Introduction 

Great planning sessions don’t happen by accident. They happen because leaders prepare with clarity, curiosity, and courage. 

Yet most companies — especially those doing it for the first time — rush in without alignment, without data, and without the right conversations already underway. The result is predictable: lots of discussion, little decision. 

This short guide walks you through five practical steps that will help you prepare for a focused, energizing, and truly productive annual planning session. Whether you’re leading it yourself or partnering with a Scaling Up coach, these steps will help your team come in clear on where you’re headed, honest about where you are, and ready to make decisions that move the company forward. 

Each step builds on the next — from big-picture vision down to day-one readiness — and each connects directly to the Scaling Up framework you’ll use in your two-day planning process. 

STEP 1 – Describe a Vivid Vision 

Purpose 

Every successful planning cycle starts with a clear picture of the future. A well-crafted Vivid Vision gives your team something concrete to align around—a shared image of success three years out. Without it, even strong operators spend their energy rowing in different directions. 

Common Pitfalls 

• The CEO assumes everyone already knows where the company is headed. 

• The “vision” is a list of goals, not a vivid description of a future state. 

• The document is written but never shared, debated, or refined. 

Coach’s Approach 

You ask the CEO to draft the Vivid Vision in narrative form, describing what the company looks and feels like three years from now—its culture, customers, performance, and impact. 
A few days before planning day, the CEO circulates it to the leadership team. During the session, you facilitate discussion: 

• What resonates most? 

• Where do we need to stretch? 

• What’s missing? 
  The outcome is clarity: the CEO owns the what, the team owns the how. 

Practical Actions / Tools 

• Block a half-day of quiet thinking time away from the office. 

• Use prompts from your Vivid Vision Guide. 

• Circulate the draft to the team 3–5 days before planning. 

• Ask each leader to note one area they’d “double down on” and one they’d “push further.” 

• Schedule 45 minutes on Day 1 of the session for the CEO to share and discuss it. 

Takeaway 

Once the picture is painted, the next step is seeing the canvas as it really looks today—facing the brutal facts. 

STEP 2 – Face the Brutal Facts 

Purpose 

Before setting new goals, your team must agree on what’s true. Annual planning loses power when the room holds competing versions of reality. Facing the brutal facts—about performance, people, customers, and the market—creates the shared foundation that every great plan is built on. 

Common Pitfalls 

• Leaders skip reflection and jump straight to next year’s goals. 

• Conversations focus on opinions instead of data. 

• Feedback loops from employees and customers are missing. 

• Teams sugarcoat weaknesses or avoid sensitive truths. 

Coach’s Approach 

Instead of defending positions, the team listens for patterns—where alignment is strong and where perception gaps exist. Your role is to help them confront facts without blame. 
Preparation includes multiple lenses: 

• The Leadership Vision Alignment Survey to capture leaders’ views of strengths, constraints, and aspirations. 

• A Start–Stop–Keep exercise to gather employee input on what’s working and what isn’t. 

• Optional 4Q Customer Conversations from Scaling Up to hear directly from clients. 

• A short financial snapshot—sales, gross margin, key trends. 

Practical Actions / Tools 

• Have the leadership team complete the Vision Alignment Survey 2–3 weeks before planning. 

• Assign HR or an admin to run the Start–Stop–Keep pulse. 

• If possible, schedule 3–5 customer calls using the 4Q framework. 

• Summarize findings on one slide per category (Leaders, Employees, Customers, Financials). 

Takeaway 

Once the team has faced what’s true, the next step is making sure the people in the room are healthy enough—and aligned enough—to do something about it. 

STEP 3 – Get Healthy to Get Aligned 

Purpose 

Strategy depends on team health. Even the sharpest plan will crumble if the people in the room don’t trust one another enough to debate, disagree, and commit. Healthy teams don’t just execute better—they think better together. 

Think of the early NASA Apollo teams: a mix of engineers, astronauts, and flight directors who argued fiercely but trusted completely. That combination—candor plus commitment—turned near-disaster into triumph. Annual planning works the same way: the team’s chemistry determines the quality of the plan. 

Common Pitfalls 

• Teams assume alignment and skip the hard work of building it. 

• “Niceness” gets mistaken for trust; conflict is avoided rather than used productively. 

• Meetings stay polite on the surface but unresolved underneath. 

• The CEO carries the emotional load while others stay silent. 

Coach’s Approach 

By mid-morning on Day 1, the room is warm, markers are uncapped, and the masks are off. The team has already reviewed The Five Dysfunctions of a Team framework, identified which dysfunction they handle best and which challenges them most, and shared a few low-stakes trust-building exercises. 

They’ve also explored each other’s DiSC behavioral styles—why one person pushes hard for detail while another moves fast toward decisions. Laughter breaks tension; empathy replaces assumptions. You can feel the shift as conversations become more direct, more constructive, and noticeably lighter. The group realizes they’re already operating more like a true leadership team than a collection of department heads. 

This moment anchors Rockefeller Habit #1: The executive team is healthy and aligned. 

Practical Actions / Tools 

• Make The Five Dysfunctions of a Team required reading two weeks before planning. 

