How to Start Career Conversations When You're Too Scared to Ask (Scripts Included)

How to Start Career Conversations When You're Too Scared to Ask (Scripts Included)

There were many times in my early career that I wished I had spoken up to my boss about how I wanted to develop my career. But I didn't.

As a result, my career history is littered with a bunch of 'should have,' 'could have,' 'would haves'—regrets that could have been easily resolved had I known how to go about initiating a career conversation.

I'm pretty sure I fumbled that whole conversation, but through that chance I took, I changed the trajectory of my career.

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How to Master Career Conversations When You Need to Feel in Control

How to Master Career Conversations When You Need to Feel in Control

When you're wired to seek control, career conversations can feel like a double-edged sword—equal parts exciting and nerve-wracking. You want things to go according to plan, but as we know, plans can change.

Wanting control doesn't mean being inflexible or resistant to change. It's really about seeking clarity, accountability, and measurable progress in your career journey.

So how do you navigate career conversations when things don't go as expected? It takes preparation, flexibility, and resilience.

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When Your Career Feels Stuck (But You're Still Moving): A Guide to Recognising and Breaking Career Drift
Career Development Ruth Song Career Development Ruth Song

When Your Career Feels Stuck (But You're Still Moving): A Guide to Recognising and Breaking Career Drift

Career drift is what happens when you're no longer steering your career—but you're still moving. It doesn't come from laziness or lack of ambition. In fact, it often affects high performers most severely.

You become so good at what you do that everyone depends on you for it. You're the go-to person, the reliable one, the problem-solver. But while you're busy being competent, time passes. Opportunities go to others.

The cruel irony? The better you are at your current role, the harder it becomes to move beyond it.

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