How to Train Salespeople

During my tenure as Mochary Method's Head of Coaching, I’ve learned that managing a coaching team is essentially like managing a sales team. The team amazed me with their ability to deliver value during one of the hardest economies in tech. While coaching is about helping people grow and develop in their roles, I believe sales is about adding value and helping solve a problem. The principles of finding customers who would benefit apply in both cases.

Training a sales team is an ongoing process. Here are the top strategies we learned together as a team:

Create documentation of the entire sales process

It’s important to have a first draft of the entire sales process to describe each touchpoint with the salesperson from the very first call to sending out the invoices. Create examples of everything from a call script to an email template. This way, everyone is on the same page and there is consistency in the sales process.

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Shadowing and reverse-shadowing

The Sales to the Enterprise: how to scale it document describes the importance of shadowing and reverse-shadowing. I would recommend the shadowing period to be 2-4 weeks depending on the complexity of the product. Then another 2-4 weeks of reverse-shadowing. Ideally longer.

In reverse shadowing, give ample written and verbal feedback. More, ask the team permission to keep all feedback open. This way, other salespeople can access your feedback to one person. You can also encourage peer feedback to maximize the learnings of 1 recorded call. 

I give all feedback in this format:

1. 1-5: I rate the call from 1-5. 3 being meeting expectations, 1 being it can’t be any worse, and 5 being it can’t be any better.
2. Like: what I liked about the call
3. Wish that: what I wish to see in the call to get this person to a higher rating

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Create space during meetings for the team to raise their challenges and get support from the group

It’s important to us that the team feels like a cohesive unit, rather than individuals trying to compete with each other. There is so much wisdom and learning that happens when you learn to sell a new product or service. Much of that can be shared with the team outside of the individual silo. Here are the few ways that we’ve created space for the team to learn together:

1. Asked the team to write down their challenges with selling and crowdsource ideas and solutions
2. Asked the team to share how they’re feeling about their pipeline. Sometimes, the team doesn’t need more tactical tips. They just want to know everyone else is also feeling fear, disappointment, nervousness, and so on. This has been one of our most impactful tools.
3. Facilitated Q&A sessions with more seasoned salespeople to gain further insight
4. Ask new salespeople to teach each other a component of the sales process so they can master the subject, and evaluate if they truly understand the concept

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Once the team has learned the documentation perfectly, they may still run into issues with selling. 

One of my teams made a great metaphor. The first stage of learning to sell a new product or service is like learning a new language. That stage is difficult. The second stage can be arguably harder - it’s when you use the new words to start making conversations. Here are the two main things that we leaned on to move through this stage:

1. Update documentation of the sales playbook to include new insights and learnings
2. Go through the entire process with team members 1-1. Find out where the salesperson feels the most discomfort and fear. Ask them to share their thoughts with you. Make them feel heard (Heard:  how to make people feel it) in those thoughts. Then, help them reframe and adapt those points in the process so that the entire process feels authentic to them. 

An example is that a salesperson may not be comfortable with holding the customer accountable for a decision during a call. Upon investigation, what they really feel bad about is appearing as pushy. What would be a way to get an answer from the customer without appearing to be pushy? Well, maybe they could ask the customer for direct feedback on the product or service. When you ask the customer for feedback, you’re also asking them to evaluate the experience to see if they want to work with you. 

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If you’re a manager of a sales team, I would like to encourage you to think about this from the sales team’s perspective. Most people would be learning something new about the process, product, and service. Learning new things can be scary. So as a manager, it’s critical to provide as much clarity and feedback as possible that is customized to the individual’s natural communication style.

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About the Author

Sabrina Wang is a CEO coach for extraordinary leaders of Series A to Unicorn companies. She is a founder, CEO, and operator who brings real-life experiences in building products and scaling revenue into her coaching. She is a writer, creative, and trained meditation teacher.