Yes, meetings kinda suck. Especially ones that last one or even two days. However, when done well and right, they can be the difference between another year of learning vs a year of winning.
I started coaching a team this last year who is building a great company and has a solid base for scaling culture. They were aware enough to see “ceilings” coming. So when we began our work, they had recently completed their annual planning (not using EOS®). I requested all their outputs or artifacts from the meeting so that I could find alignment with the EOS framework.
What was then shared was a combination of pictures of whiteboards, large Post-it notes, some spreadsheet items, and slides. Many of the elements were solid, but Annual Planning isn’t just the meeting and related outputs; it is the ability to activate the work via an approach like Meeting Pulse and the 90-Day World®.
Within the EOS framework, Annual Planning is not just a calendar event; it’s a strategic checkpoint. It’s an opportunity to build team health, reset the Vision, and create a clear plan for the next year.
If you skip it, or just “half-day” it, you run the risk of losing traction as early as Q1. I’ve seen it happen. The calendar turns, the whirlwind resumes, and goals wither on the whiteboard.
However, with a well-run EOS® Annual Planning Meeting, you shift from reacting to taking intentional action. You stop spinning and start steering.
“Before running an annual planning session on EOS powered by Ninety, I would get anxious about the investment in time and money. Now I get anxious if anyone discusses potentially not doing it.”
CEO/Integrator™ at FIT Technologies
How to Prepare for the EOS Annual Planning Meeting
Prework is not optional. Come into the room unprepared, and you’re burning the most expensive cost on your P&L (leadership time) without a return. Here is the essential prework you should complete before beginning your Annual Planning Meeting:
Facilitators should:
- Send the EOS Org Check-up or Ninety’s integrated Org Assessment – Remind the team to complete it honestly — this isn’t about grading, it’s about identifying opportunities to strengthen the Six Key Components®.
- Decide on the Team Health Exercise – Select and prepare a structured exercise to strengthen trust and connection during Day 1 (e.g., Personal Histories, The Five Dysfunctions of a Team and One Thing exercise).
- Ensure Data Is Current – Update the Scorecard, financials, and key measurables in Ninety to have a simple Year-in-Review summary.
Every Team Member should:
- Complete EOS Org Check-up or Org Assessment within Ninety to benchmark health.
- Review Issues & Rocks – Add any additional issues (along with potential Rocks) that should be there for the meeting.
- Schedule a Clarity Break to Reflect on the Year Past and Year Ahead – What worked? What didn’t? What should we learn or adjust? Bring this perspective to the Check In and Year-in-Review discussions. And reflect on where we’re headed: What does success look like in 1 year? 3 years? 10 years? Bring ideas that might inform updates to the V/TO® or the 1-Year Plan.
Leadership alignment starts before you even walk into the room. Everyone should have a point of view, but we don’t want to spend hours “getting on the same page” in the moment.
Objective Driven, not Agenda Driven, to Win: EOS® Annual Planning
I am competitive. Almost every entrepreneurial leader I know is as well. If we weren’t, then we would probably be doing something else. Therefore, we need a long-term game plan for the year we are about to enter. This is not a sports analogy; it's a growth approach.
I’ve coached more than 400 session days, and I’ll tell you flat out: one planning day won’t cut it. You need two full days away from the noise. Gino calls it “getting out of the whirlwind.” EOS calls it the Annual Planning session. I call it the most valuable time your leadership team can spend in order to win.
Here’s how to run it the way it was intended to achieve Traction©:
Day 1: Look Back and Look Up
1. Start with a Segue—Not Small Talk
Every team member shares:
- Three business greats from the past year
- One unexpected business great
- One personal great
- What they expect to get from this two-day session
Every business is a people business. Therefore, we need a moment to remind ourselves of the trials and tribulations of what got us here and hopefully to celebrate or learn. We are about to do hard work and the better we connect through empathy and compassion, the deeper we can go. I believe in Agreement-Based Leadership. Too often, people have expectations without agreements. It is critical that we are aligned on objectives and outcomes before we begin. My last coaching as we move beyond the Segue is “please own your experience and don’t wait until the end to say something you observed that could be better. See it, feel it, say it.”
