Apr 1, 2024

The Philosophy of Strategic Planning

Terry Danylak Strategy 4 minutes

Strategy is a long-term plan. I learned this simple concept after reading Richard Rumelt’s book Good Strategy, Bad Strategy. He is known as the father of strategy.

Strategy is a long-term game. I learned this concept from Roger Martin. He is a former dean of the Rotman School of Management at the University of Toronto. He is known as a master of strategy.

Strategy is a long-term game of chess, not checkers. I internalized this concept from years of practicing strategic planning in the enterprise world while trying to build several SaaS products.


It took me a long time to internalize it because, like many humans, I don’t have the instinct to think on a long-term scale about anything, especially product development. But, through trial and error, I’ve finally internalized this concept.

Product strategy is a strange beast. On the one hand, the goal of any product is to solve a real customer problem in the most effective way possible. On the other hand, the goal of a product is to help make money and grow the business. Often, these two seemingly complementary goals compete with one another, leading to a bad product and a failed business.

When I was working on a financial management product, our product strategy was to build a product that would make the day-to-day activities of financial advisors easier and more effective. The challenge our customers faced was difficulty creating and keeping current financial plans for their clients. So, our strategy revolved around making this possible.

In the beginning, the product was to be a single-focused, highly specialized financial planning tool. And this was a good strategy to follow. This was a strategy that focused on the first goal of solving a real customer problem in the most effective way possible.

As we started to get customer feedback and new prospects began showing interest, the focus started to shift from the problem-solving goal to the growing business goal. The pressure to shift also came from the investment side. The goal of growing a business was not only ours but also the venture fund we were part of.

This shift in focus started to cause a shift in strategy. Instead of focusing all our attention on becoming the best financial planning tool, nailing it in this super specific space, we started to branch out.

A little at first, then more and more later.

We started listening to potential prospects with a large contingent of financial advisors who gave us the usual hook: if you build this feature, we’ll bring on board all of our employees. With three or four potential customers like that, our focus shifted from building the financial planning tool to building a disparate set of features and trying to fit them all together into a toolset that would be widely acceptable to the biggest range of customers in the financial advice industry.

We went from narrow focus to let’s take all the roads approach. Instead of focusing, we went wide because we thought going wide would be the best path.

Going wide is also the easy way out. You don’t have to make a decision about which path to take, which feature to work on, and which goal to focus on. Going wide is like playing checkers. It’s easy. No matter what decision you make or which move you make, you just have to make the move. Each piece on the checkerboard looks the same, acts the same and moves in the same way. It’s easy to remember and play it.

Chess is different. Chess requires focus and decision-making. Chess requires you to set a goal, think several moves ahead, execute them to get your goal and react to any countermoves by your opponents.

Focusing on a specific goal is like playing chess. It’s hard. You have to make decisions. Each piece you play with has a different set of attributes, looks different, and acts differently. You have to be disciplined to win. You have a better chance of winning because by narrowing it down, you will actually have more options open up to you.

When building and executing your product strategy, ask yourself are you playing checkers or chess?