Questions to Ask a Headhunter
Questions for the first call with an external recruiter who has approached you about a role, or whom you are considering working with: who is paying them, how real the search is, what they will do with your name, and whether the job is worth a conversation.
The questions
Open any question for the note
How did you come across my name?
Why ask it
A recruiter who cites a specific project, publication, or referral has done research and probably has a genuine brief. One who says they found your profile in a search is likely working a keyword list, which usually means volume outreach rather than a targeted shortlist.
Which company is this for?
Why ask it
Retained recruiters on a real search name the client early, sometimes after a quick confidentiality request. Contingency recruiters often withhold the name to keep you from applying directly. Persistent vagueness past the first call usually means they do not have the assignment.
Are you retained on this search, or working it on contingency?
Why ask it
Retained means the client is paying them regardless and they usually have exclusivity and direct access to the hiring manager. Contingency means they get paid only if their candidate is hired, which makes them faster but less able to answer real questions about the role.
Have you spoken with the hiring manager directly, or are you working through HR?
Why ask it
Recruiters who have debriefed the hiring manager can tell you why the last person left and what would get someone rejected in round two. Those routed through a coordinator will pass along a job description you could have read yourself.
Why is this role open?
Why ask it
New headcount, a resignation, a firing, and a backfill after a reorganization are four very different situations. A recruiter who does not know, or who gives a smooth growth answer for a job that has been posted for five months, has not been briefed properly.
How long has the search been running, and how many candidates are in process?
Why ask it
A search open six months with no finalists usually signals an unclear spec, an unrealistic budget, or a difficult hiring manager. A search with three candidates in final rounds tells you your timeline is compressed and you may be a comparison hire.
What is the compensation range the client has actually approved?
Why ask it
The word approved matters. Recruiters often quote an aspirational top end. Ask for the base band, the bonus target, and whether equity is included, and ask what the last person in the role or a peer was paid if they know.
What does this person need to accomplish in the first year for the client to consider the hire a success?
Why ask it
This turns a list of responsibilities into a measurable brief. If the recruiter cannot answer, neither can the client, and you would be walking into a role whose success criteria get invented after you start.
What kind of background got the last few candidates rejected?
Why ask it
Rejection patterns reveal the unwritten spec: the client says open-minded but keeps passing on anyone without industry experience, or without direct reports. This is the most useful question on this list and few candidates ask it.
Where does my profile fall short of what they asked for?
Why ask it
A recruiter genuinely representing you will name the gap and tell you how they plan to frame it. One who insists you are a perfect fit is either flattering you into the pipeline or has not read the brief closely.
What is the interview process from here, and how many rounds?
Why ask it
Ask for the stages, who sits in each, and whether there is a case study, panel, or presentation. Six rounds over ten weeks is a real cost if you are employed, and it is fair to know before you take the first call.
Before you send my resume anywhere, will you check with me first?
Why ask it
Say this explicitly and get an explicit yes. Contingency recruiters sometimes blanket-submit candidates to establish a fee claim, which can burn you with a company you were already talking to and can leak your search to your employer.
Have you already submitted me anywhere, or presented my profile to any client?
Why ask it
Worth asking outright if you were contacted out of nowhere. If your name is already with a company you know, you need to sort out ownership now, since duplicate submissions can get a candidate dropped rather than fought over.
Who inside your firm will see my details, and how long do you keep them?
Why ask it
Large firms share databases across offices and practice groups, so a note about your reasons for leaving can circulate widely. Ask whether you can be marked confidential and whether they will avoid contacting your current employer.
Do you have any restriction on placing candidates out of my current company?
Why ask it
Firms retained by your employer are usually barred from recruiting from it, and some have off-limits agreements you would never see. Better to find out now than after two rounds of interviews.
How does the client typically handle counteroffers and notice periods?
Why ask it
It tells you whether they are used to hiring senior people from stable jobs or expect immediate starts. It also gives you an early read on whether the recruiter will push you to resign before your offer is fully papered.
What has the client been difficult about in this process?
Why ask it
Every search has friction: slow scheduling, a partner who blocks candidates, a low first offer. A recruiter willing to name it is being straight with you, and their answer predicts how the next six weeks will feel.
If this role is not right, what else are you working on, and what would you keep me in mind for?
Why ask it
This separates recruiters who build long relationships from those working a single requisition. A specific answer about their desk and the kinds of mandates they get is worth more than the current job.
What is your fee arrangement with the client?
Why ask it
Fees are usually a percentage of first-year compensation, which means the recruiter's incentive is aligned with a high offer for you, but only if the deal closes. Knowing the structure helps you read their advice during negotiation, especially if they suggest accepting quickly.
How do you want to stay in touch, and what would you like from me between now and then?
Why ask it
Ends the call with a concrete next step and reveals whether they intend to follow up at all. Recruiters who ask for a target company list or an updated resume with numbers are planning to work your search rather than file it.
Working with an External Recruiter
Practical guidance for the conversation itself
Handling the first call
You are not obliged to be a candidate yet
A first call can be exploratory on both sides. Say plainly that you are happy to learn about the role but are not in an active search and do not want to be submitted anywhere yet. Recruiters hear this constantly and a good one will respect it.
Do not lead with your salary history
If asked early, give a target for a new role rather than your current number, and say the target reflects the scope of the job described. Many jurisdictions now bar employers from asking salary history, but recruiters still ask, and an early number tends to anchor the whole process.
Take the call somewhere private
Recruiters often ring during the workday. If you are at your desk or in an open office, offer a specific time later rather than stepping into a stairwell for a rushed conversation about leaving your job.
Retained and contingency, and why it changes your answers
- Retained: the client pays in stages whether or not a hire happens. The recruiter usually has exclusivity, a real brief, and access to the decision maker, so their answers about the role are worth trusting.
- Contingency: the recruiter is paid only on a placement and may be one of several working the same job. Speed matters more to them than fit, and your resume is a lottery ticket unless you set submission rules.
- Internal or in-house recruiter: an employee of the hiring company. They know the process well but represent the employer, not you.
- Staffing or contract agency: places temporary and contract workers, often at an hourly bill rate. Ask what they bill the client versus what you are paid if you go this route.
- If you cannot tell which type you are speaking to, the fee question sorts it out quickly.
Protecting your search
- Give written instructions by email after the call: no submissions without your approval, no contact with your current or former employers without permission.
- Keep your own list of which recruiter sent you where and on what date. If two recruiters submit you to one company, that list is what resolves it.
- Do not hand over references until you are in a late round. Reference contacts get mined for new business.
- Be careful with the reason you are leaving. A candid complaint about your boss can travel further than you expect in a small industry.
- If a recruiter pressures you to interview for something you have declined, or gets your details in front of a client after you said no, stop working with them.
Reading the recruiter
Signs they have a real mandate
They name the client, know why the role is open, can describe the hiring manager's style, and are specific about the process and timeline. They also tell you when you are not a fit rather than keeping you warm.
Signs they are fishing
The role is described only in generalities, they push for your resume in the first two minutes, they ask a lot about who else in your team is good, and they cannot say when the client last interviewed anyone. Sourcing calls are not always dishonest, but treat them as information gathering rather than an opportunity.