On Strategic Thinking | Candost's Blog

Newsletter Issue<br>On Strategic Thinking

I never understood what people meant by “strategic thinking” or “being strategic.” I couldn’t accept the feedback when I heard “you need to think more strategically” as well. Nobody could explain what that “strategic” word meant. I finally understood the real meaning when I tried to build an engineering strategy myself.

As I create an engineering strategy for my team and other teams, I have an answer to what it means to think strategically, especially after seeing how people think and approach strategy as we build it together.

It became clear to me that the strategy is about aligning people—agreeing on which problems to solve and in which order to solve them. It is the exercise itself that matters: deciding which direction to go and creating a plan. A plan that everyone will stand behind, even if they disagree with (or don’t like) it.

Being strategic means seeing the forest and its condition first and explicitly stating that the forest exists. Many people miss the forest for the trees. They lose a lot of time focusing on their local optimum without taking a step back to find global maxima. They try to prune the wild trees (small or wrong problems) in front of them and jump from one tree to another, while forgetting to care about the greater forest.

The root cause of this behaviour is jumping to solutions right away after seeing a problem. ”We can do this right away! It’s a tiny thing,” they say, without thinking about understanding the problem deeply. They operate with first-order thinking—focusing on immediate results and obvious outcomes. They don’t see the cost of distraction from the main goal. They focus on small wins.

If you read or watched The Lord of the Rings (LOTR), you may remember a scene where The Fellowship of the Ring has been formed in a council to take the One Ring to Mordor. Gimli is a dwarf without strategic thinking. Upon seeing the ring in real time, he hits the ring with his axe to destroy it. Little does he know that it won’t fix the problem. Then Gimli argues with Legolas that an Elf can carry the ring over his dead body; surely walking on the way to failure, as he is distracted from the main goal: destroying the ring. However, strategic thinking means thinking about the consequences of actions, which Gimli doesn’t do. It’s not about quick wins; it’s about understanding and agreeing on the biggest goal (that the Ring must go to Mordor and be unmade in Mount Doom).

Being strategic means aligning people on the path to solutions to the most important problems. While you can show someone the biggest problem, they often can’t comprehend how multiple problems feed each other, and can’t figure out the underlying factors contributing to a single problem.

During the same scene, Boromir tries to choose an easy way: use the ring to their benefit, thinking that it’s the solution (even after seeing the biggest problem). He tries to distract others, too. Aragorn takes a step to convince him. Although he joins the Fellowship of the Ring, he still disagrees with the direction and has other plans. There, Boromir sees the biggest problem—that as long as the ring exists, Sauron will exist—but can’t comprehend it. That pushes him to focus on another problem.

People who can’t think strategically lose themselves in building the perfect system design, while the business isn’t even sustainable or profitable enough to support it. Many startups fail because someone tried to build a system for millions of users when they had only a dozen.

Last but not least, being strategic is about being constructive, forward-looking . Everyone can contribute to a strategy, but not everyone can stay constructive. Enduring generosity and thoughtfulness is difficult, especially when the strategy may entail extra responsibilities. Strategic thinkers find ways to detach themselves from individual interests and focus on the organisation’s welfare. That detachment is not something everyone is willing to do (in LOTR, Boromir arrives at this point a little too late).

Strategy, of course, doesn’t end here. A successful strategy is not only about vision and agreeing on problems. It’s also about execution. Until the ring reaches Mount Doom and is thrown away, the strategy cannot be successful. Any strategy needs agile planning because of the duration of obstacles encountered along the way. However, once everyone is aligned on the direction and solving the biggest problem, the problem can ultimately be solved as difficult as the Fellowship of the Ring’s journey.

Strategic thinking is not bound to or reserved for managers and needs no title. It can be applied anywhere and by anyone. However, it’s not easy to find people who can do this consistently. It has a steep learning curve and requires practice.

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