My take on strategic thinking is that it’s a small set of very high level and related goals and constraints that, if achieved, are likely to lead to the success of a project. A good strategy IMO is relatively simple (a short set of bullet points), widely known, and actively used to guide decision making at all levels. Most importantly, a good strategy helps you to say “no”, because most of us have very limited resources at our disposal and we simply can’t do everything.

Here’s a simple example. Let’s say we have some SaaS product; we naturally want to maximise its revenue. There are many potential strategies. Strategy “A” might be to sell a small number of subs at a high monthly price. Strategy “B” might be to sell many subs at a low monthly price. Strategy “C” might be to fund the product through advertising. There are other strategies, too. You will pick the strategy you believe has the greatest chance of achieving your goals in your specific circumstances. (Typically the strategy would also involve conscious decisions about how the product works and where it fits in the market)

Choosing a specific strategy helps you allocate scarce resources and build the right product. Adopting a strategy “A” above could maybe let you manage without a complex self-onboarding flow, but it might also require a (potentially expensive) direct sales team. Strategy “B” and “C” might require self-onboarding, which can be tricky, but requires a less expensive marketing team. Strategy “C” doesn’t require a payment gateway or billing platform, but probably needs to be able to operate at greater scale.

> Are there some historical examples of good strategies out there?

Most strategies play out in stages over time. IIRC, Tesla had a pretty simple strategy of selling super expensive Roadsters to learn about building cars and to fund the manufacture of expensive models S and X, which in turn funded the less expensive models 3 and Y. The beauty of their strategy was that they knew why they were building a Roadster, and they weren’t distracted by wondering if they should add certain features like (I’m making this up) child restraints. The risk of this strategy was that there might not be enough rich people to buy enough roadsters to get to second base. (History suggests they made the right call)

The thing is, if you don’t have a strategy then you end up wasting resources building every little brain fart someone comes up with in the hope that your numbers will improve. But the weight of all these conflicting ideas, and the time wasted on things that don’t work out, is every bit as risky as choosing a single coherent strategy. A strategy is like a great feature filter where you can throw out half the ideas because “it doesn’t fit with our strategy”, which makes you heaps more efficient.

As long as you don’t change strategies too often.

> I'm having trouble understanding the definition of a strategy and how it differs from a plan.

In truth, a strategy is just a kind of plan, but one without much detail. It’s the high level stuff that kind of lays out the game plan. First, you need to decide that you need to build a Roadster - that’s the strategy. Then, you need to build it. That requires planning. The strategy is important because it tells you why you’re building it. The planning is important because it makes the strategy happen.