If You Build It, They Will Come: Why Building a Coaching Culture Leads to a Better Sales Team


Instant gratification is a dangerous drug. From using Siri to search for answers or getting same-day deliveries through Instacart, we've trained our brains to want everything and want it now. But that's not how sales works. You have to put in the time to reap the rewards—and be willing to change tactics instantly to fit the changing nature of any market or vertical.

I've been a sales leader for years, most recently at Paychex. I came to the company nearly eight years ago to lead a direct sales team in Seattle and was soon promoted to Director, covering multiple states. People think of Paychex as a payroll company, but we do so much more than that: 401k, HR, compliance, you name it. We aim to be a full solutions provider to small business owners and have various products to support them from hire to retire.  

My work used to be face to face, out in the field, taking meetings with referral partners to drive results. And when I was in the office, I prided myself on building a fun, inspirational culture. There were high fives all over the place, fun sales games and from time to time there was even confetti when someone made a big sale. I'd developed a successful career with this approach and planned to stick with it. But when the pandemic hit and prevented my sales reps and me from hitting the road, we had to—forgive me, as no one wants to use this word anymore—pivot.  


The plan was to "lift and shift" people from field sales to a virtual environment, and it was up to me to nurture this virtual sales team. After this call, I turned to my wife and asked, "How am I going to do this?" I wasn't a virtual guy, and many of the managers on my new team, like me, had spent their entire careers in field sales. My wife—a sales leader in her respective field—said, "Do what you do, but do it virtually." As usual, she was right, and I immersed myself in everything virtual, including solutions that would help make the transition easier.

We'd demoed Gong a couple of years ago, and it turned out to be the perfect tool for this moment. In my field days, when I would fly out to meet one or two of my teams, I could check in with 20 people max during that week. With Gong, I could touch all my team members—across the country—in a single day if I wanted. I immediately tapped into my team's pain points in those early days of the shift to this virtual environment. My reps had difficulty keeping clients and prospects on the phone, so in those early days, we focused on opening statements, winning the next 20 seconds and then 20 seconds after that. 

You don't have to be in-person to drive culture and engagement and build success.

That experience taught me how I could use Gong to build processes toward a specific goal. Eventually, I would use Gong to highlight great work and build a culture of coaching, and I learned that you don't have to be in-person to drive culture and engagement and build success.

Lead from the Top Down

I use Gong on my team to drive activity and quality conversations and boost retention. To sales leaders and executives looking at how to roll out a solution like Gong, you should know: It all comes down to how you set the tone. You have to lead from the top. 

I can't believe some leaders tell their teams, "This is what we're doing, good luck," and expect that to work. If the person leading the initiative isn't all in, if they're not building a process to make the change cultural, if they don't explain the why or make it fun, it's never going to go anywhere.

If the person leading the initiative isn't all in, if they're not building a process to make the change cultural, if they don't explain the why or make it fun, it's never going to go anywhere.

I used a few strategies to normalize Gong. First, I held contests along the lines of a prize for the first person to listen to X number of calls or the first person to provide X number of coaching sessions. That made it a fun part of our daily life. I would also mention Gong on national calls: "Here's what I heard on Gong today," or "This isn't something I'm hearing on Gong." That made the platform part of the conversation. I heard that listening to 10 calls is a good target when starting with Gong, so I set my target to listen to 30 calls weekly. That way, when I set a target for my Leaders, they could see I was setting the pace and in the trenches with them. 

These steps matter because you're going to meet some natural resistance. Salespeople and managers will be concerned about micromanagement or having to change how they coach their teams. You have to spend the time on those conversations, explaining the why and what's in it for them. I'm a big believer in leading with vulnerability, so I got on calls and let myself be recorded. I'd show my reps and sales managers the best way to use the tool, using myself as an example.

Some people were also nervous about being recorded, and I'd hear that anxiety in their voices when I listened to calls. When I noticed, I'd pick up the phone and address it immediately. "Hey, I heard your nerves on that call, but you did these two really good things." That reinforcement, paired with the mentality of "Let's go, and go again," ultimately makes people comfortable with the tool. 

In sales, not everyone is going to tell you you're pretty. You must learn to deal with rejection, grind through, and trust the process.

We are all susceptible to common pitfalls, whether we're new reps or tenured salespeople. New salespeople can be impatient for results. In sales, not everyone is going to tell you you're pretty. You must learn to deal with rejection, grind through, and trust the process. Some people, who have had to overcome adversity or have experience in sports, have already learned that. But others will go without a sale for a while and get deflated. That's significant because sales is 99% mental. What I can do with Gong is coach them around gaps they have and introduce them to listening to successful sales calls showing them the way. That teaches a person the necessary skills and shows them that someone else's success can be their success too—if they only stay the course. 

