Annual Planning Fatigue and Frustration: Ninety Answers

I’ve been fortunate to learn from several great mentors, people who shared earned wisdom, not just advice. One principle that’s stuck with me is this:

Entrepreneurs need to do more with less forever.

And to live that out, you have to lean into technology. Hard work alone won’t get you there. (Thanks, Bob.)

In the age of AI, we keep questioning the role software plays in building and scaling companies. Too often, it gets framed as an either/or: people or tech. In my view, it’s both. The real opportunity is in intelligently combining concepts, tools, and disciplines to build a great company.

I want to talk about how Ninety can be a true partner in creating, executing, and achieving your annual plan. And yes, I can already hear the skeptics, and I welcome you to the conversation. You may already have plenty of free or previously purchased tools where information goes to sit. That’s not what we’re after. EOS® is about bringing your business to life. A living operating system that helps you win the week, win the quarter, and ultimately, win the year. Let’s get after it.

What Makes EOS® Annual Planning Different?

There are already so many excellent resources that answer this question, so I offer this with humility. Start by reading Traction by Gino Wickman. Chapter 8 explains both the why and the how. Then explore the blog series from Ninety, where I’ve contributed insights based on what I've seen in real client work.

In the EOS world, we don’t treat annual planning like a check-the-box meeting. It’s a pivotal 2-day offsite where leadership teams:

• Build trust and deepen relationships
• Recast their 10-Year Target, 3-Year Picture, and 1-Year Plan
• Set the right Rocks to drive Traction® in Q1
• Clear the issues list and solve the root of what’s holding them back

It’s where clarity meets commitment, and your leadership team leaves with a real plan to roll out to the rest of the company and execute.

How Can Ninety Help You Execute Your Annual Plan?

If you’re running EOS manually (using PDFs, slide decks, and hand-written notes), you’re not just wasting valuable time. You’re also missing the simplicity and clarity the right tool can bring. Ninety is the largest and longest-running software platform built for companies running on EOS. It was designed to solve the exact pain points that show up before, during, and after your annual planning session by giving you:

• One-click access to your Vision/Traction Organizer®
• Live issues lists, sortable by company, team, or department
• Rock planning and tracking that cascades down into weekly Level 10 Meetings
• Org Assessments to evaluate company and team health
• Real-time accountability with the Scorecard and To-Dos tools

No more hunting for documents. No more wondering where the vision lives. Everything is centralized, visible, and “Shared by All.”

What Are the 5 Most Powerful Tools in Ninety for Annual Planning?

I remember entering the room with great anticipation for a client’s annual planning session. It was our second year working together leveraging EOS powered by Ninety, and the team was having a good (even great) year. But within minutes, I could feel something was off.

As we moved through Day 1, it became clear that the team had just come off a strong year, but the road ahead looked tough. I paused and reminded them to trust the process. The answers are in the tools. That moment reinforced something I’ve seen again and again: All the EOS tools matter, but some matter more during annual planning. At least in my experience. So let’s break it down:

1. Vision/Traction Organizer (V/TO®)

Solves: Misalignment on vision and strategy

Without a clear and shared vision, planning turns into debate. The Vision/Traction Organizer in Ninety ensures your entire team is aligned on the same 10-Year Target, 3-Year Picture, 1-Year Plan, and quarterly Rocks. Unlike paper copies that get lost or forgotten, Ninety keeps this living document front and center so everyone knows where you’re going and how you’ll get there.

2. Scorecard(s)

Solves: Lack of control and progress to goals

When planning for the year ahead, we need to start with the end in mind, then work backward. What needs to be true, and by when? Then we define the weekly, monthly, or quarterly actions that move us there. This isn’t about reporting what happened. It’s about defining what needs to happen and assigning clear ownership.

These leading and lagging indicators don’t just support your annual budget and departmental P&Ls. They drive results. When teams commit to the On Track/Off Track mentality, Scorecards become a real-time performance engine. With Ninety, these metrics are linkable across people, teams, and the entire organization. That means you can close the loop, tie issues to the measurables that consistently fall short, and stay focused on hitting 80% or better.

