Episode 96 - How to have career conversations that help episode artwork

EPISODE · Nov 19, 2025 · 13 MIN

Episode 96 - How to have career conversations that help

from Career Espresso

How to have career conversations that helpYou schedule a career conversation and both of you immediately feel that slight dread. You ask where they see themselves in five years. They give a polished answer that means nothing. You both tick the box and move on. Nothing actually changes. This episode of Career Espresso is about having career conversations that actually help people—not as a performance review exercise or a tick-box requirement, but as a genuine conversation about what's possible and what you can do to support them.What you'll discoverWhy career conversations feel awkward or surface-level for most leaders What people actually need from these conversations (it's not "where do you see yourself in five years?") How to ask questions that open up real conversation instead of extracting rehearsed answers What to do when someone doesn't know what they want How to support growth without making promises you can't keep Perfect for women leaders who want these conversations to feel useful instead of awkward.Want more support with real-world leadership challenges? Head to How to Build a Leader on Substack for in-depth guides and scripts.Never miss an episode. Sign up for the weekly Espresso Brief email and get each episode with quick takeaways in your inbox.Get the full episode transcript Hosted on Acast. See acast.com/privacy for more information.

How to have career conversations that helpYou schedule a career conversation and both of you immediately feel that slight dread. You ask where they see themselves in five years. They give a polished answer that means nothing. You both tick the box and move on. Nothing actually changes. This episode of Career Espresso is about having career conversations that actually help people—not as a performance review exercise or a tick-box requirement, but as a genuine conversation about what's possible and what you can do to support them.What you'll discoverWhy career conversations feel awkward or surface-level for most leaders What people actually need from these conversations (it's not "where do you see yourself in five years?") How to ask questions that open up real conversation instead of extracting rehearsed answers What to do when someone doesn't know what they want How to support growth without making promises you can't keep Perfect for women leaders who want these conversations to feel useful instead of awkward.Want more support with real-world leadership challenges? Head to How to Build a Leader on Substack for in-depth guides and scripts.Never miss an episode. Sign up for the weekly Espresso Brief email and get each episode with quick takeaways in your inbox.Get the full episode transcript Hosted on Acast. See acast.com/privacy for more information.

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Episode 96 - How to have career conversations that help

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How long is this episode of Career Espresso?

This episode is 13 minutes long.

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This episode was published on November 19, 2025.

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How to have career conversations that helpYou schedule a career conversation and both of you immediately feel that slight dread. You ask where they see themselves in five years. They give a polished answer that means nothing. You both tick the box...

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