Meet Deadlines or Die Trying: A Parallel Between Deadlines and Lean Startup Principles

Never on schedule, but always on time.

–Nas, Can’t forget about you

Our CTO has a set of Programming Principles that he has every engineer at KISSmetrics read before starting the job. They are by no means a set of hard rules, but merely guidelines and a suggested philosophy on how to program… peacefully.

What struck me the most were not the coding sections on unit testing and test driven development (although still very important of course), but a section titled “Don’t estimate in a perfect world”:

…the unexpected always happens. So I recommend you take your “perfect” estimate and then double it. If that’s not working, triple it.

As simple as this advice was, I did not heed it.

I’m currently developing GetDataDriven.com, a suite of free analytics tools (and an inexpensive lead generator, shhhhh…) and want to launch it as soon as possible. Last week, I had the front-end left to code up, something I had no prior experience in.

I felt I had already been going at a pretty slow pace, so in order to not disappoint Hiten and the rest of the KISSmetrics gang, I made a ballsy deadline for myself: I would finish the front-end and have the site ready for production by the end of the week. Big mistake. Here’s three reasons why I was being an idiot:

1. I’ve done little to no HTML/CSS/JS, so I had no idea how long the front-end would take.
2. I did not factor in how much time I would need to learn HTML5/CSS3 and get up to speed.
3. I did not factor in any unknowns that could set me back

My estimate in a perfect world was suddenly turned upside down. Seemingly innocuous things that I expected to take minutes like creating a button took hours to figure out. Difficult concepts like CSS specificity took me way longer than I thought I needed to grasp. On top of everything, I caught a bad cold that made me cough my lungs out as I tried to code early in the morning. Needless to say, I did not meet my deadline.

I realized a few parallels between deadlines and startups.  A deadline is similar to a startup’s business model in that it needs to be flexible in order to account for unknown chaos that you haven’t factored in.  You can make a schedule to predict how you’ll meet your deadline, but like a business plan it won’t last first contact with the real world. Unless you’ve done a nearly identical project in the past, you can’t accurately predict the timing of every piece of your project… just as a startup can’t act like a big company and expect to meet three-year revenue estimates.

Note: This was originally written by Summer TEC Intern Lionel Vital on theTrue Ventures TEC Program Blog.  It was reprinted here with his permission.