Brave New Work: Are You Ready to Reinvent Your Organization?

by Aaron Dignan

Agility is a mindset, not a tool set. It’s a piece of the puzzle, not the whole thing. It is necessary but not sufficient.

The antidote to the diminishing returns of the status quo is to think differently. Imagine fourteen thousand healthcare workers managed by a headquarters of fewer than fifty people. How on Earth is this possible? It’s actually quite simple. Don’t manage them.

Legacy Organizations are obsessed with measurement, often using it as a form of control—to find and punish weak performance. But when we obsess over metrics, we fall victim to Goodhart’s law, which states that a measure that becomes a target ceases to be a good measure. Why? Because human beings will manipulate the situation in order to move the numbers. Instead, we should think of metrics as guides for steering toward our purpose. If we make an app that has a purpose of helping people lose weight, then average time in app is interesting, but only insofar as playing with the app translates to healthier users.

If we act on customer feedback without judgment, we run the risk of regressing to the mean, to our basest tendencies.

In Greg McKeown’s best-selling Essentialism, he put forth the breakthrough notion of an essential intent, a goal that sits between your ultimate vision and your quarterly objectives. He says that an essential intent “is both inspirational and concrete, both meaningful and measurable. Done right, an essential intent is one decision that settles one thousand later decisions.”

Ask every team in your organization to articulate their essential intent. What has to happen in the next six to twenty-four months to keep us moving toward the organization’s purpose? Share and discuss over drinks one afternoon. Resist the urge to make them all fit together perfectly. Instead, notice and discuss divergence and convergence. Offer everyone the chance to revise and refine their essential intents regularly, and keep them somewhere everyone can access them.

“There is no point in having a 5-year plan in this industry. With each step forward, the landscape you’re walking on changes. So we have a pretty good idea of where we want to be in six months, and where we want to be in 30 years. And every six months, we take another look at where we want to be in 30 years to plan out the next six months.”

purpose is recursive—it shapes us, and we shape it.

Every request for orders from the sailors under his command was met with “Well, what do you intend to do?” And at first they were unsure. No one had ever asked. But in time, they came prepared. “Captain, I intend to submerge the ship.” Marquet would simply reply, “Very well.” He primed his people to think for themselves and claim the freedom and responsibility to run the ship. In the years that followed, the USS Santa Fe went from worst to first, setting the bar for retention, operations, and promotions.

How would we describe our current structure? How do products, services, geographies, functions, skills, and customer segments show up in our structure? What is centralized? What is decentralized? What about our structure is fixed? What is fluid? What about our current structure is causing tension? How would an ideal structure serve us? What benefits would we expect to see? Within teams, how do we approach roles and accountabilities? How does our structure learn or change over time?

Learn Faster. In a truly dynamic marketplace, all winning strategies will have one thing in common: the desire to be faster. Or more specifically, to learn faster. In the 1950s, aviator and military strategist John Boyd created the OODA loop—observe, orient, decide, act—to explain how expert fighter pilots continually processed information in the heat of battle.

Small organizations even over global enterprises User growth even over revenue conversion Initial sign-up retention even over existing user retention Desktop experience even over mobile experience Or: Global enterprises even over small organizations Revenue conversion even over user growth Existing user retention even over initial sign-up retention Mobile experience even over desktop experience

here’s a valuable exercise that will help you see where the wind is blowing: Bring your team or company together in a large room where you have the freedom to move around. Prior to the meeting, collaboratively generate a list of every project, program, and initiative that is currently under way, as well as any fully formed prospective projects that the group would like to see funded and executed in the next quarter. Capture them on large-format note cards or sticky notes and arrange them neatly on the wall or floor. Give each attendee one hundred virtual dollars. You can use Monopoly money, stickers, or even just pens and an honor system. Now ask everyone to invest their money as they see fit. What would they do if they were the sole decision maker for this upcoming period? When all the money is spent, have a discussion about the patterns that have emerged, and allow time for everyone to adjust their investments based on what they’ve learned.

“Two wrongs don’t make a right, but two Wrights make an airplane.”

“You likely have to get management approval for a $500 expense . . . but you can call a 1 hour meeting with 20 people and no one notices.”

