July 2019
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If truly the goal of your organization is about profit you are most probably dealing drugs or selling insurance. But if you are not in either of these businesses, what is a true strategic vision your organization has (or should have)? And, even more importantly, what is the optimal way to have it achieved?

Aga Szóstek

Jul 12 · 11 min read

The fastest way from Earth to Mercury would be a straight intercept of about 50 million miles, which might sound a lot but is not that far in terms of space distances. So, if you wanted to shoot a rocket towards Mercury you should shoot it directly. Only you wouldn’t. Doing that would require a tremendous amount of fuel to apply the brakes and the sun’s gravitational force would make it impossible for a spacecraft to slow down enough to go into Mercury’s orbit. Yet, there is a nifty way to do so.

When back in 2004 NASA has sent MESSENGER towards Mercury they used “gravity assist,”: using the gravity of a nearby planet to hitch a ride. Before MESSENGER managed to orbit the most inner planet of our solar system back in 2011, it has used three planets for six gravity assists: it passed close by Earth (August 2005), swung by Venus twice (October 2006 and June 2007), and raced past Mercury three times (January 2008, October 2008, and September 2009). On each of those occasions, the gravity of a planet was used to temper the spacecraft’s speed and redirect it on its circuitous and energy-efficient journey towards a graceful approach for insertion into Mercury orbit. All in all, by March 17th, 2011, MESSENGER have logged 7.9 billion kilometers, circling the Sun 15.2 times! The way the mission was achieved is a great exemplar of an oblique approach.

MESSENGER’s orbital trajectory from Earth to Mercury. Image Credit: NASA/Johns Hopkins University Applied Physics Laboratory/Carnegie Institution of Washington.

Direct versus oblique

A direct approach is the one when you set a goal (like earning a shit load of money) and you set your course to do just that. How successful do you think you are going to be? It is like taking Prozac to feel happy. Why? Because, a direct approach demands from you to know the method in which you reach the solution even before you start (think of the numerous failures of the IT projects done using waterfall approach). Probably the most well known examples of applying direct approach are modernism in architecture and communism in governance. As a person growing up in communist Poland I still remember how regulation of pretty much anything: from work, to food, to travel, to education was a seriously bad idea for successful living.

But perhaps even a better story to illustrate the drawbacks of a direct approach is the story of designing and building the capital of Brazil: Brasilia. It has followed the philosophy of modernism as defined by Le Cobusier that: — “Houses are machines for living.” The entire city was envisioned by one Brazilian architect Lúcio Costa and designed by another one: Oscar Niemeyer.

Lucio Costa shaped the plan of the central city as a bird or an airplane. Its form is emphasized by two highways: one, which runs from the north to the southwest and links Brasília’s residential neighbourhoods, and the other, which runs northwest-southeast and is lined by federal and civic buildings. At the northwestern end of the first highway you can find federal district and municipal buildings, while at the southeastern end, near the middle shore of the artificial Lake Paranoá, stand the executive, judicial, and legislative buildings. In the central city area stand low-cost and luxury houses. The residential zones of the inner city are arranged into superblocks, groups of apartment buildings along with a prescribed number and type of schools, retail stores, and open spaces.

Brasília was built in 41 months and officially inaugurated on April 21, 1960. Surely, the idea of its structure was idealistically utopian, which although possibly perfect in its lines feels pretty dehumanized.

At the very same time the satellite towns grew like mushrooms after the rain: not planned as permanent settlements and thus offering stark contrasts to the symmetry and spacing of Brasília but preferred by the city inhabitants. It’s there where you can find life and spirit very different to that of the elegant set-piece architecture and rational street plans of central Brasilia itself. It is because, unlike Costa’s and Niemeyer’s direct approach, the shape of these towns was shaped in an oblique manner. It has exemplified the famous words of Jane Jacobs: — “ Richness of the city life is a product of obliquity not design […] Only an unimaginative man would think he could (design it). Only an arrogant man would like to.”

