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Comment by jezclaremurugan | Hacker News Reader

Anecdotal experience - I've noticed that shipping late by 2 weeks with advance notice to stakeholders is taken way more positively than shipping late by 1 week but informing people late.

This seems like plain common sense and required courtesy but I've been on the wrong side of this from both approaches enough times from both sides of the table - people somehow have a block in sharing the bad news (also because in unhealthy places the messenger is shot - just makes me realize that I'm in a good place).

(In any case the blog actually talks more of sharing the context you are in and not just about sharing bad news early - sharing context is definitely safer and a better approach)

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I don't remember where I heard it but "It is OK to disappoint but not OK to surprise" rings so true. Also, the earlier you know you'll be late the bigger the chance is that additional help can avoid the late delivery.

That's my experience too: as long as you keep people up to date and your updates follow some sort of schedule, late delivery is generally tolerated, especially when it can be seen coming from a reasonably long way off.

I always try to front-load the riskiest and most difficult work on projects for this reason: that way you're never in the situation where everything looks fine until it all goes off the rails at the last minute.

As long as one is careful to head off the "here are 10 entirely new people to help you make up the time" trap (with credit to Mythical Man Month of course).

I've never heard that saying btw but it's a great one, I'll definitely remember it for future use!

Say you're shipping 3 weeks late, then ship only 2 weeks late. Now you've shipped 1 week early.

This is solid advice, also because if you think you’ll be 2 weeks late it is likely that you’ll eventually be 3 weeks late anyway. Delays have a habit of piling up.

What if somebody wishes to cancel after hearing the 3 weeks as opposed to 2 weeks?

For e.g. if they're travelling, etc. Could result in loss of revenue as well.

I'd actually see that as a positive thing; too much money is wasted on the sunk cost fallacy, and having the guts to cancel a project if it goes too far over time / budget is rare enough.

I would argue that it is impossible to form any conclusions here without knowing what the exact specific situation is, but of course what you described is plausible.

This was one of my first real work life "lessons" after college and something that a good manager can really help drive home with junior employees.

Coming from college where deadlines were immutable and professors didn't really care to hear about why some long research paper was taking longer than expected, the idea of telling a boss that you're behind schedule doesn't necessarily come naturally.

Yup, and it's a tragedy. A boss cares about the work being delivered, and wants the end product as a valuable piece of the business.

It's not like school where if one is late, one might as well not even turn it in; even if it's late, it's still valuable, and school doesn't teach that.

slow is smooth and smooth is fast

One of my favorites.

Well you let them know that they might need to change their plans. They have time to prepare and mitigate any issues caused by slip in schedule.

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