The Ultimate Sales Coaching Playbook: How to Help Reps Become MVPs

Rachel Saltsgaver, Content Manager, Lessonly

A signed football sitting on a desk

So, you want your sales team to always be closing? Then you need to always be coaching. 

Sales coaching matters. Sales leaders need to encourage, empower, and enable their teams with practice, guidance, feedback, tools – everything they need to win deals. 

Don’t believe me? Consider this. Sales teams with effective coaches who dedicate 20 percent or more of their time to team development achieve nearly 17 percent revenue growth and have 75 percent of their reps hit quota on a consistent basis. 

But, if you’re reading this, you’re likely no stranger to the challenges of delivering strategic sales coaching to your team. Luckily, the Lessonly team is here to help simplify sales coaching with a three-part framework that’ll give you ideas and strategies to build a scalable sales coaching model. Let’s dive in. 

Performance Coaching

Performance coaching streamlines the knowledge, tools, and support reps need to close deals and get a little better at their jobs each and every day. Performance coaching is also twofold. It’s about highlighting what reps are doing well and celebrating those things. By doing so, your high performers will stay motivated and seek more opportunities to learn and grow. It’s also about identifying areas for improvement and refining your reps’ sales strategies. So, how can this be done?

First, consider reviewing your reps’ sales pipeline and their conversion rates down the funnel. This will likely help you identify where they are struggling and areas they could use additional performance coaching. 

The best coaches also have transparent and vulnerable conversations with their sales reps to find out where they’re running into roadblocks and challenges. And because these conversations can be difficult and intimidating, it’s important to remember to coach with kindness and empathy. 

Skills Coaching

Skills coaching focuses on interpersonal and tactical skills. This type of coaching maximizes your reps’ talent and helps them develop new skills. And while a good coach encourages their team to improve these skills, a great coach gets in the weeds. In fact, the coaches we admire the most truly help reps excel at the skills they need to build great relationships, level up their performance, and close more details. A few of these skills include:

Delivering effective messaging: Effective sales reps leverage stories and demonstrate credibility. That’s why reps need to know how to best deliver messaging fit for different prospects and scenarios. 

Generating new opportunities: Sales reps need to be able to analyze deals and identify opportunities for upsells or cross-sells. Equip reps with the tools they need to get creative, research effectively, and fill that pipeline.

Forecast effectively: Frequently and accurately forecasting is an extremely important part of a sales rep’s job. Help them understand conversion rates, deal cycles, and more. 

One-on-One Coaching 

One-on-one coaching is all about continuous growth, relationship building, and getting agreements together. This part of coaching brings together performance and skills coaching to nurture relationships that are built on consistency, trust, and feedback. 

While some teams may resort to coaching through informal conversations or in large team settings, we believe the real magic happens during 1:1s. Here’s why. First, 1:1 coaching sessions are consistent in frequency and length, which means reps know that someone is always there to help. Great 1:1s are a great way to show psychological safety and truly listen to your reps. Finally, don’t forget to be your reps’ biggest fan. This will show them that you’re dedicated to helping them develop their skills, overcome challenges, and grow in their career. 

Better Coaching, Better Sales 

At the end of the day, great sales coaching is people-focused not number-obsessed. It’s important to remember to ask questions, provide structure, give feedback, and be human—no matter what type of sales coaching you’re delivering. 

If you’re ready to maximize your sales coaching, Lessonly can help. Check out our free ebook, Major League Sales Coaching for insights and tips from 18 industry experts at places like Salesforce, Drift, Zoom, Salesloft, and more. Or, learn more about Lessonly here

Headshot of Rachel Saltsgaver

Rachel Saltsgaver is the Content Manager at Lessonly. With a blend of both corporate and creative experience, Rachel writes regularly about sales and customer service training and best practices.