You Want an Estimate? Give Me Odds.

I was asked recently in a comment what I thought about the “No Estimates Movement.” In the interests of full disclosure, what I thought was, “I kinda remember that hashtag.” Well, almost. Coincidentally, when the comment was written to my blog, I had just recently seen a friend reading this post and had read part of it myself. That was actually the point at which I thought, “I remember that hashtag.”

That sounds kind of flippant, but that’s really all that I remember about it. I think it was something like early 2014 or late 2013 when I saw that term bandied about in my feed, and I went and read a bit about it, but it didn’t really stick with me. I’ve now gone back and read a bit about it, and I think that’s because it’s not really a marketing teaser of a term, but quite literally what it advertises. “Hey, let’s not make estimates.” My thought at the time was probably just, “yeah, that sounds good, and I already try to minimize the amount of BS I spew forth, so this isn’t really a big deal for me.” Reading back some time later, I’m looking for deeper meaning and not really finding it.

Oh, there are certainly some different and interesting opinions floating around, but it really seems to be more bike-sheddy squabbling than anything else. It’s arguments like, “I’m not saying you shouldn’t size cards in your backlog — just that you shouldn’t estimate your sprint velocity” or “You don’t need to estimate if all of your story cards are broken into small enough chunks to be ones.” Those seem sufficiently tactical that their wisdom probably doesn’t extend too far beyond a single team before flirting with unknowable speculation that’d be better verified with experiments than taken as wisdom.

The broader question, “should I provide speculative estimates about software completion timelines,” seems like one that should be answered most honestly with “not unless you’re giving me pretty good odds.” That probably seems like an odd answer, so let me elaborate. I’m a pretty knowledgeable football fan and each year I watch preseason games and form opinions about what will unfold in the regular season. I play fantasy football, and tend to do pretty well at that, actually placing in the money more often than not. That, sort of by definition, makes me better than average (at least for the leagues that I’m in). And yet, I make really terrible predictions about what’s going to happen during the season.

At the beginning of this season, for instance, I predicted that the Bears were going to win their division (may have been something of a homer pick, but there it is). The Bears. The 5-11 Bears, who were outscored by the Packers something like 84-3 in the first half of a game and who have proceeded to fire everyone in their organization. I’m a knowledgeable football fan, and I predicted that the Bears would be playing in January. I predicted this, but I didn’t bet on it. And, I wouldn’t have bet even money on it. If you’d have said to me, “predict this year’s NFC North Division winner,” I would have asked what odds you were giving on the Bears, and might have thrown down a $25 bet if you were giving 4:1 odds. I would have said, when asked to place that bet, “not unless you’re giving me pretty good odds.”

Like football, software is a field in which I also consider myself pretty knowledgeable. And, like football, if you ask me to bet on some specific outcome six months from now, you’d better offer me pretty good odds to get me to play a sucker’s game like that. It’d be fun to say that to some PMP asking you to estimate how long it would take you to make “our next gen mobile app.” “So, ballpark, what are we talking? Three months? Five?” Just look at him deadpan and say, “I’ll bite on 5 months if you give me 7:2 odds.” When he asks you what on earth you mean, just patiently explain that your estimate is 5 months, but if you actually manage to hit that number, he has to pay you 3.5 times the price you originally agreed on (or 3.5 times your salary if you’re at a product/service company, or maybe bump your equity by 3.5 times if it’s a startup).

See, here’s the thing. That’s how Vegas handles SWAGs, and Vegas does a pretty good job of profiting from the predictions racket. They don’t say, “hey, why don’t you tell us who’s going to win the Super Bowl, Erik, and we’ll just adjust our entire plan accordingly.”