How to Run Your First Performance Review Cycle

You’ve decided it’s time for your company’s first performance review cycle. Maybe you’ve hit 20 employees and feedback has become inconsistent. Maybe an early employee has left and cited a lack of clarity around career growth opportunities. Whatever the trigger, you’re now staring at a process that enterprise companies have entire teams dedicated to running.

You don’t have an entire team. You might be wearing three hats already. This guide is for you.

Running your first performance cycle doesn’t require enterprise software or months of preparation. It requires a clear plan, realistic expectations, and the right shortcuts. Here’s how to do a lot with a little.

Start with the end in mind

Before building any process, answer these questions:

What decisions will these reviews inform? Compensation adjustments? Promotions? Development plans? Your answer shapes everything. If reviews won’t connect to real outcomes, employees will treat them as busywork.

What’s your timeline? Most first cycles take 4-6 weeks from launch to completion. Block that time now. According to Engagedly, managers spend an average of 210 hours per year on performance management activities. Your goal is to get value without that time sink.

Who needs to be reviewed? Standard practice is to include employees who’ve been with the company at least 3-6 months. Newer hires haven’t had enough time to demonstrate performance patterns.

Who writes the reviews? Typically direct managers, but in small companies, founders often review everyone initially. That’s fine for your first cycle.

The four phases of a performance cycle

Every review cycle follows the same basic structure. Here’s how to execute each phase without a dedicated HR team.

Phase 1: Self-reviews (5-7 days)

Self-reviews give employees a chance to highlight their contributions. They also surface accomplishments managers might have missed.

Keep it simple. Three to five questions are plenty:

What are you most proud of accomplishing this period?
Where did you struggle or fall short of your goals?
What support do you need from your manager?
What are your goals for the next period?

Set a firm deadline. Give employees one week. Longer timelines just mean more procrastination. Send reminders at the halfway point and 24 hours before the deadline.

The scrappy shortcut: Instead of building forms, use a shared doc template or even Slack threads. Windmill’s AI assistant, Windy, handles this entirely through Slack conversations—employees chat naturally about their work, and Windy compiles structured self-reviews automatically. Rho completed self-reviews in just 2.5 days using this approach.

Phase 2: Peer feedback (5-7 days, can overlap with self-reviews)

Peer feedback adds perspectives managers don’t have. Skip this phase for your first cycle if you’re truly strapped for time, but it significantly improves review quality.

Let employees nominate peers. Ask each person to suggest 2-3 colleagues who can speak to their work. This surfaces cross-functional contributions you’d otherwise miss.

Keep peer reviews short. Two questions work:

What does this person do well?
What’s one area where they could improve?

Anonymous or attributed? For first cycles, anonymous feedback typically yields more honest responses. You can shift to attributed feedback once trust in the process is established.

Phase 3: Manager reviews (7-10 days)

This is where most time gets consumed. The traditional approach—managers staring at blank documents trying to remember six months of work—is brutal. TruQu research found that traditional reviews make performance worse one-third of the time, often because managers rush through them.

Gather context first. Before writing anything, pull together:

The employee’s self-review
Any peer feedback collected
Project outcomes and metrics from your tools
Notes from 1:1s throughout the period

Use a consistent structure. Every review should cover:

Key accomplishments with specific examples
Areas for development with actionable suggestions
Overall performance assessment
Goals for the next period

The time-saving reality: This is where small companies lose the most hours. Windmill integrates with tools like GitHub, Jira, Salesforce, and Slack to automatically surface employee contributions. Managers select key wins and development areas, then Windy generates a draft of the review. It takes ~6 minutes per direct report for the entire process.

Phase 4: Calibration (1-3 days)

Calibration ensures consistency. Without it, one manager’s “exceeds expectations” is another’s “meets expectations.”

For small companies, keep it simple. Gather managers (or just founders, if that’s your structure) for a single meeting. Review ratings distribution and discuss outliers.

Questions to ask:

Are we rating against the same standards?
Does anyone have context that would change a rating?
Are there patterns we should address (team-wide issues, bias concerns)?

Flag discrepancies. If one manager rates everyone as exceptional while another rates everyone as average, dig into why. Windmill’s calibration dashboard automatically highlights these discrepancies and generates pre-reads for calibration meetings—cutting session time by 75% or more.

Tools: Enterprise vs. scrappy vs. AI-powered

Your tool choice depends on budget, timeline, and how much process overhead you can tolerate.

