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. 3D AGO

    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

  2. MAY 12

    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 min

  3. MAY 5

    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 min

  4. APR 28

    You Don't Really Need Those Three New Hires

    You don't actually need to hire three people. You probably need to stop thinking in extremes first. This week, a listener asked the question, "I need an EA, an ops person, and someone for client delivery -- but I only have the budget for one. Who do I hire first?" The answer is not who. It's what. And it's probably sooner and smaller than you think. Adrienne and Emily break down how to actually make this decision, why most people wait too long to hire anyone, and what to do if you can't afford a full-time person but genuinely can't keep doing everything yourself. What they cover: Why "I can only afford one hire" is usually a thinking problem, not a budget problemThe gig economy case for hiring smaller and sooner instead of waiting for the full-time budgetWhy three separate roles might actually be one person -- and how to figure that outStop hiring by title. Start by identifying which activities need to come off your plate firstThe two ways a hire actually generates ROI: they do revenue-generating work, or they free you up to do itWhy freeing up your time only works if you're actually spending that time on something more valuableHow to figure out whether to hire for EA, ops, or delivery -- and why the answer depends on where your time is actually goingDelegation is a muscle. Don't start with the 100-pound weightsWhat energy drain has to do with who you hire firstWhy AI agents are not a shortcut if you can't already delegate clearly to a human Submit a Dear Bossy question or listener question: sortabossypodcast.com Follow Adrienne on Instagram ⏱️ Time Chapters 00:01 Welcome and banter 09:33 Today's question: EA, ops, or delivery -- who do you hire first when you can only afford one? 10:02 Why one size fits all doesn't work here 11:21 Stop living in all-or-nothings: you don't need a full-time person to start 12:15 The gig economy makes smaller, sooner hiring more accessible than ever 13:35 It might not be three people -- it might be one person with overlapping strengths 16:10 The only two ways a hire actually generates ROI 17:59 Track your time first -- you cannot make this decision without the data 18:57 Delivery vs. EA: which one actually opens up revenue capacity? 19:26 Delegation is a muscle. Start with the five pound weights 21:04 Hire for what drains you most, not just what takes the most time 22:19 AI agents are not a workaround if you can't delegate clearly to begin with 23:45 How to figure out what to automate vs. what actually needs a human 24:41 The time tracking case -- know exactly how many hours you need before you hire 25:34 Final thoughts: start smaller, start sooner, and use your freed-up time intentionally

    26 min

  5. APR 21

    Revenue Is Down, and Someone Has to Go. Now What?

    Every business dips. If yours hasn't yet, you just haven't been in it long enough. This week a listener asked one of the most real, vulnerable questions we've gotten: revenue is down, you need to let someone go, now what? How do you actually reabsorb their role without drowning, and how do you ramp back up when you're ready? Adrienne and Emily have both lived this. They get into the full picture, the mindset, the framework, and what it actually looks like inside a small team going through a contraction. What they cover: Why dips are not a sign you're failing, and why one investor won't back anyone who hasn't had oneThe difference between letting someone go for performance vs. letting someone go because the business has changed direction, and why the second one is actually harderHow to look at your team like a coach, not a friend: who do you need for where you're going, not where you've beenThe 4T framework for reabsorbing a role: Trash, Trim, Transfer, and where AI fits in nowWhy you should do a time audit before you reassign anythingHow to keep team morale up when the remaining people are scared they're nextWhat to do when someone has to absorb a role that isn't in their natural strengths -- and why giving them grace and space matters more than speedThe clean slate exercise: if you were starting from zero, what would you actually build?Why limited resources produce better creativity than unlimited onesHow to leave the door open with people you let go -- and why that matters more than you think Submit your own questions at www.sortabossypodcast.com ⏱️ Time Chapters 00:01 Welcome and banter 13:16 Today's question: revenue is down, someone needs to go -- how do you reabsorb their role? 13:45 If you haven't had a dip, you haven't been in business long enough 15:40 Contraction and expansion: this is just part of it 16:37 When the business changes direction and good people no longer fit the new model 17:29 How to evaluate your current team against where the business is actually going 18:27 Why financial pressure sometimes forces the business decision you should have made months ago 19:49 Ask yourself: if this were a client's business, what would you tell them to do? 20:16 Start with a time audit -- know what's on everyone's plate before you reassign anything 20:46 The 4T framework: Trash, Trim, Transfer, and where AI comes in 23:28 Reabsorbing tasks into the remaining team: aligning strengths and capacity 24:20 How to keep morale up and make reabsorption feel like an opportunity, not a burden 25:41 Give people grace when they're learning something new -- especially if the previous person made it look easy 27:34 The clean slate exercise: go from zero to one instead of ten to one 30:23 Adrienne's own contraction story and what she had to reabsorb herself 33:27 You're not failing. The metrics just changed. 34:26 How to leave the door open with people you let go

