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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Dear Bossy: Help, I Feel Like a Monster When I Give Feedback
Season 1 · Episode 4
Thursday, March 5, 2026 • Duration 25:22
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
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.
⏱️ Time Chapters
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
Cold, Bossy, Abrasive: The Labels Women Leaders Can't Win Against
Season 1 · Episode 3
Thursday, March 5, 2026 • Duration 38:26
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:
⏱️ Time Chapters
Why You're Still Doing Everything Yourself
Season 1 · Episode 2
Thursday, March 5, 2026 • Duration 25:30
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
Reflection question for this episode: Who am I if I am not the one doing the work?
⏱️ Time Chapters
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 Stuck18:47 Client Story: Coffee Shop Days as a Team Metric22:59 What Your Real Job Actually Is 24:47 Reflection + Your Homework25:57 Resources: Delegation Scripts & Class
I Have No Idea What I'm Doing
Season 1 · Episode 1
Tuesday, March 3, 2026 • Duration 32:04
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:
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 Chapters
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
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.
What My Team Really Thinks of Me (with Rachel Pedersen)
Season 1 · Episode 5
Tuesday, March 17, 2026 • Duration 54:51
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
00:01 Welcome and why Rachel is the first interview guest
04:42 Hiring her first VA with no plan
Revenue Is Down, and Someone Has to Go. Now What?
Season 1 · Episode 9
Tuesday, April 21, 2026 • Duration 38:02
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
13:16 Today's question: revenue is down, someone needs to go -- how do you reabsorb their role?
Dear Bossy: My Team Won't Reply To Emails
Season 1 · Episode 9
Tuesday, April 14, 2026 • Duration 26:38
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
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?
When Is It Actually Time to Fire Someone?
Season 1 · Episode 8
Tuesday, April 7, 2026 • Duration 34:14
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)
Dear Bossy: My Manager Has An AI Slop Problem
Season 1 · Episode 7
Tuesday, March 31, 2026 • Duration 27:09
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
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