Most Q4 planning starts with: “What do we want to accomplish next year?” I offer these 19 questions to be with & work through:
Founder
– What role should you actually be playing?
– What are you still holding that you shouldn’t?
– What decisions belong to you?
– What needs to change in how you lead?
Business
– What is the business actually becoming?
– What should stay?
– What needs to be released?
– Where is the current model creating friction?
Positioning
– Does the market understand what this company is becoming?
– Is the story keeping pace with the business?
– What needs to be said differently?
Structure
– Who needs to own what?
– What systems are missing?
– Where are decisions getting stuck?
– What needs to be delegated, automated, eliminated or rebuilt?
Strategy
– What is the actual strategic direction?
– What opportunities belong?
– Which ones don’t?
And crucially, what kind of life are we actually building next?
– What is your order of priorities, and how might your daily routines and commitments be at odds with them?
– What are your core values that you may not be upholding?
– Simply, what would you like more of?
Then, we don’t stop at insight! The buildout becomes the thing that separates our work from a planning retreat.
Sara
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Sara Oblak Speicher, MBA, is a former elite athlete turned fractional leader and strategic advisor, trusted by founders and elite performers who are navigating growth, transition, and reinvention. After 18 years in NYC, she is now based in Slovenia, architecting story, strategy, structures, and systems for her global clients. 600+ engagements and $60M+ in measurable client impact in the last few years alone.
