What are Quarterly Strategy Sessions and How They Can Help You
I first started doing Quarterly Strategy Sessions with my friend Stef Caldwell. We love peer-coaching one another through life and career. Stef has a way of seeing me more clearly than I see myself at times. Our regular cadence also allows both of us to reflect and witness each other’s growth over time. We both regularly say, “This is really interesting growth since the last time we talked.”
We don’t pay each other. We just have a recurring calendar invite to chat once every three months over Zoom.
I now also have Strategy Sessions with my friends and colleagues Shamir Johnson, Taylor Elyse Morrison, Adrienne Rose White, Andrea Jacobsen, and Michéal Breslin.
These aren’t paid sessions; they’re more like informal catch-ups. Generally, this is what happens during these calls:
We take turns updating one another on what’s going on in life and business. We ask for strategic input and brainstorming so we can bounce ideas off one another.
We celebrate wins and brainstorm things that aren’t working or feeling good.
We offer support, solutions, and ideas. Especially when it comes to solving problems, other people often have insights that we are missing because we’re too close to the problem.
We encourage each other to balance taking care of ourselves while also continuing to play big and reach our goals.
We hold space for the interesting, ambitious, creative humans that we are.
We remind each other of lessons learned from previous sessions so we don’t go down a rabbit hole.
We make the journey a lot less isolating for one another.
Benefits of Quarterly Strategy Sessions
Witness someone else’s journey. What’s going on in their life and career? What problems can you help them solve? Their journey can inform yours and vice versa.
Be of service and lend a helpful, listening ear. Unlike paid coaching or mentoring, Quarterly Strategy Sessions are a peer-to-peer space. You take turns helping each other on the call. It feels good to listen to someone and weigh in with your reflections. Over time, you start to really understand someone’s journey.
Create space away from your daily tasks to reflect and gather wisdom. This space on your calendar is carved out ahead of time for reflection, asking for help, and being of service to someone else. You don’t have to think ahead to plan something; it’s already planned out for you!
Have more fun on your journey with camaraderie and connection. Building a business, writing a book, and really any creative pursuit can be an isolating experience when you’re building by yourself. There’s also often a lot of uncertainty. Being on the journey with someone else provides context, fun, and support.
Notice progress over time. Given that you meet every 3 months, you’ll start to notice that a lot of progress has happened since you last chatted.
Receive support. It not only feels good to witness someone else’s journey, it also feels good to have someone be there for yours. You can ask questions, ponder deep thoughts that have been on your brain, etc. The key part of this relationship is your like-minded ambition!
How long should each session be?
I schedule mine for 60-90 minutes.
How should you divide your time together (and what if your partner takes up more talking space than they should?)
Remember to split the time with your partner so you get equal talking space. Setting a timer can help so there’s a clear cut-off time for the first person. If your partner takes up more time than they should, you can always gently nudge and remind them of how much time is left. If a partner consistently can’t divide the time in half then it might be time to find a new strategy partner.
What if you don’t want to continue having quarterly strategy sessions?
Since it’s a recurring calendar invite, you’ll want to message your strategy partner and let them know your bandwidth has changed or that you no longer need the space. If you let your partner know what’s going on, they will hopefully be more than understanding.
Next steps
I don’t know a lot of people who are jumping on Zoom calls with friends and colleagues outside of work to strategize their ambitions. It’s meaningful and impactful the way we are helping one another.
This has happened organically in my life with the creative and ambitious people I’ve met along the way, and it’s something you can create for yourself, too.
I recommend reaching out to someone in your network, whether it’s a friend, peer, or colleague who has similar ambitions to you. Perhaps they also have an entrepreneurial spirit like you. You can ask to jump on a call to chat through your similar journeys and from there, if it’s a fit, you can ask to meet regularly.
Meeting quarterly is usually a good cadence because it’s not a huge time commitment for either party, but it’s also often enough to be impactful over time.
If you set one up, let me know! I’d love to hear how it impacts you.
