We are not the people we were a couple of years ago. And it's even more evident that we are not working as we did. The collective experience we've all had has made a lasting imprint that is evolving the way we work.

According to Ladders, 25% of all professional jobs in North America will be remote by the end of 2022. And remote opportunities will continue to increase through 2023.

We brought three CEOs together from Scoop, Bucketlist Rewards, and Welcome to learn how they're leading their distributed teams and what they're seeing and predicting for the next 12 to 24 months.

Missed this session? Read the summary below or access the recording here.

Featured panelists:

Roberto Ortiz, CEO & CoFounder of Welcome

Rob Sadow, CEO & CoFounder of Scoop Technologies

Jason Lindstrom, CEO of Bucketlist Rewards

Q: We're seeing that a lot of knowledge workers want flexibility. What are you seeing as the pros and cons of flexible work?

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Roberto Ortiz started the session by discussing the pros of a more flexible way of work, beginning with the benefits. "Flexibility benefits the employee when they have choices where to live, but it also benefits the employer to be flexible to employ people from around the world."

"Being more flexible has forced us to restructure how we meet and is causing us to rethink how we operate from the ground up. The cons are the level of intention it takes to run a successful organization today versus two years ago. To some, it can look like a con because it looks like more work. But this is the fast-track way to becoming a more future-oriented workforce. Companies must do the work to figure out how to drive a more equitable experience for distributed teams and ensure they have the right technology in place."

Rob Sadow spoke about the impact flexible workplaces have on the local economies. "One of the huge benefits I see is the ability to enable talent in local markets to have access to more jobs and, as a result, build local economies. Certain metros or cities hogged up talent in tech, so the idea that people can be more distributed now and work in different locations is extremely powerful."

Q: How are you managing flexibility for your company, balancing productivity and wellness so employees don't experience burnout?

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Rob shared that Scoop has started offering company-wide time off. "We took off the whole week of July 4th and the week between Christmas and New Year's. We found that when everybody's work stops, the likelihood of you getting pinged with something else while you're out of the office goes down. People still take their PTO, but having those moments of pause on the calendar has been a good refresher for folks trying to find some balance."

At Bucketlist, Jason Lindstrom said they started struggling with work/life balance when they became a distributed company with employees worldwide and trying to manage multiple time zones. "We built a playbook policy on distributed work. One of the best takeaways is that we have a four-hour overlap where we expect everybody to be available on Slack, email, etc. Outside those hours, people can set their own boundaries regarding family time or health and wellness."

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Q: Managing distributed teams is evolving the way we communicate and lead. What are the challenges you're currently encountering with that? How do you see this will evolve in the future?

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Roberto believes we're just scratching the surface regarding the tools and technology required for remote workforces. "There's a ton of new technology that has to be built as we're experiencing new challenges. As technologists, we must figure out how to improve those problems. For example, hosting an all-hands meeting on Zoom and recognizing it doesn't feel engaging. I don't feel the music, I don't feel the presence, I don't feel the energy that I want to feel that requires a new way of thinking to better engage your employees. What is the current status quo, and is the status quo good enough? I think we're never satisfied with the status quo; there's always a better way of doing it. When you look into employee communication and management, one side of it is technology based, but a lot of it is around policy and intentionality around investing in middle managers. Before Covid, there was a different manager that never managed a distributed team before. They relied on seeing their team in the office, walking in the door at 8am and out at 5pm. And that's how they measured success. Those managers will have a hard time if they don't change how they work, so I think equipping middle managers is essential."

Rob commented that companies tend to spend a lot of time worrying about the hardware and the tooling needed, but half of what is required are soft skills. "If I had to guess before the pandemic, 1 to every thousand or ten thousand managers had previously managed a remote or hybrid team. The collective knowledge and best practices of managing a remote workforce are relatively minimal. Managers have to get better in this world. This means you have to be more thoughtful on what the output is you're trying to drive, how folks on the team contribute to that output, and how you find the right balance around checking in personally, professionally, and supporting them."

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Q: From a tactical perspective, what signals do you look for in your remote teams? We often see someone in a virtual box; how are you picking up on their cues? 

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Jason shared some experiences Bucketlist uses to unearth emotional cues. "We've created ten questions team leads will ask employees during their weekly 1:1 meetings. One question they ask is, what is the best thing to happen to you this week, whether in or outside of work? We want to make it feel safe for people to talk about what's happening in their lives. Another subtle question is asking, on a scale from 1 to 10, how happy are you and why. Often we walk around in life and ask others how are you doing, and they say fine. But in reality, maybe they are struggling with rent, or sadly their dad just died. But fine is the same answer across the board. When you ask a number out of ten, people will give you a more realistic response, and then you can dig deeper if they want to share more. I've also found people have different baselines. Some people are naturally a 7 out of 10 week over week, others a 9. Then you can watch the trend line. If someone is usually a 9, but lately they've been a 4, something is going on that you may want to learn more about."

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Q: What is the one top prediction you're excited about and prioritizing for your organization?

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Rob believes that most of the world that can operate remotely will do so in a hybrid environment, not just next year but into the future. "The biggest barrier around hybrid is the ability for people to work at the right place and at the right time. This means you're home on the right days and in the office on the right days, and you can get the right people together. We spend all of our energy from a product perspective trying to make that as easy as possible. Hybrid is the future for most people, and intentionality around that is extremely important. 

Roberto thinks about the short and long term and the in-between. "There will be many more digital nomads, and more people owning their careers and prioritizing life first, then work. I think that's the significant shift that will happen. The belief is that I want to live this certain life; therefore, I work this way. There's a journey in equipping people to think like that, not just for employees but employers. Make sure people know the expectations as an employee, and make certain the expectations are outcome driven. As a leader, saying this is what excellence looks like at the job, now go be excellent and live an excellent life on your terms. I think the foundation is trust, and that's the big shift that will need to happen in employment. 

Missed the session? Watch the entire event here for top trends and predictions for leading distributed teams in 2023.

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