A pep talk
We all know that being able to think strategically is a good thing for our careers. It’s a skill frequently mentioned in job ads and performance plans. And its desirability will only increase as more of our time-consuming, transactional work gets automated.
But what if you don’t see yourself as a particularly strategic person? Maybe you’re frequently told to ‘get out of the weeds’ or to ‘zoom out’ in your thinking. Is there any hope for you? Are the robots coming for your job?
Or what if you’re already confident in your strategic skills but something still feels off. You feel like things at work are either moving too fast or too slow, and you’re not sure what else to optimise. Could you use a little refresher, or benefit from going back to the basics?
Either way—I’ve got you, my friend.
(As you might have noticed, based on the long list of articles on this blog, I don’t mind embarrassing myself on the internet if it’ll help you out somehow.)
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The four case studies
In each article, I’ll summarise the concepts and then demonstrate how they work in practice, using case studies from a leadership novella I recently wrote.
In this short and (hopefully) funny story, I showcased four fictional leaders with different goals and challenges. It follows the journeys of Claire the Control Freak, Rob the Rebel, Quinn the Quiet Achiever and Gene the Chaotic Genius, who are all on their way to being more strategic (and less annoying to themselves and others).
The link to the novella is at the bottom of this article. It’s free, no download or email is required, and you can probably finish it in a couple of hours.
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Meet Claire
In this article, we’ll focus on Claire. She’s a high achiever recently promoted to an executive position, heading up a corporate services division. She’s risk-averse, a perfectionist, tends to micromanage and finds it difficult to let go of tasks and trust others.
But she’s not a bad person. She just cares (a lot) about doing well, protecting the organisation from risk and making sure her division provides high quality services to its clients. She strives for excellence and models ethical behaviour. She also wants to impress her boss and have the respect of her fellow executives.
So, we need to be nice to Claire and not write her off as an obnoxious taskmaster.
After six months in her new role, she’s still operating in the same way she always has. She’s exhausted and her boss is starting to worry about her wellbeing, but Claire feels like she just needs to keep going.
Once she gets through ‘this month’, things should be better. Right?
We’ll come back to Claire later in the article. Let’s first look at what it means to be strategic and the misbeliefs we may have about it.
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What does it mean to be strategic?
At the individual employee level, which is the focus of this series, I see being strategic as simply being intentional in the way you think, work and lead.
It doesn’t seem that unattainable, does it? Of course not. You can do this!
I’ll unpack the definition further in the next article, but for now all you need to remember is that being more strategic is just a fancy way of saying you’re being more intentional.
(And if you’re not a newbie and are here for the refresher, thanks for making it this far. I hope you stick around, because I’d love for you to meet Claire, Rob, Quinn and Gene. They may help you feel seen or you may recognise a colleague in one of them.)
Now let’s move on to what strategic thinking isn’t and doesn’t require, which are the four myths summarised for you below. These will hopefully give you some confidence to explore the topic further.
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Myth 1: Strategic is the opposite of operational. And being operational is not as impressive as being strategic.
The reality is that operational work is how strategies get implemented, so we need both aspects. This is why most leaders, especially middle managers, carry operational, strategic and technical responsibilities simultaneously.
We don’t want to be ‘too micro’ and only focus on the detail or BAU, but we also can’t be ‘too macro’ and get carried away with the planning and visioning.
And you’ll find that employees appreciate leaders who aren’t too important to know how things actually get done—and even get stuck in themselves.
Myth 2: Strategy is reserved for executives.
It’s really not. Being strategic is a skill that can be developed at any level. You don't need a C-suite title to think about purpose, prioritise effectively or see how your work connects to the bigger picture.
If you’re an individual contributor, you may sometimes feel like you don’t have enough information to get a sense of the whole picture—I get it. But you can work to change that.
Start with your organisation’s annual report, read the news on the intranet, ask questions, tell your boss you want to know more. They’ll be impressed. If not, they won’t be able to retain your kind of talent for long.
