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In Episode 9 of Our Readiness Lens, Sheri is joined by two experienced tax professionals, Denise Hanlon (Hanlon CPA) and Jane Watkins (Tax Time Services), for a powerful conversation about strategic planning beyond the walls of your business. While Sheri’s firm works deeply inside operations—accounting, advisory, payroll, and performance—the truth is your business is only one slice of your financial world. Retirement, estate planning, ownership structure, legacy goals, tax strategy, and risk management all intersect with operational decisions. This episode explores why business owners must move beyond siloed conversations and instead build a coordinated advisory “village” that works together to protect, grow, and future-proof the business. Timestamps 00:43 – Introduction to strategic planning as a growth multiplier 02:00 – Why business owners need to think beyond the 12-month cycle 05:00 – The risks of ignoring entity structure and long-term planning 07:45 – Why tax conversations feel overwhelming for clients 09:30 – Real-life planning mistakes and unintended tax consequences 12:00 – Estimated tax payments and operational follow-through 14:00 – The “village” or advisory team concept 18:45 – Why size doesn’t matter—small businesses need planning too 23:30 – Estate planning and probate horror stories 27:00 – Crisis planning vs proactive planning 31:00 – The importance of defining your end goal early 35:00 – Why strategic coordination protects against business killers 36:00 – First steps: Start small, start somewhere Mentioned Resources R Accounting Group — Advisory support, resources, and systems for business owners ready to scale with intention: https://www.raccountinggroup.com/home Episode Guide: https://gamma.app/docs/Strategic-Plan... Connect with Sheri on LinkedIn: / sheriradler Connect with Denise Hanlon on LinkedIn: / denisehanloncpa Connect with Jane Watkins on LinkedIn: / janemhwatkins If this episode resonated with you, share it with a fellow business owner or client who’s ready to turn structure into strategy. And don’t forget to follow R Readiness Lens for more conversations on business readiness, clarity, and growth.