Managing Remote Workers Through Chaotic Times

Managing Remote Workers Through Chaotic Times

By Robin Caputo, Chief Marketing Officer, Datavail

It is incredible to think about how much things have changed in just three years. In 2019, I managed a team that worked a hybrid schedule — three days in the office and two from home. Now, my entire team, including me, works entirely remotely. In addition, many people have changed jobs, careers, and even locations. I ended 2019 in the suburbs of Colorado and now live on a 60-acre farm in Virginia.

Did I ever imagine this for myself? Did anyone imagine the life they have now? I don’t think anyone did.

The Pandemic Was Just the Beginning

Unfortunately, the waves of change aren’t slowing down. The pandemic was the first hard hit we took, immediately followed by a sudden shift to remote work. Leadership teams across industries had to enact rapid digital transformation to ensure their employees had the technology and security resources needed to continue doing their jobs. This increased demand for IT professionals and created an even larger talent resourcing issue in an already-undersized workforce.

In addition, these employees took on far more responsibility than usual. I had two single fathers on my team working from home, and their kids were also schooling from home. I had to be extremely flexible during this chaos to ensure I didn’t lose sight of each team member's personal and professional challenges.

The Great Resignation

Of course, shortly thereafter, we experienced the Great Resignation, a situation that probably shouldn’t have been as shocking to us as it was. Employees were stressed. Many didn’t have resources like childcare and didn’t receive the flexibility they needed from their companies. So they left for higher salaries and greater autonomy.

Datavail conducted a study last year to better understand what organizations were experiencing during the Great Resignation. Here are some eye-opening insights we uncovered about why these companies were losing tech talent.

  • 67% of tech workers left to pursue other opportunities
  • 40% were burned out from working long hours
  • 30% left because their teams were understaffed

In addition, 63% of the organizations we surveyed stated that finding qualified tech talent was their number one challenge.

Four Dramatic Shifts in Two Years

We talk like the Great Resignation is a problem of the past, but it is still ongoing. And if that wasn’t enough to put us all on edge, we’re now facing a recession.

If we look at these four major shifts — the pandemic, the shift to remote work, the Great Resignation, and the recession — they each occurred in rapid succession across just a couple of years. That is no small chain of events.

And companies are struggling. Supply chain issues are still challenging, affecting revenue, profitability, customer satisfaction, and employee effectiveness (how can we forget the ongoing computer chip shortage)? The labor shortage means companies are scraping budgets for higher salaries to improve retention and attempt to address the higher cost of living. Inflation continues to be a growing concern that is increasing the cost of doing business.

The result? Budgets are tighter than ever. Organizations must do more with less but still provide a work environment where employees feel secure and supported. Leadership teams must figure out the algorithm for effectively managing remote employees.

These are challenging objectives to address amid economic and social chaos, but they aren’t impossible. According to Gartner, the three major drivers that IT employees value when either seeking new opportunities or evaluating their current position are:

  • Compensation
  • Work-life Balance
  • Respect

While this might not seem like new information, the methods companies should use to provide these benefits are entirely different in a world of remote work than they were before. The more organizations can creatively and insightfully hone their employee offerings and improve their work environment, the greater their chance of keeping and attracting IT talent.

Let’s look at each of these and discuss how today’s leaders can provide them in a budget-conscious remote work environment.


Compensation is one of the toughest things to manage, especially when budgets aren’t very flexible. But with the costs of attrition often outweighing those of training and developing new employees, employers must consider making space for higher wages.

Now, this doesn’t necessarily mean that you must increase salaries across the board. Identify the areas where your most niche technology skills are required and adjust the salaries you’re offering to meet or exceed your competitors. Then, if the budget allows, move to broader skill sets and see where you can be competitive there.

If salary increases are simply not possible, enhancing other aspects of the employee experience can help, such as more paid time off, flexible schedules, training and development opportunities, etc. Another approach is to upskill existing employees or invest in citizen roles. You may have employees right under your nose who are interested in filling these difficult positions; make full use of the people you have. It will not only help you fill a personnel gap; it will also help your employees learn and grow, increasing retention.

Outside of yearly compensation, you can also find ways to reward your employees both vocally and monetarily. While a Starbucks gift card may not be a huge budgetary game-changer for them, it represents recognition of their achievements and appreciation for their role on the team, especially when presented publicly.

Work-life Balance

We all thought we knew what work-life balance meant before the pandemic. With remote work, the entire concept is being redefined by individuals, companies, and entire industries. So how do we provide work-life balance when its definition is so nebulous?

Recognize the Work-life Clash

Even if our work responsibilities haven’t changed in the last two years, we are all undoubtedly busier than ever. Some of us work one room away from our kids, pets, and maybe even spouses. This means more family time and bonding with those we love but includes more interruptions and distractions. Acknowledge these challenges by being patient when these clashes are apparent. Check your employee’s calendars before sending a message, and give them space to respond when they have time.

Most importantly, stand by your people. Please give them the flexibility to manage their work-life balance challenges based on their individual circumstances. That way, when another job offer comes around, they are more likely to remember how your organization had their back during tough times.

