President of my employer: how long do you thing it will take to complete x type of migration?

Me: I don't know. We've never done one.

President: well how long do you think it will take based on your experience?

Me: I don't know. I've never done one.

@Charon92 then I would have a gun to my head and still have no idea.
by the way, that goldfish over there seems to have an idea, let go ask it..

@Charon92 as a team leader in an agile environ, I used a nice solution for this problem:
created a 3 day research/estimate task that was used to define, scope, specs, and timetable for a given unknon whatever.
in essence, shutup, and let me find out what needs to.be done, we can estimate based on something other then a wild guess.

@magicMirror I wish they would let me have time to define things like that. Instead my projects often get the combination of what the sales team feels like it should take, and whatever gets the numbers low enough to get the sale. Then they say "hey we lost money on project x". "You didn't account for the research and issues from not knowing how to do this"

@Charon92 @steaksauce : don't make it personal. Make it as inclusive as possible. Avoid using the first pronouns.
Donts: I need more time. I have no idea. I never done this before.
Do: In order to give the client a feasible cost esimate, and look more proffesional, we should....
Never give a "from the hip" answer. always ask for more information about the requriments. Tell the asker that you (asker included) require more info, or the ROI will be negative for this project.

tl;dr : delay, obfuscate, annouy, and never answer the question.

Get this sort of thing all the damn time. It’s because traditional management holds estimation as gospel.

Problem is that you’re damned if you do and if you don’t.

Either you’ve got it way out and you don’t have enough time to get it done, and end up being branded incompetent.

OR

you’ve got it way out and get it done sooner than you said, and you get branded greedy / lazy / as taking advantage.

Occasionally you get the planets aligning and they understand or everything just works to schedule, but yeah, that’s a rarity.

I think this is why we’re so stressed all the damn time.

@Floydian by starting the business :p