You’re reading an excerpt of The Holloway Guide to Technical Recruiting and Hiring, a book by Osman (Ozzie) Osman and over 45 other contributors. It is the most authoritative resource on growing software engineering teams effectively, written by and for hiring managers, recruiters, interviewers, and candidates. Purchase the book to support the author and the ad-free Holloway reading experience. You get instant digital access, over 800 links and references, commentary and future updates, and a high-quality PDF download.
While the typical interview loop begins with a screening process, a more general first conversation is usually appropriate for outbound candidates, referral candidates, high-value candidates, and when hiring for senior positions. You may have exchanged a brief amount of information over email, or they’ve submitted an impressive application and you want to start with something more personal or intimate than a phone screen.
For this conversation, most companies will schedule a 30–60 minute call with the hiring manager, founder, or recruiter, depending on the size and stage of the company. For high-value candidates and where time and location allow, it might be more effective to try to do this in person, and for the manager or founder to reach out rather than a recruiter.
If the candidate is a referral, is a known quantity in some other way, or has done the exact job you’re looking to fill, you might have one of these calls with them to begin selling them and make a personal connection, and put them in the right pipeline. The general phone call at medium and large companies is sometimes conducted by a recruiter. The goal is simply to have a verbal touchpoint—likely the first—after some communication has taken place over email.
The purpose of this conversation is threefold:
Selling the candidate on the company.
Routing the candidate to the appropriate role or team if it’s unclear where they’d make the best fit.
Gauging their interest in the role, team, and company.
There are no hard and fast rules for going about this, other than to think of what helps build the mutual understanding and trust that could lead to a successful hire.*
Goals and Pitfalls
For many busy and distracted hiring managers, a first conversation with a candidate may feel like a way to quickly determine if someone is a fit, and rule out poor fits quickly, much like a technical phone screen.
We suggest taking a more thoughtful, candidate-focused attitude.* Approach every first conversation with the intention, “How can I best help this person?” At its core, hiring is about building deep, trusted relationships. Directly optimizing for the candidate’s outcome (how can I help them be successful?), particularly at this early stage, leads to the best long-term outcome for your company. So start by putting the candidate first. Treat them as you’d want to be treated, or how you would a future teammate. Think about the long term. At this point, some hiring managers might scoff. “This is idealistic! It’s impractical! We’re crazy pressed for time over here!” In reality, this candidate-centric approach is the best way to ensure strong fit, longevity of employment, and a number of other pragmatic hiring goals:
Maintaining the efficiency of your pipeline. One important function of this first conversation is to prevent yourself from investing more time if there obviously isn’t going to be a fit. If you’re being considerate of the candidate’s time, you’ll find yourself more effective with your own time as well.
Getting the candidate more interested in your opportunity (if it makes sense). You’ll be able to build a solid rapport with the candidate, since you’re looking out for their best interest. This can help now (by encouraging the candidate to explore your opportunity) and in the future (you’ll more likely be able to convince them to join if you extend an offer). If things don’t end up being a good fit at the moment, you’ll have built an important relationship for the longer term.
Determining the best fit for candidate within the company. By really understanding the candidate, and putting them first, you might be able to better match them to a different role at your company.
A candidate-centric approach will make you more successful at reaching all of these goals. You’ll engage in the conversation with a more curious mindset and avoid some of the more transactional dynamics that plague recruiting today.
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caution It will also help you avoid some common pitfalls:
Avoid hard selling. A common mistake is to try and convince a candidate to engage in your recruiting process without really understanding what they’re looking for. This can be a strong turn-off and deterrent for candidates. Even if your sales pitch works, and they continue for now, they’re more likely to withdraw later.
Don’t spend the entire time assessing the candidate. It’s easy to assume that the goal of that first conversation is to dive into immediately assessing the candidate’s skills and experience, but you shouldn’t do that until you and the candidate both understand each other’s needs and goals. There are other opportunities before and after this touchpoint to assess the candidate’s skills.
