Part I: Preparing an Effective Annual Planning Session During the Pandemic

Chief Executive Officer

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One of the biggest differentiators between companies that stay small and companies that get BIG is effective annual planning. This year, planning could also be what separates companies that emerge from the pandemic and succeed in 2021 from those that remain stalled in the past.

Typically, annual planning sessions are all about alignment. You and your leadership team set top goals for the next 12 months, and then break those goals down into actionable steps that sync together and generate progress day by day, week by week, quarter by quarter.

At this year’s session, you’e also going to have to realign your workforce with your company, and with each other. Your people are struggling to establish work-life boundaries as they adjust to WFH. They’re feeling isolated from the camaraderie and culture that animates maximum effort and innovation. Depending on your business, they might still be fretting about job security.

In short, your people need to see a clear path forward and they need to feel like you’re all taking that journey together.

The more prepared you and your C-suite are going into the meeting, the more productive and effective the meeting will be. These are the three steps we help our entrepreneur coaching clients move through as they prepare their annual plan to make BIG happen.

1. Think BIG again.

In any business environment, the single most important question a CEO can ask is: “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?

[Download our Crystal Ball Exercise here.]

Mark Moses: A Covid-19 vaccine isn’t going to cure your narrow supply chain, stagnant customer base, or mediocre digital marketing. Effective annual planning will.

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, but it’s even more important as you prepare for 2021. All the crisis management and pivoting you’ve done in response to the pandemic, all the tough decisions you’ve made, all the Zoom calls and late nights at your desk — all that effort has sustained your company so that you can start a brand new chapter, right now. In 2020, you had to narrow your focus to the small stuff. Your 2021 has to be about seeing the BIG picture again.

Give yourself some time and space to separate yourself from a transition mindset. Get back to being the visionary that your company needs you to be. See a new version of your company that inspires you, and you’ll be able to inspire your team to make that vision real next year.

2. Assign prework to your key leaders.

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 your 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.

Make sure you let your leadership team know that you don’t want the pandemic to dominate these answers. Yes, ensuring the safety of your team and your customers is going to be a major factor for the next 12-24 months. Yes, you’ll have to fire some bullets in Q1 and follow the ones that hit their targets as you fine-tune your digital pivot.

But the companies that suffered the most this year had underlying problems that Covid-19 revealed rather than caused. A vaccine isn’t going to cure your narrow supply chain, stagnant customer base, or mediocre digital marketing. Effective annual planning will.

3. Hire a facilitator.

Even under normal circumstances, a CEO facilitating his own planing session is a bad idea. When the CEO facilitates, other leaders often consciously or subconsciously feel compelled to agree with the boss. Participants who are further down the chain will be less inclined to voice their honest opinions, which limits the free-flowing exchange of ideas and feedback you need for a successful session. Facilitating also forces the CEO to constantly switch back and forth between being the organizer and being a meaningful participant, to the detriment of both responsibilities.

Again, that’s what can go wrong at a typical planning session. Now, think about how atypical this year’s event will be!

As much as your Zoom skills have improved, running this meeting online or in a socially distanced environment is going to be a BIG challenge. Setting aside the technical hurdles, your employees are already experiencing some degree of Zoom fatigue. Seeing you on their screens talking about the business will make this feel like a longer version of one of your daily or weekly check-ins. Your planning session is supposed to feel different: more interactive, more urgent, more important.

When the CEO is a full participant in the planning session, it sends 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.” That’s why hiring a 3rd party like one of the coaches at CEO Coaching International to facilitate your annual planning session is always a best practice.

The coaches at CEO Coaching International are experts at running these meetings, online or IRL. 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 whether you’re meeting online or in person.

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. 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:

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