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Dear Bossy: Help, I Feel Like a Monster When I Give Feedback 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 man
Time: 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 themHow to offer space without abandoning the conversationWhy crying is involuntary and not (usually) manipulativeThe two most common triggers: disappointment after giving their best effort, and frustration at being stuck in a repeated patternHow to tell when someone genuinely can't hear you yet vs. when you can keep goingWhy skipping feedback doesn't protect your team member, it just delays the inevitableHow to frame feedback as care, not punishmentWhy the way you deliver feedback needs to vary person to personA 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.
⏱️ Time Chapters00:00 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
GUID: c5d94f7f-12de-49bf-b446-640f6858f454
Release Date: 05/03/2026, 19:03:04
