Project Management: Cynical Optimism

BookFool is in the process of planning for our upcoming textbook buybacks, which means lots and lots of cooperation and coordination among the Fools. This semester, we appointed a Buyback Traffic Cop (yours truly) whose job is to manage the calendar, make assignments, and update Basecamp and our internal wiki with our progress. It’s project management on steroids.

I was a project/account manager in a past life, so this process brings back memories. Because BookFool is a tight team, I’m not worried about us hitting deadlines. My #1 focus this semester is efficiency and not duplicating effort. An efficient process means we can buy more of your books, which is good for everybody!

(cc) Flickr user Geodog

To me, Project Management is an expression of Cynical Optimism. In theory, project management is inherently optimistic because it assumes you can organize your team to achieve more. But it’s also inherently cynical because you have to be ultra-realistic about setting deadlines, realizing that something always comes up.

For example, if you need to have 150,000 bookmarks printed in time for your manager training, you have to get them to the printer a week before, which means getting 50 PDFs back from the designer a few days before that, which means getting the design brief TO the designer at least a week or two before that, which means compiling the brief before sending to the designer, which means nailing down all details before… (and so on).

When you’ve got a chain of events that complex, the optimist knows it’s possible, but the cynic gets antsy when it’s time to set all those deadlines. The incurable optimist says, “My team is on point. If I need it on Friday, I’ll set the deadline for Friday and all will be well.” The optimist is often disappointed because, as the cynic understands, Something always comes up.

The true cynic says, “Something always comes up. If I need it on Friday, I’ll make it due Wednesday so there’s time for tweaks.” Now, this gradual deadline creep creates problems if you try to do it in secret. People know when something is really due, and if they think you’re padding the deadlines without telling them, they’ll simply readjust the deadlines in their head to accommodate reality.

I prefer the path of Cynical Optimism that gathers the team together and says, “We can do this, guys! However, we know things come up and deadlines need a little room to move, so let’s all decide to set deadlines a few days before we really need things done. But let’s also decide to hit those earlier deadlines because something always comes up.”

Project Management in a big team is one of the hardest things you’ll ever do. However, with a good team and a touch of Cynical Optimism, you’ll have everything running smoothly in no time.