17 | How to Use AI to Prepare for a Raise, Promotion, or Hard Conversation at Work

You know you deserve more. But walking into that conversation without preparation is how working moms get passed over — not because they're not ready, but because the prep feels like one more full-time job on top of the three they're already working. In this episode, I walk you through how to use AI to build an airtight case for your raise, promotion, or difficult workplace conversation — and how to rehearse it before you ever walk into the room. No career coach. No spending your weekends drafting talking points. Just a sequence of prompts that turns scattered accomplishments into a persuasive case and gives you the words before you need them. You'll learn how to use AI to build a brag document that reframes your accomplishments in the language decision-makers actually respond to, how to prompt Claude to anticipate your manager's most likely objections and prepare calm, professional responses for each one, how to role-play the actual conversation with AI so you get to stumble in private instead of in the room, the boundary-setting prompt that turns "I'm drowning" into a structural case for change, and how to build a follow-up system — recap email, 30-day check-in, 60-day escalation — so the conversation doesn't die after one meeting. Plus, in this week's Ask AI segment, I take a question every working mom has asked — "How do I ask for a raise without sounding entitled?" — and reframe it into a negotiation prep prompt that builds the case around impact and market data, not feelings. What's mentioned in this episode: 🎯 Free Download: The Career Conversation Prep Kit — every prompt from this episode, three ready-to-use follow-up email templates, and a conversation tracker: lakeshaholloway.com/career 📝 Take the AI Confidence Quiz: aiconfidenceblueprint.com/workingmomquiz 👨‍👩‍👧‍👦 Parent AI Readiness Scorecard: aiconfidenceblueprint.com/scorecard 🎙️ Browse all episodes: lakeshaholloway.com/podcast If this episode helped you, share it with one working mom who's been putting off a hard conversation. And leave a review — it helps other moms find the show.