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Kyle Vamvouris
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Min Read
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March 11, 2022

One of your sales reps just missed their quota. Again. Third straight month. You’re shaking your head because you know that things can’t keep going like this. Something needs to change.

But what?

Tough question, and not an easy one to answer. Luckily, I’ve been in your shoes. Over the last several years I’ve spent helping startups build, scale, and optimize their sales teams, this is a situation I’ve run into a lot. And over that time, I’ve found that following this super-simple system can help you handle underperforming sales reps. 

It goes "Diagnosis. Treatment. Decision." 

I'll walk you through each of these steps below. 

Chomping at the bit to get your sales team optimized? Let’s talk. 

Diagnose Your Underperformer

You should be curious about why your sales rep isn’t living up to standards.

It’s not enough to just say “Eh, guess they suck at sales,” and skip straight to firing. Even if you do end up firing them, finding out the reason for their less-than-stellar sales performance can help you prevent similar fumbles in the future. 

Your first action should be to dig into the data.

Analysis of an underperforming rep’s sales data often sheds light on the exact areas of their weakness. Often, it’s not that they are completely incompetent, but that they’re dropping the ball somewhere important.

Knowing where they are failing allows you to focus your sales coaching efforts where they need it most. Let’s say your rep makes the most calls in the office, and gets good prospects on the line, but has a really low conversion rate on those conversations. 

Seeing this pattern in the data tells you all they need is some coaching on how to have effective conversations, and maybe some shadowing with your highest-performing rep. 

Sometimes, the problem causing underperformance is revealed right in the data, but that isn’t always the case. You can’t help an underperforming salesperson turn the tide unless you’ve identified the true underlying problem in the sales process. In my experience, there are several common reasons for persistent underperformance:

They Don’t Have The Skills 

It’s pretty clear when a rep doesn’t have the skills they need - active listening, organization, negotiation, authenticity, reliability, and, let’s face it, charisma. It’s up to you, the sales manager, to determine if they have the capability to learn those sales skills and to do it quickly enough to help you take off. 

They Don’t Know What To Do 

It’s possible that your salesperson is just a little lost. They might be unsure about which accounts to pursue or how to effectively communicate the value proposition of your product when they’re talking with a client. 

Not knowing exactly what to do is one of the most common reasons for underperformance. Thankfully, it’s also one of the most easily resolved.

They Aren’t Putting In The Effort 

Let’s all be honest, sales is hard work. Even in the sophisticated world of account-based sales, there’s still a lot of grind. Sometimes, poor sales performance comes down to the fact that a rep is wasting all their time on activities (sales-oriented or otherwise) that just don’t generate you sales. 

Their Morale Is Low 

A salesperson might be in the wrong headspace for any number of reasons, work-related or personal. Their low morale might be acute or chronic, static or growing worse. This is an issue with the potential for complexity. 

You can’t begin to solve this problem without fostering an environment that allows for open communication. 

Strategies For Improving An Individual’s Performance 

No point in dilly-dallying. Once you’ve determined the root cause of your rep’s underperformance, you can pick the right strategy to bring about a swift solution. 

While every company’s situation varies in its own way, I’ve established several generalized go-to strategies for turning around a serious underperformer. 

Coach With Care 

One-on-one attention and direction isn’t a cure-all. You can’t coach away every issue related to underperformance. However, it is exceptionally effective when you’ve identified an area of weakness that is stopping your rep from succeeding. 

For example, if I notice a rep is struggling in demo meetings, I’ll sit down with them and do a mock demo. During that meeting, we’ll listen to recordings of their sales calls. Any time the rep responds to something their prospect said, I’ll pause and ask them to think about all the possible outcomes their responses might generate. This sort of reflection forces them to consider where their responses may or may not lead the sales call - which ultimately makes them more intentional and effective at leading it towards a positive outcome. 

Sales coaching requires some self-reflection as well. If you aren’t strong enough in a skill to coach someone to your level (and beyond), try to find alternative resources (like sales management consultants) that instill the skills you want.

Share Top-Performing Practices 

Just as you have an underperformer, you probably have someone who always kills it. Shamelessly steal their best practices and share them with your underperformer. Hopefully, you have some concrete processes to copy+paste into your underperformer’s daily routine.

For example, I often have my sales reps create daily schedules that show me what they’re generally working on, and when. Without an exact schedule, they’re required to follow, everyone ends up doing things slightly differently. Some of those end up being more effective than others, regardless of who the rep is. Take a look at what your top performers are doing - and what their daily breakdown looks like. Then have your underperforming rep organize their day the same way. 

So sure, everyone has their own way of doing things, but when the chips are down, marching an underperformer along in the footsteps of your top sales rep is often a pretty effective path. 

Break Down Goals

Massive long-term benchmarks, quotas or goals have been known to throw sales reps off their game. 

Breaking down large organizational goals into smaller, more achievable, more familiar tasks can help an overwhelmed underperforming rep claw their way out of a slump.
For example, let’s say my rep is clearly overwhelmed by the requirement to generate 20 demos in a month. I’ll “disguise” that big quota as something they’re way more comfortable with - let’s say, 3 good conversations a day. I tell them in order for it to be a “good” conversation, they have to learn three things about what the customer is going through. 

I know that 3 good phone calls per day will definitely translate into 20 demos by the end of the month, even with a lower close rate. And now my sales rep is focused on a specific, actionable, and achievable goal. 

It’s a clever little “Jedi mind trick” to circumvent the stagnation that big, unattainable quotas often impose.

