13 June 2023 |

How to say ‘goodbye’

By Gabrielle "GB" Blackwell

One of the toughest, but essential skills a manager needs to master is how to manage an underperformer out of the business. When done well, you’ll:

  • Allow the person exiting to leave with dignity
  • Establish yourself as a trusted partner with the best interests of the business at large in mind
  • Maintain trust & psychological safety with the rest of the team

But when handled poorly, you risk:

  • Burning a bridge with the individual exiting
  • Opening your company up to legal action & heavy severance
  • Sabotaging your relationship with your team


In short, the stakes for managing someone off a team are high. So, I want to give you a playbook to approach it confidently, competently, and in a way that establishes you as a fair and diplomatic leader.

To do this, there are three relationships you’ll need to manage:

  • The relationship with your rep
  • The relationship with your your boss/HR
  • The relationship with your team

Simple, right? 

Let’s start with the rep.

Coaching never stops

Years ago I asked my grandfather, my favorite sales mentor, what the best sales reps did differently. He shared, “The best sales reps are the ones who lead prospective customers to believe the sales rep’s idea is actually the prospective customer’s idea.”

Applying my grandfather’s wisdom to managing out an underperforming rep, the goal of a manager is to get their underperforming rep to see and understand for themselves that exiting the business is the best thing for them

In other words, you’ll want to coach your rep out of the role, rather than force them out of the role.  As part of this coaching, you’ll want to get your rep talking about:

  • How they feel about this role at your company…like how they really really feel
  • If their expectations for the role match up with the reality 
  • What they feel they’d need to do differently to turn around their performance (aka what they’d need to do to make things work)
  • If the work required to turnaround their performance is something they’re willing to commit to

Some reps will tell you right away that they aren’t happy or satisfied with the role or that they’d prefer to do something else. For others, it may take having this coaching conversation more than once for them to accept it’s better to move on from the role on their own terms. 

Once you’ve coached them to be receptive about an employment change, you’ll be better equipped to approach your boss and HR about your proposed change.

🏀 There’s a script I use to have these coaching conversations. Let me know if you’d like me to send it your way! 🏀

Give the right people the heads up

TL;DR – keep your boss and the company out of trouble.

Managers get their bosses in trouble and create risk for the company in two main ways:

  • Lacking documentation of performance related conversations (hint: I’ve covered covering your a** and vetting out the real culprit in previous newsletters)
  • Blindsiding your boss and/or HR about decisions you’ve made about a rep’s employment

By documenting your process, you’ll put yourself in a better position to get HR’s buy-in on moving to exit. And if you’re also coaching your rep to recognize that exiting is a good move for them, you’ll reduce the litigious risk your company may be exposed to when moving a rep’s employment to term.

You’ll also need to keep your boss informed as much as possible. It shows that you have a solid handle on talent management (#buildingconfidence), and it will help your boss get ahead of any headcount and talent acquisition planning.

Assist: If I could shout this through this email I would, but please, for the sake of all that’s holy, partner with HR early and often if you feel like exiting a rep is the best solution.

Your ‘A’ players are watching

Whenever you decide to exit a rep, things can go one of two ways with you team:

  • They’ll understand and rebound 
  • They won’t understand and will disengage

If you go through with an exit and your team perceives your actions as a personal attack against that rep, they’ll quickly lose trust in you as a leader. The remaining reps will begin to wonder if they could be next. In response, you risk having your best people look for other jobs.

This is why having clear expectations around performance and managing your team to those expectations is SO important! 

If everyone knows what the expectations are and whether or not they’re meeting them, it’ll make your life so much easier if you need to make a tough decision about a rep’s employment.

If it’s known that a rep is falling behind for a prolonged period of time, the rest of your team will recognize and respect that you are fulfilling the responsibilities of your role when managing their exit. 

Last piece here on how to manage the team relationship: make sure YOU communicate the change with your team as soon as possible. This way, you can avoid, or at least contain, your reps getting caught up in a rumor mill. 

Assist: Communicate with the team over a live meeting if you’re in office, or over web conferencing for remote and hybrid teams. Where appropriate, offer the impacted rep the opportunity to join the meeting to share the news. Lastly but most importantly, remember to create space for people to ask questions, make comments, and share concerns during the majority of this meeting. It helps big time in addressing any fears or anxieties they may have.

Never underestimate the impact

Managing someone out is a big freaking deal and is a decision that shouldn’t be taken lightly. 

It impacts how a person pays their bills.

It impacts whether someone will have affordable health insurance (if your company has this as a benefit).

And it can impact how psychologically safe the rest of your team feels working for you.

With such a majorly impactful change to a person and team, managers should do their best to exit a rep out with dignity while also being mindful of how this decision affects the rest of the team.