Annual Strategic Planning: Reflecting and Planning for a Great Year

By Patrick Thean

annual planning 2020

2019 is coming to an end. I find myself flying across the Atlantic Ocean to Singapore for my mother’sannual planning 2020 birthday. From Singapore, I will then make my way to Switzerland to help a client build a great plan for 2020. A friend asked me how I can stand making these long flights to Singapore on a regular basis. I actually enjoy these trips. I start with making sure I have a nice comfortable flight. Singapore Airlines never disappoints in this department. Then, I am thankful for the gift of time. I am left alone to relax, think, and reflect. On this trip, It’s given me time to reflect about 2019, on both the business as well as the personal side to come up with a better plan and design for 2020.

A common mistake leaders make is to focus their reflection only in the areas that did not go so well. Our brains naturally take us on a problem solving trip. We want to do better, be stronger, so naturally we think about things we did not do so well. But we need to reflect on both the things we did well and the things that did not go so well.

Here are some recommendations to prepare for your strategic annual planning session:

  • How did you do on your top 3 annual goals for this year?
    • Did you write these goals well? Did you clearly describe what success looks like?
    • Most of your goals involve others. Did you share with them what success looks like? And did you all get aligned on what success looks like?
    • Did you have a good execution plan to get these goals done last year?
    • Are you going to leave the strategic planning session without an execution plan?
      • Hint: Your answer should be no. If you don't know how you are going to hit your goals, you won't. A planning session without an execution plan is just another meeting.
  • Can you identify any bright spots and successes you can repeat?
    • We are so busy looking for problems that we often don’t see the great stuff in front of us that we can learn from and replicate across our company.
    • These are the diamonds in your backyard. They are hard to find. And you won’t find any if you do not look intentionally for them.
    • If you find any of these diamonds, reflect on what happened, how to do it again, and even replicate these across your company.
  • What did not go so well and why?
    • What took too many resources and still did not succeed?
    • Why did this happen? What steps should you take next year to change this?
    • What can you learn about the project as well as the teams on these projects?
  • What are the critical issues that you need to discuss going into the planning meeting?
    • What data do you need in order to make the proper strategic decisions during the meeting?
    • Who needs to be part of the planning team? Do you have all of the right people in the room? You need to keep it small, but not so small that you have blind spots.
    • Follow the strategic planning process and use a parking lot when a discussion is productive but can be picked up at a later date with the right people in the room.
  • Alignment across teams. So many projects these days are cross functional. How did your enterprise projects fare?
    • Did these go well? And if they did, why did they go well?
    • If they did not go well, what do you need to change for a different outcome next year?
    • Did all of the departments understand what was expected of them to contribute to the company's goals?

As you reflect, think about what the crucial discussions are that you need your team to work on and get aligned for the next year. If you have not already planned your year or set a date to meet and work on your plan with your leadership team, you should do that right now. If you do not have an execution plan that you and your team are confident in for next year, then you probably won’t have a great year next year.

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I recommend the following for an effective strategic annual planning session:

  • Make a list of your top discussion topics based on your reflections on what worked well and what could be done better next year. Create a thorough annual planning agenda based on those reflections to make sure that you have a plan to cover all of the subjects that you need to address. Follow this meeting agenda to keep on track, but don't cut off productive discussions.
  • Bring in a professional annual planning facilitator to help engage your full team in these topics. It is important to discuss and debate, get all sides and opinions out. You will receive a much better result by participating actively in debating topics rather than facilitating the discussions. The Return on Investment (ROI) of hiring a professional will pay off every day of the next year.
  • Review your vision statement to make sure that you keep it in mind during your annual planning meeting.
  • Perform a SWOT Analysis to ensure you are keeping abreast of your industry and the opportunities and threats that exist.
  • Spend extra time discussing what success looks and how each team or department contributes to the success for each initiative. Lack of alignment and lack of clarity on how to execute as a team is often what causes mistakes and rework.
  • Consider replacing static spreadsheets with dynamic systems. If you are still running your business via email and spreadsheets, you will run into a growth ceiling. Make this the year you invest in the future of your organization.
  • An expert strategic planning facilitator will be able to help in these ways:
    • Get your topics on the table and facilitate the right discussions
    • Look for areas that have not reached alignment and help you get aligned to kill departmental silos before they happen
    • Help you gain clarity and focus, which is a prerequisite for alignment and good execution. You need a good vision of how to do the work for great execution and results.
    • Direct you to think about how to cascade this to your teams in the right aligned way
    • Assist with the organizational development of your team, walking you through the strategic planning process

If you need help and want a professional strategic planning facilitator, call us. We have helped companies develop over 10,000 strategic execution plans and have helped companies visualize and write over 200,000 SMART goals. Strategic planning meetings are better with experts and help you crush your revenue goals.

Need an Expert Planning Facilitator? Contact Us


Looking for more Annual Planning Meeting information to help get you started? Check out our additional resources:

Annual Planning: 9 Tips to Focus & Align Your Team with a Great Plan

Annual Planning Playbook: 5 Steps to Create a Winning Annual Plan

How CEOs Can Avoid High-Cost Mistakes in Annual Planning

Best Practices for Annual Planning

Rhythm Systems Annual Planning Resource Center

Photo Credit: iStock by Getty Images

Patrick Thean


Photo Credit: iStock by Getty Images