A Checklist for Your Next Annual Planning Meeting (FREE Download)

When holding your annual planning meeting, it is critical to conduct the event in a location that provides few distractions. You want attendees focusing on the important details of planning your business and not having their attention divided by their normal, day-to-day routine of checking text messages, sending “quick” responses and other similar activities that may be critical to getting things done, but are not conducive to the future-planning process. 

So when it comes to planning the fine details for your annual meeting, you should exert the same focus you expect of attendees. Leaving the details of planning the meeting to the last minute can result in an unfocused event that doesn’t tap into the high-level participation you require. 

Below we’ve prepared a checklist for your annual planning meeting, but also a few strategies to consider when organizing the meeting’s finer details. 

How to Approach Your Annual Planning Meeting 

Real-Time Situational Awareness: Your annual meeting is a collaborative affair,  calling upon your CEO, your leadership team and a strategic coach to show up, be present and be at the top of their respective games. With all the changes and uncertainty in the world today, your leadership team is a critical link between your business and its customers, so be ready to provide them with the correct tools that will lead to strategic thinking and execution planning–and have them do the same.

Repeatable Growth Process: Preparing your team for a high-success meeting can also lay the groundwork for future meetings. High-growth companies can either create a lot of politics or build a repeatable growth process. We strongly recommend focusing on the latter.

Fun Process: Despite the critical importance of your annual planning meeting, it shouldn’t be a high-stress affair. It should be a fun event that allows your team to relax and showcase their best selves, without being on the defensive. Allow your team the breathing room to provide critical insights that can lead to future growth. A fun meeting also allows you to better see your leadership team’s “true selves.” which can provide key insights into which leaders are in the right roles for the next level of the company’s growth. This is an important insight, both for your team’s future happiness and also for the success of the company.

Planning Checklist

Timeline:

Two months (or more) before the meeting.

Tasks: Select your annual planning location and finalize your dates.  

• Find a location that is inspiring, fits your culture and will allow you team to focus on the PLANNING of your business and not on the day-to-day details of working on the business

Related content: Why we recommend planning your annual off-sites a year in advance.

One month prior

Tasks: Select your growth coach.

• Ensure there’s a good cultural and personal fit between your growth coach and your CEO.

Related content: Learn more about PFD Group’s coaching strategies | Why do I Need a Strategic Coach?

Five weeks prior

Tasks: Finalize and distribute a preparation survey to your leadership team.

• Give your team one week to complete the survey. The survey should be mandatory for participants and also require input from their direct reports.

Three weeks prior

Tasks: Based on survey input, finalize a high-level offsite agenda and team activities. 

• Plan a general flow of exercises focused on three areas: Trust and culture; understanding changing customer needs to refine your unique and valuable strategy; and build a clear team and individual execution plan for the coming quarter and year.

Two weeks prior

Tasks: Confirm catering, finalize the event schedule and book any remaining travel that needs to be confirmed.

• For the best value, book air travel no earlier than 45 days prior to travel and no later than three weeks before departure. After that, the airline recognizes the “urgency” of your travel needs and fares go up accordingly.

Related content: What goes into planning an event with purpose?

One week prior

Task: Send out final preparation questions and aggregated survey results to all participants.

• Survey answers should be fully shared, but in a way that preserves the anonymity of  respondents. Transparency helps drive trust and anonymity encourages more honest feedback. Both support the team in focusing their offsite time on the questions that will create the greatest value.

One day prior

Task: Coaching team arrives to complete the set up.

Night before

Task: Welcome dinner.

• A welcome dinner, if possible, is highly recommended. Here you can celebrate the wins of the previous quarter and recognize your core value award winners, while also kicking off your strategy meeting on a celebratory note.

Related content: Who Should Attend Your Annual Strategic Planning Meeting?

Annual Planning - Day 1

Focus: Culture, strategy and team bonding activity.

• The first day is key. It needs to clarify and reinforce your team culture, trust, unique and valuable strategic direction along with time for the team to connect outside of the meeting room.

  Related content: Vision Boarding: Creating Your Future and Your Personal Why

Annual Planning - Day 2

Execution.

• Your meeting agenda should establish clear team and individual priorities and guide the meeting to capture key communication takeaways for the entire company. You should also finalize the quarterly offsite dates for the next four quarters. Remind your full leadership team that these meetings require mandatory attendance while also providing them with enough time to set these dates in stone.

  Related content: Creating Quarterly Themes to Strengthen Team Morale

The next weekly leadership team meeting

Tasks: Share the key takeaways from the meeting; follow up by sending these takeaways to the entire team. Ensure all individual priorities are included in the software you use to run your business.

