1:1s

1:1s are most effective when both the manager and employee come prepared. Without preparation, meetings often turn into surface-level recaps of recent work instead of meaningful conversations about priorities, challenges, and growth. Running 1:1s on Windmill ensures that agendas are clear before the meeting begins, context is aggregated from across your workflows and routines, and both parties enter the meeting informed so time is spent on impactful discussion.

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How 1:1s work in Windmill

Windmill automatically finds all of your upcoming 1:1s from your calendar. In order for this to work, Google must be connected to your account. You can also create ad-hoc 1:1s without a calendar event. This is useful for impromptu conversations or when you want to track a 1:1 that isn’t on your calendar. Each 1:1 has a shared agenda and notes space where you can:

• Add agenda items anytime
• Take notes before, during, or after the meeting
• Record action items or next steps

Anything added in this shared space is visible to both participants.

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1:1 Prep

When Prep is turned on, Windmill reaches out on Slack to proactively engage both manager and employee ahead of the meeting. You’ll configure when you want Windy to reach out to an employee before a scheduled 1:1. Windy will send your employee a message in Slack to collect their agenda items, asking questions like “What would you like to talk about?” and “Anything to add to the agenda?”

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What Windy surfaces

Windy surfaces relevant context such as:

• Last meeting’s agenda and notes
• Progress on action items or goals
• Recent updates, feedback, or key events

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When Prep is off

If 1:1 Prep is off, the 1:1 still exists—you can always add agenda items, take notes, or capture action items. But Windy will not send proactive prompts or reminders.

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Prompting Windy directly

Whether 1:1 Prep is on or off, you can always prompt Windy directly in Slack for things like:

• Adding topics to the agenda
• Sharing agenda items the employee has already added
• Pulling up previous 1:1 agenda items, any recent updates or feedback
• Leaving yourself private notes

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Configuring 1:1 Prep

Managers configure 1:1 settings for each person individually. This lets you tailor the experience (questions, cadence) depending on the person. You can:

• View upcoming scheduled 1:1s for that employee
• Edit the discussion guide or add custom questions
• Customize when you want Windy to reach out to the employee before the 1:1
• Customize when you want Windy to reach out to you ahead of the meeting to help you understand what the employee wants to discuss

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Ownership rules

When you enable 1:1 Prep between two employees, there is always one owner of the prep settings who can edit them. The other participant will not be able to make changes.

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Who is the owner

• The owner is the person who initially sets up 1:1 Prep for the pair
• The owner controls configuration details such as prompts, visibility, and other settings
• The other participant can view and contribute to prep notes but cannot modify the setup itself

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Who can enable 1:1 Prep

• You can enable 1:1 Prep with people who report to you (directly or indirectly) or with peers
• You cannot enable 1:1 Prep for your manager (directly or through the org chart). The option to start prep with your manager is hidden
• For peers, whichever employee sets up 1:1 Prep first becomes the owner
• Once 1:1 Prep is set up, the other person will no longer be able to edit the settings

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Changes in reporting relationships

• If the org chart changes and one employee becomes the other’s manager, the existing owner can disable 1:1 Prep at any time
• Once disabled, the other person (now the manager) can enable prep again and become the new owner

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Summary

• If you report to someone (directly or indirectly), you cannot enable 1:1 Prep for them
• If someone reports to you (directly or indirectly), you can enable 1:1 Prep for them
• If you’re on separate teams, it’s treated as a peer relationship, and whoever sets up 1:1 Prep first becomes the owner

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Bulk configuration

Configure 1:1 prep settings for multiple employees at once.

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Calendar Integration and Automatic Identification

Windmill requires Google Calendar to be connected to your account for 1:1s to work. Once connected, Windmill automatically syncs calendars and identifies which meetings are 1:1s.

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How Windmill identifies 1:1s

Windmill automatically identifies 1:1s based on:

• Meeting name: Meetings with titles like “1:1”, “1-on-1”, or “one on one”
• Number of attendees: Meetings with two participants

This automatic identification works for most cases. If Windmill incorrectly labels a meeting, you can manually adjust it. You can manually control which meetings are treated as 1:1s in the 1:1s section of Windmill.

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Start 1:1

Use “Start 1:1” to immediately begin an ad-hoc 1:1 with someone—no calendar event required.

1. Navigate to the employee’s profile.
2. Click Actions in the top right.
3. Click “Start 1:1”.

This creates an ad-hoc 1:1 for right now and generates AI discussion topics.

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Add 1:1 from Calendar

Use “Add 1:1 from Calendar” to link a calendar event as a 1:1.