Don’t be too scripted or transactional. This can rightfully turn candidates off and cause you to miss opportunities for engaging them on their interests and talents. For instance, maybe the candidate would be a great fit for a different role or team at your company, but if you’re too scripted, you’ll never get a chance to explore that possibility.
dangerBroadly, you want to avoid two negative outcomes:
Force-feeding your pipeline. Trying to push a candidate forward to the next stage in your process prematurely might feel like progress, but ultimately, can be inefficient both for you and for the candidate. You might not truly understand the candidate’s needs and priorities only to discover them later on in a downstream stage. You might also miss opportunities to match them with a better team or role.
Providing a poor candidate experience. It is a truism that first impressions last and are hard to change. If your first interaction with a candidate feels inauthentic, transactional, or adversarial, it will be difficult to change that impression later on in the process—if your candidate makes it that far.
Recruiting can be a grueling process on both sides of the table; it can even get adversarial at certain times. We don’t think it should be that way. Taking a candidate-centric approach can make the overall process both more humane and more effective. It will make the time you spend on recruiting a lot more fulfilling—which, as an added bonus, will make it easier for you to dedicate more time to it.
By putting the candidate’s needs first, you might find that after one or two first conversations, you end up telling them that you don’t think you can offer what they are looking for, or you may even introduce them to a different company that can be a better fit. That’s OK. It’s better for both you and the candidate, especially in the long-term.
Getting Into the Right Mindset
It’s easy even for people with the right intentions to revert to a more transactional, “let’s get down to business” attitude when they jump into a call with a candidate. To avoid that, we’ve found it helpful to take a few minutes before any call to get into the right mindset.
Timing can make this task easier. Try to buffer some time before every call to mentally prepare. You should also schedule calls for the time of day where you will have the most focus and energy to devote to candidates. Try to avoid times when you might be stressed, drained, or crunched for time. In particular, doing several back-to-back recruiting calls might make it more difficult to maintain focus.
caution Make sure that during your call, you are solely focused on the conversation. If the hiring manager or recruiter is reading and responding to emails or checking messages during the conversation, it’s disrespectful of the candidate and will reduce the value of the call.
Building Rapport and Trust
Take the time at the start of a conversation to humanize yourself to the candidate and make the process—and your company—seem less alien. Ask how the candidate is doing. Be friendly and considerate, and note whether the candidate seems nervous.
Next, introduce yourself and talk a little about your background. Briefly sharing a few personal details or stories can help put the candidate at ease. This can also be a great point to mention why you are at your company. The candidate will remember that you, too, were once just starting out in a new position.
As you begin to develop some trust and rapport with the candidate, try to form a connection. For instance, you might find some common ground, like an aquaintance you share or a favorite band. Maybe you used to travel through their hometown. Just a small connection can put the candidate at ease. Alternatively, you can try to note something unique or interesting about their background and bring it up. “So I heard you used to roadie for Black Sabbath. Did you learn to code on the tour bus?” A little prior research can help here.
After these opening lines, maybe a laugh or two, explain the purpose of your conversation. For a first conversation, you’ll say something like, “Today is a chance for us both learn a bit about each other and better understand each other, and explore whether there might be a fit.” This is where your candidate-centric approach can really show. If this meeting has a specific agenda, let them know what to expect.
important This conversation may or may not be around five minutes. With a shy or nervous candidate, you might spend more time chatting and making them feel comfortable. If you’ve already had a chance to build rapport (over email or if you met at an event), you could spend less time in this opening conversation. The candidate may also just not be willing to get into too much small talk; you don’t have to force them.
Getting to Know the Candidate
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.
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.
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.
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.
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.
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.
Next, it’s your chance to express your company’s value proposition to the candidate and answer any questions about the company or the role that they may have. You have built a compelling narrative for the company and the role, and have learned enough about the candidate to communicate the opportunity to them in terms of what they value. Without being pushy, scripted, or salesy, you have to remember that the candidate is meeting the company through you; you and the company are being interviewed too, so you want to put your best forward.
Begin by asking the candidate what they know about the company. This can serve as a good transition between getting to know them and talking about the job. It will also prevent you from repeating things they already know, or overwhelming them with detail too soon. Based on how much they already know, and what they think they know, you can begin talking about the company and the role.
