Ask HN: How do you do estimates in 2021?

The 3 times rule is good, I also apply it quite often, although it's not always an easy sell.

The below is a joke, but sadly it is representative of most teams I have worked on.

If it's like anything that most managers do, you have the team come up with estimates, have some meetings to see if you missed anything, discover that you did, then create a schedule, remembering to add slack time for unforeseen interruptions due to people getting sick, customer issues, etc.

Then you see that the schedule is too long. Slowly but surely browbeat the team into saying "yes" to the question "do you think this can be done faster" on every task. Do this some more when someone from sales asks if something can be delivered in a particular quarter.

Get very stressed out when the real project deliverable dates align much more closely with the original estimate than the unrealistic one. Micromanage your people and stress them out. Keep freaking out as you miss every deadline in the "pipe dream" plan.

Deliver the project with a mild slip compared to the original plan (because you missed something major in the original planning as it is impossible to foresee everything). Use the twice-too-short plan as your metric though. Still, the product is awesome, so give your people a pat on the back.

Hold a "lessons learned" presentation swearing to never do this again. Speak at length about how critical good estimation is. Go on to repeat the very same exercise for your next project.

Just had an idea: maybe keep the version of the timeline from before you haggle down the dates and keep checking which one matches reality better? You don't have to tell the developers that you are doing it if you believe us programmers need some flogging to keep us coding.

The highest performing teams I have been a part of did not regularly do estimates for planned work. That may be the best practice for 2021.

If we had to absolutely deliver by a fixed date - a rarity - we broke the task down in parts that could be estimated, identified the dependencies between tasks, and kept management informed if those dates could slip.

This lightweight process worked pretty well if we had to implement it. There was a lot of trust put in the engineers.

At this point I just make a quick guess and try not to spend any more time thinking about estimation. In my experience, all time spent estimating is time wasted. If there is some hard date that needs to be met, I have the luxury of ditching features that we don't end up having time for. If you're in a situation without that luxury, you have to everything in your power to keep expectations in line with reality.