Chapter 7

Sales Skills Exercises

Creating a low-stress practice environment for sales reps.

On the first day of his new job, Connor Fee knew something was wrong.

It was December 2018 and Fee had just joined the marketing-data startup Clearbit to head up go-to-market strategy. The company was the name in sales and marketing data and counted hundreds of high-performing companies, such as Segment, Asana, and Zenefits, as customers. Still, to Fee, something was off—its sales org comprised just three actual sellers.

When he came aboard, it was at a time when demand was ballooning and Clearbit’s sellers were most successful by acting as glorified order-takers.

“The lead would come in and a salesperson would reach out and say, ‘What are you interested in?’” Fee tells 360Learning. “The account executive would demo the product, send over the pricing and say, ‘Call me if you're ready to buy.’”

It was an incredibly efficient process for the sales rep—if one prospect walked away, they had a dozen more waiting to hear back—but it left a lot of money on the table for the company

One of Fee’s first tasks was to evaluate all of Clearbit’s processes, systems, and policies to highlight simple fixes. The assessment confirmed his first-day suspicions: the company needed more sales reps—and lots of them.

“One of my first recommendations was that Clearbit needed five times as many sales reps,” he says. “They simply didn’t have the staff to capitalize on all the demand.”

Clearbit’s executives agreed and soon Fee was working with management to overhaul the company’s sales org.

Within his first year, he had successfully grown Clearbit’s sales team by 5X, which drove both revenue growth and market share. That success was made possible by his brand new training program, one based on a radical theory of learning and innovative teaching methods.

Sales skills training icon


Building a small team is easy. Onboarding just a couple of people at a time allows managers to devote large chunks of their day to one-on-one coaching. But as teams grow, those opportunities are much harder to come by. New employees are more varied, managers have less free time, and there’s more pressure to ramp sales reps faster.

With ambitions to quickly grow Clearbit’s sales org by 5X, Fee was all too aware of the challenges he faced. But after building a small but high-performing marketing team at Nasuni and sales, customer success, and marketing teams at UserVoice, he was more than up to the job. From his experience, he knew that most successful development programs shared three traits. First, they mimicked how people actually learned. Second, they provided low-stress training opportunities. And third, they helped reps practice—a lot.

Sales Reps Training timesplit with 70/20/10

To address the first point, Fee turned to a learning and development model he knew well—the 70:20:10 model. This model says that people develop skills from a wide variety of experiences and not just classroom lessons. “Around 10% comes from learning from management, seminars, and training programs,” he says. “About 20% comes from coaching from peers and 70% comes from actual practice.

Consider a marketing operations manager, who attends a presentation on lead scoring. After the one-hour presentation, they understand the theory behind lead scoring but probably can’t put it into practice. This accounts for around 10% of the skill.

Next, if that individual discusses lead scoring with their peers, they’ll learn how it works in practice, adding another 20% of the skill.

The remaining 70% of development is done by actually using lead scoring in practice. “The manager goes back to their desk and over the course of the week, tries out the technique,” says Fee. “If they fail, they can try again and again and again. By the time they’ve used a skill a fourth or fifth time, it’s locked in as a thing they truly understand and can use regularly.”

For sales reps, this model creates a real challenge. Unlike other professions, sales reps don’t have a safe sandbox practice environment. When they practice, it’s usually on the phone with a real lead—and that’s not conducive to trying new things. “They need to get a fair amount of practice before they ever get on the phone,” Fee says, “because in high-stress environments we default to the thing we know and feel comfortable with.”

Illustration of a Sales Rep being trained on 360Learning platform

Learning in the Classroom

At Clearbit, training starts in the classroom. Every quarter, Fee and his colleagues decide on a new training theme, such as negotiation, automation, or presentation, and arrange an intense long-form kickoff session. The point of these training themes is to increase exposure to a new theme and create a baseline of knowledge for sales reps.

How these longer sessions work depends largely on their content. In some cases, it could be as simple as a sales leader standing in front of a whiteboard. In others, attendees could work through e-learning and interactive quizzes on Clearbit’s learning management system. And when Clearbit’s sellers need to practice or discuss new knowledge, sellers break into small teams to work independently. Usually, simple knowledge-transfer sessions tend towards basic classroom briefings and practical skills skew towards interactive learning or group work.

For the rest of the quarter, Fee and other sales leaders run weekly classroom sessions to break down the quarterly theme into practical subskills. “Once a week on Monday, we review a skill that they should have exposure to,” he says. “We're trying not to teach them anything new but review the core skill we discussed already.”

