Cutting or highlighting?

Talking with one of my wise colleagues, we arrived at this neat framing around making decisions. “Decision” is a weird word. My friend Neel tells me that its Latin root is literally “to cut away,” and that recognition that a decision is always about narrowing the list of available options can be both liberating and anxiety-inducing. The interesting bit is that sometimes, decisions aren’t meant to cut away.

As it often happens in larger organizations, we tend to live in the swirl of the short-term and long-term objectives. And it is definitely a swirl: the art of leadership is picking out the right mix. Blend in too much short-term, and we’ll find the team stuck in the corner of a local maxima, overconstrained by its previous choices. Blend in too much long-term, and the team fails to make progress that’s necessary to keep that motor running.

To adjust the mix, leaders decide. A common mechanism here is prioritization: picking a shorter list of things that the team needs to focus on. One approach to prioritization is to apply the cutting mindset, as in cutting the list in half: keep what’s above the line and discard the rest. For example, let’s suppose I want to build an app that is available on both Android and iOS phones, but I want to prioritize iOS users. Applying this cutting mindset, I just forget about Android for a while, break out my XCode and start typing some Swift. Only after the iOS version is shipping do I start looking at the rest of the list. Given how many unexpected turns a typical software project takes, will I ever get to do that? Maybe. Will this approach result in a painful migration or two — or worse yet, the “release polka” where my app always looks out-of-date on one platform compared to the other? Probably.  

The cutting mindset is straightforward and clarifying. Yet, in situations where the rest of the list is still a thing we want to do later, it often leads to inferior choices. In these situations, we need something different. Instead of cutting the list, we want to highlight the items on which we want to focus — while still keeping the rest of the list in mind. With this highlighting mindset, the choices we make take on a different spin. Instead of asking “what’s the next step to deliver <prioritized item>?” we ask “how can we take a step toward delivering <prioritized item> that also takes us closer to completing the whole list?” The thing is, the items on our lists are rarely orthogonal and live in clean separate boxes. More often than not, considering them as a whole reveals opportunities for advancing toward completion of multiple items simultaneously. In my app example, while still focused on the iOS release first, I might consider picking a UI framework that also runs on Android, or at least build my middleware in a way that is portable.

When making prioritization decisions, it’s worth being explicit about the mindset with which you’re approaching, discussing with the team the reason you chose one over the other. Otherwise, despite your desire to highlight, an eager PM might swiftly cut your long-term objectives out of the mix. Or conversely, the team will continue to swirl aimlessly in the ideals you have already forgotten about, from back when you thought you cut them away.

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