Many startup leadership teams struggle with strategic planning. It’s often something companies want to do but don’t make time for. When they do undertake the effort, they don’t integrate their plans into their business operating system, and they end up being outdated and forgotten as soon as planning is over. Another mistake is over-indexing on strategic planning and spending far too much time planning and not enough time executing.
Until you have gone through a few planning cycles, it can be hard to create the discipline to do it in your company and strike the right balance of effort.
I tend to be biased toward action (and an aversion to discussions that don’t yield immediate outcomes), so I personally had trouble consistently planning for many years. But I found that at some point, to run your company well, you have to figure out how to have a repeatable, effective framework for strategic planning.
Here’s the cadence, process, and framework I finally settled on after much trial and error. It’s really rooted in OKRs as the final output. I find it robust enough to be high-impact but simple enough to allow for flexibility. I think it works for teams and founders who are planning adverse as well as those who fully embrace planning. It scales to a company that’s upwards of $50m in ARR (but after that, it probably needs some adaptations and additions to work well at a larger scale). It can also be tweaked easily to adapt to any startup culture.
Strategic planning is the process of determining the direction of your business. In a simple approach, you assess where you are and discuss where you want to go. Then, you plan ahead, set the course, communicate it, do it, and measure it.
If everyone across your company doesn’t know where you want to go, how will you get there?
Through planning, you set goals and define high-level approaches to achieving them. This helps ensure you and your entire company focus on the right things at the right time.
With planning, you are able to set a strategic agenda and priorities for the short, mid, and long term. As you cascade the strategic agenda to the organization, you ensure your entire company is aligned with the right areas of focus and effort.
More than anything, planning can help your company radically focus on the most important things and drop the distractions that aren’t adding value to the company’s strategic agenda.
Here is a process for strategic planning that isn’t overly complicated. You can do this with your executive leadership team (your direct reports). As a company leader, you should think about these things in advance, but come to the planning sessions ready to listen more than you talk.
Depending on the stage of your business, there may be a lot or a little to review. Essentially, you are reviewing the state of the business today. Topics for this step include: