One of my friends has been given an appraisal objective of identifying ways in which his organisation can get better at estimating.  I was out with him and his team the other day for a few pre-Christmas drinks and we bored everyone else in the group by going over it all again.   For my part, I restated most of my ideas that I have previously posted on this blog. Eventually, the others in the group sucummed and waded in with their views, and and after each said his and her piece we came to a sort of broad consensus. Or at least to a conclusion.  We then ordered a round of glasses of some fiery white spirit, and started talking about something else.

It is my view that you don’t get better at estimating. Builders, decorators, and car repair mechanics get better at estimating. But that is only because they are doing the same thing week-in-week-out. In IT you don’t: It’s not about ‘same’.  Even builders and decorators come unstuck one they start getting involved with the more unusual, highly bespoke projects, as any viewer of Grand Designs will observe.  Once they get into these situations, where they are dealing with the unusual, it becomes a bit more like a software project.

Estimates can be wrong.  Yet ‘wrong’ doesn’t mean there is some deep and meaningful ‘problem’ to be ‘solved’. Getting ‘Better at estimating’ isn’t like improving your Spanish, or improving your tennis serve. We estimate based on what we know. And unlike the other professions I mentioned, our work in IT often  hasn’t a historical precedent. What has happened in the past isn’t necessarily relevant to the job in hand now. Therefore estimates are generally done in ‘good faith’: When or if these turn out to be ‘wrong’,  it isn’t indicative of sinister acts of wrongdoing, ineptitude, negligence, or a subversion of the rules.  There is no organisational or managerial failure. No conspiracy. 

Once we realise this, It becomes obvious that people can’t be taught to ‘get better at it’ either.

So we have two choices.  We can either attempt to ‘get better’, and go through life disappointed.  Or we can accept the situation, and do what we can to deal with it.