How to Conduct an Annual Planning Meeting

Don’t Start the Year Without a Plan

You wouldn’t spend money on a plane ticket without knowing the destination—so don’t budget for a new year of business without having a strategic execution plan!

Hold an annual planning meeting to create a focused, detailed roadmap of what your company needs to accomplish and how you will get there. This is your chance to step away from the day-to-day hustle and bustle of your business. It’s an intentional, focused moment to reflect on your learnings from the previous year and allow those to shape your future decisions. It’s also a time to identify opportunities and threats, use data to understand the company’s progress and trajectory, and craft high-impact priorities for the fiscal year ahead.

Sounds great, you may be thinking—but where do I even start? A lot of CEOs, even those with years of experience, have never conducted a formal annual planning meeting. There’s so much to cover that the sheer volume of content can feel overwhelming. 

If you find yourself in the same situation, use this guide as your launching pad. It will help you prepare for, conduct, and wrap up your annual planning meeting. Using this tried-and-true approach, you can do more than simply write a plan—you can help your team get aligned on the company’s top priorities, understand who is accountable for which pieces, and prepare for any challenges that may arise in the upcoming year.  

This Guide Will Help You…

• Understand just how important it is to follow a structured annual plan process.
• Learn how to set an annual planning meeting agenda that highlights key discussion points.
• Implement techniques to promote vibrant teamwork and thoughtful strategic decisions.
• Understand how to write actionable goals and specific success criteria. 
• Create an annual plan that supports your long-term strategy. 

Preparing for Your Annual Planning Session

Set the Stage

If your team doesn’t have a lot of experience with annual planning, they may not understand just how essential this meeting is. Pulling team leaders away from their daily activities is expensive, and if they don’t recognize the value, they may feel confused or even resentful. This is not productive energy to bring into a planning session. 

As Simon Sinek tells us, “Start with why.” Thoughtfully define the purpose and objectives of the meeting, and share these with your team. This session calls for their full and enthusiastic participation, and knowing the “why” will help increase buy-in.  

Writing a purpose statement is not the only thing you should do to help your team prepare. Get good ideas flowing before the meeting by assigning a simple prework exercise 1-2 weeks in advance. Consider using a Start-Stop Keep exercise—what initiatives or projects should the company tackle in the new year, what detrimental activities should the company put an end to, and what is working well that the company should continue? By having time to think about these questions in advance, your team members will come to the session ready to share their insights and ideas. 

Develop an Agenda

Don’t neglect writing an agenda. Even the most engaged teams can fall down rabbit holes. Without an agenda to anchor you, you risk letting all your valuable time slip away without ever producing a real plan. 

As you craft your agenda, focus on a few key items: 

• Topics needing discussion (team or organizational changes, large initiatives, cultural adjustments, etc.)
• A review of the previous year, including (but not limited to) financial data
• A SWOT (Strengths, Weaknesses, Opportunities, Threats) analysis
• A review of the prep work (this may be the Start Stop Keep exercise)
• Setting goals for the upcoming year 
• Developing a detailed action plan

Define time limits for each of these areas to help you stay on track and balance your time. Although goal-setting logically fits near the end of the agenda, it can be squeezed out by prior items—so make sure to abide by your schedule.  

If you end up with topics that need further discussion but aren’t urgent, put them in a Parking Lot and revisit them during a future meeting. 

Prepare Data in Advance

Data will be a crucial part of your discussion, especially as you check in on your company’s progress. This information will set the foundation for informed decision-making during the meeting. 

Nothing slows a planning meeting down like pausing to dig up data. Make sure the right team members come prepared with key data points, like the previous year’s financial performance, market trends, and team health metrics. Make this request 1-2 weeks in advance so that they have time to prepare. 

Conducting the Meeting

Topics Needing Discussion

Your company may be undergoing or anticipating a major change or challenge. At the beginning of the meeting, reserve a few minutes to provide updates and answer questions about this topic. This discussion will undoubtedly influence how the team approaches building the new plan. 

Reflect on the Previous Year

You shouldn’t plan for the future without keeping the past in mind—so don’t miss out on reflecting on the previous year’s wins and challenges. Use these questions to guide your discussion:

• What bright spots did we have, and how did we get there? 
• What caused certain projects to fail or targets to be missed? 
• What should we do differently in the year ahead?

Allow your team to discuss learnings and improvement areas. During this conversation, designate a note-taker to capture key points so that you can reference these later. 

Perform a SWOT Analysis

Next, conduct a SWOT analysis. List out the business’s strengths, weaknesses, opportunities, and threats. This is how to think about SWOT:

• Strengths: Characteristics of the business or project that give it an advantage over others
• Weaknesses: Characteristics that place the team at a disadvantage relative to others
• Opportunities: Elements that the project could exploit to its advantage
• Threats: Elements in the environment that could cause trouble for the business or project

This exercise will help the team gain a sense of what is most important to focus on when it comes to projects and metrics in the year ahead. A SWOT analysis can also be uplifting to team morale. Even though you’re recognizing improvement areas, you’re also recognizing your assets, along with potentially exciting opportunities!

Review the Prep Work

A couple of weeks before the session, you should have sent out a prep work exercise to help your team brainstorm constructive ideas for the coming year. Display the thoughts they have recorded, and give each team member a few minutes to speak about their ideas. During this discussion, you as the company leader should go last to avoid influencing the team and missing out on a potentially great idea. 

If any idea has the potential to be a strong strategic priority for the year ahead, convert it into a rough draft for a new goal (if you’re using the Rhythm software, you will be able to do this easily!). 

Set Your Annual Goals

Finally, take time to determine 3-5 high-impact priorities for the year ahead. Sure, your team has many great ideas! But if you commit to too many goals, you risk not being able to deliver on one or multiple. As you craft these priorities, continually reference the company’s vision and 3-5 year strategic objectives; everything you’re planning to do in the coming year should directly support your long-term journey.  

Next, review the KPIs (key performance indicators) that you have been tracking. Are they giving you enough visibility into the company’s progress and performance? Are any of them redundant? Make sure that you have leading indicators—metrics that will help you predict potential failures—in your list of KPIs.

Remember—write your goals to be SMART: specific, measurable, achievable, relevant, and time-bound. Work with your team to establish success criteria; what do success and failure look like for each of these goals? Invite questions, discussions, and even disagreements—it’s better to get these out of the way now rather than run into confusion halfway through the quarter. Be precise so that everyone is on the same page about what needs to be accomplished. 

Develop a Detailed Action Plan

This is where many teams falter: They have a high-level vision established, but they don’t take the time to translate it into digestible action steps. The “what” is there, but the “how” is missing. This inevitably leads to confusion, execution gaps, and delayed delivery. No matter how great your goals are, you simply won’t reach them without an execution plan. 

Break down your annual goals into quarterly milestones, keeping in mind that some details may shift during the year. Focus most on the immediate quarter, Q1, and establish quarter priorities that support your annual priorities. You may have a rough idea of what your Q2, Q3, and Q4 priorities will look like, but no need to finalize those now. Keep the plan dynamic.

For each Q1 goal, assign an owner. Even though most of these projects will likely be collaborative, you need to identify the one person ultimately responsible for the goal’s delivery. This person will be accountable for moving the goal forward and reporting on its process. For each goal, you should also set start and end dates that consider dependencies, as well as success criteria. Then, ask each goal owner to list out Tasks (to-do list items) to ensure steady weekly execution. They may need to assign some of these tasks to their direct reports or others on the leadership team.