Good Questions to Ask a Lawyer About Their Career
Questions for a lawyer about the career itself: what the week actually consists of, billable hour targets, what the first years out of law school cost in hours and debt, how clients are won, and whether they would do it again. For students and career changers weighing law school.
The questions
Open any question for the note
What kind of law do you actually practise day to day?
Why ask it
Law is not one job. A public defender, a transactional associate, and an in-house counsel share a bar card and almost nothing else, so pinning down the practice area first stops you from generalising one person's answer into a picture of the profession.
Walk me through yesterday: what took the most hours?
Why ask it
A single real day is harder to romanticise than a typical week. Expect document review, email, and internal calls to dominate, and note whether court or client contact appears at all.
How much of your week is writing, how much is talking to clients, and how much is in court?
Why ask it
Most people considering law picture advocacy and get drafting. If the split surprises you, that is the single most useful thing you will learn from the conversation.
What is your billable hour target, and what does hitting it do to your calendar?
Why ask it
Billable hours are not worked hours. Ask how many hours they have to be at work to bill the target, since the gap between those two numbers is where evenings and weekends go.
When did you last take a week off without checking email?
Why ask it
A plain factual question that gets past any statement about balance. Hesitation is itself the answer, and a lawyer who can name the trip and the year is telling you something real about their firm.
How did you end up in this practice area: was it chosen or did it happen?
Why ask it
Many lawyers land in a specialism because of a first-year rotation or the firm that made an offer. Hearing how much was accident is a useful corrective if you are planning your own path in detail.
What did your first two years out of law school cost you, in hours and in money?
Why ask it
The early years set the pattern and the debt. A specific answer about hours worked and what was actually paid down beats any general statement about the profession being demanding.
How long did your law school debt take to pay off, and would you borrow that again?
Why ask it
Ask it directly. The answer often depends on things applicants ignore, such as whether they had a scholarship, worked in the public sector with loan forgiveness, or left a well-paid job to attend.
Which part of the work do you still find genuinely interesting?
Why ask it
Interest that survives ten years is usually narrow and specific: a type of problem, a kind of drafting, a client industry. If nothing comes to mind, you have learned something important about where this path can lead.
What kind of person struggles here even though they were a strong student?
Why ask it
The failure modes in practice are rarely academic. Tolerance for tedium, willingness to chase clients, and handling a partner's edits without taking it personally come up more often than analytical ability.
How do clients find you, and how much of your job is that now?
Why ask it
Origination becomes the job as people get senior, and nobody teaches it. If they describe business development as most of their week, that is the real career you would be entering, whatever the job title says.
What is the hardest conversation you routinely have with clients?
Why ask it
Usually delivering a bad answer, quoting a fee, or telling someone their case is not worth running. This is the part of lawyering that reads as customer service and is invisible from outside.
What do you do when a client wants something you think is a mistake?
Why ask it
The interesting answers describe a process: put the advice in writing, document the instruction, decide what you will and will not put your name to. Vague answers about persuasion suggest they have not been tested on it.
Have you ever withdrawn from a matter or turned work away, and what made it clear you should?
Why ask it
Ethical lines look obvious in a classroom and arrive ambiguously in practice. A concrete example, even a small one, tells you far more than any statement of principle about integrity.
What happens when a case goes badly: how do you carry it, and how does the firm treat it?
Why ask it
Two separate things are being asked, and both matter. Whether losses are examined or quietly buried is a fair test of the place, and how they personally recover is a fair test of whether the work is survivable.
What did nobody tell you about how promotion or partnership actually works here?
Why ask it
The stated criteria and the real ones rarely match. Listen for whether the decisive factor is hours, a book of clients, a sponsor internally, or luck about which group was busy that year.
Which skills you use most were not taught in law school?
Why ask it
Common answers are negotiation, managing a client's expectations, delegating, project managing a matter, and pricing work. This is the shortest route to knowing what to build outside your coursework.
If you were qualifying now, what would you expect to be different?
Why ask it
Ask them to reason about the entry-level market they can observe rather than to predict the profession. Concrete observations about document review, contract work, or in-house hiring are worth more than speculation.
Would you go to law school again, and would you do it differently?
Why ask it
The regret, if any, is usually specific: a cheaper school, a different first job, or two years of work beforehand. That specificity is the part you can use.
What would you say to someone who wants law mainly for the money or the prestige?
Why ask it
You are inviting candour, and the answer tells you both what the job pays for and what it takes. Watch for whether they mention the people who left, since attrition is the fact most conversations about legal careers skip.
Getting an Honest Conversation About Legal Careers
Practical guidance for the conversation itself
Setting it up
Say up front that you are not asking for legal advice
Lawyers are trained to be careful with anyone who might be treated as a client. Opening with a sentence that you want to hear about the career, not about a legal problem, removes that caution and gets you a franker conversation.
Ask for twenty five minutes and mean it
Time is literally billed here, so a short, specific request is more likely to be accepted than an open invitation to coffee. Send two or three questions in advance and stop when the time is up.
Ask a lawyer whose job you might actually want
Advice from a corporate partner is close to useless if you want to do family law in a small practice, and the reverse holds too. Match the person to the version of the career you are considering.
Make the answers concrete
- Ask about a specific day or week rather than a typical one. Averages get sanded smooth in the telling.
- Ask for numbers: billable target, hours actually worked, debt at graduation, years to pay it down.
- When they describe a case, ask what they personally did on it. Junior work and partner work sound identical in a summary.
- Ask what happened to the people who started with them. Attrition tells you more about a firm than its own description of its culture.
Reading the answers
- Someone who only describes matters and never the calendar is selling you the profession rather than describing it.
- Precision about hours usually means honesty. Vagueness about hours usually means the number is bad.
- Pay attention to how they talk about people who left the law. Contempt suggests a firm where leaving is treated as failure.
- One practice area is not the field. Ask two or three lawyers in different settings before you conclude anything.
What to skip
- Do not ask them to assess your chances at a particular law school. They have no visibility into admissions and the answer will be a guess.
- Do not ask about named clients or live matters. They cannot answer, and asking makes the rest of the conversation guarded.
- Do not ask for free advice on your own dispute, even briefly. It changes the relationship and can create a conflict for them.
- Do not treat their firm's recruiting material as a starting point. Ask what it gets wrong instead.