How to think strategically in your job

The other day, I saw the question, “How to think strategically?” posed in APAC Marketers – an excellent Slack group I’m in run by my friend, Dave Fallarme.

Members of APAC Marketers typically work at tech companies, so my answer is catered specifically to this type of person. However, I think it will also apply to any junior to mid level employee working in any type of company.

Let’s dig in.

Most strategy advice is not actionable because the concept is amorphous and dynamic

Ask for advice on how to “think more strategically” and you’ll get a hundred different answers.

This isn’t anyone’s fault as there are many levels and definitions of strategy and everyone is answering the question from their own vantage point. Being strategic as a junior marketer in a year-old startup is a totally different ballgame to being strategic as Chairman of a Fortune 500.

To take it a step further, most employees are more concerned with being strategic within the context of their direct team/environment. That is to say, even if you were a junior marketer, and your father is the Chairman and gave you lots of secret insight, you would not be able to successfully leverage that secret high level insight to look strategic to your coworkers. If you tried, you would likely appear to be naval gazing or boasting, likely both.

Incidentally, this is the problem with most strategy books. For example, Good Strategy/Bad Strategy by Richard Rumelt is a great book on what strategic plans look like for the United States military. But it’s so high level that if you, a junior or even senior employee tried to implement it, you will sound completely unbelievable and probably a bit obnoxious.

What then is an actionable way to think strategically in your job?

Think one level up the food chain

Meaning, start thinking about your boss’s concerns.

And once you’ve mastered that, take your boss’s boss’s concerns into consideration.

For example, at a junior level, the only marketing consideration is timelines and how to execute. So a junior that is able to also think about budget concerns and conversions/impressions (aka the next expected level) will appear to be thinking strategically.

The next step up the food chain might be managing long term brand impact. Then one step even higher up the food chain might be that the company is being acquired soon, so short term impact matters more. And so on…

It’s unlikely you can get strategic in the fancy consultant sense of the word until you can master this basic version of strategy.

At some point, you’ll start thinking about the market, company operations and competitors, because that’s the level your CEO/Chairman/Chairman of parent company thinks on.

If you get to this level, you will have the experience to properly apply the Good strategy/Bad strategy book and others like it. You will also have more experience than me, so you wouldn’t need this advice any more!

How to achieve this

The best way to achieve this is to do a combination of sense-making and straight up asking your boss (and boss’s boss) what they care about.

And if your company has levels or some version of OKRs available for you to read, you should. Try to make sense of them deeply. Emphasis on deeply because someone on level 1 is likely to read a level 3 responsibility and understand the words but have no concept of the implications or pressure such an expectation entails.

The most actionable way to seek out this level of understanding is to look for incidences when your boss implements something that appears completely stupid and tone deaf to you. You see, it’s likely that it’s not stupid, it’s just that you don’t actually understand the forces at play. If you aren’t already familiar with the concept of Chesterton’s Fence, it’s worth reading up on.

Taking a step sideways works too

Your team doesn’t work in a bubble. Instead, you typically have lots of projects which overlap with other teams.

Therefore, if you’re a marketer and are able to take product into consideration, people will say you’re strategic. If you’re able to take dev/design into consideration, people will say you’re strategic too.

Obviously, at some point, knowing everything becomes impossible. So when in doubt, start with the steps closest to you and master those first.

To be honest, it’s not hard to start thinking strategically. The real difficulty is making sure you don’t get ahead of yourself.

Here are two common traps people often fall into when they think they’re thinking strategically.

The Dunning-Kruger trap

The Dunning-Kruger effect is a cognitive bias in which people think they’re smarter/more knowledgeable than they actually are.

If you employ this method for thinking strategically in your job, you are making yourself extremely susceptible to Dunning-Kruger-ing yourself.

This is because good strategy often seems very simple on hindsight and to the inexperienced (i.e. you). Likewise, well-written roles and responsibilities.

As a result, it’s very easy to breeze through a reading of your boss’s boss’s boss’s OKRs and think to yourself, “wow! I can now think like a CEO!” When in fact, you sound more like a self-important child at a dinner table stating something obvious while all the adults smile encouragingly and indulgently because it’s too much of a chore to manage your hurt feelings if they burst your bubble.

This can commonly be seen in meetings where that one colleague is talking loudly about market trends, while everyone else in the meeting is rolling their eyes.

How to avoid this trap

  • Take the time to deeply understand, and even after you’ve done so, err on the side of caution and assume you only understand 10-20% of what you think you do.
  • Watch out for social cues. If nobody senior to you is agreeing with you, you’re probably talking out your ass.
  • Ask if you’re understanding the issues/concerns correctly. And obviously, be open-minded and grateful if people say that you don’t. If you ask, then ignore the feedback, rest assured people will simply start giving you platitudes as they recognise you’re not actually looking for feedback.
  • Don’t go too many steps up or across. Rather than trying to think like your CEO, limit yourself to thinking deeply like your boss or at best, your boss’s boss. Rather than trying to think like your DevOps or Infra coworker, limit yourself to the teams you directly overlap with like Frontend dev.

Neglecting the trees for the forest trap

Yes, I’m turning a popular aphorism on its head. This is the employee who spends all their time talking about the bigger picture.

Many an employee has fallen prey to this. Once your mind has been opened to strategic thinking, the day-to-day grind stops interesting you.

This is fine if you already understand trees like the back of your hand. But nothing is more annoying than the employee who neglects their daily responsibilities in favour of “high level stuff”.

It is especially toxic and dangerous if you appear to be decently good at high level stuff. Why? Because you’ll have the veneer of intelligence and strategic thinking without the operational fire power to truly create good strategy.

How to avoid this trap

  • Do the fucking work!
  • If you start to hate your day-to-day work, a great way to constructively deal with this problem is to create a new “job” for yourself to process-ise and automate your daily tasks. Not only will you appear incredibly strategic, it will ensure you know your work well, and give you a different perspective and new motivation for mundane work.
  • Be suspicious if your coworkers (at the same level) start avoiding/disliking you.
  • Constantly check your own believability score. If you’ve gone too many steps up or across, you stop being believable. As a general rule of thumb, more than 2 steps is too far.

“But this isn’t strategy!”

Let’s be real. “Strategy” is a nebulous concept that means vastly different things to everyone.

In contrast, the advice I laid out here will help you appear strategic to your coworkers and boss. And ultimately, that’s all that matters.

At the end of the day, it is my view that the only difference between strategy and tactics is that strategy sits one level higher than tactics. So what appears as tactics to your boss, will appear as strategy to you.

And that’s all strategy is, really.