• We recommend Metronome Growth Systems. Metronome software is optimized so you can work ON your business, and not spend time working on customizing off-the-shelf project management tools to meet your business needs.

  Related content: Who Should Attend Your Annual Strategic Planning Meeting?
  
  

2023 Cultural and Growth Foundation: Why Plan Your Strategic Offsites A Year in Advance?

In the aviation industry, it can be disconcerting for a novice passenger to watch the pilot walking around and checking the condition of the plane. Seasoned travelers, however, know the pre-flight check is a mandatory part of every air journey, whether the pilot is helming a small private aircraft or the massive 787 Dreamliner. 

It may seem redundant for the pilot to check everything that the ground crew also recently checked, but in fact, it is a testimony to the great care the pilot has for the passengers–that he or she will leave nothing to chance. 

Executive Responsibility

The same can be said for planning for the success of your business. While your crew should be highly skilled, you as CEO still take final responsibility for successfully moving your business from one place to another. 

As the CEO, your culture and your team are your growth foundation. You want your entire leadership team to be experts in your market and customers. That is best done in person.

With more people working remotely or in hybrid settings, company offsite meetings are the perfect opportunity to bring your leadership team together to bond, strengthen company culture, and talk about high-level strategies that may get neglected when your team dives into the day-to-day tasks that need to be done.

These regularly held strategic meetings are where CEOs can give and receive the key feedback to keep the proverbial planes running on schedule. 

Develop a Regular Cadence

If you’re a frequent business traveler, you know the exact times your preferred airline departs. In fact, you rely upon the airline and the airport to keep things running smoothly. And when flights start to back up, chaos ensues. 

You don’t need news headlines blaming everything from weather to supply chain shortages to ground grew sickouts to know that delays and cancellations are not good for business. The same is true for your strategic planning meetings. 

Put the meetings on the books at least a year in advance. Make sure everyone knows when and where they will occur and give everyone plenty of time to prepare for the meeting. And keep to the schedule as if you expect the New York Times to blast you for any cancellations or changes that may occur. 

Quarterly Meetings

We recommend holding your high-level strategic meetings once per quarter, either at the beginning of the quarter as a way to codify your plans for the coming 13 weeks, or waiting until the end of the quarter after your numbers drop as a way of wrapping up and reviewing the previous period. 

We find the CEOs we work with are equally divided in their preferences with respect to which schedule is best. 

Another timing consideration–hold your quarterly strategic meetings two weeks before your scheduled board meetings. This gives your senior leadership the opportunity to come together to measure and future-plan your corporate strategy. How have things progressed as planned since the last meeting? What will you be measuring at the next strategic meeting? How will you report on these metrics at your upcoming board meeting? 

Beyond reporting back to your board, holding quarterly strategic meetings gives your A-Players the opportunity to build routine feedback loops. They become more accountable to one another and they also establish the ideal foundation to review and present high-level strategies to their entire team back at the office. 

Modern Day Water Cooler

If you’re of a certain age, you remember the idea of the water cooler chat. People would supposedly gather around the water dispenser to chat about work activities and to catch up on gossip. Whether or not that was ever a real office ritual, the idea behind it was sound. 

“We exist to connect with other human beings”

–Jen Fisher, Chief Well-Being Officer, Deloitte US (via Salesforce.com)

People enjoy the social interaction of working together. And a lot of that has been lost as more companies are going hybrid or fully remote.

Your strategic planning meetings give your executive team the opportunity to reconnect on a personal level. Not only do they get to discuss strategy in person, they learn a lot in the little side discussions that may be largely missing on Zoom as people worry that maybe their side chats are being monitored. 

The offsite meeting provides a forum for getting to know colleagues on a personal level. The side events, the dinners, and the random hallway conversations with colleagues all lead to building deeper connections that are more difficult to establish in an office environment.

Event Format 

The format of the meeting–whether you choose to hold it in a high-end hotel setting or a more casual retreat site–should match your corporate culture. CEOs differ on their preferences and there is no “right” way to plan the format. 

If you absolutely can’t get to an off-site location, a virtual meeting will work. But whenever possible, plan for an in-person format. 

And whether you’re holding the meeting in person or virtual, be sure you leave enough time for personal interaction and reflection.

We also highly recommend using a coach to facilitate your meeting. Coaches can help keep your meeting running on time, making sure you hit all the high points, which leaves more time for you as CEO to join the discussions and require you to watch the clock less as you look to ensure everything happens as you’ve planned it. 

Great coaches book out early, however, which is another key reason to schedule your off-site meetings as early as possible. 

If you’re looking for more ideas on implementing a successful strategic meeting, PFD Group can help. Contact us now for more information, or read about the PFD Stewardship Summit in Alaska. 

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Who should attend your annual strategic meetings