Interview Questions to Expect When Working With a Headhunter

If you’ve been contacted by a headhunter or decided to work with one, that’s a good sign — it means your profile has potential. But before you get introduced to any employers, there’s one important step: the interview with the headhunter.

Unlike a formal job interview, this conversation is more exploratory. Still, it’s critical. A headhunter is evaluating how well you’ll present to their client — and whether you’re worth recommending.

Here are the types of questions you can expect, and how to prepare for them.

1. Can You Walk Me Through Your Career So Far?

This is often the opening question — and it sets the tone.

What they’re assessing:

• How clearly and confidently you communicate

• Whether your experience matches the type of roles they place

• Your ability to highlight relevant milestones

How to answer:

• Be structured: start with your current/most recent role and work backward

• Focus on key accomplishments, not just duties

• Emphasize themes that match your career goals (e.g., leadership, growth, technical expertise)

2. Why Are You Looking to Make a Move?

This helps the headhunter understand your motivation — and whether it aligns with the opportunities they have.

Be ready to explain:

• What you’re looking for that your current role doesn’t offer

• Whether you're looking for a promotion, industry switch, relocation, or better alignment

• That you’re not just “job shopping” with no direction

3. What Are You Looking for in Your Next Role?

A vague or inconsistent answer can raise red flags. The clearer you are, the easier it is for the headhunter to position you.

Things to define:

• Job title or area of focus

• Industries or types of companies you're open to

• Preferred locations, work arrangements (remote, hybrid), and team size

• What kind of leadership or culture you thrive in

4. What Is Your Current Compensation and Expected Salary?

In many regions (including Singapore and Dubai), compensation transparency is part of the process.

What they want to know:

• Your current base, bonuses, and benefits

• Whether your expectations are realistic for the market

• If there’s flexibility in your range

Tip: Be honest and clear — but also do your research so you can justify your expectations confidently.

5. Are You Open to Relocation or Remote Work?

If you're working with an international headhunter or applying to cross-border roles, this question matters.

Be prepared to discuss:

• Your availability to relocate (timeline, family considerations, visa needs)

• Whether you’re looking to stay local or explore new markets

• Your flexibility for hybrid or remote roles

6. How Soon Can You Start?

Hiring timelines vary, but knowing your availability helps recruiters match you with the right opportunities.

Be clear on:

• Your current notice period

• Whether you're actively interviewing elsewhere

• Any flexibility (e.g., early handover, open to short-term contract roles)

7. What Are Your Deal Breakers?

Headhunters don’t want to waste time — or yours.

Common deal breakers might include:

• Salary below a certain level

• Inflexible work arrangements

• Roles without growth opportunities

• Industries or companies you want to avoid

Tip: Be honest but constructive. Focus on what matters to you, not just what you don’t want.

8. Are You Interviewing Elsewhere?

This helps the headhunter understand how urgently they should act on your behalf — and how competitive your profile is.

Be honest if:

• You’re in advanced stages elsewhere

• You’re early in your search but exploring seriously

• You’re waiting on an offer but keeping options open

9. What Are You Most Proud Of in Your Career So Far?

This isn’t just about accomplishments — it’s about energy and passion.

What they’re listening for:

• Ownership of outcomes

• Signs of leadership, creativity, or initiative

• How you describe your impact in a meaningful way

Final Thoughts

The goal of a headhunter interview isn’t just to screen you — it’s to understand you, so they can pitch you effectively to employers. The better you prepare, the stronger your chances of getting matched with the right opportunities.

Treat it like a two-way conversation — but also like a first impression.

Looking to connect with headhunters who understand your industry and career goals?
HelloRecruiters makes it easy to get matched with relevant recruiters across Singapore, Dubai, and beyond.
Start here → hellorecruiters.co