A Jumped-Up Pantry Boy

I’ve practices flat organization in a few contexts: as a small business owner, as an activist, and as an employee. It feels right to me. It feels like the space wherein I’m most creative and productive. But why? Is it a quirk of my personality or personal history? Or am I on to something?

Some of my starting points, off the top of my head:

• People are creative
• People care about each other
• People want to succeed together
• Flat means no capricious authority
• Flat means you decide how you work
• Flat means you have a say in the definition of success
• Flat means you own outcomes, good or bad
• Flat means you solve problems instead of being stuck with them
• Flat means your co-workers matter
• Flat means learning
• Flat means higher expectations
• Flat means nothing is safe from questions
• Flat means decisions take longer
• Flat means decisions are better
• Flat means work is challenging
• Flat means work is meaningful

One of the main barriers many people face with a flat organization is disorientation. Mostly we’re trained in hierarchy, so we’re used to navigating the bumps and dilemmas of a workplace with conventional management. We’ve developed and honed those instincts. Flat organization requires the exercise of some new instincts and judgments, not to mention shaking off some habits. For many folks there’s a steep initial learning curve.

But not for everyone. I’m lucky to have had years of experience working in flat environments. While many folks are steeped in conventional management and hierarchy, many are not. It’s worth observing that people bring different expectations into a workplace, and that no management style is frictionless for 100% of the people in an enterprise. Here are a few experiences that oriented me with flatness:

• Starting my own business. I started a tiny web development/consulting company with my best friend when we turned 18. Went right from college to doing it full-time, figuring out taxes, making decisions about clients and contracts and rates. Hiring (and sometimes firing) a small group of employees. Stuck with it and paid the bills for almost ten years.

• Running for office. I ran for the MN House of Representatives in 2006. That was an amazing experience for a 23-year-old. There is nothing like knocking on doors as a candidate to get the feel for just how precious it is for another person to give you a few minutes to listen.

• Co-founding a non-profit and serving on various all-volunter committees. Motivation and accountability are huge challenges when working with volunteers. But in some ways, I think the paycheck and regular hours can mask just how much these are challenges with paid employees as well.

I am really thankful for these experiences. A few things that strike me, as I reflect on them:

• Failure and unpredictability. It strikes me that I’ve failed to achieve my goals at least as often as I’ve succeeded, despite spending equal amounts of time and energy in all cases. I think I’ve learned that you don’t have to be perfect, and you don’t have to be an expert. Nobody can predict the future. Small business and grassroots politics are both risky endeavors in environments where many of the variables are out of your control. Some humility about what I can actually affect, I think, paradoxically makes it easier for me to go out on a limb.

• Working flat isn’t that different from entrepreneurship. Starting your own business entails a lot of the same challenges as working in a flat organization. Success depends on your initiative and there’s no one else to blame if it doesn’t happen. It’s funny that the entrepreneur is so lionized in this culture, while at the same time strict hierarchy is regarded as a norm for employees.

• All-volunteer projects are great proving grounds. If anyone can just decide to stop showing up, you’ve got to constantly be persuading and motivating the people around you. And finding the ways to work that motivate yourself!

• Success is that much sweeter, and even failure means something special. The worst scenario I can imagine working in is where nothing I do matters. For better or for worse. All of these experiences have meant a lot to me. They changed me in important ways. I think having the sense of ownership that comes with initiative, ownership and collaboration is a big reason why I’ve gotten so much of them.

  I think those are some of the things people need in order to be successful and comfortable in a flat org: opportunities to be trusted, the experience of failure under your own terms, and the chance to try again with what you’ve learned.

“To comport oneself with perfect propriety in Polygonal society, one ought to be a Polygon oneself”
Flatland: A Romance of Many Dimensions

Edwin Abbott’s story is a satirical riff on rigid hierarchy. It’s a literal flat land – as in two-dimensional – but flatlander society is anything but. The inhabitants are grouped into immutable social castes according to their number of sides. But the inhabitants only see each others edges, within the plane they share. Never from above. Only a careful study in recognizing the subtleties of distance allows a hexagon to be distinguished from an octagon. The higher classes are granted this study, while the lower classes are left to hide their confusion behind a blanket deference to their betters.

I think one of the common concerns raised about flat organization is that it is confusing and chaotic. Anyone can be responsible for anything? How is stuff going to get done? Who do I ask about X? How do we make a decision if we don’t know who is “supposed” to make it? How do I know when I can say “no” and when I should compromise?

These are all legitimate questions! Flat organization is strange and confusing, if you’re inexperienced in it. But I ask you to wonder about the conventional, hierarchical organization that feels more comfortable to you. Think about the times when you’ve just gone along with a decision you thought was dumb, just because somebody higher up said so. Think about the times when you were doing work that you know was unchallenging and rote, just because that was your job. Think about the times you had to complete a task in a completely pointless, wasteful way, just because the person who made the requirements doesn’t actually know the work, at all.

How did you cope with those situations? How did you avoid getting too frustrated or confused with your lack of agency to change them? How do we accept them day in, day out? I suggest that it’s simple: we’re raised in hierarchical organization. We’re trained to navigate hierarchy deftly, to “climb the ladder.” We’re taught to accept the inefficiencies and dissatisfaction as natural, and to focus only outcomes like sales, salary and promotions.

In a polygonal society, we’re all polygons. When a sphere visits Flatland, the (square) protagonist is utterly baffled by the notions of three-dimensional space. The novel is a classic expression of the basic sociological impulse: to consider that we might seem just as strange through the eyes of another society as they seem to us.

A little dose of that thinking is necessary when making the leap to flat organization. It means suspending the immediate impulse to dismiss practices as strange, and to be willing to question some of what we have taken for granted as normal about conventional, hierarchical organizations. It’s not always easy or straightforward work.

Of course, the onus is on flatvocates to demonstrate that the benefits of flatness are worth the growing pains.