Reboot Podcast Episode Wisdom for Work #20 – The Art of Firing Well – with Heather Jassy & Ali Schultz

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Wisdom for Work #20 // February 27, 2024


Heather Jassy

Heather Jassy

Executive Coach

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Ali Schultz

Ali Schultz

Co-founder of Reboot, Coach & Facilitator

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Episode Description

If you’re a leader, few things can ruin your day more than needing to fire someone. It’s just plain hard to do, even when you know it’s the right decision.

In this insightful discussion, Ali and fellow coach Heather Jassy share advice for effectively and compassionately handling the challenging task of letting someone go from their job. Heather shares her script for handling the firing process with clarity and empathy, acknowledging the discomfort and awkwardness of such conversations while striving to maintain kindness and professionalism.

This podcast is full of valuable insights and practical strategies for leaders to consider when navigating difficult conversations around performance issues and termination.

Show Highlights

Memorable Quotes:

“If you get to the point where firing people is no big deal to you, you should get out of management business because this is a big deal.” – Heather Jassy

“When you’re firing someone, it should be the end of a series of conversations you’ve been having with someone. Being kind means you sometimes have to be direct and to be clear. Not being clear is not kind.” – Heather Jassy

“I appreciate when managers feel very responsible for creating the best conditions for their team, but we are also managing adults and you can create all the great conditions and sometimes it still doesn’t work out.” – Heather Jassy

“As humans, we tend to make decisions when we get it in a lot of pain. And so, if a situation isn’t on fire, we may tend to wanna leave it a lot longer because otherwise why would you want to introduce intentional stress into the system?” – Heather Jassy

“It’s incredibly fair to say that the moment you enter into this conversation, the person you’re communicating with is pretty much going to be offline in terms of rational brain and it’s going to be full-on big emotions. And so being clear and kind and in a way, brief, is just as kind in a conversation.” – Ali Schultz

“When you decide to fire somebody, you’re choosing to generate a lot of stress for people, primarily for this other person. It’s uncomfortable for you and maybe everyone around this. It’s hard sometimes to want to do that.” – Heather Jassy

“I think something that can be helpful when a manager gets in a very painful place about having to do this is like, okay, remember your job, your responsibility is to this entire group of people, not to a single individual.” – Heather Jassy