If you're a senior communications leader, chances are you've had your share of exploratory calls with headhunters. Some are transactional. Others, the good ones, are strategic, laser-focused, and surprisingly revealing, and they are relationships you will want to build on.
When you’re speaking to a headhunter who truly understands corporate communications, someone who has sat across from Global Heads of Corporate Affairs, CEOs and Boards, the questions will go far beyond your CV. These are the conversations that get to the heart of how you think, what drives you, and where you can add real value.
Here are the 10 questions a seasoned comms headhunter is likely to ask in that all-important first conversation, and why each one matters:
1. “Talk me through the thread that runs through your career - how do you position yourself as a comms leader?”
This isn’t a prompt to recite your CV. It’s an invitation to own your professional identity. Are you a reputation architect? A trusted advisor to the C-suite? A change comms specialist? A crisis comms professional? They’re listening for clarity, confidence, and how you frame your value at the strategic level.
2. “What does your current remit actually look like; where do you spend most of your time and energy?”
Titles can be misleading. They want to know your true scope:
This helps them benchmark your experience and give a sense of where you’re ready to grow.
3. “In the past couple of years, what are you most proud of and why?”
This is where strategic impact comes to life. Whether it’s steering a crisis, reshaping a brand narrative, integrating comms post-acquisition, or building a high-performing team they’re looking for evidence of leadership, influence, and outcomes.
4. “Looking ahead, what do you want more or less of in your next role?”
A sharp headhunter listens closely here. Are you feeling underleveraged? Are you itching to step into a more visible advisory role? Burnt out from firefighting and ready to build? Your answer reveals where you are in your leadership trajectory and what would re-energise you.
5. “What kind of business, leadership style, or transformation excites you?”
This isn’t just about sector. It’s about fit. Are you most effective in a founder-led scale-up? A complex listed multinational? A highly regulated industry? Do you thrive in moments of change or prefer mature environments with clear frameworks?
6. “Are there any types of roles, sectors, or environments you would rule out?”
Clarity saves everyone time. If there are red flags for you whether it's private equity pace, a lack of senior buy-in, or a sector that doesn’t align with your values say so. A strong headhunter respects boundaries.
7. “What kind of CEO or executive culture brings out your best work?”
This is code for: Will you be able to build trust and influence at the top table? Do you prefer a hands-off CEO who gives you space to lead? Or someone who wants a close, real-time comms advisor? Culture fit at the top matters a lot.
8. “How active is your search and what would it take for you to seriously engage with something new?”
They’re not just testing urgency, they’re calibrating how to position the opportunity. If you’re not looking, that’s fine. But if the right opportunity came along, would you want stretch, stability, brand equity, purpose?
9. “What would make your next move feel like meaningful progress?”
This question cuts to the heart of your motivation. Is it broader influence? A step closer to the CEO? More global scope? A bigger team or budget? The ability to build something from scratch or fix something broken?
It’s easy to default to surface-level answers (title, salary, flexibility). But a thoughtful headhunter is listening for what truly motivates you, what you really value and whether their client can deliver on it.
And one more (often missed):
10. “Are you happy for me to share your CV with this organisation?”
It sounds obvious but it’s surprising how often this question isn’t asked. A credible headhunter will always confirm your consent before putting you forward. This isn’t just a courtesy; it’s about professionalism, control, and trust. You should never find out second-hand that your name is “in play” without your knowledge.
Intro calls aren’t just about being assessed, they’re also your opportunity to understand more about a particular role or perhaps the hiring market. The best headhunter relationships are two-way, built on trust, transparency, and mutual respect. So don’t be shy about flipping the script.
Here are five smart questions to ask them especially if they have a role for you:
1. “How well do you know the client and the comms function?”
You want to know if they’ve worked with the company before, if they’ve placed other roles into the team, or if they’re close to the hiring manager. Depth of insight = quality of advocacy.
2. “What’s prompting this hire and why now?”
Are you replacing someone? Stepping into a newly created role? Supporting a turnaround, IPO, restructure, or growth phase? Understanding the context helps you gauge readiness, risk, and runway.
3. “What’s the leadership appetite for communications?”
This is code for: Will you have the ear of the CEO, or be stuck at arm’s length? A good headhunter should know how communications is perceived internally and how strategically it's leveraged.
4. “What would success look like in the first 6–12 months?”
This helps you understand what’s realistic, what’s expected, and how performance might be measured. It also reveals how mature the thinking is around the role.
5. “Will you confirm before you send my CV to anyone and feedback to me?”
If the headhunter hasn’t already clarified that they will ask your permission then this is a must. It’s surprising how often this is skipped. You should always have visibility and control over where your profile is going and a reputable headhunter will always ask first. They will also never ghost you!
Great headhunters aren’t just trying to fill roles, they’re trying to create matches that stick. When they ask these questions, they’re not looking for polish, they’re looking for insight, clarity, delivery and chemistry. This may mean that they might not be in constant contact but as soon as the right role comes along they will be in touch.
So, the next time you get a call, treat it less like a screen and more like a strategy session. Because the right conversation can unlock the right next move.
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The Works Search: a search consultancy specialising in PR and corporate communications. We have unrivalled matching abilities and are known for finding the top 5% performers in the industry - the ones who deliver and make your reputation great. For more advice or market insights, do get in touch with us on 0207 903 9291 or email: sarah@the-works.co.uk.
