The coaching gap: Solving sales enablement’s biggest problem – with AI

By Andrew Quinn, Former VP, Sales Productivity and Enablement at HubSpot.

I’ve had a long career in sales. I’ve been a salesperson. I’ve trained salespeople. I’ve managed salespeople. The hardest part of any of those roles was either mastering the key behaviors that would yield sales success or helping others master them. 

There is so much talk about effective coaching as the way to develop sellers into quota crushers. While there is certainly truth to that, what's rarely discussed is the art of practice. 

I have coached thousands of salespeople, and from my experience, what makes an exceptional coach is one who knows how to set the tone for effective practice.

We’ve all heard ‘practice makes perfect’. That’s actually not true. 

‘Perfect practice makes perfect’. If the practice is ineffective, you’re never, ever going to get perfect execution. 

In sales, practice equals roleplay. And (let’s get real here) most sales managers suck at roleplay. 

While there are a lot of reasons for that, one key issue is time.

The only thing we can’t make more of

Around half (47%) of sales managers spend less than 30 minutes per week, per rep coaching their sellers to improve their selling skills and behaviors.

Most managers want to coach more. In my experience working with sales managers to develop their skills, one of the things they typically like about the job is coaching and helping reps practice to get better. They just can’t get to it. 

And when they do manage to get to it, the coaching experience is often rushed and ineffective. Time is just not on their side.

There’s plenty of research on the positive effects of sales coaching. When coaching is consistently defined and implemented, it helps to improve win rates by an average of 11%. Add to that a broader enablement framework (incentive systems, etc.), and win rates jump by 28% on average. 

That’s the difference between a seller being at 90% of their number or consistently at 110% of their number. Think about that for a moment.

The more sellers can practice without the pressure to be perfect, the faster they can develop the skills and habits that drive performance. Giving sellers space to practice without fear of failure accelerates their skill development and leads to more consistent behavior change. 

At the risk of being obnoxious, I’m really good at doing this with sales reps. But that’s the exception. Creating low-pressure roleplay environments has never been a key skill requirement of someone in sales, despite the benefits when it comes to training.

This is where AI roleplay comes in.

New tools for AI sales leaders

AI roleplay can scale the previously unscalable. It gives sellers a low-stakes practice environment that encourages learning through trial and error, which allows them to develop high-performance sales behaviors and improve their selling skills faster and more reliably.

Since the AI roleplay is consistent across all sellers, you also eliminate the variability issues that stem from different sales managers with different levels of coaching effectiveness taking different coaching approaches to develop their reps.

Here’s the thing about live roleplay. For it to work, it requires two people. That is really expensive. If a sales manager or a peer seller has to play the part of the customer in a roleplay with a rep that’s developing their skill, that person playing the customer isn’t doing their work driving to the number. 

AI roleplay eliminates the need for someone to play the role of the customer. Take a moment to think about that.

Sales roleplay in the AI age

UneeQ Sales Trainer is the platform to do this, with key benefits that make it purpose-built for time-poor sales leaders.

It’s customizable, so sales leaders can create scenarios that roleplay sales conversations with their buyers and are aligned with their pipeline and goals.

Salespeople meet with the AI digital humans for face-to-face roleplay, and those AIs act like buyers, simulating conversations, gestures, expressions, and speech. And after each roleplay, sales leaders get ongoing analytics on their reps’ performance, strengths, and weaknesses. 

The key is the roleplay needs to feel real to rep. Almost all face-to-face roleplays between a rep and manager don't feel real. That's why managers and reps really don't like to do them. With UneeQ Sales Trainer the face-to-face roleplay actually feels real which makes the learning stick.

The AIs, unsurprisingly, are also available at any time, anywhere, to the entire workforce. So you don’t have to sync calendars with someone and wait to have a roleplay session later in the week.

I mentioned how exceptional coaches know how to set the tone for effective practice. But how time pressures make these coaches rare. My prediction is that with the latest AI tools, sales leaders will have more resources to coach better, train people better, and win more. 

And perhaps the biggest resource they’ll get is the most precious of all –– time!