Episodi
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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 asshole, 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 asshole, 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 -
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 -
Episodi mancanti?
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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
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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.
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
What she covers: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 -
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.
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
What they cover:
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 -
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.
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
What they cover:⏱️ 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 -
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 roomSubmit 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
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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.
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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 humanSubmit 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
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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 thinkSubmit 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
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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 dueSubmit 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 -
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 -
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
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
🔗 Links Mentioned:
Access the transcript here. -
Most leaders don't set out to be people pleasers. But somewhere between wanting to be liked and trying to keep the peace, a pattern forms, and it becomes one of the most expensive habits a leader can have.
In this episode, Adrienne and Emily get into why making everyone happy is not actually your job as a leader, what it costs you when you try, and how to make hard decisions with high care and zero apology.
Emily admits it is her number one therapy topic. Adrienne has held onto team members longer than she should have and watched the rest of the team pay for it. This one is personal for both of them.
What they cover:
Why people pleasing feels like good leadershipThe cost of keeping one person happy at the expense of everyone elseHow to say no without abandoning the person you're saying it toWhy avoiding a hard conversation is never actually the kind choiceThe decision filter: is this what's best for the team, or is this just easy for me?What happens when leaders withhold context and then wonder why their team can't work autonomouslyThe "my way or the highway" trap and why it creates the exact problem it's trying to avoidHow generational differences in the workforce are changing what effective leadership actually looks likeHow to prepare for a hard conversation before you have it⏱️ Time Chapters
00:01 Welcome and today's topic: it's not your job to make everyone happy
01:11 Why people pleasing feels like leadership -- but isn't
06:33 How to say no as a leader while still being supportive
07:31 What people pleasing actually costs you: resentment, burnout, frustration
09:24 The filter: is this best for the team or just easy for me?
10:24 Holding onto the wrong person -- and what it does to everyone else
11:26 Emily's take: knowing what to do and being afraid to do it anyway
13:28 Enneagram types and why some leaders struggle more with this than others
14:44 What to notice: what are you taking on, avoiding, or not saying to keep people happy?
15:14 Real example: making a call both of them knew would frustrate people -- and making it anyway
16:16 The sunk cost fallacy and how to kill a project without guilt
17:35 High care doesn't mean avoiding hard calls -- it means preparing for them
19:07 How to lead a direction change: lead with "I understand this is frustrating"
20:31 Why leaving out context is why people can't get on board
21:14 The "my way or the highway" trap and why it creates dependent teams
25:39 What younger generations can actually handle -- and why leaders underestimate it
27:45 Gen Z getting fired at alarming rates -- is it a people problem or a leadership problem?
29:52 What you can and can't control as a leader
32:22 The decision filter, the post-it note, and making peace with not being liked
34:18 Closing thoughts and where to submit your Dear Bossy questions
Be sure to go to sortabossy.com to submit your leadership questions and horror stories!
Access the transcript here. -
Rachel Pedersen is a social media strategist, entrepreneur, and the kind of leader who will tell you exactly where she went wrong before she tells you what she got right.
In the first-ever interview episode of Sorta Bossy, Adrienne sits down with her friend of nearly a decade to talk about what it actually looked like to build a team, blow it up (relationally speaking), and rebuild it into something that has lasted almost nine years in an industry known for burnout and turnover.
This one gets real fast.
How Rachel accidentally became a boss by hiring a VA in 2015 with zero plan for what to give herThe "Tyra Banks era" of leadership -- and why rooting for people is not the same as leading themOperational whiplash: how Rachel's moods put her team in a constant state of eggshellsThe moment her sister looked her in the eye and said "I don't respect you".RST (Rachel Standard Time), the fake time zone her team invented to copeWhy avoiding hard conversations is not the kind choiceThe double standard women face when they're "snippy" vs. when men do the exact same thing from stageHigh care, high standards: why emotional intelligence is a leadership advantage, not a liabilityWhat Adrienne asked Rachel's team directly, and what they actually said
What they cover:
You can learn more about Rachel here.Grab Rachel's book Unfiltered
Enneagram Processing Guide
⏱️ Time Chapters
00:01 Welcome and why Rachel is the first interview guest
04:42 Hiring her first VA with no plan
08:20 The Tyra Banks era of leadership
09:42 Operational whiplash and the client who held up a mirror
10:47 The moment her sister said "I don't respect you"
14:48 RST: Rachel Standard Time
22:29 Knowing and owning your weaknesses
25:39 How Adrienne got into the Enneagram and why she got certified
28:31 Rachel's biggest leadership regret: avoiding hard conversations
32:07 The double standard women face when they're direct
33:46 High care, high standards
36:11 Rachel's mama bear model in action
37:07 What Adrienne asked Rachel's team -- and what they said
42:41 The question Rachel's team wanted to ask her
52:46 Where to find Rachel Pedersen
Read the transcript here -
Dear Bossy is the advice column format of Sorta Bossy. Think Dear Abby, but for real leadership situations.
