Planning, Deadlines, and Disappointed Clients

Is it possible to over plan? The simple answer is yes. For a freelance web business this is a critical issue. Clients expect us to give them fair and reasonable estimates of how long a project should take. and so we should. Somewhere there is a line between dealing with everything as urgent crisis and so finely planned that there is no room for spontaneity. Haphazardness creates its own problems.  And we often set deadlines for ourselves that become very difficult to meet. How does it happen? Do we deliberately lie or is there something more fundamental going on? And more importantly what can we do about it? 

Oliver Burkemann in an article in the Guardian says "Hofstadter's law, conceived by the cognitive scientist Douglas Hofstadter, goes like this: any task you're planning to complete will always take longer than expected - even when Hofstadter's law is taken into account. " Our project management style is to break a project down into tiny pieces - tasks if you will - and then estimate the time it takes to complete each one. Next add them all together to get an overall time frame. I recently estimated a project this way.  On paper, for example, it came out to 20 to 30 hours which I then applied to my known work week - billable working hours average 10 to 15 a week. The project should take two weeks. I then used a trick another consultant taught me early on in my web career. Double the final estimate. (and as I was feeling particularly generous - double it again.) So now I'm leaving up to two months to complete a project that in my head I'm thinking will take a week.

Over the years I've pulled some amazing rabbits out of hats. One project in particular comes to mind where at the last minute I was presented with a list of changes to bring a site into compliance with brand standards. Overnight I was able to complete the work and the site went live on time, on budget. I was told that the internal web marketing department would have taken six months to complete the work. I made some joke about bureaucracy and went on my way. On the other hand on this project where I broke every deadline given to me even though they were given with my full cooperation. Not deliberately but simply out of what appeared on my part to be bad planning. Murphy's Law run rampant.

Turns out that this whole thing has a name - planning fallacy. Humans are naturally optimistic and when we look at a project we tend to be optimistic about how the project will proceed. Or to put it another way, not Murphy-esque enough. The more detail we plan the project in, the more likely we are to underestimate how much time and resources it will take. Eleizer Yudkowsky suggests that the solution is pretty simple: "Just ask how long similar projects have taken in the past, without considering any of the special properties of this project."

In the future then ask yourself or an experienced outsider how long roughly similar projects have taken and go from there. For example consider the 20 to 30 hour project mentioned earlier. I have done several similar projects and on average they take four to six months. Had I used that information to realistically set deadlines my client would have been much happier.

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