Late Night Hippo Party & The Setting Of Deadlines

Thanks to an aggressive deadline set by the HiPPO* in charge of his professional life, VIP is still at work at all hours this evening striving to meet an arbitrary deadline, and replacing a mostly acceptable product with a not-quite-finished product. When asked when he would be home tonight, VIP responded “I think I will be home Tuesday.” Since it’s still only Saturday, this answer displeases me.

Why? Why do we get ourselves into this position?

I understand the benefit of deadlines in some cases. They allow multiple members of a team to plan for when resources and people will become available for another project. And they also lead people to prioritize work to meet said deadline.

Unfortunately, just because something has a deadline doesn’t mean it’s actually a priority.

And if something can’t be done in X days, setting a deadline that pleases a HiPPO, doesn’t actually make the work any more possible.

Even having been recently introduced to the formal Hofstadter’s Rule, I don’t understand how it is that we keep doing these things to ourselves. How do I get better at estimating time? And how do I force HiPPOs to do the same?