The Bad Boss Brief Podcast

The Bad Boss Brief Podcast

A strategic guide on how NOT to be an asshole at work. An executive and an executive coach break down bad bosses, toxic workplace behavior, leadership failures, impossible coworkers, and what to do when work starts feeling impossible. badbossbrief.substack.com

Episodes

June 3, 2026 31 mins

In this episode of The Bad Boss Brief, we discuss:

- how judgement can help you set good boundaries

- can judgement and forgiveness co-exist

- why you want your bosses and partners to have good judgement and more

And, no, we’re not choosing topics based on Eugene’s tattoos but if the shoe fits...

Watch, listen, share with your friends!

As always, send us show ideas, comments or thoughts to wtf@badbossbrief.com.



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In this episode, we talk about what and if you really want to know. Do you want to know if your partner has cheated? Do you care how many people they had sex with before you? Or it is better to just not know?

Please note that we do talk, briefly, about Gisele Pelicot’s new memoir discussing her rapes and horrific abuse by her husband and others.

And no, we’re not going to tell you what Eugene reminded Stephanie of at the end of the e...

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May 6, 2026 31 mins

We answer your questions on surviving a lay off, using your words and freelance vs full time foolishness.

You, our favorite listeners, sent in some great questions and we get to some of them in this episode.

How does a man who was laid off from his public health job after budget cuts do better in interviews?

 What happens when your boss or co-workers don’t use their words but expect you to anticipate their needs? Eugene and Stephanie ...

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April 22, 2026 35 mins

Eugene and Stephanie talk about why they don’t use AI in their creative work, how AI has changed the notion of ownership, but not the fact that people who claim other artist’s work as their own should be roundly shamed and wonder if someone in the future is going to be surprised that writers like Eugene and Stephanie actually wrote their own s**t, from scratch, without AI?

From the Colson Whitehead article in the NYTimes

“Some people...

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April 8, 2026 37 mins

You make a plan. It’s a great plan. And then it all goes to s**t. It might be fate, terrible bosses, or a war.

- How do you navigate plans falling asunder?

- How important is perseverance?

- The value of staying flexible to stay employed.

- Can you reframe your metrics for success to make sure they are accurate?

All this and more in the audio or video version of The Bad Boss Brief Episode 79 The Best Laid Plans Show.

As always, send us s...

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March 25, 2026 34 mins

Life isn’t like a box of chocolates, but in today’s show we talk about analogies - how good ones can help teams learn, and bad ones can fan the flames of conflict. 

Listen or watch now, and please share this still free substack with your friends!

If you've got an idea for a show topic, message us here or email us at wtf@badbossbrief.com.



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March 11, 2026 32 mins

When we were growing up, we would never have believed that people would sign up to be tracked every minute of their lives.

Yet here we are.

Today we talk AI, surveillance, the dystopia we signed up for and why people make decisions that work against their well-being and throw away happiness with both hands.

Listen or watch now, and please share this still free substack with your friends!

If you've got an idea for a show topic, message ...

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February 25, 2026 32 mins

We talk about what you can do if you’re a worker with less power and what you can - and should - do as a leader or executive to build a culture of accountability.

How to handle illegal and unethical behavior as well as the irritating but not forbidden shirking of duties.

And the guy who went after his bad boss with a brick. Which we do not recommend.

Listen, watch and please share!

Eugene and Stephanie

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February 11, 2026 32 mins

When the world is burning and everything is very much not normal, how can you show up for work and keep your sanity, dignity and job?

Eugene's on tour, calling in from a coffee shop, and we're talking about how to navigate working when your life - or the world - is on fire. We talk about:

– The emotional energy it takes to pretend to be normal when you are not.

– Don't expect your employer to be much help.

– It's ok to allow yourself...

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How do you know if you’re in trouble at work and about to be laid off?

Eugene and Stephanie talk about:

– How do you know if you’re in danger of being laid off? We answer a listener's question and talk 

– PIPs (Performance Improvement Plans) and how to tell a good faith one from a bad faith one

– Why we don’t sue even when we could 

– What the face of your boss’s spouse can tell you about your professional future. 

– And Eugene’s newest ...

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January 14, 2026 32 mins

If you are starting the new year trying to decide whether to stay or go in a job, relationship or anything else you want to listen to this episode. 

Eugene and Stephanie talk about:

- The Potential Trap, where you stay because there’s “so much potential”

- Giving yourself permission to leave by challenging your ideas around quitting

- Why you can’t push rope

- Good reasons to stay in a bad situation

- The Two Year Rule - if these are you...

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December 17, 2025 33 mins

What if one friend can afford to retire early and the other can’t?

What if that friend is Eugene and Stephanie finally confesses her envy?

Listen as Eugene and Stephanie discuss:

- What to do if your friends or co-workers have more money than you do

- How being broke in your youth can impact you for the rest of your life

- What to do if fear of finances makes you ignore important money issues

- How to get back on track with basic financi...

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Stupid Men tricks? Stupid Women Tricks? Stupid Relationship Tricks?

Eugene and Stephanie argue gender dynamics.

Mostly we agree, but in the latest Bad Boss Brief (EP 71 Stupid Tricks: Gender Conflict) we talk about the ways in which the gender divide can cause problems at work and at home.

Choose someone and then try to get them to change?

Use your beauty and sexual attractiveness to win at work?

The “tyranny of expectations” and how Se...

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November 20, 2025 32 mins

“Job hugging” is on the rise as people cling to jobs during a time of economic and political uncertainty. How can you stay sane and employed when you’re terrified you’re going to lose your job? Watch the latest Bad Boss Brief for help.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses, bet...

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November 5, 2025 31 mins

"When people who are bad at something think they’re great and vice versa. Superpowers and how to find yours, managing with superpowers.” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses, better leadership, and unpack how to recognize if you’re...

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Mark as Played

“When we try anything new – a new sport or skill or language – we are bad before we get good. But that very badness can be a gift.” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses, better leadership, and unpack how to recognize if you’re the ...

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Mark as Played
October 8, 2025 33 mins

“In an age where politics are hard to avoid at work, we talk about people making it a performance. Plus, how to protect your social media posts from your boss and the death threats Eugene got.” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses,...

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Mark as Played
September 23, 2025 33 mins

“When your mental health is suffering so acutely that you can’t work, the last thing you need is a catchphrase like the currently trendy “quiet cracking”. You need to understand that no one in corporate America is coming to save you. But we’ve got some ideas that might help.” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and ...

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Mark as Played
September 10, 2025 32 mins

“A reader asks about annual reviews. Spoiler alert – we hate them. We talk why, what to do better, and how not to be a Bad Boss with annual reviews.” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses, better leadership, and unpack how to recogn...

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Mark as Played
August 27, 2025 33 mins

“How do you work with a star performer who's brilliant but hard to fit in? Or maybe that's you?” Listen for more on the latest Bad Boss Brief.

Welcome to the Bad Boss Brief — your no-BS guide on how NOT to be an a*****e at work. Hosted by an executive and an executive coach, we dive into real stories and practical insights on bad bosses, better leadership, and unpack how to recognize if you’re the problem.

Together, we bring over 50 ...

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Mark as Played

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