Quick Reference:
Strategic planning ≠ Annual planning. Strategic is your big picture company vision; annual planning is the roadmap to get you there.
Preparing for your Annual Planning meeting is critical, and it's going to take more time and effort than running the meeting itself.
Everyone should be participating in the Annual Planning meeting. Whether its in break out sessions, surveys, or sharing ideas, make sure your whole team feels like they've contributed.
Once the meeting is over, follow up with participants immediately. This illustrates that you're moving forward with action items from the meeting, and shows that attendees' time was well utilized.
To absolutely no one’s surprise, we love a good plan. Our team knows from experience that it’s not enough to have ideas and half-baked visions for your company; to execute that vision and make it a reality, you need actionable steps and milestones. And we can’t think of a better time to talk about planning than right now, when so many companies are wrapping up projects and setting their sights on the new year.
Hosting an Annual Planning session for your team is our number one recommendation for any company looking to grow, streamline, or pivot in the new year. And in case you haven’t noticed, just about every company is looking to do one of those.
We are huge advocates for Annual Planning sessions because we’ve tried them ourselves. In fact, our team meets on a quarterly and annual basis to look back on where we’ve been, take stock of our current state, and create a strategy to move forward in alignment with our goals and values.
Take our word for it: Annual Planning is the best way to usher your team into the new year with clarity, intention, and energy for the changes ahead.
While the new year is almost upon us, there’s still time to focus on annual planning. To help you host an Annual Planning session (or at minimum, block off an afternoon to do some big picture planning with your key team), we’ve outlined our Annual Planning framework, including best practices and our favorite tools, below. If you’d like to see how these pieces work together, check out our Annual Planning Webinar video, hosted by our Founder Molly Yanus, from Q3 of 2022!
Strategic Planning vs Annual Planning
Before we share our recommendations for annual planning, let’s distinguish it from strategic planning. Both Annual Planning and Strategic Planning are essential processes for clarifying and executing long term direction and success of your business. But they are separate and unique approaches that work together for the betterment of your growth.
Strategic Planning
Strategic Planning meetings happen every 3-5 years, and dictate the long term trajectory and vision of a business. In a Strategic Planning session, your key stakeholders will discuss the company vision for the future and long term goals.
There are a few questions that you can ask yourself to adequately prepare for your meeting: you want to be in the next 3-5 years. In the years between strategic planning sessions, your team should update the strategic plan as needed – adjusting it to changes in your company or industry – but for the most part this is a guiding framework from which all decisions should be made.
Think of this as your company’s North Star. It’s always present, it’s pretty consistent, and it helps you orient as you move forward.
Annual Planning
Annual Planning helps you execute the company vision. In an Annual Planning session your team should check in about the company goals and trajectory, and then create a tactical roadmap to meet your objectives.
There’s a key difference here in terms of scope: Annual Planning happens on a budget or fiscal year cycle. With a clear start and end date, companies can use Annual Planning sessions to make sure goals and expectations are realistic, hold themselves accountable for making progress, and then reevaluate on an annual basis.
Annual Planning Meeting should dedicate some time to reflecting on the prior year’s objectives and evaluating progress and success related to those goals. Once those parameters are clear, Annual Planning sessions can be used to focus on how to improve in the year to come.
If your Strategic Plan is a North Star in your journey, Annual Planning is the map in your hand. You use it to determine how to get to the next milestone, and check in with it regularly. It’s your day-to-day resource for navigation.
Planning to Plan: Preparing for Your Annual Planning Meeting
It might sound surprising, but we've consistently found that preparing for the Annual Planning Meeting takes significantly more time and energy than holding the meeting itself. Why so much time spent in planning to plan? Being prepared ensures that you'll make the most of the meeting, and that your team feels like their time was well utilized.
We can't stress the importance of this enough. Whether you’re hosting your meeting in person or virtually, most teams will need to set aside their regular routines and projects to attend. To make the time count, be prepared and make sure everyone is ready to show up, engage, and dive in to the meeting content. Especially those who are presenting or facilitating.
When we prepare for an Annual Planning Meeting, we ask a few simple questions:
Why are we doing it?
The specific value of an Annual Planning Meeting will be unique to your team and organization. But in general, Annual Planning sessions are crucial opportunities to realign with your strategic goals, pivot when appropriate, and course correct in regard to missed opportunities or big company changes.
Annual Planning sessions also allow teams to be proactive about the year ahead. Rather than waiting until they arrive, you can use Annual Planning meetings to address risks, threats, and opportunities before they happen.
While the majority of your time in an Annual Planning meeting should be spent looking ahead, don’t miss out on the chance to look back at the previous year. This is a great opportunity for teams to identify lessons learned from the past year, understand how they got to where they are today, and then let those findings inform your strategy moving forward.
Ultimately, the why behind Annual Planning is to get clarity and direction. Use it as a time to understand where you came from, where you are now, and where you’re headed. And then, you and your team can make a plan for how to get where you want to go.
What do we cover?
A common misconception is that Annual Planning is all about budgeting. Budgeting is definitely going to be part of the conversation, but it’s not the whole purpose of the meeting. There’s a tactical component of planning, a strategic component, and of course, there’s logistics to explore.
In fact, we think that the Annual Planning Meeting is the perfect time to have different teams and departments come together and collaborate on the next year’s plan. This helps prevent teams from becoming isolated, and brings continuity to work across the company.
Who should be included?
