# Manager Difficult Conversations: Prepare in Slack

Source: https://maito.app/workflows/coach-managers-on-hard-conversations

Tell Maito about the situation and it builds a plan that follows your feedback guidelines, with an opening, questions to ask and what to avoid saying.

Managers get help preparing feedback that follows your guidelines.

[People and HR](https://maito.app/workflows/team/people-and-hr) · When you ask · Updated October 19, 2026

Works with

-   Slack
-   Email

## How do you prepare a difficult conversation?

To prepare a difficult conversation, tell Maito what happened in Slack. It applies your company's feedback guide, turns the facts into an opening that names the pattern and its impact, suggests questions to ask, lists things to avoid, and can help you rehearse the reply the employee is most likely to give.

## How it's done today

New managers wing it.

## What Maito does

1.  Read the situation
2.  Suggest how to frame it using your guidelines
3.  Draft talking points

## Example

**Tom** (4:05 PM):

I need to give feedback to someone on my team who keeps missing deadlines. 3 times since August. Help me prepare.

**Maito** (4:07 PM):

Here's a plan using the Northstar feedback guide: situation, behavior, impact.

**Open with the pattern:** "The vendor report was due Sep 11, the audit pack Oct 2 and the supplier list Oct 14, and each landed 2 to 4 days late. Each delay held up someone else."

**Then ask:** "What's getting in the way?" Listen before suggesting anything.

**Agree on a next step:** work is flagged by Wednesday if it's at risk, and you check in Nov 2.

**Catch:** the guide says feedback should come within 2 weeks of the event. The Sep 11 one is past that, so frame this as a pattern and not as that incident.

Want to try your opening line here first?

**Tom** (4:15 PM):

Sure. "I wanted to talk about your deadlines."

**Maito** (4:16 PM):

Close, but it sounds like a verdict. Try: "I want to understand what happened with the last three deadlines." It invites an answer. Then give the dates.

## How to set it up

When you ask Coach managers on hard conversations

Set up

Nothing to set up. Ask in Slack or by email whenever you need it.

## What it won't do

Maito helps you prepare. It does not give legal advice, and cases involving discipline, health or discrimination belong with HR.

## Questions

### Does it use our own guidelines?

Yes. Share your feedback guide and Maito follows it instead of generic advice.

### Is the conversation private?

A manager can email the workspace address or ask in a Slack thread. Maito only reads a thread after it is mentioned there.

### Does it talk to the employee?

No. It prepares the manager, and the manager has the conversation.

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-   [Write a job description Get a clear job post from a few notes and similar past roles. People and HR · When you ask Works with Slack, Email.](https://maito.app/workflows/write-a-job-description)
-   [Screen applications against the role Get a short summary of each applicant against what the role needs. People and HR · When something happens Works with Slack, Email.](https://maito.app/workflows/screen-applications-against-the-role)
-   [Prepare interview kits Interviewers get the CV summary, questions and scorecard before the interview. People and HR · When something happens Works with Google Calendar, Microsoft 365.](https://maito.app/workflows/prepare-interview-kits)
-   [Collect interview feedback Chase interviewers for scorecards and summarize them for the debrief. People and HR · On a schedule Works with Slack, Email.](https://maito.app/workflows/collect-interview-feedback)

[See all workflows](https://maito.app/workflows)

## Put your AI teammate to work.

Set it up in minutes. Start with this one, and let it earn the next one.

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