While you might have a general backdrop that you use for this part of the conversation (something about the company or its history that you like to focus on, some theme or part of the mission that you personally connect to, or something else), it’s helpful to customize your script based on what you now know about the candidate. Connect dots that they might find appealing (or better yet, let them connect the dots). This is where having more than superficial knowledge of the candidate helps.
For instance, let’s use our candidate who said she wanted to work at a consumer internet company. If that’s all you know, and you’re recruiting for an enterprise company, you might hit a dead end. But if you know that the candidate is interested in consumer internet companies because of the scale, and your enterprise company also has interesting scalability challenges, that is something you can focus on.
Finally, it might be worth proactively volunteering any areas where the dots don’t connect, and asking them if that might be a problem. For example, if they mentioned that they prefer technical challenges to working on user-facing products, which is important to the role you’re filling, ask them how they feel about that potential alignment issue. This is another point where empathy can serve your interests in a way that might seem counterintuitive. If the candidate responds that a certain attribute of the role or company might be a deal-breaker, that’s actually helpful—you’ve caught the deal-breaker early on in the process. If, instead, the candidate starts selling the role to themselves, that’s a great sign. They might be connecting the dots in a way that you weren’t able to.
Evaluation and Next Steps
If you’ve covered everything in the previous sections and the conversation has gone well, you may not need to ask the candidate further questions. You’ve already spent time understanding what the candidate values and what they have worked on in the past, so you may already be able to tell whether they would work well with the team or have the particular skill sets required by your role.
If you feel like you do have a few specific questions you need answered, now’s the time to ask. But the less evaluative you can make the first conversation feel, the better. Leave the technical grilling for later, when both you and the candidate have more explicitly opted-in to continuing the process.
At this point, there is a menu of options, and you have to pick one:
Advance. If the candidate seems like a fit for the role, and has shown genuine interest, you can advance them to the next stage of your funnel.
Pass. If the candidate is not a fit, and would most likely be rejected further in the process, you probably shouldn’t move them along. Don’t waste your time or the candidate’s. If you can still help the candidate in some way, easily, this is always a good thing to do! If you know another company where they might be a good fit, tell them.
Explore other roles. If the candidate is not a fit for the specific role, but could be a fit at your company, is there another open role at your company they might be a fit for?
Deepen the relationship. If the candidate is a fit, but you’re not confident they are genuinely interested, you shouldn’t move them forward yet. There are a few options here:
If you believe you know what their reasons for lack of interest are, and that you can overcome those concerns, you can introduce them to someone else at your company. For instance, if they aren’t sold on the technical challenges, you can have them talk to another engineer on the team. If you’re a startup and they aren’t sure about the company’s potential, you could put them in touch with one of your investors.
You can try to maintain a long-term relationship with them.
If the outcome of the decision seems obvious to both sides (for instance, you both agree there is not a fit at the moment, or you both agree to move forward), some hiring managers or recruiters will communicate that immediately at the end of the call. But this requires experience and finesse, so we usually recommend following up with the decision later.
important You need to set expectations for the rest of the process. Most people are stressed about uncertainty more than anything. While you can’t guarantee the candidate that they will get an offer (or even move forward past this point), you can remove some uncertainty by explaining what the process looks like and what the timeline might be. In other words, while the outcome might be uncertain, you can add certainty around the process and timeline.
Even if you feel like you have made a decision, delivering that decision a little later can help in a few ways:
You don’t want to rush into a decision. You might change your mind after reviewing your notes, talking to your teammates, or just sleeping on it.
If you are rejecting the candidate, it might be better to do it after the stress and adrenaline of the call has worn off a little bit.
Of course, never leave a candidate hanging for more than two or three days before delivering a decision, whatever it may be.
For candidates who will be moving through the process, this is a great place to establish a few elements that will help you maintain a great candidate experience and be well-situated to close a candidate should you end up extending an offer.
First, establish someone on your team to be the candidate’s confidant. The candidate should have someone that they can reach out to if they have questions or concerns during the process. At larger companies, this is often a recruiter, but it may be someone else at the company. Either way, the confidant should be someone that the candidate will feel comfortable talking to without risk of hurting their future working relationship (in other words, usually not the hiring manager). The candidate should really trust that they can talk openly to the confidant, and that the confidant will be quickly responsive, available to reply to emails or hop on the phone at short notice. The confidant is important throughout the process, but perhaps will be most critical at the offer stage.
