One On One for Slack

Personalized one-on-one coaching, directly in Slack

One On One by Catch Up AI is an autonomous coaching assistant that conducts private employee check-ins directly in Slack.

It helps employees discuss blockers, reflect on progress, define next steps, and follow up on commitments through personalized Slack conversations.

Add to Slack
Slack app
One On One coaching assistant robot holding a Slack check-in clipboard

A conversation that keeps commitments visible

One On One checks in, asks follow-up questions, and revisits agreed actions over time.

What One On One does

A private coaching conversation for every check-in

One On One keeps employee reflection and follow-through in a focused Slack conversation, with administrator-controlled options for summaries and connected signals.
  • Conducts personalized employee check-ins.
  • Communicates through private Slack direct messages.
  • Identifies blockers, progress gaps, missed follow-ups, and relevant goals.
  • Suggests practical next steps.
  • Tracks agreed actions across multiple weeks.
  • Can optionally generate concise manager summaries when enabled by an administrator.

How it works in Slack

A simple, private rhythm for weekly follow-through

The workspace administrator sets the boundaries. One On One handles the conversational check-ins in Slack.
  1. 1

    A workspace administrator installs One On One.

  2. 2

    The administrator configures eligible users, check-in cadence, office hours, integrations, and manager summaries.

  3. 3

    One On One starts a private conversation with an employee in Slack.

  4. 4

    The employee replies naturally in the Slack DM.

  5. 5

    One On One asks relevant follow-up questions and suggests actions.

  6. 6

    The assistant revisits previous commitments during later check-ins.

  7. 7

    Optional manager summaries are shared only according to the administrator’s configuration.

One On One does not publish employee coaching conversations in public Slack channels.

Slack conversation example

Natural follow-up, in the employee’s Slack DM

One On One can use a previous commitment as the starting point for a focused check-in. The mockup shows an employee discussing a blocker and choosing a practical next step.
1:1

One On One

App · Direct message

Private

This week

One On OneAPP10:02 AM

Hi Maya. Ready for your weekly check-in?

Last week you planned to finish the onboarding documentation. How did it go?

Employee10:04 AM

It is nearly finished, but I am waiting for two answers from engineering.

One On OneAPP10:05 AM

What is the most useful next step?

Employee10:06 AM

I will send them the exact questions this afternoon.

One On OneAPP10:07 AM

Great. I will follow up with you later this week.

Illustrative mockup of a private Slack direct message. It shows the type of conversation an employee can have with One On One.

Administrator configuration

Administrators decide how One On One operates

The administrator controls the workspace settings that shape check-ins, access, integrations, and optional manager summaries.

Check-in frequency

Choose how often One On One starts an employee check-in.

Office hours

Set the approved hours for check-in conversations.

Eligible employees or teams

Select the employees or teams who can use One On One.

Enabled integrations

Choose which approved integrations are available to One On One.

Manager-summary settings

Configure whether concise manager summaries are enabled.

Slack permissions and connected data sources

Review workspace permissions and the data sources connected to the experience.

Data and integrations

Use only workspace-approved signals

Depending on the enabled configuration, these may include:
  • Slack activity
  • Jira activity
  • GitHub activity
  • Calendar events
  • Employee goals
  • Pulse-check responses
  • Previous One On One conversations and follow-ups

One On One supports workplace reflection and communication. It does not automatically make hiring, termination, promotion, compensation, disciplinary, legal, or medical decisions.

Privacy and security

Private by design, controlled by the workspace

One On One conversations take place in private Slack direct messages. Workspace administrators control enabled integrations, user access, check-in timing, and manager-summary settings.
Privacy and Security

Product focus

One On One and Catch Up AI are complementary products.

One On One

One On One is employee-focused and provides private conversational coaching through Slack direct messages.

Catch Up AI

Catch Up AI is manager-focused and provides team-level notifications, insights, analytics, and feedback workflows.

Installation and first use

From Slack approval to the first private check-in

Use the Add to Slack button above to start the workspace installation, then follow these steps.
  1. 1

    Click Add to Slack.

  2. 2

    Select a Slack workspace.

  3. 3

    Review and approve the requested permissions.

  4. 4

    Complete the administrator configuration.

  5. 5

    Enable One On One for selected employees.

  6. 6

    Employees open One On One under Apps in Slack and communicate through its Messages tab.

Support

Need help getting started?

For installation, configuration, privacy, or product support, contact info@thecatchup.ai.

Email support