When meeting with entrepreneurs I like to ask to see their strategic plan. Many times, I require seeing a simple strategic plan as a prerequisite before meeting so as to have a more informed conversation. Only, the vast majority of the time, no strategic plan exists, simple or otherwise. Then, when a strategic plan is present, and we go through several of the items, it becomes clear that it’s out of date and/or not remotely achievable. What gives?
I hearken back to the early days of my first startups and realize I never had a strategic plan. My strategic plan was Herb Kelleher’s famous quote:
We have a strategic plan. It’s called doing things.
While that worked well for me with a tiny team and few moving parts, as team and complexity grew, I needed a way to align everyone around a common, high-level focus. Enter the strategic plan.
Now, I believe, even with limited people and resources, a strategic plan is worthwhile. As a tool to communicate with employees, advisors, mentors, and investors, it’s invaluable.
One of the reasons so few entrepreneurs spend time on a strategic plan is the belief that it’s time consuming and difficult. From my experience, the simpler, more concise, the better. Here’s a simple guide for a basic strategic plan:
- What do you do? Why?
- Who do you serve? Why?
- What are the measurable goals? Current values? Target values?
- What are the priorities? Who owns them?
https://twitter.com/davidcummings/status/1134546561730584576
More complicated strategic plans are less likely to be updated and maintained, rendering them nearly useless. Finding a balance that has enough value but isn’t cumbersome is key.
Entrepreneurs should build, regularly update, and share their strategic plans. Keep it simple. Keep it accurate. Keep it worthwhile. Strategic plans are a valuable tool every entrepreneur should employ.
David Cummings on Startups 
Small startup teams with an energetic, actively-involved founder probably don’t need a written strategic plan because the founder has the plan in their head (whether they know it or not), and they are working closely with the team so the plan is communicated frequently and organically.
In my experience, its when the team reaches a certain size or level of complexity, that’s when the plan needs to be written down and communicated more intentionally.
One really useful thing an experienced mentor can do for a founder is, over a coffee or whatever, have a conversation and help the founder pull that strategic plan out of their mind and onto a piece of paper.