Fractal Leadership
In 1988, Ron Westrum created a typology of three organizational cultures¹, and has since used this classification system to help companies across many industries, including medicine and banking. He identified that cultures ranged from “pathological” (where information is used as a resource in power struggles) to “bureaucratic” (where information flows through rigorous channels — or else) to “generative” (where information flow is more ad-hoc, driven by a shared mission).
In recent years, the field of software engineering has turned its attention to this typology², and many companies³ ⁴ have set a generative culture as the north star for their engineering departments. The promise of a generative team is strong, as it can lead to more efficient work, more empowered employees, and more emergent innovation.
However, a generative culture is hard to create. Even if you’re the head of an engineering department, you can’t make it happen on your own. First, it requires leadership above and around you to let go of pathological and bureaucratic control of information. Second, it requires individual contributors to think outside their boxes and not just take tickets. These two preconditions are not commonly satisfied, but they are necessary.
You may get lucky and find yourself working with personalities that already fit the bill. Or, you may have put in the hard work of managing up and managing down (not to mention, hiring well), and gotten to a point where you’re ready for a generative culture. Congratulations! If you find yourself in such an enviable position, you’ve made it, right?
Alignment is Evergreen
Here’s the bad news: you will never “solve” for generative culture. At its core, generative culture is always a tension between autonomy and alignment. Take a look at Westrum’s characteristics of organizational cultures:
“High cooperation?” Great. “Risks shared?” Sounds nice. “Novelty implemented?” That’s… good… right? Heh. If you’ve been in engineering management for any period of time, you know that’s a double-edged sword.
The fact is, you can have all of these characteristics in your culture and still be a total mess. Your department may be acting like a fleet of boats with everyone happily rowing as hard as they can, yet going in different directions. Just like comp conversations are never going to be routine (try to mechanic⁵ your way out of that one), leadership will always be about alignment, and it’s never going to stop. Put another way, I offer the following premise:
Premise 1: In a generative culture, every leader will have to spend a significant fraction of their time aligning people on (a) a mission and (b) their work’s effect on important outcomes. This is likely to take the majority of the leader’s time.
Say it ain’t so
In my experience, this is not an exciting thing for most technology leaders to hear. Yes, it’s common knowledge for the experienced, but still, I’ve spoken to a number of CTOs and VPoEs who are tired. They feel like they have built a well-tuned department, but then it just keeps slipping out of alignment. They’re back to doing the same clean-up again and again.
It doesn’t stop with CTOs, either. When I say “leader,” I’m not restricting it to people managers. Engineers are leaders, from Staff+ engineers who align a department around an architecture, all the way to Junior engineers who align their teammates on the way they’ve built a feature or used a technology. From these folks, I often hear “I just want to spend more time building things.” There is a balance to be struck, for sure, but to be a part of a true generative culture, even ICs need to accept that a significant percentage of their effort will go towards leading and aligning those around them.
Fortunately, I offer a second premise that relieves some of the toil:
Premise 2: In a high-functioning engineering department, every individual is being stretched and coached in some new direction, and similarly, they are coaching someone else as a backup for their expertise.
Fractal Leadership
These two premises together mean that a generative culture works best when engineering leadership is fractal. Just as in a mathematical fractal, the organization as a whole must work on alignment, its departments must work on alignment, its groups must work on alignment, and so on down the chain. Conversely, individuals must all be growing into a wider scope and taking on responsibilities from the people around or above them.
For the head of the department, this means that you have to embrace your role as the grand aligner, but you can’t take it all on your shoulders. You have to develop the skill in your management team and hold them accountable for it.
For directors (or any managers of managers), this means that you can’t see yourself as distant from the day-to-day work. Your managers likely have a wide range of experiences, and some will “get” the importance of alignment and growth while others will default to servant leadership and ticket-taking. You will need to understand their approaches and their work, and you will need to spot check their teams for the quality of engineer alignment and growth.
For front-line managers, this advice isn’t particularly new. You know you need to motivate your teams and help them expand their strengths. My push for you is to realize that you have to make it your priority. It’s too easy to fall into the role of “roadblock remover,” but that’s where servant leadership falls short. Bringing the big picture to them and making sure they’re growing (even if they’d rather not) is not an afterthought. Carve out time in your 1:1s to push on this.
For engineers, this means that you need to embrace the influence you have on others, even if you’re junior. You may not be the company’s expert on any particular technologies, but your work ripples outward through code, through lessons learned, and through patterns you can share. You can put those ripples to work making the team around you better.
Is it worth it?
For some, there is freedom in being a part of a bureaucratic organization (or perhaps even a pathological org). You can learn the rules, turn the crank, keep your head down, and often make a living. Being fractal and having a high expectation for leading and growing can be exhausting, and it doesn’t always yield predictable results.
Running a software engineering department, though, is like running a factory of artisans. Engineers are always solving new problems and coming up with unique results, but at the same time, we must — together — provide value to our business and our customers as effectively as possible. We also stagnate if we can’t raise our heads, see the big picture, and rebuild the factory as we go.
Ron Westrum puts it best:
In a generative organisation alignment takes place through identification with the mission. The individual ‘‘buys into’’ what he or she is supposed to do and its effect on the outcome. A sense of ownership is a natural consequence of identification with the leaders and the team. Accordingly this person will try harder for and care more about the outcome.
This is the grand promise of building a generative culture, and to get there, we all have to lead, we all have to align, we all have to coach, and we all have to continue growing. It’s hard, but it’s absolutely worth it.
[1]: R. Westrum. A typology of organisational cultures. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1765804/pdf/v013p0ii22.pdf
[2]: Google Cloud. DevOps culture: Westrum organsational culture. https://cloud.google.com/architecture/devops/devops-culture-westrum-organizational-culture
[3]: Drew Vanderriet. How to Build a Generative Culture in an Engineering Team. https://betterprogramming.pub/how-to-build-a-generative-culture-in-an-engineering-team-b5bd83cbed2b
[4]: Dave Kaplan. How to build a generative engineering culture. https://changelog.com/posts/how-to-build-a-generative-engineering-culture
[5]: Rands in Repose. Organics and Mechanics. https://randsinrepose.com/archives/organics-and-mechanics/