Comment by ryanbrunner | Hacker News Reader

Comment by ryanbrunner | Hacker News Reader

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> Just saying 'give us two months of budget' doesn't take the other party into account, and what they're trying to balance or plan for. I've sat on both sides of the table, and honestly just asking for a budget with no actual commitment to completion feels selfish in my opinion. Discounting their opinion because they're 'business' people and not developers, or treating them like an enemy to fight against won't win you any friends or long term relationships.

The irony is that at least some of the time, a "safe" estimate will actually make the project take longer. Work naturally expands to fill a deadline, and not having a deadline but instead frequent progress checkins with an expectation of foward progress can result in more getting done, because it changes the conversation from "how at risk is the deadline" to "how much happened in the last week and what are the next steps", forcing progress to happen continuously rather than one big bang at the end.

I also often hesitate to give estimates / establish deadlines because it tends to create an unhealthy confrontational atmoshepere, where developers are incentivized to not incorporate feedback or make any changes even if they are the right thing to do, because it would put the deadline at risk (but if they incorprate allowances for these things during estimation it's considered sandbagging).

> a "safe" estimate will actually make the project take longer

That’s probably the most important thing I’ve taken away from software project management techniques - everything they do is hurting them, not me. If somebody insists on shooting themselves in the foot, and they’ll shoot you if you try to stop them, you just sit back and let them shoot themselves in the foot and shrug your shoulders when it happens.

It’s easy for this honest mentality to turn into malicious compliance. If you’re actively fulfilling that prophecy, this won’t just impact a manager or a PM, it will absolutely impact you as well. I’ve seen it happen many times, obviously this goes beyond just being wrong or missing deadlines but eventually it will come back around to bite you.

At the end of the day, these estimates are helpful but maybe not in ways that are intuitive from a developer’s perspective. They’re useful in weighing priorities, judging the uncertainty, and identifying where to fill the gaps in understanding, time-boxing research and scope (e.g. do we really need to spend 6 weeks reading release notes?), and help communicate to outside stakeholders. We see the successes of this all the time with big game releases, product launches, movie releases, etc. It’s a high level measurement of progression and devs need to be a part of that planning process. It gets easier for senior engineers to do this efficiently with experience. It’s not necessarily an exercise that a more junior engineer will a) get right consistently or b) think is valuable at all.

In my experience there's two main reasons that orgs outside engineering / product want estimates:

1. Coordination of external dependencies. Stuff like product marketing, sales training, documentation, etc. as well as sometimes things external to the company like customer commitments or sales commitments. These are for the most part legitimate, although in many cases the deadline doesn't need to be known at the outset of development, and too many of these is a very unhealthy sign.

2. Accountability / improved productivity - This usually manifests as an exec feeling that engineering is running too slowly / inefficiently, and by asking for deadlines (and often compressing them to "push" the team) they can improve productivity. These are almost always in my mind completely counterproductive, and there's much better ways to accomplish this.

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