2. Review the Year: Data, Goals, Rocks
Pull up the numbers. Revenue. Profit. Leading indicators. And last year’s Rocks. We’re not here to spin. It’s time for straight talk.
Did we hit the targets? Where did we come up short? What can we learn from it?
This is where many teams try to sugarcoat. Don’t. You don’t build great companies without being real.
3. Team Health First
Your company’s ceiling is your team’s ceiling. We use this time to run team health exercises that deepen trust and spark honest conversation. We start off with something simple, like a personal history exercise, and then move to Patrick Lencioni’s Five Dysfunctions, which I first started using in 2005, and then go deep with an exercise such as The One Thing. This progression sometimes evokes laughter or tears but always connection.
4. Run the EOS Org Checkup
The Org Checkup is EOS's version of a health scan across the Six Key Components®. Use it. Treat it like a heat map. Where are you strong? Where are you weak?
This is not about being right or wrong—it’s about creating visibility to improve. And that visibility drives growth.
5. Create a SWOT that creates Action
Strengths. Weaknesses. Opportunities. Threats. Not a corporate offsite version—a real one. This becomes an actionable list of long-term items we need to acknowledge and decide if now is the time. The action is, does this move to the Long Term Issues list for Day 2?
6. Challenge the Vision
It’s time to work through the Vision/Traction Organizer®:
- Core Values
- Core Focus™
- 10-Year Target™
- Marketing Strategy
- 3-Year Picture™
Don’t just read through it. Challenge it. Does it still inspire? Is it activated? Does everyone own it, or are they going along to get along?
One tip I always share here: this is our 'I Have a Dream' Speech, not a Plan Speech. Treat it accordingly. Dream, and dream big.
Day 2: Look Forward and Lock In
1. Recap Day 1
Get aligned on what you’ve already tackled. Check the Issues List. Re-ground in your 3-Year Picture. This sets the stage for real planning.
2. Create the 1-Year Plan
What needs to be true to make the right progress to be on track for our 3-Year Picture?
Lock in:
- Revenue, profit, and/or other lagging indicators
- Leading indicators (funnel metrics, activity goals)
- 3–7 company-wide goals
Make each one SMART and assign ownership to ensure accountability. No orphaned goals. If it matters, someone owns it.
3. Set Rocks for the Next 90 Days
Now shift to the next quarter. Ask: What must be true in the next 90 days to stay on track?
This typically leads to 3-7 Company Rocks. Then, each leadership team member sets 1-3 Individual Rocks. Too many, and you’ll dilute focus. Too few, and you’re sandbagging.
The discipline of the 90-Day World® is simple: short cycles, sharp focus, shared accountability.
4. IDS®: Solve the Long-Term Issues
The Long-Term Issues List is where the real work happens. This isn’t a brainstorming session—it’s about knocking down what could derail your year.
We use IDS to:
- Identify the root issue
- Discuss productively
- Solve permanently
Don’t try to solve everything, just the most important things. The rest can wait.
5. Conclude with Clear Next Steps
- Assign To-Dos.
- Determine what information should be shared with the rest of the company.
- Align on the communication plan.
Leadership alignment means nothing if the rest of the company is still guessing.
6. How did we do?
Finish with three questions:
- Feedback? (Where is your head and how are you feeling?)
- Were your expectations met?
- On a scale of 1–10, how would you rate it?
A 10 doesn’t mean perfect. A 10 means high performing. We were open, honest, healthy, and we have a plan to win.
If you're running EOS®, this is your moment; own it. Get your whole team on the same page. Set the plan and execute to win in the 90-Day World.
Final Thought
I am biased. In the 50+ companies I have coached that run on EOS®, I have never done it without Ninety. So I can’t comment on what that is like to not be powered by Ninety. But I can share that in my history, I have never had less than an 8.5 rating from a team when we did the right work and prepared to scale to win the next year.
My wish for you is that, however you decide to do your annual planning, please consider EOS powered by Ninety, as I believe it's the right path to plan and win the year.
Get the most out of your annual planning by setting your agenda in Ninety.
