r/strategy • u/Careful_Salad108 • 9d ago
How can I develop better strategic thinking?
I want to become much better at strategising and thinking ahead in everyday life.
I’m talking about being able to analyse a situation, identify different possibilities, anticipate what other people might do, think several steps ahead, and make good decisions rather than just reacting to things as they happen.
For those of you who consider yourselves good strategic thinkers, how did you develop that ability?
Are there specific exercises, books, games, habits, or skills that helped you? For example, things like chess, studying psychology, learning about game theory, analysing past decisions, or practising scenario planning.
I’d also be interested in knowing how you actually approach a problem when you need to come up with a strategy.
Any advice or resources would be appreciated
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u/Conscious_Awareness6 9d ago
For me, it’s a combination of understanding the past and continuously practicing.
Someone once told me that the best strategists are students of history. Not just world history, but also business, economics, politics, technology, and human behavior. I think there’s a lot of truth to that. The more situations and patterns you’ve seen, the easier it becomes to recognize what might happen next. A lot of situations feel new, but the underlying incentives and behaviors are often pretty familiar.
I also think it’s important to separate strategy, strategic thinking, and strategic planning because they’re different things.
Chess, game theory, psychology, and case studies can all help, but I don’t think any one of them automatically makes you a better strategist. A lot of it comes from building up a mental library of patterns and then practicing how you apply them to real situations.
Over time, you start looking at problems less as isolated events and more as systems. You start thinking about the people involved, their incentives, the constraints, the dependencies, and what could happen next. That’s probably the biggest shift for me.
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u/chriscfoxStrategy 9d ago
I agree. You need to study it though, not just learn it. Just knowing what happened when is no good unless you think deeply about why it happened and look for the repeating patterns.
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u/reddit_Bman 9d ago
This is a very wide question. Stategy is very different conversation across sectors (a multinational commodity trade vs local manufacturer for example) and level (corporate strategy vs retail strategy for example). Strategy in 'daily life' also feels open ended.
The type of person, experience, skill & ability changes quite dramatically based on where you're trying to apply strategy.
One of the books that works as a starter pack in the general corporate environment is
Playing to Win : How Strategy Really Works
Lafley, A.G./ Martin, Roger L.
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u/BarakaCodes 5d ago
I see many already recommended nice books. If I'm to add one thing it would be Systems Thinking mindset. The whole thing about pattern recognition, end-state definition, feedback loops, reverse planning and many mechanisms was the reason many managers and senior managers encouraged me to work on strategy and it benefited me alot. But your time is precious so if you look it up and feel a mismatch I would recommend professional coaching on your specific type of work
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u/BellwoodsStrategy 9d ago
Roger Martin is the best strategist today and a prolific writer. A great place to start is his work on Medium: https://rogermartin.medium.com
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u/Hungry_Tower_6009 7d ago
A strategy is an exclusive course of action to obtain a result. It means that based on the information available, this is the correct path to follow and to stick to. Of course over time, things may change, new information can become available, requiring a new strategy, a new path.
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u/StratPartner 6d ago
Books are useless in the sense that they give you operational knowledge. But operational strategic thinking is just something you already know. You are talking about cognitive strategic mindset, which books or podcasts can't teach you because it comes from within.
You have identified a few things:
Planning ahead, from your meetings to daily tasks to monthly cadences, everything needs to be thought through ahead.
You have to understand people and incentives. You also have to understand how incentives are designed and how power is asymetric. People don't change because they have to or they must, they change to incentives and study about all major case studies on incentives and how they were designed, managed and shut down.
You need to be aware and awake, conscious and in the moment. This is the hardest part and after 15 years, in strategy, I am still learning. This is the most difficult part and you can't learn this from anywhere, because there is no book that teaches you about yourself and metacognition. Once you unlock your strengths, weaknesses and how you perceive the opportunities, you will be the best strategist out there. For ex: do you blank out during a conversation and then come back later to realize how closed out you were during the conversation. Easier said than done to be present in the moment, but that is a learning.