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:
"I have a team member who cries every time I try to give her feedback. Not harsh feedback — just normal, constructive feedback. The moment I start, she tears up and I feel like a monster. So I end up not giving her feedback anymore, which means she's not improving and I'm really frustrated. What do I do?"
Adrienne isn't a crier. Emily is (or was). Together, they cover both sides of this scenario with honesty and zero judgment.
Why stopping the feedback entirely is actually the worst thing you can do for you and for themHow to offer space without abandoning the conversationWhy crying is involuntary and not (usually) manipulativeThe two most common triggers: disappointment after giving their best effort, and frustration at being stuck in a repeated patternHow to tell when someone genuinely can't hear you yet vs. when you can keep goingWhy skipping feedback doesn't protect your team member, it just delays the inevitableHow to frame feedback as care, not punishmentWhy the way you deliver feedback needs to vary person to personA real story between Adrienne and Emily, an actual attitude reprimand call, and how processing time made all the difference
What they cover:
📋 Enneagram Processing Guide
🔗 Links Mentioned:Want to submit a question for a future Dear Bossy episode? Send it to Adrienne on social media or via email to [email protected]. All submissions are kept anonymous.
⏱️ Time Chapters00:00 Welcome to Dear Bossy — the advice column format
01:52 How to submit your own Dear Bossy questions
03:42 Today's question: what do you do when your team member cries during feedback?
06:49 Adrienne's take: don't stop giving the feedback
09:21 Emily's take: crying is involuntary — make space for it
13:48 When the crier is your own kid (and why that's relatable)
16:02 The "nothing burger" cry — when emotions surprise you
17:25 The rule: pause if they can't hear you, but always come back
18:51 Real story: Adrienne gives Emily an attitude reprimand call
20:51 Why processing time matters before moving to solutions
22:38 Mindful of the blame game — give people room to process
23:19 The Enneagram processing guide and knowing your people
24:14 Final takeaway: deliver with care, directness, and don't stop
Find the transcript here -
Adrienne is joined by co-host and team member Emily Doyle for the first time, and they're diving into a topic that's deeply personal and deeply backed by research: why women leaders get labeled as cold, bossy, aggressive, or intimidating. and what's really going on underneath those labels.
Adrienne shares the story of the first time she was called cold at age 21 or 22, in a group staff meeting, and how she unknowingly carried that label for years.
Emily shares her own experience being called "the bitch down in pastries" at 19 during a dinner service. Sound familiar? It probably does.This isn't just lived experience. The data backs it up.
The research they cover:
The Double Bind Study: women were seen as either competent or likable, but rarely both. Men? Both simultaneously.The Abrasive Label Study: out of 248 performance reviews, the words "abrasive," "bossy," or "aggressive" appeared 71 times in women's reviews and zero times in men's.Research showing men's critical feedback focused on skill development, while women's focused on personality criticism ("watch your tone").When men express anger at work, they're seen as high status and competent. When women express the exact same emotion, they're seen as out of controlThe Heidi/Howard Study: identical case studies, only the name changed.Women score higher than men in 11 of 12 emotional intelligence competencies and score 3–5 points higher on EQ overall.Teams led by high-EQ leaders show better performance, higher engagement, and lower turnover.What "cold" usually really means: She had boundaries. She didn't manage my emotions for me. She didn't perform femininity the way I expected.
What to do instead of shrinking: Adrienne and Emily talk through the "high care, high standards" model, how to deliver direct, clear feedback in a way that communicates warmth without softening your standards or apologizing for your competence.
They also cover:
Why women internalize these labels and sometimes start performing themAI and ChatGPT as an echo chamber of society's gender bias (Adrienne's story about being recommended second to a list of men)The "ask questions" strategy for responding to inappropriate or passive-aggressive comments in the workplaceWhy the data shows women are actually more wired for modern leadership.
⏱️ Time Chapters00:00 Welcome & introducing co-host Emily Doyle
05:31 Today's topic: Why women leaders get called cold
06:57 Adrienne's first "cold" label at 21 — and how it stuck
11:16 Emily's story: "The bitch down in pastries"
13:05 What "cold" usually actually means
16:06 The research: The Double Bind Study
17:23 The Abrasive Label Study — 71 vs. zero
18:34 Personality criticism vs. skill feedback in reviews
19:22 The Heidi/Howard Study
24:50 High care, high standards — how to add warmth without shrinking
25:09 What cold feedback vs. warm-direct feedback sounds like in practice
31:34 Why women may be more wired for modern leadership
33:33 The 69% stat and why high EQ is a competitive advantage
35:00 The "ask questions" strategy for handling inappropriate comments
Follow Adrienne on Instagram!