For instance, if the theme was negotiation, its subskills might be things like active listening, surfacing concerns, and combating anchoring biases. For a knowledge topic like automation, Fee might look at personalization, workflows, and data analysis. For presentations, he could cover structure and writing, body language, and tone of voice.

Although these sessions take place in the classroom, Clearbit’s sales leaders try to inject as much interactive content as possible to help knowledge take root. “We practice the things we just learned about,” he says. “We'll break off into sessions, pull out our cameras, and record each other practicing and iterating on the skills.”

During the weekly sessions, the goal is still knowledge building rather than behavior change. “The training is designed to get you to level one,” Fee says. “Knowledge of a concept is level one. You understand something and can explain it to someone.”

Communal Call Reviews

Once his team members understand a new skill, Fee turns his attention to behavior. Clearbit’s sellers are expected to listen back to their recent calls, pick out some that contain examples of the theme or subskill they’ve learned about recently, and then pull apart their performance.

After they’ve evaluated their own performance, sellers send their calls to their manager for a team call review. Clearbit’s sales managers then pick out a handful of calls and play clippings of audio to small groups so they can review the calls collaboratively.

A quote from Connor Fee reading "More often, the group's knowledge is greater than the manager's knowledge."

The group discusses the calls together—and that’s important because, as Fee says, managers are not perfect. “More often, the group's knowledge is greater than the manager's knowledge,” he says. By opening up criticism to the group, reps can tap into different perspectives and access more varied feedback. Reps also tend to absorb feedback from their peers faster than feedback from their manager. “If I tell you something, you listen a little bit,” explains Fee. “If you tell yourself something, you listen a lot. And if your peers tell you something, you listen a shit load.”

Ring Ring and Repeat Practice

Fee is an engineer by training. It’s why he understands the value of repeated exercises. Consider how engineers learn skills: hunkered down in front of a glowing screen, hammering out thousands of lines of code on a keyboard. Each keystroke reinforces a particular skill and inches its author closer to mastery of C++, Swift, or Python.

Creating a similar environment for his sales reps was a challenge—but Fee knew it would be worth it. What he came up with was a drill called Ring Ring.

Every single Tuesday and Thursday, sales reps gather in small groups to practise their selling skills in rapid cycles. In each group, they rotate roles, with one person as the seller, one as the buyer, and the other as the coach, and for 30 minutes, they roleplay quick two- or three-minute sales conversations, focusing on the week’s subskills. It creates a low-stress environment, where sales reps can experiment and practice, without the fear of losing a sale.

At Clearbit, sales reps make hundreds of mock sales calls a month, practicing cold calls, discovery calls, face-to-face meetings, pitches, and Q&A sessions.

But repetition isn’t the only point of Ring Ring. After each mock sales cycle, Fee encourages his reps to provide feedback to each other, just like how they do in group call reviews. “They give themselves feedback, then their peers give them feedback, and then the manager can give feedback,” he says. It ensures that practice makes perfect, not just permanent.

Initially, Clearbit’s sales reps were reluctant to take on this peer coaching role. “They were too nice to each other,” laughs Fee. “They were like, ‘Oh, that was great. That was great.’” But with a little guidance—Fee encouraged reps to focus their feedback on process and execution, not the seller as a person—reps came round and quickly saw the benefit. “Within a couple of rounds, they all got it,” he says.

Now, when new employees join Clearbit, they join a team dedicated to constant improvement. Almost every day of the week, they see their colleagues doing something to get better—and it rubs off on them.

Illustration of Connor helping Sales Reps to rehearse

It Takes 10,000 Hours

In his book Outliers, author Malcolm Gladwell set out a theory for success loosely based on the work of psychologist, Anders Ericsson. To be great at something, hypothesized Gladwell, people require deliberate practice—and lots of it. In fact, Gladwell claimed that "ten thousand hours is the magic number of greatness."

Fee agrees with Gladwell. “You don't become an expert seller overnight,” he says. “Reps matter. If you go to the gym, you’ve got to put in the reps. It’s the same kind of thing here.”

In the next year, Fee plans to double down on Clearbit’s success, doubling the sales org headcount and bringing in dozens of new sales reps. And he’s confident that he can do it. Because he has a system for actual behavioral change—building knowledge and providing a safe place for practice—he’s confident that he can turn a stream of diverse and inconsistent new employees into a lean, mean, selling machine. “Ultimately, sales is a process, it's like a factory floor,” says Fee. And his conveyor belt is built to build up grade-A sellers.