Full Strategy: How to Work With Headhunters

The executive search world is often painted as an elusive network of trusted intermediaries connecting top talent through quiet conversations. But the reality is often very different. For every reputable headhunter with genuine insight and access, there are grifters and rug merchants who will lead you down a path of wasted time and wasted opportunity.

The executive search business is unregulated, and anyone can call themselves a headhunter. Some are highly professional and deeply connected, but others are nothing more than opportunists, peddling half-truths and hollow promises in order to serve their own self-interests.

A well-timed call from a great headhunter can transform your career, and they can absolutely be a highly valuable asset. However, you need to tread carefully and with eyes wide open.

The most important thing to appreciate is that a headhunter does not work for you. They are paid by their client, the employer. That doesn’t mean they aren’t interested in placing you - they want a successful match - but it does mean that you need to be fully aware of where their interests and motivations lie.

The savviest executives know that the most profitable way to engage with headhunters is as a complement to their own proactive efforts, never a substitute.

What is a Headhunter?

Recruitment comes with a confusing array of titles: headhunter, executive search consultant, recruiter, executive recruiter.

Is there a difference?

While there are nuanced distinctions, the term 'headhunter' is generally used nowadays as a colloquial catch-all. In short, anyone who actively seeks out candidates for a job, particularly for high-level or specialized roles. They are a third party, with the employer paying the bill.

To complicate matters, companies also employ their own in-house recruiters under the HR or Talent Acquisition function, but I'm not focusing on those here - they require a different strategy.

Headhunters are then broadly split into two main camps, and it’s crucial to understand the distinction, because their motivations and how they operate dictate their relationship with you.

Retained Headhunters

• How they work: Retained headhunters are hired exclusively by a company to research, assess and present candidates for a specific role. They’re paid upfront and in instalments, regardless of the ultimate outcome. A retained engagement is comprehensive, with quality and fit prioritized over speed.
• Motivation: Their loyalty is tied firmly to the company they represent. They are paid whether or not the role is filled, but their focus is on finding the best fit for their client and upholding their reputation for future business.
• Impact on you: Retained headhunters can have access to great positions. However, they won’t advocate for you unless you are a perfect fit, and may not have the time or inclination to talk if you fall outside of current engagements. They are not motivated by hiring you specifically, and you will be presented as part of a shortlist of other candidates.

Contingent Headhunters

• How they work: Contingent headhunters are paid only if the company hires a candidate they’ve presented. They generally work on a non-exclusive basis with their clients. This means multiple firms may be competing to fill the same role, and speed often takes priority.
• Motivation: Their incentive is to get paid, and they need to present candidates before their competitors to secure their fee.
• Impact on you: While they can give you access to a broader range of opportunities, you will typically be competing against multiple candidates from both them and their competitors. A lot of their work is speculative, and they may not even have terms signed with companies they are sending your resume to. Your resume may be solicited to multiple companies and you can lose all control of where it’s gone and who’s seeing it. Tread carefully.

Managing the Relationship with Headhunters

To maximize your value and maintain leverage, understand that every interaction with a headhunter should be treated as a professional transaction. Approach every new relationship with your eyes open.

Do Your Due Diligence

Before divulging any information to a headhunter, do a bit of fact finding to weed out the wheat from the chaff.

Ask them:

1. Are you working on a retained or contingent basis?
2. Are you working exclusively with the client?
3. Who is the client?
4. How long have you been working in [X] industry?
5. How many similar roles have you placed?
6. Why did you call me specifically? (A good headhunter will have a feel for your background and profile and why they think you are a good fit for their client)

Judge the headhunter. Listen to how they are talking about the role and their client. Read between the lines.

Look for red flags:

Overpromising Without Substance

• What to watch for: Grandiose claims about exclusive access to top jobs in your industry or an assertion that you’re the 'perfect fit' for multiple roles without understanding your background.
• Why it’s a problem: Overpromising often signals a lack of real connections or desperation to fill their pipeline.

Lack of Industry Knowledge

• What to watch for: Vague or generic answers when discussing trends, roles or companies in your sector.
• Why it’s a problem: A good headhunter knows their market inside out. Inexperienced or opportunistic recruiters may lack the expertise to represent you effectively.

Pressure to Act Quickly

• What to watch for: Pushing you to accept a role or move forward in the process without giving you time to evaluate the opportunity.
• Why it’s a problem: Pressure tactics are often used by contingent recruiters eager to close a deal, regardless of whether it benefits you.

Submission Without Consent

• What to watch for: Sending your profile to a company without informing you or gaining your approval.
• Why it’s a problem: This is a major breach of trust and can damage your reputation if your profile is submitted to companies without your knowledge.

