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Surprising Lessons In Life and Leadership From Today’s Top Executives

Life Lessons & Leadership
Written by Grovo

At Grovo, we’re always looking for new insights on how today’s top performers learn. And while we believe online training is one of the best ways to develop your professional skills, we recognize that oftentimes life itself is the best teacher.

We recently interviewed a handful of successful business leaders to discover what life lessons influenced their leadership techniques.

Our interviewees graciously shared inspiring anecdotes about leadership breakthroughs they’ve had off the clock that substantially impacted the way they operate on the job. Their stories and insights struck a chord with us, and we’re sure they’ll resonate with you too.

Building trust & relationships through skydiving

Maia Josebachvili is the VP of Strategy & People at Greenhouse, where she’s part of the executive team that’s led the company through 8x growth in just two years.

JDrabent_Prowly“I was an avid skydiver for many years. I did about 750 jumps during my early 20s. The whole experience shaped much of who I am, but in particular, it really informed my management philosophy and my approach to relationships. When you’re skydiving with other people, you have to default to trust. Your life is dependent on your fellow teammates, and you have a responsibility to take care of them as well. If something goes wrong mid-jump, you want to know that they’ll do everything they can to help you. And it goes both ways. No matter who I was jumping with, I had their back. I always did  gear checks on people before they jumped, and when I jumped with those less experienced than me, I made a point to answer any and all of their questions to ensure they felt comfortable with the dive.”

 The stakes are (luckily) lower with management, but I still find that the same 3 basic principles apply:

  1. I trust my team wholeheartedly. Everything is built on trust, and I default to trust. 
  2. I have my team’s back. It’s important they know that they can always count on me to help. 
  3. We’re a team, and teams have fun together.


Balancing family duties with CEO responsibilities

Joanna Drabent, CEO and Co-founder of Prowly, a SaaS company that provides public relations and content marketing services, on how motherhood taught her the seriousness of time management: JDrabent_Prowly

In March this year I gave birth to my son, and it had a crucial impact on how I manage my time and tasks today. Before that I could sacrifice most of my time for Prowly. Now I have a lot of new duties, but days didn’t get any longer. That obviously made me develop my time management skills, but it also helped me value each minute I have and make the most of it.

 “I remember that before my son was born, I overlooked every single aspect of our work. Not because I had to – I just needed to make sure personally it was all safe and sound, whether it was a new feature, client demo or a Facebook post. It doesn’t work this way anymore – I love to be up-to-date, but there are areas and tasks that are beyond my responsibilities, be it our content marketing strategy or new press releases. I have a wonderful team which I can trust. I can be sure they know what to do, which gives me more time and space to manage my own work better.”


Translating parental instincts into leadership skills

Jason Lauritsen, the Director of Client Success at Quantum Workplace, an employee feedback software company, disclosed how becoming a parent made him a much better manager:

matthew bellows yesware“The experience of parenting reminded me of our most basic and important human needs. The needs we have as children to be loved, validated, heard, nurtured, and encouraged don’t leave us as we get older. These same needs are what we long for in a healthy relationship with our work. So, as a leader, I recognized that if I can stay tuned into these needs and positively contribute to these feelings for my team, they will feel better about work. And, as a result, they will do better work. This is really what we are talking about when we talk about employee engagement.


Zen and the art of management

Matthew Bellows, CEO and Founder of Yesware, an email tracking platform, enlightened us with his story of improving his leadership technique through meditation:

matthew bellows yesware“I spent a year in a meditation center in the mountains of Colorado. I worked in the kitchen and practiced sitting meditation from 2 to 14 hours a day.”

“Meditation made it easier to see things from other people’s points of view. The world became more flexible and explicit extrinsic goals mattered a little less. All these developments have helped me become a better manager.”


On the surprising success that failure can bring

Sean Kelly, CEO & Co-Founder of SnackNation shares his story on failing when least expected and how taking things a little less seriously can lead to positive outcomes:

sean kelly snacknation

“One of the most powerful leadership lessons I ever learned came from a bitter disappointment in a national snowboarding competition.
“In my late teens, I was serious about competitive snowboarding. I spent an entire year training for the halfpipe event at this particular national competition. Finally, I found myself staring down at the rock hard, icy blue walls of the halfpipe.
This was it. It was time for me to take my run. But it wasn’t the run I expected.
“I fell before I even hit the first wall of the halfpipe, slipping out on my back edge and sliding 10 yards down the icy base on my back. That had never happened to me before, not even in practice. Not even as a kid learning halfpipe for the first time. Yet here I was, during the the last and biggest competition of the year – the competition I spent my entire year just trying to qualify for – and I make a catastrophic, almost unthinkable error.
“It was one of the more painful moments and ego hits of my life. I thought my year, my season, had just blown up in front of me. My embarrassment was excruciating.
“I had qualified for another competition, called “slopestyle,” the next day, but it wasn’t my best discipline, and I didn’t expect to make the podium.
“But as it happened, I took third place and won the bronze medal that day. My failure the day before allowed me to take myself less seriously, become more creative, and just have fun. I think the judges saw this. Perhaps more accurately, the judges saw what I felt, and rewarded me for it.
“The lesson? Fail to live.
“I believe that failure is a part of life, so the best strategy is to make peace with it and make the best of it when it occurs. Failure has a way of making us feel alive and connecting us with our true selves. This is a lesson that I’ve carried with me throughout my leadership career.”


Leadership lessons from a World War II veteran

Michael Candullo, COO and Founder of Path Interactive, a NYC search marketing agency, briefed us with his encouraging managerial strategy:
“My father was a Marine who served in WWII. He always taught me to identify and know your possible outcomes. He would plan for the worse and work toward the best.”

A good plan takes flight.

A good plan takes flight.

“This has served me well in that it helps me manage my teams toward possible outcomes and puts all considerations on the table as we are working toward an end goal. This process allows my teams to stay ahead of our client’s needs and goals.”

A tough conversation that taught volumes

Brent Summers, the Director of Marketing Content at Segment, a customer data hub, shared the story of a day that changed his life:

matthew bellows yesware“Shortly after my 18th birthday, I was diagnosed with Hodgkin’s Lymphoma. Seventeen years later, I can still remember the way my doctor delivered terrible news to me. He was compassionate and kind, but more importantly, he made me feel like I would be successful in battling an insidious disease.”

“He called me personally to schedule an appointment so he could tell me the results of a battery of tests. In the exam room, he was direct, “You’ve got cancer.” [pause for dramatic effect.] “This is obviously a serious diagnosis, but it is definitely not a death sentence.” He answered my questions and went on to explain the proposed course of treatment, including the side effects. He told me I had an 85% chance of survival and connected me with a support group.”

“I learned a lot from Dr. Francesco that day about how to handle tough conversations: State the purpose of the meeting, describe the situation and the consequences, actively listen to the person’s response, discuss a solution, agree on a plan and follow up, and state your support.”

“When someone is underperforming, I need to hold them accountable while also motivating them to do better. As a manager, it’s my responsibility to support my team and make them feel empowered to do better.”


Stay tuned. More to come.

As these stories illustrate, some of the most valuable leadership and management lessons can be learned in the course of everyday life. We’ll continue adding new quotes and stories from some of today’s most successful leaders in the coming weeks and months.