Delusional Optimism and When to Delay Your Project
The subtleties of when exactly to push back a project’s deadline
Let’s say you have the power (or strong influence) to update the deadline for a project. Perhaps you’re the team’s Manager, Project Lead, Project Manager, or the senior person on the project team. You get the idea… And let’s also say this project has been going on for weeks now when you realize, earlier than everyone else, that there’s no way this is finishing on time.
I have seen this happen a lot. I have run team projects for over 15 years as an Army leader while deployed overseas to Iraq and Afghanistan, as a Tech Lead in corporate IT, and as a Project Lead and Engineering Manager at a tech company. These days, I occasionally lead projects and evangelize project management fundamentals to my fellow software engineers as a work hobby.
Okay, so, when do you decide to update your deadline and tell the team? Most people make the change the moment they conclude that the deadline is unrealistic, but I would like to propose a refinement to the timing.
Because there’s a psychological magic to deadlines that sharpens a team’s engagement and execution in a project. This is even though, in the grand scheme of Life, the Universe, and Everything,¹ this project’s contribution to society is insignificant. Like, when you’re that kooky old man or woman at the end of the bar, you’re not going to say, “43 years ago, on this day, while the glaciers were melting and the world was at war, I launched my project to streamline our inbound sales leads by 5% ON TIME! It was a proud moment for humanity!” For some reason, people still take deadlines seriously and are even delusionally optimistic about their chances of hitting that deadline.
Anyway, when you push back a deadline, people often relax and don’t put in their best effort, so here’s the main idea:
Within the cultural boundaries of your organization, you should hold onto a deadline as long as it gives the project team a sense of reasonable urgency and they are still delusionally optimistic while not unacceptably damaging their morale or trust in you.
Let’s break down the parts in boldface.
cultural boundaries of your organization
Every company or organization has a culture that influences how work is done. At Yelp, my current company at the time of this writing, we’re somewhat relaxed about our deadlines in the Engineering Department. We prefer to build reasonably good software over hyper-focusing on a date we essentially pulled out of our asses at the beginning of the project. In this case, obsessing over when to move the deadline is less productive since people don’t take deadlines seriously anyway.
On the other hand, some corporate cultures are Very, Very Serious About Deadlines (I’m sorry if this is you, especially if you’re in software development). This tactic is more helpful in this case, but if your organization is on the extreme end of this cultural spectrum, then people are already stressed out, and I would not recommend pushing this too far, as you may irreparably damage morale.
Wherever your company is on this spectrum, you must understand how your organization’s culture informs your choices.
reasonable urgency
Your team derives part of its intensity and efficiency from the impending deadline, but this should not be taken too far. I would never, in any situation, ask a team to push all the way until, say, the very day or hour before the project is due and say, “Ah, okay, I guess we won’t make it. Let’s push back the deadline.” At some point, people start cutting corners, making mistakes in their haste, and so on. Also, it’s just not nice, and your team will resent you.
delusionally optimistic
This is the state where, at the weekly status meetings, the team develops this creeping feeling that mayyyybe the deadline is unrealistic. But everyone’s got their role, so they go heads down and keep going. The most delusional are the people who lack discipline and are perennially late to things in their lives (i.e. most of us) and say things like, “This will just take two minutes!” or “Let’s stop by X on the way to the airport, we totally have time!” or “I guess I’ll just come out for one drink.”²
This delusion could last hours, days, or even several weeks. How long likely depends on their trust and faith in you, as well as any cheerleading you do to draw this out. However, once they collectively dispel this delusion, it becomes hard to maintain intensity, and you will need to announce the delay.
Also, don’t buy into the delusion yourself. It’s seductive, but you need to be the clear-headed leader who actually sees the forest for the trees. It is essential to see the big picture before the team does and push the deadline back well before the rest of the team psychologically gets there while still leveraging some of this period for productivity. If you wait until it really starts sinking in, astute team members will later ask, “Why didn’t you push back the deadline sooner? Why didn’t you realize what was happening instead of stressing us out with this unrealistic deadline?” Lastly, on an ethical level, you want to be kind to your people and not damage their morale overly much, which brings me to the last point:
unacceptably damaging their morale or trust in you
The more you push a team, the higher the chance they will break under the pressure, resulting in burnout, meltdowns, quitting their jobs, etc. You don’t want this kind of damage on your conscience.
Also, once they are past their delusional optimism, and it completely sinks in that the deadline is unrealistic, it becomes absurd not to push back the deadline, and you will look foolish for not doing so. At this point, they will struggle to be productive under your leadership since you will have lost some of their trust and faith in you.
Conclusion
Admittedly, in corporate life, there are much bigger issues at play (like, your project is late), but in terms of getting your team to execute just a wee bit more efficiently, I think sometimes it makes sense to fine-tune the timing of when you push back a deadline. Take advantage of delusional optimism (within reason) and keep your team motivated.
Let me know your thoughts in the comments, especially if you’ve had to make this call!
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¹ Douglas Adams, The Hitchhiker’s Guide to the Galaxy (London: Harmony Books, 1979).
² Iliza Shlesinger, “Party Goblin,” YouTube, 07 December 2019, https://www.youtube.com/watch?v=NRprg-IhYRs, 1:22. (This is actually an excerpt from a Netflix Comedy Special)³
³ Iliza Shlesinger, “Iliza Shlesinger: Confirmed Kills,” Netflix, 2016, 2:13.
