1:1's
Why Use the One-on-One Routine?
One-on-ones are most effective when both the manager and employee come prepared. Without preparation, meetings often turn in to surface level recaps or recent work, instead of meaningful conversations about priorities, challenges, and growth.
The One-on-One Routine ensures that:
Agendas are clear before the meeting begins.
Context is aggregated from across your workflows and Routines (goals, blockers, priorities, feedback, etc.).
Both parties enter the meeting informed, so time is spent on impactful discussion.
Who shows up on this 1:1 list?
Windmill will automatically find all of your upcoming 1:1's.
Why enable 1:1 prep?
1:1 are most effective when both the manager and employee come prepared. Without preparation, meetings often turn into surface level recaps or recent work, instead of meaningful conversations about priorities, challenges, and growth.
The 1:1 prep ensures that:
Agendas are clear before the meeting begins.
Context is aggregated from across your workflows, goals, recaps, blockers, priorities, feedback, etc.
Both parties enter the meeting informed, so time is spent on impactful discussion.
1:1 Prep
When Prep is turned on, Windmill reaches out on Slack to proactively engage both manager and employee ahead of the meeting. In the configuration, you'll select when you want Windy to reach out to an employee before a scheduled 1:1. Depending on when you configure this, Windy will send your employee a message in Slack to collect their agenda items. Windy asks meeting prep questions like “What would you like to talk about?” and “Anything to add to the agenda?” and surfaces relevant context, such as:
Last meeting’s agenda and notes
Progress on action items or goals
Recent updates, feedback, or key events
If 1:1 Prep is off, the One-on-One still exists: you can always add agenda items, take notes, or capture action items — but Windy will not send proactive prompts or reminders. Whether One-on-One 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 (more below in Shared Agenda & Notes Space section)
Setup & Configuration
You configure 1:1 settings for each person individually. This lets you tailor the experience (e.g. 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 asking those questions to help prepare for the conversation.
Customize when you want Windy to reach out to you ahead of the meeting to help you understand what the employee wants to discuss, get you up to speed and make any adjustments to the agenda.
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.
Ownership rules
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.
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.
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.
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.
Context Aggregation
Windy collects these 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.
Shared Agenda & Notes Space
Each 1:1 has a shared agenda and notes scratch pad, visible to both the manager and the employee.
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. If you want to record private reflections, you can message Windy directly in Slack — those won’t appear in the shared agenda/note space.
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.
After the Meeting
You can always go back and edit or append meeting notes or action items
You can always slack 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 (e.g. Zoom, Google Meet, or Roam) is available, it will automatically show up in the One-on-One Notes section. Note that it may take a few hours after the meeting for the recording to appear.