Questions to Ask Lawyers About Their Career
Questions for asking practicing lawyers about the shape of their career: first jobs, moves between roles, mistakes, income, burnout, how the work itself has changed, and what they would tell someone starting now.
The questions
Open any question for the note
What was your first job out of law school, and how long did you stay?
Why ask it
First jobs are often accidental and rarely the plan, and the length of stay tells you whether it worked. Two years is a normal exit; six months usually has a story attached that is worth hearing.
How many times have you changed firms or roles, and what triggered each move?
Why ask it
The triggers are the useful part: a partner leaving, a practice group shrinking, a client following them, a bad review, a child. Careers look designed in hindsight and are mostly a series of responses to events.
When did you feel like you actually knew what you were doing?
Why ask it
Most lawyers name a point several years in, often later than a junior expects, and many will admit the feeling arrived and then left again when they changed areas. It is a reassuring answer to hear early in your own career.
Who gave you work in the first few years, and why do you think they picked you?
Why ask it
Early careers are made by two or three people who kept handing over files. The reason they gave is usually mundane, such as fast turnaround or clean drafts, which tells you what to be known for.
Did you build your own client base, or inherit one?
Why ask it
Origination is what separates senior roles from senior titles, and inherited relationships are a legitimate but fragile foundation. Ask how they got the first client that was genuinely theirs, since that is the transferable part.
What did you turn down that you still think about?
Why ask it
The declined clerkship, the government role, the move abroad. This question gets at the counterfactual career, and the fact that they still think about it says something about what the current one lacks.
What did you say yes to that you should have refused?
Why ask it
Answers tend to involve a client they knew was trouble, a matter far outside their competence, or a role taken for the title. Overcommitment is the standard early career failure, and hearing the specific version is more useful than being warned about it.
How did your income change across your career, and where were the jumps?
Why ask it
The pattern matters more than the numbers, and lawyers will usually describe the shape without the figures. Pay in law tends to move in steps tied to particular transitions rather than rising steadily, so what you want to identify is which transitions those were: partnership, a lateral move, the first client of their own.
Which of your skills has aged best?
Why ask it
Rarely doctrine. Answers usually involve writing clearly, reading a room, or explaining a hard thing to a frightened person, and none of those were graded in law school. Note which ones you are currently neglecting.
What part of the job did you get wrong for years before you noticed?
Why ask it
Common admissions are billing badly, avoiding difficult client conversations, and never delegating. This question asks for self-criticism about method rather than a single mistake, and the answers are unusually candid.
How did you handle your first serious mistake?
Why ask it
Every practicing lawyer has missed something or misread something. What you want is the mechanics: who they told, how fast, what the firm did, and what it actually cost, since the instinct to conceal is the part that ends careers.
Have you ever come close to leaving law?
Why ask it
A large share will say yes, usually at a specific point they can name. Ask what changed, because the answer is often a move within the profession rather than out of it, which is the option people considering leaving tend to overlook.
What did having a family, or not having one, do to the shape of your career?
Why ask it
This is where the standard career story usually breaks and something more honest appears: a track slowed, a specialty changed, hours renegotiated, help paid for. Ask it of both men and women, since it is usually only put to women.
If you have ever been in a job that was making you unwell, how did you get out of it?
Why ask it
The practical route out is what matters: whether they lined something up first, whether they told anyone, how long it took to admit it. Rates of burnout in the profession make this one of the most useful questions you can ask.
How has the work itself changed since you started, not just the industry?
Why ask it
Push past the general observations about technology and billing pressure. You are asking what a document, a negotiation, or a hearing feels like now compared with then, and only someone with a long view can answer it.
In a place like yours, what actually gets someone promoted, as opposed to what the criteria say?
Why ask it
Someone twenty years in has watched a lot of promotions and can usually name the real drivers: hours, revenue brought in, being close to the right partner. Phrasing it about their kind of workplace rather than yours keeps it a question they can answer freely.
How do you decide which matters or clients to take now?
Why ask it
Once someone can refuse work, their criteria reveal what they have learned: which clients pay, which cases consume a year, which subject matter they will not handle again. It is a compressed summary of everything that went wrong before.
What does your work look like now compared with ten years ago?
Why ask it
Senior practice often drifts toward supervision, business development, and internal management, and away from the legal work that drew them in. Whether they consider that a promotion or a loss is worth knowing before you aim at the same role.
What do you plan to do at the end of your career, and when did you start thinking about it?
Why ask it
Answers range from a firm date to no plan at all, and the ones with no plan are often the most candid about why. Succession, client handover, and identity after practice are things most lawyers begin considering later than they intended to.
What would you tell someone about to make the same choices you did?
Why ask it
Ask this last, once the conversation has covered the hard parts, so the answer is grounded in what they have just said rather than in general advice. If it contradicts something earlier, the earlier version is usually the truer one.
Asking lawyers about their careers
Practical guidance for the conversation itself
Who to ask, and when
- Lawyers five to eight years in remember the mechanics of getting started and can still describe the first years accurately.
- Lawyers twenty years in can see the shape of a whole career and are usually franker about what it cost, particularly once they are no longer competing for advancement.
- People who left the profession are the most underused source. They can tell you what did not work in a way that people still inside it generally will not.
- Avoid asking about pay, mistakes, or burnout in a group. These questions need one person and no audience.
- Timing helps: after a matter closes rather than while it is running, and not during a week when they are in hearings.
Making it worth their time
- 1Say what decision you are actually facing. Concrete stakes get considered answers; general curiosity gets general advice.
- 2Ask about their own history rather than the profession's. Nobody has anything new to say about the state of the legal industry.
- 3When you get a tidy answer, ask what happened in the year before it. That is where the version worth hearing usually lives.
- 4Do not argue with their conclusions, even if you think their market no longer exists. Ask what they think has changed since.
- 5Close by asking who else you should be talking to, and follow up on it.
What to listen for
- Repetition across several lawyers is the signal. One person's regret is a personality; four people naming the same regret is a pattern in the profession.
- Notice which answers are rehearsed. The story about the big case is polished; the story about the year they nearly quit is not, and it is the informative one.
- Separate advice that reflects their era from advice that still applies. Hiring, billing, and remote work have all shifted considerably.
- Pay attention to how they describe colleagues. It is the clearest available signal about the culture they work in.
- Watch your own reaction to their description of the daily work. If it flattens you, that is data about you, not about them.