3. Org Assessment Tool

Solves: Hidden gaps in your Six Key Components®

Annual planning is your chance to reset, but you need insight first. The Org Assessment tool inside Ninety gives every leader a voice on how the business is doing across EOS’s Six Key Components®. You’ll get a real-time heat map showing where your team sees strengths and where the gaps lie. This becomes your road map for setting issues, Rocks, and even long-term strategic initiatives.

4. Performance Reviews and Quarterly Conversations

Solves: Performance and feedback gaps

I believe I’m a good leader, and I’m working to get better every day. The people I support likely have valuable feedback to help me do that. That’s why we use Quarterly Conversations and Annual Reviews. They create space for real input and real growth.

When we’re wrestling with Right People, Right Seat issues, the GWC® test (Get it, Want it, Capacity to do it) often surfaces capacity or skill gaps. In my experience, many leaders don’t have clear answers because they haven’t been consistently having Quarterly Conversations. That’s the first coaching point: Start with care, then move to performance. These two ideas aren’t in conflict. They’re both required.

Ninety’s format includes a 360 LMA review addressing the five questions on Leadership and Management. I personally have executed 100+ of these in the software, and I love it. It reminds me of one of my favorite quotes from Doc Rivers: “Good players want to be coached, but great players want to know the truth.” Let’s aim for great.

5. Issues List / IDS® and SWOT

Solves: Symptoms vs core issues and the future

I’m not a fan of the tyranny of the blank page, and a blank whiteboard might be worse. All that possibility and no clue where to begin. When in doubt, sweep it out. I like to start with two simple lists: What’s Working and What’s Not Working Yet. Set a five-minute timer and give yourself space to reflect. That pause often brings the clarity you need.

Once you've created the list, open the SWOT tool in Ninety to categorize the list by Strengths, Weaknesses, Opportunities, and Threats. Not everything will fit neatly, and that’s okay. The real value is clarity. Is this something to address this year or later? Making that decision is key to your progress.

Most leadership teams don’t lack ideas. They’re just buried in unresolved issues. That’s why we lean on Ninety’s Issues tool to capture, prioritize, and knock down the right ones using IDS® (Identify, Discuss, Solve). During Annual Planning, this becomes the focal point for clearing roadblocks, closing open loops, and removing the drag that slows execution in the year ahead.

Common Annual Planning Mistakes

The truth is most annual planning sessions fall apart because the team lacks preparation and walks in without the facts, focus, or frameworks they need to make meaningful decisions. Here's are some of the most common mistakes I see:

• Vague goals: You’ve got a list of priorities that sound good in the room, like improve client experience, optimize operations, or drive growth. But there’s no clear owner, timeline, or way to measure success. These goals fade fast because they were never rooted in accountability.
• Misaligned teams: Half your team is thinking 10 years ahead, while the other half is stuck putting out this week’s fires. Some are ready to grow, but others are burned out and just trying to survive the quarter. Without alignment, your plan becomes a collection of opinions, not a shared strategy.
• Forgotten commitments: Maybe you made some bold decisions at last year’s annual. But when you pull up the plan, it’s not clear who owned what. There’s no record of completion. Accountability is missing, and without a system to track it, those commitments never stood a chance.
• “We talked about this last year” syndrome: This one stings. You surface the same strategic issues over and over again, but nothing changes. That’s a symptom of weak issue solving, lack of follow-through, and zero visibility across meetings.

The right annual planning software can help your team avoid these pitfalls and achieve year-over-year alignment.

Annual Planning Without Execution Is Just a Nice Offsite

Annual planning should be the most valuable two days of your year, but it only works if you turn ideas into action. EOS provides the framework. Ninety makes it real. If your last planning session felt like a waste (or you’re still managing Rocks in spreadsheets), it’s time to upgrade.

Let's make next year your most aligned, accountable, and high-Traction year yet. Don’t just plan — implement. Ninety brings EOS to life in real time and helps you show up to annual planning with clarity, leave with commitment, and operate every quarter of the year with confidence. Now's the time.

Run your next annual planning session with Ninety and build a lasting foundation. Start your free trial of Ninety now.