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 10 turns

Setting a boundary with a coworker

A friendly coworker keeps dumping last-minute work on you and messaging after hours. Set a clear boundary without damaging the relationship.

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

Who will I be talking to?

Riley Park. The AI plays a easy 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?

Name the pattern specifically, say clearly what you will and will not do going forward, hold the line when deflected, and offer a constructive alternative so the relationship stays good.

What will the AI ask me?

It opens with: Hey! Perfect timing. So I know it's almost 5, but could you take a quick look at the deck before my 9am? It's basically done, it just needs your magic. You're a lifesaver! From there it follows your answers with realistic follow-ups, so no two runs are the same. The conversation lasts up to 10 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.

Clarity of the boundary 30%

States specifically what will change (no same-day asks, no after-hours messages) without hedging.
Holding the line 25%

Does not cave to the deflection or the immediate new ask.
Tone 20%

Warm and direct, not apologetic, not aggressive.
Constructive alternative 15%

Offers a workable way to collaborate (planning ahead, a shared queue, a set time).
Repairing the relationship 10%

Acknowledges the coworker's feelings and affirms the relationship.

How hard is it?

Difficulty 2 of 5 (easy). Expect patience and gentle follow-ups; good for a first run. 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.