Management Comfortable chaos into legitimate chaos

The Old Guard

Dunbar’s Number is a favorite blunt diagnosis for the pains that affect rapidly growing teams. The number, which is somewhere between 100 and 250 describes a point at which a group of people can no longer effectively maintain social connections in their respective heads. What was simple from a communication perspective becomes costly. What was a familiar family that you saw wandering the hallway becomes Stranger Town.

It resonates. It intuitively feels right that we have a threshold for the number of relationships we can maintain in our heads. If your team or company is rapidly growing, it’s worth thinking about how you’re going to help the team feel connected, but I think there is a more interesting emergent behavior during rapid growth, and it’s led by The Old Guard.

They Won

Here’s the poetic origin story of The Old Guard:

A small group of inspired people has an idea, and just about everyone tells them the idea is really stupid, but that’s exactly the same response to the idea that they hear every other day. This small group ignores these naysayers and doggedly pursues the idea, even though on a daily basis it feels like the world is specifically designed to prevent them from succeeding.

It’s a war. The small group is at war with conventional wisdom; they are at war with every comparable startup that is remotely in the same space. But, most importantly, they are at war with themselves. In addition to fighting to bring the idea into the world, they are fighting amongst themselves.

Each day, this small group is learning who they are as part of their struggle to survive. They are learning each person’s strengths and weaknesses. They are figuring out how each person communicates, and each of these essential lessons is learned under the constant threat of irrelevance. These lessons are hard earned – some folks don’t make it – and those who survive this period of painful definition are tightly bound together. They share the same mental scars and they tell the same stories because they have an intimate shared history.

And then the Old Guard starts winning.

The New Guard

After years of struggling, the dream that became the idea becomes the business. A corner is turned and the question changes from, “Are we going to survive?” to “How are we going to scale?” As part of this acceleration program comes the arrival of eager new faces who have heard the stories of success in the face of adversity. They are inspired by these stories and they want to figure out how they can help.

When the New Guard shows up, they notice, well, beautiful, beautiful chaos. Ideas are coming from every direction, decisions are collaborative and high velocity because the team is small enough that you can efficiently ask everyone’s opinion. It’s intoxicating. Execution is shared and terrifyingly fast because there is little desire to bicker. Most everyone still believes they are on the brink of disaster. That’s mainly because they’ve lived in this world so long.

The organization of the Old Guard is instinctively flat. There is rapid and organic error correction because everyone has line of sight on everything. The cost of gathering situational awareness is low because the Old Guard has borderline mystical abilities to figure things out. This is because they’ve got a near-complete mental catalog of the people, their knowledge, and their abilities.

The Old Guard has recognized experience, but more importantly, each day the Old Guard demonstrates to the New Guard that they have instinct. They can rapidly make important decisions with the barest of facts and they have a sense of urgency motivated by their deeply rooted belief that this is the home that they built with their hands and, again, they believe this precious thing could be destroyed in a moment.

The Old Guard’s instinct is well earned and essential, but instinct doesn’t scale without help.

New Guard Friction

The divide that is created between the Old Guard and New Guard is interestingly paradoxical. See, the Old Guard recognizes there’s simply too much to do and there is no way the expertise now needed to evolve is under the roof. The problem is these new hires are a cure to a disease that the Old Guard both created and loves. I’ll explain.

The Old Guard hires eager people to build more amazing things, but each additional human creates a growing knowledge and communication tax. The team needs to spend time to make sure each new person understands the company, how things are done, who is responsible for what, and they eventually need to know their responsibilities. Pretty simple, right? Standard on-boarding, right? What about when it’s 10 people? Or 100? Multiply all their educational and communication needs with the fact that each of these new folks is going to add their own unique signal to the communication tapestry, each person is slightly altering the culture simply with their presence, and, oh yeah, everything is going to change in six months anyhow because the team is growing so fast.

The addition of these new people to the existing population transforms the comfortable chaos into legitimate chaos. Decisions start to happen more slowly, responsibility and ownership become opaque, execution becomes stove-piped, and work is duplicated because the organism has likely crossed Dunbar’s number. Situational awareness has become expensive because learning can no longer occur via osmosis.

The New Guard, armed with their new hire spirit and their lack of historical organizational instinct, starts on important work that the Old Guard both desires and hates at the same time.

The New Guard:

  • Starts to write things down both for themselves and for those who will come after them.
  • Sits down with different teams and agrees to contracts on how they will get work done.
  • Imports language from prior companies to support and define their various emerging causes. This language often comes in the form of important sounding, but equally mystifying, acronyms.
  • And they do a lot of this work via the scheduling of meetings.

The Old Guard’s healthy network of informational sources inside of the company (who are also primarily Old Guard) provides an increasingly worrying diagnosis: the New Guard is creating a lot of process that smells like big company bullshit. The Old Guard worries: they worry that all these eager new faces in their company are fundamentally changing the culture.

Here’s the rub: The Old Guard can’t scale their company without the help of the New Guard, but the Old Guard’s instincts about what works in this particular organism are based on lessons from the past rather than the requirements of the future. When the Old Guard is tested, when something goes sideways in the company, they fall back on what has always worked in the past, and while this strategy feels familiar and fast, it might not allow them to scale.

A Culture Quandary

The critique of this time of the rising power of the New Guard and their increasing skirmishes with the established Old Guard manifests in different ways: “We’re moving slower”, “I don’t know what’s going on”, “We feel like a big company”, or “We’re forgetting who we are.”

In order to build a healthy company that scales, you’re going to need to build infrastructure and process that is going to connect the various parts of your company. This work is going to feel heavy and unnecessary to those who’ve historically been able to do this work effortlessly and instinctively.

It is entirely possible that too much process or the wrong process is developed during this build-out, but when this inevitable debate occurs, the debate should not be about the process. It’s a debate about values. The first question isn’t, “Is this a good, bad, or efficient process?” The first question is, “How does this process reflect our values?”

The largest battles that I’ve seen at prior companies between the New Guard and the Old Guard exist because the Old Guard has not effectively documented and shared the values that the company embodies. This creates the following dialog:

  • Old Guard: I feel this process is heavy.
  • New Guard: I’ve seen this process work at a great many companies and here are the metrics to prove it.
  • Old Guard: Yeah, something doesn’t feel right.
  • New Guard: What the hell does feel have to do with it?

What is missing from this dialog is a discussion. The process feels heavy because in this particular hypothetical company, we value velocity over completeness. Whether they’ve written them down or not, the Old Guard embodies the initial values of the company and when they say, “It feels off…” what they are poorly articulating is, “This process that you’re building does not support one (or more) of the key values of the company.”

The Old Guard is the cultural bellwether of the company. I believe that culture is a slippery thing to fully define, but I do believe it is the responsibility of the Old Guard to not only take the time to define the key values that are the pillars of that culture, to communicate the nuance of those values over and over again, and, lastly, when it becomes apparent they are no longer serving the company, they must be willing to let those values evolve.