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8 Feb

The tyranny of deadlines

In an ideal world, no one would have any deadlines. Everyone would have all the time they needed in order to do a perfect job. Weeks would turn into months and months would turn into years, but you'd be okay because you have infinite resources, so who cares.

Of course, things don't fly that well in the real world where you're working... no wait... not you — but people you're working with who are holding you accountable to meet those deadlines — are working under a lot of constraints.

Because when you're at a junior/associate level, you probably feel that your manager doesn't understand how work is done, so they come up with arbitrary deadlines. And you obviously feel they're tyrannical and are preventing you from doing your best work.

So, if you're having a hard time dealing with deadlines, right from estimating them to keeping up with them, and they're introducing needless conflict in you and your manager's life, here are a few pointers around setting good deadlines:

First of all, ask your manager, "Why are you asking me to estimate a deadline? Why do you want to know?"

Managers typically have two reasons for asking for a deadline estimate:
They wish to know how much effort something will take and decide whether it is worth doing or not based on that estimate. Resource mapping, basically.
Something important is hinging on the task being done, so they need to know when you can get it done so that said important stuff doesn't get blocked.
In the first case, they're thinking whether to pursue something or not. In the second case, they've already decided that they want something to get done and now are trying to understand how long it will take.

So, understanding this first is crucial before giving an answer.

If it's the former, you need to ask some follow-up questions around what impact they see this project having and how does time fit into the picture. Because it may be the case that in order to make a project worth it, quality needs to be prioritized over an austere time commitment — in which case, you can relax your estimate and let them know the time it'll take you to do really good work. But if the work just needs to be good enough, you can give a tighter deadline.

If it's the latter case, another set of considerations will arise.

First, the opportunity cost of hitting the deadline. What existing work will you have to sacrifice in order to meet this deadline? Is your manager okay with that?

Second, the opportunity cost of missing the deadline. What is at stake if you default on your estimation by a small/big margin?

Third, what are the dependencies? The margin of error in estimation increases exponentially with every additional dependency. The more the number of people involved and the more sub-tasks this task hinges on, the more your tolerance should be while giving an estimate. And you need to make this clear to your manager.

For example, if it's just you who can see through the task from start to end, you can give a definite deadline.

But if there are 5 more people involved, each with their own set of existing responsibilities, your chances of defaulting on a strict deadline will be much, much higher; failure is almost guaranteed.

Fourth, what are the milestones for this specific project? If the project is such that your estimate might go up to a few months, what are some weekly/fortnightly milestones you can create to keep your manager updated and in the loop?

See, usually, we use the word 'milestones' in the context of progress or achievement.

But here, I want you to treat milestones as markers of impending failure to hit the deadline — as failure is a more probable outcome, at least with large projects with many dependencies.

You don't want to give your manager a 3-month estimate and go at the end of month 3 to tell them you will need another 3 months. If you fail the first milestone at the end of week 1, both you and your manager will know that things are not going according to plan, so you can solve bottlenecks and plan for contingencies in advance. The same applies to all other milestones before project completion.

But if you have a single 3-month deadline with no intermediate milestones or progress gradations, the general human tendency is to procrastinate till the final week.

This is why the most important question when estimating is “Why do you want to know?”

Any attempt to give an estimate in the absence of that is meaningless. If you hit the deadline by working overtime (because you sensed a lot of urgency from your manager) but realize that nothing consequential would have happened even if you missed it, you will stop taking deadlines seriously.

And if you fail to meet the deadline and suddenly your manager reveals to you the severity of this error, once again, it's needless conflict you could have easily avoided by communicating better with your manager and trying to understand the context around the task.

An estimate must take into account both the size of the task, and your uncertainty around that size, and how you combine those two depends entirely on what problem you’re trying to solve, what are the dependencies, and what are the opportunity costs of both success and failure.

The last one is probably the most important question that needs to be answered before you choose to give an estimate.

So, yeah, keep this in mind the next time you're thinking about deadlines.

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