Why is direct approach so counter-intuitively inefficient? Simply because we live in a complex world. And if you want to model a complex system, your model must be as complex at the system itself. Yet, if you look at so many organizations around this is what they do: they try to achieve their goals in a direct manner.

So, what is an oblique approach? It means finding an indirect path to achieve your goals. Think again of achieving happiness — trying to do it directly is probably the best recipe to be unhappy. But if you find indirect ways to do so, chances are you will be happier than you ever imagined. Because the trick is this: complex goals are best achieved when you are not trying to achieve them. So, in other words, if you choose an oblique strategy (like for example building a unique experience for your customers) you might be on the best way to gain success, wealth and fame. Think of climbing mountains, translation of fiction or surgery — neither of these done well is done directly.

Let’s consider the story of Apple. As long as it was concentrated on their vision “Think different”, the company was on its way to become the richest company in the world. As soon as it focused on delivering the best revenue for shareholders, it went down on its face. A similar story happened at Boeing. And if you think of the great companies of your time: are they focused on growth or shareholder value? Or on something quite different? This phenomenon is called: profit seeking paradox.

Thinking obliquely

The toughest truth for many organizations is to understand three aspects that are at the core of thinking in an oblique way. Firstly, if you deal with complex matters there are no “best practices”, which can be repeated and which will lead your organization to a guaranteed success. There was research done on successful and failed startups. You might be shocked to read that both kinds took pretty much the same steps, applied similar market strategies and leadership rules. their success or failure was not the result of some secret recipe. It was the probability: in the market where a number of companies get started, some of them are due to succeed. Our, very human, problem is that we try to simplify the stories of success to look for patterns, which once replicated, will increase our own chances for thriving. But the thing is this: your approach needs to be unique to you and you only. If anything, this gives you a fighting chance to go on and flourish. Because it gives you a chance to be different.

Secondly, as we tend to analyze these generally known success stories, we assume the path to success was first planned and then deliberately executed. That it was achieved directly. In this thinking we hugely underestimate the level of randomness and improvisation that usually takes place. Think of your own organization: how many things are really planned and executed? And how much of what’s going on is pretty random? It is unwise to assume that other companies have a magic pill of self-organization and structured execution of plans. Our world is inherently uncertain and there are as many known knows as unknown unknows.

Then, there is a myth of rationality that we need to face. Lots of our assumptions are based on the fact that we see people (leaders, managers, employees, customers) as homines economiciagents who are consistently rational, narrowly self-interested, and who pursue their subjectively-defined ends in an optimal manner. If you think just that, it is easy to assume a direct approach to making as much money as possible in the easiest possible manner. Yet, most of us is not straightforwardly focused on becoming a billionaire over night. Sure, we hope to have sufficient income to live dignified life but beyond that there is plenty of other stuff that motivates us so much more than money.

Dan Ariely in this amazing book “The upside of irrationality” shows how much we underestimate how important it is for our actions to have meaning going beyond the monetary value. We all want to passionate about stuff and proud of our actions. Think once more of climbing mountains — this is mostly not much fun. Yet people do it. And then do it again. Why? Because they are motivated by things as achievement, pursuing a difficult goal, crossing their limits. Not being: “consistently rational, narrowly self-interested, and pursuing their subjectively-defined ends in an optimal manner”.

The same thing happens at work. Employees want to have a goal, something that motivates them. And let’s be honest, making other people even richer, is a lousy motivation. There are numerous studies showing that people work much better if they are involved in a pursuit of a great endeavor. Something bigger than them. Probably even bigger than the company itself. Something oblique rather than direct.

Finally, we often overestimate our ability to imagine and predict the future. In yet another great book: “Super-forcasting: the art and science of prediction”, Philip Tetlock shows how difficult it is even for those of us who are super skilled (and trained) in forecasting to see beyond the 6-month horizon. Yet, so many organizations optimistically plays with trends to see how the market will be shaped in the coming years. We seem to forget that the best way to learn is to do so by trying things out. By experimenting in the presence rather than designing for the future. By staying under rather than over-confident. Over-confidence is likely to lead us to forget to think critically and to test reality. And once that happens, we are likely to oversee what’s going on around us and miss the signs of the winds changing.