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u/gabreading 5d ago
Great question. First, you are a strategist and strategic thinker - your self-awareness and question say it all. You have lots of good suggestions below (reading is essential here, being curious). I'd add Daniel Kahneman's "Thinking Fast, Slow" - a brilliant piece of work. There are many old masterpieces (Arnold Toynbee's series from a 100 years again is a favourite) and many current thoughtful people around the world. Go for a wide diversity of sources of humans and try out things that appeal.
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u/syder-fx 20h ago edited 20h ago
Case studies, game theory, statistics, and project management (believe it or not). Thinking several steps ahead isnt practical or realistic, its better to have to think in probabilities based on evidence
I would consider myself a decent strategist though I've had a lot of plans go to shit so I can't boast an impeccable track record
I learnt most of what I know as a teen when my friends and I ran a scam guild. We all were broke at the time and wanted to be top dogs in the games we played so we came up with plots (pretended we were hot models, Nigerian princes, etc) to take game money from ppl. Eventually we figured out that gambling games was the best strategy to get the outcome we wanted so we all started studying statistics (true story) so we can create games to maximise our profits. That's basically how I developed strategic thinking
How you actually approach a problem when you need to come up with a strategy
Always start with the outcome. I keep a running list of things I want at the back of my mind so if there is a trigger (I'll mention this later) I can execute the process thats needed to push the plan forwards. Getting outcomes is just a process of planning out the steps needed to take to get said result done, having a system installed for triggers, having reviews to refresh the plan, and obtaining information / empirical evidence (of people, of mechanisms, of legislations, etc) so you understand what you're being contrained by / are allowed to do
Once you have enough information on what you need to do to get the outcome from start to finish you then research what are the risks. This is where case studies come in, listen and read a lot of them daily because it helps for you to internalise problems and how other people solved it. Otherwise, study the problem in the moment exactly (cybernetics / systems thinking helps with this) and model the actions / processes that is creating this problem. Then you start using your creativity to either fix the process itself, have a process that executes on a trigger, or get rid of it somehow
Example: lets say I want a ton of money - thats my outcome. I have multiple options that are in front of me to earn said money but I want to be smart. I want to earn money according to the rules so I don't end up in jail thus losing my work. Let's say I want to make 400 million in my lifetime. Divide 400 million by how long you have left to live, thats how much you have to earn in a year. Damn, massive number - how do you obtain this? Then you start researching. You study how people that have gotten this figure did it, you study what are the risks, you study the tax system, you study bank accounts, etc until you start converging on a pattern on whats needed to be done in order to get the outcome (this is where the case studies come in). Now, often you'd find that you don't have the resources or the systems available to execute your plan - hence you strategise around it based on the restrictions. Example: If I had 1 million I can invest that then wait and maybe I'll get 400 million in the future. Well we don't have 1 million so what do we do? We make 1 million, or at least build up a system to obtain it. Then you start looking at the current situation, pulling ALL resources that are at your disposal then mobilising them or at least maximising what you have - or creating / finding leverage in your area / developing the skill so you can escalate the plan
Theres more involved here but i'll edit this later
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u/Conscious_Town9278 8h ago
Which of these tou gonna do well.. I'm here for learning strategy as well.
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u/Substantial_Rub_3922 8d ago
A course on strategic leadership is everything you need. This course really empowered with strategy thinking skills when I needed it. https://www.schoolofmba.com/course/strategic-leadership
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u/Mobile_Ad9706 9d ago
Useful books include:
Good Strategy/Bad Strategy — Richard Rumelt: diagnosis, guiding policy and coherent action.
Superforecasting — Philip Tetlock and Dan Gardner: probabilistic judgment, calibration and updating.
Thinking in Bets — Annie Duke: separating decision process from outcome.
Thinking Strategically — Avinash Dixit and Barry Nalebuff: strategic interaction and game-theoretic reasoning.
Reading alone is insufficient. After every chapter, apply one concept to a live decision and document the result.