Sorta Bossy

Sorta Bossy Podcast
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85% of leaders never get trained. If you became a manager, team lead, or founder without anyone actually teaching you how to delegate, fire someone, or hold people accountable—this show is for you. We're tearing up the old leadership playbook and figuring out what actually works. Hosted by Adrienne Dorison

  1. -5 дн.

    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 tipWhy Adrienne says you're both the a*****e, but the manager is the bigger one by a lotThe difference between communicating an expectation and publicly embarrassing someone into learning itWhat the manager should have said instead, and how long it would have actually takenWhy leaving people feeling like they have to walk on eggshells is one of the worst things a leader can do to a teamThe outsourcing critical thinking problem: when it's fair to expect employees to Google things and when it isn'tEmily'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 a*****e, 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 мин.

  2. 16 июн.

    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 enoughThe four exit categories: scale, sell, step away, and secession planning, and what falls under each oneWhy an exit does not have to mean a sale, and why thinking it does is keeping founders stuckHow long each exit path actually takes to prepare for, from 18 months to a decadeThe 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 behindWhy the operational work is the same no matter which exit you chooseThe free Out of Office training and what Adrienne is covering liveFree 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

    21 мин.

  3. 9 июн.

    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, 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

    46 мин.

  4. 2 июн.

    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 sightWhy women represent 40% of business owners but just 1% of exits, and what that gap is actually telling usThe identity trap: why stepping back feels like a betrayal, and why that feeling is keeping you stuckAt least six different definitions of "exit" that have nothing to do with selling your businessHow removing owner dependency can two to three times the value of your businessThe dog food website story: a retired dentist, millions of monthly views, and a wife who couldn't inherit any of itSmall business owners take an average of five days off per year, and 67% check in with work every day they're supposedly on vacationThe 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 ⏱️ 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 free training and close

    28 мин.

  5. 26 мая

    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 teamThe false choice between being too vague or rewriting everything yourself, and the third option most leaders missHow to turn subjective feedback into an objective standard your team can actually measure againstThe gap vs. the fix: why naming the gap gives people ownership, and handing them the fix takes it awayWhat 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 improvementHow standards change over time and why updating your team is not a one-time eventEmily's real example of getting "add more energy" as feedback and why it landed flat without contextThe 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 ⏱️ 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

    28 мин.

  6. 19 мая

    This One's for the Girls

    Some decisions don't feel like decisions. They feel more like a slow accumulation of clarity that finally gets too heavy to ignore. Adrienne has been moving toward something for years. This is the episode where she names it out loud. Adrienne and Emily sit down for a get-to-know-the-boss conversation that turns into much more than business. They unpack what it actually looks like to trust your gut over a long period of time, why Adrienne's work is now specifically for women, and what it costs to finally stop trying to be something for everyone. What they cover: Why Adrienne declared her work is for women only, and the personal losses and decisions over the past two and a half years that led her thereThe male anchors that shaped her life (her dad, her ex-husband, her business partnership) and what shifted when each one endedHow she ended up in a business partnership with Mike and why her original work was always the foundation of itThe four exits framework for female founders: sell, scale, step away, or succession planWhy trying to be for everyone made her content confusing and what it took to finally plant the stake in the groundAction creates clarity, not the other way around, and why waiting for confidence before taking a big step is backwardsWhat it felt like to be energetically liberated after years of making hard decisions one at a timeEmily's perspective from the outside: watching Adrienne go from turtling to fully lit upThe woo-woo side of Adrienne that has always been there and is now getting more room to breathe ⏱️ Time Chapters 00:00 Happy Tuesday and outfit swaps 05:00 Mother's Day recaps 09:51 The throttle heard round the internet 12:42 Losing two anchors: divorce and her dad 16:01 Exiting the partnership and why it was time 17:00 Not anti-men, just for women 18:27 Making the brave decision vs. waiting for clarity 20:09 Emily: she was doing this work long before Mike 22:00 Why women haven't invested in themselves the same way 23:38 Being a divorcee and all the other things that add to the work 24:35 Removing owner dependency: the four exits 30:50 A friend to all is a friend to none 31:36 Picking a card (and manifesting perfectly) 31:56 Going all in on the woo 34:02 Sandbox vs. ocean 37:15 You never have perfect clarity before the hard decision 43:41 Action creates clarity, not the other way around 45:22 Unfailing belief that everything works out

    54 мин.

