Inside Out Leadership

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Effortless Leadership

Welcome Entrepreneurs, I'm so glad you're here.

Before we dive in, here's a link to last week's tactical issue on the single reframe that creates the most leverage in a scaling company, in case you missed it.

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.

It was a blast to write, and I hope you enjoy reading it (and that maybe it even makes you reflect on your own process).

“Great leaders don’t see themselves as great. They see themselves as human.” – Simon Sinek

“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?”


Things I read this week

One: FEAR, the startup serial killer who must not be named (I-O)

"It’s uncomfortable, but we need to begin to talk about fear as an industry, openly and without stigma. We need to treat it as a business risk to be managed, rather than a weakness to be shunned. “Ignoring it and hoping it goes away” is not an acceptable strategy for competition or technical debt, nor should it be for fear."

LINK >>

Two: How to get the most out of coaching (Brian Wang) 

A friend of mine (former operator turned coach) shows here how to get the most out of an engagement with an executive coach. If you haven't worked with a coach before, highly recommend reading before taking the plunge.

LINK >>

Three: The role of debate in buddhism (Youtube)

One of my favorite aspects of the Buddhist tradition is the role of debate, which you can see in action at the link below. Distinct from western debate, the goal here isn't to win. The goal is to challenge your partner to go deeper, and (very cool) to keep smiling throughout.
LINK >>

Four: The Cognitive dissonance of the CEO (Ed Batista)

The CEO job requires someone to be at once optimistic and compelling about the inevitability of a desired future (to recruit and raise money), while also being realistic and open about the risks and all the shit that can go wrong (to operate). This dissonance is stressful, and is captured well here.

LINK >>

Five: How spiritual health fosters human resilience (McKinsey)

Now that we know what to look for, we're seeing science pointing the way to spirituality all the time. Even in McKinsey! This piece juxtaposes the rigidity of "achiever's mindset" with the flexibility and resilience of spirituality. If the S word still has four letters to you, you're only limiting yourself. 

LINK >>


Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:


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 supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. 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.