The Art of the Long View, Applied to Software – On Strategic Thinking – It’s your job too, now!

You still can’t predict the future. But it’s coming at you faster. Be your everyday strategist.

Books & authors mentioned herein are:

Scenarios for Tomorrow

When I first picked up The Art of the Long View: Planning for the Future in an Uncertain World, written by Peter Schwartz in 1996, I told myself something along

Cool, the tools in there might give me insights into how executives think and might help me become one: if they look useful, I’ll return to them in a dozen years or so when I made my way up.

That was in early 2019, roughly a year before my employer of the day got acquired by a bigger company and I got to actually try these tools out: for planning my own work, but also in trying to understand how the executives in my new hierarchy were (or were not) reasoning¹.

I quickly came to realize that they also apply on a regular basis as soon as you reach a certain level of responsibility. Not only as an engineer, but also as a plain product owner or project manager.

If we accept the premise that things are happening faster, it implies that the time horizon of the tools you use to reason about the future have shrunk, too: what might have been the prerogative of a few corporate strategists thinking about the next five to ten years now becomes your own, as what you do today has strong relevance on what happens on your project in one or two years!

Incidentally, showing that you can think about how things can go wrong in a relevant manner is a good way of working towards a promotion – or just plainly saving yourself some time, if getting up the ladder is not your goal.

Time Compression

One of the tenets of the modern age is that everything seems to be happening faster than before.

There is a feeling of time-compression, of sorts. While it’s not entirely clear to me if this is a form of hindsight bias (I haven’t really lived through the “slower” days of the last century), my parents and grand-parents do indicate that things became more crazy, not less. By the way, observers like James Gleick were already writing about this in 1999².

Having been a teen in the pre-smartphone world, I do also remember that things were somewhat slower before, but again, maybe it’s just that you get to see more of what happens when the internet is yelling at you from your pocket every single minute of the day³.

Whatever you think about the speed at which things happen in the general world, I’m pretty sure that we can agree that in the world of computers and software, things indeed have been accelerating.

The Pre-Mortem Bronze Bullet

My favourite tool from the book is the pre-mortem⁴: it’s conceptually very simple and can quickly unlock fresh perspectives when planning. Plus, you can start using it today, either on your own or with your teammates.

It boils down to asking:

Let’s project ourselves into the future, to the date where we currently imagine delivering this project of ours.

Let us imagine that we failed: what are reasons that could explain that hypothetical failure?

There’s much more to Schwartz’s book than the pre-mortem, but this gets us into summary territory, and you’ll find these on your own.

Though silver bullets supposedly don’t exist, pre-mortems come pretty close to ressembling one: it’s still up to someone to do something about what is uncovered, but I pretty much guarantee they will uncover relevant risks.

Remaining Humble

(Sanely) reasoning about the future requires us to accept and to understand that we are most likely wrong when we try to anticipate it – mainly because predicting the future is impossible.

This belief that the future will unfold as we anticipated it is a major contributor to project failures both big and small: learning to be humble about our own predictive abilities is an excellent step towards becoming better at whatever it is we do. It does not guarantee success, but certainly reduces the consequences of failures.

Thus, if you wish to progress along an engineering carreer – or anything else with increasing responsibilities, really – I can recommend reading The Art of the Long View.

Finally, another reason I’d encourage you to take the long view is that software is eating the world (and yes, doing so faster and faster). Being blind to potential futures and ignorant of hidden and second order effects when building said software likely exposes us all to (very) unpleasant risks.

As an unrelated bonus, here’s a presentation by Nassim Taleb for the Long Now Foundation titled The Future Has Always Been Crazier Than We Thought, which I ran into when googling something for this post.

Hope you’ll enjoy watching the future unfold, whatever speed it happens at today.