|11 Minutes

4 Tips for IT to Conquer their Big, Ugly, Remote Experience Challenges

4 Tips for IT to Conquer their Big, Ugly, Remote Experience Challenges

“The best laid plans of mice and men, go oft awry, and leave us nothing but grief and pain”

It may sound cliché but think back on the 2020 you had laid out and the 2020 you experienced and you’ll know it’s true. No matter what company you work for or what your job description entails, I’m willing to bet you had to throw a lot of good plans out the window when the pandemic hit. And if you didn’t, call me, I’d like your advice on some lottery numbers.

As the Director of Client Services at Pegasystems, I know my team and I went through a steep learning curve in those initial weeks. We went from building meticulous adoptions plans—which typically took 3 months to set in motion—to building out those same plans in just a few days. Like many in IT, the first challenge we tackled was how on earth we were going to overhaul our entire onboarding experience for new hires so they could integrate as quickly as possible into our technology setup—a task that seemed infinitely more challenging without in-person coaching.

And then there’s the dreaded M word – meetings! How could we harness the power of digital face-to-face time to provide meaningful connections for our employees and ensure that our culture survived without dreaded #zoomgloom? What’s the right combination of technology capabilities and meeting rituals to strike a healthy balance? I think we’ve all spent much of the past 11 months trying to fine tune this.

You may not know the next line to that poem is “For promised joy!” Many of these challenges were became blessings in disguise. Ok, not the #zoomoverload…although the Lawyer Cat has certainly been a welcome distraction. As ridiculous as it may sound, our biggest problems this past year have morphed into becoming our most promising opportunities.

Below, I highlight some of the problems my team and I faced during this uncertain time—problems that I am certain many of you in similar roles are still struggling to manage. But fear not, in reality these are Big, Ugly Beautiful, Remote Experience Challenges Opportunities you can use to spur growth and innovation for your business (even amidst pandemic fatigue and uncertainty).


IT innovation is complex and challenging – but it can be done in record time with the right approach.

There’s long been a stigma about knowledge workers that they can’t adapt quickly. The Nexthink Pulse Report revealed that many IT executives lack confidence in their companies’ ability to innovate and manage digital transformation and application deployment projects.

The pandemic left us with no other choice but to adapt quickly. And at Pegasystems—and I’m sure in many other companies around the world—the belief that employees are not resilient to change was proven false.

IT teams can indeed implement major changes over the course of days rather than months. They can deploy new technologies in record time. Rapid innovation isn’t impossible; it just requires the proper guidance and an agile mindset from IT support.

In fact, I experience this necessary mindset change first hand. I’m used to creating these thorough and thoughtful adoption plans with use cases to nurture the change curve and adoption, and evangelizing and rewards for Early Adopters, operational support excellence for the Critical Mass, and fashioning methods to convince technology-resistors, but then all of a sudden the pandemic came out of nowhere and disrupted my process.

What I discovered is that the modern role of IT Support is as a wayseer and enabler for just-in-time employee learning. And, in fact, the resistors are the ones most in need of new ways of working in the post-pandemic world.


Remote onboarding is really hard – but it doesn’t have to be.

Let’s face it: there’s not a company on the planet with a perfect track record when it comes to onboarding. But, you never get a second chance to make a first impression, especially as an IT support team. Anyone who has started a new job has gone through moments of feeling a little awkward, a little lost, a little confused. But when you take the inherently difficult process of onboarding and put it in a fully remote setting, those challenges become even more pressing.

At Pegasystems, our new employee onboarding is a rich cultural affair, one which I had the benefit of experiencing in-person because I joined Pega one month before the pandemic hit. But, it’s perhaps ironic, the first thing I set as a goal in my role Directing IT Client Support was to update our IT onboarding to be more personal. Picture this, the IT onboarding was a 30 minute session at the end of a long day, with an IT technician trying to get 40 people to follow steps to reset their password, set up MFA, test VPN, and get email on their phones, all at the same time. And if you are shuddering to think of it, good, it was that awkward.

The day I left the office to work remotely I was faced with a new class of employees onboarding in just 4 days – 100% virtually. Of course, we sent the employee’s IT equipment ahead, but we constructed a day-1 experience that starts with a 1-1 meeting between IT and the employee in their remote work environment.

This more personalized approach was a watershed moment for me and my team in several different ways. For one, it helped to establish bonds with new users. No employee wants to feel like they’re left alone on an island when they start a new job, and that’s an even bigger issue when each new hire is literally isolated from their new colleagues. Plus, this approach quickly established my team (IT workers) more as consultants who were there to help, rather than distant technology instructors who were there only to dictate the rules.

I’m happy to say that our new and improved onboarding strategy has been a success. Since the pandemic started, we’ve successfully onboarded over 1,200 new employees!


The balance between self-healing and IT intervention became even more delicate.

IT has always had to strike a balance in how they engage with users. Intervene too often, and employees start to regard tech support as the nagging parent, always dropping in to tell them what they’re doing wrong. Intervene rarely, and end users feel like they have no support at all.

