Is there such thing as a strategic personality?

My party trick is to guess people’s star signs.

This is a bit weird, not just because it’s odd on the face of it, but moreover because I don’t really know anything about astrology, and nor do I put much stock into horoscopes.  As a matter of fact, I couldn’t even tell you which birthdays correspond to which sign.  August the 24th?  No idea.  December the 2nd?  Clueless.  March the 30th?  Why that’s Aries of course – but then that is my own birthday, so that doesn’t say much.

Still, in spite of this, I’ve found I can guess people’s signs with an accuracy level far beyond that of random chance (roughly 1 in 2, rather than the random 1 in 12).  There’s nothing magic about it I’m sorry to say.  And I can’t do it for people who I don’t know, like a random stranger on the street.  It’s simply the case that I know the vague gist of the astrological “personality types”, and then am able to match them to the individual in front of me.

I know, I know, for most of you that is no explanation at all, considering star signs mean “nothing”.  But in my experience that isn’t the case.  I’ve found there are indeed imperfect tendencies that do correspond to reality, hence my 50% success rate.  You don’t have to put this down to anything woo-woo if you don’t want to.  Who knows, it could be something to do with the weather in the first 6 months of your life, your relative age in your school year, social conditioning from the astrological-industrial-complex, whatever, it doesn’t really matter.  All that matters is there is some deep and indecipherable current buried in the chaos of reality, which we are able to glimpse momentarily, and then rationalise into a framework such as star signs.

That’s my theory anyway.

The reason I bring this up is not to convince you of the validity of astrology, but rather to consider the other side of this anecdote: “personality types”, and their implications for strategic thinking.

Now I should flag immediately that I am no expert in this field whatsoever.  I am no more a clinical psychologist than I am a clinical astrologer.  But I do know a fair bit about strategy, and I have noticed what I think are some meaningful patterns between these fields which – taken with a pinch of salt – I think are interesting to consider here.

Let’s first touch on how one determines a personality type.

From what I’ve gathered, the most robust and substantiated measure of such traits is the so-called “Big 5”: openness, conscientiousness, extraversion, agreeableness, and neuroticism.  Measuring people on these categories supposedly yields a high degree of predictive power in fields such as career success, political opinions, and so on.  However, much better known to the layman is the Myers-Briggs – a test widely used in the business world which organises people into the 16 personality types defined by letters such as “ENTJ”, or “ISFP”.

Now it’s ironic I started this essay with astrology, because for many psychologists the Myers-Briggs is little better than that.  It has regularly been “debunked” for various reasons including its inability to predict life outcomes, its overly simplistic “binary” nature, and the fact that people may get different results each time they take the test.

Still, in spite of this, just as with star signs expert criticism has failed to dampen its popularity amongst the general public.  The fact remains that despite its perhaps limited clinical viability, it has nevertheless proved a fun and simple way for people to approximate their personalities.  If you’ve ever done it, you’ve no doubt experienced the “that’s so me!” effect it tends to provoke in its descriptions.

What interests me here however is not the test as a whole, but rather one specific metric within it: “S” vs. “N”.

Basically each one of the letters in a Myers-Briggs type represents a spectrum.  For example all types begin with either “E” (extroverted), or “I” (introverted), as determined by where people fall on that particular line.  The binary division implied by the two letters is one of the main criticisms of the test, but you can see why the average Joe likes simplicity and certainty it implies.

The second letter is the one we are interested in, which is the spectrum between “sensing” (S) and “intuiting” (N).

In essence what this determines (and I’m somewhat butchering it for our purposes) is whether one likes dealing in “facts” or “theories”.  Whether one sees things “as they are”, or sees things in terms of patterns and abstractions.  Whether you like the detail, or like the gist.  Whether you like to “zoom in”, or “zoom out”.  The former are all “sensing”, and the latter “intuiting”.

If we were being hyper-reductive about it, we might imagine a strongly “sensing” person to be a scientist or an accountant: someone who is rigorous, detailed, and fact oriented.  And we might imagine a strongly “intuiting” person to be a philosopher or psychotherapist: someone who deals in meaning, concepts, and the information “between the facts”.

I mentioned in a prior essay the ideal founder partnership as represented by Steve Wozniak and Steve Jobs at Apple, and we might say this is an example of a partnership between these two abilities: the scientist and the philosopher together to create a powerful holistic unit.

