Career Advice / Hard Conversations at Work

How to Have Hard Conversations at Work

The conversation you’re avoiding is usually the one your career is waiting on.

Asking for the raise. Pushing back on your boss. Telling someone the truth. These articles are about what to say, when to say less, and what it costs you to stay quiet.

The tool for thisHard Conversations Script LibraryTwelve conversations scripted word for word, with comebacks and recovery lines. Open it

42 articles on hard conversations at work

June 6, 2026

The Secret Language of Corporate America

Early in his career, Scott realized working in a corporate environment is a lot like learning a second language, except nobody tells you the language exists. “Let’s circle back” rarely means a follow-up is coming, and “interesting idea” usually means the idea is dead on arrival. Scott on why corporate jargon exists, how fluency sneaks up on you, and why careers are built on reading the room and understanding what is not being said.

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May 23, 2026

The Most Honest Version Keeps Pulling Us in One Direction

A Medium told Scott yesterday to lean into what feels natural and stop fighting what's coming his way. He laughed, then she pointed out 25 clients isn't a side hustle, it's a business. Scott on three years of coaching, the people who've shown up since day one, and why the feeling of being stuck usually has less to do with talent and more to do with honesty.

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