  7. 12 мая

    Everyone Pushing Back On You? It Might Be Your Fault.

    When you're trying to move a business forward and the people closest to you won't budge, it is one of the hardest leadership situations there is. Especially when those people are a partner, a co-founder, or a family member. A listener asked: how do you implement real organizational change when the people around you are resistant, including someone in your family? Adrienne and Emily have been on both sides of this. They get into all of it. What they cover: Why resistance from partners usually starts with you pulling back before they even push backHow to build a vision compelling enough that people actually want to follow it -- and why most leaders skip this partThe difference between announcing a change and selling a change, and why one works and the other doesn'tIf you're shrinking your ideas to make them more palatable before you even share them, you're surrounded by the wrong peopleWhat healthy partnership dynamics actually look like: clear ownership, immense trust, and always knowing who gets the final callWhy 50/50 partnerships often create stalemates -- and the structural fix for itWhat to do when family is on the team and you're avoiding a necessary decision to protect the relationshipThe energy question: are the people around you raising your ceiling or quietly lowering it?Why your identity slowly shifts to match the average of the people you spend the most time with -- and why that should scare you into being more intentional about who's in the room Submit a question: sortabossypodcast.com Read Adrienne's article on communal misery. ⏱️ Time Chapters 00:01 Welcome and banter 13:01 Today's question: how do you implement change when partners and family members resist? 14:28 Start with the vision -- everything else is a sales pitch 16:00 Pushback vs. pullback: why resistance is often your own energy coming back at you 19:00 Emily's take: if you're constantly dimming yourself, you're in the wrong room 20:39 When you're not even excited about your own idea before you share it 22:01 You slowly become the average of the people around you 24:02 Making conscious choices about who gets to be in your orbit 25:24 What Adrienne knows about the person who asked this question -- and what she sees 26:24 Finding synergy in a partnership without abandoning who you are 28:31 How to communicate with partners before you take it to the team 30:17 Leadership has to pull the team forward -- not fight itself in front of them 31:00 What the best partnerships actually look like: ownership, trust, and a tiebreaker 31:38 Why 49/51 beats 50/50 every time 32:45 The tiebreaker board member role -- and when to bring one in 33:35 If you have decision-making authority, use it 34:26 When family is involved: get a mediator, not a miracle 35:06 The business has to come first if you want it to survive

    36 мин.

  8. 5 мая

    Be Bored and Rich: What Entrepreneurs Get Wrong About Passion, Purpose, and Resentment

    Resentment in business does not usually arrive all at once. It builds. And by the time most people name it, it has already started spreading to the team, the clients, and the work itself. Emily has worked alongside Adrienne for almost 10 years. She has watched the seasons shift. She has always had questions. In this episode, she finally asks them out loud. What they cover: Whether Adrienne has actually resented her business -- and what she's willing to say honestly about thatThe martyr trap: stopping your own paycheck to protect the team, and why the team never asked you to do thatWhy making huge decisions based on boredom is usually a trapWhy "be bored and rich" is actually a legitimate strategyWhat happens when you make your business responsible for your purpose, your identity, your joy, and your sense of self.How Adrienne's work with The Adventure Project changed how she thought about money and what the business was actually forEmily's perspective: what it looks like to watch a business owner disengage from the outside, and what she's had to learn about when to hold the line and when to let goWhere to start when resentment is building: values, communication, and not letting it sit Submit your own question: sortabossypodcast.comLearn more about The Adventure Project: adventureproject.org ⏱️ Time Chapters 00:01 Welcome and banter 07:20 Emily asks the question she's held for 10 years 08:44 Adrienne's honest answer 10:30 The martyr trap 13:45 Resentment vs. boredom 14:39 Be bored and rich 15:06 When the business becomes your everything 19:32 The Adventure Project and why it changed how Adrienne thinks about money 24:10 Fund great nonprofits -- don't start your own 26:00 What disengagement looks like from Emily's side 30:11 Where to look first when resentment is building 33:23 The cycle of doom 34:19 Don't ignore it. Don't blow it up. Investigate it.

    34 мин.
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85% of leaders never get trained. If you became a manager, team lead, or founder without anyone actually teaching you how to delegate, fire someone, or hold people accountable—this show is for you. We're tearing up the old leadership playbook and figuring out what actually works. Hosted by Adrienne Dorison

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    Sorta Bossy Podcast
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