Earlier, I shared my philosophy that strategic planning is a lot like sailing. When you’re under sail, conditions can change quickly. You frequently need to revise and refactor your plans along the way. 

In this case, instead of assessing the winds and weather, we use probing questions to dig into what’s enabling– and standing in the way of– your company achieving its most important priorities. Then we use those insights to confirm or adjust your plans. 

Successful founders use strategic planning–both annually and quarterly–to get to their vision as quickly and as profitably as possible. 

At each strategy session, you’ll look back on your progress, your challenges and other factors affecting what you’re trying to achieve. Then you’ll apply that knowledge to your upcoming plan. 

I always recommend quarterly strategy sessions, because a lot can change in three months for fast growth companies, and it enables us to pivot quickly. 

But it’s essential to take a top-level view at the end of the year as well; looking towards the full year ahead; a.k.a., the next big leg of the journey. 

In annual planning sessions, we ask three key questions: 


#1 Have we arrived at where we thought we’d be by this point?


Start by reviewing your company’s key metrics and goal plans. 

Did you achieve what you expected this year? If so, what people, processes, tools and other factors helped make that possible? If not, why not and what can you learn from it? 


#2 What adjustments do we need to make to stay on course? 


Take some time to reflect on your top priorities. 

Does your destination remain the same? Does it need to be adjusted now that you’re closer and have more information? What are your competitors doing and how might that change your direction? What changes or investments do you need to make to your people, processes and tools to stay on course?


#3 What are our new annual priorities? 


When you’ve arrived at the end of the next year, what does your destination look like? What have you achieved? What new features or products have you created? How much has your customer base grown? 

Once you’ve answered these questions, create a short, specific list of your top priorities for the year. This ensures that your team focuses their effort and energy on the most important outcomes.

Next, chunk your annual priorities into quarterly priorities to keep a clear line of sight. Then, cascade your annual priorities into a short list of team (or department-level) goals. Lastly, set individual goals for each team member that align to their team goals and the company’s top priorities. 

Next up: why and how to bring your people into your strategic planning process.