Planning should create momentum, not delay it.
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Many startup leadership teams struggle with strategic planning.
They know they should do it. They rarely make time for it. And when they finally do, they often overcomplicate it, fail to integrate it into how the company actually runs, or spend so long planning that execution suffers.
The result is predictable. The plan gets written, discussed once or twice, and quietly forgotten.
I’ve been on both sides of this. I’m biased toward action and have a low tolerance for discussions that don’t produce outcomes. For years, that bias made it hard for me to do true strategic planning. But at some point, I learned that if you want to run a company well, you need a repeatable way to decide where you’re going and prioritize the most important work to get there.
What follows is the simple planning cadence and framework I landed on after some trial and error. It’s rooted in OKRs as the output, flexible enough to adapt to different cultures, and robust enough to scale without becoming too bureaucratic.
Strategic planning is deciding where your company is going and what you are going to prioritize to get there.
At its simplest strategic planning looks like this:
That’s it. Everything else is noise.
If people don’t know where the company is headed, they will make up their own priorities.
Planning gives you a way to: