The Best Leadership Newsletter Ever

349. The Leadership Truth You're Not Ready To Hear

Every person has a limited range of truths they are capable of accepting at any given moment. Maybe it's time to pry open your Overton Window.

Dec 1

14

5

7

November 2025

348. The Enshitification of Work

While businesses have over-optimized for profit they've sacrificed humanity. Welcome to the age of enshitification.

Nov 24

13

4

5

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

24

2

346. The Lunch Break Is Dead

The lunch break was the time of day where we built trust, loyalty and connection at work. When we killed the lunch break we killed connection. What…

Nov 10

7

2

October 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

6

4

1

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

6

1

343. The Only 3 Problems You Actually Have

Regardless of how unique your troubles, they can all be boiled down to 3 problems in your life: your head, your heart and your bank account.

Oct 13

13

3

342. Obama, Kirk, and the Leadership Lesson You Need Right Now

What do Obama, Erika Kirk, and a blunt VP have in common? They all reveal the same uncomfortable truth about leadership: you can't shake hands with a…

Oct 6

8

2

September 2025

341. The Importance Of Q-Tips In Your Career

Q-Tips push all the bad stuff deeper inside. All they do is make things worse. As it turns out, the same thing happens at work when you take things…

Sep 29

8

2

1

340. The Secret Way To Get Things Done Faster and Better

Getting things done is your job description. But it isn't a marathon. Success is a sprint. And this is your guide to doing it faster and better.

Sep 22

15

3

339. The Bridge Between Courage And Pity

Today I saw a one-armed man walking a three-legged dog. My reaction was nothing I'm proud of, but it did teach me a whole lot about courage and pity.

Sep 15

15

2

1

338. The Illusion of Progress

We work hard every day to check boxes off our to do lists, but what if all that work is merely an illusion of progress. Maybe if you could only…

Sep 8

15

7

2