“There are a few things,” he said. He rattled off 14 different characteristics—Honesty, openness, determination, so on and so forth. He was on such a roll I let him continue, taking notes.
“This is an outstanding list,” I remarked after he’d finished. “Now, try on what it might feel like to embody these characteristics for a moment.” I read the list back to him. “How does it feel?”
“Honestly, a little daunting,” he said. He looked a bit overwhelmed. “It’s exciting, because I want to get there, but it feels like I have so far to go.”
“That makes sense,” I said. “Based on your list, I feel like I have some work to do, too.”
I paused. I had the beginnings of where I wanted to go next, but I’ve learned over time the value of allowing time for my thoughts to take shape.
“I wonder how you’ll know that you’ve become a great leader?” I finally asked. “At what point will you check the box on all these characteristics and get your leader badge?”
He paused. “I don’t know,” he said at last. “I don’t know that you ever would.”
I noticed him distance himself from the question by shifting to the second person, but decided to let it go.
“That’s how it seems to me,” I agreed. “It seems like each of these characteristics exist on a spectrum. At any time you could be doing well or poorly, but it doesn’t mean much if you kick ass at integrity for a year, only to fall off the wagon right after.”
“Yeah,” he looked disappointed. “But then if it’s not working my ass off to embody these characteristics, what makes a great leader?”
“I don’t know,” I replied. “That’s up to you. It’s your company, and your life.”
We sat together golden silence. These are some of my favorite moments in coaching, when clients (and I!) turn their attention inward, with curiosity and respect for the treasures they might find within. I consider myself so lucky to accompany people on this beginning of beginnings.
“I was just thinking about my old boss,” he said at last. “He exhibits most of these characteristics, but he doesn’t work hard at it. He just seems like he’s having the time of his life all the time. It doesn’t even seem like he thinks about these things.”
I sensed he was working something out and remained silent.
“He just is that way,” he continued. “Naturally. It doesn’t seem like he tries to be like anything.”
“I’ve noticed that myself in great leaders,” I said. “They don’t typically seem to be working all that hard.”
“It’s like he is all these things, or some of them, but not because he’s trying. Just because he knows who he is, and it comes from there. He is a leader. He doesn’t do leadership.”
We sat with the realization, among the most important for a young leader. I thought of own path, balancing, petrified, along the narrow road of expectation for so many years, before I finally mustered up the courage to touch that place deep inside myself that feels called. The day when I first gave myself the infinite gift of inner curiosity.
“Should we revise our list?” I prompted.
“Yeah. I think a great leader is himself. The other stuff comes or it doesn’t. But he knows who he is, and he just is that person no matter what.”
“That sounds right to me,” I said, writing down his words in our shared journal. “It does beg a question, though.”
“Sure does,” he laughed. “Who the fuck am I?”
“Let’s find out, shall we?”
Want to dive deeper?
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Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.
Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.
I coach leaders how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
To learn more about working with me, click here.