The pandemic has made this push-and-pull between IT and employees even trickier. But it’s also forced IT to take a closer look at how they offer support—which has led to new breakthroughs in IT-user relationships. Our goal is to solve problems before they are reported and save our interaction for helping users to find new ways to leverage technology for business value – Consultants > Technicians.

We’ve learned new ways to support remote workers, without employees feeling like IT is (virtually) breathing down their necks. Automation has enabled us to solve problems rapidly, before they’ve made a negative impact on employee experience. We started this year with some BHAG’s (big hairy audacious goals) to provide a self-service and self-healing approach to service because we recognize that employees have less time and more technology knowledge than ever before. And, we will meet employees on their preferred communication channel, by rolling out a contextual chatbot to help us offer a guided experience. Our hope is that our remote employees feel like IT is always there to help but never there to intrude.


We’ve had to redefine employee collaboration and rethink how we measure employee productivity.

No more long commutes. No more distracting side conversations in the kitchen. Working from home gives you so much more time to actually work, right?

I can sense the collective eyeroll.

If you thought “meeting overload” was already a problem, the pandemic took it to the next level. Cue the half-hour video calls that should’ve been an email, and the emails that should’ve been an IM. Many managers also faced the challenge of leading a remote team for the first time in their careers and needed to tackle a wide range of issues from not being able to build team comradery, to spotting the employee who needs help, and of course…the Netflix bingers.  Far too often in 2020, meetings became less about bolstering collaboration and more about filling our calendars just for the sake of doing so. It got so bad, many companies started to declare meeting free days!

But, it is important to measure employee productivity, especially among remote workers. There are a lot of factors that can drag employee productivity down: not having access to the right tools, not having connections to the right people, and of course a new season of Schitt’s Creek.

The good news is that a combination of cultural tweaks and IT interventions can turn these frowns upside down:

Analyze scheduling to avoid meeting overload. IT facility managers partnering with AV and Collaboration teams – potentially with the help of AI – can examine meeting scheduling across the organization, offering solutions to cut down on meaningless meetings, spot trends possibly for meetings that fall outside traditional work hours, and help remote employees leverage a full suite of digital collaboration tools and capabilities for more impromptu interactions.

Provide support to make meetings more engaging. It’s important for us all to consider the psychological impact of virtual meetings vs. in-office conversations. University of Michigan professor Jane Dutton’s research showed that when we have high-quality connections, we feel a positive regard for each other, we feel that someone sees the best in us and there is mutuality—an openness between people and vitality—an energy transmitted by said interactions. This is harder to achieve remotely, but not impossible to do in digital meetings. IT can help pave the way by offering guidance on backgrounds, noise reduction, camera positioning, and training on how to have just-in-time impromptu digital interactions.

Introduce new KPIs for measuring productivity. There’s a fine line between helping employees be productive and snooping on employees to make sure they’re being productive. IT can look out for both the employee’s and the company’s interests by taking a more holistic approach to measuring productivity. Monitoring app usage, device performance, task completion, and other metrics can provide a helpful overview of employee productivity. The focus should be on removing digital roadblocks for people not obsessing over number of hours logged on the computer.

Though we’ve made many improvements since the start of the pandemic, we still have much to learn.

The pandemic thrust IT to the center stage and in many organizations, IT teams were declared the MVP of 2020. Now as we enter into a post-pandemic future (fingers crossed) and the spotlight remains fixated upon us, we must deliver continuous improvement, ROI, and layer experience excellence on top of operational excellence. This is an exciting time as companies shift out of pandemic mode and are considering the future of how and where work is done. But we’re literally learning on the job, how lucky are we?!

Employee health, once considered a taboo in American offices at least, is now thankfully becoming more of a priority for companies. In terms of physical health, how can we ensure that our remote workers are getting the care they need, whether it means providing temperature checks or routine health checks? Then there’s mental health, which has become an even bigger priority since the leap to remote work. How can we assess the impact that virtual work has on employees’ mental health, productivity, and overall wellbeing? How can IT and HR work together to proliferate your organizations culture and keep employees happy and productive?

Last but not least, we’ll have to continue to think of new strategies finding the best and most diverse talent. How do we provide workspaces that employees want to visit, while supporting the sprawl of home offices that are here to stay? What technologies do we provide to new hires, and how do we improve IT training to onboard employees more effectively?

These are the questions we’ll have to answer as we move forward. The vaccines are on the way, but the way we work is forever changed, and IT’s going to be front and center for years to come.

Key Takeaway

The best IT leaders have always had an “adapt or die” mindset. In the wake of the pandemic, that mindset is a necessity. We succeed by staying curious and searching for creative solutions that turn remote work challenges into positive opportunities.

It’s been truly remarkable to see how much innovation and positive change has taken place over the last year, but there’s still work to be done. We can all continue improving as long as IT leaders and executives prioritize self-reflection, honesty, and the wellbeing of the remote workers that keep their businesses running.