Teams that have adopted messaging apps such as Slack have cut meetings by 24 percent. And some have gone further than that.

One-on-ones are often used as a salve for hidden dysfunction.

Great one-on-ones can provide feedback and mentorship, deepen relationships, or give us a chance to collaborate on the work. But if you notice they’re becoming a venue for other unmet needs, pull the rip cord and bring those conversations into the light.

Based on what we heard, we rebuilt the meeting rhythm one meeting at a time, ensuring that each one had a clear purpose and matching structure. We tweaked these formats iteratively, based on feedback, until we had something that worked. Gone were the needless reviews, cross-functional one-on-ones to negotiate and back-channel, and long-recurring meetings that no one could remember the impetus for. What used to take forty-five hours now only took eighteen.

Many forms of retrospective exist, ranging from the simple (mapping highs and lows over the time line of the project) to the more complex (four Ls: liked, learned, lacked, longed for). The best kind of retrospective? The one that happens.

liberatingstructures.com is a fantastic resource for anyone ready to move beyond conventional meetings to something more inclusive and generative. The website, app, and the book that inspired them provide a menu of thirty-three methods for activities such as brainstorming, problem solving, and sensemaking, complete with instructions for how to facilitate them.

In a recent TED Talk, McChrystal shared what they learned. “What we found is we had to change. We had to change our culture about information. We had to knock down walls. We had to share. We had to change from ‘Who needs to know?’ to . . . ‘Who doesn’t know?’ and we need to tell them, and tell them as quickly as we can.”

JSOC’s new guiding principle was “Share information until you’re afraid it’s illegal.”

All living systems, at some level, are information processors. Starve any living thing of information and it will quickly perish.

Every single activity we conduct at work—recruiting, sales, accounting—is dependent on information processing and knowledge transfer. If we can tap into our collective intelligence, we can accomplish amazing things. And so it’s somewhat surprising how little time we spend on our information architecture—our approach to discovering, storing, and sharing what we know.

Data is not information. Information is not knowledge. Knowledge is not mastery. Mastery is not wisdom.

Evolutionary Organizations value and practice transparency. In complexity, as McChrystal and the teams inside JSOC discovered, insight can come from anywhere, but only if information reaches the right person at the right time.

Buffer, the creator of a social media management platform, takes radical transparency to a whole new level, sharing everything with everyone. Its website (buffer.com/transparency) shows employee equity, salaries, real-time revenue, pricing breakdown, funding, values, reading lists, a log of every email sent, diversity metrics, their open-source code, the product road map, and the editorial backlog. Beat that.

When information is optional, accessible, and searchable, everyone wins. Less push, more pull.

Working in Public. When a culture is risk averse and teams lack the authority to make decisions about their work, a funny thing happens to work in progress. It goes underground. Why? Because teams know that if they share incomplete or imperfect work, leadership will likely poke holes in it and question their competence. So we end up with cultures where everything has to be perfect before it’s shared. This leads to information silos that hurt everyone.

Several organizations, including Enspiral, Crisp, GitLab, and my own, have started to host their organizational “code” online.

With all this email changing hands, we should have all the information we need at our fingertips, right? But that’s not the case, not by a long shot. And the reason isn’t that we’re bad at email; the reason is that email is a completely inferior way to share information within an organization. It has three fatal flaws. First, email defaults to privacy rather than transparency. When you send an email, you have to decide in that moment who needs to know. Forget to include people who need it, and they’ll be clueless. Throw caution to the wind and blast everyone, and you’re wasting precious time and attention. Second, email is an information sinkhole. Sure, you might be able to find the email you need when you need it, but what about someone who never got it? What if a new employee joined your team today? Do they get the benefit of the thirty thousand emails buried in your inbox? What if you quit? What happens to all that information then? And finally, email is context free. Every email, regardless of whom it came from or how important it is, lands in your inbox in the exact same way. You want to know what it’s about? You have to read it. If you’re Seth Godin and you’re sending your thoughts to hundreds of thousands of people, send an email. If you’re trying to ensure information symmetry with a thousand trusted colleagues, you need a different approach.

you have to ask yourself, Am I sure no one else would benefit from this discussion? Nine times out of ten the answer is no. Work in public.

