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The biggest obstacle to the future of work

What if I told you there was a dramatically better way of working and organizing that would improve your team’s results, engagement, and adaptivity? If you’re like most people, you’d just shrug and go back to work.

Why? Because we don’t give much thought to the underlying principles behind how our companies work. Sure, we might have some frustrations — some ideas for how to do things better — but we haven’t really reflected on all the assumptions, biases, history, and theory that define our day-to-day reality. We innovate inside the box of the command-and-control bureaucracy that has served us over 100 years. We’re so used to our structures, processes, roles, and values that we don’t even see them anymore.

And this is perfectly normal human behavior. We routinely go about our business without understanding the underlying technology that powers our lives. Few among us know how a combustion engine or a microchip works. Our social technologies (think: management and corporate culture) are no different. We didn’t pick our way of working at all. We inherited it. We mimicked it. We absorbed it through countless interactions over decades. We’re simply not aware that how we do things today may not be the only (or best) way.

Most people are not intentional about their way of working.

In the world of self-organization and self-management, we talk a lot about “changing mindsets” and getting people to adopt “new ways of working.” But given the above, we have to accept that it’s not that simple. We need to make people increasingly aware of their current reality (and the implicit beliefs embedded in it) before we can show them a better way. Alternatively, we can offer them a change that requires no great awakening at all. Here, I’ll lightly touch on the nature of both approaches.

In order for things to change, individuals need to become aware of their current operating system: what it is, why it is, and how it does (or doesn’t) fall short. For this process we often confront a team with these 7 questions:

  1. How does everyone know what to do?
  2. What are the rules?
  3. How do individuals and teams make decisions?
  4. How is authority distributed?
  5. What happens when someone has an idea?
  6. How are conflicts resolved?
  7. How does the system learn and change over time?

As the team answers these questions we ask, “What assumptions are present in these answers? What do these answers say about your culture? Do you like your answers? Are your answers consistent from person to person? Do you have answers at all?”

This meeting is a fundamental milestone, because it’s often the first moment that these questions have ever been discussed safely and openly. From that moment forward they can begin to be intentional about their way of working.

This approach I often refer to as “Slackification,” after the software that has seen a meteoric rise in the past year. I believe an argument can be made that Slack is doing more to change our culture’s way of working than any other theory, process, or tool on the market today. And the best part? Most of the 60,000 teams (and over 2 million daily active users) on the tool don’t even think about how it’s changing their behavior — they just know they like it better than email. They like working this way. It just feels better. Never mind the fact that it promotes transparency and implicit structure while reducing meetings and email. That’s just jargon.

To perform this kind of behavioral inception you need to create what Basecamp (formerly 37signals) calls opinionated software. That means taking some truth — some opinion — about the future of work and baking it into an interface that solves a real problem for users in a way they will understand. Don’t ask them to conceptualize a better way, just show it to them… give it to them. Doing is believing and nothing encourages action like a tool that solves a real problem.

So, if you want to change your organization (or anyone else’s), the first step is to accept human nature. You have a choice to make: will you make people care, or will you make that irrelevant?

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Evolving from business as usual to brave new work will take all of us. Here, we share lessons, insights, personal stories, and hot takes on organizational design, self-management, and the future of work — so we can change how the world works, together.

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Aaron Dignan

Founder @theready and @murmur, investor, friend to misfit toys. Author of Brave New Work and co-host of the Brave New Work podcast.