Against the Herd With Kelly Monahan

Against the Herd is a podcast where I speak with contrarian leaders and visionaries at the cutting edge of the future of work—and living.?

I had a great discussion with Kelly Monahan, Ph.D. about the state of remote work and what's really getting in the way of leaders fully embracing flexible work models. As Managing Director of the Research Institute at Upwork , Kelly lives and breathes data, so I was looking forward to learning from her about what mindset leaders are in.

A lot of her research is focused on identifying what has actually shifted in terms of work long-term—not just something that we’re reacting to now, but the trends that are poised to become a sustainable human behavior change. Particularly, she is always seeking to understand 1) how the workforce expects to view work, and 2) which technologies are enabling (or hindering) those expectations.

She believes workforce expectations have permanently changed. Kelly thinks we have all craved “flexibility” for a long time, but it just wasn’t something we thought was possible with our typical 9-to-5 commute five days a week. Now, since Covid has proved it is actually possible to work outside of an office, we're living in an environment where we can act and enable a flexible work model at scale. It’s no longer a nice-to-have, but an expectation.

A big caveat, though? We need to be better at figuring out how to get the culture right when adapting to a fully remote or hybrid working environment. The Western Americanized way of working has been built around rational economics: People are self-interested and, quite frankly, they can't be trusted to work when left to their own devices (or second bedrooms or coffee shops). For Kelly, we should be using a behavioral economics approach.?

“If you trust your workforce, you're going to create the culture that allows them to thrive and to be productive regardless of where they're working,” Kelly says at one point during the podcast. I couldn’t agree more. Processes behind your company culture, your day-to-day work, and even your management have a very different domino effect when they are built from trust as opposed to the need to micro-manage. Would you rather invest in and use technology for surveillance purposes or for unlocking creativity?

When I asked what other unique challenges she sees for leaders in a more distributed world of work, she didn’t hesitate to mention async communication. Offices made it much easier to bring people together in real-time when a blocker needed to be unblocked. Now, back-and-forth communication on Slack or waiting for an organized weekly meeting to bring up issues is slowing employees down. I firmly believe that we've over-rotated on organized time together. We’re seeing less “do you mind if we take two minutes just to talk through this problem”... meaning we wait a week to solve it.

There are so many other amazing points Kelly made, but I wanted to end my musings on this one: What if we got it wrong? We accelerate 10 years in the future and everyone is back working in the office full time. Distributed work has failed. Why??

Kelly gives three roadblocks that could have gotten in our own way. One, not having the right productivity measures in place to challenge those C-suite leaders and board members who are more inclined to believe that remote workers are less productive. We haven't experimented and adopted new forms of technology to empower our teams to do better work. The third is something touched on earlier. We HAVE TO get culture and human presence in a remote environment right.

Kelly has a lot of other interesting research points she has gathered over her tenure with Upwork. To hear her learnings on AI adoption and changing performance metrics among other pertinent topics around work, check out the full Against the Herd episode here: https://www.buzzsprout.com/2162318/13420017-kelly-monahan-managing-director-at-upwork-research-institute