091: Quarterly Planning with Charlie Gilkey

“I’m always stumping quarterly planning for business owners. It’s the Goldilocks horizon for strategy execution, project scoping, and team alignment.” Today I’m talking with Charlie Gilkey about why the quarter is an ideal time unit for strategic planning, how to apply his stepwise Momentum process to mapping projects and goals, and striking the balance between visioning and planning. Charlie also had an interesting response on why tracking metrics matters . . . and it’s not what you might think.

More About Charlie: Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing (2019) and The Small Business Lifecycle (2012), founder of the new Momentum app, and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a Ph.D. in Philosophy. He lives with his wife, Angela, in Portland, Oregon.

🌟 3 Key Takeaways:

• 18 months is a typical “now” horizon for established businesses, whereas three years can get mysterious.

• There’s a difference between your visioning horizon and your planning horizon; when deciding what to work on, consider cash flow, visibility, and opportunity.

• When you hit a strategic, urgent, recurring logjam, ask: “What experiments can I try?” instead of obsessing over numbers. It’s so that we can build alignment with the team and take pressure off of the owner to be the Chief Prioritization Officer.

📝 Permission: Drop at least one project that does not create cash flow, opportunity, or visibility.

✅ Do (or Delegate) This Next: Identify the next two quarter-sized projects that will move you toward your biggest 18-month business goal.

📘 Books Mentioned:

• Free Time: Lose The Busywork, Love Your Business

• Pivot: The Only Move That Matters Is Your Next One

• Start Finishing: How to Go from Idea to Done

• The Small Business Life Cycle: The No-Fluff Guide to Navigating the Five Stages of Small Business Growth

• The Road Less Stupid: Advice from the Chairman of the Board

• Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality

🔗 Resources Mentioned: 

• Charlie on the Web, Instagram, Twitter, Facebook, LinkedIn

• Charlie’s podcast: Productive Flourishing podcast

• App: Momentum App

• Free Planners: Momentum Planners

• Article: Cashflow, Opportunity, and Visibility: The 3 Goals of Any Business Activity

Related Podcast Episodes: 035: The Long Game with Dorie Clark, Pivot 136: Start Finishing—Pricing, Projects, and Momentum Planning with Charlie Gilkey

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