I’ve finally figured out why most strategies are so bad

This idea comes from a Linkedin post I did which seemed to strike a nerve, so I thought I’d expand on it here.

What are the ingredients of a great strategy?

  • Data?
  • Insight?
  • Creativity?
  • Skill?
  • Leadership?
  • Knowledge?
  • Clarity?

For sure, all that stuff is required.  But there’s one other thing which is just as crucial – perhaps even more crucial – that I’ve never heard anyone talk about.

That thing?


Pain is a fundamental piece of the strategic puzzle, and without it, no true insights or creative leaps are achieved.

Let me explain why.

To develop an effective strategy, the first thing we need is an accurate reading of our situation.  Of our market, of ourselves, of the world we inhabit.  We need a grasp of what’s really going on, so we can then navigate it effectively.

Strategy is simply when we align our actions with reality in a harmonious way.  So the better we understand reality, the better our strategy will be.


But here’s the issue.

Being human, we all inhabit something of a fantasy world.  A world which is half truth, and half fiction.  We see some things as they are, but with others we are totally deluded.

Why?  Self preservation.

We interpret the world in a way that comforts ourselves and our egos.  We believe we have strengths that we don’t.  We believe others have weaknesses that they don’t.  We believe the world conforms to our theories, our beliefs, our biases.

We believe, in short, in a world that isn’t fully true.

This then makes good strategy not only hard, but sometimes impossible – because we create strategies that are designed not for the world as it is, but the world as we wish it was.  The world as seen through our own personal lens.

Such strategies of course can never be effective.

Now here’s where the pain comes in.

This dilemma I’ve described above can only be solved by one thing:

Unflinching critical examination.

Of ourselves.
Of our business.
Of our competitors.
Of our market.
Of everything.

…until we unearth the lies we’ve been living by.  The barriers that stand between us and a clean reading of the situation.

This of course is unpleasant.  It hurts.  And the pain is unavoidable, since it’s inevitable that our delusions will be self-serving.

(After all, we’re only really going to delude ourself when our ego is on the line, right?)

All of this then explains why most strategy is so impotent:

Because to do it well, is to undertake a painful exercise in ego-death.

And who wants that?

What we want instead is to validate our beliefs.  And frankly, that’s what you see when you look at most strategies.  An exercise in self-validation.  A statement whose sole purpose, despite appearances, is to make the author feel good.

So if we’re willing to take the pain, how do we do it?

To reveal our delusions, I think there are basically two approaches:

  1. Let the market tell you.
  2. Let an external advisor tell you.

The first one is what I did, primarily by starting to post on Linkedin all the time.  Believe me, this was a humiliating exercise – in the most literal sense, in that it made me humble.  It made me realise that what the market wanted and needed was not necessarily what I thought.  And so I had to undergo a painful (continuing) metamorphosis to match my beliefs with those of the wider world.

You can do the same thing via the feedback loops that exist in your market, whatever it is.  It doesn’t need to be social media.  The important thing is that you listen for the challenges to your worldview that lie within the data, rather than doing what we’d all rather do – ignore them.

The second approach is easier, and therefore more expensive – hiring someone to call you out.

This is basically why consultants exist.  Not necessarily because they are smart, or experienced, but because the don’t care.  They’ve got no dog in the fight, so they’ll be able to unpick your reality better than you will.

(Of course I would say this, but I think this is one self-serving opinion which is probably true).

The crucial bit with both techniques ultimately is this:

  • Did it hurt?

Where were you humiliated? Bruised? Contradicted?

If the answer is “nowhere” then my advice is listen deeper.  Because that feeling, that pain, is the feeling of a breakthrough unfolding.  No different from being in the gym, or on the therapy couch – you want the results, you’re gonna have to go through it.

I believe in this so strongly I’m tempted to add a section to my strategies called “the pain”, just so we can be sure we aren’t slipping into something comforting but meaningless.

And to that end, I’d ask you the same question:

What was the pain behind your strategy?

If you can’t find it, you know what to do.

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