Why deadline is a good thing

I was having beer with a few coworkers after a long day, when we started to debate wether it was possible to set a deadline for any project. “But I am working on a library that I have no idea how long it will take to finish. We have to cross compile into sever programming languages …”, one colleague said. “Well”, I had a big sip of my Left Hand Milk Stout and asked, “Can you finish in two years?” “Sure … it can’t be that long.”, he said. “Can you finish in one year?”, I followed. “Maybe …”, he was not sure. “Then just set the deadline at the end of 2023, December 22, how about it, it is a Friday?”, I said. “But what about I miss the deadline?”, he was puzzled. “See the meaning of the deadline of a project is not that you either deliver on time or you are fired. We are just throwing a dart to mark the target. Having a target date is infinitely better than not having one. At least we can know how far away we are towards that date.” “Now by Q2 or Q3 we will have a better estimate on the deadline. We can tell stakeholders we will be early or late, either way is fine as long as we communicate timely, keep them informed about our progress.” “The rule of thumb is for a one year project, the room of estimation error is 1 or 2 quarters; for a quarter project the room can be 1 or 2 months; then for a month project the room can be 1 or 2 weeks, so on and so forth. Most projects don’t really have hard deadlines as long as stakeholders are well informed of the changes timely.”, I had another sip, definitely enjoying the creamy dark stout. “But what about we do have a real hard deadline for the project, like for AWS reInvent launch?” He asked. “Project with true hard deadline will require a different kind of time management called working backwards. You look at the deadline date and start to plan when you need to make the public announcement materials ready to go, when you need to get all the software and infrastructure deployed … define the milestones from the deadline to now. Each milestone you meet you will need to recalibrate: are you on track according to the plan or not? Most likely you will be off track in some milestones. That is fine. Can you make up the lost time? What resources or people do you need to be back on track? At some point you might have to make a hard decision: do you add more people to a late project, can you cut some features from the launch to make it a Minimum Viable Product? Or is it possible to delay the launch? But be careful of choosing adding people. If you read the Mythical Man Month book, that approach usually makes the project delivery even later because of the extra communication cost of having new people in the late project.” “Just like death is what gives meaning to life, deadline is an essential constraint for any successful project. All good things in life must have constraints. So deadline is a good thing, use it well!”