Everyone tells you to think strategically — nobody tells you how to do it in practice. This article gives the concrete recipe: the open-water swimming analogy, the one decision criterion (does this take me closer to or farther from my north?), seven do's, three don'ts, a real case of a CEO making operational decisions while strategic ones waited, and the three concrete benefits of lifting your head out of the water.
Every consultant, every management book, every keynote speaker says it: "think strategically", "look at the long term", "don't get lost in operations". Correct — I won't argue with that. The problem is that nobody tells you exactly how to do it. And when you arrive at the office, there are ten urgencies, three meetings and a crisis. Strategy waits — again.
This article isn't about why strategic thinking matters — you already know that. It's about how to do it in practice: what to do, what to avoid, and why if you don't, you're failing at your main job.
The open-water swimming analogy
I like open-water swimming. Especially on the Uruguayan beaches that face the Atlantic Ocean — Punta del Este, Piriápolis, La Paloma, sometimes Punta del Diablo. These are beaches with currents, and even in a well-organized competition, for most of the route it's hard to see the markers or buoys.
If I just stroke and breathe, I don't know where I'm going. At best, I drift off the ideal path. At worst, I'm being pulled out by the current and putting myself in danger. I'm moving — but I may be moving without direction.
Orienting yourself takes more than just lifting your head. You have to do something else: lift your body up a bit, raise your head properly, gain real perspective. Spot a reference on the shore — a building, a lighthouse, a tree — and swim toward it. But that takes effort. It's not a natural movement.
Every so many strokes, I slow down, lift a bit of my back out of the water to raise my head, see the north, and if necessary correct course. That's exactly what having a clear strategic north means in a company.
The most important decision criterion
There's a question every Director or CEO should ask before making any relevant decision:
Does this decision take me closer to or farther from my strategic north?
It seems obvious — but believe me, it's not. In practice, decisions are made out of urgency, pressure, opportunism, or because that's how it's always been done. Rarely out of explicit strategic alignment.
The heaviest-weighted criterion in any important decision must be that one: does it take you closer to your north? Not the one that generates the most revenue this quarter. Not the one that puts out the fire fastest. Not the one the loudest client likes most.
If you don't have your north clear, you can't apply that criterion. And if you can't apply it, you're sailing blind — stroking, advancing, but without really knowing where to.
The Do's: how to lift your head out of the water
I like being direct. Here are seven concrete ideas to start thinking strategically for real:
Not three-minute LinkedIn articles. Management and leadership books specific to your industry and role. Good to Great by Collins. Empowered and Inspired by Cagan if you're in technology. Thinking, Fast and Slow by Kahneman if you want to understand how you make decisions. Reading pulls you out of the present and gives you perspective.
Make time to acquire new skills, connect with people in similar situations, question your leadership style and think about the future you want. Executive education programs are usually an ideal place to concentrate all of this — not because of the credential, but because of the forced pause and the contact with peers.
Bill Gates did it twice a year as CEO of Microsoft. He'd go alone to a cabin in the Pacific Northwest forest, fully disconnected, with stacks of papers and books. No family, no team, no meetings. Only read, think, write, sketch ideas. Out of those weeks came, among other things, the launch of Internet Explorer.
You don't need a cabin in the woods — a few days out of the office, alone, reconnecting with "why are we doing all this" is enough.
Spaces like Vistage, Endeavor, leadership associations — or simply a monthly lunch with trusted peers. That's where you find disinterested perspectives, no agenda. Building that trust is hard, but when it works, it's one of the most valuable inputs there is for strategic thinking.
We wrote about this in detail in this article. AI can make tasks that aren't yours even more tempting to do yourself — because now they're easy and fast. That doesn't make them your job. It makes them a more sophisticated trap.
One hour a week — at minimum — that isn't a meeting, isn't email, isn't fire-fighting. It's time to think with perspective. Some call it deep work. The trick is putting it on the calendar as if it were a meeting with your most important client.
And the one I like most. Pomodoro-style, but with a specific focus: in that pause, ask yourself whether the next task is really yours as Director or CEO, or whether it would be better delegated.
