Sorta Bossy

Middle management is the loneliest role in any organization. In this Dear Bossy episode, Adrienne and Emily respond to a listener who manages a tight-knit team of three, does all the invisible work of protecting them from above, advocates for their growth, and still ends up feeling like she's not really part of the group. It's a more common feeling than most managers will admit. What they cover: W...

Most personality frameworks collect dust after the first quiz. Lisa Cumes & Mario Teran use the Enneagram as an operating system for their business, their team, and every hard conversation they have to have. Mario and Lisa are a married couple who work together and coach other couples in business on how to build real alignment, not just a functioning working relationship. What they've figured...

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 i...

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 wi...

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...

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 c...

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...

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...

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 bo...

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 act...

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 ma...

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,...

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...

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? The...

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 f...

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 zer...

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 somethi...

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 feedba...

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 , a...

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 t...

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 rete...

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) pul...