Contact with Reality
I used to work with a team that struggled to give accurate estimations for their projects. Things were usually off to a factor 2-5x. I struggled to keep stakeholders at bay as delays accumulated and the whole quarterly plan grew later and later.
We tried various things to address this, from switching to a more flexible work flow to providing ongoing re-estimations as the project progressed. The results largely stayed the same: We were not able to even remotely predict when something was done and even rolling estimates helped as they only highlighted how much we had to correct our guesses in the course of a given project.
After several months of struggling, I eventually went back through the data and almost kicked myself when I realized what I saw. I tried to figure out why our initial estimations were so off, what it was in particular that we constantly missed, but I couldn't tell. It was just not clear from the data, because we didn't actually create all the necessary stories before starting the work: We just kept adding more stories as we progressed through the project. One project lead had it all in their head, but there was no actual plan upfront.
I almost kicked myself, because this lack of a formulated plan of action was something I had subliminally noticed several times. But I couldn't put my finger on it until it stared me right in the face.
But plans are useless, are they not?
Plans are worthless,
but planning is everything.
Dwight D. Eisenhower
No amount of planning will ever yield a set of steps that can be followed to a T. And such amounts of planning to even come close are a huge time sink, but don't really add value if you don't work on the scale of NASA.
Still, making a plan is essential, because it makes your thinking and expectation about a project transparent and provides an overview of the expected amount of work. That is an important basis for giving any kind of reasonable estimate at all. Furthermore it gives insight into the short-term road map which is important to some teams.
Most importantly, it allows you to improve.
To tell apart expected from unexpected work, find blind spots and systemic problems that will otherwise be hidden between all the other expected tickets, never to be found. It helps a team reflect on why these delays happen and be honest about things that don't work well.
Nobody actually expects to create plans that survive the contact with reality, but for this team there was definitely room to improve. Maybe for yours, too.