Ways to annoy your senior engineer

This turns into nickel and diming, then bike shedding. For me, it's easier not to enter the process

The only correct estimation is actually doing the work and looking at how long it took.

The closest to that is half-assing the task at hand and multiplying the time it took by ten. For prototype to actual application, you multiply it by a hundred. This also applies for the prototypes of the prototypes (100x for the actual prototype, then 100x of that for the proper implementation), and yes, those exist, but they are usually named "concepts".

For bugs: Half the amount of time needed for the feature that caused that bug. They need a workaround? It will actually take longer - except when the workaround is already available and just needs to be applied. Then it's 90% of the proper solution.

I know it is quite common, but the culture is the problem. The "leadership" in this piece have interests that are almost orthogonal to that of the engineer. The company is structured top-down, leading to a "it must become true because I said so" mentality, and probably the incentives of the people involved don't align either. Management doesn't have to care about that, because they're not incentivized to. When the wrong people get into that chain, these things happen. And worse too: in other industries, managers regularly override safety concerns.

As a dev who has now gone into management, I fully feel the frustration that you feel about estimate. I was on the "estimates are stupid and pointless" train for a decade and I've made the same arguments you've made here to my managers countless times over the years.

Being on the other side of it now though, I really take issue with sentences like "Estimates are useful to managers and executives to pretend they're in some type of control, but they're otherwise useless". In the places I've worked as a manager, with the managers, directors, and VPs I've worked with, I've never gotten the impression from anyone that it's about control. It's about resource and risk management as well as ROI.

Developer time is a limited and incredibly expensive resource at most companies and managers need to make sure it's used in the most impactful way that it can be. A project may make sense to do if it's going to take a month, but it may not make sense to do if it's going to take a year. Without some sort of estimate on the time a project will take, you can't properly prioritize work. There are absolutely projects where it's just like, we need to get this done no matter how long it takes, but most projects aren't like that.

Again, I totally get your frustrations, but the thing I always tell my teams is let's say you wanted to build a house from scratch. You call a contractor and tell them everything you want done and then ask for an estimate and they tell you, "I don't know. It'll cost what it costs. Every project is different and I won't know until I'm done."

I doubt you would hire them, right?

You need more information than that to be able to truly make a decision because at a certain dollar value it's just not worth it anymore. You don't need an exact dollar amount, but knowing whether it's going to cost $100k or $500k will completely change the value proposition.

Again, I totally feel where you're coming from with pushing back on estimates, but I don't think you're ever going to get away from them. With that in mind, one of the things I've started asking my teams to do where they're really pushing back on estimating is to take a day and think on it and then come back and give me two numbers. Give me an estimate that you're 90% sure is too high and a second estimate that you're 90% sure is too low. I've feel like that takes some of the pressure off because there's no exact number that they can be held to and it gives me enough info to make a decision.

#3 is the biggie, for me (quick estimate).

I used to work for a Japanese corporation, and, when meeting with Japanese managers, you’ll see that they have a small notebook, open on the table, in front of them. Occasionally, they will jot something down in it.

You will also note that, whenever a date is mentioned, something gets written.

You are now being held to that date. They will completely leave you alone, until that date, when they will expect you to deliver “what was promised.”

In my experience, Americans never took this seriously, and it could be a real problem.