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. 1d ago

    You Don't Have Freedom. You Have Wi-Fi.

    You can pack the bags, take the flight, check into the hotel, and still end up sitting on the beach answering Slack. Most founders call that freedom because it happened somewhere new... but working in a new location does not equal freedom. Adrienne spent this Tuesday on the golf course and spent this week getting a biopsy she almost put off. Both of those are the same story. This solo episode kicks off a run of episodes built around one question: can your business actually run without you? What she covers: Why "I can work from anywhere in the world" is a sentence worth hearing yourself say out loudTwo out of office moments from Adrienne's week: a Tuesday tee time, and the doctor's appointment she came close to pushing off againLocation freedom is about where your body is. Mental freedom is about whether the business is still running in the back of your head while you're thereThe client who asked whether he was still allowed to think about his business during his four week unplugged, and the answer he gotWhy the big ideas only show up once the day to day noise clears outThe client who worked from the labor and delivery room and told herself it counted as freedomWhy remote work got optimized so well that your body can be anywhere while you stay completely trappedWhere to start: a free diagnostic that scores owner dependency across six categories Take the free out of office diagnostic: level11leaders.com/exit ⏱️ Time Chapters 00:00 The beach, the Slack, the lie 04:05 The appointment she almost skipped 08:58 Location freedom is not freedom 13:10 You optimized for the wrong one 17:15 Find out where your business needs you

  2. Jul 14

    Adrienne's In the Hot Seat

    Emily showed up with a list of questions and Adrienne had no idea what was coming. What followed was one of the more honest conversations they've had on the show. In this episode, Emily puts Adrienne in the hot seat for a rapid fire Q&A. No prep, no filter, and some answers that surprised even the person giving them. What they cover: The best advice Adrienne ever got and then ignored for years, and why she's finally living it this yearHow this has genuinely been one of the harder financial years in the business, and what the monthly conversations between Adrienne and Emily actually sound likeThe leadership mistake Adrienne had never said out loud until now: stepping back so far it became abdication, and what it cost the teamWhat Emily told Adrienne at the end of last year that changed how they work togetherA belief about hard work and success that Adrienne has completely reversed after years of watching other people build differentlyWhat Adrienne's team does better than her (almost everything, and she says so)Why rest still feels wrong when you're in a build phase, and the reframe that matters anywayThe difference between needing a vacation and needing spaciousness, and why no-call weeks might be more valuable than either Submit your own Dear Bossy question: sortabossypodcast.com ⏱️ Time Chapters 00:01 Sunkissed, frizzy hair, and heat waves in Canada 06:27 Emily has rapid fire questions and Adrienne knows nothing 08:16 Best advice ever gotten and completely ignored 10:39 The hardest conversations this year 12:32 Every month ends in a hype session 14:11 What the team does better than Adrienne 16:03 The leadership mistake Adrienne never admitted 18:55 What Emily told Adrienne that almost made her quit 22:08 A belief about hard work she's completely changed her mind on 24:03 The hat maker and Alex Hormozi in Kentucky 26:21 What does rest actually look like for you 28:50 You don't need the big picture ideas until you have the space for them 30:32 You don't have to earn rest

  3. Jul 7

    It's Lonely In the Middle

    Middle management is the loneliest role in any organization. In this Dear Bossy episode, Adrienne and Emily respond to a listener who manages a tight-knit team of three, does all the invisible work of protecting them from above, advocates for their growth, and still ends up feeling like she's not really part of the group. It's a more common feeling than most managers will admit. What they cover: Why your team bonding without you is actually a sign you're doing something right, even when it doesn't feel that wayThe invisible work of middle management: shielding your team from pressure, advocating behind the scenes, handling problems before they land on anyone else's deskWhy the middle is often the loneliest layer of any organization, and why that is by design, not failureThe difference between needing community and needing your team to provide itEmily's honest take on being the only person in the middle and what she did to navigate itHow to ask your organization for development, mentorship, or coaching and why your leadership is already spending money on exactly thatPractical ways to close the connection gap: therapy, peer networks, lunch and learns, industry events, and what happens when you just introduce yourself to the person next to youA teaser for something Adrienne and Emily are building specifically for operators and middle managers who need their own community Submit your own Dear Bossy question: sortabossypodcast.com ⏱️ Time Chapters 00:01 Periscope, Clubhouse, and the graveyard of dead platforms 04:15 Summer House, audiobooks, and brains with nothing left in them 09:55 The listener question: am I being unreasonable for feeling left out of my own team? 13:05 Your team bonding without you is actually the dream 14:01 The invisible work nobody sees and nobody thanks you for 15:07 Emily's take: the middle is the loneliest layer 17:54 Middle management is the most burned out role in any org 20:13 Ask for the development your leadership is already investing in themselves 22:07 Lunch and learns, industry events, and a little like dating 24:07 Stay tuned, something's coming for operators and middle managers

  4. Jun 30

    Why Your Business Partner Needs to Know Your Operating System with Lisa Cumes & Mario Teran

    Most personality frameworks collect dust after the first quiz. Lisa Cumes & Mario Teran use the Enneagram as an operating system for their business, their team, and every hard conversation they have to have. Mario and Lisa are a married couple who work together and coach other couples in business on how to build real alignment, not just a functioning working relationship. What they've figured out applies whether you're running a company with your spouse or just trying to lead people better. What they cover: Why alignment between partners, not hustle, is what actually makes a business run wellThe ARC framework as the foundation of any high-functioning partnership, personal or professionalHow to use the Enneagram as a shared language with a business partner, your team, and even clients you've never asked to take a personality testWhy understanding yourself has to come before you can effectively lead, communicate with, or support anyone elseWhat happens when couples in business put the revenue goals first and the relationship second, and why that order always backfiresThe walk and talk habit: a structured daily check-in that keeps small frustrations from becoming big blowups, and how to make it work with a packed scheduleHow to parent, lead a team, and manage client relationships using the same framework without ever asking someone their numberThe 30-day walk and talk challenge and where to find it Connect with Mario and Lisa and download their FREE 30 Questions for your next Walk & Talk PDF Guide: marioandlisa.com You can also grab their free enneagram guide here. Or connect with them on Instagram! ⏱️ Time Chapters 00:00 Introducing Mario and Lisa 04:15 What a real power couple actually looks like 05:54 Radical responsibility: you are not responsible for each other's happiness 07:01 Awareness and the Enneagram: how Mario found himself in a framework 11:44 Adrienne's Enneagram origin story and Ryan Levesque's team Slack 14:03 Understanding yourself first, then your partner 17:11 When two whole people leverage their differences together 21:27 You don't have to do it twice to get it right 25:32 Stop waiting for the business to be better before investing in the relationship 27:28 The walk and talk habit and why it works 31:36 If you can't walk 30 minutes with your partner, you have a bigger problem 36:09 Borrow 30 minutes from social media 37:30 Using the Enneagram with your kids 41:40 Where to find Mario and Lisa and the 30-day challenge

  5. Jun 23

    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

  6. Jun 16

    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

  7. Jun 9

    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

  8. Jun 2

    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

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About

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

Information

  • Creator
    Sorta Bossy Podcast
  • Years Active
    2026
  • Episodes
    24
  • Rating
    Explicit
  • Copyright
    © 2026 Sorta Bossy Podcast