Run Better 1-on-1’s With Employees Using AI

In this guide, you will learn how to run better 1-on-1s with employees or mentees using Claude with Cowork turned on. You will set up a Claude project from past call transcripts, create your own 1-on-1 template and evaluation rubric, and use it to help the people you manage make progress more consistently.

• Managers who run recurring 1-on-1s and want a more consistent structure for coaching, follow-up, and progress tracking.
• Founders, team leads, or operators who manage researchers, contractors, creators, or analysts and want better visibility into work quality over time.
• Anyone mentoring multiple people who wants to turn scattered call notes into a reusable template, rubric, and tracker.

You will build a Claude project that stores your 1-on-1 history, creates a reusable call template and rubric, and tracks progress over time. The finished workflow can also create a simple dashboard from your rubric CSV so you can see how the team is trending.

• Claude desktop app (https://claude.com/download)
• Previous 1-on-1 transcripts, reading notes, or call summaries (completely optional)

Once the tracker works, the next move is turning it into a live dashboard artifact. In the video guide, we have Claude create a CSV to track transcripts, rubrics, scores, and follow-ups, then use that CSV as the source of truth for a dashboard you can reopen as the team changes over time.

Use this prompt after Claude creates the tracker:

Make an artifact that visualizes the team's performance over time.

Base it on the one-on-one tracker CSV.

Include:
- each person's latest average rubric score
- category-level trends across the team
- open follow-up items
- a short summary of each person's most recent performance
- any missing data that makes the dashboard less reliable

The first dashboard may be simple if you only have one rubric per person. That is fine. The important part is that the dashboard is built from the CSV, so every new transcript and rubric update can feed the same progress view.

The simplest upgrade is to have Claude tighten the rubric and call template as more transcripts come in. After every few 1-on-1s, ask:

Review the latest 1-on-1 transcripts and tell me whether one-on-one-template.md or evaluation-rubric.md should be updated.

Only suggest changes that are supported by repeated patterns in the transcripts.
Keep the template short enough to use during a live call.

You can also use the same project when you schedule the next call. If Claude has access to your calendar, ask it to draft the agenda from the tracker before the invite goes out:

Schedule my next 1-on-1 with [Employee].

Look at our most recent 1-on-1 transcript, completed rubric, and one-on-one tracker CSV.

Create a short agenda for the calendar invite that includes:
- the main follow-up from last time
- one progress question
- one blocker question
- one commitment to revisit

The main idea is simple: your 1-on-1s should not disappear after the call ends. With a Claude project and Cowork turned on for the organizing work, every transcript can make the next conversation easier to run.

Keep the system human. Use Claude to organize the history, draft better questions, and spot patterns. You still decide what matters, what is fair, and how to coach the person in front of you.