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What should you ask to understand someone’s work beyond their job title?

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The Weekend Club · Practical editorial guide · Updated 2026-09-12

Ask about a recent task, how time is divided, and the trade-offs behind the work. Use concrete experiences to understand the role rather than asking one person to judge an entire industry. Treat each conversation as a situated account that needs comparison.

Evidence and scope

Herminia Ibarra describes exploring possible career identities through experience and small experiments. This is a research-informed framework, not a randomized test of this worksheet or a promise of career results.

Start with a recent week

Ask what took most of their time, if they are comfortable sharing. Do not request customer names, internal figures, or confidential projects. General working rhythms can still be informative.

Separate kinds of work

Ask whether independent work, coordination, or unexpected problems take the largest share of attention. Exact percentages are unnecessary. A creative-looking title may involve substantial preparation and communication.

Explore a trade-off

Try asking what difficult task comes with their favorite part of the job. Let them use an example they can share. You are learning about conditions, not collecting complaints or company gossip.

Check your interpretation and seek another sample

Summarize what changed your understanding and invite correction. Then compare a different company size or career stage. Ibarra’s work offers a reference for exploring possible careers through experience; this question list is an editorial design.

A worksheet you can use

My initial picture
I thought the role mostly involved ____.
Actual example
A recent task involved ____.
Context
This reflects one person at ____.
Another source
I still need to check ____.

Common questions

Can I ask about salary?

Check whether they are willing to discuss it and allow them to skip the topic. Use appropriately documented public data for market comparisons.

How do I avoid sounding like an interviewer?

Choose one or two questions, share your perspective, and leave room for other subjects.

Sources and reading

Keep exploring

Explore the life possibilities library

Prepared by The Weekend Club with AI assistance. Examples and worksheets are editorial suggestions. Source authors have not personally reviewed or endorsed this page.