We recently had the pleasure of convening an expert panel to discuss strategies for equipping sales leaders with skills that drive performance every day in our webinar, Stronger Sales With Coaching. Panelists included Jeff Jaworski, Founder of Google’s Award-Winning Sales Coaching Program; Andee Harris, Former CEO at Challenger Inc.; and Mike Lombardi, EdTech Vertical Leader at Amazon Web Services.

Click here to register and view the recording. 

Why sales organizations resist coaching

Most organizations under-utilize coaching because, well, sales team members are busy—and they’re under a lot of pressure to deliver results yesterday. Members of the sales team and managers alike see coaching as an extra. In fact, Andee recounts data from a recent HBR article that found sales reps would only pay a dollar for an hour of their manager’s time.

“They just don’t see value in what their managers are presenting,” says Andee. “Which obviously means we need to train our managers better.”

Sales-oriented individuals are often tactically focused. They want knowledge that fills what they see as immediate gaps, all the more so in a time of rising pressure to more with less.

A mindset shift around coaching for sales 

When done right, however, coaching helps sales manufacture time. It does so by equipping managers with basic coaching toolkits that unlock capabilities that are otherwise left on the table. This means not “defaulting to what you know,” as Jeff puts it, which is simply telling your team what to do. Coaching is a powerful invitation to step back, pause, and move into inquiry mode. This takes the burden off of the manager. No longer do they have to know it all; instead, managers can ask powerful questions that empower their team members to find their own path forward, grow, and be accountable for that growth.

In the end, it was all of a three-minute inquiry-based coaching conversation, yet the deal successfully closed. It’s the biggest in the organization’s history. 

Ultimately, this unlocks more relevant and insightful solutions that the manager, who isn’t immersed in the day-to-day context of a particular deal, can’t have uncovered themselves, no matter how much wisdom and experience they carry. And in the end, it saves them time. 

Mike confirms this given his own experiences recently bringing Hudson’s Spot Coaching for Sales program to his team at AWS. One of his sales team members was stuck negotiating terms for a complex enterprise deal, and expressed a need to “meet in the middle.”

“I just asked him,” says Jeff, who designed and ran the program, “what does the middle look like to you?”

Turning it around like that and approaching with inquiry got the sales team member’s “head spinning” with ideas. Just from the “human to human power of working together,” as Jeff puts it.

In the end, it was all of a three-minute inquiry-based coaching conversation, yet the deal successfully closed. It’s the biggest in the organization’s history. 

And yet, Mike doesn’t view coaching as one and done. The work is ongoing.

“I’ve got my leaders trained to scale it themselves,” says Mike. 

That means doing more than “barking orders” because “that doesn’t scale.” Rather, coaching a team means getting them to think differently. 

While I had an answer, it certainly wasn’t the best one. Going through that process had a better outcome than it would have otherwise. 

Mike recalls when a manager came to him with a problem that Mike thought he had a great solution, but decided to take a coaching approach to the conversation.

“In my head, I thought, I know the answer, it’s this,” he says. “But having gone through the training, I knew I was just there to ask questions and let him solve for this. What ended up happening by me biting my tongue was he actually came up with a solution that I had not thought of, he had not previously thought of, and ultimately was a better idea and outcome than if he had just asked me and I said, “I think we should do this.’ I really thought I had the right answer. While I had an answer, it certainly wasn’t the best one. Going through that process had a better outcome than it would have otherwise.”

Doing so actually delivers the correct solution faster. In this way, training pays dividends across employees and managers as they learn to scale what they learn themselves.

“You’re teaching them a methodology, a way of thinking that empowers them, especially in ambiguous situations,” says Mike. 

What the numbers say

According to Andee, the research confirms the experiences of Mike and other sales and enablement leaders. In her research for her book on how high performers fare in uncertain times, she found that 20% maintain their high performance even during recession.

