How do I prepare for a difficult conversation at work?

Decide the one outcome you want, rehearse your opening line, and practice staying calm when the other person gets defensive. A roleplay lets you try that before it counts.

How do I ask for a raise without sounding entitled?

Lead with specific results, tie them to a market number, and ask a clear question. The salary negotiation scenario scores you on evidence, tone, and whether you hold your position under pushback.

How do I give negative feedback to someone kindly?

Describe the specific behaviour, its impact, and what you need instead, then stop talking and listen. The feedback scenario rewards clarity without harshness and checking for understanding.

What if the other person gets angry during the conversation?

Stay on the issue, lower your pace, and acknowledge the emotion without taking the bait. Higher difficulty levels in these scenarios make the persona more defensive so you can practice exactly that.

Can practicing a conversation with an AI really help?

Rehearsal reduces the freeze response. Saying the hard sentence three times to a realistic counterpart makes it far easier to say once to a real person.

Hard conversations up to 12 turns

Giving hard feedback

A direct report keeps missing deadlines and quality has slipped. Deliver clear, kind feedback, get to the cause, and agree on a plan.

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No account needed · First session free today · Instant scored feedback

Who will I be talking to?

Sam Okafor. The AI plays a hard counterpart who stays in character for the whole conversation, asks one question at a time, and pushes back when your answers are vague. It never coaches you mid-conversation; feedback comes at the end.

What is the goal of this scenario?

State the problem with specific examples and impact, avoid character judgments, ask open questions to understand the cause, respond with empathy when the real issue surfaces, and agree on concrete next steps and a check-in.

What will the AI ask me?

It opens with: Hey, you wanted to talk? I have a feeling I know what this is about. Before you start, I want to say the API team was late on their side too, so it wasn't all on me. From there it follows your answers with realistic follow-ups, so no two runs are the same. The conversation lasts up to 12 of your turns, or you can end it early to get scored.

How is my score calculated?

You get a score out of 10 for each of these criteria, and an overall score weighted as shown. Each criterion comes with a one-line note on what you did and what to change.

Specific, behavior-based feedback 25%

Names concrete examples and their impact rather than generalizations or labels.
Curiosity about cause 25%

Asks open questions and listens instead of lecturing; discovers the personal situation.
Empathy with accountability 20%

Responds with care to the disclosure while keeping expectations clear.
Handling defensiveness 15%

Stays calm, does not argue about other teams, redirects to what is in their control.
Concrete plan 15%

Ends with agreed actions, support offered, and a follow-up date.

How hard is it?

Difficulty 4 of 5 (hard). Expect interruptions, skepticism, and demands for evidence. After your first run you can retry at a harder level.

Do I need an account?

No. You can run one free session a day without signing up and see your overall score. A free account unlocks full coaching notes, five scored sessions a month, history, and shareable results.