The Best Leadership Newsletter Ever | Jeff Matlow | Substack

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How To Work Smarter

357. This Is The Part Where Everything Breaks

We're in an 80-year cycle and I'm not sure your leadership will survive. This is the part where everything breaks.

Feb 2

356. The Leadership Skill Nobody Trains You For

Most leaders think they struggle with risk. They don’t. They struggle with uncertainty.

Jan 26

347. The Leadership Mistake Almost Every Manager Makes

You don't succeed by pretending everyone's elite - you do it by coaching the right people the right way. That's the Skill Will Matrix.

Nov 17, 2025

345. Better. Cheaper. Faster. Pick Two.

In leadership, as in life, you can't have it all. There are trade-offs for every choice. You want it better, cheaper and faster. You only get two…

Oct 27, 2025

344. How Great Leaders Win By Inches

In leadership, just like in baseball, the difference between winning and losing isn’t the big swings — it’s the tiny, incremental plays in between…

Oct 20, 2025

Leadership Lessons

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

357. This Is The Part Where Everything Breaks

We're in an 80-year cycle and I'm not sure your leadership will survive. This is the part where everything breaks.

Feb 2

356. The Leadership Skill Nobody Trains You For

Most leaders think they struggle with risk. They don’t. They struggle with uncertainty.

Jan 26

355. When Being Exceptional Starts Holding You Back

You’re smart. You’re talented. I’m sure everything you touch turns to gold. That’s the problem.

Jan 19

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

🤔 Life's Leadership Lessons

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

Life's Leadership Lessons: December 18, 2025

Discover your own personal strengths, 5 chatGPT prompts that will change your life, use AI to work faster, and so much more... this week in Life's…

Dec 18, 2025

Recommendations

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Decoding Customer Experience

Mark Levy

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Uncomfortable Truths

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

355. When Being Exceptional Starts Holding You Back

You’re smart. You’re talented. I’m sure everything you touch turns to gold. That’s the problem.

Jan 19

353. What I Got Wrong About Leadership

I didn’t learn the leadership lessons I teach because I was always good at them. I learned them because I was a lousy leader for a long time.

Jan 5

351. The 5 ChatGPT Prompts That Will Change Your Life

I didn’t realize how little I understood about myself until ChatGPT explained it to me. This is Leadership Therapy, the AI way.

Dec 15, 2025

Building A Better Culture

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

350. AI Isn't The Problem. Your Decisions Are.

Company leaders are treating AI as the solution, but they haven't even defined the problem. Spoiler Alert: your decisions are the problem.

Dec 8, 2025

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Recent posts

5:39

[Audio Thoughts] Customer Service Isn't About Solving Problems

Some thoughts on the real purpose of customer service, and why so many are failing at it.

Feb 20

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

5:40

[Audio Thoughts] Thermometer vs Thermostat Leadership

Most leaders are thermometers. And that's the problem.

Feb 13

[AI Prompt] CEOs Pay Millions For This

Senior leaders have expert advisory boards. You don't. This prompt will give you the exact advisory board you need to grow.

Feb 10

8:09

[Audio Thoughts] Burned Out Or Bored?

If you don't know the difference, you're going to try to fix the wrong problem.

Feb 6

[AI Prompt] The Life Changing Question

For 20 years, my career had been following the same pattern. I never realized it until I used this prompt. Now I won't ever be able to unsee it.

Feb 3

357. This Is The Part Where Everything Breaks

We're in an 80-year cycle and I'm not sure your leadership will survive. This is the part where everything breaks.

Feb 2

6:40

[Audio Thoughts] Why Your Best Employees Quit

Your best employees are leaving for a reason. And, spoiler alert, it's not them... It's you.

Jan 30 • Jeff Matlow

38:42

The Curse of the Exceptional Worker

If you're an exceptional worker, you should probably listen to this.

Jan 28 • Jeff Matlow

[New AI Prompt] Seeing Yourself From Their Perspective

That’s the thing about self-awareness. Whatever perspective you have is biased by that very perspective.

Jan 27

8:18

[Audio Thoughts] Alex Pretti + The 80 Year Cycle

It's not just about the shootings in Minneapolis, it's about a pattern that's lasted for centuries.

Jan 26 • Jeff Matlow

356. The Leadership Skill Nobody Trains You For

Most leaders think they struggle with risk. They don’t. They struggle with uncertainty.

Jan 26

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