21 June 2023 |

Break up the right way

By Gabrielle "GB" Blackwell

It’s very possible that your company cannot and will not be able to meet the expectations or your rep, much in the same way your rep may not or will not meet your expectations. 

If this is the case, it’s probably time to break up say goodbye to this rep. 

But saying goodbye doesn’t mean forcing an exit on someone. 

🚨Hint: the best way to manage a rep out is for them to feel like they made the choice to leave. 

In this resource, I’ll share some conversation flows that will help you coach your rep towards an exit. To make it easier on the eyes, I’ve highlighted and italicized the manager talk tracks.

Let’s dig in…

STEP 1. Ask honest questions

When you realize you have a rep who is either unwilling or unable to perform in the role, you can begin to plant seeds of doubt. 

When: During a 1:1

How: Ask them: 

“How are you feeling about this role?” or “How are you feeling about your experience thus far?”

Most reps will give you a surface level answer. Go deeper. 

“How are you really feeling about things?”

Your rep may know deep down, this isn’t the right role or company for them, but haven’t accepted what that means for them. In asking the question, the rep will begin the process of needing to confront their reality.

This is just the beginning though.

STEP 2: Share observations

If it’s been a couple of weeks and performance hasn’t picked up, have the conversation again.

When: During a 1:1, at least 2 weeks after Conversation #1.

How: Begin with sharing your observations about their performance and ask them again how they’re feeling about the role.

“Hey Pat – I’m seeing your performance hasn’t trended in the right direction, despite coaching and development efforts thus far. I’m concerned about how things are trending right now. How are you feeling about things?”

Listen out for signals of frustration, exasperation, defeat or disinterest. For example:

  • “I thought it was going to be different”
  • “This wasn’t what I was expecting”
  • “I don’t see myself wanting to pursue sales for much longer”

STEP 3: Get real

If your rep is frustrated, exasperated, defeated or disinterested by the role, progress the conversation.

When: This can be a part of the same 1:1 from the last step. If you’re running out of time or see that the rep (or you) may not be in the right mindset for this conversation, you can schedule a follow up 1:1 for the following business day.

How: At this stage, you’ll have two main objectives:

  • Uncover what their expectations were coming into the role
  • Highlight how your organization is not able to meet those expectations

Here are some questions that will help uncover their expectations:

“What led you to get into this role at this company?”

“What motivated you to accept the offer here?”

“What was it about this role that got you excited?”

Listen out for comments like:

  • “I really like the company brand”
  • “I was really bought into the company mission” 
  • “I thought this could be a foot in the door at this company and then I’d move into another role”

STEP 4: Validate concerns

If your rep recognizes this is NOT the role for them, they might be someone who wanted to work for your company…just not in sales. 

When: This can be a part of the same 1:1 from the last step. If you’re running out of time or see that the rep (or you) may not be in the right mindset for this conversation, you can schedule a follow up 1:1 for the following business day.

How: If a rep gives the impression that they’re in the wrong role, you can reply:

“It sounds like you were really excited to join the company because of the mission and/or the opportunity to move into a different role here. But it doesn’t sound like you were or are really excited about the role you’re in at this company. Does that sound like a fair assessment?”

If your rep validates your assessment, remind them they are in a performance based role. If they’d like to move out of the role, they’ll need to perform consistently for whatever period of time is required, per your internal mobility requirements.

“It’s totally fine to have aspirations outside of this role, and, to get to where you want to go at this company, you’ll need to meet performance expectations per our eligibility criteria. Based on your current performance, you still have [X amount of time] in this role before you’ll be able to move into another role. 


How do you feel about that timeline?” 

STEP 5: Walk them through a PIP

🚨Spoiler alert: I think Performance Improvement Plans are a waste of time and I do NOT like them.

When: I’d strongly recommend this be its own separate 1:1 scheduled 1-2 business days from the 1:1 from Step 4.

How: If a rep does NOT want to be in their role, they’ll give the indication that the timeline to move into another role does not work for them. If your rep expresses a disinterest in that timeline, this is where you can offer them another option.

“It doesn’t sound like the timeline is something that is suitable to your best interests, and based on how your performance is trending, there’s a strong likelihood that a performance improvement plan will come into play. 


How do you feel about being on a performance improvement plan?”

At this point, most reps will ask questions about what a performance improvement plan entails. If they do, be wildly transparent about the expectations as well as the consequences if expectations are not met.

“To pass a performance improvement plan, you’ll need to hit [X]% of your quota by [deadline]. There will be daily and weekly expectations you’ll need to meet so I know you’re committed to improving your performance. 

If you do not meet the performance expectation or the daily/weekly expectations, there is the possibility that your employment can be brought to term.”

As you share the expectations of a performance improvement plan, help the rep see how a PIP is not in their best interest.

“Pat, I will say this, I don’t think the performance improvement plan is the best path to go down for you. The only time I’ve seen a performance improvement plan work is when the person really wants to make things work in this role. Based on what you shared with me, it doesn’t sound like that’s the case. It’s also a high stress experience and I don’t want you to go through that if you don’t think this is the right place for you. But I do think there’s a different path.”

Most reps aren’t aware that there are other ways to exit the company on their own terms, despite underperforming. This is where you can highlight how they have a choice in that matter.

STEP 6: Introduce a different option

Tip: Know what support your company offers to help support non-regrettable attrition.

When: I’d strongly recommend this be its own separate 1:1 scheduled 1-2 business days from the 1:1 in Step 5.

How: If your company offers support for exiting employees (check with your HRBP), let your rep know that’s something to explore:

“I know there are ways our company supports employees who are underperforming, if that employee decides leaving is a better option than a performance improvement plan. Is that something you’d like to explore?”

Once your rep is open to exploring other ways to exit the business, meet with your HRBP to identify which options the company can support, i.e. a separation agreement that includes a monetary incentive to render a resignation.

If your company DOES NOT or WILL NOT offer support for exiting employees, you can always have an under the table agreement with your rep:

“Our company does not offer support for employees who are underperforming but don’t want to go down the PIP route. We can, however, go through with the formality of the PIP process, but come up with some kind of exit plan to help with a transition. Is that something you’d be open to discussing?”

An under the table agreement can be simple; the rep should be held to minimum activity expectations as outlined on the PIP, but you realize they’re going to be more focused on landing their next role. This way, the rep (and you) won’t have to stress about the rep passing a PIP.

Wrapping up

It takes a lot of work to accept ‘breaking up’ with work – it is a grieving process. The approach outlined above is meant to help make this work a little easier and way less stressful. 

Will it work on every underperforming rep on your team who you believe should exit? Certainly not. 

But it has worked a lot of the time for me – hopefully it helps you too!