Keep Work Personal

Acknowledge the personal aspect of people’s lives. In a remote environment, it is so much easier to skip past the pleasantries and get straight to work. Instead, ask your team how they’re doing. Ask them what they did over the weekend. Encourage them to schedule virtual “coffee chats” with each other to catch up and discuss common interests.

At Datavail, we begin formal meetings with what we call a segue: Each person shares one professional and one personal highlight from their week. Doing this creates respect for each other and recognizes that everyone has other things going on outside work.

Flexibility for Availability

The big trade-off for us with remote work is flexibility for availability. Our teams work flexible schedules and are granted the trust that they can manage their work schedule. We don’t require them to send out a message every time they go to a doctor’s appointment; they only need to put it on their calendar so we can see when we will be able to reach them. In exchange, we ask that they be available when unexpected priorities or deliverables arise.

Gartner recommends including flexibility about when, where, and how much an IT employee works in your employee value proposition (EVP). “Radical flexibility,” as they call it, is essential to attracting and retaining talent, especially if raising compensation isn’t possible. Evangelize this information internally and externally in job postings and interviews to show you’re going to support the complex lives of today’s knowledge workers.

Technology and Tools

Remote work isn’t doable without the support of technology. In addition to the technology they use to build, develop, and manage your organization’s systems and applications, IT teams need to be able to communicate, collaborate, track projects, and manage their tasks. With so many moving pieces, tools that smooth and speed processes will be particularly valuable to your team. The more they have to wrestle with outdated systems and processes, the more likely they’ll jump ship for a company using cutting-edge tech to make their life easier.

Don’t forget the human side of things

When everyone was working in-office, we often stopped by their desk to chat, grab a snack in the break room, or head out for a drink after work. These may seem like small things, but the pandemic has shown us that these are valuable bonding experiences that help us connect as humans. Don’t lose those experiences with remote work — it can lead to feelings of isolation.

Our team has regular virtual cocktail hours, and we set up what we call “scheduled spontaneity.” We play online games, or pop in our headphones and go for a walk together. If setting up fun experiences like this isn’t your skillset, find someone on your team who enjoys doing these things and give them resources to plan them.


Gartner discusses the importance of showing respect by approaching conversations respectfully (regardless of how much you agree or disagree with someone), defining ground rules for interpersonal disagreements, and communicating openly. In my experience, all three of these are integral to showing respect and earning your team's respect.

Here are some additional suggestions that will help you accomplish this:

  • Praise in public but criticize in private. This helps your team members maintain positive relationships with each other while also offering opportunities for individual improvement.
  • Address conflict head-on. Especially in remote environments, it’s so easy to avoid conflict altogether. Discuss issues openly and honestly and try not to get defensive. Teach your team members to build this skill.
  • Get an understanding of team dynamics and styles of working. Frameworks like Myers-Briggs and KOLBE can help you and your team better understand each other’s strengths and weaknesses, leading to greater respect.
  • Be very clear and detailed when setting goals and objectives. Regularly review your team’s progress against them so they know where and when to adjust.
  • Don’t schedule meetings needlessly. Ensure every meeting has an objective, KPI, and agenda so your team knows they aren’t wasting their time.
  • Encourage your team to schedule focus time — a time when they can turn off their notifications and make progress on a specific project. Respect that time by holding your questions until they are available again.

The Path Forward

If the past few years have proven anything, it’s that the future is unknown. We hope the recession is the final stage of this seemingly unending string of bad luck, but who knows? Maybe someone will decide to fry up a capybara, and this whole cycle will start again.

In the meantime, these times of chaos have shown us a few cracks in our foundational understanding of humans and work. We now know that people are much better than we expected at managing their schedules and workloads without consistent oversight. We now know that caring for our tech workers requires much more than providing a salary and benefits. We now know that as much distance as we’ve had from people, we need human connection both inside and outside work.

Most importantly, we now know that whether our evening view is filled with stars or high-rise buildings, our world will continue to rely heavily on technology. The line between life and career is thinner than ever. Finding people with the skills to manage and build new technology is key to navigating this new existence as organizations and individuals.

So start the process of evaluating your compensation's competitiveness, enhancing your employees' work-life balance, and making the expression of respect consistent and habitual across your organization. This will put you in an excellent position to guide your company and employees through the recession and beyond.

Robin Caputo

Robin Caputo

Robin Caputo is the Chief Marketing Officer for Datavail, an IT services provider that has been listed on the Inc. 5000 list of “Fastest Growing Private Companies” for more than a decade. Robin has 30 years of marketing experience in technology and telecommunications. The Datavail team is an avid supporter of OATUG, sponsoring and speaking at online and in-person events.

At Datavail, Robin manages a remote team of 15…and at her own remote location, add to that a flock of 50 sheep, two Great Pyrenees and one Black Angus calf. She and her husband emerged from the Pandemic relocating from suburban Denver to the village of Cartersville, Virginia on a 60-acre farm. She, however, had absolutely no prior experience managing sheep, so it was all O-J-T over the past year.

Follow Robin Caputo on Linkedin and Medium.

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