This is how we enhance sales reps’ capability to manage complexity: not by having all of the answers, but by inquiring their way through the process and providing deep, knowledgeable guidance.

While we may not be in a recession right now, Andee argues that complex B2B and enterprise sales offer similar conditions, plus there are parallels in our current economy to the one in which she conducted her study. There are now on average eleven stakeholders involved for enterprise deals up from six, contributing to longer sales cycles. What’s more, 85% of decisions are actually a “no decision” as opposed to a competitor, and it’s hard to sell against nothing.

What insights, then, can be gleaned from those 20% of high performers who thrive in any condition?

First, there’s recognizing how the buying process has changed. Customers are generally about 57% of the way through the process before they reach out to a rep, and they spend 83% of the process without a sales rep present. That puts sales reps on the back foot and playing catch up from the get-go. It also points to a need to evolve the sales rep role into that of a trusted advisor, the coach that can really listen, inquire, and help the prospect through the process once they finally do pick up the phone. 

This is how we enhance sales reps’ capability to manage complexity: not by having all of the answers, but by inquiring their way through the process and providing deep, knowledgeable guidance.

Driving and measuring impact

The benefits of everyday coaching for sales teams are clear. And yet, we all know the resistance many of us encounter when trying to build buy-in for a coaching program. One webinar attendee asked for terms beyond training to try and build that buy-in, and another asked for tips in setting strategic outcomes. 

Setting strategic outcomes resonated with Jeff, who did exactly this when building buy-in for Google’s Sales Coaching program. Those outcomes will differ across organizations, but three he suggests to measure are meeting effectiveness, deal velocity, and customer satisfaction. The key, however, is to pick a single outcome to focus on. All sales enablement organizations have many goals; focusing on one at a time is how change will happen.

He also emphasized the need to be data driven when building buy-in. 

“What’s the outcome we need to improve? What’s the analogous skill we need in our reps to do that? What’s a repeatable scalable way we can drive that behavior change anchored to an outcome?”

Andee discussed the use of technology to measure effectiveness outside of the typical sales metrics. For instance, she brought up the example of Gong for recording sales calls and analyzing the frequency of use of phrases and techniques explored in the training, then attaching that to close rates.

Jeff similarly recommended the use of AI tools to provide analysis to measure, for instance, how long the sales rep spends listening versus talking. And both Jeff and Michael described how AI-powered tools can be tapped as a great experiential learning tool. 

When initially learning, practicing feedback with a human trainer is important to building those foundational skills. But for behavior formation, technology is really useful in providing the right reinforcement to turn these skills into habits sales reps can use without thinking about them.

For matrixed organizations, it’s important to bring all of the leaders across all areas of ownership into the training process, even if they don’t report to sales, says Mike, to develop a common language and a common culture. That’s how you really drive impact.

The ultimate goal is to build capacity in sales reps so that they can solve challenges more independently and wind up at better solutions.

Building a culture for the long-term

Frontline sales reps are critical to the success of any organization. Managers are critical to their success.

Therefore, “We need to equip them to support our team,” says Mike. And it’s not just a one and done thing. “I’m thinking years out, building and developing a culture of high and sustained achievement…Enterprise sales are very complex. There’s lots of ambiguity, deal sizes are very large. All of that is worth stepping back and saying, ‘Let’s take a distinct approach to how we proceed,’ versus, ‘Hey, we gotta hit numbers and go go go with no plan, no strategy, and no way to tell if it works.’”

The ultimate goal is to build capacity in sales reps so that they can solve challenges more independently and wind up at better solutions.

“Our advice as managers is never as good as we think it is,” Michael says. “We have this assumption that we actually know what the challenge is, but it isn’t as connected as we think.”

Coaching helps managers connect to the real challenge before the problem solving even begins. 

“When we invest in our team,” says Mike, “the return is success beyond all of the metrics a sales organization is measured by.

Learn more about our Spot Coaching for Sales program.