End game series vol.3: Prioritising structure & organization in leadership

For folks that have worked with me over the years they know that i’m a bit of a freak about structure and organization. I put a lot of time and investment into processes and ensuring that everyone is following the same process. Much more so than most managers… and have heard from a number of people over the years that i can sometimes overdo it a bit on the process & structure side…. but i do this for a reason. And I consider it part of my general strategy to ‘focus on the end game’ as I have seen this hurt and kill many other teams and organisations.

First, let me put some context on how I became a very structured and organized person

So over the years, and even in my 20’s i was decently organized. I was a strategy consultant, sometimes juggling multiple projects… and had some good, organized mentors to learn from. Also, i’d taken some computer programming classes in university that had given me the framework of how to apply tree-like logic to most problems… and thereby break big, complex problems into smaller and smaller ones.. and then solve each problem as a piece of the pie. But I would say that a lot of other smart people had learned to do the same, and I wouldn’t consider myself necessarily any better.

But the real game changer came in early 2014 when my health collapsed…

Now many people that know me, know this story… but essentially in early 2014 soon after i’d moved to Vietnam I let a dentist, who was a self-proclaimed TMJ expert drill down the cusps of some of my back teeth (because it would improve my situation according to him). And this sent my neck and neurological system into a vicious dive… for reasons that I only really figured out years afterwards.

But from about March until October 2014, my brain literally felt like it didn’t work. I couldn’t absorb or retain information, almost at all… and at the time I had just moved to Vietnam to work at Lazada, had taken up first pure tech role in product management, and had a first child on the way.

It was a near perfect storm.

But as a person who always considered himself a survivor and had already lived in 10+ countries and travelled to 90+, i was bent on trying to hold out for as long as i could. So during mid-2014 i was visiting doctors & dentists 3–4x per week and felt awful.

I tried my best to hold down my job… by literally taking my computer everywhere i went and typing everything that anyone told me. And with the shitty shape my brain was in, i pretty much did not retain anything that was not typed & structured.

So for approximately the next year, i literally had to become the most structured & organized person I knew because i had no choice. My brain didn’t work. So i took copious notes, that i would restructure into a tree-like logic format in Evernote. I created systems for how to organise files, emails, documents, etc. All with the design of minimalizing the need for my brain to retain anything, and being able to call up files and relevant notes quickly.

It was for the same reasons that a blind person learns to have a terrific sense of hearing and touch.. that i became a very structured and organized person that year.

Now onto what I learned from this…

So in mid-2015 i was getting healthier and healthier and was managing more responsibility in Lazada.. taking on ownership of the operations and then marketplace product teams. And basically, as i was learning product myself still while still recovering from a major health incident, i needed systems that allowed me to scale. So i created them. I encouraged everyone to be very organized and set up processes for the team that facilitated this. I also came down pretty hard on people that showed themselves to be dis-organized consistently… and as the folks in that team remember.. i was not shy about this. LOL. I was probably one of the only managers in all of Lazada… that on a weekly basis would literally go around and check how some of his (more disorganized) team members organized their emails, or organized their file bookmarks into a tree-like structure, or ensured that their calendars were clean and up to date.

So despite the large scope and all the challenges, we did what i would consider as being a decent job of ‘holding the fort down’ with a pretty new, inexperienced team on ops & marketplace tech at a time when Lazada was growing very aggressively.

Later on, since then ive been part of orgs / teams where i had less control over the structure and process…. and rather the leadership team was decidedly more ‘flexible’ on these points, allowing dis-organized or unstructured members of the team to do as they wanted. And what i have consistently seen is how this creates cracks in the foundation that eat away at the performance & culture of the team over time… and in ways that are not always clearly evident until you try to scale further on this faulty foundation.

For example, these are things you could often find in a team that allows for some members to be disorganised:

• Documentation of what is built is inconsistent and with frequent gaps. And so teams often do not know what other teams did.
• Team members may not respond quickly to each other on issues they need support on. Or might just respond to the folks that they deem ‘important to respond to..” And so the culture degrades.
• Different teams have completely different processes… some have almost no process (note that i do think it is ok for different software squads to differ in some elements of process, but certain things like how tickets are written, documentation of features, how backlogs are maintained, etc should be consistent in my view)
• The things that are built, typically have problems scaling as there is no set process
• etc.

Now some managers have the viewpoint that it is more important to prioritise speed over structure & organization. I do not.

Managers that believe in speed over structure, often do so in the said desire to just ‘get something out quick’. However I am still waiting for the project that i can clearly point to where this actually worked.. because in my view it pretty much NEVER DOES. At least in software development. If you create a mess in the beginning to get something out quick, you have typically achieved almost nothing.

I think of the quick & dirty software projects with shitty process & structure that were launched in the past 7 years of my memory and pretty much all i remember are things that did not live up to any expectations.. and were typically rebuilt or dumped. With a total consumed effort being much greater than if they’d just used a cleaner process to begin with.

Am I saying that you always need detailed processes right from the beginning? Of course not. I also work in very agile ways… but what i do want, is some documented process that is aligned on. And I want a way of working that is consistent among team members and teams.. so that it is easy for them to cooperate and understand how other teams work.

What happens to an organization with leaders that do not drive structure and organization?

First i will start out with the fact that I often see a lot of leaders who are not great at structure and organization. And rather are very good at other things, in particular communication. Does this mean that they are always going to be a bad leader? Here i would say no.. there are plenty of examples of successful leaders that have done great things. But what you will typically consistently see (based on the ones I have seen) is that they valued structure and organization a lot. And ensured that they had people that were very strong at it in their inner circle driving it.

But when structure and organization are not emphasised, the thing that will often evolve is what i call.. “focusing on what looks good.” Meaning that team members internalize the fact that creating a strong foundation doesn’t really matter as its not valued.. and rather what matters in their org is focusing on the few things that will look good to upper management (ie. putting a check mark against something shiny & attractive). And when you see this.. you know that things with this team are not going to evolve well. Because all of the smaller tasks that do not get the visibility will simply be ignored. And in time you will have put a whole bunch of shiny check marks against projects, but will be sitting on a foundation of quick sand.

So to conclude… focusing on tight structure & organization is the same thing as focusing on the end game

You are putting emphasis on the processes and smaller points that allow you to build a strong foundation. A foundation that needs to be able to withstand all the changes in the people and strategy that will inevitably come. And as any chess player knows, your opening and the structural advantage of castling…. comes in key in the end.