I’ve had the privilege of seeing executive search from both sides of the table. Half of my career was spent at top search firms, helping VC- and PE-backed companies at every stage — from scrappy startups building their first leadership teams to public companies bringing in game-changing C-suite execs. Along the way, I learned what makes searches succeed, what derails them, and how much strategy goes into not just finding the right person, but helping founders get clear on what they actually need.

Now at Bain Capital Ventures, I’m on the other side. I work directly with founders as they build their leadership teams, helping them choose the right search partner and co-piloting the process from kickoff to close. Having seen how different firms operate, I’ve developed a deep appreciation for what makes a truly great search partner. Spoiler: It’s about the person, not the firm. The name on the door might open a few inboxes, but it’s the individual partner who will be pitching your company to candidates and guiding you through the entire process.

With so many search partners out there, each with their own style and approach, it’s worth taking the time to find the one who truly gets your business and your journey. To help you get the most out of your next executive search, I’ll share some of the questions to ask and lessons I’ve learned from seeing both sides.

Why getting help with an executive search is the smart move

Choosing a search partner is one of the most important decisions you’ll make as a founder. Why? Because a great search partner brings the kind of deep networks, speed, and structure you may not be able to access on your own. Before the hiring even starts, they’ll help define what “great” looks like, so you don’t waste weeks chasing the wrong candidates. And when the inevitable bumps come (shifting job specs, board misalignment, a top candidate getting cold feet, trouble closing the deal), they’ll know how to navigate them and keep things moving forward. I was involved in a search where a top candidate backed out days before the offer stage. The search partner quickly reframed the pitch, re-engaged two second-choice candidates, and had one signed within a week. That level of agility only comes from experience and strong market intuition.

So how do you know when it’s time to bring in help? Some cues include an executive search that’s dragged on for months with little progress, a role outside your network, or a process that’s become too much to juggle on top of everything else.

Finding the right executive search partner

Bringing on a search partner doesn’t have to be a slog, but it does take intention. It’s like any other key hire: You need someone who gets your company, your culture, and your vision. When you get it wrong, the costs stack up fast: lost time, wasted money, and, most importantly, lost momentum right when you need it most.

Start by asking other founders, investors, and board members who they’ve worked with and trust. Once you’ve got a shortlist, talk to at least three people. The goal is not just to compare styles, but to see who really aligns with your needs.

Evaluate potential search partners across four key areas:

1. Expertise: Do they have the reach and credibility in the market to deliver for the role you need to fill? If not, can they still map the space thoroughly and hustle to find great candidates? What separates strong partners isn’t their Rolodex, but their rigor. Can they clearly and confidently describe what your startup does to candidates? Can they persuade the best people who aren’t even looking? Do they come prepared with insights or sample profiles that show they’ve done their homework?
2. Track record: Have they closed complex, high-bar searches for companies at a similar stage? If so, they likely know how to adapt as specs evolve and still deliver great talent.
3. Style and process: How hands-on are they? Do they challenge your assumptions and add perspective, or just nod along? A founder I once worked with said that their favorite search partner was “the one who told me what I didn’t want to hear, but needed to.” Ask them to walk you through their process from kickoff to close. Don’t be afraid to dig in. A strong partner should be able to clearly explain their methodology:
   1. How do they conduct research (and who does it)?
   2. How do they map the target market and vet candidates?
   3. How do they handle backchannels and references?
   4. What do their weekly update calls cover? (Hint: Strategy and pipeline unblockers are good answers, not just resume recaps.) Their answers will tell you a lot about how thorough they are, how they pressure-test candidates, and how they’ll represent you in the market.
4. Capacity: You’ll also want to know where you fit into their workload. Ask how many searches they’re juggling and how many dedicated team members will work on yours. When can you expect the first slate of candidates? If it’s more than two weeks after kickoff, capacity might be an issue. And while total timelines for searches vary, clarity and alignment matter more than speed. You’ll get the truest read on this from reference checks.

Ask for:

• A list of past searches they’ve closed for comparable roles and companies
• Founder or CEO references from those searches
• Examples of how they’ve gone beyond their existing network to surface new and nontraditional candidates
• A short list (~5) of benchmark candidates and their take on each. This isn’t about finding perfect matches, but testing how well they understand the role and can articulate trade-offs

By the end of these conversations, you should have a clear sense of who can truly add value and is a fit for your company.

Checking references and staying involved

Executive search firms are great at pitching themselves. But only past clients can tell you how a partner performs under pressure.

When you check references, ask about:

• Responsiveness and transparency: Did the search partner keep the founder in the loop or disappear for weeks? How long did it take to fill the role?
• Candidate quality: Did they deliver the right amount of strong, diverse candidates or just recycle familiar names?
• Level of involvement: Did the partner take an active role in the entire process? How did they handle challenges like pivots in the role or a candidate dropping out late in the process?
• Follow-through: Did they help close candidates, negotiate compensation, and ensure onboarding success?
• Overall satisfaction: Would you work with them again?

Even with a great search partner, you can’t just hand off the effort and hope for magic. The best results come when founders stay engaged. Review candidates quickly, give clear feedback, and keep the dialogue open. The more actively you participate in the executive search process, the better your outcome will be.

When a partnership isn’t working

Even with careful interviews, due diligence, and reference checks, sometimes a search partnership just isn’t the right fit. Maybe the flow of candidates feels off, communication has slipped, or the partner’s judgment doesn’t quite align with yours. When you’re hiring at startup speed, it’s almost inevitable that one of these will happen at some point.

The key is to catch it early and reset. Be direct: Align on clear weekly goals and hold a short checkpoint to see if things improve. If they don’t, don’t hesitate to exit cleanly. Sticking it out usually costs more in time, focus, and momentum than starting over.

If you do relaunch, use what you’ve learned to move faster. Be upfront with the new partner about what went wrong. Strong search partners will appreciate the candor and tailor their approach accordingly.

The right search partner changes everything

When you find the right executive search partner, the entire hiring experience shifts. It feels sharper and more strategic. A great partner brings judgment that cuts through noise — knowing when to push, when to pause, and when to close. They don’t just help you fill a role; they help you raise the bar. The best partners also act as an extension of your leadership team. They help you define what great actually looks like for this stage of your company, and they stick with you until you land a hire you’re genuinely proud of. One of the best partnerships I’ve seen was where the founder said, “I didn’t just get a VP of Engineering, I got a thought partner who helped me rethink our entire hiring philosophy.” That’s what happens when your search partner truly understands your company’s journey.

Look for the executive search partner that will think with you, pressure-test your assumptions, and walk with you every step of the way. That’s when the process is worth every penny.

Good luck!