Conversations by situation
Difficult conversations at work and in life: find your situation
Pick the conversation you are facing. Each one comes with tips and example phrases, a description of the other person and a way to practice it by voice or chat before it happens for real.
Conversations by situation
Talking to your boss
How to tell your boss something that is hard to say
Talking to employees
How to have a difficult conversation with an employee
Leading a team
Leadership conversations: how to handle them calmly and clearly
- My first conversation with a new team
- I talk to a team member caught in a conflict
- I delegate a task to an experienced colleague
- I turn down vacation on the requested dates
- I tell a team member about changes at the company
- I talk to someone who keeps interrupting others
- I give feedback to my boss
- I talk to a team member with more experience than me
- I run a one-on-one with a disengaged team member
- I talk to a colleague who also wanted the promotion
- I say no to a raise for a strong employee
Interviews and career
Job interviews and career conversations: how to prepare
- I am going to a job interview
- I am answering “tell me about yourself”
- I am answering the weaknesses question
- I am explaining a gap in my CV
- I am changing careers and going to an interview
- I am on a phone screen with a recruiter
- I am asking my former boss for a reference
- I am returning to work after parental leave
- I am asking my boss to work remotely
- I am asking for flexible working hours
- I am telling my boss I am burned out
Sales and customers
How to talk to customers when money and decisions are on the line
- I am calling a prospect who does not know me
- I am following up on a proposal
- A client is asking me for a discount
- A client picks up after weeks of silence
- I am offering a client a bigger package
- I am handling an upset guest
- I am saying no to out-of-scope work
- I am discussing a contract renewal
- A client says they are leaving for a competitor
- I am meeting the client’s CEO
- I am telling a client my prices are going up
School and university
Conversations at school and university: teachers, lecturers and supervisors
Everyday situations
How to sort out everyday problems when the other side pushes back
- I ask my neighbor to keep it down
- I ask for my deposit back
- I ask my landlord for a repair
- I negotiate a rent increase
- I talk to my roommate about cleaning
- I return a faulty product to a store
- I deal with an office clerk
- I discuss the estimate with my mechanic
- I cancel my subscription
- I send a dish back at a restaurant
- I talk to my contractor about delays
Health and care
Health conversations: with your doctor and with an aging parent
Relationships
How to have a difficult conversation with your partner
Family
How to talk to your teenager, your child and your parents
Friends
How to talk to a friend about what is hurting the friendship
Assertiveness
Assertiveness in practice: how to say no and ask for what is yours
Frequently asked questions
How do I prepare for a difficult conversation?
Write down what you want to achieve and the first sentence you will open with. Think about what the other person will hear and what they care about. Then say it out loud, ideally to someone who answers back, because a plan in your head tends to fall apart at the first objection.
How is practicing with AI different from reading advice?
Advice tells you what to say. Practice shows you what you actually say when the other person interrupts, pushes back or goes quiet. The AI plays someone with their own goals and a hidden motive, and the report points to the moments that helped or hurt.
Can I practice a situation that is not on the list?
Yes. The list covers the most common situations, but in the builder you can describe your own in a few sentences: who is talking to whom, what is at stake and what makes it hard. The description becomes a scenario with a counterpart, goals and report criteria.
Do these conversations replace therapy, legal or medical advice?
No. This is practice for words and reactions. Pages about rights, health or personal matters include a note on where to find professional help. Crisis topics are deliberately left out.
Pick a conversation and try it out loud.
Practice any situation with an AI counterpart and see in the report which sentences worked and which are worth saying differently.