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. 18 hr ago

    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

    25 min

  2. 30 Jun

    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

    44 min

  3. 23 Jun

    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 min

  4. 16 Jun

    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 min

  5. 9 Jun

    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 min

  6. 2 Jun

    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 min

  7. 26 May

    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 min

  8. 19 May

    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 min
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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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  • Creator
    Sorta Bossy Podcast
  • Years Active
    2k
  • Episodes
    22
  • Rating
    Explicit
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    © 2026 Sorta Bossy Podcast