How be become oblique?

One thing that is crucial to consider is that there is a whole lot about our world (including competition and customer behavior) that we simply can’t know. Whatever business we are in that involves interactions with people is inherently complex and too big of a simplification of it might be grossly misleading. So, there is simply no way to figure out what the “right” way for any particular approach is. The only way to untangle our objectives in to keep on learning about them through the process of working through what they really are. In that way over time we are able to gain more generalize-able knowledge that helps us take better decisions. Because, let’s be honest: when you formulate your new kick-ass strategy, what do you know hoe to bring it to life? Not much, right? So, oblique strategies allow for interpretation of what’s going on that can change over time.

There is another thing that is worthwhile considering — when you choose to apply an oblique approach to reaching your strategy, you better focus on the progress (Dave Snowden calls it: a vector of change) rather than the outcome (like it typically happens in the direct approach). It is super important because as we muddle through the uncharted territory of the future market, we are not going to be quite able to understand the processes that are happening along the way. So, what we need is an evolutionary model for our strategy — one that adapts to the social and economic changes, allows for repetition or replication and can be modified through incremental change. President F.D. Roosevelt captured it well by saying: — “If high-level objectives are to be achieved, goals and actions need to be constantly revised.”

The good news is this: as humans we are intrinsically trained to apply oblique strategies on a daily basis. Think of buying a pair of new shoes or even choosing the ice-cream. We take decisions iteratively and adaptively all the time. So the challenge is to forget the notion of homo economicus and start seeing us as employees and customers as truly predictably irrational.

Why is obliquity your friend?

No matter how much you might hope for it people are not going to love your brand for the pragmatic stuff. They will love you for whatever insightful craziness you are willing to add to it. Because we, all people of this world, are, indeed, predictably irrational: we think we are motivated by financial value (and sure, it motivates many of us to an extent) but in fact we illogically love to see some purpose in our show ever mundane actions: either for ourselves or for the world. We want to keep on feeding our Experiencing Self and our Remembering Self with a narrative that makes us feel good about ourselves. Why? Because it gives us a feeling of an award. Something to look forward to as a positive side effect of whatever task we set to do.

Which is bad as well as good news. Bad news means that you need to focus your efforts outside of your core competence, which typically de;livers the pragmatic value to your customers. The good news is though that as you start experimenting with the peripheries it is not likely to affect your core business that much. So, you need to have those who keep the core running and those who make the crazy, delightful, idealistic stuff around it. This is where the experience design comes to picture — here’s the space to inspire your customers in an oblique manner. How? Let me share a story of my friend.

Some years back, he was invited by one of the American banks operating in the south of the States to redesign a drive-thru experience for them. They started with user research, understanding the context of driving through a bank (from the positioning of the screen on the ATM so it fit low as well as high cars or the need for a personal contact with a teller) and based on that data they designed a machine. Not very exciting, heh?

Concept visualization, credits to Alexander Grots

But then, they did what they could to convince the bank to do the following: to turn the external walls of the bank branches into the mirrors. Why? Because as they did research, they noticed that many of the cars driven around were pimped-up: they’ve got great shining spoilers, different colors and more. And they realized that each of the drivers of those cars would simply love to see herself in their creation.

Concept visualization, credits to Alexander Grots

The bank agreed to experiment with this idea in two branches. In the following two months they had more new accounts opened per branch than ever before in their history. And what could have been observed: people were driving around the branch once. And then the second time. And then the third. and more. This is reaching your goal (as many newly opened accounts as possible) obliquely through delivering a unique experience to your customers.


Aga Szóstek, PhD is an experience designer with over 18 years of practice in both academic and business world. She is a creator of a tool supporting designers in ideation process: Seed Cards and the co-host in the Catching The Next Wave podcast.

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