As much as possible, we believe that everyone should be included in annual planning – but not necessarily in the same way. Every organization or company has different levels of leadership, different roles, and different ways of connecting teams together.
We recommend having a team or individual that is responsible for planning and steering the meeting itself, and then having additional groups who contribute information and ideas to the meeting.
For example, have an Annual Planning committee that handles the logistics, agenda, and follow-up from the meeting. But for the content of the meeting and sharing of ideas, pull in as many different team members and managers as possible. The goal in your annual planning should be to get teams and departments collaborating on a common direction in the new year, rather than simply sharing their information from the past year.
The bottom line is that for the annual plan to be put into practice, everyone should feel like they have contributed and are clear about conclusions and action steps from the Annual Planning meeting.
Where should we host it?
We advocate for in person meetings whenever possible, especially if your team is remote. Try meeting in a space outside the regular office, and dedicate some of your annual meeting time to being screen-free so that your team can connect, consider, and think big for the year ahead.
With so many teams (ours included) being remote these days, a virtual Annual Planning meeting can be a great option. There are loads of virtual collaboration tools (our current favorite is Miro) that help make remote meetings feel integrated and productive.
No matter where you’re hosting your meeting, take the time to consider the logistics of the meeting and your team’s experience. If the meeting is in person, consider the room setup, plans for travel and breaks, budgeting for lunch, etc. It’s especially important to have all the logistics of the meeting ironed out ahead of time if you’re asking folks to travel; you want to make the most of your time and theirs.
There are similar considerations for a virtual meeting, with an emphasis on tech. Will you need breakout rooms? Is the whole team familiar with the tools that you’ll be using? Is there a dedicated representative to help support with any technical issues? Answering these questions ahead of time can avoid time and energy wasted in navigating technical issues, and help keep the team engaged throughout the meeting.
When should it happen?
We usually recommend that Annual Planning Meetings happen at the start of the quarter before the new fiscal year. So for companies whose fiscal year begins on January 1st, an ideal time for an Annual Planning meeting would be in October.
That being said, we are firm believers that it’s never too late to have your Annual Planning Meeting. If you’re approaching the start of the new fiscal year, try carving out an afternoon or a day on your calendar to connect with your team about what lies ahead. Even a little bit of forethought and stepping out of daily operations can do wonders to usher your company into the new year with clarity and energy.
Diving In: Our Approach to Effective Annual Meetings
Once you've gotten all of the planning out of the way, the meeting becomes the fun part. This is where you get to connect with your team, rehash the biggest lessons from the previous year, dream a little about where you want to go, and start making a plan of action. As they say, this is where the magic happens.
When we facilitate an Annual Planning Meeting, we like to take a chronological approach. We start with where we’re coming from, taking time to conduct a retrospective with participants and discuss lessons learned.
Then we check in with the present moment. Current trends, outstanding projects, statistics and surveys – these are all great data points to collect. But there’s also the less measurable information that’s just as important, such as things that are bringing the team joy, or draining the team’s energy. We also explore what feels like it's blocking us and getting in the way of meeting our objectives. Finally, we reaffirm our mission, values, and vision for the future.
Once we know where we are, we can start to look ahead. We discuss team aspirations, company vision, growth trajectory of the business, and what it would mean to the team to be successful by the end of the next year.
It’s important to note that Annual Planning Meetings are designed to be idea generators, and many of those ideas won't go into effect on January 1st. So in addition to thinking big, we encourage any team in an Annual Planning Meeting to consider the scope of their goals. Is your goal going to come to fruition in a month? Six months? Will it take the whole year? Setting expectations on goals helps to turn them into reality.
After the Meeting
Once the meeting is over, we highly recommend immediate follow up with all who participated. It’s likely that your meeting generated some ideas, some action items, and brought about concerns or changes that need to be addressed. While it might be tempting to wait until some of those changes happen before you circle back with attendees, we’ve found that immediate follow up produces better lasting results.
In your follow-up communications, you don’t have to have all the answers or have solved all the obstacles that were brought to light. But you can begin to set expectations for when people will hear from you about changes to be made, and when you might need to hear from them. This is also a great time to send out a post-meeting survey to collect feedback and insights, since the meeting will still be fresh in everyone’s mind.
One of the greatest benefits of immediate follow up is that it illustrates to your team that their time and energy wasn’t wasted. So many big picture planning meetings end up becoming a place to share ideas, and then those ideas sit on the shelf for the rest of the year. Connecting with attendees right away with clear communication and a plan for moving forward shows that ideas were taken seriously, real change is coming, and gives everyone who attended a sense that their contributions are being utilized.
When it comes to setting your business or organization for success in the new year, an Annual Planning session is the best place to start. If you're looking to host an Annual Planning session and want some facilitation, reach out to our team!
For a full breakdown on the benefits of Annual Planning, check out our Annual Planning Webinar recording with Founder Molly Yanus.
Quick Reference:
Strategic planning ≠ Annual planning. Strategic is your big picture company vision; annual planning is the roadmap to get you there.
Preparing for your Annual Planning meeting is critical, and it's going to take more time and effort than running the meeting itself.
Everyone should be participating in the Annual Planning meeting. Whether its in break out sessions, surveys, or sharing ideas, make sure your whole team feels like they've contributed.
Once the meeting is over, follow up with participants immediately. This illustrates that you're moving forward with action items from the meeting, and shows that attendees' time was well utilized.