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.

8 hrs ago

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

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.

8 hrs ago

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

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

Building A Better Culture

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

354. How Leaders Destroy Their Best Teams

There’s one way leaders quickly destroy their best teams - and it's not how you think.

Jan 12

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Recent posts

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

4:41

Why Your Best Decisions Might Be Your Worst

There's a thing you do when you make decisions that makes you think you made a good decision. But it's all relative. Literally.

Apr 24

I Guarantee You're Doing Work Right Now That AI Can Do Better. [AI Prompt]

Most people know they should use AI more. This prompt shows you exactly where — and why you won't.

Apr 21

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

4:14

The Conversation You Keep Skipping

The thing about the perfect plan is that it can't be perfect if you build it by yourself. Here's the one conversation most leaders skip that is the…

Apr 17

Your Story Is True. It's Also A Trap. [AI Prompt]

There's a reason you haven't done that thing - or become that person. There's a story. And your story is true. That's the problem. It's a trap.

Apr 14

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

4:42

The Problem With Promotions

Here's what nobody tells you about job promotions - it's the easiest way to tell your team about what you value. And that's not always a good thing.

Apr 10

What Your Decision-Making Says About You [AI Prompt]

This is why your need for control is more powerful than your ability to trust others. You want the truth? I don't think you can handle the truth.

Apr 7

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