    38 min

  6. APR 14

    Dear Bossy: My Team Won't Reply To Emails

    Dear Bossy is the advice column format of Sorta Bossy. Today's question, from an anonymous listener: "I send my team emails asking for updates, input, or confirmation, and half the time I just get nothing. I can see they read it, but they don't reply. Then I have to follow up in Slack or hunt them down in person, and suddenly they're like, yeah, I saw that. What am I supposed to do? Send a carrier pigeon? I feel like I'm nagging them constantly just to get basic communication. " Adrienne and Emily flip this one on its head. The team is not the problem. The system is. What they cover: Why emailing your team for updates is the first thing to fix, not the lastThe single communication channel rule and what happens when teams are operating across email, Slack, Voxer, WhatsApp, and the project management tool all at onceWhy asking for updates is actually asking your team to do extra work that reduces everyone's efficiencyThe daily standup format: wins, concerns, and tomorrowHow a project management tool with a Slack integration can give you visibility without a single follow-up emailWhy constantly asking for confirmation quietly signals that you don't trust your teamHow faster feedback loops prevent the thing leaders hate most: finding out the deadline isn't happening the day before it's due Submit a Dear Bossy question: sortabossypodcast.com ⏱️ Time Chapters 00:01 Welcome to Dear Bossy 05:12 Today's question: my team won't reply to my emails 07:34 Fix this first: pick one communication channel and stick to it 09:06 Emily's take from the team member side: why are you emailing when the answer is in the dashboard? 10:12 What you actually need: a project management system with real visibility 11:09 The daily standup: wins, concerns, and tomorrow 12:36 How concerns and roadblocks create a low-stakes space for honesty 13:57 Stop asking for updates -- it is not their job to babysit you 15:45 Why constant confirmation requests quietly destroy trust 16:01 How a project management system eliminates the late-night "did they do that?" spiral 17:55 Faster feedback loops: how to find out a deadline is slipping before it's too late 18:25 Making standups visible to the whole team so others can step in and support 19:22 The bottom line: there should be no reason to email your team for internal updates 21:47 Rapid Fire with Adrienne Transcript

    27 min

  7. APR 7

    When Is It Actually Time to Fire Someone?

