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9 Sales Coaching Tips to Transform & Accelerate Sales

By: Rebecca Herson
November 4, 2021
9 min. read
9 Sales Coaching Tips

Sales coaching is a real challenge for most enterprises, especially as you grow and your sales team expands. Product marketers produce wonderful content describing the product and detailing its features and benefits, but that is often not relevant or useful for sellers on the ground. 

That’s why sales coaching leaders, sales enablement personnel, and sales managers need to take a different approach to preparing sellers to meet their quotas and close deals. 

Here are nine actionable takeaways and valuable advice from two experts in sales coaching, Bryan Neale, founder of Blind Zebra, and Ariel Hitron, CEO of Second Nature. They shared their experience and observations in a recent webinar

Sales Coaching Tips: #1 Build a structured coaching program

It’s crucial to realize that what you’re trying to do with sales coaching is lead behavior change,  Ariel pointed out, and that requires more than intermittent sales training sessions. You need a structured sales coaching program

There’s a lot to say about building this kind of program, but in a nutshell, structured sales coaching requires you to:

  • Define your goal
  • Choose your coaching scenarios
  • Deliver at scale
  • Measure and repeat

Typically, sales leaders want to hit all their sales targets simultaneously, which is great for motivation but challenging for building sales coaching programs. You can’t coach for every goal. 

Then you need to work out which coaching scenarios to use. For example, if your aim is to close larger deals, you might want to coach sales employees to present more big-ticket products, or to handle more C-suite conversations. Think about what your sales rep will need to discover and share in an effective conversation, and use that to build the scenario your seller will need to be coached on. 

We’ll cover delivering at scale, and measure and repeat, in points 3 and 9 below.

Sales Coaching Tips: #2 Focus on the conversation

One of the main causes for the gulf between product marketing content and sales teams is that product marketers tend to think about benefits and features, but sales reps hold conversations in which benefits and features flow together. 

As Bryan said, “the way that [product] knowledge came to me was way, way apart from what reality was. Then the tools and the process we used just did not work because it was so distant from reality.”

Sales coaching has to focus on improving sales reps’ ability to hold an overarching conversation which blends skills and knowledge, features and overcoming objections. In order to make a real difference to sales numbers, you need to improve the conversation.

Sales Coaching Tips: #3 Create a practice culture

Bryan and Ariel agree on the importance of practice. Bryan drew on his experience as an NFL referee, saying “The best players take the most practice reps. They push the rookies aside and the veterans take the reps because the veterans know how important it is to practice.”

Sales teams need to create a practice culture, where people embrace practice. Bryan pointed out that every professional athlete, musician, or artist spends far more time practicing than they do on the real performance or game, but “in selling, we don’t practice the conversation. We don’t practice the art. And it’s less than optimal, to say the least.” 

Some of their suggestions for creating a practice culture included:

  • People have mixed responses to the term “role play”; they suggest replacing it with “practice sessions,” “rehearsals,” “scrimmage,” or “film review.”
  • Build a sales coaching competition, with team leaderboards to help avoid creating a toxic competitive culture.
  • Emulate movie directors and practice from the middle of the “scene,” instead of constantly starting from “Hello.”

Sales Coaching Tips: #4 Offer a safe practice experience 

Practice is the sales rep’s opportunity to get stuck, analyze where they’re struggling, and learn how to deal with it so that they won’t face that kind of embarrassment in real life. But people cringe to see someone else mess up, so it’s vital to offer safe ways for practice to take place. 

Some tactics that Bryan and Ariel use to make practice enjoyable and safe include:

  • Take your turn first, so everyone else can watch you screw up
  • Divide the entire team into “triads,” groups of 3 who rotate the roles of being the buyer, the seller, and the observer. It’s scalable and reduces the anxiety over messing up.
  • Practice with Jenny, Second Nature’s AI-based sales coach, for private sessions and feedback that no one else sees.
  • Use Zoom or your phone’s voice notes function to record yourself in a sales conversation, then listening to it to critique your own performance. 
  • Reward people for getting stuck, to thank them for being real. This could be cash payouts, or cheering each person who messes up because they are working to improve.

Sales Coaching Tips: #5 Adopt data-driven coaching 

Ariel highlighted the importance of “data driven coaching” for connecting your coaching to the needs of each sales person based on facts. It means going into your Salesforce, Hubspot, or other CRM, looking for gaps in the sales pipeline, and identifying where individuals and teams need support. 

If you know what each sales rep is struggling with, you’ll know how to tailor your sales coaching accordingly. Maybe one sales employee is closing small deals because they are only selling a single product and need to be coached in selling more product lines, or another is finding it tough to transition from discovery to demo and needs more guidance about these specific conversations. 

Sales Coaching Tips: #6 Create context for the conversation

Sales coaching role plays only work when there’s a context to the conversation. That means the sales employee and the model “buyer” need to know who the buyer persona is, what came before this conversation, what is the goal, etc. 

It’s a process that takes time, but as Ariel said, “the preparation that you put into coaching is as, or more valuable than, the time that you spend playing the game.” Once you have your conversation guide, you can use it for many practice conversations. 

Bryan suggested that instead of making up “realistic” sales conversation scenarios, you catalog those that arise naturally. Search your sales call recordings to note down real life sales conversation scenarios that your sales employees need to practice. These can also be generated via AI for example using Second Nature’s AI coach, Jenny, who learns through her conversations with reps and can come up with original questions and answers within the guidelines of the persona and desired outcome. 

Sales Coaching Tips: #7 Put on your coaching hat

Bryan shared a concept of the Six Hats of Sales Management. For sales coaching, you need your sales coaching hat, not your sales manager hat or your cheerleader hat, which means focusing on that task alone. “If you’re going to be in a coaching session, it’s a coaching session,” he said. “You’re not talking about pipe, you’re not talking about deal flow, you’re not talking about vision and goals for 2022”

Ariel agreed, saying that one of the biggest mistakes that sales managers make is in inviting a sales employee in for coaching, and then asking about the sales pipeline and suggesting deal strategy. When you wear your sales coaching hat, sales coaching is all you do.

Sales Coaching Tips: #8 Look for early KPIs

You need to set KPIs as part of a structured sales coaching program, but it’s important to remember that different metrics take different periods of time to manifest themselves. For example, if you’re trying to raise the conversion rate for SDRs from connections to booked meetings, you’ll see results quite quickly. But if your goal is to increase total deal sizes for enterprise sales, it’s liable to take 6 months or more. 

In order to demonstrate ROI and drive buy in for your sales coaching plans, you’ll need to find early KPIs. For each goal, think about how long it will take for your sales coaching impact to become apparent, and look for ways to create momentum internally with both leading and lagging indicators

Sales Coaching Tips: #9 Measure sales coaching ROI

Measuring ROI on sales coaching is supremely important if you want to get buy-in from sales executives, but it’s also very challenging. Ariel said the secret is to start with the data and use that to prove the need to coach for specific scenarios. 

The other crucial step is to set a goalpost, like doubling sales for product X or tripling the number of C-level conversations. 

If you end up missing your target, but only raising sales by 50% or 75%, you’ll still have achieved a significant uplift, and you’ll have that figure to prove ROI.

The right tactics can supercharge your sales coaching results

Sales coaching at scale is challenging, but as this advice shows, it’s not impossible. Creating a safe practice culture that focuses on rehearsing conversations, using sales data to develop individualized training and rich practice scenarios, focusing on coaching within a structured program, and measuring and tracking KPIs and ROI all add up to effective sales coaching at scale that drives results. 

See Ariel and Bryan in action in the webinar.

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Rebecca Herson

Rebecca leads marketing at Second Nature