1. They don’t simply copy - they think critically. 

Your rationale for doing something shouldn’t stop at “Well so-and-so did this, so we’re doing it too.”

Instead, it should be, “So and so did this, and I thought about how it’s different and similar to our situation - here’s what I discovered…and therefore I chose to do…”

Here are some common questions to help you think critically when comparing scenarios with similar companies:

• Did they have major factors, like the pandemic, that accelerated or decelerated their path towards success?

• How did their stage and funding compare to mine today? What levers could they pull on that I don’t necessarily have access to? What levers do I have access to that they don’t necessarily have?

• What are the parts of them and their company that I don’t want to emulate? Is their strategy still compatible with mine if I don’t want to emulate those things?

  • Example: Some companies are willing to pull out all stops, even going as far as borderline risky/illegal actions, to get ahead. Or, they are willing to pull shady moves to “make it to the top.” Is that a risk you’re willing to take, or someone you would like to be? Notice the question isn’t, “Do you HAVE to take that risk” - you don’t HAVE to do anything. Your job is to say yes or no - no one is holding a gun to your head to make decisions.

2. They choose their leadership counsel wisely.

There’s another founder I work with who I really like, who once told me:

In his book Think Again, Adam Grant argues everyone should have a “Challenge Network”: a group of trusted individuals who provide candid feedback to help you think and refine your ideas.

All facets of your life can have different leadership counsel. In your personal life, a parent or spouse might be a great counsel to solicit thoughts and opinions from. Your children might even be a part of this if you’re looking to add levity and playfulness.

Similarly, in building a company and being an operator, you need to have people who have your best interest at heart, and who will tell you things as they are. Coaches and advisors usually make for great people on this panel.

Lastly, your leadership counsel doesn’t even have to be people who know you personally. Thanks to advances in AI technology, there are amazing platforms like Delphi where you can talk to the best and brightest thinkers, and get their take on your unique, personal situation.

This is the first time in human history where it is possible to get curated, personalized feedback on your specific situation without actually needing to shell out the big bucks for private sessions - because a person’s time is now scalable. I can’t recommend enough engaging with these tools and learning as much as you can for your specific

3. They’re crystal-clear on their “why” through the power of introspection.

The best leaders I’ve ever met have a staggeringly high level of self-reflection and introspection. This allows them to create a solid line of thinking on what they care about, what they believe and think, and most importantly, why - without external influence.Remember: It's exponentially harder to let go of someone who is competent, likable, and consistently demonstrates growth potential.

Put simply, they recognize that there are three buckets of knowledge:

• Things I know

• Things I know that I don’t know

• Things I don’t know that I don’t know

That last bullet point scares the shit out of all highly-aware, conscious leaders. What don’t they know about themselves and their situations?

The only two solutions to solve this are:

1. Seeking the counsel of the Challenge Network

2. Practicing introspection

Outside of a Challenge Network, the most common ways I see aware, conscious leaders practice introspection are:

• Journaling - many operators I know enjoy The Artist’s Way with a daily journaling activity. They just write.

• Meditation - the practice of equanimity, or observing everything without judgment, reveals a lot about what your preferences and irks are. Equanimity combined with a deep stoic practice is a powerful combo; for those looking for a great introduction to this practice, check out Shinzen Young’s See-Hear-Feel meditation, and Massimo Pigliucci’s book Handbook for New Stoics.

• ChatGPT - ah yes, again, in a world with AI advances, ChatGPT might be one of your best introspection tools.

  If you’re anything like me, you use ChatGPT obsessively for everything from learning how to speak French and Mandarin, to studying theology intimately, to learning about real estate, and talking to it about your most personal dilemmas.

  As a result, I think ChatGPT has the opportunity to become a more knowledgeable (creepier?) version of Facebook Ads: it knows you so well, it might even know you better than your loved ones know you, based on what you ask it and what you say.

  
  To utilize ChatGPT in this way, try these kinds of prompts:

  • “ChatGPT, based on what you know about me, what are my biggest blindspots and opportunities for improvements?”

  • “ChatGPT, I’m dealing with X dilemma. I am inclined to do Y. But I need you to help me think this through: what might I be missing? Help me find where I am being driven by fear and anger.”

  • “ChatGPT, what are my greatest strengths? And since everything is a double-edged sword, what do you think that means my weaknesses are?”

Utilizing introspection in this way helps operators go from just being good, to being sharp, focused, and great.

4. They don’t allow fear or competition to be their main driving force.

Peter Thiel famously said, “Competition is for losers.” Though he originally meant this as a call-to-action to focus on building a monopoly rather than competing in a crowded market, I think part of the way a company builds a monopoly is by focusing on what the customers actually want, instead of being obsessed with what their rivals are doing at any given point.

This doesn’t mean you shouldn’t be aware of what people in tangentially-related fields are doing - ignorance doesn’t solve anything! But again, it is the deliberate practice of putting a pause between whatever fear or paranoia you feel looking at your competition, and not allowing it to dictate your actions. If you allow it to dictate your actions, you will never stop playing catch up.

I love working with founders with a chip on their shoulder and something to prove, but a lot of the work we do in our sessions together is dialing back the paranoia and angst, focusing instead on what the fear is telling them, and then separating the emotional reaction from the appropriate response.

If you want to practice this, but you don’t yet have a coach, I’d recommend fear journaling. I write about this extensively in this article, and give you a play-by-play on how exactly to do this.

TAKEAWAYS:

• The best leaders understand that fear is a part of the process, but they don’t allow it to dictate their actions.

• They recognize that fear and anger help them remain alert and aware, but they will usually turn to their introspection practices and Challenge Network to recalibrate and respond, rather than react.

• Try fear journaling if you want an easy way to practice this solo.

Conclusion

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.