A Reddit submission that must be discussed!

The writer's manager sent them a passive-aggressive link to "Let Me GPT That For You" instead of answering a simple question on a call they were already on.

The employee left and didn't come back the next day. Adrienne and Emily have opinions.

In this Dear Bossy episode, Adrienne and Emily dig into a viral-feeling workplace situation that splits people into two camps fast.

Was the employee out of line for asking something they could have Googled?
Or is the manager the bigger problem?

Turns out the answer is kinda both... but not equally.

What they cover:

• The "Let Me GPT That For You" link, what it actually does, and why sending it is an act of deliberate humiliation not a productivity tip
• Why Adrienne says you're both the asshole, but the manager is the bigger one by a lot
• The difference between communicating an expectation and publicly embarrassing someone into learning it
• What the manager should have said instead, and how long it would have actually taken
• Why leaving people feeling like they have to walk on eggshells is one of the worst things a leader can do to a team
• The outsourcing critical thinking problem: when it's fair to expect employees to Google things and when it isn't
• Emily's case for bringing back public shaming (and Adrienne's Game of Thrones reference to back it up)
• How to vent first, then distill it into an actual boundary or expectation

Submit your own Dear Bossy question: sortabossypodcast.com

⏱️ Time Chapters
00:01 Happy Tuesday and the female tax of getting camera-ready
04:15 Today's Dear Bossy situation
08:51 You're both the asshole, but not equally
12:00 The 10 leadership failures vs. the one employee growth area
14:08 Emily cannot fathom treating another human this way 16:21 Bring back shame, bring back Google
20:31 What good leadership actually looks like here
22:07 Vent first, then distill it into a real expectation

Adrienne just got back from New York Tech Week, where she spoke to a room of female founders about something most of them had never thought about before. She's not done talking about it.

In this solo episode, Adrienne breaks down the four categories of exits, why 24 different versions of an exit exist, and why most female founders are only picturing one of them.

She makes the case that building without an exit plan is not ambition. It's a liability in the making.

What she covers:

• What Adrienne spoke about at New York Tech Week and why the conversation is one we are not having nearly early enough
• The four exit categories: scale, sell, step away, and secession planning, and what falls under each one
• Why an exit does not have to mean a sale, and why thinking it does is keeping founders stuck
• How long each exit path actually takes to prepare for, from 18 months to a decade
• The insurance plan framework: if you step out tomorrow, does everything disappear with you?
• The dentist and the dog food website, and what happens when a seven-figure business is worth nothing to the person left behind
• Why the operational work is the same no matter which exit you choose
• The free Out of Office training and what Adrienne is covering live

Free training: level11leaders.com/OOO

⏱️ Time Chapters
00:01 Solo episode and New York City recap
04:42 What exit actually means, and the 24 versions most founders don't know about
09:23 How long each path takes and why you need to start now
13:59 The best time to plant a tree was 20 years ago
16:16 The dentist, the dog food website, and the wife who couldn't inherit any of it
18:39 Why we are not having this conversation enough and what Adrienne wants to do about it

Most leaders believe they have built an open, safe, equitable team. The team usually disagrees. The gap between those two things is where this whole conversation lives.

Trudi Lebron has spent 20 years as an equity practitioner, starting in education and youth development before making a deliberate move in 2017 to bring this work into the coaching and online business world.

Adrienne worked with her in back in 2020, and they have been crossing paths ever since. This time they sit down to talk about what equity actually means inside a company, and why so much of it comes down to power and how you use it.

What they cover:

• Why "we're not creating oxygen" became a guiding principle, and how it changes the energy a whole team runs on

• Why equity is so much bigger than race, and how it shows up in onboarding, work hours, and the structure people actually need to succeed

• The real reason most leaders stay quiet: not kindness, just fear of getting it wrong

• Why letting things slide is an abdication of responsibility, not good-boss behavior

• The difference between wanting to lead and wanting to be in charge

• Why power is neutral, and what owning it actually unlocks instead of avoiding it

• The restraint problem: what you steal from your team every time you jump in

• How middle managers become the dam, and what happens to the whole team when it breaks

• The psychological safety test: if no one pushes back, assume they do not feel safe

Trudi Lebron, MS, is a highly skilled executive coach and facilitator with over 20 years of experience helping public and private institutions, entrepreneurs, solopreneurs, and founders build equitable businesses, workplaces, and learning environments. She is the founder of The Institute for Equity-Centered Coaching, the author of The Antiracist Business Book (Row House Publishing, 2022), and a PhD candidate in Social Psychology.

Find Trudi at trudilebron.com, on her weekly email Working Hypothesis, and on her podcast, where Adrienne appears in the episode "I Had To Shed This Skin."

Time Chapters

00:00 How Adrienne and Trudi met

02:00 Why Trudi chose equity work

03:50 Equity is bigger than race

04:50 Equity meets capitalism

07:40 Never becoming the boss you hated

09:20 We're not creating oxygen

11:05 You can't teach people how to be free

12:45 Onboarding for how someone actually works

15:05 Equity serves the business too

17:25 Doing nothing for fear of getting it wrong

20:30 The expectation you never actually set

22:45 The power dynamic you don't want to admit

24:50 Power is neutral

27:00 Authority is given, not taken

29:00 Restraint as a leadership skill

30:40 Why you really jump in

32:40 Middle managers as the dam

40:05 Speaking up needs safety

41:50 How to know it's not safe

43:25 Where to find Trudi

44:50 The AI conversation they saved for next time