HR & RECRUITING
Surface Stretch Roles at Tenure Milestones
When an employee hits a tenure milestone, it identifies open roles one level up that match their skills, then drafts a manager talking-points doc and notifies the manager.
How it runs
The automated pipeline, trigger to output.
- TriggerDaily check for tenure milestones in NotionNotion
- ActionRead open roles one level up from Mondaymonday.com
- ActionMatch skills and draft manager talking pointsOpenAI
- ActionSave development brief as a Notion pageNotion
- OutputEmail manager with brief link and contextGmail
What it does
When an employee reaches a tenure milestone (such as 18 or 36 months in role), this workflow finds open internal roles one level up that align with their skills, drafts a short development-conversation brief, and notifies their manager so growth gets discussed proactively.
When to use it
Use this to make retention conversations happen on time. Instead of waiting for an employee to threaten to leave, managers get prompted at natural growth moments with concrete next-step roles already identified.
How it works
- 1A daily schedule checks the Notion directory for employees crossing a tenure milestone.
- 2For each one, the flow reads open roles from the Monday board and filters to roles one level above their current band.
- 3An OpenAI step matches their skills to those stretch roles and drafts manager talking points covering fit, gaps, and a suggested development path.
- 4The brief is saved as a Notion page in the manager's space.
- 5Gmail notifies the manager with a link to the brief and the milestone context.
Set it up
What you configure once, before turning it on.
- 1Connect NotionPages, databases, comments.
- 2Connect monday.comVisual work management for teams.
- 3Connect OpenAIModels, embeddings, files.
- 4Connect GmailRead, draft, send, label.
- 5Set each agent's modelWe leave models unset so you pick the tier — fast + cheap, or top-quality.
- 6Tune it to your dataEdit the prompts, filters, and field mappings so it matches how your team works.
- 7Test, then turn it onRun once against a sample, confirm the output, then enable the trigger.
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