How Executive Search Really Works: Lessons from Somer Hackley for Product Leaders Navigating Uncertain Times

Fireside Product Management

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I rarely read career books cover to cover. But when I listened to Search in Plain Sight by Somer Hackley, I was hooked. It wasn’t a blog post padded into a book—this was the real deal. Structured, thorough, and full of insights that I wish I had twenty years ago.

Naturally, I invited Somer onto the Fireside PM podcast to dig deeper. What followed was a masterclass on how executive search firms actually work, what most job seekers get wrong, and how product managers (PMs) can be far more effective in today’s hiring market.

This post distills our conversation and offers practical takeaways for early to mid-career PMs in Silicon Valley.

1. First, Understand the Recruiter’s Job Is Not to Get You a Job

Most people think executive recruiters are job-finders. They are not.

"Recruiters are filling positions for the companies that have hired them," Somer explains. "Job seekers think recruiters help them get jobs—that’s the No. 1 misconception."

Retained search firms, like Somer’s, work for companies. Their job is to find the top 5 people in the world for a specific role. They aren’t career counselors. If you email them out of the blue asking, "Can you shop me around?" you’re starting off on the wrong foot.

Instead, try this:

* Introduce yourself briefly.

* Acknowledge they may not have a role for you now.

* Ask to stay in touch and offer something useful (referrals, trends, etc.).

Which leads us to…

2. Givers Get Remembered

"The best way to lodge yourself in someone’s brain is when they want to talk to you."

If a recruiter reaches out to you about a role, take the call. Even if it’s not a fit, this is your shot to build a real relationship. Give them referrals. Share industry insights. Offer to help.

Even cold outreach can work—if it’s memorable and has value. But better than cold outreach is being referred by someone they trust.

"Awesome by association is a real thing."

Want to stand out in a recruiter’s memory months or years later? Make yourself memorable and refer great people. That moves you into the "awesome bucket."

3. Shift From Chronology to Clarity

Most PMs walk recruiters through their resumes chronologically. Don’t.

Instead, use the "Think of me when…" framework.

"I view recruiting as journey matching, not just title or industry matching."

What Somer means is this: articulate the kind of journey you help companies with.

For example:

* "Think of me when you’re taking a Series B startup through its first platform rebuild."

* "Think of me when you need a PM to lead a 0 to 1 AI product with regulated data."

Be specific. Counterintuitively, the more focused your ask, the more opportunities you’ll attract.

"If you say you do everything, you're not memorable. If you're specific, people will actually ask if you can do other things too."

Nail your "Think of me when…" and you’ll win more attention and more fit.

4. Build Momentum Before You’re Job Hunting

If you wait until you’re actively looking to reach out to recruiters, it’s already too late.

"Check in once a quarter when you're not looking. Keep doing that. Then 10 years go by and you're top of mind."

Also, don’t expect a quick match. Recruiters have to work with the roles their clients hire them to fill. That may or may not line up with your profile today. So think long term.

5. Your Mindset Is Your Foundation

The hiring process is brutally uncertain. You can be perfect for a role and still not get it.

"It's not always about the perfect fit. Sometimes it's timing, politics, or just who else is in the mix."

So how do you stay sane?

Somer recommends two things:

* Surround yourself with a personal board of champions.

"People who want you to win."

* Use curiosity to stay grounded.

"If you approach things with curiosity, you’ll take the edge off the pressure to impress."

I’d add: don’t take silence personally. If a recruiter ghosts you for two weeks, it probably has nothing to do with you.

6. Be Transparent with Trusted Recruiters

Should you tell a recruiter if you’re not sure about a role? Or if you're juggling other offers?

Somer says yes—if the recruiter seems trustworthy and aligned.

"If I put you forward, I want you to win. So tell me what's really going on. Then I can help position things properly with the client."

Good recruiters aren’t trying to lowball you. They’re trying to avoid surprises that make everyone look bad.

"Let us be your buffer."

The caveat: if you get a bad vibe, trust it. Not every recruiter is great. But when you find one who is, work with them, and be honest.

7. In Final Rounds, It’s About Risk

If you make it to the last stage of interviews, here’s the real secret:

"They’re looking for the safe choice. Not the flashiest."

That means:

* Be likable.

* Be prepared.

* Show you’ve done this kind of thing before.

* Ask smart questions that show you understand what success will really take.

As a former hiring manager at Google, I can confirm: often, multiple candidates are great. The final choice often comes down to small things: a strong reference, cultural fit, or someone who just de-risked themselves better.

8. Own the Compensation Conversation

Somer's advice here was nuanced and spot-on.

* Talk about comp early and often.

* Don’t wait until the offer.

* Create clarity about your expectations and what you’d be walking away from.

"It’s a multi-channel conversation. We're talking comp on the first call, the second, the fourth. I want to make sure the offer you get will be accepted."

Use tools like:

* What offers you’re currently seeing

* What equity you’re leaving behind

* Comp benchmarks from recruiters or friends

And always be clear on your own ask:

"You don’t have to give a single number. Just be prepared with ranges that reflect your walkaway points."

9. Don’t Be Afraid to Ask Hard Questions

Candidates often avoid asking tough questions late in the process. They worry about seeming ungrateful or negative.

But:

"Asking good questions gives the client comfort that you're thinking about this the right way."

Ask about challenges, gaps, political realities. Ask what’s not working. If this role might be yours, you need to know. And you earn respect by showing you want to succeed, not just land the job.

10. After You’re Hired: Stay in Touch

Recruiters who place you can become allies for life. Keep the relationship warm.

"Once you can text someone, it's easy to stay in touch."

You never know when you’ll:

* Build a team and need help hiring

* Be looking again

* Have someone to refer

A short "Thinking of you" or "Saw this post and thought of you" goes a long way.

Final Thoughts

This conversation was packed. If you haven’t already, pick up Somer’s book Search in Plain Sight or listen on Audible. You’ll walk away smarter, more grounded, and better prepared to navigate your next search.

I’ll leave you with this:

“Most people show up saying 'Here’s my bio.' The best ones show up saying 'Think of me when…'”

Let that guide how you introduce yourself from now on.

If you’re navigating your next big career move or want guidance on positioning yourself more strategically, I offer 1:1 coaching at tomleungcoaching.com.

If you’re building out a product org and need help hiring or structuring the team, visit paloaltofoundry.com for consulting options.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit firesidepm.substack.com

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