Have you ever waited for the right moment to ask for a raise, and the right moment never came? Wingspan Founder Christina Wing joined host Lauren McGoodwin on The Career Contessa Podcast to talk about seven workplace conversations people tend to put off, and why waiting usually costs more than speaking up. Christina has written a book on these topics, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them.
Christina grew up in a family business and couldn’t wait to get away from it. After working in banking, starting a dot-com, and running a family office, she was getting ready to join her father in business when he died suddenly. She was left making big decisions about things they had never discussed, and that experience led to Unspeakable. As she put it, avoiding a conversation “simply makes decisions for us.”
Here are a few highlights.
Asking for more
Don’t make your boss guess what you want. Come with facts, ask what it will take to get a raise or promotion, and start early. If raises are decided in December, bring it up in January.
Owning mistakes
Apologize quickly and skip the “but.” Christina starts her Monday team calls by asking for everyone’s biggest mistake from the week before, and she always goes first.
Job security and AI
If you’re worried AI could do parts of your job, don’t hide. Figure out which parts, then go to your manager with ideas for what you could take on instead.
She also gets into how much to share about your personal life at work, how to talk about ambition, why you should stop comparing salaries, and the one topic she thinks every team should be discussing right now.
“Success is not the conversation going well. Success is beginning the conversation.”
In the full episode, Christina shares the phrases she uses to open a difficult conversation, and the one question she wishes people would stop asking their boss. Give it a listen below.
