Getting to Know the Candidate

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After this introduction, your next step should be discovery. Ask questions and listen carefully. If asked with genuine interest, most people will really tell you honestly what they want and are looking for, what makes them a good fit or a poor fit for a role, and their self-perceived strengths and weaknesses. If they trust your intentions, they might also go further by seeking your advice.

Their Direction

It’s important to understand why (and whether) they are actively looking and how serious they are. You might have some prior signal here depending on how you and the candidate connected (for instance, whether they applied to an open position or whether you reached out to them).

As a first step, try to assess their level of interest in your company and your role. BINC co-founder Boris Epstein calls this the difference between “yes, but…” and “no, unless…” Typically, candidates have made some gut call about the job, and are trying to prove or disprove whatever feeling they have. “Yes, but…” candidates are excited about the prospect of working with you, and are essentially yours to lose. But you should understand what questions or hesitations they have. “No, unless…” candidates might be open to exploring the opportunity, but are initially disinclined to take the role.

After discovering their level of eagerness, you should break down that eagerness into two components, one related to their current situation (“going-away”), and one related to your company (“going-toward”). (These are also sometimes referred to as “pushes and pulls.”) “Going-away” candidates have reason to leave or have already left their current job. “Going-toward” candidates are attracted to your role or company specifically. The easiest candidates to recruit will be high on both dimensions. Candidates that are mostly “going-away” candidates might seem very eager to talk, but not for the right reasons. Their eagerness can change for reasons beyond your control, for instance, if they receive a counter-offer from their current company that solves their problems, or if they receive offers from other companies. “Going-toward” candidates may be excited but not willing to move if they’re happy in their current role.

Their Interests

Dig into their past. What have they accomplished, and what are they most proud of? What motivates and excites them? You can often detect a noticeable shift in a candidate’s tone and volume when you hit on one of these chords.

When discussing their interests, some candidates might just take what they’ve read online or seen on your career page about your mission or culture, and regurgitate it because they know it’s what you want to hear. In some cases, this might be to purposely manipulate you and advance their prospects with you. But, of course, they’re not always “lying” deliberately. In many cases, it could just be that the person doesn’t really know what they want, and feel like admitting that could reflect poorly on them.

Sometimes, people aren’t even honest with themselves about what they want. We often make important decisions based on instinct and subtle judgment calls, then confabulate stories that try to make sense of our actions (or are consistent with our own image of ourselves). And, many times, people start their job search with one set of priorities and, as they talk to companies and run through their process, those priorities evolve.

So it’s wise to note that there can be a difference between what someone actually wants out of a job, what they tell themselves they want, and what they tell you they want. It’s your job, by asking the right questions and building trust, to try and work with them to uncover the truth. Some tactics we’ve found to help with this include:

• If they are leaving a job, ask them what would have had to change for them to stay.

• Ask them to design a “dream job” (it doesn’t have to exist). What are they emphasizing?

• Look for consistency between what they’re saying and past and current behavior. In particular, if you’ve built up enough trust and rapport, ask them if they’re OK sharing what companies they’re talking to or are excited about. For example, if they say they care about autonomy and being part of a small team, but they’re also interviewing at really large companies, that might be something worth digging into. If they list companies that are all over the place, that might be an indicator that they don’t really know what they want yet.

It’s also important to gauge interest for the role. For larger companies, this conversation can serve to route the person to the right team within the company, by sussing out the candidate’s motivations and passions. But this only makes sense in certain situations, like if someone has applied and looks talented or is a known talent, is already mission aligned, but it isn’t clear they’re qualified for the specific role that was posted, or you suspect they wouldn’t be happy in that particular role, or if this is an opportunistic hire.

Their Motivations

You will want to explore what’s important to each candidate to get a sense of how they make decisions, and what their motivations are.

• What is their risk profile, and why? This can be both a question of how they are compensated and how willing they are to forgo career stability. A large, mature company may offer more predictability, certainty, and structure. A smaller or unproven company might be more of a risk.

• To what extent are they motivated by a company’s mission, and what types of missions excite them?

• What do they value in a company’s culture or environment?

• How do they view their career development? Do they want to learn certain skills (like a particular tech stack) or achieve certain milestones in the near future (like leading a project) or far future (like starting their own company)?

• Where do they see themselves five or ten years in the future? (This is a good “discovery” question, but also shows that you care about them and not just about filling a role.)

• Are there certain types of challenges that excite them? Why do those types of challenges excite them? Most driven individuals enjoy challenges, but often for different reasons. Some people enjoy overcoming the challenges themselves, like solving a puzzle. Others might feel a sense of fulfillment from the impact they can achieve by solving a certain problem, or from the experience of collaborating or mentoring. Some may prefer a type of challenge because it helps them learn a skill that can further their career.

• Are there practical considerations they care about, like location, commute, work-life balance, benefits like family healthcare, or ability to work from home?

Depending on whether and to what degree a candidate is actively looking for a new position, and how structured their thinking about their career is, they may have very clear answers to these questions: “I’m looking for a fullstack role at a mid-stage consumer internet company.” Other candidates, especially passive ones that you have reached out to, may have a lot less clarity.

Digging Deeper

No matter where it seems like the candidate is coming from, you should dig in deeper to explore why they’re saying what they’re saying. This is another area where a candidate-centric approach will be helpful—it will be easier to have this conversation if the candidate feels a sense of genuine empathy from the other side.

Engineers often use the 5 Whys technique to understand the root cause of a technical issue. You shouldn’t interrogate your candidates, but the mental model of digging deeper by asking “why” can be helpful as you’re trying to understand what drives them.

For instance, let’s take a candidate who says she wants to work at a consumer internet company. Asking why helps you discover whether this work interests her because she wants to work on a product that is used by millions of people, or because she enjoys the type of technology stack and scalability problems that she would encounter. Or perhaps she wants to be employed at a company that her friends or family know and love. Depending on the answer, you can again dig deeper. At some point, you’ll hit a limit of either what the candidate is comfortable sharing or their own self-awareness. But the more you understand their needs, the better.

Practicalities

Finally, there might be some more practical questions you should cover. Does the candidate’s work-authorization situation match what your company can provide? For instance, if they need visa sponsorship, is that something your company is able to do?

What is their timeline like for making a decision? Are they close to getting offers from other companies or do they have to make a decision by a certain date?

Depending on your rapport with the candidate, this may be a good time to talk about compensation.