How to Coach Underperforming Sales Reps

Coaching underperforming sales reps is one of the biggest challenges that managers face. Too often, managers focus on the symptoms of a representative’s underperformance rather than the root causes. For example, A manager might tell a rep: “you need to prospect more,” when the rep’s problem is not knowing how to prospect effectively in the first place.

Is it possible to coach underperforming sales reps to average or even above-average performance? Yes—but that requires intentionality. To help your team succeed, you need to approach your coaching with an intentional strategy.

1. Ask open-ended questions that allow the sales rep to self-evaluate

Talking to an underperforming sales rep about their performance can be painful. To make the conversation productive, ask questions that provide opportunities for self-reflection. Instead of, “You failed to make quota last quarter,” ask, “What factors do you think impacted your performance last quarter?” Try to drill down on the specifics: “Why do you think that deal last month fell through?”

If the sales rep is resistant to questions, try to rephrase them. If their resistance continues, that gives you key information. KPIs can be a good jumping-off point for questions, but the conversation should go beyond the metrics. You want to deduce the underlying reasons why the sales rep is underperforming.

Listening to a sales representative discuss their performance gives you an opportunity to assess their basic sales knowledge—and their willingness to improve. How well do they grasp basic sales concepts? Do poor organizational skills play a role in their poor performance? Is the sales representative willing to acknowledge their poor performance? Are they genuinely interested in improving?

2. Conduct a comprehensive review of the sales representative’s skills

To understand why a sales rep is underperforming, you should conduct a qualitative analysis of their skills in addition to a quantitative evaluation. Listen in on sales calls, watch them give sales demos, and review their communications with prospects. Provide feedback quickly, when the relevant interaction is still fresh in the sales representative’s memory.

It’s a good practice to be in the habit of checking up on your sales reps regularly. Many sales reps are more nervous when they know their manager is watching, but after multiple observations, they will relax.

Go into your evaluation with an open mind. You might not know the full picture until you are able to observe the rep closely.

3. Identify the root cause of the problem

Once you’ve had a conversation with your sales rep and conducted a comprehensive evaluation of their skills, you should try to deduce the root cause of the problem. There are several common root causes:

  • The sales representative is experiencing a problem outside of work that is impacting their performance.
  • The sales rep struggles with organization and time management skills, which is negatively impacting their ability to complete deals.
  • They lack one or more basic skills that are necessary in sales.
  • They’re disinterested in learning the skills needed to succeed as a salesperson.
  • They might mistakenly believe that they already have the skills to succeed.
  • Now that the problem is clear, you will be able to come up with a personalized plan for improvement.

4. Ask if your management style presents a challenge

As a manager, you need to adapt your management style to individual sales reps. A universal approach to management might be holding some reps back.

Give the representative an opportunity to provide constructive feedback. It helps to phrase the question positively: “Is there anything I could be doing to better support you?” or “Ideally, how would you like to be managed?” Make it clear to the sales rep that you are interested in what they have to say.

If the representative provides a suggestion for change, try to implement it to the extent that is possible. If you can’t provide what they want, explain why.
Even if there isn’t anything about your management style that is hindering the underperforming rep, they will still appreciate you asking the question.

This demonstrates that you are willing to learn and improve.

5. Write down a plan for improvement, including specific milestones

By now, you have a good idea for what needs to happen in order for the rep to improve. Write down a formal plan of action. Include intermediary steps, goals, and a specific timeframe. If you are committing to change your own behavior, or provide extra coaching, make sure that’s in the plan as well.

Schedule check-in meetings for you to discuss the representative’s progress and make adjustments to the plan if necessary. Give the representative a hard copy of the plan and keep one for yourself.

6. Create an after-hours workshop for the underperforming rep

Many underperforming sales reps can flourish with extra-training. In some cases, it’s appropriate to offer additional assistance on a particular skill. Arrange a time for the workshop and design it to their needs.

Even if it’s not practical to organize an after-hours workshop, you should point the representative to additional resources that might be helpful to them. If multiple sales reps are struggling with similar skills, organize a group training session or incorporate the material into one of your existing training sessions.

By taking an individualized approach to an underperforming sales representative, it is possible to help them flourish. To encourage improvement, show your commitment to the representative. It might eventually be necessary to let the rep go—but not until you’ve provided personalized coaching.

James Meincke

James is the Head of Marketing @ Demodesk, the intelligent meeting platform for remote sales. Previously he was the Director of Marketing at CloserIQ.