1. Navigate to the 1:1s tab or the employee’s profile.
2. Click Actions in the top right.
3. Click “Add 1:1 from Calendar”.
4. Choose the meeting to add.

This adds the 1:1 label to the meeting in Windmill.

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Remove a 1:1

1. Navigate to the 1:1s tab.
2. Click into the person with whom that 1:1 is.
3. Click the three dots next to the meeting.
4. Select “Remove meeting”.

This removes the 1:1 label from the meeting in Windmill.

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Context aggregation

Windy collects responses, builds the 1:1 agenda, and shares it with the manager at the pre-configured time before the meeting. Windy enriches the agenda with helpful background information, pulling from connected systems such as GitHub, Slack, and other Windmill routines. For example, if you have the Continuous Feedback routine enabled, the report will include recent feedback both given and received by the employee. All items include citations, showing where the data came from.

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Shared agenda and notes

Each 1:1 has a shared agenda and notes scratch pad, visible to both the manager and the employee. Anything added in this shared space is visible to both participants. If you want to record private reflections, you can message Windy directly in Slack—those won’t appear in the shared agenda/notes space.

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Using 1:1s

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In the meeting

Armed with the agenda and context, managers and employees can focus on problem-solving, coaching, and strategic conversations. No more spending the first half of the meeting on status updates.

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Suggested Topics

Suggested topics show up automatically for your next upcoming 1:1, and only for that meeting. Key timing details:

• Topics do not appear for past 1:1s.
• Topics begin generating shortly before Windy sends the 1:1 prep message in Slack.
• Topics remain visible until 30 minutes after the scheduled meeting time — useful if your conversation runs long.

You don’t need to enable anything for topics to appear; they show up automatically.

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Who can see suggested topics

Visibility is role-aware:

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For managers

• Topics are generated about your direct report.
• Only you can see these topics.
• Topics use the same underlying research as the 1:1 background report.

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For individual contributors

• Topics are generated about you.
• You never see topics about your manager.
• Windy uses only the data you have permission to see.

This ensures managers and ICs each receive the right level of context without exposing sensitive information.

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Catch Me Ups

When in a 1:1 with one of your direct or indirect reports, managers will have access to a “Catch Me Up” panel with the relevant details about the team member. This “Catch Me Up” experience aggregates all of the data from the available connections, and any relevant Windy interactions. These are only visible to managers, and are not available for any cross-functional 1:1s. “Catch Me Up” reports generate automatically every Sunday. They also regenerate with up-to-date information whenever Windy reaches out for 1:1 Prep.

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After the meeting

• You can always go back and edit or append meeting notes or action items
• You can always message Windy for meeting notes or summaries, and you’ll retain the history of agendas and notes to revisit in future 1:1s
• If a meeting recording (Zoom, Google Meet, or Roam) is available, it will automatically show up in the 1:1 notes section. Note that it may take a few hours after the meeting for the recording to appear

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1:1 Stats

Windmill tracks 1:1 patterns across your organization. Click View Stats at the top of the 1:1s page to see how consistently 1:1s are happening.

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What you’ll see

• Manager 1:1 Leaderboard — See which managers consistently meet with their team and which don’t. Ranks managers by the percentage of direct reports they’ve met with in the selected time period.
• Time Spent in 1:1s — Understand how much time managers are investing in their people. Shows each employee’s meeting frequency and total time in 1:1s.
• Employees Without Recent 1:1s — Spot manager-employee relationships that may need attention. Lists employees who haven’t had a 1:1 with their manager within the selected threshold.
• 1:1 Pairs — See whether teams are capturing value from 1:1s through documentation. Shows all 1:1 pairs with total meeting count and percentage with notes in Windmill.

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Who can view stats

• Managers see stats for themselves and anyone who reports to them (directly or indirectly). Toggle between “My Direct Reports” and “All” to adjust scope.
• HR Admins & Workspace Admins see stats for the entire company.
• Delegated Access users can view stats for employees they have access to.
• Individual Contributors without direct reports or delegated access cannot view the Stats page.

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Importing 1:1 notes

Import notes from Notion, Google Docs, or other platforms to consolidate your 1:1 history in Windmill.

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How it works

• Notes are matched to meetings by date.
• If a meeting doesn’t exist, Windmill creates one.
• Notes are only imported to meetings that don’t already have notes. Existing Windmill notes won’t be overwritten.

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How to import

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Importing from Notion

Notion’s toggles and formatting can make copy/paste tricky. For best results, export as Markdown first.

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Importing from Google Docs