Annual Planning Meetings Kinda Suck

Are you a New Year’s resolution person? I am. As an optimist, I love the opportunity to begin again with fresh goals, fresh energy, a chance to recalibrate at every level.

But a good friend and fellow EOS Implementer often reminds me: there’s nothing magical about January 1st. Winning next year starts months earlier, when you intentionally plan for it.

In the EOS® Meeting Pulse™, this shows up as our two-day Annual Planning Session, typically scheduled between October and the end of January.

So, what separates high-performing Annual Planning Meetings from those that kinda suck?
It’s not just the facilitator or the agenda. It’s the prework: the five deliberate steps you take before walking into the room.Over hundreds of sessions, I’ve found that the best teams invest deeply in five areas of prework:

1. Taking a Clarity Break™
2. Reviewing your Vision/Traction Organizer® (V/TO®)
3. Revisiting your SWOT
4. Preparing for Team Health
5. Aligning your Structure

Let’s unpack each step so you can walk into your next Annual Planning meeting ready, and not rusty.

Step 1: Take a Clarity Break™

What’s a Clarity Break? It’s one of the 20 tools in the EOS Toolbox®: a scheduled meeting with yourself designed to help you work on the business, not just in it.

Most leaders struggle to keep these appointments. But as you head into Annual Planning, a Clarity Break becomes indispensable.

Here’s how to make it work:

• Get out of your normal environment. Find a quiet place away from your office where you can think deeply.
• Start with a blank page. At the top, write a future date. For example, December 31, 2026.
• Visualize success. Ask yourself: What needs to be true by that date for the organization, my team, and myself (in that order) for this to be a win.
  
• Don’t worry about the “how.” Focus only on what needs to be true. This is “beginning with the end in mind.”

When you’re done, capture critical ideas as long-term issues for your Annual Planning session.

Remember: clarity isn’t found in motion; it’s found in margin.

Step 2: Review Your Vision/Traction Organizer® (V/TO®)

Your Vision/Traction Organizer® (V/TO®) isn’t just a worksheet — it’s your company’s Focus Filter and Culture Enabler. It works only when it’s alive and in use.

Before Annual Planning, revisit all eight questions on your V/TO®:

• Are we still aligned on our Core Values?
• Is our 10-Year Target™ still compelling and audacious?
• Does our 3-Year Picture™ still feel directionally correct,  and what’s changed as we go another year forward?

You’re not updating your V/TO® yet.  You’re using it as a lens to spot friction, spark ideas, and identify potential issues. Those insights become raw material for your Long-Term Issues List.

Step 3: Revisit Your SWOT

A well-prepared SWOT (Strengths, Weaknesses, Opportunities, Threats) widens your lens beyond the year you’ve been living in.

Too often, teams show up and try to build it live in 60 minutes. Don’t. Ask every leader to reflect and come ready.

Here are some prompts to jump-start that thinking:

• What are we the best at, and can we do more of it?
• Where did we stall, and what are we avoiding?
• What market opportunities exist that we’re not pursuing?
• Who are our top competitors, and why are they winning?
• Do we have the right structure to scale?

A thoughtful SWOT doesn’t just fill a flip chart; it reveals long-term issues that need real Traction®.

Step 4: Prepare for Team Health

Strong teams don’t accidentally become healthy; they choose to be.

In an EOS Annual Planning session, there are usually three Team Health exercises. The best preparation you can do is to revisit Patrick Lencioni’s The Five Dysfunctions of a Team.

I’ve been leveraging this model for over 20 years — long before EOS — because it’s timeless. It helps teams self-assess where they stand on:

• Trust
  
• Conflict
  
• Commitment
  
• Accountability
  
• Results
  

When teams understand that trust is the foundation for all the rest, the discussions in the session go deeper and the outcomes get real.

Step 5: Aligning Structure

Before locking in next year’s Targets and Goals, pause to review your Accountability Chart™. Ask yourself:

Is our structure supportive of where we want to go, not just where we are?

As you scale, your org design often shifts toward specialization, adding team leads, consolidating seats, or considering fractional roles like HR or Finance.

Remember: Culture may eat strategy, but structure enables both.

And if you’re not using the Org Assessment in Ninety, you’re missing a vital data point. This simple survey captures your team’s perspective across the Six Key Components® of EOS®: Vision, People, Data, Issues, Process, and Traction®.

It highlights where your organization is 80% Strong (and where the cracks are starting to show) before you get into the room to make decisions. It takes just minutes but sets the table for hours of meaningful dialogue.

Conclusion: Walk In Ready

My wish for you: that your Annual Planning sessions are high-performing and never kinda suck. You don’t warm up on Day 1. You show up ready,  clear, aligned, and energized.

Follow these five steps and see how it changes your session. If your team rates the meeting an 8 or higher, you’ll know it worked.

EOS® Powered by Ninety helps drive clarity during your Annual Planning Session and beyond,  enabling both alignment and execution. With cloud-based tools like the V/TO®, SWOT, and customizable survey tools, Ninety helps you build a clear, actionable plan for the year ahead. 

Try it free today.