How to bring order to Chaos

This post was originally published on on April 1st, 2020.

Recently, I accepted a part-time volunteer position running the “DevOps” team for the Helpful Engineering group that is dedicated to fighting COVID-19. The group operates in a “swarm” model which relies on self-organization as a key concept in allowing the best projects to both come to light and fruition. There are many aspects of assuming responsibility for a part of a globally distributed engineering organization that mirror exactly the work I do with leaders who want to mature aspects of their engineering organizations as part of my regular work with my clients.

If you are an engineering leader who has the new found responsibility to organize and mature an organization in disarray, whether by design in a swarm model, or without intention as in most companies, think of this as a cheat sheet to achieving sanity from chaos.


There are plenty of books and articles about what needs to be done in the first 90 or 100 days, but sometimes one doesn’t have that long. If I were to wait 90 days before making decisions with Helpful Engineering (which emphasizes rapid response to current needs), the virus would be past its first peak in the United States. People are dying today. Hopefully your situation isn’t as dire. In many organizations there are deadlines that are out of our control such as board expectations, promises made to clients, and other reasons why you also may not have 90 days.

Meeting everyone in an organization can be very difficult depending on the size of the organization. Right from the beginning, it’s important to meet everyone, or at least as many people as possible, and to take good notes on every meeting. At first, people may be uncomfortable with things being written down, so it’s important to explain how it makes it possible to look for patterns in the organization, and how that is the best way to make things better. If the organization is in disarray, people will appreciate that.

Do not only meet with direct reports. Take the opportunity to perform skip-level meetings to get as close to the true information as possible. According to “The Iceberg of Ignorance”, team managers only see 9% of problems! As a new leader in a chaotic organization, one definitely doesn’t want to make decisions while missing 91% of the problems to be addressed. Thus, it is essential to meet as many staff level engineers as possible to have the richest dataset from which to move forward.

Describe expectations

Once you’ve met with the folks who are closest to the information, there should be a good understanding of their strengths and weaknesses. An important outcome should be to have a pretty good understanding of who are the stars and who are the bottlenecks (hopefully in the Theory of Constraints sense). Now is the time to set expectations for the teams. The teams don’t know you and you barely know them, so it’s time for them to understand you as a leader. I usually ask questions about what they spend their time on, what they’d like to be doing, and what is one thing we could change to make things better. This demonstrates that the goal is not to assign blame, but to improve the system.

Being able to define clear expectations for the team will go a long way toward earning the trust of your new organization. For example, one expectation I always try to set is: our work should be focused on meeting business goals, not around making sure that everyone is working 40 hours a week.

Align on axes

If it is necessary to reshuffle the organization, which is likely with the more chaotic ones, it’s important to align teams around a single axis. By this we mean, teams should be tasked with responsibility for a specific value stream.

Often organizations that are chaotic have trouble with delivery and have every one trying to do every thing. Context switching is bad for computers, and it is bad for humans as well. As we’ve discussed, in order to be productive, workers need blocks of time without interruptions. If instead of allowing teams to work on many different things, we organize around the value streams they provide, they will be able to deliver focused work that continually improves and will reduce context switching to a bare minimum. This will help to minimize the chaos which would otherwise result.

An example is how in the Helpful Engineering DevOps group, instead of having all engineers work on everything, we have begun to organize around specialties and interests. We have teams assembled to support all three major clouds, as well as those around specialized skills sets like authentication, architecture, and security. There are also project liaison teams that are assigned to specific projects and who cooperate with the core teams whenever they need to coordinate activity that could be leveraged centrally to the benefit of everyone.

Clear blockers

One of the best pieces of advice I received from a boss many years ago was “If you succeed, I succeed”. There are many possible reasons why a chaotic organization may not have succeeded in the past. It is your job to make sure they have all the resources they need to be successful and as many obstacles as possible cleared out of their way.

It does no good to listen to everyone, understand their challenges, reorganize the teams, and then leave them to deal with their own problems. This is where our instincts toward Servant Leadership have an opportunity to shine. It’s where we get to apply systems thinking and Gene Kim’s 1st way of DevOps to try and optimize the flow of work through the system. Some of this is inherent in our new organizational structures, some of it is inherent in our active participation.

Meet, meet, meet

In the Helpful Engineering DevOps organization, we have daily standup, every day. The urgency of the problems we are trying to solve are too great to do without. This is a forum for people to discuss work that has been completed, upcoming work items, and blockers which need assistance from someone in my position. This meeting is 100% optional. When taking over a new organization, unlike when fighting a pandemic, it’s important not to meet on weekends so the expectation is not that we want people to burn themselves out.

As the structure of the organization is new, and many team members are probably working with each other for the first time. It’s important to over communicate about the fast pace of change happening around them. Too little communication and the rumor mill is easily started.

By applying regular, consistent communication we can ensure a high degree of alignment between all the teams in the organization. This minimizes duplication of work, makes roles and responsibilities clear, and allows each value stream to execute well on their specific area of responsibility.

In Helpful Engineering, I’ve had people inform me that they will write a private document and send it for my review. I’ve emphasized that I consider transparency to be a first class citizen in an all volunteer organization and for the item to which they were referring. It would be better just to share it with the entire team from the outset for feedback (and I will make a point of being one of the people providing feedback).

Save the explosives

Though we are talking about changing the alignment of the organization into structures which most likely never existed previously, this does not mean that it’s important to blow up the entire organization. Part of our discovery process is to identify the solid leaders so it’s important to use those individuals to our advantage!

Unless it is an extremely small organization, it will be almost impossible to keep track of all the different teams, work items, etc. In this case, we have to remember to delegate. If we demonstrate trust in people we can trust, we can save many of the aspects of the organization people can relate to from the previous structure. That sense of familiarity can be powerful to give people a sense of groundedness as they move through rapid change.

Embrace uncertainty

There is no doubt that we are moving through a time of great uncertainty. I’ve always called myself an opportunistic leader because I’ve always seen lots of opportunity in chaos. If we are able to navigate our way through that chaos, we can often find ourselves in a much better place than we were before.

I’m hoping that my experiences navigating chaos will be useful in the fight against a rapidly changing global pandemic. You don’t need to be working in that kind of environment however, to craft your own serendipity.