How to Have a Difficult Conversation With an Employee — Without Making It Worse

This isn't a chatbot that hands you a script. It's an advisor that asks about your situation first — then tells you exactly what to say and how to handle any reaction.

Difficult Conversations Advisor

For the conversations you've been putting off

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You know the conversation needs to happen. Maybe someone's behavior is affecting the whole team. Maybe you need to deliver feedback you've been putting off for weeks now. You're lying awake rehearsing what to say — and dreading every version.

69% of managers say they're uncomfortable communicating with their employees. More than 80% are holding back at least one difficult conversation right now.

That's exactly what the Difficult Conversations Advisor helps with. It asks about your specific situation and gives you tailored guidance — not generic tips you could find in any management article.

Get Help Right Now

It's 11 PM and you have the conversation tomorrow morning? We're here. No waiting for appointments, no approval from your company, no scheduling weeks out.

Your Situation, Not Generic Tips

Generic AI gives you a script. This advisor asks what you've already tried, who's involved, and what's at stake — then builds a plan from there.

No Judgment, Ever

Unlike asking your boss or colleague, there's zero risk of looking incompetent. Your conversations are private — never shared with your company, never used to train AI.

Notice what happens first

Before giving advice, the advisor asks the kind of questions an experienced manager would ask. That's what makes the guidance specific to you — not a template.

I need to tell a strong performer that their attitude in meetings is shutting other people down — but they're one of my best performers. I don't want to diminish what they contribute.
The advisor asks before advising
Let's make sure we approach this right. Can you give me a specific example of when this happened recently? What did they say or do, and how did others react?
Yesterday in our sprint planning, Sarah proposed a different approach to our API design. Before he finished explaining, he jumped in with "That won't work because..." and listed three problems. Sarah just went quiet and didn't speak up for the rest of the meeting.
Specific script, not generic advice
That's the perfect example to reference. Here's how to open: "I want to talk about something from yesterday's meeting. I'm bringing it up because your input matters to this team — and I think something is getting in the way of people hearing it." Then name the behavior: "When Sarah was explaining her idea, you jumped in before she finished. She went quiet for the rest of the meeting." Then pause and let them respond.

This advice was for one scenario. Your situation is different.

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How It Works

1

Describe your situation

Share what's happening — who's involved, what's been said, what you've already tried. The advisor asks follow-up questions to understand the nuance.

2

Get a tailored plan

Receive specific opening phrases, talking points for the middle of the conversation, and a strategy for handling likely reactions.

3

Walk in prepared

Go into the conversation knowing exactly what to say and how to say it. The kind of preparation that normally takes a $300/hour coaching session.

Encrypted conversations
Available 24/7 — even at 11 PM
Specialized, not general-purpose
Never used to train AI
Start Your Free Trial →

14 days free · No credit card required

Common Questions

Have a difficult conversation coming up?

Describe the situation and get a specific plan — what to say, how to start, and how to handle any reaction.

Or Start Your Free Trial →

14 days free · No credit card required