Chapter 9

Sales Coaching

Break decade-long selling habits with regular coaching.

In January 2019, on his first day as director of sales for e-contract business Proposify, Daniel Hebert could tell the company’s sales team was in trouble. Proposify was spending thousands of dollars on external sales training but no one was actually using it. Instead, they used sales methodologies from old jobs or designed their own ad hoc approach.

It was a daunting workplace for a new director of sales to walk into and no one would have blamed Hebert if he had turned around and marched straight back out the door. But he didn’t do that. Instead, Hebert methodically pulled apart the Proposify’s sales training program and rebuilt it around one-to-one coaching. In doing so, he improved Proposify’s average deal size from $1,989 to more than $7,000.

A quote from Daniel Hebert reading "Proposify was spending thousands of dollars on external sales training but no one was actually using it. Instead, they used sales methodologies from old jobs or designed their own ad hoc approach."

Have a Sales Methodology? Use It.

Long before Hebert joined Proposify, the sales org had signed up to the Sandler Sales Methodology, which teaches a way of selling based on the psychology of human behavior. The method requires reps to ask the right questions for each individual prospect rather than providing standardized answers. As part of the deal, a Sandler trainer visited the Proposify office every month to deliver a refresher on the sales methodology, run some roleplays, and answer questions. But outside of those monthly visits, Proposify’s reps didn’t see Sandler’s trainer at all.

But despite the significant investment of both time and money, no one was using the system. And as Hebert told 360Learning, “A sales methodology is 100% useless unless you implement it.”

When Hebert started at Proposify, he started by looking at how the system was originally implemented. What he discovered was that it wasn’t. The systems Proposify’s sales team used had not the slightest hint of the Sandler methodology in them. With system and methodology totally separate, Hebert wasn’t at all surprised that his sales reps weren’t using it. With reps using a strange medley of selling methodologies, Hebert says discounting was rife. Of all the deals his reps pushed over the line, more than 90% were discounted, leaving thousands of dollars on the table.

The first thing Hebert did was to bake the methodology into Proposify’s systems and tools. “We rebuilt our CRM using the actual elements of the discovery format from Sandler,” explained Hebert, recalling one of the changes he made. “Now, when reps are logging notes in the CRM, they’re actually logging them with Sandler in mind.” After setting his employees loose with their new CRM, Hebert was confident that his sales reps would start using it—but they didn’t.

Reps still went off-script, implementing their own ideas and strategies. It was then that Hebert realized he was trying to break decade-long habits and he immediately understood that gentle nudges weren’t going to cut it.

A quote from Daniel Hebert reading "A sales methodology is 100% useless unless you implement it."

Same Time, Every Week

To understand the challenge Hebert faced, we need to understand where he came from. Hebert studied business at college and landed a marketing role when he graduated. For five years, he climbed the marketing ladder, working, most recently, as marketing manager at customer success platform, LevelJump. When he arrived at Proposify in early-2019, Hebert didn’t have the same comprehensive sales background as other sales leaders.

To compensate, Hebert lived in sales management books, learning everything he could about leading high-performance sales teams. One of those books was ProActive Sales Management by William Miller, where he learned about the value of regular one-on-one coaching.

It was like a lightbulb going off in his head. Just changing some fields in a CRM wasn’t going to break the decade-long selling habits of his reps—but regular coaching might.

Using the book as a framework, Hebert designed a three-part coaching scorecard, covering each rep’s sales results, sales competencies, and sales activities. “The formula is skills times execution equals results,” Hebert explained. “If your results are down, it's probably because you haven’t learned the necessary skills yet or you're just not doing enough of the right things.”

At the start of each month, Hebert challenged his reps to evaluate their performance, rating each field on a scale of one to four, one being unacceptable and four being exceeds expectations. The following week, Hebert added his assessment next to theirs. The scorecard format created a quantifiable performance record, which tied into adherence to the Sandler process. On a scale of one to four, how well did a prospect establish good rapport with their prospect? How effective were their questions at uncovering their prospect’s pain points? Did their fulfillment presentation include all the necessary information?

Hebert’s regular coaching quickly aligned his reps with the methodology—but that was just the start.

After solidifying the sales org’s processes, Hebert implemented a Plan, Do, Check, Act framework to shore up his team’s wider sales performance. After each coaching session, Hebert worked with reps to identify key areas they needed to improve on. “There are goals that are specific to skill development,” Hebert explained. “Or they could be activity goals. If time management is a problem, we can say, ‘Hey, are you scheduling your day correctly?’” Once Hebert landed on a goal, he worked with each rep to work how they were going to achieve it. “What are the potential solutions they could put in place?” Hebert mused. “What are they actually committing to getting done?” Finally, the following week, Hebert reviewed the plan and, together with his rep, decided whether or not they’d achieved their goals.

Each coaching session was tailored to the individual, Hebert said. It zoomed in on their individual strengths and weaknesses, and created a clear roadmap for improvement. From the outside, the coaching process looks simple and effective—but Hebert is careful to temper expectations.

Effective coaching, says Hebert, is difficult to get right. Tracking quantitative sales metrics will give you an overview of if the whole system is working but the most valuable information comes from qualitative conversations and interactions. “[The most useful information] is stuff like behavior change and attitude,” Hebert says. “Are people completing their coaching plans? Are they implementing action items? Can you see the change in customer conversations?”

