“We cannot direct the wind, but we can adjust the sails” – Dolly Parton


Here on the New England coast, I’ve sailed my whole life. So whenever I’m looking for a fitting analogy to explain how important strategic planning is, I inevitably think of the adventures and mishaps that can come with sailing.


One weekend when I was a kid, we set sail for Block Island, a beautiful island off the coast of Rhode Island. We planned to take the journey in two legs, anchoring in Newport for the night. It started out as the perfect day with the winds on our beam, and we quickly cruised along. 


The chill vibe didn’t last long. Lacking the weather apps we have today, we were unprepared for a squall that came up, bringing high winds and lightning. Instead of arriving in Newport, we were forced to pull into a shelter harbor to regroup. 


The next day, as we headed out from the bay into the open ocean, the wind was directly in front of us. This meant we had to tack the entire time, which is basically like zigzagging your way to your destination. Three hours later than planned, we motored into New Harbor on Block Island- exhausted and excited.


Sailing is basically a crash course in why strategic planning at your company is so important. It’s not hard to say what sunny destination you want to arrive at. But how often are you pausing to regroup and take stock of where you are compared to the course you set?


In sailing, any number of factors can affect your progress: the winds, the tide, the weather, the odd lobster pot that wraps around your rudder (especially when the job of watching out for pots is given to an 8 year old). We make regular adjustments- big and small- to respond to the unexpected.  


So too in your company: talent gaps, external competition, proper estimation, crucial activities not being prioritized- can affect whether or not you make it to your destination. If you’re not periodically pausing to assess where you are, you may eventually find yourself wildly off course, unsure of how you got there.


So avoid putting off your next strategy session because the day-to-day feels more pressing. When you regularly reflect on how far you’ve come and where you need to go next, you’ll be in the best long-term position to succeed. In my next article, I’ll share the key questions to ask in your strategy session.


This is Part 1 of a strategic planning series. Stay tuned for the key questions to ask in your next strategy session.