002. How to conduct interviews so good, candidates will thank you for rejecting them
The obnoxiously, scarily authentic way to hire
After the widespread uncertainty and hiring freezes of H1, we’re finally seeing signs of defrost, And once again, my inbox is starting to fill up with startup founders looking for help in recruiting and People Ops.
So Workflow is hiring for the first time in a while! These days, the way I recruit is more indirect, via consulting/teaching – so the hiring nerd in me could not be more excited to step into the arena myself.
And I genuinely *love* hiring – especially interviewing. My years of experience as a recruiter has trained me against my deeply introverted nature, and actively choose to see interviews as opportunities to connect with wonderful people.
So this week, I’m sharing some of principles that make up my unique approach to Interviewing, which results in pretty unusual candidate feedback:
Candidates are genuinely grateful after being interviewed (and even rejected) by me. Perhaps it’s a strange thing to be proud of, being great at turning folks down, but I am – because this is what great hiring is supposed to be like. Many of us have forgotten that, if we’ve ever been exposed to it at all.
In this post, I’ll peel back the curtain on my interviewing philosophy, the 3 principles it entails, and how, even if your style isn’t exactly like mine, putting these into practice will help you become a great interviewer.
The Set-up: Great screening is a prerequisite for great interviews
Principle 1: Great interviewers let go of trying to control outcomes
Principle 2: Great Interviewers are warm and present
Principle 3: Great Interviewers are collaborative in finding a mutual fit
The Set-up: Great screening is a prerequisite for great interviews
Before we talk about interviewing, first we have to cover screening. It is impossible to be a great interviewer without effective screening.
This is probably the #1 mistake I see startup founders with hiring. First-time founders especially assume “Recruiting” as only the times when you’re actually face-to-face with a candidate. Often, this is the effect of having come from a larger company where Interviews were the only slice of the recruiting cycle they were exposed to, with little idea of the complexity of the backend systems.
So, a common complaint from founders sounds like this: “Interviews are such a waste of my time. I’m constantly getting on the phone with candidates and right away know it’s not a good fit.”
This is an understandably frustrating dynamic, but blaming the candidate (“That person was terrible”) and/or blaming the act of recruiting itself (“I hate interviewing”) will have you missing out on a critical lesson:
Screening candidates to interview is *your* responsibility, not theirs. If interviews consistently seem to be a waste of time, that means your team’s filters aren’t calibrated, and people who should be screened out earlier are passing through. That is not the candidates’ fault, but an opportunity for *you* to look inwards and identify the missing screening criteria.
There are many possible screening tools at your disposal, such as a truly excellent Job Description that draws the right candidates in, and the wrong ones out (a topic for another day). Another tool I’m a big proponent of, and not utilized well by most startups – is Application Questions.
Applications Questions are 1-3 simple prompts for candidates when they first apply that surface critical screening data. For example, if asked “In 1-2 sentences, what are you looking for in your next role?” or “What’s one thing you’re learning right now?” and the candidate’s written answer is messy and unintelligible – their answers will likely be messy and unintelligible on Zoom as well. It’s not a perfect screening tool, but it is pretty damn effective.
Here’s an example from my own hiring process: As the Founder/CEO of Workflow, I look for self-awareness and an orientation toward self-improvement in my potential team members. So our application asks the following: “What would you say your top 2 strengths are? How about 1 thing you're currently improving on?” The answers tend to be VERY illuminating, those who provide thoughtful, self-reflective answers tend to be the ones I’m most excited to meet in an interview. This is just one example of many, many potential screening strategies, as the most effective ones will be custom to your specific context.
The point is, effective screening allows you to spend your time with the most promising candidates, which is foundational for the following set of principles.
Principle 1: Great Interviewers let go of trying to control outcomes
Imagine you’re walking into a first date, and you’re saying to yourself, “Oh god, I’m ready to get married right now, and this person better be IT. Otherwise, this will be a waste of my time.” It will 1) be very hard for you to enjoy yourself on this date, and 2) the other person will probably sense the pressure, making it harder to find a good fit.
Hiring is just like dating in that way – the pressure is *thick* in the air, especially in startups where hiring can truly make or break the company.
