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How to Build a Culture of Learning and Coaching in Sales [Gary Milwit Q&A]

Feb 24th, 2020

Learning is a core part of how salespeople become successful. They need to be able to learn and apply the right skills and knowledge in order to close more deals. Especially as markets, buyers and methodologies change, sales reps need to be learning continuously to keep their skills sharp and help their companies stay relevant in their industries.

This is exactly the philosophy that Gary Milwit, Executive Director of Learning and Organizational Development at JG Wentworth, believes in. He started his career in sales and then had a stop-over in education before his most recent roles at Stone Street Capital and JG Wentworth (JG Wentworth purchased assets of Stone Street in 2018), where he’s now in charge of the training and preparation of the company’s sales team.

For the latest Q&A in our ongoing blog series, “Sales Enablement Voices,” Milwit shares his thoughts on building a culture of learning in sales, best practices for coaching sales reps and keys to enabling sales managers to succeed.

Previous Sales Enablement Voices Q&As:

In your experience, what are some best practices for developing a culture of learning in sales?

When you want to create a culture of learning, people either want to learn or don’t want to learn because they think they already know. The more confident people are, the more likely they’re going to want to get better. The less confident people are, the more scared they are to learn; they just may not have enough confidence. More people than you think fall into that category, especially in sales.

If you’re patient and build rapport with the sales force, you realize that the key to engaging them is to pay closer attention to them in order to find out what gets them going.

The way you make learning a part of the culture is to find all the positive things people do and exploit those things. When you can do that, you can break down trust barriers. Salespeople are busy, under pressure and quota driven. You have to insert yourself into the culture and provide value, without making them feel like you’re wasting their time. People will engage when something is familiar, if they are curious and if they think they will benefit.

And you can’t tell people they’re wrong. People don’t like how they feel when they are wrong, but they only know they’re wrong when someone tells them. So why not figure out what people are doing right and start building the foundation from that? Salespeople face rejection more than any other profession in the world, so it’s important to identify the good, not the bad.

What lessons have you learned about sales training and coaching?

At Stone Street, we built a culture of training, learning, coaching. Throughout my tenure, we won 5 different awards for coaching and training and became known in our circle as a company that used cutting edge technology for sales enablement.

We coached our sales reps at least twice a week for 45 minutes each time, every week, no matter what. We used call recordings as our “game film” and created a methodology where we could go over calls with more than just one rep and manager. We figured out how to do it with small groups of no more than 10 people with a dedicated head coach and our own coaching room.  

We started by looking for the positives. It didn’t really matter what we did, as long as we did something with the reps that didn’t involve them grinding all day, otherwise they were going to be talking at the water cooler or messing around. It’s just human nature.

We found that if we get reps off the floor twice a week and give them something to think about, discuss, listen and share tips, we were going to win.

Throughout my time at Stone Street, we did 7-8 coaching sessions per month and saw that rep production increased month-over-month-over-month and resulted in better conversion rates. For reps that didn’t attend the coaching sessions, we noticed a lag.

The bottom line was that we found out what worked and didn’t work – and that’s what I’m trying to do now at scale for 5x as many reps. The senior team at JG Wentworth wants to build a bigger, stronger, and faster version of what we did with Stone Street and that is exactly what we are doing right now.

What can a sales enablement professional do to get leaders and managers to buy into sales coaching? 

We’re now using the program we established at Stone Street to train and coach reps at JG Wentworth, with the help of Brainshark. I see firsthand how much the reps appreciate being coached and receiving support from me and my team.

But you have to start where the action is. Our heads of sales are sitting on the floor, on the phone with customers. When I learned more about their day-to-day and what their problems were, the gap was coaching. But instead of asking them to coach, we needed to build an entity for them.

I didn’t change the player personnel or the playbook, I just figured out where the playbook needed to be enhanced.

You can’t force your own process onto the sales force when you’re coaching. You have to work with the talent you have, adapt to the needs of the organization and put reps into a position to succeed.

Why is it so important to enable sales managers to coach?

The pillars of increasing sales production come down to coaches, managers, and enablement tools. The challenge is developing better coaches, while understanding the difference between coaching, training, managing and enabling. In highly competitive markets, those that survive and thrive have one common denominator: they believe in changing culture through learning.

What are your keys to learning in sales?

  1. After survival, learning is the next human need.
  2. Both data and learning can break down business silos. Using data as tool requires education and data and enablement go hand in hand.
  3. Scaling learning requires technology. Use your sales enablement platform as a gateway to integrate technology with sales. Salespeople should be trend setters for companies not laggards.
  4. Learning is the foundation for sales coaching, leadership development, and culture change.
  5. Learning is how to eliminate the comment “all being equal.”