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