Send coaching tips in Slack

Turn on Slack coaching DMs so people get short, private tips about their own AI sessions.

Slack coaching sends each person a short direct message with tips about their own recent sessions, such as when to start fresh or turn off a setting that costs more. Each message covers only the recipient's own sessions, and it never mentions money.

Who can do this: Admins turn coaching on or off. Everyone who receives a tip gets it in their own Slack DMs.

Before you start

  • Slack must be connected to Tokenize. See Connect Slack.
  • Each person needs a Slack account with the same email address they use in Tokenize. Tokenize finds people in Slack by email.

Turn on coaching

  1. Go to Settings → Integrations.
  2. On the Slack card, turn on Slack coaching DMs.
  3. You see "Slack coaching enabled."

Coaching is off until an admin turns it on. Connecting Slack doesn't turn it on by itself.

To pause it, turn off Slack coaching DMs. This stops new tips and DMs. Alerts and weekly digests keep their own settings.

When tips arrive

Tips go out on weekdays. A person only gets a message on a day Tokenize finds something worth mentioning in their sessions, so many people go days without one.

Each message is short, covers a topic or two, and links to the sessions it's about so the person can open them in Tokenize. It ends with a View All Opportunities button.

What tips cover

Tips focus on the habits that make the biggest difference to how well AI works, such as:

  • Session habits, like knowing when to start fresh.
  • Repeated work a skill or scheduled task could take over.
  • Settings that cost more than the work needs.
  • Tools and connectors that fail or go unused.

The advice matches the tool. For example, Claude Code and Codex users are told to use /compact, and Claude Cowork and Cursor users are told to start a new task or chat.

Privacy

A tip only describes the recipient's own sessions, which they can already open in Tokenize. It contains no costs. See Privacy and redaction.

Troubleshooting

The toggle is turned off and says "Connect Slack to enable coaching." Slack isn't connected. Connect it first, then turn on coaching.

The card says "Reconnect Slack to resume coaching." The Slack connection was revoked. Reconnect Slack from the same card.

Someone isn't getting tips. Check that their Slack email matches their Tokenize email. If your Slack connection was set up a long time ago, reconnect Slack so Tokenize has permission to look people up by email and send DMs.