The Insider - August 2022 (Future of Work edition)

On our obsession with productivity, the medium & the message, and trust in virtual spaces.

The Insider - August 2022 (Future of Work edition)
Photo by Birmingham Museums Trust / Unsplash

Hi everyone,

Welcome to the August edition of the Insider. Do you know someone who would enjoy the Insider? Forward this email to them and they can subscribe here.

I’ve been hesitant over the years to focus each Insider on one topic, preferring it to be a wide-ranging survey of multiple topics and ideas, but I’m trying a different approach to this month’s Insider by making it thematic. Every content block centers on the future of work. Should I do more thematic-focused editions or stay broad?

The Personal Update

It’s been five months since I set off on my sabbatical after Uncharted merged with Common Future. It’s been a restful, creative, outdoors-focused summer, but as we turn the corner to the fall, I want to provide a brief update about what I’m working on and what might be next:

  • Smart Workweek: I’ve launched Smart Workweek, a company helping teams pilot a 4-Day Workweek. Teams get the value of an in-depth consultation at a fraction of the price by tapping into an evergreen course + direct coaching.
  • Quartz at Work: I’m joining Quartz at Work as a guest columnist on the future of work. For all of September, I’ll be writing their weekly newsletter and contributing other practical guides for leaders to build values-driven companies in today’s age.
  • Job search: I am starting to think about my next full-time role and I am looking at tech, and possibly climate tech. Instead of starting a company, I want to join a high-trust, high-honesty team at an inflection point of growth. Either fully remote, or based in Colorado.

On Our Obsession with Productivity

God help us, we’ve entered the age of intense employee surveillance. This stunning article reports on the absurd lengths employers are going to surveil their own staff, evaluating them on inconsequential metrics of online activity, mouse movement, and idleness. Such surveillance technology not only docks pay if you’re not being “productive” at your keyboard, but it also erodes mental health and sows the seeds of mistrust throughout teams. This is what happens when we become convinced that an organization’s effectiveness is nothing more than adding up the productivity of its employees.

In my experience advising teams on the 4-Day Workweek, you don’t work one day less just by getting faster and more robotic. That is a recipe for burnout. You gain an extra day off by getting better at prioritizing and de-prioritizing, by continuously learning and iterating around the relationship between effort invested and results produced.

I can’t help but think this surveillance is being used only by those leaders and managers who actually don’t know how to do the work of 1) setting a small number of truly essential goals for their teams, 2) equipping their middle managers to coach and align their direct reports to achieve those goals, 3) building a culture of trust that boosts retention and gives people the psychological safety to do their best work, and 4) holding people accountable to results they’ve accepted as their responsibility.

Perhaps employee surveillance is just a cheap substitute for doing the actual work of management. Perhaps it lets those in power off the hook. It’s far easier to police performance than it is to inspire performance. It’s far easier to monitor productivity than it is to set priorities. We would rather be productive about things that don’t matter than make the hard choices to prioritize what actually does.

On Trust in Virtual Spaces

It’s probably too soon to draw sweeping conclusions about the long-term implications of remote work. It’s a mixed bag of flexibility, loneliness, convenience, and dysfunction. But from an organizational perspective, I’m curious about how we build high-trust organizational cultures that are also remote. It’s no secret that the interactions in virtual spaces like Twitter and Nextdoor have issues in this area, and I worry that remote work will slow the accrual of trust necessary for teams to do their most important work.

One of my friends is a university professor who teaches one fully-remote class and one hybrid class. He mentioned recently that the students in the fully-remote class are less connected to each other and less engaged in the material. When the learning experience happens exclusively online, he felt like he couldn't take the pedagogical risks necessary to challenge his students and push them out of their comfort zone, whereas there was a baseline of trust in the hybrid class that enabled for a richer educational experience.

If trust builds more slowly in remote-only spaces and if the absence of trust translates into a fragility between people, then I wonder about how that fragility will stand in the way of teams doing work that requires hard conversations, spirited dialectics, vulnerable introspection, and the reconciliation that is inevitable when imperfect humans join together to build something courageous and beautiful.

On the Message and the Medium

We misunderstand media platforms when we consider them simply as neutral conduits for our messages to be distributed. Twitter isn’t just a platform for our tweets; the architecture of the platform dictates the type of message we choose to convey. Twitter forces us to be pithy and reductionist, turning nuanced ideas into fortune-cookie life lessons.

The same is true with other media: encoded in the DNA of television as a medium is a mandate to entertain, and the messages (shows, movies, etc.) built on that medium are infused with this entertaining DNA. Podcasts as a medium invite a more conversational, exploratory message. Long-form journalism as a medium gives permission for the slow building of an argument, while also granting us the space to play with nuance. Poetry as a medium allows us to access the lyrical and metaphorical roots of our message.

The medium dictates the message in collaborative, organizational spaces as well. When all of our interactions with our colleagues are on Slack or over Zoom, then it follows that those mediums are also shaping the messages transmitted over them. I don’t think we’re fully aware of the ways our collaborative mediums — particularly when we spend the vast majority of our time collaborating on platforms that flatten the human experience — are influencing the culture, vocabulary, and practices inside organizations.

I read an article a few months ago about how delivery apps like Uber Eats and DoorDash are commodifying the dining and eating experience, denuding these moments of their rich, multi-sensory dimensions and turning them into something defined by convenience, speed, and price. I think the same thing is happening with organizational cultures when we ignore the ways our mediums are shaping our messages: we’ll wake up one day to find that the rich, multi-sensory experience of organizational culture has been stripped down to its most transactional underpinnings. Organizations interested in cultivating rich, human cultures will need to diversify their mediums not just between virtual and in-person, but by focusing on building elevated moments where the experience itself invites us to show up differently.

Can you help?

  • Do you know of an organization whose leader might be interested in the 4-Day Workweek. Forward this email to them!
  • Upcoming Insiders won’t be focused on the Future of Work, but if you’d like to hear more on this topic, you can subscribe to the Smart Workweek newsletter, here.
  • I’m looking for articles, resources, or people who can educate me on voluntary carbon markets. What have you come across or who do you know?

What I am reading

  • By 2028, three out of four teams will have remote workers. How AR, VR, and the metaverse will shape the future of work. Here.
  • Are income share agreements a radical solution to wealth inequality and the future of the modern salary? The peculiar Russian brothers who are pushing the limits. Here.
  • The performative vulnerability on LinkedIn. How we’re pretending to bring our “whole selves” in virtual spaces. Here.
  • Quiet quitting: the new name for an old habit. What it means for workplaces. Here.
  • Podcast: The office is dying. What does the future of work look like? A podcast with two experts on the workplace.

Something personal

For a long time, my dad has worked out of a small, one-room office five minutes away from my childhood home here in Denver. But then earlier this year, they notified all the tenants that the building would be torn down to construct something taller, with glass windows and higher prices. My dad began his search for a new place, finding a two-room office not far away, and shortly thereafter, he extended an invitation for me to join him. I would have one room where I would do whatever I do next; he, the other to continue doing his real estate and law work, and we, together, would be co-workers for the first time: Benitez & Benitez. For the last few weeks, we’ve started to move in: making joint decisions about everything from furniture to cold brew, and it’s never been more fun to discover that sometimes a move towards the future of work is a move that brings you home, returning you to the people who have been with you all along.


Recovering from COVID,