No Transparency About the Role

• What to watch for: Refusal or reluctance to share key details about the client, the role or the hiring process.
• Why it’s a problem: Vagueness often signals inexperience or a lack of genuine access to the client. This particularly common in the contingent space.

Focus on Volume, Not Fit

• What to watch for: Emphasizing the number of roles they can put you forward for rather than taking the time to understand your unique skills and goals.
• Why it’s a problem: Quality matters far more than quantity. A volume-driven approach often leads to mismatches and risks damaging your professional reputation. They are speculatively spamming the market.

Limited Access to Decision-Makers

• What to watch for: Inability to demonstrate a direct relationship with the hiring company or its leadership.
• Why it’s a problem: A headhunter without access to decision-makers is unlikely to have a commercial relationship with that company. Any submission will be speculative.

Transactional Mindset

• What to watch for: Focusing solely on closing the deal, with little interest in your long-term career trajectory.
• Why it’s a problem: This approach is a hallmark of grifters and inexperienced recruiters who view candidates as commodities rather than professionals with unique value.

Stay Guarded But Professional

• Never disclose compensation: If you reveal your current or expected compensation it can set an artificial cap on the offer you receive. Headhunters may use this information to position you as a lower-cost candidate, undermining your potential to negotiate for higher compensation. Regardless of how much they push, politely decline. Ask them for the salary range to decide whether you want to pursue it (though remember that ranges can always be broken), but refrain from agreeing that the range is in line with your expectations. Just say “I’m happy to proceed with discussing the role in more detail - we can talk numbers when it comes to the offer stage”. 
• Treat all communications with headhunters professionally: Avoid getting too personal or disclosing information that could be used against you in negotiations or could pigeon-hole you. Anything you say can and will get fed back to their client.
• Career goals and flexibility: While it’s important to be clear about your aspirations, disclosing too much can weaken your negotiating position. Headhunters may see you as overly eager or willing to compromise, reducing the incentive for a strong offer.
• Your resume: Don’t share your resume until you have a full understanding of the role, and how you can tailor it to the specific problems you are there to solve. That involves speaking with the hiring leader first, so push for a conversation. However, that's not always possible, which is one of the drawbacks of working with a headhunter. Do not give permission for them to solicit your resume to any companies unless you have specifically agreed to it. 

Control the Narrative

• Set Expectations: Be clear about your career goals without locking yourself into specifics. Leave room for negotiation.
• Close them on next steps: Book in the next call/meeting or stage before you get off the call with them.
• Get to the hiring leader as fast as possible. Your ability to both demonstrate your value and negotiate comes with speaking to the hiring leader. Push for a meeting or call.

Gather Intelligence

• Headhunters are a great source of information about the market, the company and its leadership. The more you know, the stronger your position when it’s time to negotiate.

Know When to Walk Away

• If a headhunter is pushing you into roles that don’t align with your long-term goals, be prepared to step back. Working successfully with headhunters is about building mutually beneficial relationships, not feeling pressured into compromising your career.
• Don’t let a shiny role cloud your judgment if you are getting red flags from the headhunter. 

Leveraging Multiple Headhunters

It’s perfectly acceptable to work with multiple headhunters, especially if you’re targeting different industries or regions.

However, never disclose to one headhunter any information that you’ve received or shared with another. Discretion is key. Do not discuss the role, client or any specifics beyond “I have been approached about a number of opportunities”.

Keep your approach discreet and professional, maintaining control over your narrative and information.

Building a Long-Term Relationship

There is a lot of value in building long-term, trusted relationships with good headhunters who operate in your sector. Beyond access to opportunities, they can be an excellent source of market intel.

Even if you're not actively looking for a job, it's worth staying on a headhunters’ radar by occasionally checking in or providing referrals.

This helps position you as a valuable contact, whether or not you are in immediate need of a new role. You will be their first call when good opportunities come across their desk. As a headhunter, my first question on any new role is who do I know?

The Bottom Line

Good headhunters can open doors and provide intel and access that's otherwise hard to get, but they should never become a crutch.

The reality is that headhunters are reactive. They come to you when they have a role to fill, and waiting for their call leaves your career at the mercy of someone else’s priorities and timeline. Even the best headhunters are constrained by the scope of their client briefs, often leaving little room for you to shape the terms or trajectory of the role they offer.

Executives who depend too much on headhunters risk falling into a passive stance, allowing their careers to be defined by the opportunities others bring to them. This is a critical error.

The most successful leaders take ownership of their narrative, leveraging their networks to uncover opportunities long before a headhunter gets involved. They build relationships with decision-makers, maintain visibility in their industries, and create roles that align with their goals rather than fitting into pre-defined boxes.

Knowing this, you should strongly consider how much effort you should direct at working with headhunters.

That said, always take the call. You don’t know where it will lead.