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

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Transcript