Second, make sure you (or someone on your team) maintains a regular cadence of contact with the candidate to stay top of mind, keep them engaged, and find out if there are any updates from their side. This can involve sending them updates about where they are in the process, or sometimes just sharing exciting milestones or announcements from your company. If, at any point, a candidate is confused about where they stand or is reaching out to you for updates, you’ve probably done something wrong; either you haven’t set expectations with them about the timeline, or you’ve set expectations and failed to meet them. It can be a good idea to have regular pipeline review meetings with your team, to check on the status of everyone in your pipeline and make sure no one is “stuck” or hasn’t been communicated with in a while.
This cadence should increase as a candidate progresses through your pipeline. For instance, initially, while the candidate is early in your process, you might be communicating with them on a weekly basis to check-in and build trust and excitement through repeated interactions. By the time you have extended (or are close to extending) an offer, you might aim to have a touchpoint every couple of days.
important Many companies lose candidates because they aren’t in close contact with them, especially if they are in the pipelines of other companies and receive competing offers.
Nurturing for the Long Term
For positive candidates that you won’t be putting through the process, either because you don’t have a suitable role or the timing isn’t right for them, it’s valuable to try and maintain a long-term relationship.
For candidates who aren’t fully convinced they’d take the job (or, if you’ve sought them out, have not formally applied), maintaining contact could help you sway their opinion of your company, or catch them at that serendipitous moment in the future when they are open to switching. On the other hand, maintaining a relationship with candidates who you don’t have a current role for can be very valuable in the future by saving you the time and cost of having to build a pipeline of candidates from scratch whenever you open a new role. In either case, these relationships can accrue other dividends, for instance, these candidates might refer other candidates to you.
How you maintain these relationships will differ. It might entail a simple check-in email every few months, perhaps coupled with some updates or announcements about your team and company. Other ways to maintain contact could be giving them early access to parts of your product (if it’s a product they would use) or inviting them to events (if you’re hosting events at your company). You might connect with them on LinkedIn so that they can see when you post company updates. For higher-value candidates, you might take a higher-touch approach, by meeting with them every few months to get coffee and catch up. If you’re really aiming to build a trustful relationship with the candidate, you might offer access to your network or an intro to another recruiter or company that might be a better fit for them right now.
Whenever I meet a candidate at the top of the funnel, my only goal in that conversation is to do right by the candidate. I take this to an extreme. During our conversation, if I know that my company is not right for this candidate I let them know of another company who is [a] better fit and I make the necessary introductions. My take is that if you have discovered that with Dropbox for example, productivity software is not what the candidate really wants to work on, why would you want them in the company? Instead, do right by the candidate and pay it forward. You’ll be surprised by the network you end up building. Every one of the candidates I’ve referred to a different company has sent me someone else in their network that is a better fit for my company.Aditya Agarwal, former CTO, Dropbox*
caution If a candidate isn’t interested in maintaining a relationship with you or your company, don’t try to force it. Never spam candidates or overwhelm them. When in doubt, give candidates a polite “out.” For instance, your emails could mention that while you’re reaching out because you want to maintain a relationship, you’d be happy to just let them reach out themselves when things change on their end.
important Note that nurturing for the long-term can be important for candidates all along the funnel, not just at the beginning, who enter your process and aren’t suitable for the job or self-select out. Even candidates who have made it all the way through the process and ultimately don’t receive a job offer from your company (or don’t accept an offer) can be valuable assets in the future—and rather than pretending they never existed, continuing to stay in touch with those you respect and admire is the right thing to do.
Companies assessing candidates. Once candidates have passed through the top of the funnel, companies need to gauge candidate-company fit based on deeper skills assessment; suitability for the role, including values alignment; and the candidate’s interest in the role, team, and company. In some cases, a candidate will not be screened at the top of the funnel; this occurs most frequently with senior candidates and referrals, whom the company will get to know first through more casual interviews.
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