Difficult Conversations at Work
Hard workplace conversations — firing, feedback, raises, conflicts — are unavoidable. The difference between handling them well and poorly comes down to preparation. Get the frameworks, scripts, and practice you need to navigate them with confidence.
Workplace Conversation Guides
Step-by-step guides with exact scripts for the hardest professional conversations.
How to Fire Someone
Terminating an employee is one of the hardest things a manager does. Get exact scripts for the opening, handling reactions, and logistics.
Read the guide →How to Have Difficult Conversations With Your Boss
Whether it's a raise request, workload issue, or disagreement — learn how to approach your manager without damaging the relationship.
Read the guide →How to Ask for a Raise or Promotion
Most people never ask — or ask badly. Get scripts for making a compelling case based on value, not need.
Read the guide →How to Give Constructive Feedback
Feedback is a gift only if delivered well. Learn how to give honest, actionable feedback without being hurtful.
Read the guide →What to Say When Someone Takes Credit for Your Work
Having your work claimed by someone else is infuriating. Here's how to address it directly without blowing up relationships.
Read the guide →How to Ask for a Mental Health Day
Request time off for your mental health without oversharing or hurting your career.
Read the guide →A Framework for Hard Workplace Conversations
Prepare the business case
Work conversations succeed when framed around business value, not personal feelings. Document specifics: revenue impact, timelines, market data.
Open with clarity
Get to the point in the first 30 seconds. The other person deserves to know what the conversation is about upfront.
Listen, then respond
Difficult conversations are two-way. Hear the other person's perspective before defending your position.
End with clear next steps
Don't leave without agreement on what happens next. Who does what, by when.
Frequently Asked Questions
What counts as a difficult conversation at work?
Difficult workplace conversations include performance feedback, termination discussions, salary negotiations, addressing conflicts with colleagues, and communicating problems to your manager. The common thread: high stakes, emotions, and the risk of damaging a professional relationship.
How do you start a difficult conversation with your boss?
Start by requesting dedicated time rather than springing it on them. Open with context: 'I'd like to discuss [topic] and get your perspective.' Frame it as collaborative problem-solving rather than a complaint or demand.
What should you not say when firing someone?
Avoid phrases like 'This is hard for me too,' 'You'll land on your feet,' or 'This isn't personal.' These center your discomfort or dismiss the employee's reality. Be direct, respectful, and focus on logistics once the decision is clear.
How do I ask for a raise without seeming entitled?
Build a business case, not a personal one. Document your impact, research market rates, and present it as: 'Here's the value I've created, here's what the market shows, and here's what I'm proposing.' The key is data, not feelings.
Can practicing with AI actually help with workplace conversations?
Yes. Practicing with an AI coach lets you rehearse different scenarios, test your wording, and build confidence before the real conversation. You can explore how to handle objections, adjust your tone, and find language that feels natural to you.
Practice Before the Real Conversation
The best preparation is practice. Use our AI coach to rehearse your difficult workplace conversation — test different approaches, refine your wording, and build confidence before you walk into the room.