5 Annual Planning Pitfalls and How to Avoid Them

Sometimes the best place to start is at the end, and that’s how the annual planning process begins. In Q4, we start by reviewing the year, then the prior quarter. This grounds us in what we achieved and what we learned. From there, we can look ahead with clarity.

I recently wrote a blog called How to Create an Annual Plan in 5 Steps. The inspiration came from a conversation with a leader who was self-implementing EOS® and felt overwhelmed by the annual planning process. I wanted to simplify it for them. When we followed up last week, we talked about the common pitfalls I've seen teams run into again and again.

Even with the best intentions, a lot of teams struggle to follow through on their annual plan. They set goals that sound inspiring in the room but fade by the end of Q1. They launch ambitious initiatives without structure, accountability, or real buy-in. And when this happens, the result is predictable: lost Traction®, a confused team, and stalled growth. The truth is, passion isn’t enough. Without a system for execution and accountability, even strong leadership teams fall apart.

Let’s break down the five common annual planning pitfalls and how to avoid them so you can keep your organization moving forward and focused on what matters most.

1. Lack of Preparation

Lack of preparation is the first place annual planning breaks down, and it shows up long before the team enters the room. To be successful, the entire team has to do the work ahead of time.

That's why I always recommend the team takes a Clarity Break to reflect and dream. These undistracted moments, aided by tools like your V/TO® and SWOT, will allow you to think about how you, your team, and your entire organization performed over the previous year. What needs to be true for you to achieve your 10-Year Target and 3-Year Picture? How can you win
the next year? I know I've struggled at times to prepare properly, especially when I feel stuck or frustrated. But this is the exact moment to invest in finding clarity. Because grinding it out by doing the same thing you did last year won't get you to a different result.

The Fix: Embrace the 90-Day World® process. This includes three quarterly planning sessions, plus having consistent State of the Company Meetings and Quarterly Conversations. But before you can meet, you need to prepare, so take Clarity Breaks and be ready to work on the business, not just In it. (Want more information about aligning your team for successful annual planning? Check out this blog.)

2. Overloaded Priorities

Trying to do too much at once is a fast track to burnout and disengagement. When everything is a priority, nothing is. And when leaders spread their teams too thin by trying to tackle too many initiatives at once, they can't make meaningful progress on any of them. This kind of overload creates fatigue, decision paralysis, and a sense of failure when the team can’t keep up.

Over time, overloaded priorities break trust in both leadership and the planning process as a whole. Teams begin to see strategic plans as aspirational, not actionable, and engagement plummets.

The Fix: Focus on fewer, better priorities. During annual planning, identify your 3–7 most important company goals for the quarter and make them Rocks. Ask, "What must be true this year for us to stay on track toward our vision?" Focus on the initiatives that will create the biggest impact.

3. Lack of Accountability

You get to the end of a quarter only to find out the project that everyone was excited about never got done. Does this sound familiar?

This all-to-common scenario occurs when a team doesn’t know who’s accountable for what. Goals get assigned to groups or departments, and when progress stalls, there’s no single person responsible. Nebulous ownership results in delays, finger-pointing, and lack of follow-through.

This is one of the most preventable pitfalls. When a Rock or To-Do doesn’t have a clear owner, it rarely gets done on time. Accountability ensures not just completion, but also ownership of outcomes, both good and bad.

The Fix: Every Rock and To-Do needs an owner. Using the EOS Accountability Chart in Ninety clarifies roles and ensures the right people are in the right seats so there's no more confusion. With clear lines of ownership, teams move faster and more confidently.

4. Not Using Data to Drive Decisions

Too many strategic plans rely on instinct, not insight. Leaders often default to assumptions or gut feelings, especially when their company data is hard to access or hasn’t been consistently tracked. But without hard numbers, strategic decisions are educated guesses at best.

Over time, these guesses lead to misallocated resources, missed targets, and recurring mistakes. Data not only informs good planning but also reveals trends, uncovers risks, and validates progress throughout the year.

The Fix: Build your Scorecard in Ninety. Keep track of measurables, each quarter’s grade, your progress in the Org Check-up, and improvements in the Five Dysfunctions of a Team framework. All of these impact your progress.

5. No Follow-Through System

Great planning sessions are wasted when there's no plan for how to execute. It’s easy to get energized during annual planning, but without a system to revisit goals and track progress, that energy fades quickly. By Q1, the day-to-day whirlwind takes over and the strategic plan gathers dust.

Without follow through, team members start to feel like planning is just another box to check rather than a meaningful road map. Execution breaks down, and teams revert to reactive mode.

The Fix: Use Ninety to keep your strategy alive. Embed your priorities into the Issues, To-Dos, and Meetings tools. With weekly check-ins and clear accountability inside the platform, your team can win the week, win the quarter, and win the year.

Moving Ahead with Confidence

Ninety brings your entire strategic plan into one platform. Your Vision/Traction Organizer®, Scorecards, Issues Lists, and Rocks all live in one place where they can be understood and followed by all. No more spreadsheets. No more forgotten action items. No more ideas written on notepads or whiteboards. Just clear, connected tools that turn your annual plan into reality.

The best leadership teams don’t just make plans. They commit to the systems that turn those plans into results. Tools alone don’t create clarity. But the right tools, used consistently, reinforce the discipline you need to build momentum quarter after quarter.

Want your next year to be your strongest yet? Avoid these common pitfalls, build better habits, and use Ninety to keep your organization focused, aligned, and on track.

Don’t wait until your Annual Planning derails. Start building your plan to win 2026 in Ninety today. Start a free trial of Ninety now.