Illustration of Daniel Hebert coaching the whole team of reps

Coaching the coaches

Often, people treat management as the natural extension of individual work. Someone is a great sales rep so they’ll make a great sales manager—or so the story goes. In reality, managers usually require a completely different set of skills than the employees they oversee.

Consider the skills one of Hebert’s sales reps requires to excel in their role: prospecting, relationship building, negotiation, and persuasion. Now consider some of the skills Hebert needs himself: strategic thinking, delegation, planning, and stakeholder management. As you can see, the two roles demand almost entirely different skills.

And that, says Hebert, makes coaching very difficult because in most sales teams, no one teaches sales managers how to coach their direct reports. Hebert recalled one sales manager who thought she was coaching effectively. But when Hebert looked more closely, he discovered the exact opposite. “Her coaching was just a pipeline review once a month,” Hebert says. “She wasn’t recording calls, she wasn’t doing deal reviews.”

With managers failing to deliver effective coaching, Hebert went back to what had worked for his sales reps. He made a copy of the sales rep scorecard and adapted the metrics for managers. Then he began inviting managers to regular coaching sessions.

Hebert recalled a business development representative (BDR) manager who had never coached anyone before. In fact, he had never managed anyone before. Hebert arranged to meet the BDR manager once every other week and designed a coaching scorecard for his unique circumstances. “Being as BDR manager, what are the results that you need to drive?” Hebert asked of his new trainee. “What are the skills that are going to get you there? What are the things that you need to do in order for your team to drive those results?” As with his reps, once Hebert had set the goal, he helped the inexperienced manager work out how to get there.

The coaching—and, indeed, the experience of being coached—helped develop the skills the BDR manager needed to excel in his role. After a few months, he was delivering outstanding coaching to his direct reports.

Building a self-coaching culture

Early on in his tenure at Proposify, Hebert recognized that managers typically formed the bottleneck in the coaching process. If it took one hour to plan, conduct, and record a coaching session, each manager was limited to just eight coaching sessions a day—less if they wanted to stop for lunch or take a break. Worse, traditional coaching created a dependency on each coach. If a manager wasn’t there, the coaching simply couldn’t take place. “What happens if I want to go on vacation for a couple of weeks or get hit by a bus?” Hebert said. “If I'm the bottleneck for someone to get coached, I didn't do my job well in designing the system.”

A quote from Daniel Hebert reading "If I'm the bottleneck for someone to get coached, I didn't do my job well in designing the system."

Hebert wanted to build a self-sustaining, peer coaching culture that didn’t just rely on a handful of senior managers. He wanted sales reps to coach sales reps and BDRs to coach BDRs. But he knew that would be a challenge. Employees who are used to hierarchical organizations typically don't like giving or receiving feedback from their peers. To get around this reluctance, Hebert cultivated Proposify’s self coaching culture in a very unorthodox way.

Hebert’s first step was starting a monthly book club for the sales team. Every month, everybody would read the same book and then they would discuss it over lunch. The informal event put all the sales reps on the same level and encouraged them to discuss each other’s ideas. If somebody thought a particular interpretation of a book was wrong, they were encouraged to challenge it and explore their disagreement. Hebert’s book club quickly taught his reps how to interact with one another. His next idea would transport those skills to a sales setting.

After the book club was running smoothly, Hebert began arranging group sales call reviews. “I would buy lunch for my team and we would all listen to recorded calls on Chorus,” Hebert said. “We would just listen to it as a team and talk about what happened.” The sales rep who originally took the call was usually in the group so everyone got used to hearing feedback on their performance in public. And slowly Hebert shifted the perception of public feedback from shame or ridicule to constructive improvement.

When Hebert began asking sales reps to give feedback on their colleagues calls, there was no push back at all. “Now, it’s happening naturally,” said Hebert. “Everybody is talking to each other, sharing ideas, listening to calls, and giving feedback.”

He recalled two reps that he followed over the summer. A couple times a week, they would meet up with a handful of good and bad recorded calls, and listen through them together. “They would say, ‘Hey, you asked a really good question here’ or ‘Hey, was there an opportunity for you to dig a little bit deeper on this type of pain question?’” Hebert said. For as long as Hebert watched the pair of sales reps, there was no input from any manager—yet both were improving their performance every single week.

Seeing instances like these bolstered Hebert’s belief in peer coaching. Instead of relying on a handful of managers to deliver coaching, he had proved that his sales team could coach itself, free from the bottlenecks of managers.

Since introducing his new coaching program, Proposify’s sales team has shifted up a gear. Across his entire team, Proposify’s average deal size increased by more than 3X rates and, at the same time, the sales cycle fell from 107 days to just 36. Anecdotally, Hebert has seen a significant improvement, too. Day by day, his reps are more willing to solicit and accept feedback from one another. Every week, Hebert says he sees more self-directed peer coaching sessions popping up in company meeting rooms, break out areas, and cafes.

Going forward, Hebert said he plans to double down on what’s working. He wants more sales professions training each other, sharing their knowledge and strengthening the sales org. “If we add more people, our network of peer learning is just gonna get way bigger,” Hebert said. “Way beyond what I can ever coach.”