People on a video conference doing a check-in...unsucessfully.

Remote working is not a digital problem. It’s a human one.

For many teams, the rise of the requirements for dispersed, remote working have been organizationally challenging, to say the least. Maintaining project momentum, employee engagement, and a sense of culture have become top-of-mind pain points for most leaders today.

However, from the work we’ve done inside of various organizations this year, what has been remarkable to see is that teams who prioritized relationships and culture pre-crisis have had the least trouble adapting post-crisis. In fact, many have quickly and creatively found ways to pivot and thrive amidst the ambiguity. Companies who have previously stalled culture investments because of an unquantifiable ROI are now watching as competitors and peers fly past them with very little loss of momentum and a keen ability to pivot overnight. The return on culture is not overtly in the form of revenue – it’s in the form of relationships built on trust, and shared alignment on how to best move forward in the face of challenges — together. Moments like this are when those investments pay off.

In moments of turbulence, the power of your relationships will dictate your ability to survive. The ‘where’ of your work is far less important when the ‘why’ and the ‘how’ are explicitly defined and aligned.

Today’s problems are yesterday’s problems, just magnified.

Remote working is not just a digital problem – it’s a human one. Or to put it more bluntly, if you’re having trouble adapting to an entirely virtual world of work, it might not be the tools that are broken, but rather your team. The good news is that’s actually an easier challenge for you to control as a team leader or even team member.

In the midst of rapid change and transformation like this one, unexpected and unprecedented challenges will certainly emerge, but as a leader your literal job is to guide a group of people through tackling big challenges. This is a a skill-set you are already familiar with. So if you feel yourself doing what you’ve always done — just harder, louder, or faster — and aren’t seeing the results, then you are addressing the wrong root issue.

Times like this create a million reasons to blame for breakdown, but they often also point a magnifying glass on organizational culture challenges that have likely existed for awhile. The bold leaders lean into these moments as opportunities to fix what has been in front of them for awhile. Here’s how.

Focus on your team’s needs, not the rest of the world’s answers.


What you think will help your team. Tactics to throw at a problem. Each are legitimate answers, but if they aren’t tied to a clear need, change won’t happen. That’s why some of these might be high-impact for one team, and no-impact for another.

  • A fancy video chat platform
  • A webinar
  • A training
  • Digital sticky notes
  • At-home computer monitors
  • Pay increase/decrease
  • More/less meetings



What’s actually creating breakage. The challenges and emotions at the root of your team’s challenges. Not always rational or logical, but always human. Identify these, and you can get more focused on the best way to create sustained change in your team.

  • The need for alignment
  • The need to feel connected
  • The need for a guiding vision and voice
  • The need for engagement
  • The need to feel control
  • The need to feel safe
  • The need to feel momentum

The most important thing to do in a moment of crisis is to slow down and assess the situation before jumping to a solution. Check out this great piece from one of our friends and clients at Cisco, Jason Cyr, comparing his experiences as a fire fighter and a design leader which touches on this topic with total bad ass-ery. Abe Lincoln’s famous quote — “give me 6 hours to chop down a tree and I will spend the first 4 sharpening the ax” — seems so obvious, but it’s the moments you need the advice most that it’s easiest to forget it (read: this moment in time right now). When the world is wildly unstable, work needs to keep moving, and everyone is looking at you to lead, there is no doubt you need to make some fast decisions.

Get video chat installed, make sure the team has monitors at home, set up weekly briefings to update org status. These are great solutions and they play an important role in triage, but the greatest leaders recognize those are only solutions to address short term fires. If left to simmer, the real issues will still creep up in a matter of time. The greatest leaders instead take a step back after that first burst of solutions and then assess the deeper needs of their team before jumping to their next set of solutions.

