At some point you decide to bring in a recruiter. Maybe you’ve been trying to fill a role for three months. Maybe you don’t have the time or network to run a real search yourself. Either way, you start talking to firms — and quickly realize that hiring a recruiter is almost as hard as the hire itself.
It’s a low barrier-to-entry business. Anyone can hang a shingle. Logos on a website are easy to collect, recommendations can be curated, and “we specialize in tech” means almost nothing without knowing what’s behind it. A good recruiter sells your company to candidates who’ve never heard of you, in a market where everyone else is also hiring, using nothing but their knowledge and their network. That’s a specific skill — and most people have no idea how to test for it.
So here’s how.
Before You Start Looking
The quality of the recruiter you find depends partly on how clearly you’ve defined what you need before the first conversation. A few things worth getting straight.
How urgent is this? If you need someone in four weeks, that shapes which type of firm makes sense and what you’re willing to pay for speed. If you have runway to do it right, you have more options.
How niche is the role? A senior full-stack React engineer is a very different search from a Scala engineer with low-latency systems experience. The more specialized the requirement, the more you need a recruiter with genuine market knowledge — not just a large database.
What does success actually look like? Speed, quality, and cultural fit are all valid priorities — but they’re not always compatible. Knowing which one you’re optimizing for helps you evaluate whether a recruiter’s approach is aligned with your goal.
Getting clear on these before you start talking to firms will save you a lot of time in the conversations that follow.
Understand What You’re Choosing Between
Recruiting firms generally fall into three categories. Large agencies have big databases and brand recognition — they’ve been around long enough to have placed a lot of people. The tradeoff is attention: you’re one client among many. Solo recruiters often operate more like an embedded partner, working closely with your team but carrying more single-point-of-failure risk. Boutique agencies sit in the middle — smaller, usually more specialized, and often with deeper expertise in a specific sector or function.
None of these is automatically better. The right fit depends on how niche your role is, how much hand-holding your hiring process needs, and how quickly you need to move.
Ask Questions That Expose Real Knowledge
Anyone can tell you they do great work. The way to test it is to get specific about your stack and see how they respond.
If you’re a Python shop building in the e-commerce space, don’t just ask “have you placed Python engineers before?” Ask: which companies do you typically target when sourcing Python talent? Where do the best candidates tend to come from right now?
If your stack is more niche — Scala, F#, something outside the mainstream — the bar is higher. A recruiter who knows this world should know which companies have historically used these languages. Jet.com, for example, was a well-known F# shop before Walmart acquired it. Engineers who worked there are findable, if you know where to look. A recruiter who’s been doing this for real knows that. One who’s been keyword-matching resumes doesn’t.
The same applies to use case. Python for a Django web app and Python for data pipeline work with PySpark are very different roles. A recruiter who doesn’t understand that distinction will send you a stack of resumes that look right on the surface and waste weeks of your time.
Watch How They Qualify Candidates
One of the fastest tells is what a recruiter asks candidates before putting them in front of you.
The most important question any recruiter can ask — and the one that separates the good ones from the rest — is some version of: why are you actually looking? What’s pushing you out of your current role, and what specifically are you hoping to find?
This matters because motivation determines close rate. A candidate who’s passively browsing and a candidate who’s genuinely unhappy and ready to move are not the same pipeline. A recruiter who doesn’t distinguish between them will flood your calendar with first-round conversations that lead nowhere.
If the recruiter you’re evaluating can’t talk coherently about how they qualify candidate motivation — or if they seem to think “they applied” is a sufficient answer — that’s a problem. You’ll run a lot of interviews and make very few hires.
Transparency Is Non-Negotiable
A good recruiter tells you things you don’t want to hear. If your comp band is below market, they say so. If your job description is scaring off senior candidates (a surprisingly common problem), they flag it early. If a candidate is fielding three other offers, you know before it becomes a surprise.
The ones to avoid are the ones who manage you — who tell you everything’s on track until suddenly it isn’t, or who push candidates through because they need the placement more than you need the hire.
Ask directly: what would make you tell a client that a search isn’t working? How do you handle it when you think the client’s expectations are off? Their answer tells you a lot.
Understand the Fee Structure Before You Sign Anything
There are two main ways recruiters get paid, and the difference matters more than most founders realize.
Contingency means the recruiter only gets paid if you make a hire. On the surface that sounds like less risk — but the incentive it creates is to fill the role fast, not necessarily right. You may get volume over quality, and a recruiter juggling five contingency searches simultaneously will naturally prioritize whichever client closes first.
Retained search means you pay a portion of the fee upfront, with the rest due at placement. The recruiter is committed to your search specifically. It’s a better structure for senior, niche, or confidential roles where speed matters less than getting it right.
Neither is wrong by default. But you should know which one you’re in before the search starts — and you should ask how many other active searches the recruiter is running at the same time.
Red Flags Worth Knowing
They ask for your job description before asking about your team. A JD is a starting point, not a brief. A recruiter who doesn’t ask about your culture, your current team makeup, why the last person in this role succeeded or didn’t — they’re sourcing against keywords, not fit.
They can’t name companies they’ve sourced from. “We have a large database” isn’t an answer. Where specifically have they found people like the ones you need? If they can’t tell you, that database is probably older and less useful than it sounds.
They go quiet between updates. A recruiter running a real search should have something to report weekly — pipeline status, market feedback, whether your comp is landing the way you expected. Silence usually means the search isn’t moving.
What a Healthy Engagement Looks Like
Once you’re working with someone, it should feel like a partnership. You should get a brief at the start confirming they understand the role. Regular pipeline updates — even if the update is “we’ve spoken to twelve people and six are worth a closer look.” Bad news early, not after a candidate has accepted another offer.
If weeks are passing without meaningful communication, raise it directly. The best recruiters over-communicate, especially when things aren’t going to plan. If they don’t respond well to that conversation, you have your answer.
Questions to Bring Into Every Recruiter Conversation
Pull from these depending on your role and situation:
- Which specific companies have you sourced [tech stack] engineers from recently?
- Where do strong candidates in this space tend to come from right now?
- How do you assess whether a candidate is actually ready to move — not just open to a conversation?
- How many active searches are you running at the moment?
- Is this search contingency or retained, and why do you recommend that structure for this role?
- What would make you tell me this search isn’t working?
- How do you handle it when you think a client’s expectations are off?
- How often will you update me, and what does that update typically include?
- Can you walk me through a recent search in a similar space — who you targeted, where you found people, how long it took?
You won’t need all of these. But the answers — and the ones that catch a recruiter off guard — tell you most of what you need to know.
If you want to know how we work — or just want a second opinion before committing to a search — get in touch.
