The Best Leadership Podcast Ever (with Jeff Matlow)

The Best Leadership Podcast Ever (with Jeff Matlow)

Life changing leadership lessons with a lump of laughter. Imagine if John Oliver and Simon Sinek had a baby. This is it. I’m the baby.

Episodes

106. Most decisions are just a first date

June 15, 2026 • 12 mins
Most leaders aren't bad at making most decisions — they're just terrible at knowing what kind of decision they're actually making. The result? Analysis paralysis, stalled innovation, and a team too scared to move without permission.
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105. The law of holes

June 8, 2026 • 9 mins
When you find yourself in a hole, what’s the first rule? Stop digging. In this episode, Jeff breaks down the law of holes and why leaders often make things worse by doubling down.
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104. The shadow system killing your company

June 1, 2026 • 11 mins
Every organization has an Official System: the values, metrics, and standards you say you hold everyone to. And a Shadow System: the unwritten rulebook that decides who those standards actually apply to.
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103. The leadership shortcut you need to know about

May 25, 2026 • 9 mins
Everyone wants the hacks, but real leadership doesn’t come with a secret key. There is no leadership shortcut. Learn why the hard way is the only way - and how that’s actually a good thing.
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102. The easy solution to difficult conversations

May 18, 2026 • 11 mins
Learn why difficult conversations fail before they start and discover the C.A.R.E. framework that turns confrontation into collaboration.
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101. You’re solving the wrong problem

May 11, 2026 • 10 mins
You've heard the frog-in-boiling-water metaphor a thousand times. Here's what nobody talks about: you're not the frog. You're the chef - and you're solving the wrong problem.
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100. The importance of environmental psychology

May 4, 2026 • 9 mins
The space you lead in is leading you right back. In this episode, Jeff explores how your physical environments shape behavior and emotions - and why smart leaders take them seriously.
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99. You have actor-observer bias

April 27, 2026 • 9 mins
Ever wonder why people blame others but excuse themselves for the same behavior? It's the psychological trap of actor-observer bias - and you need to rise above it.
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98. The reasons you’re not a micromanager

April 20, 2026 • 8 mins
You're not a micromanager. Of course you're not. You're just detail-oriented. Sure. Let's go with that.
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97. The matching principle

April 13, 2026 • 10 mins
Ever feel like your communication isn’t landing the way you intend it to? It's time you understand the matching principle. It turns out, you're having the wrong type of conversation.
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96. This is the part where everything breaks | The 80-year leadership cycle

April 6, 2026 • 12 mins
Every 80 years, everything breaks. Revolutionary War. Civil War. World War II. And now us. It's not a coincidence. It's a pattern.
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95. Inside imposter syndrome

March 30, 2026 • 5 mins
Ever feel like you don’t belong, even when you’ve earned your seat at the table? You’re not alone.It's time to get inside imposter syndrome.
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94. The truth you’re not ready to hear

March 23, 2026 • 9 mins
The truth you're not ready to hear is that your team isn't ready to hear the truth. At least not today. The question is, how are you going to get them ready for tomorrow?
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93. Your biggest productivity problem

March 16, 2026 • 8 mins
When things aren’t getting done, it’s easy to blame the team. But what if the team is not your biggest productivity problem?
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92. The enshitification of work

March 9, 2026 • 10 mins
When “productivity” becomes code for stripping away humanity, work stops working. This is the way the enshitification of work is happening.
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91. The rites of passage

March 3, 2026 • 8 mins
Leadership isn’t a title - it’s a journey. Sometimes bumpy, but a journey nonetheless. It includes important rites of passage that shape the person you become.
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90. Better, cheaper, faster. Pick two.

February 23, 2026 • 9 mins
In leadership, like in life, you have three options: better, cheaper, faster. Pick two. Because that's all you ever get.
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89. The difference between influence and manipulation

February 16, 2026 • 8 mins
There's a difference between influence and manipulation. It's an ethical tightrope that leaders walk on. Try not to fall off - there's no net down there.
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88. The lunch break is dead | How leaders kill their own productivity

February 9, 2026 • 7 mins
Modern work has eroded real connection. How do we know? Because the lunch break is dead. And I'm not sure we're ever going to get it back. That's a big problem.
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87. This is the way you do everything

February 2, 2026 • 6 mins
How you approach the small tasks reveals a lot about how you’ll handle the big ones. The way you do one thing is the way you do everything.
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