You found the Career Conversation Cheat Sheet🪂

For every manager who quietly dreads the 1:1 where someone asks, "so, what's next for me here?"

Three reasons career conversations don't happen

It's not because you don't care. It's because every time HR says "have more career conversations", nobody explains how to start one inside the 30 minutes you actually have. Let's fix that.

You think you need a 90-minute meeting

You don't. The best career conversations are continual rather than a one-and-done. The big formal version is what everyone is scared of. Reclaim the opportunity to have smaller conversations often. A great place to start? Ask them what their goals are, and help them think through the skills and tasks required for the role. Now they have a map.

You think you need to know all the options

You don't. Asking better questions does more than listing roles. You're not their career oracle - you're the person who helps them notice what they want.

You think "we don't have that role" ends it.

It doesn't. It just means you're finally in a real conversation. Most growth happens in roles that don't exist yet - or in skills they can build inside the role they have today.

Three questions that turn any 1:1 into a career conversation

Steal these. Drop one into the last 10 minutes of any 1:1 this week. No prep required, the questions do the heavy lifting.

"What part of your work this month made you lose track of time?"

Why it works

Surfaces real motivation without making them articulate a five-year plan. You'll learn more about what they actually want from this question than from any annual development form.

"If you had 10% more of your time for something - what would it be?"

Why it works

Opens up stretch projects, gigs, or volunteer assignments without anyone having to mention "promotion." Most growth opportunities live in this answer, not in a job description.

"What's one skill you'd want to be known for in two years?"

Why it works

Lets you have a development conversation that doesn't require a specific role to attach to. Now you have a target. Everything else - mentors, courses, stretch work - can ladder back to it.

Three things you can do this week

Monday

Steal 10 minutes.

End one 1:1 this week with one of the three questions above. Just one. Don't over-prep. See what happens.

Wednesday

Recall what they said last time.

Write down what each of your reports said last time about what they want next. If you can't remember three of them, that's where your reading needs to start.

Friday

Send one quick note.

Slack or Teams one report: "Saw you mentioned X - want to chat about how to get more of that?" Five seconds of work. Massive signal.

We think every manager deserves backup on the hardest part of the job.

You're running 1:1s, hitting quarterly targets, doing performance reviews, and somehow you're also expected to be everyone's career coach. That's a lot. We're building tools that meet you in the flow of work - so career conversations become the easy part of being a manager, not the dreaded one.

No form to fill out for finding this page. Decode the hype, send to the next person about to sit through an AI careers demo, and keep hunting.