Let’s play out an example that we’ve been seeing a lot lately (and even felt in our team!) — due to the work from home mandate, a leader rolls out a new video chat platform for their team and sees a spike in engagement. But after about a week, people suddenly start turning their video off, no one is responding to open ended questions, and people become less communicative about what they’re working on. It’s clear employee engagement is low again, and what better thing to blame than the new video platform that’s just been implemented. Or you could easily deduce that remote working as a whole just isn’t a fit for your team. Unfortunately you’ve misdiagnosed your problem, and in the process of doing so have written off one of the most powerful collaboration tools of our time and a format of working that’s generally been proven to increase productivity in many cases.

With the right set of tools and questions, leaders should take advantage of these moments to dig deeper with their team, probing them on how things are going and listening deeply about not just their professional needs, but personal ones as well. From the many teams we’ve been working with, what has been underlying most of their work challenges has had nothing to do with technology, but rather a missing a sense of connection within the team. Given everything going on, they’re likely not be capable of naming that for you, so it’s your role as a leader to put on an organizational ethnography hat and probe for these types of needs.

3 Everyday Practices for Identifying The Needs of Your Team (and yourself)

These practices are drop dead simple, but might feel complex because they aren’t habits or conversations that exist in most teams (you have to use your words and your feels — ugh!). They are low-risk, high-reward, and will provide you with more insight than a year’s worth of stand-ups.


These are well documented and widely practiced because of their role in Agile, but they’re more important than ever in trying times like this. They create structure for your team to reflect together on what’s working and what’s not. If you aren’t familiar with retros, check out our in-depth list of retro resources here or our step-by-step guide to run one for a complete how-to guide for facilitating them. We recommend doing them on a monthly basis, but you can turn that up or down based on your team’s needs and culture current state.

The Reverse Roast

We hosted one of these recently and it was pure magic. We ran over by about 2-hours kind of magic. The idea is simple — grab time on your team’s calendar, and about a day before the session send out the same question to everyone and ask them to fill it out for each other member of the team. “You have had a profoundly positive impact on me and my work, and here’s why: ________.” To facilitate the session, you just set some clear time boxes based on the number of people, then name a member of the team and do a rapid fire, popcorn style share out of everyone else’s prepared responses for that person. Tears might be shed, laughs will be had, your team will feel instantly connected at a human level.

Deep Listening Conversations

Perhaps my favorite exercise to lead with almost any team, but especially leadership groups. You can incorporate this as a team ritual across your team members, or you can adapt it as an alternative 1:1 structure between you and each member of the team. Start out by giving them a prompt that will encourage them to share some stories about them. Here are a few of our favorites:

  • Tell me about something you’re wrestling with in their life right now.
  • Tell me about something that’s impacting your day to day right now that I might not know.
  • If you had to remind yourself of one word every day to be at your best, what would it be? And why?
  • How are you doing right now? No, how are you actually doing right now.

It might take a little coaxing to get them started, but don’t push them too much — give them time to get into it. Once they get going, your role is to respond using primarily the phrases in the image above. Avoid talking about yourself, spinning into rabbit holes, or trying to overly relate. The purpose here is to listen, and that is the greatest gift you can give someone. In the meantime, you’ll get a boat load of insight about what’s actually motivating your team’s actions in this moment.

Pro tip: give people a heads up that you’ll be approaching conversations in this way, because it will feel a little different than typical communications. Guaranteed they will feel refreshed and grateful coming out of it, and you’ll have a deeper empathy and understand of the team at a human level, which supports you as a better people leader and work manager.

Andy Hagerman
[email protected]

Andy Hagerman is one of the co-founders and partners at The Design Gym, a strategy and innovation consultancy helping leaders to grow their business by fully unlocking the power of their most important advantage: their people. We work at the intersection of business strategy, experience design, and change management to engage the people that matter most to your work: your customers, your leaders, and your employees. See something that resonates with a project or challenge you're working on? Shoot him a note at [email protected].

  • Terri Sinclair
    Posted at 06:46h, 09 April Reply

    Fantastic post with lots of resources and great ideas! Thanks Andy

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