Eric Garside as CTO at Freshly: how flat should the tech team be?
As a team grows, it is important to add more layers of hierarchy, but knowing when to do this is among the most subtle of the decisions a leader has to make.
When I was writing my book I spoke with Eric Garside, who was head of technology at Freshly for six years and who grew the tech team from four people to 70 people. At one point he had 15 direct reports, which strikes me as a high number, but it gave him deep insight into what the team was doing. Even when there were 30 engineers on the team, none were more than one level away from him. This was during a time when he himself was still close to the technology and even sometimes contributing code.
Of course, things change. As Freshly matured, Garside found himself spending more time interacting with the other top level leaders — the head of marketing, the head of operations, etc. As such, he could no longer spend as much time managing the details of the tech team. At that point, he divided the tech team into two main divisions, and he took the two team leads that he trusted most and put them in charge of those two divisions. In other words, he went from having 15 direct reports to having only two. Having 15 direct reports granted him insight into fine-grained details about the operations of the tech team but it also took too much of his time. He was looking down the hierarchy, but at a certain point he needed to look up. Trusting the tech team to his two lieutenants freed him to spend more time interacting with the rest of the company. This approach worked well for him and for Freshly.
The needs of an organization will always change over time, and therefore your role as a leader will change too. Even the CEO faces the question of when they should focus down the hierarchy and when they should focus up — for the CEO, facing up the hierarchy typically means focusing on the investors and the Board of Directors. I wish there was an easy-to-follow formula that would magically achieve the ideal balance, but in fact this is something that can only be understood through trial and error. Discovering the right level of hierarchy for your organization is an art, not a science, and it is something that needs to be constantly rediscovered as the situation changes. Sometimes you will need less hierarchy and sometimes you will need more, but the only way to know is to keep track of the real needs of your team and to balance those needs against the needs of all the other teams in the company.
Do you want every decision to go to the top?
Some of the advocates of flat organizations have said to me, “So long as everyone acts like a real adult and talks things over with real maturity, then the teams can resolve disputes on their own, without having to take their issues to the very top.”
I suspect that such advocates are subconsciously thinking of family dynamics: if children could act like real adults, then they wouldn’t have to take their disputes to the parents. But that assumes the fight is over something trivial, like toys or clothes or video games. Among professionals, the issues will often be over strategic initiatives, where two options are both valid but each commits the company to a different path. A question like, “Should the database team use a distributed, high write-volume NoSQL database, or a traditional database with a RabbitMQ queue in front of it?” is not like two children arguing over a toy. Strong arguments can be made for either option, but it is a major architectural decision and it will shape how software is developed at the company for many years to come. “Act like an adult” also means “defend your professional opinion based on all you’ve learned over the course of your whole career,” which doesn’t exactly lend itself to compromise on important issues. But somewhere in the system there has to be a leader who can make a choice and then accept all the consequences and responsibilities of having made that choice. So the only real question is, will your company empower mid-level managers to make those decisions, or will every decision be brought all the way to the top?
Again, remember Eric Garside at Freshly. Recall that he had 15 direct reports when the team had 30 people; that’s 15 people he was trusting to make most day-to-day decisions so he didn’t have to think about them. Later, when he needed even more distance from the inner workings of the tech team, he elevated his two most trusted lieutenants and left nearly all the work to them. By all accounts, Garside managed this transition in a pragmatic fashion, without any rigidness about keeping the organization flat nor any particular desire to make it more hierarchical. He simply did what he deemed best for the company. It wasn’t a political question for him, it was common sense.
You cannot build a vibrant, successful organization if you try to follow simplistic slogans such as, “All bureaucracy is bad.” Nor is it valid to say, “All bureaucracy is good.” The only appropriate approach is to figure this out empirically. Remember, this isn’t a political question, this is an issue for pragmatism.