Pit of Success for Organizations

[also reposted by request, from 12/16/2015]

Many years ago I coined the phrase “Pit of Success” for software. People had used that turn of phrase before to mean landing in a situation where their own success was awful, but that’s not how I meant it. What I meant was that that state-of-the art software frameworks were too hard to use, too many potential problems, and it was like having to walk some horribly difficult path to succeed. I wanted success to be as easy as falling into a great big pit, so that instead of saying “gotcha” us framework developers could say “nope, that works too, you win again!”

You just can’t help but fall in The Pit for the win.

I like this metaphor because it’s provocative and it’s geometric. It’s about changing the rules so that people do the right things by default, and so, win in three easy steps:

  1. Use framework
  2. Do obvious/easy/natural things
  3. Profit

I think about many things this way, especially longer term things, like affecting behavior in an organization.

Imagine that systems of your organization are like a complicated piece of terrain. The people operating in the system are little balls rolling around. Victory is some sweet spot in the terrain somewhere. Depending on where Victory is it might be pretty tricky to get there. Maybe it’s up some big hill. Maybe there’s a lot of potholes. Maybe the path isn’t very direct.

If you had a Pit of Success organization, then Victory would literally be this GIANT hole in the middle that you just automatically fall into. You can’t help but win.

Anyone work at a place like that?

Me either.

Here’s the kicker. The terrain tends to get worse rather than better as things get complicated. For pretty simple reasons too. For instance, new parts of the system tend to be based on the old parts. So, say you have part of the terrain that’s full of potholes. Yup, naturally when adding to the system people are going to copy them, making EVEN MORE potholes for people to fall into.

Soon you get a situation where making any kind of progress requires complicated manuals and so forth. Step to the left. Avoid the spikes, don’t break your ankles on any of those holes, roll uphill over two hills, don’t crash into any obstacles, and maybe if you’re lucky you can claim victory.

Now you can either try to make your organization more effective by teaching everyone the rules, and I guess that doesn’t hurt, some rules are probably pretty good, or you can go about the business of making the terrain better. Change the shape of some of those hills so that people tend to roll in the right direction. Move the victory circle somewhere easy to get to. And OMG fill in those potholes so people stop cloning them!

If you do these things, then over time you will tend to get more people automatically going down good paths to success. They might not even know you did it, they just suddenly start winning doing the obvious “downhill” stuff.

I’ll leave you with my favorite Pit of Success metaphor. It’s an apocryphal story about the hamburger recipes of Dean Martin and Frank Sinatra.

It seems Mr. Martin was famous for his excellent burgers and had encoded a fabulous way to prepare them. There were many important instructions which I don’t remember but stuff like getting only the best meat, and getting the right spices, and cooking time, and of course the perfect wine.

Mr. Sinatra’s recipe on the other hand goes like this:

  1. Go to Deano’s house
  2. Ask Deano to make you a hamburger
  3. Drink Deono’s wine.

I’m liking that recipe 🙂

Now if you’re a framework author, or an organizational architect then maybe you’ve gotta be more like Dean but it’s be really nice if pretty much everyone else could be Frank.



I’m an Architect at Microsoft; I specialize in software performance engineering and programming tools.

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Rico Mariani

I’m an Architect at Microsoft; I specialize in software performance engineering and programming tools.