This kind of striving ambition – which may serve you well in other areas of your life, you go-getter rockstar you – might also lead you to come across as guarded, antagonistic, or transactional in interviews. Counterintuitively, being able to relax and focus on the experience, not trying to control outcomes, increases your chance of success.
Whenever I hop into a Zoom for an interview, I take a few seconds to remind myself that I am excited to meet a new person, that I am grateful that we’re choosing to take time out of our schedules to come together – and that while we both hope for good fit, it’s ok if not.
Try on this mindset for a while, and if it doesn’t feel natural and interviews are still too painful, go back to the previous section to revisit your screening criteria.
Principle 2: Great Interviewers are warm and present
Most of us walk into interviews pretty distracted, scrambling to context-switch from the previous meeting and glancing at the resume. But much like bringing an open and curious mindset, being present is another critical element of advanced-level interviews.
Presence allows me to truly listen and empathize with each candidate, just as I would with a friend. When someone mentions getting laid off, I respond empathetically (“I’m so sorry, that must have been really tough”) – and mean it. When another candidate noticeably lights up when talking about a topic, I lean into the curiosity and ask follow-up questions, to deepen my understanding of who they are (“You seem really passionate about X! How did you first get so interested in it?”).
From the candidates’ perspective, interviews feel like being under a microscope. So interviews that contain just a little bit of genuine human connection are a refreshing, pleasant surprise (as my colleague Lauren would say, the “The bar is lower than hell”).
It’s easy to forget when you’re on the “Company” side of the table, but being a job seeker is an incredibly vulnerable position. They’re putting themselves out there, so as interviewers, the least we can do is to listen and demonstrate active engagement and creating a supportive environment (e.g. smiling and saying “that’s really awesome!” when they share an accomplishment).
Presence is the foundation that builds trust. With every candidate that I meet, I genuinely wish them well in their career journey – and they can feel it. Embodying this level of authenticity might not happen overnight given that it’s a pretty radical shift from today’s standard, but practicing it will open up new possibilities. Again, if this feels too hard, go back to the previous step and revisit reducing pressure and attachment to outcomes.
And that leads us to…
Principle 3: Great Interviewers are collaborative in finding a mutual fit
There’s no shortage of reasons why candidates dislike the interviewing experience, but a key one is that it’s a black box. The job search process entails putting on a song and dance, waiting for a few tense days (if you’re lucky – weeks if not), then getting rejected via a cold, templated email. Repeat up to dozens of times.
But there’s another way, and it’s to host collaborative interviews, where the candidate is invited into your thinking and decisioning.
During each interview, I listen deeply about their skill set and what they’re looking for. Most people are actually very honest, especially if you can ask questions in a supportive way and invite them into an honest discussion. Some recent examples:
Candidate A seemed (understandably) spooked after getting laid off recently. Noticing this, I offered an empathetic comment and gently pushed on it: “I totally get it, I love the opportunities of early-stage startups too. But there’s been phases of my life where I needed more stability. Given what you’ve recently gone through, how are you thinking about the role of risk in your next chapter?” The candidate paused for a moment, and admitted they’re probably needing more stability than an early-stage startup. Upon this, I could see a weight getting lifted off their shoulders, and we discussed how this might not be a mutual fit, which made the candidate visibly relax further, and they were grateful for helping them come to the realization.
Candidate B had recently left a long tenure at a notoriously chaotic hypergrowth company, and just seemed spent. I told her, “What you accomplished at X is truly incredible – especially given the scale you had to grow, and with so little support too.” Then I asked, “I imagine it might be hard to get re-connected with what *you* want after such a long sprint, but I’m curious – what would your *ideal* next role look like?” This frame invited them to not “sell” themselves against the opportunity at Workflow, but to put the focus back on what *they* want – so they’re more likely to find what they really need. She mused that their ideal next step is probably at a bigger company, where she can hold a little less responsibility and recover from burnout. This way, we came to the conclusion that it’s not a good fit collaboratively.
Opening up these conversations is delicate, but I’ve found most people respond incredibly well to invitations to be self-reflective and share out loud. It might be my background as an executive coach, and perhaps what I’m doing is creating mini-coaching moments.
