woman holding a 'like a boss' mug
PHOTO: Brooke Lark

Lately, we’ve been hearing a lot about how working parents feel challenged to balance their duel careers, only one of which pays the bills. I have my fair share of stories about coexisting as a mother and an executive, like when I had to rush to the airport for an offsite the afternoon my son was discharged from the hospital, or that time when I was still nursing, and asking receptionists in London about where to store a very important freezer bag during daytime meetings. 

Being a working parent, though, is not all about compromises and struggles. I’ve found that motherhood has made me better at not just prioritizing my time, but also in how I manage myself and other people.

Leadership = Creating Environments for People to Thrive

Before my son arrived, I was a good boss to high performers, but incredibly hard on those who didn’t meet my expectations. I was intolerant of learning, of mistakes and, worse, I felt this approach was justified.

But that changed when my son was born. Motherhood made me understand in a visceral way how much I want my son to feel safe, loved and to flourish, and that the best way to help someone learn and shape their behavior is to coach and inspire them — not find them wanting on an unforgiving measuring stick.

If you agree that good parenting is about ensuring that a child’s wholeness is supported as they learn and grow, I’d argue good leadership starts with that same humane orientation. A vital part of leadership is a focus on creating an environment that allows fundamentally capable humans to navigate business conditions, organizational structures and their blind spots so that the individual can thrive.

I’m not suggesting we encourage helicopter-leadership. Rather, we should respect our employees by first making sure we put capable people into the right roles (this is hard!), and then set up systems and processes for them to develop and grow (also not easy!). At Capterra, we’ve grown from an office of 45 to nearly three times that size in less than three years. We’re finding ways to develop talent and get to know each other. Our programs are still early in the process but I’m hopeful we’re on target.

Related Article: 2 Characteristics of Effective Leaders: Authenticity and Integrity

Involving Employees in Shaping the Workplace

Foundational for us is our monthly all-hands meeting. Like many other companies, we get together to welcome new people, celebrate anniversaries and hear about how we’re doing as a business. But unlike many other organizations, we also spend time talking frankly and openly about what we aren’t (yet) doing well — what we’re learning, and how we’re developing new processes to assist our continuous growth.

There’s also time for an anonymous Q&A session, where I will answer any and all questions that are submitted by the organization. These range from “Can we add another water dispenser machine by the bathroom?” to “I feel like we’re all getting crushed by meetings. Are there any plans to address how we can reduce the number of meetings overall, as well as make them shorter and more meaningful?”

Recently, we’ve added a twist: immediately following All Hands, we send out an anonymous survey to understand what worked, what didn’t and what ideas people have for next time. In the year that I’ve been here, our all-hands have become shorter, more focused and more satisfying because they have been shaped by the employees, themselves.

In addition to All Hands, we host an hour-long get-together every other month called “Unprofessional Development.” Attendance is voluntary, but I’d say half of our company attends. Four staff members volunteer to each prepare a 15-minute presentation on any topic (within reason, of course). We allow it to be about any topic because the point isn’t necessarily what’s being said, but how it’s being said. It gives our employees a chance to refine their presentation skills — and it’s a safe place to fail. This program helps us to learn more about each other and our passions. Leaders like myself also get to uncover talents we wouldn’t know of otherwise. Then there’s the added benefit of learning a little bit about fox hunting, high-protein diets and Ethiopian wedding ceremonies (just a few of the most recent topics).

We also support a company-wide book club. We choose a book and buy everyone who is interested in reading it a copy. Small groups of four-to-six people will then get together for lunch or coffee, on the house, to share their reflections with each other, and, as a group, with me. I’m not asking for book reports. I want them to think about what they learned from the books and how what they’ve learned can impact the company and their teams. Our most recent book, "The Power of Moments," has inspired us to overhaul our career pathing and onboarding programs, and accelerated investment in certain customer-facing areas.

Related Article: Digital Workplace Leadership: It Takes a Village

Building More Resilient Companies

Our culture of curiosity, enthusiasm and impact is strengthened by starting from the truth that everyone contributes to the health and strength of the organization. Thanks to my son, I now know that’s what leaders need to do: They need to foster and encourage the growth of every employee, because that’s how you build a more resilient company.