Making cross-cutting investments

Over the last few weeks, I’ve been thinking about approaches to influencing projects and teams across a large organization. I framed the exercise like this: suppose I have some organizational currency (headcount!) to invest. How do I nudge project trajectories in the most effective way?

Then, I talked to a bunch of peeps, looking for forces present in this problem space. There are probably many more, but these two piqued my attention. The first one has to do with the term of the investment: do I want to invest in several different things over time or do I mostly want to keep investing into the same thing? The second one has to do with how much control I want to have over the structure of investment: how much steering do I want to do with my investment? Mapping these two forces into thinking space, a few recognizable clusters emerge. 

A good example of low-control, permanent investment is donation. I find a team, recognize that it is doing important work and decide to help them by adding to their capacity to hire new folks. Based on my experience, this is more or less a permanent investment. Withdrawing donated headcount tends to be painful for all parties involved. Nevertheless, if the team’s goals are largely aligned with mine over the long term, and I have no qualms with their strategy, it’s a pretty good fit.

If I want a more temporary engagement, I need a different approach. One is to temporarily augment a team with a group of folks to accelerate a particular aspect of work. It’s exciting to imagine that such a team will drop in and race forth with uncanny precision. However, in orgs that have strong engineering practices and structures, augmentation is first and foremost a matter of learning to follow those practices and fitting into existing structures. “Who will review your CLs?” is the question to contemplate when considering the augmentation setup. They work well in homogenous organizations, when the members know the engineering practices well and are the people who can review CLs. Otherwise, this investment tends to offer less control than anticipated.

To gain a bit more control without permanence, I will likely try to incubate a team: seed it with good peeps, set up a resilient structure to help it stay on course, get it past the early growing pains, and let it go. Variants of this approach are found in research organizations and idea incubators, and I’ve seen it work. In the couple of times that I participated in the process, the biggest challenge was finding the right fit for the graduating team and then shepherding the team through often painful reintegration. At least to me, incubation felt more like an art rather than a repeatable process, but that just might be the lack of experience.

Finally, if I am seeking to invest in the long term while retaining high control, I am probably productizing, or reframing my desire to help in terms of a developer-facing product: a tool, a library/framework, an SDK, etc. This product must be good enough for the teams to want to rely on — and to get results that I want them to get. Note that this end result is a second-order effect (first, they want to use it, second, they produce desired outcomes), which is what makes this approach so challenging. On the other hand, precisely because of the indirection, this approach has something that no other approaches offer: the ability to influence multiple teams. Productizing is typically more demanding compared to others. It takes more effort and capacity to build an effective team that reliably ships a successful developer product and have the resilience to keep an eye on the outcomes I need. That last one is important. It takes just a little bit of stress and firefighting to fall back into the “let’s make developers happy” mode and forget the whole point of the exercise.

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