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Annual Planning is one of the most important things you and your executive team will do each quarter. It sets the stage for the next year and is usually the session with the most difficult (and necessary!) strategic discussion.
Here are some advantages to bringing in some outside help:
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Free up your brain. As CEO, it's tough to both facilitate and participate. Free up your brain for more strategic thinking and have someone else worry about the projector, schedule, and content.
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Get the most bang for your buck. Annual Planning is the time to get the most out of your investment in a professional facilitator. All of your quarterly planning sessions for the upcoming year will refer back to your Annual Plan. Invest in getting it right.
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Stay on track. Keeping the team and the discussion focused is largely a function of the facilitator. Having an outside party there to bring things back into focus removes the drama from what might be a heated discussion.
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Ask the tough questions. Brutal facts are easier to face with the support of someone with an outside perspective. The facilitator can also ask tough questions that might be emotionally charged when asked by a member of the team.
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To Do or Not to Do. A good Annual Planning facilitator will also talk the team through a "Won't Do" list as well as a "To Do" list. This is vital for a focused Annual Plan, and it's a step that most teams miss when they do the session on their own.
Tiffany Chepul
Tiffany is a Rhythm Consultant who helps leadership teams turn ambition into execution. With a strong foundation in sales and public relations, she brings both strategic clarity and real-world communication expertise to every engagement. Tiffany specializes in building high-performing Think Plan Do Rhythms that align teams, sharpen focus, and drive purposeful growth. She’s passionate about helping organizations move faster, stay accountable, and achieve meaningful, measurable results.
Connect with me on LinkedIn.