When Is It Actually Time to Fire Someone?

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