WhoToAsk
Socrates, the WhoToAsk owl

Free and open source

Know who to ask.

Ask a question about your work. WhoToAsk tells you who on your team knows the answer, why, and which channel to post it in.

Install See the code
brew install --cask dcadolph/tap/whotoask

MIT licensed. Runs on your machine, with or without an AI model.

What it does

A name, and the reason for it.

WhoToAsk looks through the tools your team already uses and turns them into answers you can act on.

Who knows this?

Type something like "who knows about billing retries" and get the people who have done the work, why each one came up, and how sure WhoToAsk is. It also names the channels where the topic comes up.

Who is the only one?

It shows where only one person knows how something works, so the team can spread that knowledge before it turns into a problem.

What happened last time?

When the person who fixed something has moved on, it finds the conversation where they fixed it.

One person, one entry

Slack, GitHub, Jira, and the org chart all name people a little differently. WhoToAsk matches them up, so each person shows up once.

Ground rules

Not for judging people.

WhoToAsk shows where knowledge and systems are at risk. It never ranks, scores, or labels people, and what it finds must not be used for performance reviews, layoffs, or any other decision about someone's job.

If one person turns out to be the only one who knows something, that means the team needs a second person who knows it.

Get it

Install WhoToAsk.

Homebrew

On macOS.

brew install --cask dcadolph/tap/whotoask

Go

Anywhere Go runs.

go install github.com/dcadolph/whotoask@latest

Download

Archives for Linux, macOS, and Windows are on the releases page.

Check a download before you run it

The release workflow signs checksums.txt with Sigstore, and every archive carries SLSA build provenance.

id='^https://github.com/dcadolph/whotoask/\.github/workflows/release\.yml@refs/tags/v'
cosign verify-blob checksums.txt \
  --signature checksums.txt.sig \
  --certificate checksums.txt.pem \
  --certificate-identity-regexp "$id" \
  --certificate-oidc-issuer https://token.actions.githubusercontent.com
sha256sum -c checksums.txt --ignore-missing
gh attestation verify whotoask_<version>_linux_amd64.tar.gz --repo dcadolph/whotoask

On macOS without GNU coreutils, use shasum -a 256 -c checksums.txt --ignore-missing for the second line.

Try it

Try it in a minute.

1

Start with a repo

Point it at a repository you already have. It reads the git history and shows which folders only one person knows. No tokens, nothing fetched.

whotoask demo --repo .
2

Ask a question

Load your team, then ask in your own words.

whotoask index --source org-csv --file examples/people.csv
whotoask ask --pretty "who do I talk to about billing retries"
3

Look back

When the person who knew has left, ask what happened.

whotoask recall "certificate renewal"

Then run whotoask connect to add your other tools one at a time.

Sources

Works with the tools you already use.

WhoToAsk talks only to the sources you pick, with your own tokens.

  • Slack
  • Slack workspace export
  • GitHub
  • Git
  • CODEOWNERS
  • Jira
  • Confluence
  • PagerDuty
  • Microsoft Graph
  • Org chart CSV
  • Time-entry or matter CSV
  • JSON records

Privacy

Stays on your machine.

Keyword search needs no AI model and always works. For smarter search and written answers, use a local Ollama model, or turn on Claude, Gemini, or OpenAI yourself.

Out of the box, everything is worked out on your machine and nothing goes to an outside model. Read the privacy policy.