Running 1:1s and conversations

A conversation in Performance Blocks is a long-running, asynchronous thread between you and one of your direct reports. Each direct report has exactly one open conversation at a time, and that thread becomes the connective tissue between observations, objectives, decisions, and follow-ups.

Conversations are not a replacement for live 1:1s — they are a place to prep for them, capture decisions during them, and follow through after them.

How conversations work

Each conversation is a private thread between you and one direct report. Both of you can post messages, share observations, attach decisions, and create follow-ups. The thread persists indefinitely; old conversations are archived rather than deleted, and the search bar on the Conversations page covers your full history.

Posts in a conversation can be:

• Plain text — short messages, links, replies.
• Rich text — formatted prose with headings, lists, code blocks, and quotes.
• Shared observations — an observation you authored, dropped into the thread for discussion.
• Decisions — a structured callout that records what you and the employee agreed to.
• Follow-ups — a tracked task with an owner and a due date.

Anyone with access to the conversation sees every post in chronological order. There are no separate channels or topics within a single conversation; structure comes from how you write, not from the data model.

Starting a conversation

If you do not have an active conversation with a direct report, you can start one from any of these places:

1. Dashboard — open the employee's profile and click Start conversation on the Conversations tab.
2. Conversations page — click New conversation, pick the employee, and confirm.
3. Observations — when sharing an observation, you can start a new conversation if none is open.
4. Keyboard shortcut — press c c to open the new conversation form.

Each direct report has a single active conversation. If one already exists, the Start conversation action takes you into that thread instead of creating a new one. To begin fresh, archive the existing conversation first; the archived thread remains searchable.

Sharing observations into a conversation

Observations are most powerful when discussed. To share an observation into a conversation:

1. Open the observation from the employee's profile or the Observations page.
2. Click Share to conversation in the action bar.
3. Optionally add a note explaining why you are sharing it now.
4. Click Share.

The observation appears in the thread as a structured card showing the type (Strength or Opportunity), the four sections (context, behavior, impact, recommended action), and the date the behavior occurred. The employee can reply directly under the card.

You can share Strengths and Opportunities at any time. Sharing an Opportunity for the first time should usually be paired with a live conversation — async-only delivery of corrective feedback often lands harder than intended.

Sharing multiple observations

If you want to share several observations as a batch — for example, before a 1:1 — open each observation, share it into the conversation, then post a brief framing message at the top of the thread tying them together. There is no bulk share action; the deliberate, one-at-a-time flow is intentional to keep each piece of feedback discussable.

Conversation starters

With Henry: On the Agentic plan, Henry can generate conversation starters for any direct report based on recent activity.

A conversation starter is a short, prepared talking point you can post into a conversation to kick off discussion. Starters are useful before live 1:1s, when you have not posted in a while, or when you want to reflect on a recent piece of work.

Generating starters with Henry

In the Henry panel, ask "what should I talk about with [employee] this week?" Henry runs the conversation starter flow:

1. Pulls observations from the last 30 days.
2. Reviews any in-progress objectives owned by the employee.
3. Looks at unread messages in the current conversation.
4. Drafts 3–5 starter prompts grouped by theme — celebration, follow-up, blocker, decision needed.

You see each starter as a card with a title, the body text, and the underlying evidence (observations, objectives, messages). For each starter you can:

• Post to conversation — drop it directly into the thread.
• Edit — open in the rich text editor before posting.
• Discard — remove from the list.

Henry never posts a starter without your explicit action.

Manual starters

Without Henry, you can still draft a starter manually. Open the conversation, click New post, and use the rich text editor to write your talking point. Save as a draft if you want to refine it before sharing — drafts are private to you until posted.

Rich text editing

The conversation editor supports the formatting you would expect:

Format	Shortcut
Bold	Cmd/Ctrl + B
Italic	Cmd/Ctrl + I
Heading 2	## then space
Heading 3	### then space
Bulleted list	- then space
Numbered list	1. then space
Code block	three backticks
Quote	> then space
Link	Cmd/Ctrl + K

Posts autosave as drafts every few seconds. You can leave a draft and come back to it; it appears at the top of the thread with a Draft badge until you post or discard.

You cannot attach arbitrary files to conversation posts. Use links to documents in your file storage — when an integration is connected, link previews are rendered inline.

Decisions

A decision is a structured post that records what was agreed. Use decisions when you and the employee land on something concrete — a change in approach, a commitment to take on new work, a deferral.

