It starts as one question in a thread. Someone asks Bob to pull last quarter's numbers for the board deck. Then finance chimes in with a correction. Then sales wants a different cut. By the afternoon there are forty replies, three versions of the same chart, and nobody is sure which one is current or what it all cost.
That thread stopped being a question hours ago. It became a team project with an AI teammate in it, and a chat thread is a poor place to run one. Working sessions are how HeyBob handles AI agent team collaboration: one room, one goal, your whole team and Bob working on it together, one running cost, and a recap at the end.
Why threads break down for group work
A thread is good for a quick ask. You ask, Bob does it, done. Group projects are different. They have a goal that takes many turns to reach. Several people add context, change their minds and approve pieces along the way.
In a busy thread, each new message can feel like a fresh job. The decisions from an hour ago sit far up the scroll. Costs show up as a string of small charges. When the work is done, the thread just goes quiet.
What a working session is
A working session is a shared room in the HeyBob app with one stated goal, such as "Finish the Q3 board deck" or "Clean up the vendor list before the audit." Anyone in your workspace with the link can join. Everyone sees the same conversation, who else is in the room, and how many credits the work has used so far.
Inside the room, Bob works from two things: the goal, and everything said in the session. He doesn’t drag in other conversations or old jobs. When the work needs something outside the room, like a file in your drive or a record in your CRM, he goes and gets it with the apps you have connected, the same way he does for any other job.
The conversation carries through the whole session. When it gets long, Bob condenses the older parts but keeps the goal, the decisions and the file names word for word, so nothing important drifts.
How a session starts
- In the HeyBob app. Choose New working session, type the goal, and share the link with your team.
- From Slack. Type /bob session followed by the goal. Bob posts a join link in that channel. The link asks people to sign in to your workspace and opens the HeyBob app, or offers to download it.
- When Bob suggests it. If a thread has a clear end goal and real back and forth, or two or more people working with him, Bob may ask once: "Want to move this work into a working session?" Accept, and the room opens with the thread's first request as its goal and the thread so far as its opening conversation. He asks rarely, and he backs off if people keep ignoring the offer.
Working together with Bob
Once the room is open, people talk to Bob and to each other in plain words, as they would in any chat. A few things make it work for a group.
Nobody waits in line. If someone adds a thought while Bob is in the middle of a turn, he folds it into the work he’s already doing. There’s no queue of separate jobs.
Approvals stay with the right person. When Bob needs an OK to send or change something outside HeyBob, the approval card goes to the person whose message led to that action, under your usual admin rules. Everyone in the room can see the card. Only that person can approve it.
Anyone can change the gear. The session starts on Auto. Any participant can switch the model or how hard Bob thinks, from the choices the opener is allowed to use. A line in the conversation says who changed it and to what, so nobody is surprised.
One running cost, on one bill
The room shows one running total against the session's own cap. The cap is 2,000 credits by default, and the person who opens the session can set it, though never above their own allowance or your workspace cap. The person who opened the session pays. Teammates who join don’t split the bill out of their own allowances.
When the total reaches 90 percent of the cap, Bob doesn’t stop mid-thought. He asks your admins to raise the cap, naming the goal and who is paying. The turn he’s on finishes. If the cap is reached and nobody has raised it, Bob won’t start another turn until someone does. For how credits and allowances work in general, see credits and spending caps.
After the session closes, your usage history shows it as one line, labeled with the goal, instead of dozens of small charges. Each turn is still metered as it happens, the same way any other job is.
Closing with a recap
When Bob thinks the goal is met, he says so and offers to close the session. Any participant can confirm, or keep going. Anyone in the room can also close it from the top of the screen. If a session goes quiet for 24 hours, it closes on its own.
Closing posts a recap in the room: the goal, what got done, what is left, the files produced, and the total cost. If the session started in Slack, the recap also goes back to the original Slack thread, so people who never joined can see how it ended.
A closed session stays readable afterward. It can’t be changed, so the record of what the team decided stays put.
Thread or session: which to use
| A quick ask in a thread | A working session | |
|---|---|---|
| Best for | One job, one person | A goal that takes many turns and several people |
| What Bob works from | Your message and recent context | The goal and the whole session conversation |
| Cost | One receipt per job | One running total and its own cap |
| How it ends | When the job is done | A recap with what got done, what is left and the total |
What it doesn’t do yet
- Workspace members only. People outside your company can’t join a session yet.
- The work happens in the app. Slack gets the join link and the recap, but the session itself runs in the HeyBob app on Mac, Windows and Linux. iPhone and Android are on the way.
- Microsoft Teams is coming soon. Today you can start a session in the app or from Slack.
- Closed means closed. A closed session can’t be reopened. Start a new one if the work picks back up.
Common questions
Does everyone in a working session need the HeyBob app?
Yes. The work happens in the HeyBob app on Mac, Windows or Linux. A session started from Slack posts a join link in the channel, and the link opens the app or offers to download it. iPhone and Android are on the way.
Can people outside our company join a working session?
Not yet. Anyone in your HeyBob workspace who has the link can join. The join link asks people to sign in to that same workspace, so outside guests cannot get in.
Who pays for a working session?
The person who opened it. Every turn uses credits the same way any other job does, and the session shows one running total. When it closes, your usage history shows it as one line labeled with the goal.
What happens when a working session reaches its cap?
Each session has its own cap, 2,000 credits by default. When it gets close, Bob asks your admins to raise it instead of stopping mid-thought. The turn he is on finishes. If the cap is reached and nobody raises it, Bob will not start another turn until someone does.
Do working sessions work in Microsoft Teams?
Bob on Microsoft Teams is coming soon. Today you can open a working session in the HeyBob app or from Slack.
Try it on your next group project
Next time a thread starts growing into real work, move it into a room. Get the HeyBob app, or add Bob to Slack and type /bob session with your goal. For more on how Bob works with a team, read what to look for in an AI coworker for Slack, how approvals keep Bob's work in check, and the teammates and permissions guide.