Sorta Bossy

Bring Back Shame, Bring Back Google

22 min · 23. kesä 2026
jakson Bring Back Shame, Bring Back Google kansikuva

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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 [http://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

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jakson Bring Back Shame, Bring Back Google kansikuva

Bring Back Shame, Bring Back Google

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 [http://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

23. kesä 202622 min
jakson 23 Ways to Exit Your Business Beyond Selling It kansikuva

23 Ways to Exit Your Business Beyond Selling It

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 [http://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

16. kesä 202620 min
jakson Do You Want to Lead, or Just Be in Charge? (with Trudi Lebron) kansikuva

Do You Want to Lead, or Just Be in Charge? (with Trudi Lebron)

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 [http://trudilebron.com], on her weekly email Working Hypothesis, and on her podcast, where Adrienne appears in the episode "I Had To Shed This Skin [https://podcasts.apple.com/ca/podcast/2-i-had-to-shed-this-skin-adrienne-dorison-on-letting/id1890004836?i=1000760382416]." 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

9. kesä 202645 min
jakson Is It a Business or a Job With Lipstick? kansikuva

Is It a Business or a Job With Lipstick?

Women own 40% of all businesses in the United States and represent just over 1% of business exits. Adrienne has thoughts about that, and she's not holding back. In this solo episode, Adrienne makes the case that if your business can't run without you, it's not actually a business. It's a job with lipstick. She walks through why female founders in particular get stuck in owner dependency, what it costs them, and what it actually looks like to start building a real exit. What she covers: * The difference between a business that's an asset and one that's a liability hiding in plain sight * Why women represent 40% of business owners but just 1% of exits, and what that gap is actually telling us * The identity trap: why stepping back feels like a betrayal, and why that feeling is keeping you stuck * At least six different definitions of "exit" that have nothing to do with selling your business * How removing owner dependency can two to three times the value of your business * The dog food website story: a retired dentist, millions of monthly views, and a wife who couldn't inherit any of it * Small business owners take an average of five days off per year, and 67% check in with work every day they're supposedly on vacation * The 90-day test: if you had to step away from your business tomorrow, would it survive? * The free Out of Office training and what Adrienne is covering there Free training: level11leaders.com/OOO [http://level11leaders.com/OOO] ⏱️ Time Chapters 00:00 Solo episode and kindergarten graduation chaos 04:10 Is your business an asset or a job with lipstick 08:30 The dog food website story 13:00 Women own 40% of businesses but represent 1% of exits 17:30 Why women exit unplanned and for less money 22:00 The identity trap and why stepping away feels like betrayal 27:30 Six versions of what an exit could actually look like 33:00 Owner dependency is costing you two to three times your valuation 37:00 The 90-day test 40:00 Out of Office [https://level11leaders.com/OOO] free training and close

2. kesä 202627 min
jakson The Gap vs. The Fix: The Only Feedback Framework You Need kansikuva

The Gap vs. The Fix: The Only Feedback Framework You Need

Most leaders think they're choosing between two options when it comes to feedback: be vague or just redo it yourself. Adrienne and Emily have a third take. In this Dear Bossy episode, Adrienne and Emily tackle a listener question about how to give feedback that actually sticks. They get into the difference between lazy and specific feedback, what it really means to delegate well, and why "make it stronger" does more harm than good. What they cover: * Why "make it stronger" and "make it better" are lazy feedback, not vague feedback, and what the difference actually means for your team * The false choice between being too vague or rewriting everything yourself, and the third option most leaders miss * How to turn subjective feedback into an objective standard your team can actually measure against * The gap vs. the fix: why naming the gap gives people ownership, and handing them the fix takes it away * What it looks like to give feedback on creative or preference-based work, and why rewriting with a walkthrough can actually be the fastest path to improvement * How standards change over time and why updating your team is not a one-time event * Emily's real example of getting "add more energy" as feedback and why it landed flat without context * The ego trap: unconsciously setting people up to fail so you can stay the only one who can do it right Submit your own Dear Bossy question: sortabossypodcast.com [http://sortabossypodcast.com] ⏱️ Time Chapters 00:01 Happy Tuesday and rainbow loom necklaces 04:05 Taylor-formations card of the week 06:21 The listener question 07:10 Emily's take: rewriting is not always the lazy option 09:47 The false choice and the third path 13:05 The ego trap in delegation 17:40 When standards change: the leader's responsibility to update the team 22:05 Emily's personal feedback example and user manuals 25:58 Choosing your hard: paying credit vs. paying cash 27:49 Wrap up

26. touko 202628 min