Do you have to be an a*hole to be good at strategy?

This is quite a strange question.

It’s strange because very few people are asking it. Nobody really assumes that you need to be an asshole to do strategy, so why would I even bring it up? It sounds like asking if you need to be Spanish to drive a train, or short to peel an orange. Kinda a non-sequitur.

But, in truth, it shouldn’t be – for the connections between assholedom and strategy are closer than you think.

Before explaining why that is, I first want to address why people don’t think this is the case. People don’t think “strategists are assholes” because the image they have in their heads of a “strategist” is:

  • Someone bookish
  • Someone cerebral
  • Someone who supports others with pertinent details
  • Someone who diplomatically navigates different parties’ views
  • Someone who is somewhat professional and “qualified”

Basically what people tend to picture is not a strategist, but a researcher. An “insights person”. This is especially true in the world of advertising, where that particular sub-species of strategist is indeed quite common.

It’s also understandable because this activity is a crucial element of the strategic process – but it is not the final responsibility in itself, for that responsibility is decision making. Saying “we’re going to do X, not Y”, and making sure people adhere to it.

That is the strategist’s job – and this is where the toxic personality traits might come in handy.

The easiest way to illustrate this is to point to the two most celebrated business strategists in history – Steve Jobs and Elon Musk. Both controversial characters, and both extremely difficult to work for. Are we meant to think this is a coincidence? Or is there a pattern here?

(And no doubt they are only scratching the surface – there are many other less famous examples).

In my opinion there is a pattern, and we’d be foolish to ignore it. The questions we have to ask are:

  1. What advantages might assholes have at strategy?
  2. Are we able to separate those advantages from the more unpleasant elements?

With that in mind, here are what I see as some of the advantages:

Knowing your mind

You cannot create and implement bold strategy if you’re going to be wavering all the time. If you’re going to be blown in different directions by the wind. You’ve got to come to a point of view, and stick to it – not in the face of all contrary evidence of course, but it should be pretty hard to knock you off course.

This therefore requires a certain – shall we say – pigheadedness. And the constitution not to be overly swayed by other people, which, let’s face it, is often going to present as pure unreasonableness.

Being able to give orders

You’ve probably heard me say before that the essence of strategy is telling people what to do. It’s pretty hard to avoid that. So, you’ve got to be comfortable doing it.

The democratic organisation is not the strategic organisation. Nor is the one governed by committee. This is why it’s much easier for owner-operated businesses to be strategic than public companies – because the buck really stops with one person, who can do whatever the hell they want with their creation.

The willingness to purge

Clearly once you’ve arrived at a strategy, you’re going to need to do a lot of purging. Purging of “off strategy” products, projects, and yes, people.

We all know the story of Steve Jobs coming back to Apple and killing almost all their projects, with the attendant carnage that brought. Very few people would ever do something like that – I doubt I would – but such brutal unsentimentally is the essence of strategic focus.


See what I mean?

There are some kinds of blunt personality that would find this stuff easier, and so it’s not unreasonable to ask if they have some form of advantage overall.

In the final analysis however I’d have to say this:

They don’t.

Because you see although certain elements of the asshole persona are useful, there is one that isn’t – namely arrogance. Arrogance and the belief that you have all the answers.

With arrogance, you will never access the power of the open mind; you will never live in the spirit of humble enquiry that this game requires. You see the truth is that although in some respects Jobs and Musk may be “assholes”, they are also something else: curious. Relentlessly so.

To be humbly curious, but also autocratic is an exceptionally rare pairing, but it is possible – and I think that’s what made them so powerful. Normally you get one of these characteristics, but not the other.

So in the end I think it’s easier to start at a place of curiosity, and then learn the brutal leadership skills, rather than to start as an asshole, and then try to shed your arrogance. Indeed, perhaps the latter is near impossible.

So no, assholes aren’t better at strategy. But we could do with channeling them, maybe just a little bit…

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