This isn't easy because being busy makes us feel productive. But usually what we achieve by being so busy is avoiding the question of whether we're doing our job — or someone else's.
The Don'ts: what to avoid
Most are the opposite of the do's already listed, so I'll be brief. Three things I really don't recommend:
Don't confuse motion with progress
Being very busy doesn't mean doing the right thing. An executive with a packed calendar who doesn't dedicate time to strategic thinking isn't being productive — they're being reactive. And being only reactive, it's hard to make sure you're swimming toward the desired north.
Don't postpone hard conversations
The tendency when buried in operations is to avoid anything requiring emotional energy: the conversation with the underperforming leader, the decision to leave a market, the conflict between partners. Those conversations are exactly the Director's job. Postponed, they carry compound cost.
Don't build operational dependency on yourself
If you're the bottleneck for decisions others could make, the problem isn't that your team is bad — it's that you're not developing or empowering them. Every time you make a decision someone else should make, you steal learning from them and strategic time from you.
At one of the companies we work with through Buho Advisors there was a brilliant CEO: professional, committed, hardworking like few others. But he had a weakness: he preferred to do things himself rather than teach someone and tolerate errors in the process. At first, it made sense. The company was small and he was the best at almost everything.
The problem is he kept at it when the company already had 40 employees. For example, he himself reviewed issued invoices, managed collections follow-up, and called late clients personally. He did it very well, achieving high collection rates and clients happy with the direct treatment. The team, happy that someone was solving it.
There was no malice. There was no ego. Just a pattern no one questioned until it became unsustainable.
Concrete benefits
I could spend hours listing the benefits of lifting your head, getting out of the water and looking at the strategic north. I'll narrow it to three:
- Better decisions. When you have a clear north and time to think, decisions become more coherent, consistent and faster. Not because deciding is easy, but because you have the criterion in order. It doesn't guarantee you never get it wrong — but you'll get it wrong less often.
- A stronger team. When the Director leaves space, the team grows. When the CEO is the best executor of everything, the team learns to wait for instructions. Delegating well and thinking strategically aren't separate things.
- The ability to see what's coming. Executives who lift their heads out of the water also see when a boat is coming head-on. They detect market shifts, identify opportunities others don't see, and arrive at important conversations with perspective.
Conclusions
Nobody else is going to do this for you. It's not the team's responsibility, not the board's, not the shareholders'. It's yours — that simple. And if you don't do it, you're failing at the main thing: leading.
Doing it doesn't guarantee you'll reach your goals. No habit guarantees that. But it considerably increases the probability — because you're swimming with direction, not just stroking with energy.
Lift your head. Look far. Correct your course. And keep swimming.
Frequently asked questions
What does 'thinking strategically' mean in practice?
It's not about having a 40-page plan. It's about knowing, at every moment, where the company is heading — and being able to answer that question with clarity in every decision. It means pulling yourself out of the operational flow periodically — like a swimmer lifting their head to verify direction — and applying a single criterion to every relevant decision: does this take me closer to or farther from my strategic north?
Why don't executives think strategically even when they try?
Because operations always win in the immediate term: there are ten urgencies, three meetings, and a crisis. Strategic thinking requires deliberately slowing down — and that's not a natural movement. Like gaining perspective in open water: you have to make an effort to lift your body up and raise your head.
What are the concrete tools for thinking strategically?
Read management books (not three-minute articles), train yourself through executive programs, reserve a week a year to think without interruptions (the 'think week' Bill Gates practiced), seek conversations with trusted peers, avoid using AI for what isn't executive work, block one hour a week for deep work, and take five-minute pauses between tasks to verify whether the next one is really yours to do.
What mistakes should a Director or CEO avoid?
Confusing motion with progress (being busy doesn't mean doing what's right), postponing hard conversations because they require emotional energy, and building operational dependency on yourself — stealing learning from your team and strategic time from you.
What are the real benefits of thinking strategically?
Better decisions, because with a clear criterion you decide more coherently, consistently and faster. A stronger team, because when the leader leaves space, the team grows. And the ability to see what's coming — market shifts, opportunities, risks — before competitors who only swim with energy without looking at the horizon.
Buho Advisors — Technology advisory for boards in Latin America.
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