How to Use AI to Prepare for a Hard Conversation With Your Boss
Asking for a raise, pushing back on feedback, raising a concern — AI can help you think through what you actually want to say before the conversation starts.
No jargon. No panic. No hype. Just thoughtful writing for real professionals who want to understand what AI actually means for their work and life.
Three articles carefully chosen as the best starting point for where you are right now.
Asking for a raise, pushing back on feedback, raising a concern — AI can help you think through what you actually want to say before the conversation starts.
AI can help you write a cover letter — but the generic version it produces by default won’t get you hired. Here’s how to use it in a way that actually works.
You don’t need a lawyer for every document you’re handed. Here’s how to use AI to understand contracts, leases, and legal language before you sign.
Performance reviews are painful to write. AI can help you get past the blank page, find the right words, and say what you actually mean — without sounding generic.
Salary negotiation is uncomfortable for most people. AI can help you research, rehearse, and walk in more prepared — without making you sound like you practiced in a mirror.
When you need to understand something unfamiliar quickly — a new industry, a technical concept, a field outside your expertise — AI is one of the best tools you have.
One of AI’s most underused strengths: translating complex, jargon-heavy material into something anyone can understand. Here’s how to use it well.
Budgets, medical bills, reports, spreadsheets — AI is surprisingly good at explaining what the numbers actually mean and what you should do about them.
AI won’t have the conversation for you — but it can help you think it through before you walk in. Here’s how to use it to prepare without over-scripting.
Giving hard feedback is one of the most avoided things in professional life. AI can help you think it through and find the words — without making it sound like a performance review template.
AI can make the practical parts of job searching faster and less painful. Here’s how to use it without letting it sand down everything that makes you stand out.
AI is a surprisingly good planning partner — not because it knows your situation, but because it asks the right questions and structures what you already know.
Contracts, terms of service, lease agreements, insurance policies — AI can translate the ones designed to be unreadable. Here’s how.
Email overload is real. AI tools can genuinely help — if you know which parts of the problem they can actually solve.
AI is genuinely good at turning long content into something manageable. Here’s how to use it to get the signal out of anything without losing what matters.
AI can genuinely help you structure, write, and refine a presentation — if you know how to direct it. Here’s how to use it without letting it flatten your ideas.
AI won’t make your hard decisions for you — but it can help you think more clearly. Here’s how to use it well when the stakes are real.
AI can give you surprisingly useful feedback on your work — if you ask the right way. Here’s how to get critiques that are actually worth something.
Most people use AI for tasks. The professionals pulling ahead are using it to think about their trajectory, map their gaps, and prepare for the conversations that actually change their career.
Rehearsing a hard conversation with AI isn't strange β it's practical. Here's how to use ChatGPT or Claude to prepare for the conversations you've been putting off.
You're not cheating your kids by using AI. You're showing them how to think alongside powerful tools β and that's exactly what they'll need.
AI won't get you the job β but it can make sure you walk in more prepared than anyone else in the room. Here's the exact workflow to use.
When work piles up and you don't know where to start, AI can actually help β but only if you know where to point it. Here's a practical guide for the genuinely overwhelmed.
Small business owners are hearing a lot about AI. Here's an honest look at where it saves real time, where it falls short, and how to start without the overwhelm.
AI can accelerate research dramatically β or lead you confidently in the wrong direction. The difference comes down to how you use it.
AI writing tools can make you faster and sharper at work β or they can make your writing generic and your thinking lazy. The difference is how you use them.
AI tools don’t remember your last conversation. Here’s a plain-language explanation of why — and practical ways to work around it so you stop repeating yourself.
A step-by-step method for using Claude or ChatGPT to actually understand an unfamiliar topic β not just get a summary, but genuinely learn it.
Most people walk into meetings underprepared. AI can change that in ten minutes. A practical approach for sales calls, job interviews, and difficult conversations.
AI can help you write faster, clearer emails β but only if you use it right. Here's what actually works.
An honest map of where AI helps, where it falls short, and how to tell the difference before it costs you time or trust.
That knot in your stomach when you read another AI headline? It's not weakness β it's your brain telling you something important. Here's how to listen to it wisely.
The jobs of the future won't belong to AI. They'll belong to the humans who can work alongside it. Here's what that actually looks like β and how to get there.
Forget learning everything. You need five tools, used consistently. Here are the ones that have the biggest impact for the least learning curve.
The shift isn't about technology. It's about perspective. Here's how to stop seeing AI as a threat and start using it as the tireless assistant it actually is.
The pressure to "get technical" with AI is growing louder. Here's why business professionals should lean in β but not necessarily all the way.
Tom is writing every week. Subscribe to the newsletter to be first to know when new articles drop β and get them delivered directly to your inbox.
Small business owners are hearing a lot about AI. Here's an honest look at where it saves real time, where it falls short, and how to start without the overwhelm.
AI can accelerate research dramatically β or lead you confidently in the wrong direction. The difference comes down to how you use it.
AI writing tools can make you faster and sharper at work β or they can make your writing generic and your thinking lazy. The difference is how you use them.
AI can help you write faster, clearer emails β but only if you use it right. Here's what actually works.
Before you can move forward, it helps to understand where you actually stand. An honest, gentle look at how we develop tech anxiety β and how we shed it.
Notify me when published βA practical, step-by-step plan for professionals who want to systematically build their AI fluency β without quitting their day job or going back to school.
Notify me when published βThe single most valuable AI skill isn't technical β it's conversational. Learn the simple framework that unlocks dramatically better results from any AI tool.
Notify me when published β