Myth 3: You need perfect conditions to become strategic. And then you’re strategic for good.
Nope. You develop this skill in pockets of available time, amid your commitments and imperfections. And it’s not a one-off thing.
This is not fun to hear if you’re prone to ‘all or nothing’ thinking or if you’re a ‘project brain’ person like me; I’ve had to learn this lesson many times over. We either want to take a ‘one and done’ approach or we’re waiting for a magical mix of circumstances to finally start.
In future articles, I’ll share tips on carving out ‘strategic time’ in your diary and changing your mindset around what matters in your role. For now, know that you don't have to wait for the perfect moment or conditions; it’s better to start small and start now. And especially to keep going.
Myth 4: You're starting from scratch.
You’re not. You're already more strategic than you think. You don’t need to reinvent yourself; you just need to build on your strengths and make a few focused tweaks.
This will become clearer when I unpack the dimensions of strategic thinking in the next article. Just know, you’re not starting from scratch. And we all have areas we can improve on, as you’ll see in Claire’s example below.
The novella includes funny scenes—well, maybe not so fun for Claire—of her trying to wrangle Rob and his rebellious ways, blushing when asked by the CEO in a meeting to ‘take the discussion offline’, and also getting caught overworking by her boss. For now, let’s focus on how the four myths of strategic thinking apply to Claire.
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Claire and the four myths
The first thing to note is that not all myths apply equally to everyone. In Claire’s case, the one she needs to consider the most is Myth 2.
It’s not that Claire waited to become an executive to see the bigger picture. In fact, she expects her team to think strategically too. Her issue is that she’s not really walking the talk; hoarding tasks and micromanaging doesn’t empower her team to step up. She could also use the support, so developing her team would be a win-win.
Myth 4 also applies to Claire. She thinks strategically in her technical work and, for the most part, in the way she works with her fellow executives. But she needs to appreciate that her team members are not starting from scratch; they have skills she can leverage or develop further. If she does, this will help her trust her team more and delegate more to them.
And she also needs to remember that she doesn’t have the time to make sure everything is done exactly as she wants it. Sometimes things can be done differently, maybe even imperfectly, and still meet the objective.
In terms of the other myths, Claire isn’t afraid to get involved—her issue is staying out of things—but she’s generally good at moving between the macro and micro ends of the thinking spectrum.
She also started building her strategic skills early and persevered. It helped that she’s naturally intentional in everything she does, though sometimes she can over-plan and stall progress. Regardless, she didn’t wait to become a manager to be curious about how the organisation works, so developed these skills gradually. And, let’s be honest, confidence is not her issue either.
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How does this apply to you?
If like Claire, you’re a high achiever who has issues letting go, think about what’s holding you back from empowering your team, building your successors and the support you need. Consider that hoarding tasks or overcontrolling isn’t doing you or your team any favours.
Loosening your grip may feel uncomfortable at first, so do it gradually. Delegate small things, pilot and scale, and build trust over time. The mental bandwidth this will free up will be so worth it.
This won’t solve your under-resourcing problems, of course, but it’ll at least help you better utilise your existing team. And, who knows, they might even find ways to streamline the work, lessening the burden without additional resourcing.
If you report to a person like Claire, the best thing is to be honest with them and express your interest in doing more. They might be too busy mitigating risks and unaware of how their micromanaging ways are holding you back. Be respectful, but also clear and direct; they’ll lose patience with you if you tiptoe around the issue.
If you manage a Claire-type, acknowledge their contribution, then present the problem as a risk to team performance. That’ll get their attention.
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Want to see how this plays out in practice?
Follow Claire’s full story—alongside Rob’s, Quinn’s and Gene’s—across the twelve chapters of the novella. Quinn’s self-assessment against the four myths is also shown in the story.
On the novella page, you’ll find a couple of tools to help you figure out which of the four characters you’re most like and where you’re at with your strategic thinking. Don’t take these too seriously—and don’t take yourself too seriously either. Remember to have fun along the way.
I hope this is helpful.