Keeping it Personal, at scale: 4 Learnings

Like many of you, I’ve always liked to lead “in-person”, frankly I thought it was nearly a requirement of great leadership and nothing has been more important to me than meeting with our FlyMates (employees) who work around the world at Flywire. I often say that to go global with your business you actually have to go there physically, that a leader should be the first person to "jump out of the airplane", the one that should be leading others into battle from the front, etc.

Our last two years have included hyper-growth and transition to a public company via an IPO (#FlyPO)...so how I connect with our 750+ FlyMates was going to evolve, even if COVID-19 didn’t force changes to it. Travel restrictions & lockdowns aside, it was getting much harder for me to personally meet every new FlyMate, and check in with the hundreds of amazing people that have been here for years. My leadership style also had to adjust to leading a public company in a post-COVID world, forcing me to reprioritize my commitments and get creative with travel & team engagement.?

While I can no longer swoop into every Slack channel and ask 20 questions on a project or initiative (and frankly, I’m not sure FlyMates would want me to!), I do make the time to spend time with FlyMates, outside of traditional work time, to personally recognize accomplishments, to call or message them when they are dealing with tragedy. Yes, I also still review / sign every offer letter & I Slack every new FlyMate a quick note to welcome them. I do these things because I believe the connection people have with their team matters & empathy is the cornerstone of great leadership.

Right now, it seems like empathy is having a moment - and for good reason.? Some 76% of individuals with highly empathetic senior leaders report often or always being engaged at work, according to recent research from the global non-profit Catalyst - and 61% of these employees report always or often being innovative at work.??

How can leaders infuse empathy into a workplace that is rapidly changing & one that is remote or hybrid? Here are four things that have helped us at Flywire.?

1. Trust teams to make their own decisions on where they work best

In empathetic cultures, colleagues respect that things are fluid and trust peoples’ ability to adjust as needed. At Flywire, we have offices all over the world, so FlyMates were accustomed to virtual work and we never viewed in-office work as a prerequisite to success. So when many companies started forcing their employees back to the office, we took a strong stance against that, because we’ve proven that empowering our FlyMates to make their own decisions on where they work creates a more engaged, fulfilled workplace. And by setting the tone from the beginning that all ways of working are accepted, teams that are a blend of all those options can quickly adapt and work without friction. These days, we keep our offices open when local rules allow for those who crave in-person collaboration. We also regularly invest in corporate retreats - what we call FlyLodges -where they can spend time together in unique locations working and socializing. So far, FlyMates have enjoyed the FlyLodge experience in the USA, Israel, China, Romania, and Spain with more to come in the future!????

2. Everyone EXPECTS you to talk, so look for opportunities to simply listen

Globally, Gallup reports that only 20% of employees are engaged at work. Companies with engaged employees have lower turnover, as high as 43%. ?There is one person hired every 15 seconds now on LinkedIn , so companies need to act fast to combat the changes around recruitment & retention.?

Taking the time to listen can be a powerful driver for employee engagement. One of the stats I like the most in our “Best Places to Work” designation is that 96% of FlyMates say management is approachable and easy to talk with. I think a major reason for this is that our executive leadership team at Flywire thinks about organizational hierachy in reverse, where senior leaders are at the bottom of the pyramid & they work for their teams (which are at the top). This respect for the contributions of every employee is why transparency is such a big thing at Flywire, and why people actually believe they can ask us anything. During COVID, we accelerated the frequency of our All Company meetings, and always include a live Q&A and strived to questions in an honest and authentic way - even when we didn’t have all the answers (which was often!). Executives will also regularly host drop-in “office hours” so they can answer questions in a more private setting. Small changes like this can make a big difference & they will lead to many great this...

3. Give people a voice & allow them to take action

People in leadership positions should not be the only ones practicing empathy. In fact, employees are acutely aware of when companies do it for PR and can easily identify when leaders are not always practicing it authenticly. In a survey from EY , 42% of employees say that their company does not follow through when it makes promises.?

To prevent falling into that trap, companies need to let their employees know they have a voice and can be change agents - because they will accomplish amazing & impactful things. Our employee-led resource groups have doubled down on providing resources for our global FlyMates throughout the pandemic, like the mental health training and allyship training run by one committee, FlyMates First. And our employee-led Charitable Foundation has provided numerous academic scholarships to students all over the world struggling in the pandemic.?We also decided to give every FlyMate 2 "FlyBetter Days" that are paid PTO (above their generous annual PTO amount) to contribute to their community, to volunteer & help a cause they feel passionately about.

4. Encourage & support the pursuit of fulfillment (for yourself & team)

We have let go of the fantasy that people can "balance" personal & professional lives. These days, they are inextricably linked - and that is OK with me. Our FlyMates may be caring for an aging parent or an ill spouse/partner. I often see children in the background on Zoom calls, even during Executive Staff meetings. I recently went to one of my son’s playoff soccer games during a post-earnings follow-up call, and ensured all parties were aware of my decision. The true goal is to pursue fulfillment & as leaders we have a duty to foster that within our organizations, not forcing people to make impossible choices between their work & personal lives.

I posed some simple questions to our FlyMates on our internal blog at the end of 2021 – what do you want to accomplish this year at Flywire & what do you want to accomplish this year in your personal life? By asking these questions, and highlighting the importance of BOTH personal & work lives we recognize both are crucial to the Fulfillment Journey.

When people feel that they can truly be themselves, they can start to be completely honest about what they really want to accomplish in their personal and professional lives. For leaders, using empathy to unlock that potential is key to thriving as a company...especially during uncertain times!

~ M.