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15 Signs of A Strategist: Strategic skills for you to embrace

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When it comes to strategy, things aren’t that complicated. I shouldn’t even really have a job. But thanks to a litany of fancy MBA programmes and boring textbooks written by old white American dudes, strategy has become some kind of mystic art. It’s largely dominated by the Big 4, it’s swimming in a sea of complicated jargon and it makes us all the victim of long, expensive and mostly unreadable documents.

It doesn’t need to be like this. You heard it here first, kids: Strategy is simple.

In fact, if you’d like a strategy MBA in 4 minutes, here you go:

 

HubSpot Video

 

Strategy needs a strategist

While strategy might be simple, if we want it to actually happen, then we need people who understand it, and who lead and work in a way that supports its execution. For that reason, the number one leadership training request I get is to teach people "how to be more strategic."

Now, in some ways, this is a misnomer. At heart, everyone is strategic. Our ability to strategise - join the dots, think long term and plan for the future - is the defining characteristic of being a human.

But… some of us embrace that side of our nature more than others.

If you’re wondering whether you might be a strategist, check out this list for the top 15 telltale signs.

15 signs of a strategist

 

You ask annoying questions
You're always thinking about the next step
You see angles everywhere
Your mind never stops
You exhaust people
You're always running simulations
You're insatiably curious
You love change
You know yourself

You love a framework

Nothing's ever finished
You can be disconcertingly decisive
You underestimate your own effort
You're incredibly resilient
You're still reading this article

 

1. You ask annoying questions

When everyone else is keen to accept what’s in front of them and crack on with it, you’re the one holding up the process. You’re probably asking questions like…

  • “Are we sure this is really a problem?”
  • “Do we need to do it like this?”
  • “Is there a better way to tackle this?”

My top three annoying questions, inspired by my three children are:

  1. But why? - Courtesy of my 5-year-old, this one is best when asked 3-5 times. There is no easier way to dig below the surface and find the root causes of our problems than repeatedly asking why something is really happening. If you were hoping for a crash course on systems thinking, this is basically it.
  2. So what? - Courtesy of my 10-year-old, this is best served with a touch of belligerence. Asking ‘so what’ is all about getting real on impacts and consequences. That way, we make sure we don’t waste our effort on minor things. This one can rub people (and mothers) the wrong way, but it’s important- not all problems need to be solved, and lots of things don’t really matter.
  3. Is it, though…? - Courtesy of my 15-year-old, this is best asked with a dubious, authority-questioning inflection. Strategists know that we tend to make decisions that rest on untested assumptions, and that if we don’t check whether things are true now and again, we get into trouble.

Pro tip: To keep your friends and colleagues on side, learn when people just want you to listen, and to distinguish when urgency matters more than accuracy. In those times, your questions can be unhelpful.

2. You're always thinking about the next step

Before you’ve even reached the goal you’ve spent months striving for, you’ve moved the goalposts.

The weekend before your half marathon, you’ve booked into a full and you’ve googled “World’s most scenic 100 milers.” You hardly notice you’ve run the half.

Pro tip: Start to meditate. Presence makes things more enjoyable. Honestly.

3. You see angles everywhere

Everything becomes part of a potential narrative for you. If you’re in business, you’re thinking about the USP or commercial spin to outdo your competitors with.

If you’re a writer, you’re always thinking of new headlines or story arcs. Sometimes, you only need one or two facts to string together something exciting and compelling.

Pro tip: Try not to shut yourself off to non-conforming ideas too early. Once you’re locked into your own spin, you’re vulnerable to blind spots.

4. Your mind never stops

t just goes and goes. People often ask if you ever ‘switch off.’ And then when you do try to chill out, the extra headspace seems to unleash little havoc bubbles of new creativity you didn’t see coming.

You’ll try to read or relax, but you keep having little ‘aha!’s that get in the way.

Pro tip: Run. It’s tiring. If that doesn’t work, write everything down.

5. You exhaust people

Not everyone has, or wants, a master plan. When you see the potential in everything, this can be very frustrating for your friends and family who just want to be happy with their achievable goals.

Pro tip: Learn to accept where people are at on their journey, and be ready when they are.

6. You're always running simulations

Budgets. Plans. Ideas. The scribbles are many. The ideas are plentiful.

It’s not enough for you to wonder ‘what if’, either. You immediately go looking for how it would work, and what the steps would be to get there. This is a great advantage, because you can turn dreams into reality. But the danger, of course, is missing the value of what’s right in front of you, and failing to appreciate what you already have.

Pro tip: Cultivate a gratitude practice. Journal each day.