It takes listening deeply for my own curiosities (“Is this person X enough? Ready for Y?”), offering the most empathetic/charitable framing possible (“I can totally understand given X…” “Sounds like Y might be really important to you, so it makes me curious whether Z…”). Then, actually talk it out together! Maybe the candidate’s response reassures me about the concern (or even more alarming, lol). I carefully note if they can see my perspective and accept the feedback (even if they disagree with it), or if they get defensive. All of that is information – as what I’m really doing is running a mini simulation of what it would be like to actually work together.
For candidates, being offered a key piece of feedback or insight, and an exploration space around it, can be more valuable than a job offer itself – because being seen is a gift, and it points them in the right direction. Maybe that sounds corny, but I truly believe that, as the candidates I’ve interviewed and turned down have told me so.
Putting it all together, for the interview’s dramatic conclusion
As you may have gathered, my approach to interviewing allows me to determine Yes/No for next steps by the end of the call. And if it’s not a good fit, I tell them. Yes, during the call. A live rejection.
But I’m no Simon Cowell, reveling in putting people down. Delivering live rejections is a delicate skill, and categorized as “Advanced” level for a reason. It is NOT recommended for most people – bungling it results in immediate feedback, in the form of both you and the candidate feeling pretty terrible! Still, it’s worth knowing what is possible.
I told a recent candidate, “This has been lovely getting to know you, and it’s clear how much you care about good People work and we have that in common. At the same time, I’m hearing that you’re in a more exploratory space, wanting to broaden out possibilities and not feel constrained, whereas the opportunity here expects new team members to hit the ground running on our existing plans. How does that land for you?” The candidates’ eyes widened as she considered the feedback, then she replied, “Wow, actually you're right, I really appreciate you saying that.”
The feeling of both sides being very honest with each other – it’s very meaningful. It makes me wonder what it would be like if this was the default in candidate interviews.1
So why *aren’t* most interviews like this? I have to admit, even after years of trying to perfect my craft as a recruiting leader, I still sometimes feel vulnerable getting this “real” with candidates. The fact is, humans are messy and I don’t always know how sharing my honest perceptions will be received by another. They might react badly – there are many possible causes why – and I would feel awful. Also, I’m not perfect and I may be off or biased in my perceptions, which could also cause a strong reaction.
This is why the work of establishing emotional resilience and boundaries are so important. Even if you are generally at the top of your game, it’s possible to have an off day. It’s also a numbers game – if you interview 100 people, no matter how good your screens are, I can guarantee a few might slip through that shouldn’t. So, should an uncomfortable situation rise, keep calm instead of getting more upset and escalating the situation, and return back to the above principles.
But for me, such moments are *very* rare – and a worthwhile price of conducting interviews from a present, connected, and collaborative place.
“Ok ok I’m inspired. How do I start interviewing like this?”
I have no hobbies besides thinking about recruiting,2 so it's taken a lot of brain hours to arrive at my current approach. I don’t expect anyone to be as… extreme in their commitment to recruiting– that’s what experts are for, so we can all learn from different specializations!
Plus, recruiting is an inherently *human* activity. So beyond the foundations, it’s important for leaders to develop their own styles. I hope it’s helpful to see a behind-the-curtain look at just one version.
Good interviewing is also not a standalone activity, but part of a much broader hiring system. I’ll be writing more in the coming weeks, but I also have plenty of past writing, courses, plus my team and I are available for consulting.
Through it all, I hope to make the above approach more common, as opposed to the current standard of interviews being soulless intimidation exercises. If you’re interested in making your hiring process more engaging, open, and human – all the while maintaining an incredibly high bar – please reach out so we can join forces.
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Jennifer Kim is the CEO/Founder of Workflow, an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and was an Advisor to dozens of top startups. She is also a Venture Partner at Symphonic Capital, and is known for her hot takes on tech industry and culture as @jenistyping.
Appendix / Past Discussions
Another perk of kind, live rejections – less work for you, because there’s no need to send more candidate emails afterward!
and being a diehard Swiftie