The Annual Planning Playbook
Understanding How People, Possibilities, Priorities, and Purpose Transforms Tackling Annual Planning
In November, I spent the day on Slough Farm—a glorious, cozy, inspirational farmhouse with tall ceilings that lift the imagination and sweeping windows that open onto tall grasses rolling toward a surfside beach. I was there facilitating a nonprofit’s strategic planning session, but the setting did as much teaching as I did. Somewhere between the salt air, the laughter, and the inevitable pile of Post-its, I found myself thinking back to the old “Four P’s” we learned in school. Only this time, the framework felt different—more human, more modern, and far more useful for how organizations actually grow today.
The first “P” is People. Organizations work better when teams understand themselves and each other. Tools like FourSight help teams see how they naturally approach problems—who clarifies, who ideates, who develops, who implements—so they can work with each other’s strengths rather than around them. Watching people’s eyes light up as they finally have language for how they generate creative energy is one of the great hacks of team building. It bridges humor, understanding, and momentum as a group gets to work.
* First Hack: Invest in FourSight or a similar tool for your team to complete before the offsite.
Once teams have that foundation, they can open up to Possibilities. Creativity requires space—both literal and mental. That means getting offsite, covering walls with Post-its, walking a property with fresh eyes, challenging assumptions, and giving yourself permission to critique and iterate. When teams play, explore, and rethink old patterns, new ideas emerge with more energy and less friction.
* Second Hack: Make the time to get offsite.
Only then is it time to focus on Priorities. Every organization has limits—time, capacity, resources—so choosing what matters most becomes an act of discipline. Identify the themes that will drive the mission forward and make sure everyone knows how their work connects. Tools like V2MOM translate intentions into methods and measures. Cascading goals—and sharing them transparently—lets every person see how their efforts ladder up.
* Next Hack: Set up a shared Google Sheet with dropdowns so individuals can align their personal goals with cross-organizational priorities, document who leads and supports, and commit to quantifiable KPIs.
And all of this leads to the fourth “P”: Purpose. When people understand themselves, explore possibilities with curiosity, and focus their priorities with intention, they move forward in shared purpose—strengthening culture, deepening commitment, and transforming what an organization can achieve. And it’s important to remember: the purpose of planning is alignment and focus, not endless bureaucracy or wordsmithing SMART goals on ChapGPT.
The real questions are: Are we coming together? Are we raising the bar? Are we focusing on what matters most? Are we challenging each other on what is realistic, what is a WOW, and what is a WAIT?
* Final Hack: The conversation trumps the artifact. The artifact simply gives you something to anchor to throughout the year.
Purpose is ultimately a shared contract—what you stand for, what you commit to, and what you will move toward together.
