Questions to Ask General Counsel During Interview
For CEOs, board members, and hiring committees interviewing a candidate for general counsel. These 20 questions test judgment under pressure, outside counsel spend, board reporting, and whether the candidate can say no to the business without being sidelined.
The questions
Open any question for the note
Walk me through the legal function you inherited in your last role. What did it look like on day one, and what did it look like when you left?
Why ask it
Opens with narrative rather than philosophy, so you hear scope: headcount, budget, matter volume, what was outsourced. Candidates who cannot describe the starting state usually inherited something already working and did not build it.
What kinds of decisions did your CEO bring to you before making them, and what did they decide without you?
Why ask it
This maps their real seat at the table better than any title. If nothing was ever decided without them they may be a bottleneck; if the big calls happened elsewhere, they were treated as a paperwork function.
Tell me about a time you told the business no and it stuck. Then tell me about a time you were overruled.
Why ask it
Asking for both halves stops the rehearsed hero story. The overruled example is the informative one: listen for whether they documented the risk and moved on, or sulked, escalated to the board, or quietly resisted.
How do you decide what a risk is actually worth? Give me a matter where you recommended accepting risk rather than eliminating it.
Why ask it
A general counsel who eliminates every risk stops the company. The answer should include numbers, likely exposure against cost of avoidance, not a framework diagram.
How much did you spend on outside counsel last year, and what did you do to change that number?
Why ask it
Watch whether they know their own spend without checking. Strong answers name specific levers: rate cards, alternative fee arrangements, panel consolidation, work pulled in house, matter budgets with variance reporting.
How do you pick a firm for a bet the company matter versus routine work?
Why ask it
Reveals whether they buy brands or partners. The useful answer distinguishes the named partner they trust from the firm letterhead, and explains who actually staffs the work below that partner.
What did the legal section of your board or audit committee report contain, and how often did you present alone?
Why ask it
Board access is where general counsel roles differ most. Presenting only alongside the CFO, or only when there is litigation, indicates limited standing. Ask to see the structure of the report, not just the topics.
How do you handle a situation where the CEO is the legal problem?
Why ask it
The hardest structural question in the job, and one every candidate should have thought about. Expect discussion of who the client is, the duty to the company rather than the executive, and the practical path to independent directors.
Where do you draw the line on privilege when you are also giving business advice?
Why ask it
Mixed role advice is routinely found not privileged later. Look for concrete habits: separate memos for legal advice, care with distribution lists, instructing outside counsel for sensitive investigations.
Describe the last internal investigation you ran. Who did you report to, and what changed afterward?
Why ask it
Investigations expose both rigor and courage. The follow up question that matters is what changed: an investigation with findings and no consequences means the general counsel was used as cover.
What compliance obligations does our business have that you would want to look at first?
Why ask it
This tests preparation directly. A candidate who has read your filings, product, and sector rules will name specifics. Generic answers about a compliance culture mean they did not do the homework.
Which regulator have you dealt with directly, and how did that go?
Why ask it
There is a large gap between advising on a regime and sitting across a table from its enforcement staff. Ask what surprised them about the process and what they would do differently in a first contact.
How do you keep contracting from becoming the slowest part of a sales cycle?
Why ask it
This is where most of the company will actually experience the legal team. Practical answers cite playbooks, pre approved fallback positions, signature thresholds, and cycle time they measured.
What litigation have you owned end to end, and how did you decide when to settle?
Why ask it
Look for a stated decision rule rather than instinct: exposure range, cost to trial, precedent risk, distraction to executives. Candidates who have never tried a case can still manage litigation well, but they should say so plainly.
How would you handle a data breach in the first 48 hours?
Why ask it
Notification clocks are short and unforgiving, so the answer should be sequenced and specific about who is called and in what order. Vagueness here usually means they have only read the plan, not run it.
How have you handled a deal where diligence found something serious late in the process?
Why ask it
Tests whether they can shape terms rather than just flag problems. Strong answers involve indemnities, escrow, price adjustment, or carve outs, and a clear account of how they told the deal sponsor.
How do you decide what to hire in house versus what to keep outside permanently?
Why ask it
Reveals whether they build teams to fit the work or to grow headcount. Listen for volume and predictability as the test: recurring, high volume work in house, episodic specialist work outside.
Who have you hired that turned out to be a mistake, and what did you learn from it?
Why ask it
A general counsel who has never made a bad hire has either not hired much or is not being candid. The learning matters more than the story: changed interview process, earlier feedback, faster exits.
What would tell you, a year from now, that this was the wrong job for you?
Why ask it
Better than asking what they want, because it surfaces their real dealbreakers: no board access, a CEO who routes around them, a company unwilling to fund the function. Their answer tells you what you would need to change.
What do you want to ask us about how this company handles bad news?
Why ask it
Closing with their question tests seniority. Serious candidates probe for prior legal problems, executive turnover, why the last general counsel left, and whether the board hears things directly.
Running a General Counsel Interview
Practical guidance for the conversation itself
What This Hire Actually Turns On
Independence Beats Technical Depth
Most experienced candidates can handle the doctrine or hire someone who can. Far fewer can hold a position against a determined CEO and stay effective afterward. Spend your hardest questions on that, not on black letter law.
Ask for Numbers, Not Approaches
Budget, headcount, outside counsel spend, matter cycle times, settlement values. A candidate who ran a function knows these without notes. Anyone answering in the language of philosophy is describing a job they observed rather than held.
Match Stage, Not Prestige
A general counsel from a company with forty lawyers and a mature compliance program may have no experience building anything from nothing. Ask specifically what they created versus inherited.
Include a Non Lawyer Interviewer
Have a sales leader or engineer interview them. If that person comes out feeling lectured to, the rest of the company will feel the same way, and the legal function will be routed around.
Signals Worth Following Up On
- They describe their client as the CEO rather than the company. Correct answers get this distinction right without prompting.
- Every risk story ends with the risk being eliminated. Real practice involves priced, accepted, documented risk.
- They cannot name what they stopped doing. Good function builders kill low value work as well as adding services.
- Outside counsel relationships are described by firm name only, never by individual partner.
- No account of a mistake, anywhere in two hours of interviews.
- They ask no questions about prior legal problems or why the role is open.
Interviewer Mistakes
Turning the Interview Into a Legal Quiz
Hypothetical doctrine questions test recall, which is the least scarce quality in a senior lawyer. Ask about matters they owned and decisions they made instead.
Skipping the Reference Detail
For this role, references from the business side are more informative than from other lawyers. Ask a former sales or product leader whether legal made deals possible or slowed them down.
Leaving Board Access Undefined
If you do not settle before the offer whether they report to the CEO, sit on the executive team, and have direct access to the audit committee, you will be renegotiating it during a crisis.
Ignoring How They Handled Their Departure
Listen closely to how they discuss their last employer's problems. Someone who discloses more than they should in an interview will do the same when they leave you.
A Workable Interview Structure
First Conversation, Roughly an Hour
- 1Scope: what the function looked like when they arrived and when they left.
- 2Standing: which decisions reached them, which did not.
- 3Judgment: one risk they recommended accepting, with the numbers.
- 4Money: last year's outside counsel spend and what they changed.
- 5Their questions for you.
Second Round, With the Board or Audit Chair
- 1Board reporting: what the legal report contained and how often they presented alone.
- 2Independence: how they would handle the CEO being the legal problem.
- 3Investigations: the last one they ran and what changed after it.
- 4Crisis: the first 48 hours of a breach or a regulatory inquiry.
- 5Fit: what would make this the wrong job a year from now.