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 leadership
• The cost of keeping one person happy at the expense of everyone else
• How to say no without abandoning the person you're saying it to
• Why avoiding a hard conversation is never actually the kind choice
• The 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 autonomously
• The "my way or the highway" trap and why it creates the exact problem it's trying to avoid
• How generational differences in the workforce are changing what effective leadership actually looks like
• How 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 Pederson 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 Pederson

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.

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