What Does It Mean to Ask Someone About Their Career — and Why Should You?
It means conducting a structured, time-bounded conversation focused on learning about a field, role, or career path rather than pitching yourself for a job.
According to UC Berkeley Career Engagement, an informational interview is “an informal conversation with a person working in a career field that interests you” whose purpose is explicitly not to find job openings but to explore the field and gain insider knowledge.
Why bother? Because most people operate on incomplete information about careers. A 2023 NACE survey found that only 26.1% of graduating seniors strongly agreed they felt “career ready,” even though 87.3% had completed at least one internship. The gap between experience and clarity is real.
Career conversations close that gap. A 2022 Gallup and Lumina Foundation study showed that adults who had help from a mentor or advisor who talked with them about careers were 67% confident in their career prospects, compared with 44% of those without such guidance. And according to LinkedIn Talent Solutions, candidates referred by someone at a company are four times more likely to be hired than cold applicants. Informational conversations are one of the most common ways those referral relationships begin.
When Should You Ask Career Questions? Key Situations That Call for Them
Any moment of transition, uncertainty, or ambition is the right time, but job changes, education decisions, performance reviews, and networking events carry the highest stakes.
Before a job change. The median tenure for U.S. workers ages 25 to 34 is just 2.8 years, according to the BLS Employee Tenure Summary. With moves happening this frequently, asking career questions before each transition helps you avoid mismatches.
Before investing in education or training. BLS Employment Projections for 2024–2034 show that occupations requiring a master’s degree or higher are projected to grow faster on average than those requiring only a high school diploma. But not all credentials pay off equally. Talking to someone already in the role can reveal which certifications actually matter versus which ones collect dust.
During performance reviews. A 2023 Gallup study found that only 21% of employees strongly agree they’ve had a meaningful career conversation with their manager in the last six months. Those who did were 3.5 times more likely to be engaged. Reviews are not just backward-looking evaluations; they’re prime opportunities to ask forward-looking questions.
At networking events and career fairs. A 2024 ZipRecruiter survey reported that over 25% of job seekers found their most recent role through networking or a referral. The questions you ask at these events determine whether you leave with a business card or a genuine connection.
The 10 Best Questions to Ask Someone About Their Career
The strongest questions extract specific, actionable intelligence about entry paths, daily realities, skill demands, compensation, and career progression in any field.
| # | Question | What the Answer Reveals |
|---|---|---|
| 1 | ”How did you get into this field?” | Entry paths, whether formal credentials were necessary, and lucky breaks vs. planned moves |
| 2 | ”What does a typical day or week actually look like?” | Real task breakdown (meetings vs. deep work vs. admin), pace, and autonomy |
| 3 | ”What skills matter most for success in your role?” | Skill gaps you can close before applying; which resume skills to prioritize |
| 4 | ”What surprised you most about this career once you started?” | Hidden downsides, culture realities, and expectations vs. reality |
| 5 | ”How has your role changed in the last few years?” | Industry direction, automation risk, and emerging skill demands |
| 6 | ”What does career progression look like from where you sit?” | Promotion timelines, ceiling risks, and lateral move options |
| 7 | ”What’s a realistic salary range for someone entering this field?” | Compensation norms, total comp structure, and negotiation anchors |
| 8 | ”Who helped you get where you are, and how did you find them?” | Mentorship and sponsorship patterns; how relationships drive advancement |
| 9 | ”If you were starting over today, what would you do differently?” | Regrets that save you time; shortcuts and pitfalls |
| 10 | ”What advice would you give someone preparing to enter this field right now?” | Immediate, actionable next steps tailored to current market conditions |
Why these specific questions? A 2023 Handshake survey found that 60% of college students said their biggest concern about their future career was “not knowing what a typical day will be like.” Questions 1, 2, and 4 directly address that anxiety. Meanwhile, LinkedIn’s 2024 Skills Evolution report notes that skills needed for the average job have changed by about 25% since 2015, making questions 3 and 5 essential for anyone building a forward-looking resume.
Question 7 matters more than ever. According to a 2024 SHRM survey, only 37% of organizations always include pay ranges in job postings. Conversations fill the gap that job ads leave open.
What Do Hiring Managers and Career Experts Say About Informational Interviews?
Hiring managers and career experts overwhelmingly endorse informational interviews as one of the most effective tools for building relationships, gaining clarity, and improving candidacy.
Yale’s Office of Career Strategy calls informational interviewing a “powerful networking tool to learn about career paths and build future relationships.” CUNY Graduate Center goes further, describing it as “the single best way to look for a job.”
Hiring managers benefit too. According to LinkedIn’s Global Talent Trends 2023 report, referrals remain one of the top three sources of quality hires worldwide. Informational interviews are the relationship-building step that makes those referrals possible.
One coaching firm’s rule of thumb, cited by Ivy Exec, estimates that roughly 1 in 12 well-targeted informational interviews can lead to a job offer. But career experts stress that the primary value is clarity and better targeting, not immediate job leads. As UC Berkeley’s career team puts it, the purpose is explicitly “not a job interview.”
Career experts also see these conversations as skill-building for real interviews. Jody Michael Associates highlights that informational interviews help job seekers “polish interviewing skills and gain confidence and poise” while learning how to position themselves and their resume.
How Do Career Conversations Translate Into Real Salary and Job Insights?
Career conversations provide granular, role-specific compensation and job-reality data that job boards and salary aggregators cannot match on their own.
A 2024 Glassdoor economic research briefing found that workers who discuss salary with at least one colleague are about 19% more likely to negotiate a job offer or raise. Among those who negotiated, people who had discussed pay with peers reported securing offers 7 to 8% higher than their initial offer.
