Startup Hiring with Jennifer Kim

How do you win candidates when bigger companies can offer more money? What changes can you make to your interviews to get your candidates excited about your company? In Episode 23, Jennifer Kim (@jenistyping on Twitter) shares her expertise around hiring, and we dive into what’s different about startup hiring.

Show references:


JENNIFER TU: Welcome to Storytime with Managers, a podcast by Cohere.

Hi, I’m Jennifer Tu, and I’m here with Jennifer Kim to talk about startup hiring. Jen, can you tell us a little about yourself?

JENNIFER (JEN) KIM: Sure. I’m a startup advisor. I work with startups on all things related to people, whether that’s hiring, diversity and inclusion, people operations. I also work as an exec coach to founders. So, my goal really here is to bring emotional intelligence to startups so that we can build better workplaces and see startups can be even more successful.

JENNIFER TU: Awesome. So today, we’re going to talk a little bit about hiring for startups. And my very first question is, how is hiring for a startup different than hiring for an established organization? And what should I be thinking about differently if I find myself in this kind of situation?

JENNIFER (JEN) KIM: One specific way startups can be a lot better at hiring is really thinking about it as a much holistic process than just asking better interview questions. Often when I talk to founders, engineering managers at startups, “Hey, what are you doing to improve your recruiting process?” I’ll usually get an answer around, like, “Oh, we’re trying to evaluate this question better. We’re trying different tools.” And that’s certainly a part of it, but what startups forget is that you are not recruiting like, let’s say, the employer brand of a Google or a Facebook. So not only are you asking better questions, you also have to learn how to attract people. When you’re a small team, you have to get really scrappy and creative to get candidates interested in you because the chances are they haven’t heard of you.

One more thing. Recruiting is a lot about building rigor and a lot of detail oriented process, being really good at managing their experience. All of this takes a lot of time and care. And it can feel pretty difficult to manage all of that when you’re also trying to survive and run 100 miles an hour as a startup. So we can go into a little bit more tactics in a minute, but it’s an area with a lot of opportunity, for sure.

JENNIFER TU: Yeah. I think this is really interesting of when you are hiring for startups, you need to be looking at the entire package beyond just the interview itself. And just to help me and our listeners kind of get into the right frame of mind, what kind of startups needs to be thinking about this? Like, at what point are you big enough or mature enough that you can switch to a more corporate mindset and at what point do you need to really keep this whole picture, all the details mentality?

JENNIFER (JEN) KIM: I see hiring as just as any other business function that you have to do. Let’s say when you are super small startup, the way you do sales when you’re getting your first 10 customers is going to be really different when you’re doing, let’s say, your 100th customer, your 1000th customer and so on. And the same principles really apply for recruiting people to get the best people to join your team. So I will say maybe at the very, very earliest stages, maybe your employee number two or three, most teams will hire from the networks they already have because they want to work with people they already know and trust. But after a certain stage, and it really varies depending on the startup, you can no longer just hire from your existing networks. You want to really branch out, bring in different skill sets, maybe fill roles that you don’t have existing acquaintances or professional connections in. And that’s when you realize you can’t just hire based on ‘my friend’ or ‘my neighbor’s cousin’. It really becomes about building a process that can win you the best talent.

JENNIFER TU: Okay. So that means when I’m thinking about startup hiring, I need to apply your mentality to this whenever I need to hire someone who I can’t hire out of my own network. And I don’t need to worry about it quite as much when I can hire anyone to fill anything. And so it’s that in-between stage, I really need to focus on adopting this new startup hiring mentality around.

JENNIFER (JEN) KIM: Yeah. And it’s interesting because even if you work for a much bigger company, a lot of these principles are still relevant. I find that engineering managers at thousand plus companies, a lot of these folks, the ones who really care about building the best team possible, the ones who are really rolling up their sleeves and taking a lot of personal responsibility, they’re doing in a very scrappy way that doesn’t just rely on the existing HR kind of processes or their recruiter delivering their candidates for them. They’re the ones who have to actually go out there, talk to people, constantly expand their network, learn how to really kind of position their opportunities better in a way that doesn’t just rely on your larger corporate employer brand. So if you are a leader of any kind that wants to build the best team possible, you’re going to have to get scrappy.

