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Barrett's Newsletter

On seeking advice, the timescales of change, and trusting our team to execute (2024 | Week 8)

Published 2 months ago • 5 min read

Hey Reader,


Shout out to Avaleen, Jason, Cory, Christian, and Dan for thoughtful replies over these past couple weeks. I’m thankful to be in conversation with talented, ambitious people like you.


Happy Saturday!

I won't hit you over the head with another "podcast coming soon" message. You know what it is on that front.

This was a week of blocking and tackling in my world. Client work. Family life. Production work on the new show. And taking care of my mind and body.

Feel free to drop me a note on how you're doing. I love hearing from you.

Let's get to it...


A quote to make you think from a book I think you should read

In a study by strategy researchers Michael McDonald and James Westphal, the worse companies performed, the more CEOs sought advice from friends and colleagues who shared their perspectives.

Company performance only improved when CEOs actively gathered advice from people who weren’t their friends and brought different insights to the table, which challenged them to fix mistakes and pursue innovations.


- Adam Grant, Originals

Adam Grant’s books have helped shape the way I think as a leader, operator, husband, father, and friend.

Originals in particular is an excellent read for thinking about:

  1. Building teams and cultures to drive higher levels of belonging AND performance
  2. Encouraging honesty about the challenges and problems within your organization
  3. Parenting children such that they grow up to live their lives based on strong principles and character
  4. Managing anxiety and worry so that you continue to make progress

And a bunch more. Adam writes some of the most well-researched books in the world with great storytelling and context intertwined. It’s worth a read if you haven’t already.


Three links to encourage deep thought and breakthrough growth


If there is a theme this week, it’s time. The time it takes to follow up on an idea. The time it takes for wisdom to penetrate our heart. The time it takes to change the world. I hope you enjoy.

1 Clockspeed by Sriram Krishnan | Read time: 2min (yes, really)

“The biggest determinant for success in a technology company is the speed at which it operates and learns.”

If you’ve been hear longer than a couple weeks, you know I love long form essays that are thoughtfully crafted and full of nuance. Give me length and you give me something to chew on, something to debate in my own mind.

Yet, in 200 words Sriram managed to communicate an idea that feels unequivocally true to me. In markets and companies where speed matters, there is a simple way to measure how seriously you take moving with intent.

Questions to consider as you read: What’s your organization's clockspeed? Is that on purpose? What should your organization’s clockspeed be? (I don’t default to shorter being better; in some organizations, longer might be the only appropriate answer — see the last reading suggestion for why.)

2 You Can’t Reach the Brain Through the Ears by Adam Mastroianni | Read time: 14min

“If someone could upend your entire sense of self by uttering a few sentences, we would constantly be under attack from the interpersonal equivalent of hydrogen bombs. But in protecting ourselves from attack, we also protect ourselves from wisdom.”


I have always done my best to seek wisdom from people smarter and more experienced than me. I’ve also always tried to apply the wisdom I gain from others to my own life, to various levels of effectiveness.

Mastroianni makes the argument that while it’s a worthy cause to try to pass on (or seek) wisdom, we’re wired not to receive it. At least we’re wired not to receive it in quick bits over short time periods. What’s the antidote? Seeking (or communicating) wisdom over long periods of time from consistent sources so that it might sit on our hearts long enough to be absorbed.

A worthwhile read for considering the ways we resist and reject the wisdom we’re offered.

Questions to consider as you read: From whom are you seeking wisdom right now? What wisdom have you received that you’ve failed to internalized? If you had to pick three people whose wisdom you would want to gain over the next decade, who would they be?

3 Pace Layering by Stewart Brand | Read time: 10min

“In order to survive, we have needed to be loyal to ourselves, to our families, to our tribes, to our cultures, to our species, to our planet. If our psychological impulses are complicated, it is because they were shaped by complicated and conflicting demands. - Freeman Dyson

Stewart Brand is simultaneously one of the most eccentric and one of the most inspiring figures in our world. He thinks unlike anyone I’ve ever met and he imagines futures most people will never even consider.

I discovered this essay in my research to interview Packy McCormick for my new podcast. In it, he argues for the balancing forces of the different layers of our world — from fashion to commerce to nature. Each layer changes on different time scales and in response to different forces.

We sometimes treat this as a bad thing, but it is what creates a resilient planet, which we should be grateful for.

Questions to consider as you read: On which layer, or timescale, does the problem you’re working to solve sit? How will your company change the layers downstream and upstream if it works in the best possible way?


An idea sparked by my client work to help you lead better

Every founder reaches a point when they have no more capacity to do the work themselves. Their calendar is full. Their Slack is blowing up with constant reminders set to stay on top of it. They’re warn out at the end of every day, but there’s still a never-ending to do list that gets larger by the day.

At that point you have two choices:

  • Keep trying harder until you burn out, get sick, or your team quits
  • Put trust in others to carry the standard and do great work

Putting trust in others feel like the scarier of the two options in the short term. What if the team makes mistakes? What if they have a lower standard than me? What if they’re not capable? What if they cause our best / most profitable / most important client or customer to shift to a competitor?

These things might come true. In fact, I can guarantee the team will make mistakes if you trust them with important work.

But can I ask you something? Do you remember when you were in their shoes? How many mistakes did you make? Did you learn from them? Did they help you grow? Did they lead you to where you are today?

You have to embrace the mistakes that the team will make in order to reach a new level of growth and possibility — for you, for your team, and for your company. You’ll be tempted to insert yourself into every project and process. Right before something ships you’ll be tempted to give feedback to make sure it’s perfect… just the way you’d do it.

But this runs counter to your goal. Your calendar and to-do list will fill with a new kind of task: checking the work of every person on the team before a customer sees it. This isn’t sustainable either.

No, you have to allow the mistakes to happen. It’s in the mistakes that you can learn together and calibrate on the standard of excellence going forward. It’s in the mistakes that your team will learn to set their own standards. Learn to check their own work. Learn to take pride in making things with excellence.

There’s only one way through the slog when you’re stretched to the edges of your capacity as a founder. It starts with trust.

But the real question… the one that might actually be holding you back… is this: how will you spend your time if you’re not at the center of every decision, product, or process? What would you do to serve your company’s mission if your team was more capable than you’re giving them credit for?

What would you do if you found out you had a world class team that shipped better work than you could on your own?

If you don’t know the answer to that, it might be the reason you’re stuck.


Much love and respect,


PS: Things you can do to support me...
Forward this newsletter to a founder friend
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Barrett's Newsletter

A newsletter for founders who want to make impact at scale and become the leader your team needs you to be

My newsletter helps founders like you become the leader you're capable of so you can make the impact you set out to make. Each week I share exceptional essays from around the web, original essays from my desk, and my long-form interview podcast called Good Work -- all centered on reaching your potential as a founder and leader. I'm an executive coach to founders and creators using business to solve hard societal problems - lessons from my coaching work directly fuel the newsletter.

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