Aaron Dignan wants to know if you’re doing the best work of your life.

He suspects the answer is "Not yet," "No," or "What even is life?"

In his view, it’s common for people today to feel a sense of disillusionment about their careers. “A lot of the promises that we were given one, two, three decades ago about what work should be and how great being a leader would feel are kind of falling flat,” he says.

That lack of fulfillment isn’t the fault of the individual, or even the company. According to Dignan, it’s because we’re living with the outdated architecture businesses were built on a hundred years ago: good at delivering to shareholders, but no match for today’s demands of transparency, equity, and purpose.

Long before he would become an an entrepreneur, Dignan was your average high school kid, working jobs at Office Depot and the local mall kiosk, experiencing his first brush with the feeling of untapped potential. “[My managers] were only interested in me serving as a cog in the machine,” he recalls. Now, as the founder of the organizational transformation firm The Ready, Dignan coaches corporations on how to avoid making the same mistakes.

Recently, he published his learnings in the book Brave New Work: Are You Ready to Reinvent Your Organization? which takes aim at the underlying assumptions that keep companies clutching at Stone Age ideas of control and outdated tools like compliance, accountability versus responsibility, and method versus principle.

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Q. Your book title references the novel Brave New World, which warns against a dystopian hyper-capitalistic future. Are you optimistic about what’s ahead or do you similarly foresee something equally dystopian?

A. I’m optimistic that we have a chance. In the next decade, the decisions that we make about our institutions, communities, and organizations are going to dictate the kind of future we live in. Everything from inequality, to automation, to globalization, to climate change are all ultimately subject to our ability to come together and solve problems in new ways. We’re right in the eye of the storm. We’re either going have a breakthrough in the next decade that leads to dramatically different outcomes, or we’re going keep doing what we’ve been doing. So, the title is no accident. It’s to say, “It’s now or never, folks.”

"Brave New Work" is Aaron Dignan's latest book on workplace culture. Photo courtesy of Aaron Dignan.

Q. A premise of your book is that what made strong organizations has changed over the last 100 years. What do companies need to realize in order to evolve into the future (or, really, to acknowledge the present they’re already in)?

A. If you look back 100 years, although the world had some big changes around industrialization and after World War 2, markets didn’t change that quickly. There were three networks, two brands of cornflakes. Today, there are 20 kinds of Oreos. We’ve gone from a world where the competitive landscape and its dynamics were so simple and slow to one where they are extremely dynamic, unpredictable, and crowded. Back then, the thing you needed was scale, compliance, efficiency, and consistency so that you could create products that were safe and available broadly. It worked really well to solve the problem of: How do we lift everyone up? How do we make sure there’s enough food for everyone? However, as the dynamic shifted and we mastered that stuff, the challenge became: How do have meaning at work? How do we have greater connection? How do we have inclusivity and equity? What we need today is the most adaptive, responsive, human-centric supply chain. We need the ability to create things that meet our changing needs on the fly.

Q. Is it possible for legacy organizations to move faster, behaving as they’ve always behaved? Is that even the goal?

A. The question is: are we looking for speed or are we actually looking for responsiveness? When people talk about corporate agility, we mistake it for speed. But speed is a byproduct of working in the right way. It’s not the goal. We can all just be faster and do terrible products that people don’t like and don’t work faster, right? Right now, we have leaders at the top who are reacting to all the information that’s flowing up to them and then making a decision that then cascades all the way back down. It takes forever and the information gets distorted by the time it reaches them. So yeah, you can try to speed that up by just yelling at everybody to go faster but that’s not the answer. The answer is to be more adaptive, more agile, more responsive to what’s going on so that you’re sensing more continuously and more pervasively.

Q. What’s an example of how an organization could reorganize to be more sensing versus directive?

A. Every organization has an operating system (OS). An OS is the assumptions, principles, and practices that you put into play. So, the metaphor of “the intersection” is a great example. How do we get two roads to cross without anybody hitting anybody?

The two different operating-system solutions for this example have two different sets of assumptions about people. The lighted intersection with the red, yellow, green light assumes that, generally, people ought not to be trusted, that they need to be told what to do and when to do it, and that we need an elaborate set of signals and controls to manage that behavior. It requires compliance and it does not require a lot of presence of mind. There’s this sort of passiveness to the way you participate in a lighted intersection. If the light’s red, you pull out your phone, check your email, turn on the radio. You’re not present in the space until you’re told what to do and then you jump back in.

A roundabout, on the other hand, has a different set of assumptions: that people can be trusted and need to respond to just a few rules, such as going with the flow with traffic and giving the right of way to people already in the circle. A roundabout leaves room for judgment. And it’s sufficient for it to outperform the lighted intersection in most contexts on almost every measure.

The same thing is true with work. We have a lot more command and control than we need and it’s holding us back. In most organizations, the operating system says on paper “We hire the best people and we trust them and they have these ambitious goals.” And then we treat them like they’re five years old. It’s bonkers.

Q. As the founder of Undercurrent, you led the startup from being an ‘intersection’ company to a ‘roundabout’ company. What was that like to give up that kind of control?

A. Even with people who crave control, my most common experience is that they are actually quite frustrated, stressed out, and overwhelmed with the reality of what it feels like to run an organization that way. That was my experience, too. I was definitely a micromanager at one point and I found it exhausting. It wasn’t sustainable. Even if it did work, it was working in spite of itself rather than because of itself.

What we’re actually asking leaders to do is trade one kind of control for another, one kind of power for another. In the past, you had control through compliance. In the future, you’re going to have control through transparency, social pressure, and responsibility. Does the designer of a roundabout have as much control as the designer of a lighted intersection? I would argue they have more control. They’re getting the outcomes they want more often and more consistently.

Q. In the book, you say you’re not necessarily trying to build a harmonious system. You’re trying to for a better one.

A. Yes, the emergence of what works is exactly what you’re looking for, right? You’re looking for a system that is resilient; that is, enabling and growing and becoming without having to be directed by some hero leader. The thing about the roundabout is it works a hell of a lot better when the power goes out. When the unexpected happens, that system is resilient. When the unexpected happens at a stoplight, it’s complete pandemonium. If you think about financial crises or other things in business that totally uproot the system, if you have the right OS in place, you can be resilient. But if you don’t, it’s a complete nightmare.

Q. Based on your experience working with legacy companies, do you think they’ll be able to embrace organizational shifts like this?

A. It’s not easy to buck the incumbent system and move away from the status quo. There are real risks. There are real challenges and some of those challenges are to our very egos and identities. The good news is it is happening. There are hundreds, if not thousands, of organizations moving in this direction. You can start connecting the dots for shareholders and owners and say, “Hey, we can have our cake and eat it, too. We can have a system that is more human-centric, complexity-conscious, more people-positive and produces better outcomes for shareholders.”

The issue now is how fast can we part with some of the comforting ideas of control and success towards something that’s more aware of the possibilities and more willing to get after these operating system opportunities in order to make better things possible. I haven’t decided the future yet. I’m not optimistic or pessimistic. I’m just straight up worried and invested.

Q. You’re in the sensing zone.

A. Yeah. I know that we’re on the edge of the knife. So I’m trying to sound the alarm that we still have the chance to really transcend all this stuff and to start going to our next chapter. Or we can go backwards.

Responses have been edited for brevity and clarity.