Sorta Bossy – Details, episodes & analysis

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.

What they cover:

• Why stopping the feedback entirely is actually the worst thing you can do for you and for them
• How to offer space without abandoning the conversation
• Why crying is involuntary and not (usually) manipulative
• The two most common triggers: disappointment after giving their best effort, and frustration at being stuck in a repeated pattern
• How to tell when someone genuinely can't hear you yet vs. when you can keep going
• Why skipping feedback doesn't protect your team member, it just delays the inevitable
• How to frame feedback as care, not punishment
• Why the way you deliver feedback needs to vary person to person
• A real story between Adrienne and Emily, an actual attitude reprimand call, and how processing time made all the difference

🔗 Links Mentioned:

• 📋 Enneagram Processing Guide
  

Want to submit a question for a future Dear Bossy episode? Send it to Adrienne on social media or via email to support@level11leaders.com. All submissions are kept anonymous.

00:00 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 control
• The 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 them
• AI 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 workplace
• Why the data shows women are actually more wired for modern leadership.
  

00:00 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.

In this episode:

• Why the skills that got you promoted are now working against you
• The 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 discomfort
• Why over-helping your team is actually holding them back
• The 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 shift
• A real client story: a visionary founder whose "coffee shop days" became a team-wide metric
• Why your team's capability is now the true measurement of your success

🔗 Links mentioned:

• 📋 Delegation Scripts
• 🎓 Delegation Class
  

Reflection question for this episode: Who am I if I am not the one doing the work?

Timestamp
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?

In this episode:

• Why being a great "doer" doesn't automatically make you a great leader
• The 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 partner
• The 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 hierarchy
• 3 gut-check questions every leader should ask themselves regularly

Your homework: Answer these three questions honestly:

1. Would I want to work for me?
2. Is this how I would want to be led?
3. Does this get results — or is it just leadership theater?

00:00 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 training
• 85% are winging it
• 69% of employees say their manager has a bigger impact on their mental health than their doctor, therapist, or partner

This 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 dilemmas
  

This 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

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.

What they cover:

• How Rachel accidentally became a boss by hiring a VA in 2015 with zero plan for what to give her
• The "Tyra Banks era" of leadership -- and why rooting for people is not the same as leading them
• Operational whiplash: how Rachel's moods put her team in a constant state of eggshells
• The 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 cope
• Why avoiding hard conversations is not the kind choice
• The double standard women face when they're "snippy" vs. when men do the exact same thing from stage
• High care, high standards: why emotional intelligence is a leadership advantage, not a liability
• What Adrienne asked Rachel's team directly, and what they actually said

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

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 one
• The difference between letting someone go for performance vs. letting someone go because the business has changed direction, and why the second one is actually harder
• How to look at your team like a coach, not a friend: who do you need for where you're going, not where you've been
• The 4T framework for reabsorbing a role: Trash, Trim, Transfer, and where AI fits in now
• Why you should do a time audit before you reassign anything
• How to keep team morale up when the remaining people are scared they're next
• What 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 speed
• The clean slate exercise: if you were starting from zero, what would you actually build?
• Why limited resources produce better creativity than unlimited ones
• How 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

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 last
• The single communication channel rule and what happens when teams are operating across email, Slack, Voxer, WhatsApp, and the project management tool all at once
• Why asking for updates is actually asking your team to do extra work that reduces everyone's efficiency
• The daily standup format: wins, concerns, and tomorrow
• How a project management tool with a Slack integration can give you visibility without a single follow-up email
• Why constantly asking for confirmation quietly signals that you don't trust your team
• How 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

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 team
• The difference between firing someone for performance vs. letting someone go for business reasons
• How to have the expectations conversation if you never had it during onboarding
• What incremental improvement actually looks like and why you should be tracking it
• The cancer cell problem: how one disengaged person sets the new standard for everyone
• Red flags: working around someone, avoiding assigning them things, or people saying they'd rather do double the work than deal with that person
• The "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 is
• The "garbage in, garbage out" rule and why most people don't know how to delegate to AI any better than they delegate to humans
• Why a performance review written entirely by AI is a leadership failure, not a time-saving win
• A genuinely good use of AI for performance review.
• How to bring this up with your manager without making it a confrontation
• When 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.com
• Natalie 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.