Is It a Business or a Job With Lipstick?

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

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

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

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 there * The male anchors that shaped her life (her dad, her ex-husband, her business partnership) and what shifted when each one ended * How she ended up in a business partnership with Mike and why her original work was always the foundation of it * The four exits framework for female founders: sell, scale, step away, or succession plan * Why trying to be for everyone made her content confusing and what it took to finally plant the stake in the ground * Action creates clarity, not the other way around, and why waiting for confidence before taking a big step is backwards * What it felt like to be energetically liberated after years of making hard decisions one at a time * Emily's perspective from the outside: watching Adrienne go from turtling to fully lit up * The 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

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 back * How to build a vision compelling enough that people actually want to follow it -- and why most leaders skip this part * The difference between announcing a change and selling a change, and why one works and the other doesn't * If you're shrinking your ideas to make them more palatable before you even share them, you're surrounded by the wrong people * What healthy partnership dynamics actually look like: clear ownership, immense trust, and always knowing who gets the final call * Why 50/50 partnerships often create stalemates -- and the structural fix for it * What to do when family is on the team and you're avoiding a necessary decision to protect the relationship * The 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 [http://sortabossypodcast.com] Read Adrienne's article on communal misery. [https://open.substack.com/pub/adriennedorison/p/the-culture-of-communal-misery?utm_campaign=post-expanded-share&utm_medium=web] ⏱️ 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