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Scott Case: In 2021, remote work is still the norm for many. Here’s how to keep employees engaged

The return from holiday break offers a chance to assess and improve your remote team’s performance — even if you've already been working at home for months.

Scott Case. (Courtesy photo)
This is a guest post by Scott Case, CEO and cofounder of Upside Business Travel and founding CTO of It appears here as part of a partnership with DC Startup Week 2020.
Employees are the lifeblood of a business.

When our employees are passionate about their work and feel connected to our company’s mission, they are engaged and good things will happen. In fact, organizations with highly engaged employees are significantly more profitable and productive, according to Gallup.

Keeping employees engaged requires a commitment from all leaders within the organization — especially now, with more Americans working from home than ever before. It’s critical for leaders to invest time and resources in your team to ensure they operate at peak performance.

But where do we begin in this new year, when so much looks like the uncertainty of the old one and when some companies are implementing work-from-home-forever policies? This return from holiday break offers a chance to assess and improve your remote team’s performance — even if you’ve already been working from home for months.

[Editor’s note: Read Case’s thoughts on how leaders can better communicate remotely and the importance of mental health when professionals are feeling stuck.] 

To say COVID-19 has disrupted business norms is a dramatic understatement. Remote work environments are now more prevalent across a wide range of industries. For many people, commutes no longer require trains, planes and automobiles … or hours slogging through traffic. Commuting has become 10 short steps from the bedroom to the kitchen or home office.

The result for some is a sadistic, M.C. Escher sketch that mashes-up work-life and home-life — it’s impossible for employees to mentally separate the two. This causes stress and anxiety, which leads to dissatisfaction and decreased productivity. That’s not good for our team or our business.

Of course, we could look at this new normal as a problem or as an opportunity. I choose the latter. So does my friend and colleague Joe Mechlinski, a New York Times best-selling author and the founder and CEO of Baltimore-based business consultancy SHIFT.

SHIFT’s Joe Mechlinski. (Photo via LinkedIn)

Here’s how Joe described the current situation in a discussion we had during DC Startup Week 2020:

“I think COVID is giving us a chance to reassess our values and the things that we care about. I don’t think being an entrepreneur is an excuse not to take care of yourself, not to take care of your employees, not to take care of your community. I think we’ve all pretty much gotten that software update. This is an amazing opportunity to live a better life.”

Like Joe, I believe we’ve got an incredible opportunity sitting in front of us to start fresh in how we engage our teams. We also have the obligation to do things differently if we want to succeed.

Here are some practical ways to tackle the new reality:

Meet frequently, but not constantly

Nobody knows the next time we’ll be able to have a meeting with our entire team in the same room. For now, video conference calls are an easy and effective solution for face-to-face interactions.

The only downside is that they are so easy to set up that many people find themselves on video calls all day long. Which is exhausting and a major threat to productivity.

As leaders, we set the expectations. We set the pace for how often our teams meet. And set boundaries for when they shouldn’t.

  • Identify days and times for mandatory meetings. Make sure these time blocks are consistent and that you stick to them. The consistency will become an anchor point for your team, which will help them be more productive.
  • Teams of eight to 10 are probably working together all day long already — they may not need more structure.
  • When it comes to “all-staff” meetings, it depends on the size of the organization. Smaller companies (up to 50 people) may want to huddle weekly. Larger organizations might be more comfortable meeting every six to eight weeks as a full unit.
  • Additionally, consider blocking a period of time each week where meetings are “illegal.” Demand that your team respects those heads-down hours, and you’ll start to see an increase in engagement. We’re running an experiment for no video meetings after 2 p.m. on Wednesdays.

More than ever, personal is business

Pre-pandemic, dogs, cats, toddlers, and teenagers interrupting work were there but separated by space and time for most of our colleagues.

Now, we are literally in colleagues’ homes — their kitchens, bedrooms and living rooms — and those interruptions are common. The trick is to embrace them or simply let them go.

Our job as leaders is to be compassionate:

  • Express that we understand the incredible pressure they are under, many of whom are juggling child care or additional family responsibilities during this pandemic.
  • Encourage people to stop apologizing for home-life interference. Dogs, cats, kids — they will all Zoom-bomb your employees at some point.
  • By supporting the team unconditionally, they will feel empowered and focused on doing great work, even if things on the home front are a little crazy from time to time.

Make space for fun

Our teams used to grab lunch together. Or drinks after work. They played on a company kickball team and had 1:1 professional relationships that left them feeling inspired and energized. Now, it’s all a distant memory for some and never existed for people who joined the team during the pandemic.

Remote workers don’t have the same opportunities for serendipitous moments. Virtual communication is much more intentional. We get on a video call to solve a problem or discuss an opportunity. We don’t often just hang out like you would in an office environment.

But those relationships and subtle in-between-work moments are critical to maintaining our culture. Creating space for extracurricular connections between employees, ideally centered around common interests:

  • See who’s a movie buff and encourage monthly movie nights voting on favorites or themes.
  • Hire a local musician to perform a virtual mini-concert. It won’t break the bank and it would be a fun experience to enjoy as a group.
  • Play virtual games. There are so many games that can be played on a video call. Check out this resource for ideas. Teams bond when they achieve things together, so encourage it to happen.
  • Set up 1:1 virtual coffee catch-ups between teammates. Randomly pair people each week and book their calendars for 30 minutes. They’ll be amazed how rewarding those conversations will be. If you have Slack, check out Donut. [Editor’s note: Slack prompts are fun, too.]
  • We invite our team to host regular “lunch and learns” on topics they are excited about. The presenter gets to share and the audience self selects the topics they are interested in.

Motivating teams to achieve great things is the number one job as a leader. It’s also one of the most challenging aspects of the job and the current environment is a next-level challenge for us.

For more ideas to help you grow and scale your business, and to listen to the full interview between Joe and Scott, check out the “Staying Connected while Working Remotely” episode of the Founders Focus podcast.

Series: How to Work Remotely
People: Scott Case
Projects: DC Startup Week

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