Career conversations also help you interpret macro data at a personal level. The BLS Employment Projections for 2024–2034 show that total U.S. employment is expected to grow about 0.3% per year on average, but growth is extremely uneven:
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Nurse practitioners: projected growth of over 40%, with a 2024 median pay of $129,480. Explore the nurse practitioner salary page for more detail.
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Data scientists: projected growth of about 35%, with a 2024 median pay of $112,120.
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Software developers: projected growth of roughly 25%, with a 2024 median pay of $130,160. See software engineer salary data.
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Reporters and correspondents: projected decline of around 14%.
BLS tells you what is growing. A conversation with a data scientist tells you which sub-specialties command the highest pay, which tools hiring managers actually screen for, and whether a data scientist resume should highlight Python or SQL more prominently.
An INSEAD Knowledge article referencing Right Management research found that two-thirds of individual performance drivers are tied to the quality of career conversations with managers. Regular career talks don’t just inform you; they directly influence your trajectory and earnings over time.
Which Questions Work Best in Different Industries?
The best career questions are tailored to each industry’s unique realities, including pace, skill demands, emotional labor, and scheduling patterns.
In tech, ask about projects, iteration speed, and learning cadence. O*NET data for Software Developers (15-1252.00) shows very high importance ratings for problem solving (91/100) and teamwork (88/100). Try: “What kinds of projects are you responsible for in a typical quarter?” and “How do you keep your skills current when tools change so quickly?” These questions matter because, as LinkedIn’s data shows, skills in tech roles shift faster than in almost any other field.
In healthcare, ask about shift patterns, patient loads, and emotional demands. O*NET scores registered nurses at 86/100 for “Exposed to Disease or Infections” and 81/100 for “Time Pressure.” A question like “How much of your time is direct patient care versus documentation?” reveals realities that a registered nurse resume alone won’t capture. BLS projects healthcare occupations overall to grow 9 to 10% from 2024 to 2034, adding roughly 1.5 to 2 million jobs.
In finance and consulting, ask about deal cycles, billable hours, and busy seasons. Try: “What does a typical deal or client engagement cycle look like?” and “What are your hours during the busiest periods?” If you’re building an investment banker resume, knowing that 60 to 80 hour weeks during deal closings are standard changes how you frame your stamina and commitment.
In hospitality and retail, ask about volume, schedule variability, and customer conflict. “How far in advance do you know your shifts?” and “How do you handle difficult customers, and how often does that happen?” surface the emotional labor that job descriptions rarely mention.
How Do You Turn a Career Conversation Into Actionable Next Steps?
Write down specific goals within 24 hours, then build a structured development plan that connects conversation insights to concrete actions and timelines.
According to LinkedIn’s 2024 Workforce Report, professionals who articulate specific career goals are 45% more likely to receive mentorship and sponsorship opportunities than those who keep goals vague.
Here is a five-step framework grounded in research:
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Capture one to two specific goals. Not “grow my career” but “build SQL skills to qualify for data analyst roles by Q3.” Specificity triggers support.
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Create a 70-20-10 development plan. The University of Rochester HR Career Conversation Guide recommends 70% on-the-job learning (stretch projects), 20% learning from others (mentors, shadowing), and 10% formal courses.
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Cross-check goals against labor market data. Use BLS Employment Projections to confirm your target field is growing, and O*NET to identify the three to five concrete skills to build.
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Update your resume immediately. If the conversation revealed that a certain skill or certification matters more than you thought, add it to your resume builder draft now, not later.
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Schedule a follow-up. Lattice’s career development guide recommends ending every career conversation by setting a date for a progress check. Without a follow-up, even strong conversations fade.
Deloitte research finds that organizations where employees actively communicate career aspirations see about 25% higher engagement and retention. Structured follow-through benefits both sides.
Common Mistakes to Avoid When Asking Career Questions
The most damaging mistakes include talking too much, leading with salary, skipping research, asking vague questions, and failing to follow up afterward.
Talking more than listening. Harvard Business Review research by Zenger and Folkman found that only about 10% of people are natural good listeners. In a career conversation, aim to listen at least 70% of the time. You’re there to learn, not to audition.
Leading with salary. A 2023 Robert Half survey found that 61% of hiring managers view bringing up salary too early as a red flag. The same principle applies in informational interviews. Build rapport first; ask about compensation structures later.
Asking questions you could Google. “So what does your company do?” signals zero preparation. According to Michael Page’s global survey of hiring managers, going in without research is the number one interview mistake. Come with a baseline understanding and ask questions that build on it.
Being vague. “Any advice for me?” puts the burden on the other person to guess what you need. Harvard Business School Online emphasizes that specificity in both questions and answers is what separates productive conversations from forgettable ones. Ask “What skills did you need for your first promotion?” instead.
Treating it as a one-way transaction. Adam Grant’s research on networking, summarized in HBR, shows that people who only ask self-serving questions (“Can you get me a job?”) build weaker relationships. Show genuine curiosity. Offer something in return, even if it’s just a relevant article or a connection to someone they’d find interesting.
Skipping the follow-up. An Indeed survey found that 47% of hiring managers consider “not asking any questions” a top red flag. The inverse is also true: asking great questions and then disappearing wastes the goodwill you built. Send a thank-you note. Reference a specific insight. Stay in touch.
Every career conversation is a chance to gather intelligence that typically takes hours of research to find on your own. The 10 questions above are designed to surface real data about salary ranges, skill demands, day-to-day realities, and growth trajectories in any field. Use what you learn to target the right roles, close skill gaps, and build a stronger application. Ready to put those insights into action? Start updating your resume with the Resumeio.com AI resume builder or browse resume examples tailored to your target industry.