On the other hand, tenured reps can become highly successful in a given lane but then get set in their ways. That leaves them vulnerable when it comes time to adjust their strategy as the landscape changes. For those top reps, I listen to their calls and offer prompts that elevate their skillset and explore new avenues. So I might ask them, "Have you thought about the attachment rate for this product?" or "What industries are buying this product in this vertical? Why aren't we going after those clients?" The point is to teach top reps to look around the corner for future changes.

Put in What You Want to Get Out 

Like anything, you get out of Gong what you put into it. I put in 150%, and I get 150% back. My favorite features include the Deal Board, where I can get into the details of the call and see where a deal might have stalled out by turning each word into searchable data. I can also focus on a specific aspect of calls. I might spend an entire week just listening to openings: the first 30 seconds to a minute. What does a successful opening sound like? I've done the same thing with voicemails. Which voicemails get callbacks? 

I also love the deal insights, which show me various stats. In one instance, I noticed that calls with two contacts had a 50% closing rate. So now, reps must have two contacts on calls. 

Many companies use Gong for revenue forecasting and seeing trends, but I use it to gain data for targeted training around specific details, such as buying signals and objection handling. We listened to hundreds of calls and identified 20 different keywords as buying signals, which some reps might have blown by in the past. 

We have also come to rely on Gong for peer learning, which has led to a coaching culture. We do a podcast highlighting our leading reps, and that includes listening to and dissecting their Gong calls. Reps have become better listeners to their own calls in this process. Instead of running over the client on a call, they're looking to get that fifth-level discovery question. Now, every rep wants to coach one another, and people get excited about listening to one another's calls. There's a correlation between the coaching culture we've created with Gong and driving better results. 

Leveling the Playing Field in a Five-Generation Workforce

At Paychex, like many companies, we want our employees stay with us through their careers and into retirement. We are at a unique moment right now: For the first time, we have five generations in the workforce, from Baby Boomers to Zoomers. How do I coach both a 75-year-old and an 18-year-old? Every generation brings something different to the table and needs something different from me.

The younger generations want to see the career ahead of them. The salary is great, but they have no reason to stay if you're not giving them the water to grow. Gong also levels the playing field across those five generations of workers. No matter a sales rep's age or experience, I can see where they are falling and help them get back up and be ready for next time. 

I increasingly turn to Gong as part of a retention strategy and a way to get people to think about longevity. Gong allows me to show someone at the start of their career a tangible growth trajectory: an honest review of where they are now and where they could be, listening to others as living proof. I can show a new hire that I sent 24 people to our annual conference this year, compared to the eight people I sent last year. All 24 people broke six figures in our compensation plan, and everyone said Gong helped them get to where they are. 

In-the-moment feedback is critical for reps, and it can make the difference between a top sales team and an underperforming one.

I use Gong to develop personal connections, too. When I post content across multiple platforms and channels, I get the most engagement through Gong. And when I hear on a call that a person is frustrated or having a bad day, I can address the issue in real time, rather than waiting for our weekly 1:1. That in-the-moment feedback is critical for reps, and it can make the difference between a top sales team and an underperforming one. It can also be the difference between keeping a good sales rep and saving someone from having a bad run or getting frustrated and wanting to quit. 

Gong has also had an impact on my work-life balance. Before, I used to gain insights through a multitude of manual processes. There are plenty of platforms out there I could use, but everything is on the user. Gong does everything for me, and the mobile app is a life-changer. I have four kids. Instead of being stuck at a desk poring over other platforms, I can get one of the kids to football practice, another to tennis and still provide quality, immediate coaching.

Getting Back to Basics

Over time, my team has evolved into a strategic accounts environment, where we focus on specialty accounts, strategic partnerships, special niches, and other test pilots needed by the company. It's a lot of throwing spaghetti at the wall to see what sticks in different verticals, third-party partnerships, or the specific technology needs of certain industries. Essentially, we operate as a startup within a 50-year-old company, but the basics don't change: drive activity, have quality conversations, present value, and provide our full solution products and services. With Gong, I can ensure my reps are saying the right thing for that particular vertical, even if it's new.

Professional athletes review film after each game as part of their training. Gong is game film for salespeople. You can tell yourself a story in your mind about what went wrong on a call, but you can't run from Gong. It means people have to take an honest look at their performance, and that's how we win.