Timebox instead of estimate

When I was at SwingLeft, we had this interesting challenge that I’ve never had anywhere else. I called it “the mother of all hard deadlines” which is to say, the 2020 election. Nothing, and I mean nothing, was going to move that date. It was just reality: anything we didn’t get done before November 2020, we might as well not do. So, rather than approach this as “this is what we want to do, how long will it take?” I approached it as “how many reasonably-sized timeslots do we have, and what do we want to put in them?”

Single team

In places that are small enough, you can get away with just having a single team, which means there’s no blending step. All the

Low trust, low commitment, high expectation

Doing this process successfully requires having the true decision makers materially involved and bought in. Sometimes, you don’t really work in that kind of environment. Sometimes the true decision makers truly have an attitude of “I want what I want, I don’t want to hear about conflicting priorities, I don’t want to participate in the process of resolving those conflicts, I just want you to deliver.”

Most people think they work in this environment, but they are usually, actually wrong. Don’t reach for that explanation lightly. It’s a lazy or low-conflict person’s out. Most of the time, once you do the important and painful work of rolling this out, what felt like that attitude will actually turn out to be stressed out people with low information and low trust doing stressed out things. This process actually fixes this apparent problem, most of the time. So you need to at least try. In fact, more than once, I have seen the rollout of this process lead, at least partially, to the firing of these kinds of executives, due to the visibility this process provides and the way it highlights that executive’s dysfunctional behavior. And that is a win, for you.

But if you really, really try and it still doesn’t work, then a) update your resume and start looking for a new job (seriously) and, in the mean time, b) focus on the transparency part and let go of the prioritization and estimation part. Broadcast what you are planning to do, in what order, and make sure that changes to that order, when they are foisted on you from the outside, are as visible (and tracable to their source) as possible, so that that low-trust executive can go yell at that person instead of at you.