An informational interview is a conversation to understand someone’s work, not a disguised demand for a job. Ask about tasks, skills and trade-offs that help you make a better career decision. Respect the person’s time and avoid requesting confidential information.
Choose questions you cannot answer from a public job description alone. The examples below are useful for Singapore jobseekers and career switchers, but one person’s experience should not be treated as the entire market or every employer’s practice.
1. What does a typical piece of work involve?
Ask the person to describe a non-confidential task from start to finish. This reveals the work more clearly than a broad question about whether the career is interesting. Listen for inputs, decisions, collaborators and outputs.
Follow up with: “Which part takes more judgement than outsiders expect?” Avoid asking for private customer cases or internal documents. If the person cannot share a specific example, invite a general description. Your goal is to understand the work, not collect proprietary material for an application.
2. Which skills matter most at the beginning?
Ask what a newcomer needs to do reliably and which skills develop with experience. This can help you distinguish entry requirements from advanced responsibilities. Compare the answer with actual job descriptions rather than treating it as a universal rule.
A useful follow-up is: “What would be a credible way for a beginner to practise that skill?” Do not assume a recommended course guarantees employment. The person’s suggestion is one perspective to evaluate against your situation, resources and the requirements of relevant roles.
3. What commonly surprises new joiners?
Invite a realistic discussion of less visible responsibilities, constraints or working patterns. A role may involve more documentation, coordination or review than its public description suggests.
Ask neutrally rather than fishing for complaints about the employer. “What took you time to adjust to?” is more useful than “What is wrong with the company?” Respect any boundary around personal experience. Use the answer to form better questions for future interviews, not to repeat unverified criticism as fact.
4. How is good work recognised?
Ask how someone knows they are doing the job well in that person’s context. Listen for quality, reliability, collaboration and other relevant outcomes rather than assuming every role is measured only by volume.
Clarify whether the answer describes a formal process or personal observation. Do not request private performance records. The insight can help you identify examples from your own experience, but it does not establish the evaluation criteria of another organisation where you may later apply.
5. Which adjacent backgrounds can be relevant?
For a career switch, describe one genuine experience and ask where it connects and where it falls short. This makes the conversation specific without asking the person to assess your entire employability.
Hypothetical wording: “I have experience handling service requests. Which parts might help in operations coordination, and what would I still need to learn?” Accept that transferable skills do not remove every gap. Avoid treating an encouraging response as a guarantee that a hiring manager will reach the same view.
6. What would you investigate before choosing this path?
Ask what the person would check if they were deciding today. They may point to the daily work, training commitment, role variation or practical working arrangements. Focus on the reasoning behind the suggestion.
Do not ask them to make your decision for you. Compare their advice with other informed perspectives and current vacancies. If they recommend a paid course or service, assess it independently; a friendly recommendation is not evidence of suitability, quality or a hiring outcome.
7. What is a sensible next learning step?
Close by asking for a practical next step, such as reading a public resource, trying a fictional exercise or speaking to someone in a different type of role. Keep the request proportionate to the conversation.
Thank the person for specific information that helped you. Ask permission before using their name in an application or requesting an introduction. Do not assume that answering career questions means they have agreed to refer you, review extensive work or provide ongoing coaching.
A respectful request
Hypothetical wording: “I am exploring a move into operations coordination and would value a short conversation about the daily work. I am not asking about vacancies or confidential information. If you are available, I would like to ask a few questions at a time convenient for you.” Adapt the length and channel to your relationship.
Turn the conversation into useful notes
Record what you learned, what was specific to that person’s workplace and what still needs checking. Identify one action you can take. Do not quote the person publicly or attribute claims without permission.
Should I send my CV immediately?
Only if relevant and welcome. Start with the agreed purpose rather than converting the conversation into an unsolicited application review.
How many conversations are enough?
There is no fixed number. Seek enough varied information to understand important uncertainties without treating anecdotes as market statistics.
For in-person employer conversations, see career fair conversation starters.