To record a decision, click Add decision in the conversation footer. Fill in:

• Decision — one sentence describing what was agreed.
• Context — optional background.
• Owner — usually the employee, but can be you or "shared."
• Date — when the decision was made.

Decisions appear in the thread as a callout card and are listed separately on the Decisions tab of the conversation, so you can scan recent decisions without scrolling the whole thread.

Decisions are surfaced in performance summaries as evidence of clarity and follow-through. Use them sparingly — every message is not a decision.

Follow-ups

A follow-up is a tracked task tied to the conversation. Each follow-up has:

• Title — what needs to happen.
• Owner — you or the employee.
• Due date — optional, but recommended.
• Status — Open, In progress, Done, Cancelled.

Follow-ups appear in the thread when created and on the Follow-ups tab. The owner of a follow-up is notified on creation and reminded as the due date approaches. Mark a follow-up done from either the thread or the tab; both you and the employee can change the status of any follow-up.

Follow-ups are not a project management tool — keep them lightweight. If you find yourself adding more than five at a time, the work probably belongs in your team's task tracker.

Conversation history and search

The Conversations page lists every conversation you have, active and archived. You can:

• Filter by employee, by activity recency, or by archive state.
• Sort by last activity, by employee name, or by start date.
• Search the full text of every post and observation in your conversations using the search bar at the top.

Search is scoped to your conversations only. You cannot see another manager's conversations unless explicitly delegated by the employee — and that delegation is always temporary.

Archiving conversations

Archive a conversation when you want to start a new thread with a fresh slate. Archiving:

• Removes the conversation from the active Conversations view.
• Keeps the full content searchable.
• Allows you to start a new conversation with the same employee.

To archive: open the conversation, click the overflow menu, and choose Archive. To restore: filter for archived conversations, open the one you want, and click Restore.

Best practices

Cadence

Most teams settle into one of these cadences:

• Weekly — for newer employees, contractors, or anyone in a stretch role.
• Biweekly — the default for most direct reports.
• Monthly — for senior, autonomous reports who do not need frequent check-ins.

Cadence is about the conversation thread, not just live meetings. Even if you only meet live every two weeks, you might post a starter or share an observation in between.

Structure

A useful weekly conversation thread tends to include:

1. A starter or framing message (you).
2. The employee's update — wins, blockers, asks.
3. Any observations you want to discuss.
4. Decisions and follow-ups, captured as structured posts.
5. A short close — what we agreed, what we are watching.

You do not need every part every time. The structure exists to make the thread scannable.

Follow-through

The single highest-leverage thing you can do in conversations is close the loop on follow-ups. When a follow-up is done, mark it done in the thread and post a one-line note about how it landed. Employees notice, and the discipline compounds across summaries and reviews.

Async first, live second

Live 1:1s remain valuable, but the goal of the conversation thread is to make those live meetings shorter, denser, and more decision-oriented. If your live 1:1 is the only place anything happens, you are spending the meeting on status updates that could have lived in the thread.

Notifications

By default, you are notified when:

• A direct report posts in a conversation you have not opened in 24 hours.
• A follow-up assigned to you is due in 48 hours or overdue.
• An observation is replied to in a conversation.

You can adjust frequency and delivery channel under Settings → Notifications. On the Agentic plan, conversations can also be delivered to Slack or Teams, with replies posted back into the thread automatically.

Privacy

Conversations are private to you and the employee. They are not visible to:

• Other managers in your chain.
• Your org admin (admins can see metadata — start date, message count — but not content, except via support requests with employee consent).
• Henry's RAG knowledge base. Conversation content is never used as training data, and it is excluded from the chat-time RAG context except where you explicitly invoke it (for example, by asking Henry to summarize the thread).

Troubleshooting

I cannot start a conversation

You can only have conversations with your direct reports. If a name is missing from the picker, check the org chart and confirm the reporting relationship is current.

My drafts are not saving

Drafts autosave every few seconds while connected. If you see a "draft not saved" indicator, check your network connection. Refresh the page and your most recent saved draft will be there.

A follow-up reminder fired but the task is done

The follow-up status is the source of truth — change it to Done in the conversation thread and the reminders stop.

What to read next

• Creating observations — the evidence you share into conversations.
• Writing performance summaries — conversations are referenced as evidence in summaries.
• Managing objectives — link conversations to objective updates.