What is better: set up underestimated or overestimated deadlines?

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Suppose you are a project manager. You can estimate an effort in days for specific task for specific developer. After performing estimation you obtain some min and max values.

After this you delegate a task to developer. Actually you also set up deadline.
Which estimation is better to use when set up deadline: min or max?

As I see min estimation can result in stress for developer, max estimation can result in using all the time which is allocated to developer even if task can be complete faster (so called Student syndrome). Which other pros and cons of two approaches?

EDIT:

Small clarification: I speak about setting up deadlines for subordinates when delegating the task, NOT for reporting to my boss.

EDIT:

To add one more clarification: I can keep in mind my real estimation, provide to boss slightly larger estimation, to subordinates - slightly smaller. And this questions touches the following thing: is it good idea to provide to developer underestimation to make him working harder?

12 Answers

Is the developer going back into a cave to develop this or is there a good chance of changing requirements over the course of the project? I would think most projects will have a good chance that something won't go smoothly and thus it may be better to try to get the prototype up sooner rather than later.

As for the initial question, I think I'd break this out into a few different outcomes and consider each:

Gross underestimation -> This leads to the problem that there is still a lot of work to do and the manager appears unable to make reasonable estimations.

Minor underestimation -> In this case, either there is an extension, scope gets cut or some bugs are in the release, but this is better than the previous case.

Made the deadline, on time and on budget with quality -> While this may seem optimal as everything worked out, I don't think this is the best result possible.

Minor overestimation -> In this case, there is some breathing room that means either things finish early or some extra work is added. A point here is that this may seem to deliver a slightly better result than the previous case like how some companies will try to beat the earnings estimate by a small amount to do better than expected.

Gross overestimation -> I think this would be the worst case outcome though it is similar to the first in terms of someone being way out of their league in being able to provide a reasonable estimation.

That's just my opinion on each and others may have a different take on it than me.

This depends on project.

Some projects may require fast development and there's no alternatives if deadline is already set and there's no good chance to prolong development. Typical issue: marketing campaign resulting in new service. Such deadline can be enough for normal development, but in some organizations it is so close, that developers work in stress and make many errors that are fixed during production stage. That's a kind of project when developers have to work with topmost effectiveness and they'd better get good reward on success.

Some projects are accurately planned and here you can use all analytics you have: history data, some developer's time metrics on subtasks, calculating risks, etc.

But anyway MAX time shouldn't be used: its the most inaccurate measure that usually leads to even more time taken. And here's a simple reason: when developer just gives away this MAX, he almost doesn't measure. He just gives away his intuition that has very little info at the time. But if he'll spend at least half an hour he'll understand specifics of his tasks, he even may split it into subtask and increase his accuracy. So you can give developer some bias like "hey, guys, just think in what time you would provide stable code here" but send him measure himself. It is good for a job, it is good for a programmer himself.

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