How to Organize an Annual Planning Session

Monte Wyatt & Brad Sugars, Oct 22, 2019

Thinking strategically is a constant approach to execution planning. You need to do a strategic thinking session as soon as possible, followed by a deep-dive every year. Whether you engage a facilitator or lead the session yourself, a typical deep-dive strategic thinking session might consist of the following main activities. This is not a hard-and-fast agenda, but a listing of what we feel are key points for discussion. You should feel free to alter it to suit your needs and circumstances.

Step 1. Discuss the Current Strategy

Review how the company currently fulfills the four characteristics of a good strategy:


  • How is the company responding to existing opportunities in the market?
  • What can it do to capitalize on any future opportunities?
  • What can it do to capitalize on opportunities that it isn't dealing well with at present?


  • How is the company expanding in the market place?
  • How is it growing?
  • Are all the aspects of scalability suitably addressed, and if not, what can or needs to be done?


  • Is the company making full use of leverage?
  • If not, what can be done?
  • Are there any untapped leverage opportunities that should be addressed?


  • Does the company have access to the right markets?
  • Are there additional markets that it should be participating in?
  • Do target audiences have sufficient understanding of all the company's products and services?

Then, define the company's strategy in a sentence.

A good one-sentence strategy that indicates how the company is going to win will make the following sections about setting goals more focused and much easier. If you've done this in a previous session, take the time to review it. How are we fulfilling it? Does everyone know how we will win?

Step 2. Reflect on the previous year.

Identify the successes of the last year. What worked? What were the results? What made those successes happen? What did you learn last year? What didn't go the way you wanted? What do you need to do differently? What don't you want to experience again? As you reflect, make connections to how your successes link to the abundant mentality.

Step 3. Review the current state of the business.

Here you should review documents and factual information to bring everyone up to date on the company's statistics, including full details of the products sold and the market that exists for them, annual revenue, profit, cash flow, market share and other pertinent details. Managers should make sure they have all of the information they need reported from their teams so they're fully prepared.

Examine current trends. Discuss trends within your industry, the operating environment of your company and the internal situation within it. What effect is the state of the economy having on your industry? Are customers loyal, restless, fleeing, growing? How is all of this trending?

What caliber of staff will be required to allow you to reach future targets or goals? Will those people be readily available? Where will you find them? How much will they cost?

Examine pertinent industry facts in detail. Is new technology beginning to make itself felt? Is new technology needed?

Examine your assumptions. At this stage of the process, you'll have made assumptions based on your discussions about what your future may hold. These include suppositions about your competitors, the needs of your market, the trends you see coming, and other information you have. While your assumptions give you a lens through which to view the future, remember that they are not necessarily based on facts.

Conduct a SWOT analysis. Here, as a group, you want to draw up four different lists: the business's Strengths, Weaknesses, Opportunities, and Threats for the time period under discussion. Strengths and weaknesses relate to your organization internally; opportunities and threats relate to external factors. Addressing weaknesses, taking advantage of strengths, making use of opportunities, and managing real or perceived threats enables you to determine the areas of the company where it could be smart and/or critical to add zeros. A diversity of viewpoints is crucial: others may see things you're blind to.

Identify the top two or three that you will deal with in the coming year. This is the beginning of your action plan.

Step 4. Review the 5 Disciplines and Your Constituents Satisfaction

Focus on the change that can make the biggest difference across the board. To find it, consider the constituent group you believe is the least satisfied. Look at the two disciplines that affect that group:

  • Stakeholders are affected by Mission & Execution.
  • Teams are affected by Execution & People.
  • Customers are affected by People & Business Development.
  • Companies are affected by Business Development & Strategy.
  • The Community is affected by Strategy & Mission.

If, for example, you identify the Community as your least satisfied constituency, it means the Discipline of Strategy or the Discipline of Mission is an area of concern. How did these fare in your assessment? Discuss how and where you could add zeros to these disciplines. Which zeros would make the biggest difference?

It's likely that more than one constituent group needs attention. That's to be expected: few organizations are adding zeros in all the places they're needed. Consider the disciplines that affect the other group. Ultimately, though, work on your most critical issues first, focusing on those that, when corrected, will touch 10 other things and cause them to improve.

Step 5. Visualize the future

Now you know where you are today. You know which disciplines you need to work on, where you can add zeros, and the things you can change to make things better in the present. What will you do with this information?

To recap, a typical deep-dive strategic thinking session needs a certain agenda in order to run well. We presented you with suggestions, that you can alter to suit your needs and circumstances.

We'd love to hear from you. How have your planning sessions differed from this suggested agenda? Thank you for sharing.