5 Lessons I Learned About Sales Coaching from 2 Phenomenal Managers

How do you coach and develop a sales team? 

Well, isn’t this the million-dollar question that every sales leader would love to know the answer to? If focusing on pipeline and hitting quarterly goals are two pieces of your job description, investing in your people, refining their skill set, and enabling them to thrive in their roles are probably also in there. And these latter goals are arguably more challenging. 

As someone who has never been a sales leader, I’m not here to share my personal experience or be a professional sales coach. Instead, I’ll tell you the story of a girl who got into sales right out of college with absolutely no selling experience, but had two phenomenal sales managers who coached her to be the rep she is today. (Hint: It’s me.)

Here are five sales coaching best practices that my two sales managers, Kyle and Kenzie, applied beautifully as they led me. Both of them have different sales coaching styles, and both are phenomenal managers.

1. Prioritize individual sales coaching.

Kyle was the absolute master of this. His sales team consisted of newbies like myself, experienced sales reps, and individuals with 3+ years of work experience, but who were new to sales. All of us needed different types of support from him, and he took the time to individualize our weekly 1:1’s to focus on our specific needs. One rep could need his help role-playing for a job interview to become an account executive. One rep might’ve asked for his help with messaging and prospecting. And for me, being the newbie I was when he managed me, needed his help simply understanding general business acumen and our product. He adapted to each of our needs, and we all appreciated him so much because of this.

2. Coach based on your target market.

I recently switched from a commercial sales role to an enterprise sales role, meaning that all of my accounts have 2,500+ employees. Enterprise businesses think differently, prioritize different metrics, and function in different ways, and I needed help from Kenzie with enterprise sales training. Kenzie helped me feel more confident with my messaging when reaching out to larger companies, which is what I needed to become a successful enterprise sales rep. 

3. Get it done.

Something I admire a ton about Kenzie as my current manager is her ability to simply get things done. If there’s a question I have or a resource I need, she gets it done ASAP and will always go to bat for her team. Players go to their coaches when they need advice or help, and Kenzie does this just as well as the best coaches in sports.

4. Have difficult conversations.

This is a tricky one, but it’s reality. When numbers are low or quota is missed consecutively, a difficult conversation is sometimes needed to light a spark of energy and encouragement in sales reps. Along with this comes the need to provide coaching for sales performance. When I was having a difficult quarter, I remember Kyle having a difficult conversation with me and getting to the source of the issue to help find a solution. Was the issue my messaging? My prospecting? My cold calling? Kyle always found the root of the problem and then provided sales coaching to help me improve the following quarter. 

5. Practice makes progress. 

Like any athlete, you have to practice to become the best sales rep. Michael Jordan didn’t just wake up as the best basketball player: He practiced. One thing Kenzie and Kyle both weave into their coaching strategies is bi-weekly practice meetings. Every week, we fill out a form to identify where it is that we need practice. Then, they decide what the practice topic will be on. Getting together as a team twice a month and practicing our skills helps us to become stronger sales reps. We usually follow up our practice with a lesson within Lessonly on whatever topic we covered in practice. If we practiced cold calling that day, then there’s typically a lesson on cold calling due the following week. Investing in a sales training software where reps have a place to go to practice on their own, make mistakes, fix them, and receive coaching from their managers is, in my opinion, crucial to the success of any sales rep.

So, why is sales coaching important? 

Because just like in sports, a sales coach is someone who leads and motivates the team, who calls the shots, and who players go to for questions, answers, and help. I hope these sales coaching techniques help you to think of new ways to be the leader and coach your team needs to succeed in 2020.

Ready to coach like never before with Lessonly?

Sales teams move fast and sales enablement should, too. With Lessonly, reps learn, practice, perform, and ultimately do Better Work. We’d love to show you more right here or in any of the tiles below!

Also, check out our most recent playbook—Major Leagues Sales Coaching—for inside coaching secrets from 18 world-class sales leaders at places like Drift, Salesforce, SalesLoft, and Zoom.

Remote Training 101: The Value of Blended Learning In A Remote Environment
Four lenses that are helping me

Like what you see? Learn more below.