Company Culture and Managing Freedoms

February 9, 2014. Filed under management 130 software-engineering 15

Forty years ago Roger Miller (and later, much more famously, Janis Joplin) sang:

"Freedom's just another word for nothing left to lose."

giving us yet another peculiar entrant towards defining freedom. Perhaps it's nothing more than an apologetic ode to dispair: law requires consequences, and there are no consequences when you've already been reduced to nothing.

Lousy hooks and confusing segues aside, the topic for discussion is the relationship between a company's culture and its freedoms. Rather than starting down the path of examining the kinship of freedom and consequence–which is a rather dismal place to begin anything–we instead look towards kinds of freedom, which immediately brings us to the distinction between positive and negative freedoms.

Positive freedoms are your freedom to do: to vote, to wear the clothing you want, to own arms, to blow smoke into your neighbor's porch when they're trying to read a book outside on a sunny day. Negative freedoms are your freedom from: not to be forced to take an impossible literacy exam before being allowed to vote, not being forced to wear clothing you dislike or find oppressive, not having your cellular traffic recorded, not having your neighbors blow smoke onto your porch when you're trying to read a book outside on a sunny day.

Wielding this distinction, "freedom" is neither inherently good nor inherently just, and descends into the murky grey that already embroils everything else in our lives; each positive freedom we enforce strips away a negative freedom, and each negative freedom we guarantee eliminates a corresponding positive freedom. This sad state of affairs is often referred to as the Paradox of Positive Libery.

I believe that the balancing of positive and negative freedoms is a fundamental task of managers and management. When we've lucked upon (or perhaps nutured, if you're much more talented than I), a phenomenal culture and a great team who are executing well along a worthy roadmap, then like a central bank reducing interest rates to avoid a bubble or a jogger reducing their pace to lower their heart rate, carefully ramping towards negative freedom and away from positive freeom is one of our essential tools for facilitating and prolonging success.

Further down the road, if the structure loses its luster, the economy shifts around us, or entropy's endless march throws a wrench into the machinery, then once again we shift towards positive freedoms, which gives the organization a greater chance to successfully adapt to its new circumstances.

Using the two together, management slowly deaccelerates to keep the good times rolling, and accelerates to help push through challenging periods.

Freedom is a loaded term, so it's easy to deteriorate into a moral discussion, but in times and topics of great sensitivity, I believe looking through the lens of system dynamics is a valuble approach. Companies are vastly complicated systems with dozens of feedback loops, and–like salary, titles and reporting structure– managing the kind and quality of freedom is simply another mechanism to be adjusted with immense care and consideration, but to be adjusted nonetheless.

A few closing tangents. First, Tom DeMarco's Slack has an excellent suggestion for a good starting state between positive and negative freedoms for engineering teams: generally follow the standard operating procedure (e.g. keep doing what you're already do, how you're doing it), but always change exactly one thing for each new project. Perhap use a new database, a new webserver, a different templating language, use a static JavaScript frontend, whatever: always change exactly one thing.

Second, I'm always terrified of getting on the wrong side of history, so I've spent some time considering how this discussion of freedoms relates to Ben Horowitz's recent post on Can Do vs. Can't Do Cultures. I read that article as describing how young companies focused on innovation differ from mature companies which are trapped in the The Innovator's Dilemma. Older companies can (and do) foster sheltered pockets of innovation, like the example of Larry Page investing into good ideas he encounters within Google, but maintaining a market position is fundamentally distinct from creating new markets and I think the more complete argument is to use both cultures (and in parallel, to emphasis on positive and negative freedoms) in the appropriate circumstances.