The enterprise option (Lattice, CultureAmp, 15Five)

These platforms are comprehensive. They’re also designed for companies with dedicated HR teams to configure and manage them. For a 30-person company running its first cycle, they can be overkill—expensive, complex to set up, and feature-heavy when you need simplicity.

According to PayScale, 95% of managers hate giving appraisals. Adding a complicated system doesn’t help.

The scrappy option (Google Docs, Notion, spreadsheets)

Totally viable for your first cycle. Create templates, share them manually, track completion in a spreadsheet. The upside: free and familiar. The downside: you become the system. Every reminder, every follow-up, every compilation falls on you.

This works once. It doesn’t scale to your second or third cycle without burning you out.

The AI-powered option (Windmill)

Windmill was built for exactly this situation: companies that need the output of a mature performance management process without the overhead. Here’s what that looks like in practice:

Setup takes 5 minutes. Connect your tools, import your org chart, launch your cycle.
Self-reviews happen via Slack. Windy chats with employees naturally—no forms, no portals, no training required.
Context is gathered automatically. Windmill pulls from GitHub, Linear, Figma, Salesforce, and 30+ other integrations so managers aren’t starting from scratch.
Reviews are drafted for you. Managers review AI-generated drafts, select key points, and add personal touches. Average time per review: 6 minutes.
Calibration is data-driven. Automatic discrepancy flagging and pre-read generation.

For small companies, this is the difference between a process that takes your entire month and one that takes your afternoon.

Common first-cycle mistakes to avoid

Waiting for perfect

Your first cycle won’t be flawless. Ship it anyway. You’ll learn more from running an imperfect cycle than from endlessly planning a perfect one.

Making reviews too long

Long reviews take forever to write and nobody reads them carefully. Aim for one page per person. Focus on what matters: accomplishments, development areas, and next steps.

Surprising people

If a performance review is the first time someone hears critical feedback, you’ve failed as a manager. Reviews should confirm what’s already been discussed in 1:1s, not introduce new information.

Ignoring the follow-through

A review without follow-up is pointless. Schedule check-ins at 30 and 60 days to discuss progress on development areas. Otherwise, the whole exercise was theater.

Doing everything manually

Small teams try to bootstrap everything. It’s admirable but unsustainable. The hours you spend chasing self-reviews and compiling feedback are hours you’re not spending on actual people development. Invest in automation early.

A realistic timeline for your first cycle

Here’s a sample 5-week timeline that balances thoroughness with practicality:

Week 1: Preparation

Finalize review questions and rating criteria
Communicate the process to all employees
Set up your tools (even if that’s just shared docs)

Week 2: Self-reviews and peer nominations

Employees complete self-reviews
Employees nominate peers for feedback
Send reminders at midweek

Week 3: Peer feedback

Peers submit feedback
You compile materials for managers

Week 4: Manager reviews

Managers write reviews (with whatever context you’ve gathered)
Initial review of ratings distribution

Week 5: Calibration and delivery

Calibration meeting to align ratings
Managers deliver reviews in 1:1s
Document outcomes and action items

With Windmill, this timeline compresses significantly. Rho completed their entire cycle—self-reviews through manager reviews—in 8 days.

Making it sustainable

Your first cycle is the hardest. Here’s how to make subsequent cycles easier:

Document everything. What worked? What didn’t? What questions came up? Your future self will thank you.

Build continuous feedback habits. The more feedback flows throughout the year, the less work reviews require. Regular 1:1s and continuous feedback tools reduce review season from a scramble to a summary.

Automate what you can. Every manual step is a step you’ll have to repeat. Invest in systems that do the gathering and compiling for you.

Get feedback on the process. Ask employees and managers what worked. Iterate for next time.

Key takeaways

Keep your first cycle simple. Three to five questions for self-reviews, consistent structure for manager reviews, one calibration meeting.
Set firm deadlines. 5-7 days per phase. Longer timelines just mean more procrastination.
Gather context before writing. Self-reviews, peer feedback, and work data make manager reviews faster and fairer.
Don’t do everything manually. Your time is too valuable. Use tools that automate the gathering and compiling.
Follow through. Reviews without action items are theater. Schedule check-ins to discuss progress.
Iterate. Your first cycle won’t be perfect. Learn from it and improve.

Running performance reviews without a full HR team is challenging, but it’s absolutely doable. The key is focusing on outcomes over process—what decisions will improve, what conversations will happen, what clarity will employees gain.

Start simple. Get the reps in. And if you want to skip the manual work entirely, Windmill gives small teams the performance management capabilities of companies ten times their size—without the overhead.