Why Yesware’s Matthew Bellows is on a Mission to Bring Mindfulness to the Workplace

Matthew Bellows has been practicing mindfulness since 1990 — long before he founded Yesware, a provider of software for salespeople, and well before his passion for sales or startups really heated up. And Bellows brings his practice of mindfulness not only to his role as CEO, but to those he employs.

For the uninitiated, mindfulness encourages practitioners to be fully aware and present. And for Bellows it’s a way of understanding how his own thoughts help or hold him back. More importantly, it has helped him introduce a gap between actions and reactions.

“While I can’t control what those around me say or do, I can control how I react,” says Bellows. “Often times, we go through life without any real awareness of how we respond. Instead, we tend to react out of habitual patterns or based on the person or people we’re interacting with. And as the CEO of a company, someone might come to me and say ‘We lost this deal.’ I could react without thinking and say ‘Oh my gosh,’ but that’s a relatively inefficient and ineffective way of leading.”

This ability to pause before speaking is a skill Bellows says we can all work to develop.

“We can actually train ourselves to take feedback and input and pause to consider it for a second so we can respond more skillfully.”

And as CEO of a 100-person company, Bellows has a lot to live up to.

“When it comes to leading Yesware or any company for that matter, CEOs are under a tremendous amount of pressure. There are a lot of expectations, there are a lot of people looking to the CEO for leadership, for guidance, for exemplary behavior. The CEO should serve as the leader of a company’s culture — to show his or her employees how one behaves at that company. Beyond that, employees and potential employees have to decide whether or not this person is worth following. Do the person’s actions match their words?”

As Yesware has grown, Bellows has had to come to terms with the fact that he simply can’t have a personal relationship with every person on the team. In fact, everyone at Yesware isn’t even working under the same roof. With offices in Boston and San Francisco, keeping Yesware’s culture intact has become more important than ever. So Bellows has realized that how he acts in the workplace is at least as important as what he does.

“Am I available? Am I present? Do I live the values of the company? Do I exemplify the kind of place we want to build? Yes or no? And frankly, sometimes the answer is yes, and sometimes it’s not. There are plenty of times when I miss and fall off of the horse. In no way do I have it all figured out…but, I’m trying.”

As amazing as running or working at a startup can be, living and breathing the culture can, at times, be exhausting. Bellows says, “There is a cult of speed in the startup world where you’re always encouraged to be faster and do more. This can be good. At some level you want to grow quickly, you want to push yourself, you want to achieve. But, the breakneck speed of startup life can also encourage a purely reactive approach.”

“In the startup world, we have this amazingly destructive culture of speed.”

Brad Feld, who sits on Yesware’s Board, has encouraged Bellows to take his practice of mindfulness and apply it to the way he runs his business. “In my very first Board meeting with Brad he said ‘Slow down to speed up.’ I thought that was brilliant. What he meant was pause every now and then to consider the next move. He wanted us to think about alternatives, really figure out the right way of accomplishing our goals. And then, having really thought about all the options, go fast.”

Those few words of advice have stuck with Bellows throughout the growth of his company, advice that is very much in keeping with his general approach to mindfulness at work. But what about when it comes to applying his practice to real-world business decisions? What happens then?

Recently a top 10 customer, generating meaningful revenue, came to Bellows with a request. Before they would renew their contract the customer asked Yesware to build an Android version of their product. No one likes receiving customer demands, especially not so late in the sales cycle. Bellows and his team were at a loss. With no plans for an Android app on the roadmap, Yesware was at a cross-roads. “The customer wanted us to commit to building the app in the next two to three months, a tight timeframe for something that wasn’t even on the horizon.”

For Bellows, Yesware’s ingrained culture of mindfulness allowed him and his team to pause and consider how they would approach the request. Where some companies would have immediately responded with a resounding ‘Yes!’ to any ask from a large customer, Yesware took a more thoughtful approach.

There were a few things they considered: How much work building the app would entail, what else it would prevent the team from accomplishing and lastly, how important the items they would have to sacrifice really were. “Ultimately,” says Bellows, “We wondered if other people would buy this product and at the end, we decided that we weren’t able to fulfill the request at that specific time.”

Building out a customer’s last minute request is difficult, but even more difficult perhaps is turning down that customer. “In the end,” says Bellows, “we went back to the customer and said ‘Thank you for your support. You’ve been a wonderful customer. Here is our product roadmap for the next year. As you can see it does not include an Android version of the new mobile application that you requested, but here is what it does include. We want to keep you as a customer, but we’re just not able to do this right now.’”

In the end, the customer appreciated Yesware’s thoughtful approach and transparent response (access to their detailed feature roadmap helped tremendously) and ultimately decided to re-sign their contract.

While mindfulness is clearly ingrained in Yesware’s culture, it’s not something Bellows actively pushes his team members to follow. After all, “Everyone has their own path and their own particular personal journey,” he says. “It would be wrong for me or the company to mandate anything, but we try to provide an environment where mindfulness is supported — they can pursue various practices if they so choose.”

For instance, Yesware’s Boston office has a dedicated room for the practice of yoga or pilates and even brings in a meditation teacher once a week to work with anyone who is interested. The company, like many startups these days, also has an open vacation policy, which Bellows says, “Is meant to allow people to take care of themselves outside of work.” And, oddly enough, employees have opted to use their so-called unlimited vacation to take yoga and meditation retreats so they can maintain and continue these mindfulness practices in and outside of work.

For Bellows, practicing mindfulness at this point is a no-brainer. And he’s glad to see more and more of his team members openly embracing it. At the end of the day, the team is more cohesive, collaborative and better able to pause to think about the impact of their decisions before making a move. And for a startup, especially these days, taking a measured, thoughtful approach is worth its weight in gold. Perhaps we could all learn a little something from Bellows’ ability to think before he acts.