7. You're insatiably curious

You respond to new ideas with enthusiasm, often citing something you’ve read, or listened to recently. (‘Oh yes! I just heard a podcast about that…’)

This curiosity and boundless appetite for knowledge is beautiful, but it does risk eye rolls from people who’d prefer small talk (or you becoming the human Google of your family or friend group.)

Pro tip: Know when to put your things away.

…or, just don’t talk to boring people. That’s my preference.

8. You love change

It could even be said you’re a change junkie. When the shit hits the fan and other people look panicked, you’re trying to keep the glee off your face for the sake of politeness. Change means challenge and innovation to you, which are two of your favourite things.

In fact, if you don’t have some change land in your lap regularly enough, you go out and create some.

Warning: this kind of preference can be needlessly disruptive to you, and the people in your life. It’s also a fast path to stress addiction, which, y’know, will slowly kill you. As my favourite strategy author and buddy Max McKeown famously said: “Change is inevitable. Progress is not.”

Pro tip: Make sure you’ve closed out your last batch of stress before you kick off another. Try not to f**k with things for the sake of it.

9. You know yourself

Strategists have a strong sense of who they are, and what they’re about.

You’ve got a clear vision, strong values and you know what you’re willing to tolerate… and what you’re not. You play a long game, and you’ve got rock solid boundaries to make that happen.

Of course, this can also make you insufferable, not much fun at parties, and more inflexible than you’d like.

Pro tip: Be open to emerging versions of your vision, and yourself.

10. You love a framework

This leads on from the simulation one, and for the most part, it’s great.

Because you know that every impossible-looking goal is just a series of steps you can follow (writing-a-book steps, running-a-marathon steps, starting-a-business steps), you’re a sucker for new approaches and theories.

5AM club? Sign you up! Cold showers? Totally! Lean? Agile? Servant leadership? Sure thing, you’ll have a crack!

This kind of experimentation is cool, until you become a fickle human guinea pig. For your family and team, it can be a pain in the ass to accommodate your latest thing… only for it to go in the bin a few weeks later.

Pro tip: Learn to sample principles and small steps at a time, instead of throwing yourself into a new system every three months.


11. Nothing’s ever finished

And why should it be? You get your best go, and then you get your next go!

You’re always optimising, tweaking your website, changing your setup and researching new tools. There’s always a smarter, faster, more innovative way to tackle something - and you love working out what those are. Which is cool… until you start wasting time that could be better spent elsewhere.

Pro tip: Learn when something is good enough and no longer deserves your energy. You’ve got bigger fish to fry.

12. You can be disconcertingly decisive

… especially for big decisions.

While you might dilly-dally on generating ideas or working out the right way to get somewhere, once you’ve made up your mind, that’s that.

Big decisions like which house to buy, which job to take, or which person to marry happen quickly.

(Or, hypothetically speaking, you might spend 3 months with half a dozen internet tabs open researching a new clothes dryer or standing desk, and be able to quote specifications people have never heard of, but you’ll launch a new programme after a 3-minute conversation and have registrations up on the same day. Hypothetically.)

Pro tip: Have a trusted truth-teller close by who can let you know if you’re being more impulsive than you realise.

13. You underestimate your own effort

You’re so accustomed to planning, researching and strategising your way through life, that it’s second nature now.

When people ask you how you achieved something, you’ll brush it off, or exclaim “oh, it’s easy! Anyone can do it!”

Which is partly true. But it also isn’t, because not everyone thinks like you do. And it wasn’t actually easy, you’ve just forgotten how hard it was now that you’ve reached the end and you’re eyeing up the next challenge. So, don’t be a dick about it.

Pro tip: Take the time to celebrate your achievements, and acknowledge how hard you worked for them. 

14. You're incredibly resilient

Strategists think a lot about risk, which means they prepare for and expect the worst. They know failure is part of the game they play, so instead of betting on things going well, they back themselves.

Over time, that bet pays off, and you learn that there’s pretty much nothing you can’t handle or work your way out of.

The obvious danger here is that you can get a bit cocky and fail on a much grander scale than you expected…. but that’s actually OK. The more insidious danger of your self-reliance is failing to depend enough on others. Anything that’s worth having is a collective effort, and anything world-changing needs other people to be on the journey with you.

Pro tip: Work on your collaboration skills. Impact needs scale.

15. You're still reading this article

Yeah look, I know it’s a bit twee, but honestly - if you’re on a strategy website, and you’ve just read 14 points in an article about whether you’re a strategist…

You’re probably a strategist.

So, own it. As far as I’m concerned, strategists are the heart of progress. Yeah, it’s a bit exhausting at times - for you, and the people around you - but it’s thanks to people like you that things keep getting poked, prodded and fixed. Who wants to live in a world where the status quo is untested and nothing new happens?

Not me. But then, what would I know? I’m a strategist too.