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Part 2: Execute An Annual Planning Session That Will Set You Up For Success in 2021

One of the biggest differentiators between companies that stay small and companies that get BIG is having an effective Annual Planning Process. In this three-part series, we’ll explain how to prepare for, execute, and follow through on the meeting that sets the agenda for your company’s whole year. CLICK HERE for Part I: Preparing an Effective Annual Planning Session During the Pandemic.

Now that you, your leadership team, and your professional outside facilitator have completed all the necessary prework, it’s time to talk about how an effective one- or two-day annual planning session actually works.

Remember, this is THE most important business meeting on your calendar for the year. And, given the fact that your 2021 plan has to account for radical changes in global business, this will be one of the most important meetings your company will ever have, period. Done well, it will set the stage for explosive growth and BIG accomplishments.

Year after year, we’ve seen the following template help companies at every stage of growth get better. And as we’ve completed our own online pivot during Covid-19, we’ve learned how to adapt this template to accommodate socially distanced in-person sessions as well as virtual planning sessions.

But we also recognize the importance of allowing for nuance and flexibility in an annual meeting plan, especially when so many companies are facing critical turning points. Over the course of the meeting, a skilled facilitator will know when to prod, poke, drill down, zoom out, press, or pivot in order to meet the exact needs of that leadership team at that moment.

But first, let’s nail down the basics. Here are some key best practices to help you get BIG results from your annual planning session.

1. Align expectations. You’ve all done the prework and have come into the meeting with your own ideas and expectations. Now, the facilitator will ask each attendee to share their expectations. Then, he’ll distill those responses into a set of statements that everyone is aligned with. By the end of this brief discussion, it should be clear to everybody “what success looks like” for this meeting.

2. Review prework. As you review the prework, what pops out? What patterns are apparent? What is becoming clear?

As we discussed in Part 1, if every answer revolves around Covid-19, your attendees are going to have to dig deeper. The pandemic probably exposed more problems with your business than it caused. Those deeper structural issues that would have dragged you down eventually in any environment are where you need to focus.

Mark Moses: A skilled facilitator will know when to prod, poke, drill down, zoom out, press, or pivot in order to meet the exact needs of that leadership team at that moment.

3. Review last year’s results. On a scale of 1 to 10, how well did you execute on last year’s plan? How large is the gap between where you are and where you’d aimed to be? What could you do to improve your execution this year? Were any of your answers to the prework informed by your results from the past year? Aside from your Covid-10 pivot, are there any problems or issues from the past year that will need to be resolved this year?

4. Determine high-level outcomes. Now it’s time to crystallize the specific and measurable outcomes you want to achieve. As facilitators, we typically start by looking out three years: just far enough to achieve a Huge Outrageous Target (HOT), but not so far that it’s easy to forget about those long-term objectives. From there, we’ll zoom in and look at the next 12 months and determine the specific objectives we want to achieve that will keep us on pace to hit our long-term HOTs.

5. Determine specific initiatives. Setting goals is the easy part. The hard part is determining the specific and measurable initiatives that will lead to achieving those goals and building towards your HOTs. A skilled facilitator will walk you through a process that could include divergent thinking, convergent thinking, prioritizing, voting, and challenging so you arrive at a manageable number of initiatives that have a high probability of leading to your HOTs. This year, that list might include some new opportunities that the pandemic has created, such as buying distressed assets, expanding your community outreach, or recruiting top talent from the wealth of displaced workers.

6. Drill down and assign ownership. Break down your annual initiatives and identify the specific, short-term milestones along the way to measure your progress. We’ll answer such questions as:

  • What will it take to guarantee it happens?
  • What will stand in the way of making it happen?
  • How will we overcome what stands in the way?
  • Who owns it?
  • When will it be done?
  • How will we keep score?

7. Commit to Make BIG Happen. We’ll end the meeting with a strong, united commitment on the plan and a clear understanding of “who will do what by when.”

Okay, now we have an actionable, measurable plan in place and a set of clear expectations for every member of the team. But there’s a crucial third step to the annual planning process that many companies skip.

In Part III, I’ll talk about how to maintain momentum coming out of your planning session and improve follow-through.

About Mark Moses

Mark Moses is the Founding Partner of CEO Coaching International and the Amazon Bestselling author of Make Big Happen. 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 600 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 59% during their time as a client, more than five times the national average. For more information, please visit:

The post Part 2: Execute An Annual Planning Session That Will Set You Up For Success in 2021 appeared first on CEO Coaching International.

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