Every December, we do a structured review. Not casual reflection—systematic analysis.

Here’s the checklist we use.

Business Performance

Revenue Review

• What was total revenue this year?
• How does it compare to last year? To plan?
• What was the growth rate by quarter?
• Which products/features drove growth?
• What was customer concentration? (Top 10 customers as % of revenue)

If you can’t answer these quickly, your reporting needs work.

Unit Economics

• What was CAC by channel?
• What was LTV by customer segment?
• How did payback period change?
• What was gross margin trend?

Unit economics that degraded need investigation. Improvement should be celebrated and replicated.

Burn and Runway

• What was average monthly burn?
• How does actual compare to budget?
• What’s current runway?
• What’s the plan if runway gets short?

Surprises here are bad. Know your numbers.

Product Review

What Shipped

• List major features released
• Which were successful? (Measured by usage, retention, revenue impact)
• Which flopped?
• What patterns explain success vs. failure?

Be honest about flops. Learning is the point.

What Didn’t Ship

• What was planned but not delivered?
• Why not? (Scope creep, complexity, priority change, resource issues)
• Was not shipping the right call?

Sometimes not shipping is correct. Sometimes it’s failure. Know which.

Technical Health

• How’s the codebase? (Honestly)
• What technical debt needs attention?
• Are there reliability issues that need investment?
• What infrastructure changes are needed?

Engineering always wants to rewrite everything. But some concerns are valid.

Team Review

Headcount

• How did team size change?
• Who did we hire? Were they the right hires?
• Who left? Why?
• What’s the retention rate?

Regretted attrition is a red flag. Investigate.

Performance

• Who exceeded expectations?
• Who needs coaching or a role change?
• Are we top-heavy or missing key skills?
• What training did we invest in?

High performers should feel recognized. Low performers should have a path to improvement or exit.

Culture

• What’s working in how we work?
• What’s not working?
• Is communication effective?
• Do people trust leadership?

Hard to measure. Important to assess. Anonymous surveys help.

Customer Review

Acquisition

• How many new customers?
• What channels performed best?
• What was conversion rate change?
• What did we learn about ideal customers?

Retention

• What was churn rate?
• What caused churn? (Product, price, competition, company death)
• Which segments retained best?
• What predicted churn?

Satisfaction

• What’s NPS or CSAT?
• What are the top complaints?
• What are the top compliments?
• Which customers would give references?

Competition and Market

Competitive Landscape

• What did competitors ship?
• Who entered the market?
• Who exited or struggled?
• How did our positioning change?

Market Trends

• What trends emerged this year?
• Which affected our business?
• What should we be watching for next year?

Don’t be paranoid. Do be aware.

What Worked / What Didn’t

The most important part of the review:

Three Things That Worked

Be specific. Not “marketing worked” but “LinkedIn content drove 30% of inbound leads.”

Three Things That Didn’t Work

Be honest. Not “timing was bad” but “we built the wrong feature because we didn’t talk to customers.”

Three Things to Try Next Year

Based on learnings, not wishful thinking.

Planning Inputs

Resource Planning

• What headcount do we need?
• What budget by function?
• What new capabilities do we need?

Goal Setting

• What are the 3-5 most important goals for next year?
• How will we measure them?
• What resources do they require?

Risk Assessment

• What could go wrong?
• What would we do if it did?
• What risks should we mitigate proactively?

The Process

Week 1: Data Gathering

Pull all the numbers. Compile the information. No analysis yet.

Week 2: Leadership Review

Leadership team reviews data, identifies patterns, drafts observations.

Week 3: Team Input

Share draft with broader team. Gather input. What did leadership miss?

Week 4: Finalize and Plan

Synthesize input. Finalize review. Transition to planning.

The Output

We produce a 5-10 page document:

1. Executive summary (one page)
2. Performance against goals
3. What worked / what didn’t
4. Key learnings
5. Priorities for next year

Shared with the whole company. Transparency about how we did and where we’re going.

Why This Matters

Most startups don’t do structured reviews. They run on vibes and whatever feels urgent.

Structured review prevents:

• Repeating mistakes
• Ignoring successes
• Drifting without direction
• Misaligned understanding across team

One week of reflection prevents twelve months of wandering.

Do the review. Make it habit.