Transcript -
If you've hired people, handed off tasks, and somehow still find everything coming back to you, this episode is the one you need.
Host Adrienne Dorison breaks down why delegation isn't a skills problem. It's an identity problem. And no framework is going to fix that.This solo episode digs into the deeper psychological reason high performers struggle to let go, and what it actually takes to make the shift from doing the work to leading the work.
Why the skills that got you promoted are now working against youThe real reasons you can't delegate (hint: it's not your team's incompetence)The 4 hidden fears underneath every delegation struggle: losing control, becoming irrelevant, being exposed, and discomfortWhy over-helping your team is actually holding them backThe James Clear / Atomic Habits quote Adrienne returns to constantly: "Every system is perfectly designed to get the results it's currently getting"Digging holes vs. solving Rubik's Cubes: a framework for understanding why leadership work feels less satisfying than doing work (dopamine, instant gratification, and delayed payoffs)The guilt loop that keeps leaders stuck even after they intellectually understand the shiftA real client story: a visionary founder whose "coffee shop days" became a team-wide metricWhy your team's capability is now the true measurement of your success
In this episode:🔗 Links mentioned:
📋 Delegation Scripts🎓 Delegation ClassReflection question for this episode: Who am I if I am not the one doing the work?
⏱️ Time ChaptersTimestamp
00:00 Why Everything Is Still On Your Plate
01:17 The Identity Problem Behind Delegation
04:57 The Hidden Fears Underneath "I'll Just Do It Myself"
07:36 The Danger of Over-Helping Your Team
10:02 Digging Holes vs. Solving Rubik's Cubes
14:49 The Guilt That Keeps Leaders Stuck
18:47 Client Story: Coffee Shop Days as a Team Metric
22:59 What Your Real Job Actually Is
24:47 Reflection + Your Homework
25:57 Resources: Delegation Scripts & Class
Access the transcript here -
Most leaders were never actually taught how to lead, and this episode names that truth out loud.
Host Adrienne Dorison opens Season 1 by diving into why so many of us ended up in leadership roles completely unprepared, and what we can do about it.Drawing on her years in corporate manufacturing and 15+ years in operational efficiency, Adrienne shares a candid story from her paper mill days, a retention survey that revealed exactly what employees needed, presented to the C-suite, and promptly ignored. Sound familiar?
Why being a great "doer" doesn't automatically make you a great leaderThe sobering stats: 85% of leaders are winging it, and 69% of employees say their manager impacts their mental health more than their doctor, therapist, or partnerThe 3 broken beliefs of the old leadership playbook (and why they're costing you talent)The 3 principles of the new leadership playbook: results over presence, clarity over control, and humanity over authoritarian hierarchy3 gut-check questions every leader should ask themselves regularly
In this episode:Your homework: Answer these three questions honestly:
Would I want to work for me?Is this how I would want to be led?Does this get results — or is it just leadership theater?⏱️ Time Chapters00:00 The Challenge of Modern Leadership
05:32 Old Models vs. New Models of Leadership
10:40 The Broken Beliefs of Leadership
21:30 Building a New Leadership Playbook
26:53 Self-Reflection as a Leader
You can read the transcript here
Please rate, review and subscribe if you loved this episode!
Connect with Adrienne on IG -
Welcome to Sorta Bossy!
If you found yourself in a leadership role without a roadmap, you're in the right place. Sorta Bossy is the podcast for managers, team leads, directors, and business owners who are figuring out leadership in real time, without the toxic boss energy.
Host and operational efficiency expert (and co-founder of Run Like Clockwork, alongside Clockwork author Mike Michalowicz) pulls back the curtain on the people side of leadership — the part no one trains you for.
Here's the reality:
Only 15% of leaders receive any formal leadership training85% are winging it69% of employees say their manager has a bigger impact on their mental health than their doctor, therapist, or partnerThis show exists to close that gap.
What to expect:
🎙️ Solo episodes: tactical breakdowns on delegation, firing, accountability, feedback, and more🤝 Leader interviews: real talk about real mistakes and hard-won lessons💌 Dear Abby-style episodes: with co-host Emily, answering listener questions and reacting to real workplace dilemmasThis podcast is for you if you're a leader who wants to drive real results without creating a toxic culture in the process.
Subscribe, leave a review, and share with a fellow manager who needs this.
You can read the transcript here
Connect with Adrienne on IG
