One of the biggest differentiators between companies that stay small and companies that get BIG is effective annual planning. In this three-part series, I’ll explain how to prepare for, execute, and follow through on the meeting that sets the agenda for your company’s whole year.
Today, we’re going to start with the three essential tasks the CEO needs to execute ahead of time so that your annual planning session is as comprehensive and as effective as possible.
The more prepared you and your C-suite can be going into the meeting, the more productive and effective the meeting will be coming out of it. It’s that simple.
1. Think about your goals for the year ahead.
We’re going to get to the nitty gritty details of how your company’s doing, what it can do better, and how to run the meeting.
But right now, forget about all that.
Instead, break out your crystal ball again and ask yourself the most important question a CEO can ask: “What do I want?”
Everything your company does starts with you, the CEO, looking into your crystal ball and seeing the future that you want. What’s your BIG goal? Where do you want to be at the end of next year? How will that goal feed into a 3-year goal? A 5-year goal?

Mark Moses: The annual planning session is not you, on-stage, wearing a black turtleneck and pontificating about the company’s future. It’s work – work that you need to be participating in, not orchestrating.
If you can’t picture yourself a year from now celebrating with your whole company because you achieved BLANK, then your BLANK isn’t BIG enough or specific enough.
This is the most crucial step in the annual planning process. Give yourself the time and space you need to see your company’s future as clearly as possible—before the meeting. There’s no point in holding a planning session if you don’t have a BIG vision worth planning for.
2. Assign some homework.
Get your leadership team together and prep them for the upcoming planning session. Share your 10,000 foot view of the year ahead and share some context on where you see your company and your industry heading.
At the end of the meeting, distribute the following questions and ask your leaders to send their answers to you assistant who will then collate them into the annual planning meeting workbook.
- What went right over the past 12 months?
- What went wrong over the past 12 months?
- What did we learn over the past 12 months?
- What are our greatest opportunities next year?
- What are our greatest challenges?
- How did we do on our HOTS or Goals compared to how we said we would do?
- How did we do on the specific and measurable activities we were keeping score on that we said would lead us to the outcome that we want?
- Envision you were starting a new company that would compete with the company you have today. Then answer these three questions. 1) What would you stop doing that you’re doing now? 2) What would you start doing that you aren’t doing now? 3) What would your new company do to try to put your current company out of business?
- What do you see coming around the corner that we should prepare for?
- Which potential competitors should we keep an eye on who might eventually affect our business?
- Rate your direct reports on a scale of 1-10. Whom can you coach up? Whom should we replace?
- What is the number one goal you think we could achieve next year that would have the biggest impact on our company’s growth?
Their answers – and yours – are going to form the blueprint for what you cover at your annual planning meeting.
3. Hire a facilitator.
The annual planning session is not you, on-stage, wearing a black turtleneck and pontificating about the company’s future. It’s work – work that you need to be participating in, not orchestrating.
Hiring a 3rd party like one of the coaches at CEO Coaching International to facilitate your annual planning session is always a best practice. When you sit elbow to elbow with the rest of your leadership team, discussing the same issues, confronting the same problems, and working together towards solutions, you’re sending a powerful message:
“We’re all in this together. I’m responsible for what’s working and what isn’t working same as you are. We can all do better, including me.”
Even though you may be tempted to facilitate the planning meeting yourself–don’t. If the CEO facilitates it, the other leaders might consciously or subconsciously feel compelled to agree with you and it might limit the free-flowing of thoughts to some degree. Also, you’ll be torn between being CEO and a participant of the meeting versus being the facilitator. And you won’t do either of those roles well.
The coaches at CEO Coaching International are experts at running these meetings. They know how to probe when your team is not fully bought in, dig for root causes of issues being discussed, insist on defining measurable activities and outcomes for key initiatives, call out the elephant in the room that everyone is avoiding, etc. This expertise makes all the difference between a superficial, inconsequential meeting, versus a true planning session that powerfully aligns and energizes your team around the goals for the coming year and the key activities required to get there.
In Part II, I’ll share a specific outline of what to cover in your annual planning session and how to get the best results out of the day.
To be continued in Part II: Execution
About Mark Moses
Mark Moses is the Founding Partner of CEO Coaching International and the Amazon Bestselling author of Make Big Happen. His firm coaches over 190 of the world’s top high-growth entrepreneurs and CEO’s on how to dramatically grow their revenues and profits, implement the most effective strategies, become better leaders, grow their people, build accountability systems, and elevate their own performance. Mark has won Ernst & Young’s Entrepreneur of the Year award and the Blue Chip Enterprise award for overcoming adversity. His last company ranked #1 Fastest-Growing Company in Los Angeles as well as #10 on the Inc. 500 of fastest growing private companies in the U.S. He has completed 12 full distance Ironman Triathlons including the Hawaii Ironman World Championship 5 times.
About CEO Coaching International
CEO Coaching International works with the world’s top entrepreneurs, CEOs, and companies to dramatically grow their business, develop their people, and elevate their overall performance. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 500 CEOs and entrepreneurs in more than 40 countries. Every coach at CEO Coaching International is a former CEO or President that has made big happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $1 billion, and many are founders that have led their companies through successful eight and nine figure exits. CEOs and entrepreneurs working with CEO Coaching International for three years or more have experienced an average EBITDA CAGR of 66.4% during their time as a client, more than five times the national average. For more information, please visit: https://www.ceocoachinginternational.com
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