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?

They cover the red flags, the due diligence, and the question nobody asks out loud: Would you be relieved if they were gone?

Note: This is not legal or HR advice. Labor laws vary by state and country. Do your own due diligence on the legal side.

What they cover:

• Why most leaders wait too long -- and what it costs everyone else on the team
• The difference between firing someone for performance vs. letting someone go for business reasons
• How to have the expectations conversation if you never had it during onboarding
• What incremental improvement actually looks like and why you should be tracking it
• The cancer cell problem: how one disengaged person sets the new standard for everyone
• Red flags: working around someone, avoiding assigning them things, or people saying they'd rather do double the work than deal with that person
• The "would I be relieved?" gut check and when to trust it

Before you fire, ask yourself:

✅ Have I been crystal clear about expectations?

✅ Have I given them specific feedback on what needs to change?

✅ Have I given them adequate time and support to improve?

✅ Have I documented the issues? (protect yourself legally)

✅ Is this a performance issue or a fit issue? (both are valid reasons)

✅ Have I consulted HR/legal? (cover your bases)

✅ If they quit tomorrow, would I rehire them? (if no = fire)

✅ Am I keeping them out of guilt or because they’re actually contributing?

We love context! Submit your question to Dear Bossy: sortabossypodcast.com

⏱️ Time Chapters

00:01 Welcome and banter

07:55 Today's topic: when is it actually time to fire someone

09:01 Why leaders hold on too long and what makes it so hard

10:34 Firing for performance vs. letting someone go for business reasons

11:48 Why the firing should not be a shock if you have done the work

13:33 Start here: have you actually clarified expectations?

15:21 What the expectations conversation should look like

16:44 Give them a runway and look for incremental improvement

18:24 When they are not improving: what to track and when to act

19:27 The attention problem: your worst performer is getting 90% of your time

21:14 What the team sees when you protect one person at everyone else's expense

22:26 When someone is working the checkmate -- emotionally checked out and waiting to be fired

23:52 How one person's low standards become the new floor for the whole team

24:46 Red flag: you are working around them or avoiding giving them assignments

25:48 Red flag: people would rather work twice as hard than deal with that person

26:38 Red flag: you are nervous to bring things to them as the leader

27:24 The gut check: would you be relieved if they were gone?

29:22 How to define expectations backwards: what would great look like? What would bad look like?

31:50 Do not fire on vibes -- but do not wait forever either

33:18 The checklist: how to know when it is time

Transcript

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 for a 10-year colleague with it, and sends me client communications that are pure AI slop with no edits. She laughs about it openly. I want to bring it up but I don't want to cause an issue. What do I do?"

What they cover:

• Why using AI at work is not the problem -- outsourcing your human judgment is
• The "garbage in, garbage out" rule and why most people don't know how to delegate to AI any better than they delegate to humans
• Why a performance review written entirely by AI is a leadership failure, not a time-saving win
• A genuinely good use of AI for performance review.
• How to bring this up with your manager without making it a confrontation
• When to go directly to your manager vs. when to skip a level
  
  

⏱️ Time Chapters

00:01 Welcome to Dear Bossy

07:20 Today's question: my manager uses AI for everything

09:06 Adrienne's take: AI is fine, but the human elements still matter

11:34 Garbage in, garbage out -- why delegation to AI fails the same way delegation to humans does

13:22 Emily's recommendation: Natalie McNeil's ethical AI program

14:08 How training your AI changes everything

16:11 A genuinely good use of AI for performance reviews (Adrienne's brother's method)

18:05 Emily's suggestion: run the outputs through an AI detection tool

19:07 How to bring it up with your manager directly

20:36 What you actually need from a performance review that AI can't give you

21:32 When to skip a level if nothing changes

22:19 Rapid Fire with Emily

🔗 Links Mentioned:

• Submit a Dear Bossy question: sortabossypodcast.com
• Natalie McNeil's program on ethical AI use: https://nataliemacneil.com/ai-dream-team/
• Gemma Bonham-Carter's AI Allstars: https://gemmabonhamcarter.com/ai-all-stars
  
  Access the transcript here.

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.