    Most leaders wait too long to fire. They hold on because it feels like the kind thing to do, or because they are not sure they have done enough, or because they just do not want to have the conversation. And the whole time, the rest of the team is paying for it. In this episode, Adrienne and Emily get into one of the hardest calls a leader has to make: when is it actually time to fire someone? They cover the red flags, the due diligence, and the question nobody asks out loud: Would you be relieved if they were gone? Note: This is not legal or HR advice. Labor laws vary by state and country. Do your own due diligence on the legal side. What they cover: Why most leaders wait too long -- and what it costs everyone else on the teamThe difference between firing someone for performance vs. letting someone go for business reasonsHow to have the expectations conversation if you never had it during onboardingWhat incremental improvement actually looks like and why you should be tracking itThe cancer cell problem: how one disengaged person sets the new standard for everyoneRed flags: working around someone, avoiding assigning them things, or people saying they'd rather do double the work than deal with that personThe "would I be relieved?" gut check and when to trust it Before you fire, ask yourself: ✅ Have I been crystal clear about expectations? ✅ Have I given them specific feedback on what needs to change? ✅ Have I given them adequate time and support to improve? ✅ Have I documented the issues? (protect yourself legally) ✅ Is this a performance issue or a fit issue? (both are valid reasons) ✅ Have I consulted HR/legal? (cover your bases) ✅ If they quit tomorrow, would I rehire them? (if no = fire) ✅ Am I keeping them out of guilt or because they’re actually contributing? We love context! Submit your question to Dear Bossy: sortabossypodcast.com ⏱️ Time Chapters 00:01 Welcome and banter 07:55 Today's topic: when is it actually time to fire someone 09:01 Why leaders hold on too long and what makes it so hard 10:34 Firing for performance vs. letting someone go for business reasons 11:48 Why the firing should not be a shock if you have done the work 13:33 Start here: have you actually clarified expectations? 15:21 What the expectations conversation should look like 16:44 Give them a runway and look for incremental improvement 18:24 When they are not improving: what to track and when to act 19:27 The attention problem: your worst performer is getting 90% of your time 21:14 What the team sees when you protect one person at everyone else's expense 22:26 When someone is working the checkmate -- emotionally checked out and waiting to be fired 23:52 How one person's low standards become the new floor for the whole team 24:46 Red flag: you are working around them or avoiding giving them assignments 25:48 Red flag: people would rather work twice as hard than deal with that person 26:38 Red flag: you are nervous to bring things to them as the leader 27:24 The gut check: would you be relieved if they were gone? 29:22 How to define expectations backwards: what would great look like? What would bad look like? 31:50 Do not fire on vibes -- but do not wait forever either 33:18 The checklist: how to know when it is time Transcript

    34 min

  8. MAR 31

    Dear Bossy: My Manager Has An AI Slop Problem

    Welcome to Dear Bossy, our Sorta Bossy advice column! Adrienne and co-host Emily Doyle answer questions from listeners (all submitted anonymously) and pull real scenarios from the messy middle of managing people. Today's question, from an anonymous listener: "My manager uses AI for literally everything -- and I mean everything. She used ChatGPT for my performance review, wrote a farewell message for a 10-year colleague with it, and sends me client communications that are pure AI slop with no edits. She laughs about it openly. I want to bring it up but I don't want to cause an issue. What do I do?" What they cover: Why using AI at work is not the problem -- outsourcing your human judgment isThe "garbage in, garbage out" rule and why most people don't know how to delegate to AI any better than they delegate to humansWhy a performance review written entirely by AI is a leadership failure, not a time-saving winA genuinely good use of AI for performance review.How to bring this up with your manager without making it a confrontationWhen to go directly to your manager vs. when to skip a level ⏱️ Time Chapters 00:01 Welcome to Dear Bossy 07:20 Today's question: my manager uses AI for everything 09:06 Adrienne's take: AI is fine, but the human elements still matter 11:34 Garbage in, garbage out -- why delegation to AI fails the same way delegation to humans does 13:22 Emily's recommendation: Natalie McNeil's ethical AI program 14:08 How training your AI changes everything 16:11 A genuinely good use of AI for performance reviews (Adrienne's brother's method) 18:05 Emily's suggestion: run the outputs through an AI detection tool 19:07 How to bring it up with your manager directly 20:36 What you actually need from a performance review that AI can't give you 21:32 When to skip a level if nothing changes 22:19 Rapid Fire with Emily 🔗 Links Mentioned: Submit a Dear Bossy question: sortabossypodcast.comNatalie McNeil's program on ethical AI use: https://nataliemacneil.com/ai-dream-team/Gemma Bonham-Carter's AI Allstars: https://gemmabonhamcarter.com/ai-all-stars Access the transcript here.

    27 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
    15
  • Rating
    Explicit
  • Copyright
    © 2026 Sorta Bossy Podcast

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