Refocusing Your Rep

Here are a couple of things to keep in mind when you’re taking on a poor performer: 

  • Coaching takes a significant amount of time. 
  • There’s more than one way to contribute to a successful sale. 

In the time that it takes you to train and strengthen your underperformer’s weakest skills, you can also be cultivating their superpowers. 

The idea is to shift their focus to the actions they are most successful at and coach them in areas where they show weakness. 

If they’re great at email prospecting and terrible on the phone, you can have them focus on proportionally more emailing prospecting to refine their already-solid tactics. At the same time, you can be coaching them on phone skills, and shoring up this weakness. 

Maybe they’ll never be as good as your top performer on a call, but they might be able to achieve the same sales numbers through slightly different methods.

Double Down On Communication 

Underperformance always has a reason. If the cause for your sales rep’s poor results isn’t easily identifiable and resolvable through other means, good communication is a failsafe. 

Here’s how you want to use the power of communication:

Open Lines 

Foster an environment where sales reps feel comfortable speaking to you about their thoughts and concerns. Open, forthright conversations help improve the performance of your whole sales operation. 

Fully Realized Feedback 

 Always provide specific, actionable feedback, both positive and negative. Explain the longer-term impacts and the deeper reasons why something was a success or failure. If your feedback doesn’t also offer logical information, it will be much less impactful. 


It’s more than just good feedback. Celebrating a win builds reward pathways in your rep’s brain. Like a drug. Celebrating wins makes successes more meaningful and incentivizes your reps to pursue that feeling. It’s also a core strategy of motivating your sales team as a whole.

Create Structured Onboarding & Sales Training 

Underperformance is a natural result of poor preparation, often because there hasn’t been a structured system of onboarding and training set up in the first place. 

I know how it is. The heady first days of a startup when you are winging almost literally every aspect of the business. Been there, done that... 

Usually, there comes a point when you realize “Oof, yeah, would've been nice if we set that up days ago…” If you’ve gotten to that point, here’s the simple yet effective process I generally use when I’m bringing new sales reps up to speed: 


Day 1 - Company overview, hardware setup, HR stuff, and a thorough review of the competitive landscape.

Day 2 - Prospecting strategy, cold call overview, shadowing SDR calls.

Day 3 - Cold call role-playing, cold calling (yes, I put my SDRs on the phones on day 3).

Day 4 - Day 3 learning, cold call role-playing, cold calling.

Day 5 - Day 4 learning, cold call role-playing, cold calling.

Sales Training: 

Onboarding takes up the first week, after which, reps should begin a formal training process that consists of three tiers.

Outbound Prospecting 101 - 3 days a week for 3 months

Intermediate Prospecting - 2 days a week for 3 months

Advanced Prospecting - 1 day of training, 1 day of teaching prospecting 101 for three months.

Obviously, this is intended to be applied to new hires. But if you’ve never trained an underperformer, it can be hard to blame them if they’re a little lost. You can modify this schedule a little bit and essentially use it to re-train your underperformer.  

Tough Decision Time

Termination is very rarely a good time. It’s often complicated by the fact that many startups have small sales teams, and intense, personal environments. Your underperformer at work may be your best friend outside the office. 

So I get it. Firing someone is hard. Knowing if you should fire them can be even harder. Having run this gauntlet a few times, I’ve learned a few things that make it easier.

When Is It Time for Termination?

The decision to fire an underperformer shouldn’t be made lightly, but when you reach that conclusion, it should be carried out without hesitation. Easy to say, but not so easy to do. So here’s the ruleset I’ve made for myself: 

  1. Put a lot of energy into helping a struggling rep improve.
  2. If they do not take action on the support and continue to perform poorly, let them go.
  3. If they do take action on my support, and still perform poorly, I try to get them a different role at the company.  Jim Collins, in his book Good to Great, says "put the right person in the right seat." If you have a great employee who is struggling in the role, you should find the right role for them.

The really important thing is not to hesitate. As painful as it is to admit, that underperformer is negatively impacting your other team members, and your whole business. As a sales leader, you have a responsibility to take this in hand.  

Taking Ownership

Once, when I led a sales team, I let an underperforming SDR stick around for much longer than I should have. I really liked them as a person, and it was hard to confront them. Finally, they admitted to me that they weren’t invested because they felt they were “better than the job,” because it was a step down from their last position. On reflection, I determined that I enabled their toxic belief. 

The truth is, at the time I felt that they had more experience than me. My own insecurities were exposed through my actions. I didn't hold them accountable, I didn't effectively communicate my concerns, and frankly… I didn't do a great job as their leader.

That experience, as much as it sucked, taught me the full extent of my responsibility as a sales and business leader. 

I learned that there will always be things outside of your control, it's inevitable. It’s easy to point fingers, but as the leader of the sales team, either in title or in spirit, you must take ownership of everything and focus your energy on what’s in your control. Underperformance, like it or not, is your domain. 

I took ownership after that, and I never let it happen again. 


Here’s some good news to end this heavy topic: The most difficult step is over. 

Sure, sure, firing might still be more painful. But now you’ve taken action to deal with your underperforming rep, the process has begun. You’ve got a plan. You’ve got the next steps. 

1st: Diagnose the issue by diving into the metrics and examining common causes. 

2nd: Help your rep improve their performance.

3rd: Make the right call on termination.

Are you ready for sales meetings to get a lot less tense? Get out there and tackle your underperformer (not literally!)

Want to dive right in? Vouris can help. We partner with early-stage startups to build, scale, and optimize their sales teams to drive rapid and sustainable growth. In a quick call we can evaluate your sales operations and provide key insights for improving your team.

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