Stories about Software


Prediction Markets for Software Estimates

The ongoing kerfuffle over the “No Estimates” movement is surreal to me.  So before I get to prediction markets for software estimates, I’ll discuss the surreal a bit. Instead of attempting to describe it, which, I can only imagine, would be meta-surreal, I’ll make use of an allegory of sorts.

No Wedding Estimates

Imagine that wedding planners have long struggled with an important issue.  For years and years, their clients have asked them to help pick a date on which it would not rain so that they could have outdoor weddings.  And, for years and years, their predictions have been spotty at best, resulting in irate clients, wet formal wear, and general heartburn.

In all that time, wedding planners have pored over weather patterns and diligently studied farmers’ almanacs.  And yet, the predictions did not substantially improve.  It got so bad that a group of upstart wedding planners met one year in the mountains and authored a document called “The Contingency Manifesto.”  This resulted in an important advance in wedding planning for outdoor weddings: reserving a backup plan not dependent on the weather.


And yet, not all was fixed.  People still wanted outdoor weddings, and continued to be disappointed when it rained, contingency notwithstanding.  They still demanded wedding planners help them figure out months and months in advance whether or not it would rain on a particular day.  And, this is understandable after all — weddings are important.

Quite recently, a group of wedding planners emerged under the hashtag #NoOutdoorWeddings.  Their message was simple: “we can’t predict the weather, so have your wedding inside and stop whining.”  The message was, of course, music to the ears of frustrated wedding planners everywhere.  But some planners and most clients balked.  “How can you tell the clients not to have weddings outside?  They’re the ones paying, so it’s our obligation to facilitate their wishes!”

This schism, it seemed, was irreparable.  And surreal.

  • Why is it necessary for wedding planners all to agree?  Can’t the ones that don’t want to deal with weather contingency just not do it and the ones who want to can?
  • Why can’t people figure out that trying to predict a chaotic system like the weather is a fool’s errand?
  • Why would you ask a wedding planner to make a prediction that could easily be influenced by his own interest?
  • Frankly, if one person is dumb enough to ask another to predict the weather on a day 9 months from now, and the other person is dumb enough to do it, can’t we just agree that the two deserve each other and the inevitable lawsuit?

How Estimation Actually Works Today

Read More


A New Kind of Blog

This comic from The Oatmeal is one of my favorite pieces of internet.  That’s true for a variety of reasons, but one of them is how he explains that it’s much easier to be told what to write than to be given the instructions, “write about whatever you want.”  He’s not alone in feeling this way.  Strangely, when it comes to writing, I find that restrictions on the content are oddly liberating.  And I have a hypothesis that this doesn’t only apply to Matthew Inman and me.  It probably applies to a lot of you as well.

This is one of the reasons that I think it’s so hard for new bloggers to get started.  You build up a bunch of momentum, picking a host, a platform, a theme, etc.  You procrastinate by doing these things, subconsciously terrified of the moment where you sit down, stretch, and say, “everything done — now to produce a little content!”  Because then the next thing to happen is a quick moment of anti-climatic dread as you realize you have no idea what to say.  Self doubt creeps in, and you start thinking things like, “what could I say that others haven’t already said better than I could?”  It’d almost be better if you had a time crunch and content restrictions/parameters.


Well, that’s exactly what I’m proposing. Read More


Employers: Put Your Money where Your Mouth Is

Editorial Note: Since writing this post a couple of years ago, Dave has created a site in pursuit of his goal.  He also interviewed me for it.

I had an interesting exchange on Twitter a couple of days ago with Dave Schinkel. Here’s the most salient tweet:

Read More