The Best Leadership Newsletter Ever | Jeff Matlow | Substack

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How To Work Smarter

368. You Hate The Answer As Much As The Problem

You think you just need to change your behavior. But that won't last. The real reason you stay stuck is something else entirely.

Apr 20

366. Why You Keep Choosing The Bad Option

You’d rather live with an outcome that you know is bad - everybody does it. But that doesn't mean the devil you know is a good choice.

Apr 6

364. Your Dog Smells Things You Can't. So Does Your Team.

The problem we have, as humans, is that we assume all beings experience the world the same way we do.

Mar 23

363. The Reason Your Team Doesn't Listen

You can't fix a listening problem with more talking. So stop trying.

Mar 16

362. Most Decisions Are Just A First Date

Most leaders get something wrong about most of their decisions. As it turns out, you can learn a lot from dating.

Mar 9

Leadership Lessons

371. What Made You Great Is Keeping You Stuck

Your pattern creates your environment. Your environment reinforces your pattern. That's the Pattern-Environment Loop. And you built it yourself.

May 11

370. The Questions You Won't Ask

As a leader, you'll question everything. Almost. The questions you won't ask are the reason why your beliefs are conspiracy theories.

May 4

367. It's Not The Conversation. It's You.

That difficult conversation doesn't need to be difficult. The main problem with it is you. Fortunately, I have an easy solution for how to have a…

Apr 13

362. Most Decisions Are Just A First Date

Most leaders get something wrong about most of their decisions. As it turns out, you can learn a lot from dating.

Mar 9

361. The Reasons You're Not A Micromanager

You're not a micromanager - we both know that. You just need to understand the reasons why you aren't one.

Mar 2

🤔 Life's Leadership Lessons

Welcome to The Best Leadership Newsletter Ever!

You’re now at the super secret page for new subscribers of The Best Leadership Newsletter Ever.

Mar 10 • Jeff Matlow

Life's Leadership Lessons: January 15, 2026

How leaders destroy their teams, how to manage a virtual team, how to communicate better in todays world, and so much more... this week in Life's…

Jan 15

Life's Leadership Lessons: January 8, 2026

How to build a culture of recognition, be a better leader, the best way to work with AI and so much more... this week in Life's Leadership Lessons

Jan 8

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Uncomfortable Truths

373. The Iceberg of Ignorance Is Bigger Than You Think

Leaders know 4% of company problems. The Iceberg of Ignorance explains the gap — and why your team will never tell you the truth.

May 25

372. You Are Not Your Personality Test

Your personality test isn't wrong. They way you're interpreting it is.

May 18

371. What Made You Great Is Keeping You Stuck

Your pattern creates your environment. Your environment reinforces your pattern. That's the Pattern-Environment Loop. And you built it yourself.

May 11

370. The Questions You Won't Ask

As a leader, you'll question everything. Almost. The questions you won't ask are the reason why your beliefs are conspiracy theories.

May 4

369. You Think You're Free. You're Not.

AI doesn't show you the truth. It shows you YOUR truth. Personalized, curated, and designed to keep you clicking. You think you have a choice. You…

Apr 27

Building A Better Culture

373. The Iceberg of Ignorance Is Bigger Than You Think

Leaders know 4% of company problems. The Iceberg of Ignorance explains the gap — and why your team will never tell you the truth.

May 25

367. It's Not The Conversation. It's You.

That difficult conversation doesn't need to be difficult. The main problem with it is you. Fortunately, I have an easy solution for how to have a…

Apr 13

360. You're Solving The Wrong Problem

You think this will never happen to you. But that's the whole point. When it does, you won't notice.

Feb 23

359. The Pattern You Can't See (That Everyone Else Can)

You’re secretly running two parallel systems, and the pattern you can't see is the one killing your company.

Feb 16

358. The Most Dangerous Word In Leadership

It isn't "quit" or "fail" or "lost". The most dangerous word in leadership is not what you think.

Feb 9

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Recent posts

7:27

Open Door Policies Are A Lie

70% of companies have an open door policy. Only 23% of employees actually use it. The door isn't the problem. You are.

May 22

The Standards You Lowered Without Noticing [AI Prompt]

The most dangerous compromises are the ones that happen slowly. This prompt helps you see the standards you lowered without noticing

May 19

372. You Are Not Your Personality Test

Your personality test isn't wrong. They way you're interpreting it is.

May 18

7:58

Core Values Mean Nothing

Listen now | Core values aren't statements. They're behaviors. Most companies have one and call it the other.

May 15

The Real Price Of Your Success [AI Prompt]

Success has a cost. This prompt reveals the relationships, identity, and parts of yourself you're trading away to achieve it.

May 12

371. What Made You Great Is Keeping You Stuck

Your pattern creates your environment. Your environment reinforces your pattern. That's the Pattern-Environment Loop. And you built it yourself.

May 11

7:35

Nobody Else Gets To Decide If You Failed

Listen now | You fired people. Lost clients. Shut it down. Nobody else gets to decide if you failed. That job is yours. Stop giving it away.

May 8

The Story You Tell About Failure Is A Lie [AI Prompt]

Everyone around you knows your relationship with failure better than you do. This prompt finally shows you what they see.

May 5

370. The Questions You Won't Ask

As a leader, you'll question everything. Almost. The questions you won't ask are the reason why your beliefs are conspiracy theories.

May 4

8:31

Atomic Habits Is Brilliant. And Wrong.

James Clear is probably a great guy. And Atomic Habits might be the most beautifully packaged way to get really good at doing the wrong thing.

May 1

The Real Reason You're Not Having That Conversation [AI Prompt]

You've got reasons to not have the conversation. The timing, the relationship, the quarter. This prompt finds what's actually underneath the reason…

Apr 28

369. You Think You're Free. You're Not.

AI doesn't show you the truth. It shows you YOUR truth. Personalized, curated, and designed to keep you clicking. You think you have a choice. You…

Apr 27

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