Multiplayer software is now a prerequisite for efficient information flow. If you’re already using it, double down. If you haven’t tried it yet, start today.

One powerful way to break patterns of secrecy and rumor is to host a regular Ask Me Anything session with your function, division, or organization.

Many organizations that hold real AMAs have nondisclosure policies around them to ensure that nothing gets out. And when it does (and it will), organizations that value transparency don’t stop sharing. They simply fire the leaker and move on. Traditional AMAs often look to leaders for answers, but I’ve found that opening up the floor so that anyone can answer supports the idea that the best information is distributed. It also creates the space for more interesting conversations if different perspectives emerge in the room. Are you ready to find out what people are really thinking?

One of the most common mistakes I see is teams taking a swing at empowerment before ensuring transparency. What happens? People make decisions without the benefit of crucial information (about intent, strategy, customers, prior learning, etc.), those decisions are subpar, and leadership goes, “See! People can’t be trusted to make decisions.” Avoid this by focusing on sharing early and often. Make it safe. Make it habitual. When shared consciousness is high, everything else gets easier.

What does it mean to be People Positive about information? Recognize that trusting people with sensitive information is worth the risk, even if the occasional breach occurs. Sharing leads to reciprocity, responsibility, and learning. Secrecy leads to distrust and suspicion.

More and better information, and more and better ways to make sense of it, is the source of competitive advantage in complexity.

a recent McKinsey study showed that companies in the top quartile for gender and ethnic diversity were 15 percent and 35 percent more likely to outperform those in the bottom quartile respectively.

A team charter forces the team to answer critical questions about why it exists and how its members want to show up for one another.

While chartering creates clarity about a team’s overall purpose and context, it doesn’t do a ton to nurture deeper and more functional relationships within the group. That’s where the User Manual to Me, first introduced by Ivar Kroghrud in an interview with the New York Times, comes in and takes things to the next level. The idea is genius: what if we each wrote a user manual about how to work with us and shared it with our teams? Suddenly they’d know why we always seem skeptical or prefer to give feedback in person or get so excited about a good pun. How much time and confusion could we save?

At the beginning or end of your next meeting, ask everyone to stop what they’re doing and think for a moment about something or someone they’re grateful for and wish to recognize within the team. Then go around one by one and share. No fanfare, just an honest acknowledgment that says, “Hey, I love the energy you bring” or “You were there for me when I needed support” or “You’re the best designer in the building and we’re lucky to have you.”

The fact that Bridgewater operates under surveillance wasn’t what intrigued me. What intrigued me was why they did it—the principle of the thing. And the principle that drives Bridgewater is “radical transparency.” Founder Ray Dalio and his team believe that if you want a culture that makes great decisions, you need a culture that is growing and learning all the time. So they record their conversations. They challenge one another. They “go back to the tape” the way a sports team might, to study what happened, how they came off, or exactly what was said.

The Bridgewater culture is not for everybody (some might even call it cultlike), but the company’s leaders credit its status as the most successful firm in the industry to their commitment to radical feedback.

We grow when we are stretched, when the challenge before us exceeds our skills and we have no choice but to close the gap. But we can’t appreciate those opportunities if we’re too busy avoiding them.

Talent and skills don’t matter if we don’t have the maturity—the courage and humility—to welcome the conditions for continuous growth. And our ability to do this has a lot to do with what psychologists call the four dimensions of core self-evaluation: locus of control, neuroticism, self-efficacy, and self-esteem.

How do you get people who have been managed all their lives to suddenly self-manage? How do you get a culture that is addicted to planning and control to realize there are better ways to manage risk? How do you get leaders whose identities and egos are wrapped up in status and position to realize that this power is not the source of their value? These questions and dozens more are going to confound you.

so few transformations succeed at all. A recent McKinsey study showed that only 26 percent of transformation efforts succeed in the eyes of the people involved. If you ask frontline employees only, that drops to just 6 percent.

We need a new approach to organizational transformation. We can start by accepting that organizations are complex adaptive systems, not complicated mechanical ones. They are living systems, not machines. They are the sum total of the principles, practices, mindsets, assumptions, and behavior of hundreds or thousands of people.