A typical EOS® Annual Planning session is two full days when facilitated by a Professional or Certified Implementer. That extended format isn’t arbitrary – it gives teams the space to deepen trust, strengthen team health, surface relational dynamics, and work through issues with the kind of candor that’s hard to generate on your own.
If you’re not working with a facilitator, you may not need the full two-day container. A focused one-day annual planning session can work if you follow a clear structure and keep the conversation honest. Below is a proven agenda you can run internally with your leadership team.
1. Review the Prior Year
Start with perspective. Have each team member individually reflect and share:
What were the major wins?
What challenges did we face, and how did we overcome them?
What did we learn?
Then review the measurable elements:
Revenue and profit targets vs. actuals
Your previous year’s goals and how many were completed
Each person assigns the year a letter grade
This isn’t an exercise in nostalgia; it’s a live conversation about alignment and learning. Make the discussion real, lively, and reflective.
2. Review the Previous Quarter
Apply the same lens at a smaller scale:
How many of our rocks did we complete?
Did we hit our numbers (revenue / profit)?
What worked? What didn’t?
What did we learn?
Close the loop on the past so the team can focus fully on the future.
3. Review and Update Your Vision/Traction Organizer (V/TO)
Now turn the page.
Walk through the VTO line by line and ensure the team remains aligned on your core vision. Make updates where needed. This includes rewriting your Three-Year Picture, pushing it out another year.
The VTO should feel true, not aspirational wallpaper. Debate until it does.
If you don’t have a V/TO complete, you can review a tutorial on how to create one here.
4. Conduct a SWOT Analysis
Work through Strengths, Weaknesses, Opportunities and Threats
This is not just an intellectual exercise—it expands the team’s thinking and primes the system for the next step: identifying real issues.
5. Complete the Organizational Checkup
Do the EOS Organizational Checkup as a team. This will highlight structural gaps in your execution system and give you a sense of how close you are to the EOS benchmark of “80% strong” in the Six Key Components.
This step often reveals issues that haven’t been named explicitly.
Find the organizational checkup here.
6. Build a Comprehensive Issues List
Combine insights from:
The SWOT
The Organizational Checkup
Any lingering or emerging team concerns
Not everything from the SWOT will be an “issue.” That’s fine. The goal is to create a true list of what stands between you and your vision—organizational, strategic, or relational.
7. Create Your One-Year Plan
Now shift from diagnostics to commitment.
Ask each team member to privately write down what they believe are the three to seven most important priorities for the coming year. These should be big, outcome-level goals, not 90-day projects.
Then go around the room one at a time:
Share one priority
Discuss
Decide if it belongs on the final list
Keep it, refine it, or remove it
Move to the next
Aim for three to seven goals. Remember: more is not better.
Define your revenue and profit target for the year and sanity-check that it aligns with your Three-Year Picture.
8. Set Your Quarterly Rocks
Using your One-Year Plan as the guidepost, determine the company rocks for the next quarter. These are the concrete steps or milestones needed to move meaningfully toward your annual goals – or to address the most urgent issues facing the business.
Again: three to seven company rocks is the sweet spot.
After that, each leader selects their own three to seven individual rocks, including any company rocks that were assigned to them.
Set revenue and profit targets for the upcoming quarter as well.
9. Clean Up and Prioritize the Issues List
End by reviewing the full issues list:
Which issues have been resolved through your goals or rocks?
Which need attention this quarter?
Which should be pushed to the long-term issues list?
This clean-up step ensures you’re not dragging noise into your next Quarterly Session.
A Tool to Help You Run the Entire Process
If you want structure, clarity, and a place to store all of this thinking, ninety.io is an excellent tool. It handles your VTO, issues list, rocks, scorecards, agendas, and quarterly/annual planning workflow—making it much easier to run this entire process without dropping threads or losing momentum. For teams running EOS internally, it keeps everything organized, visible, and accountable. Try a free 30-day trial of ninety.io to manage your EOS process and material.
For 13 years, Jeremy led an award-winning creative agency that worked with Canada‘s top companies on digital design projects, giving him unique insight into the challenges that driving innovation can place on teams. Later, he co-led a consumer products business with his wife that grew from their living room into a multi-million dollar brand sold through major retailers across North America.
In both those businesses, The Entrepreneurial Operating System (EOS) played an essential role in Jeremy’s success. He began sharing EOS in his work as an author and mentor to other entrepreneurs and today, Jeremy brings this transformational knowledge to growth-oriented leaders and their teams in his role as a Professional EOS implementer®.
