Whose Expectations are Those, Anyway?

This is part 1 of a series of blog posts based on a talk I prepared called Successfully Derailed Product. It’s about the ways in which we define and talk about “success” influence what – and how – we build.


Credit: ToRange

There used to be a joke at a company I worked for that went “how many test frameworks do we have” and the answer was “how many SET5s do we have?” It was “funny” because an SET was a software engineer in test, and to get promoted to Level 5 they would have… written a test framework.

How often have you have seen those kind of things? Where the things that get incentivised for individual success turn out to be a joke at scale? Because clearly when it comes to testing frameworks, more is not better. It’s pretty orthogonal to the goals of testing – which are generally around continually shipping with confidence.

This isn’t to say that promotion processes are inherently bad, or that individuals shouldn’t desire and work towards professional advancement. Just that the processes and goals that we define profoundly affect our organisations, the environment it creates for people who work there, and the things we are able to ship as a result. Your processes define your culture, and your organisational dysfunctions show up in what you ship and when you ship it.

This isn’t to say that goals are bad. Goals are good… it’s well documented that we make more progress when we know what we’re aiming for. But if we set the wrong goals, or we set goals that aren’t compatible, then what? And when we agree on the goals we should be setting… are they supported or sabotaged by our processes?

Let’s talk about what “success” even is. Take a moment, and think about some goal in your life. What is it? (Leave it in the comments or tweet at me).

Do you have something in mind? Now I want you to think about where it came from.

Hard part over: how do you measure it and how do you report on it?

Example 1: I have a goal of increasing the monthly actives in the app. My boss gave it to me. I measure progress on it using analytics and report on it every two weeks.

Example 2: I have a goal of clarifying the “vision” for my team. I got this from my team in various ways – surveys / direct feedback about this being something people want. I measure it quantifiably using surveys, and less quantifiably from the kind of questions that get asked in our monthly townhalls or in the regular skip 1:1s I have with everyone on the team. I report on it quarterly – in that we have a document outlining the longer term plan for the team, and this is how often it gets updated.

There’s a framework by Gretchen Rubin on how people respond to expectations, called the Four Tendencies. She describes it in Better than Before (Amazon) and goes into more depth in The Four Tendencies (Amazon). Essentially, there are four ways in which people respond to expectations.

Obligers respond to expectations from other people. They struggle meeting their own expectations.

Upholders respond to all expectations – including those they define themselves.

Questioners question all expectations, and respond only to expectations they think make sense.

Rebels resist all expectations.

Obliger Goals, 2018

So how does this relate to goals? Well obligers probably got their goals from other people, upholders might be making great progress on things they don’t actually want, questioners are trying to ignore things they can’t make sense of, and rebels are opting out of the very thought.

Meanwhile, obligers often feel unappreciated because they’re so busy putting other people ahead of themselves they can’t get their own stuff done. Upholders don’t understand why people don’t just do what they are asked or say they will do without complaining or asking so many questions. Questioners are annoyed by all the arbitrary things that other people want (and also, ironically, by being questioned) and rebels just want to be free to do whatever they feel like and resent all the interference.

All these things are playing out around us. But a lot of the time we don’t have a way to articulate it so we don’t talk about it.

Currently, I manage five managers, and we started talking about it towards the end of last year, in part because reading the book I realised that I was not great at managing obligers. I’m a questioner, and I was completely mystified by the behaviour of taking on arbitrary things and then resenting them. So you know, an obliger gets overwhelmed, and my response is along the lines of “why are you doing that anyway”, which, you know, they don’t find helpful… and then they feel resentful and I feel confused. It’s great working with obligers because they are so nice and helpful. But because of that it’s very easy for people to inadvertently create expectations and take advantage of them. Meanwhile upholders can lack empathy for people who aren’t as effective. This gave us a shared language to talk about how we are creating and responding to expectations with each other.

On a more organisational or social level, there’s an idea called Campbell’s law.

“The more any quantitative social indicator is used for social decision-making, the more subject it will be to corruption pressures and the more apt it will be to distort and corrupt the social processes it is intended to monitor.”

~Campbell’s Law

Bit abstract, right? A good example of teaching to test. Standardized testing can work for measuring attainment, but once students are taught to pass the test, both the teaching and the test lose value.

You can think about this in terms of promotion processes. You define a system which makes sense, but then people work to the system, and both the work and the system become less useful.

Another place you can see this is the tension around shipping culture and something that might be called a “quality culture”. When you define a process to incentivise shipping, shipping becomes the goal and what is actually shipped tends to become secondary – and not very good. Then in a “quality culture” the quality is the most important thing, and so nothing gets shipped at all…

…But if it does ship, it will be perfect.

Credit: Pixabay

(As an aside, this is why I like to talk about shipping as a habit rather than as the goal itself. I think this is something where release cycles help, because it can force shipping on a cadence rather than shipping specific things).

One way to phrase Campbell’s law is that we work on the definition of the thing. And the result is that definition is probably nonsense.

I find all this pretty fascinating, but what does it all mean? How do these things connect? Well when we define systems, we create incentives – or expectations. Individuals take these expectations and it influences their goals (even if they’re rebels – just in the opposite way).

Essentially – defining systems is fraught with risk of derailment, because teams are not made up of rational actors, but rather: people.

What’s next? A look at the way individuals define success.

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