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How to be a Strategic Thinker

Everyone has heard their boss tell someone - “you need to think more strategically”.

It’s one of those bits of corporate speak that people tend to throw around in meetings and everyone else nods approvingly, indicating that *of course* they all understand it. Secretly, afterward, we pull out our smartphones and try to get definitions for it.

Just in case anyone asks.

Being told to think ‘strategically’ is a rite of passage in Corporate America, or life really. It’s right up there with ‘you need to get out there more’ and ‘you need to figure out what you want’. All helpful (but cliché) advice.

And yet…maybe there’s something to this ‘strategic thinking’.

Can we define strategic thinking?

Let’s break it down. The word strategy comes from the military context, where we seek high ground (literally) to be able to see the battlefield and then make an attack plan against the other army. So, applied to our present-day work lives, a strategic marketing plan could very simply be ‘how to capture more market share in X demographic by promoting Y product with new offers and discounts.’

So then, in order to think strategically, we must first get a (literal or figurative) better view of the situation - see the big picture, if you will - and having seen the forest as well as the trees, being able to see enough detail to avoid error and yet never losing focus of the ‘prize’, we can venture forth and get that ‘win’.

Just seeing the big picture, though, isn’t enough. It’s almost like strategy is about planning not one, but a collection of options, each of which plans for the possible perils our army may face in the battlefield. For the enemy troops aren’t the only challenge - we could face rain or snow, run out of food, experience unexpected casualties or worse. And YET, the battle must be won.

Thus, we need a responsiveness to challenges that is unique and quick, because the best laid plans have a way of going awry. So no strategic plan can be complete without thinking about pitfalls, human error, external factors, or a change in budget from up top.

Think about it

Indeed, we now can say we better understand ‘strategy’. Have we spoken enough about ‘thinking’, though? It seems such a mundane, normal activity that it scarcely bears mentioning. And yet, most people are terrible thinkers, as evidenced by the continuity of human problems.

Being a good thinker is being someone that is good at consciously ordering one’s thoughts. Giving the amorphous cloud of feelings, fears and panic a place to be let out, like bad air being let out of the house through a window. Treating each one simply as an unanswered question, that, the moment it is answered, ceases to exist altogether. Which is why we spend so much time developing instruction manuals and FAQ pages as well as walking our team through each detail of the plan.

Some tips to think better - think out loud, if it sounds good, that’s a good way to test both the content and wording. Write it down - this helps us give it more structure, remember it and also cut out whatever’s not needed. Say it to another person - the audience is a good litmus test, does it all make sense? Is anything missing? As we go through this process more and more, we can get better at anticipating pitfalls, and need less feedback to get to the final form (yet always asking for SOME feedback, just in case).

Final Thoughts

The best planners, strategists and thinkers work best when there’s an audience, advisors, teammates and others involved. There has to be someone to vet the plan, offer feedback, carry out the plan, fix unexpected problems and so on. The point is, with your newfound privileges and responsibilities of being a ‘strategic’ leader, lets not forget that the best manuscript isn’t a book, and the best plan is nothing if not put into action. So ultimately, the most strategic thing a person can do is be great at their work and personal relationships, for, with the right people around you, there isn’t a battle you can’t win.


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