JENNIFER TU: Okay, got it. So what does it mean to get scrappy? Let’s say I’m realizing I need to hire my next five people onto my team and or maybe my next 10, and there’s no one in my network or in anyone’s network who fills these 10 slots. What do I need to be thinking about?

JENNIFER (JEN) KIM: It really depends on kind of the size and stage, of course. But one thing I really emphasize is thinking about motivation fit when it comes to hiring the best team possible. So let me give an example. Let’s say you’re hiring an engineer, frontend. If you were to compete with the Googles or the Facebook of the world and you’re a small startup, I can guarantee you, you’re not going to be able to compete on salaries or the benefits. When you are going up against companies that are literally printing money in some ways, you’re going to have to go for some different angles to make your opportunities way more competitive. But then by doing this, you’ll also find people who are more motivationally aligned. The person that’s really, really excited to join a five-person team or a hundred-person team is actually a little bit different profile than someone who wants to join a Google or Facebook. But if we’re not thinking about hiring processes in this way, what I feel a startup’s doing is they’re trying to copy existing processes of larger companies. This cargo cult, just place it in. And you’re surprised when hiring feels like it’s taking a lot of time and effort spent, but you’re not getting the results that you want. So at the very beginning, I really encouraged things to think about who are you really looking for? What does the profile of a successful candidate look like in this context for your team that’s different than other companies?

JENNIFER TU: How do you do that? Sometimes you think you know what you’re looking for. And then when you actually try to sit down with it, you realize you can’t really describe it. So if you find yourself in that kind of a situation, what do you do?

JENNIFER (JEN) KIM: Something similar happens at companies as well. We would, of course, love to hire the both brilliant, technically skilled, emotionally intelligent, communicative, great team worker, team player. But that’s not sometimes what’s available. And when you are a small team and you are competing against other companies, you might not realize that that person you have in mind, they have so many options. So to hire the best team possible, you’re going to have to get competitive based on your strengths. So at a small startup, the things you have to offer, the opportunity is very different. The resources, the perks of a larger company, don’t even try to compete on those. You’re going to lose. Instead, the things that you can highlight and look for people around are things like, here’s a place to come in early and have an impact. Here is how we’re thinking about culture, we’re really being thoughtful. We’re such a small knit team. We are looking for these kind of people to really build something meaningful with us. This is the mission of our startup. And here’s what we want to do together. Are you that person? Is this something that you are interested in? [Inaudible] is yes. Picking well and asking the good questions, but it’s also just as much about bringing the right people to you. It’s really kind of the attracting people to your opportunities so that you have a lot of different options to work with. You really are working with the best pool of candidates possible as opposed to who is just submitting a resume right now.

JENNIFER TU: I feel like I’ve seen this sometimes where you’ll go through this whole interview process, and at the end, you’ve got the hiring manager, usually the CTO, who’s like selling you on his vision. And you walk out and you’re like, “Oh, my God. This company is going to go so many places and my career will just rocket off with it.” And at the same time, you’re also like, “But they really grilled me on how to do that binary tree,” whatever nonsense. And I’m wondering, how much can you rely on that final sell of the CTO and how much you need to integrate this across the rest of your interviewing process?

JENNIFER (JEN) KIM: Good question. Also, I did notice you just said CTO and refer to him as a him. I don’t know if you want to…

JENNIFER TU: Oh, I did not catch that at all!


JENNIFER TU: That’s terrible!

JENNIFER (JEN) KIM: I don’t mind.

JENNIFER TU: Yes, that’s a good point. I should have used ‘they’.

JENNIFER (JEN) KIM: Just wanted to point out, yeah.

