How do you know it’s time to fire someone? And is it possible to fire them with grace?

It is. I know because I’ve gently, diplomatically cut loose several employees and contractors who weren’t quite right for me or my company. I’ve coached CEOs at Fortune 100 companies through the process and helped entrepreneurs ‘right size’ their teams.


Surprisingly, firing with grace doesn’t start with an email or a phone call. It starts with acknowledging – to yourself – that someone isn’t the right fit for your team.


That sounds easy, doesn’t it? But I have seen so many clients talk themselves out of firing someone who’s clearly not right for their company and doesn’t want to be there. In fact, almost all of them say they waited and suffered too long in a bad working relationship.



How to know it’s time to fire someone (and things you can try before you do)

You know things aren’t working with your employee when: they regularly miss deadlines.

Before you fire them: Is this a new task? If so, maybe they simply need more help. If this is a task they’re well acquainted with, are you using Trello or Basecamp to manage projects and automate deadline reminders?

Is your turnaround time realistic? Have you communicated the urgency? If you’ve given them two weeks, you’re totally justified in being upset. If you’ve given them two hour’s notice on Friday afternoon without clarifying urgency, perhaps it’s time to adjust your expectations.


You know things aren’t working with your employee when: they’re not responding to your emails or phone calls.

Before you fire them: When you on-boarded them, did you address expectations around availability? Are they working for you full time or are they a contractor who’s juggling lots of other clients?

If they’re a full time employee who knows that you’d like them to respond to email within the work day, it might be time to have a tough conversation. If you’ve never talked about availability and accessibility, maybe it’s time to have that conversation!


You know things aren’t working with your employee when: They’re not following the instructions that you gave them.

Before you fire them: Look closer at the guidance you gave them. Did you lay out your instructions in a way that they can understand? Most of us believe we’re being very clear when, in fact, we’re only communicating 20% of what we need!

If you delegated something that turned out really poorly, this might help you work through it.


You know things aren’t working with your employee when: they seem increasingly bored or disengaged with their work.

Before you fire them: If you’ve been working with them for a while and you feel that it’s appropriate, ask them how things are going. As leaders and bosses, we sometimes forget that our employees have lives outside of work. Maybe your contractor is going through a divorce; maybe her mom is sick; maybe he’s selling his house.  Share what you observe and ask them what they notice about their engagement.

Start by simply asking “How are things going for you?” When we start with an open-ended question, we’re giving people space to tell us as much (or as little) as they’d like.


You know things aren’t working with your employee when: they’re technically following directions and meeting deadlines, but the results just aren’t … very good.

Before you fire them: consider if you’ve really communicated your expectations and goals in the best, most thorough way. Have you shared a clear outcome of what you want the end result to look like?  Have you provided context for how you will use the information or project (how it fits into a larger picture)?

If you want to delegate more effectively, here’s some advice to help you: 4 Tips to Delegate Like a Pro.


Building and right-sizing your team can feel overwhelming, both psychologically and logistically. I’d love to make it easier for you – for free.  I have a special opportunity for business owners and entrepreneurs:

Sign up for my free webinar! Join me 02/22 or 02/23.

“Hire with Wisdom, Fire with Grace” for business owners and entrepreneurs.

We’ll talk through three mindset shifts that will help you change the way you think about your team and finding the people who will help you get where you want to go.

You deserve a team that you love working with. Let me help you build it! Reserve your spot now!