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.

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10 Responses

  1. The description perfectly matches the work place of my former employer. From 100 people, when I started, to 450 people when I left. The transition is still happening. They are still evolving. It was a very painful process while I was there.

    I think that’s the only thing not conveyed in this post: It can be very, very difficult for the Old Guard to realize they are preventing the scale they desire.

  2. I’ve seen companies go through more than one iteration of this as they passed through several stages of growth. The company I’m with now hired me as a New Guard of sorts and I was Employee 35. I expect I’ll be Old Guard when we cross some future growth transom.

  3. I’ve seen this time and time again. As you pointed out discussion is the key to solving differences.

    It’s a hard position to be in. As the Old Guard, when you’ve had the long nights and fought all the early battles, you might feel apprehensive when the New Guard starts questioning your methods and poking holes in your logic. The New Guard needs to be careful as well, because unfortunately, the company and the product as it stands today was created through many decisions; some ad-hoc, some well though through. You owe it to your new company to understand the history of the status quo.

    The hundred million dollar question is finding a solution to ease the integration of the New Guard. As a company, once you’ve decided you need to hire, you have to integrate the new person and all of their collective experiences.

    Thanks for the great post. It codifies some thoughts I’ve had on this topic.

  4. Maria Loughlin 2 years ago

    Great post. I’m glad I read all the way to the end to get the point that recognizing the values of the Old Guard while scaling a company is critical to success.

  5. I’ve seen this go full circle, where the old guard wanted velocity, the new guard brought in so much process to “protect what they had” that the newer guard are often dumb founded by the endless discussions about things that are likely to be inconsequential in the long term, and the willingness to embrace things that will change the company for the better are ignored or ridiculed. But then maybe that sound like the “old guard” at the start of this post…

  6. For fuck’s sake… why isn’t this blog post read by every business on the planet? I literally sat here in the back room waiting for my wife’s minivan to get fixed at the local service station and caught myself physically nodding in agreement as the others in the small, stuffy room eyed me nervously…

    Thanks for this. Sharing it to every human being i know.

  7. Andrew 10 months ago

    What have you done to improve the Old meets New paradigm? I’m in a newly formed team of three New Guards tasked with building process but with a mandate for simplicity. Any Old Guards with feedback on what they wish the New Guard had done, or that the New Guard did well? Any New Guards have good ‘Aha’ moments?