Why Sales Coaching Matters, Plus 5 Ways to Get Started

Why Sales Coaching Matters, Plus 5 Ways to Get Started
August 28, 2019
sales coaching tips

If you’ve never coached your sales reps, hopefully you’re aware there’s a problem.

Whether it’s missed quotas, inconsistent messaging or lack of sales readiness, there is a multitude of issues that can be improved with effective sales coaching. Of course, implementing an entirely new process can seem daunting. People inherently don’t like change and the excuses for putting coaching on the backburner can seem endless.

Here's a brief overview of what effective coaching looks like in 2019, along with a few accessible ways you can introduce (or reintroduce) coaching to your sales organization.

5 Tips to Improve Your Sales Coaching

  1. Determine where your reps need help
  2. Start small and stay relevant
  3. Create a variety of coaching scenarios
  4. Share it with the class
  5. Actively seek out internal and external resources

What is Sales Coaching?

Sales coaching is the process of evaluating reps’ skills, knowledge and readiness, and providing feedback for continuous improvement in performance.

Research firm CSO Insights offers a more formal definition:

“Sales coaching is a leadership skill that develops each salesperson’s full potential. Sales managers use their domain expertise along with social, communication and questioning skills to facilitate conversations with their team members that allow them to discover areas for improvement and possibilities to break through to new levels of success.”

Coaching is often led by sales managers and facilitated by sales enablement professionals. Many companies provide in-person coaching (i.e. role plays) where managers might define certain scenarios and see how reps handle it in a simulated environment. The manager can then point out the reps’ strengths and areas of improvement and define steps they can take when it’s time to meet with buyers.

Sales coaching tools can aid this process in a big way. This type of technology includes video coaching tools, which allow sales managers and sales enablement professionals to create and assign video coaching activities, where they define a question or situation and ask the rep to record a response via video. From there, the manager can evaluate the response and provide feedback to help reps improve their skills. These tools make the coaching and feedback process virtual, scalable and easy to manage, especially for large or distributed sales teams.

There are other types of coaching tools as well, including technology that tracks and evaluates reps’ meeting and call recordings, sales activities and written materials (such as emails). It’s worth noting that many sales enablement platforms include coaching functionality, such as video coaching activities, AI-powered analysis and manager and peer feedback.

Why is Sales Coaching Important?

Sales coaching is important for many reasons. First, it helps reps continuously improve their performance through feedback, practice and repetition. Next, it helps sales managers improve sales processes, training techniques and pinpoint progress and areas of improvement for their teams. Most importantly, coaching has a huge impact on results. According to CSO Insights, companies with a formal approach to sales coaching experience 10% higher win rates.

If companies don’t have the right approach, the results reflect that. CSO Insights found that an informal or laissez-faire coaching strategy (where the process is up to sales managers alone) can hurt win rates significantly.

Related: Why is Sales Enablement Important? 5 Reasons and Examples

What Does a Sales Coach Do?

While many organizations leave coaching up to sales managers, some hire a dedicated sales coach who is purely focused on helping reps develop the skills needed to have meaningful buyer conversations.

Day-to-day duties of a sales coach include one-on-one coaching sessions, role play sessions, critical feedback provision and deal collaboration. describes her position as that of an influencer, whose job is to help reps improve their approach to selling without controlling how they engage buyers.

How to Get Started with Sales Coaching

1. Determine where reps need the most help

When developing a sales coaching program, it’s important to first determine where sales reps need the most help. To figure this out, try a data-driven approach that compares your team’s performance against benchmarks to spot weaknesses in areas such as pipeline conversion ratios, instead of targeting areas at random. If you purposefully target areas that reps are struggling with, coaching will have a much bigger impact.

2. Start small and stay relevant

Since you’re already walking into a situation where there may be resistance to change, think about how you can gain early momentum.

If you’re doing in-person coaching, have reps act out a simple scenario in a role play, such as recording a voicemail to a prospect and give them feedback on their delivery and messaging. With video coaching tools, you can start even smaller since they’re going to be learning how to use the technology as well. For example, create introductory activities asking reps to respond to a simple question, such as what is your favorite restaurant and why?

By starting small, you can get reps warmed up to the idea of coaching and get them accustomed to different types of coaching – one-on-one with a manager or via a video coaching platform. After they get a few ‘at-bats’ under their belts, the next few coaching activities will be a lot easier.

Quick Tip: Enter every coaching session with an agenda, but also give reps a chance to discuss what’s happening on their calls and where they might be hitting roadblocks.

3. Create a variety of coaching scenarios

There are many stages of the sales cycle and aspects of a deal that cause reps to flex different selling muscles. Sales coaching programs shouldn’t be limited to one flavor, but instead should target different skill sets and levels of experience.  

For example, you may want to coach newer reps on how to deliver an effective elevator pitch, since they’ll still be learning key product and company messaging. Veteran reps might benefit more from being coached on a specific scenario, such as how to cross-sell or upsell one of their existing accounts.

Quick Tip: Try incorporating a round robin-style question-and-answer into your coaching sessions, where each rep focuses on a narrow aspect of the sales process. (Example: What are three questions you could ask of a sales leader whose company just acquired or merged with another firm?).

4. Share it with the class

Coaching shouldn’t just be limited to one-on-one time between the manager and the rep. It really helps to have the whole team involved because reps can learn just as much from each other as they can from you.

Share both the good and the not-so-good responses from coaching activities and have reps give peer feedback. Doing this can not only help weaker reps learn from stronger reps, but it can help any rep learn new pointers on how to improve or take a different approach to find quick wins. Video coaching tools make this process super easy by allowing reps to send recordings to both managers and peers for full-circle feedback. Plus, sales managers can save the best responses and add them to courses or curriculums.

Peer feedback can also help when you have a geographically dispersed sales team. It can form bonds between reps who may never interact on a regular basis and develop a team feeling of working towards a common goal. It also takes some pressure off the sales manager to be the only source of constructive criticism or praise. 

5. Actively seek out internal and external resources

If you are new to coaching or trying to get your program going again, you don’t have to go it alone. Internally, lean on sales managers, sales reps and sales leaders for ideas and inspiration for the types of coaching activities that will be most valuable to the sales team. Externally, there are all kinds of resources such as thought leadership, best practices as well as other sales enablement professionals that are in the same boat!

For more tips on how to solve your coaching challenges, check out this video and eBook: 8 Ways to Use Video Coaching for Team Readiness.