• Have participants identify one behavior that helps and one that hurts team performance. 

• Begin Day 1 with your Accelerated Five Dysfunctions Workshop (90–120 minutes), which includes the trust-building and DiSC components described above. 

• Capture the team’s “health commitments” on a flip chart or shared digital board and revisit them quarterly. 

Takeaway 

A healthy team multiplies every strategic decision they make. 
When people trust one another enough to challenge ideas and commit together, the strategy they create will hold up under pressure. 

STEP 4 – Establish the Scoreboard 

Purpose 

Why do fans at a game stay glued to the scoreboard? Because it tells them who’s winning. The same is true in business. Plans gain power when performance becomes visible — when goals turn into numbers your team can track, celebrate, and improve. A scoreboard turns effort into evidence, making progress impossible to ignore. 

Common Pitfalls 

• Teams have activity lists but no clear success metrics. 

• Financial data stays in the CEO’s or accountant’s head. 

• KPIs are too many, too vague, or not connected to outcomes. 

• Numbers exist but aren’t reviewed rhythmically, so lessons are lost. 

Coach’s Approach 

You help teams build this discipline from the ground up. 
Even if the company lacks strong data habits, you start simple: What do we already know — sales, margin, cash? Then, what should we know to manage better? 
Using Scaling Up’s Data Execution Discipline and the FACe Tool, you guide them to define both: 

• Leading Indicators – activities that predict success. 

• Lagging Indicators – results that confirm it. 

During Day 2, you often facilitate a “Scoreboard Design” session: the team agrees on which metrics matter, who owns them, and how frequently they’ll be reviewed in meetings. 
A few accurate numbers tracked consistently will increase visibility and heighten accountability. 

Practical Actions / Tools 

• Gather at least two years of basic financial data (Revenue, Gross Margin %, Cash on Hand). 

• Use the FACe Tool to connect each function with its leading and lagging KPIs. 

• Limit the company dashboard to 10 core metrics or fewer. 

• Define one Critical Number for the next 12 months and one for the next 90 days. 

• Assign an “owner” for every metric — the person responsible for explaining it each week. 

• Build the first version of your dashboard during Day 2; refine it later. 

Takeaway 

A scoreboard turns conversations from opinion to observation. 
When everyone can see the same data, alignment becomes easier — and the team is ready to Shape the Insights that will drive next year’s plan. 

STEP 5 – Shape the Insights 

Purpose 

The final step before planning day is to make sense of everything you’ve gathered. By shaping the insights, you convert a flood of data, survey results, and feedback into a few clear themes that will focus your session. 
This is the bridge between preparation and strategy — the moment when raw information becomes shared understanding. 

Common Pitfalls 

• Teams arrive at the session with piles of input but no synthesis. 

• The CEO or facilitator tries to process everything live in the room, and the noise drowns the signal. 

• Key topics get missed because no one connected patterns ahead of time. 

• The session starts with confusion instead of clarity. 

Coach’s Approach 

You guide clients to distill what they’ve learned from all the pre-work — the Vivid Vision, Leadership Alignment Survey, Start-Stop-Keep, and any customer or financial insights — into a concise storyline about the business. 
Typically, you’ll review this material with the CEO and one or two key leaders in a short prep call. Together, you identify: 

• The two or three questions that most deserve team attention (“What must be true next year for this to be a breakout year?”). 

• Any sensitive issues that need structured discussion time. 

• The order of topics that will help the team move from reflection to decision. 

AI can dramatically accelerate this stage. By feeding survey responses, notes, and summaries into an AI assistant, leaders can quickly surface recurring themes, extract language patterns, and even generate draft “insight summaries” or key questions for the team to discuss. It’s an efficient way to turn unstructured data into clarity — freeing human time for interpretation and decision-making. 

You may draft a brief Planning Prep Summary — one or two pages highlighting patterns and framing questions — so participants walk in ready to contribute rather than absorb. 

Practical Actions / Tools 

• Schedule a 60-minute prep meeting with the CEO and 1–2 leaders one week before the session, and review all survey and feedback summaries to identify recurring themes. 

• Narrow the list of planning topics to five or fewer. 

• Draft a simple “Session Brief” (Key Insights → Key Questions → Desired Outcomes). 

• Email the brief to all participants two days before the session with this message: “Come ready to discuss, not discover.” 

Takeaway 

Input without synthesis is just noise. 
When teams shape the insights before they meet — turning scattered data into focused themes — the planning session can turn those insights into action. 

Closing Thoughts 

Imagine walking out of your next planning session feeling clear and confident about where your company is headed. Your leadership team is aligned, the path ahead feels challenging but doable, and you know how to communicate the plan so everyone can carry a piece of the load. That’s what great preparation delivers — a plan that energizes instead of exhausts. 

Preparation isn’t busywork; it’s the discipline that makes planning worth doing. The difference between an average session and a transformative one is simple: whether the team shows up ready. 

If you want your next session to produce decisions, not decks — and to leave your team focused, aligned, and motivated — that’s the work I help leadership teams do. 
Visit GoPerficio.com or reach out directly at Trey@GoPerficio.com