Now I’ve got to inset the obligatory caveats here: 1) everybody is a blend of these things, not either / or, 2) everybody is capable of both kinds of thinking, and 3) a hell of a lot more goes into strategic thinking than a narrow metric lifted from a maligned personality test.  I am confident that many great strategists would be labelled as “S” if they took the Myers-Briggs.  But even so, it has been my experience that this characteristic does, broadly speaking, map neatly onto strategic endeavours – where we might call someone who is strongly intuiting a “naturally” strategic kind of thinker, and a person who is strongly sensing less so.

Why?  Firstly because developing strategy requires certain ways of thinking which come more easily to the intuiting:

  • It requires a zoomed out perspective which isn’t readily compatible with a passion for detail
  • It explicitly involves the spotting of patterns and potential in seemingly unrelated data
  • It requires broad-brush simplification to package and communicate

Secondly – perhaps more importantly – it also requires a tolerance for certain “pathologies” which a strongly sensing individual may not have, and may wish to avoid, for instance:

  • A willingness to overlook specifics in favour of a rough sketch of a situation
  • Comfort with generalisation
  • Acting off the back of theory rather than hard empirical proof (which of course one can never have for a strategy, which is by definition speculative)

Consider my little astrology riff at the start of this essay.  To a certain kind of mind (perhaps even yours…) it would be completely infuriating.  It’s sweeping, unreliable, non-replicable, and totally lacking “proof” beyond my anecdotal experience.  On a sensing level it’s a car crash.  But on an intuiting level, sniffing for patterns and connecting the dots, it’s intriguing.  It may be nothing, it may be something – but either way it’s fun to explore.

Based on that, it will not surprise you to know that according to these tests I sit at the very far reaches of the spectrum for “intuiting”.  For whatever reason it’s just how I happen to approach things.  I say this in no way as a brag, because it’s not necessarily good– in fact it is arguably debilitating in various ways.  However it is at least useful for my line of work.  My whole career, ultimately, is little more than an exercise in monetising this one peculiarity of mine; present by chance in an otherwise unremarkable bloke.

As for you, well, I expect that if you sat way out at the opposite end of the spectrum (the sensing end) you would have unsubscribed in disgust long ago.  You would also probably be a very poor strategist – but that’s no big deal as you’d be a very fine something else.

No, I expect that you, my reader, are probably somewhere along the intuiting road with me; or at least sympathetic to that way of thinking.

Either way though, I’ve found that simply being aware of this dichotomy can be quite useful.

For one thing, it allows you to appreciate the important idea that there is a continuum of thinking styles ranging from the computer-like ruthlessly factual, right through to the fully “woo-woo” esoteric, and that they all have their place.  They all have an crucial role to play, and blending them together (Wozniak-Jobs style) should always be our goal – just as we should always avoid the trap of seeing one as “right” and the other as “wrong”.

For another thing, although I would hesitate to label anyone in too reductive a manner, it also allows us to adjust our communication to our audience.  For example, if you are a trying to sell a strategy to someone, the likelihood is that you’ll be selling to a “senser” – someone who wants to know what it really looks like on the ground, and to understand the hard facts behind it.  They won’t be swayed by its elegance, it’s instinctive merits.  This means you have to pull the strategic thinking away from the abstract world where it may have originated, and into the world of hard reality.  Of evidence, feasibility, and action.  This won’t only make it more buyable, it will make it straight up better, since a strategy that doesn’t survive contact with the realm of the sensing will be little more than the hot air they suspected it to be.

(Sensers I’d suggest make up for their poor ability in generating strategies with an excellent ability in judging them – they’ll smell bullshit a mile off, and won’t be afraid to say so).

In conclusion, wherever you land on the spectrum, the ultimate message is this:

  • Lean into the intuitive, the theoretical, the abstract, the woo-woo and unsubstantiated to develop strategy
  • But drag it back to the world of the sensing, the factual, the rigorous and disciplined to judge it, and to make it happen

Your “personality type” may well make one or the other of these the easier part of the equation.  But ultimately you’ll have to have both.

Good job we all contain multitudes, and cannot be defined by a celestial symbol, or simplistic collection of letters.  Well, not completely anyway.

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