Increments of Increments

Enterprise software projects: The Experience

Enterprise software projects generally seem to have semi-"humble" beginnings. You may hear whispers about it in a company All-Hands. Later you get a few questions from your direct manager about some details related to this hypothetical new project. You think for a while, answer honestly, maybe get some follow-ups, invites to a couple meetings, and then you go on your merry way. A quarter or two later the pre-project rumblings turn into actual momentum. You're in a bunch of meetings with a bunch of engineers, a couple product people, maybe even a director. You talk about the same minor details ad-nauseum. Discussions progress, but slowly. The MoSCoW matrix is getting longer and longer, but there's only one letter on every column: "M". You eventually land on a solution that nobody is happy with, but nobody hates it enough to put up any more of a fight about the scope or the timeline or how many pixels wide the search bar should be. There is one thing that all of the engineers agree about though: there's no way in hell this is getting done before the end of the year. But, the Consultants are very optimistic and reassure the project managers that they've succeeded in the past with "much less organized teams". Fortunately your camera is off so they can't see you chuckle at this statement. The vendor tells leadership that they've "got some really cool stuff coming that's made to solve this exact problem" coming very soon. The Confluence doc ends with a list of Action Items, things for "the technical people" to follow-up on, but everyone will forget about it the moment the weekend gets here and their real sprint commitments resume on Monday. The CTO sends and email thanking everyone for the extremely productive week of planning. Amidst the sea of "strategic enterprise alignment" mumbo-jumbo, you piece together that he thinks that the project is bound to be a success, that each and every person's contributions are key to the company's success. You delete this email.

Planning for Q2 starts. You are horrified to learn that the project is indeed expected to launch by the end of Q3. Despite the "enthusiasm" you and your comrades displayed a few quarters ago, the people responsible for making decisions seem to have forgotten discussions even happened. Cue another week-long series of meetings reviewing the exact Confluence doc with very few changes being made. Well, except now everyone is expected to say that, despite what was said before, maybe we could perhaps actually get this massive endeavor done in two quarters if we squint just right at the tickets. Satisfied, the project managers report this up the chain, and an official kickoff is scheduled. You have done this song and dance before, so you are not surprised. A small part of you is disappointed. But you're callused enough to not be surprised. Not even when you learn that neither the Consultants nor the 3rd party vendors have signed a contract to do the work yet.