Questions to Ask an Alumni
Twenty questions for a student or recent graduate talking to an alumnus of their school or programme. They move from the plain facts of the person's career to the parts nobody publishes: how they were actually hired, what the daily work is, and what they would do differently.
The questions
Open any question for the note
What year did you graduate, and what did you study?
Why ask it
Starting with the facts saves you from guessing later. The gap between their graduation year and now also tells you how much of their advice is about a job market that still exists.
What are you doing now, and how would you describe it to someone outside the field?
Why ask it
Job titles hide the work. Asking for the plain-language version usually gets you the daily tasks, which is what you actually need in order to know whether you want the job.
What was your first job after graduating, and how did you get it?
Why ask it
The mechanism matters more than the employer: a careers fair, a professor's referral, a cold email, a temp role that turned permanent. If they cannot remember how it happened, it was probably a connection rather than an application.
How did you get from that first job to this one?
Why ask it
Career paths look linear on a profile page and rarely are. Listen for the sideways move or the year out, because that is the part nobody puts in writing.
What did you do while you were a student that turned out to matter?
Why ask it
Alumni almost never name their grades here. When they name a society, a part-time job or one specific project, that tells you where to spend your own time.
What did you spend time on that turned out not to matter?
Why ask it
Harder to ask and more useful than the previous question. Beware the reflexive 'nothing was wasted', it is polite rather than true, and a gentle pause often produces a real answer.
What surprised you most in your first year of working?
Why ask it
This surfaces the gap between coursework and the job: meeting culture, how slowly decisions get made, how much writing is involved. It is the cheapest form of expectation management you can get.
What skills do people in your field assume you already have?
Why ask it
Unwritten baselines vary by industry, spreadsheets, reading a contract, writing a clean email, basic statistics. Their answer gives you a concrete list to work on before you apply.
What does an ordinary Tuesday look like for you?
Why ask it
Naming a specific day stops them describing their job in aspirational terms. If the answer is mostly meetings and email, you have learned something the recruiting material will not tell you.
What part of the job would put someone off if they knew about it in advance?
Why ask it
Phrasing it as a warning to others makes it easier to answer honestly than 'what do you dislike'. Common answers involve travel, on-call weeks, billing targets or clients.
How has the entry route into your field changed since you started?
Why ask it
Requirements shift: portfolios replacing degrees, certifications appearing, internships becoming mandatory. Someone five years ahead of you can tell you which door is currently open.
How did you decide when to leave a job?
Why ask it
The reasoning is transferable even when the jobs are not. Watch whether they left for money, a manager, boredom or a ceiling, and whether they later thought the timing was right.
Was there a point where you nearly changed direction entirely?
Why ask it
Most people have one. What they say about why they stayed, or why they moved, tells you more about the field's realities than any success story.
What do you know now about pay and negotiation that you wish you had known then?
Why ask it
Money questions land better when framed as hindsight rather than a request for their salary. Many alumni will happily name a range for the role even when they will not name their own.
How do people in your field find out about openings before they are advertised?
Why ask it
Every industry has its channel: a Slack group, a mailing list, a specific recruiter, one conference. This is the single most actionable question on the list.
Who else should I be talking to, and would you be willing to introduce me?
Why ask it
Asking for a name is a smaller favour than asking for a job and usually gets a yes. If they hesitate, do not push, it often means they are new enough to be protecting their own standing.
What would make you say yes to a candidate with no experience?
Why ask it
This reframes them as the person doing the hiring, which produces specifics: a piece of work to show, evidence of finishing things, a reason for wanting this field and not a neighbouring one.
If you were starting again now, would you take the same route?
Why ask it
Ask late, once they are being candid. A slow answer here is usually more informative than a quick one, and 'no, I would skip the master's' is worth the entire conversation.
What is one thing you would do differently in your first two years?
Why ask it
Concrete and answerable, unlike broad requests for advice. Answers often involve asking for help sooner, keeping a record of their work, or leaving a bad role earlier.
Would it be all right to come back to you with a question in a few months?
Why ask it
Closing with a small, specific ask turns one conversation into an ongoing contact. Say what you will do with what they told you, and then actually do it.
Making the most of an alumni conversation
Practical guidance for the conversation itself
Before you meet
Do the reading they can see
Know their current role, their employer and roughly how long they have been there. Nothing wastes a short call faster than spending it on facts that were on their profile page.
Decide the one thing you want
Pick a single outcome: a realistic picture of the job, a view on whether a postgraduate course is worth it, or two more names. A conversation with one purpose is easier for them to help with than a general chat.
Ask for a specific, small slot
Twenty minutes on a video call at a stated time gets accepted more often than an open request for coffee. Say up front what you want to ask about.
During the conversation
- Open with facts, move to experience, leave hindsight and pay for the last third once they have warmed up.
- Ask about the ordinary rather than the highlights: a normal Tuesday, the last thing they finished, the part of the week they dread.
- Follow one thread properly instead of working through a list. The good material is almost always in the second follow-up.
- When they generalise, ask for the instance: 'was there a time that happened?'
- Take notes visibly. People give more detail when they can see it being written down.
- Watch the clock yourself and offer to stop at the time you asked for. Being let go early is what earns the second conversation.
What to avoid
Asking for a job in the first ten minutes
Alumni are usually willing to advise and reluctant to be recruiters. Ask about the field and the route in, and let any referral come from them.
Treating one person's path as the pattern
A single career is one data point shaped by timing and luck. Two or three conversations in the same field will show you which parts were general and which were personal.
Flattery about the institution
Shared background is why they took the call, not a reason to spend it on nostalgia. One sentence of connection is enough.
Silence afterwards
Send a short thank-you within a day naming one thing you will act on. Most alumni never hear back from the students they help, which is why the ones who do follow up get remembered.
If you are on the other side of the table
Alumni volunteers reading this can make these conversations far more useful by answering the awkward questions directly: how you actually got hired, what you earn at the level being asked about, and what you would not do again. Vague encouragement is comfortable to give and of very little use to receive.