JENNIFER TU: But it’s true. I’ve never had that closing pitch with someone who’s not a him. And I’ve never had it with someone who’s not a white him.

JENNIFER (JEN) KIM: I mean, that’s just the nature of kind of what kind of profiles exist for most startup CTOs, right? And I should do think that that’s changing. But it is something interesting to note.

JENNIFER TU: Yeah. Thanks for pointing that out.


JENNIFER TU: All right. So you’ve got the CTO and they give you this amazing pitch. How much does it matter that the rest of the team was or wasn’t part of that pitch?

JENNIFER (JEN) KIM: At the end of the day, it does come to kind of your gut and just making a decision that feels right for you. Joining a startup is really fascinating to me because it’s inherently a little bit risky. It’s a little bit like playing lottery with your career in that you are taking on some risk, but you’re hoping for a greater upside. You’re also choosing a very different type and lifestyle of work, which is maybe as opposed to something more predictable, steady growth, maybe a more predictable kind of schedule of getting promoted in the project that you’ll work on. The nature of startups is that sometimes it can feel like every three months, things are changing so fast. You’re working for a brand new company.

So, it just really depends on the person. But I would say something to really keep in mind and ask a lot of questions around is the vision, the upside, the dreams of an IPO can be very exciting. That’s what makes this world really, really fun. At the same time, if you are miserable in your day-to-day, that may not be worth it as well. So, this is really the chance to ask a lot of questions about culture, team, processes, the leaders, their styles or their experiences. Are they open to feedback? What kind of lessons have they learned so far in their journey as leaders or maybe when they were employees themselves in other places? And where are their motivations coming from?

JENNIFER TU: That makes me wonder if part of preparing as interviewers is making sure that all of your team needs to know about how to encourage those kind of questions and be able to be a part of that. Is that important? Or again, is it okay to just concentrate it towards one single section and make each section dedicated to doing a different thing?

JENNIFER (JEN) KIM: Once again, I think we should think about how the profile of your top desired candidates, they’re going to have a lot of options. They are going to be picky because you would want to be picky if you were doing a job search. I think something that’s interesting with startups is that, look, I get it, I’ve been part of early stage startups, it’s super fun. And sometimes you can kind of buy into your own hype with a new, exciting press development or investors saying really nice things about you and chasing you down to giving you their money. But at the same time, you want to be grounded because the day-to-day experience for the people that you’re building, you want to make sure that people are going to be treated fairly, that people can actually do their best work. And a lot of this comes down to the day-to-day of good management. It’s not just about the dreams, the dazzle, even though, don’t get me wrong, it can be really, really fun.

JENNIFER TU: Let’s say that I am a hiring manager and I’m in that situation that you’ve been describing where we’re not getting that many candidates. And for whatever reason, we keep losing them. They keep going to other startups. They keep going to Google, like it’s just all over the place. So there’s no consistency there. What do I need to be thinking about as I look at changes I can make to my hiring process, so that way, we are able to make the hires that we need?

JENNIFER (JEN) KIM: I think really approaching the hiring process as a relationship between the company and the candidate can be really helpful. Every person that enters your process is almost like a customer and they have different pieces of feedback. They have highlights, they have lowlights. And what you want to do ideally, is try to get a sense of that. One way to get that feedback is to literally ask. This is where maybe at the end of the process, [inaudible] process, you can request a feedback form. Really kind of emphasizing, “Thank you for going for this process with us. We’re really invested in this. And we’d love to hear your feedback so we can improve things in the future. Are there any comments that you want to share with us? Things that went well that you would like us to do more of. Things that maybe didn’t go so well that maybe you didn’t have a chance to bring up. But if you want to share them anonymously, we would really, really appreciate it.” And I think this is where a lot of teams will get really, really surprised.

I’ve heard comments like, in these feedback forms, candidate sharing, like, “Actually, there was this one interviewer who I just didn’t get a good sense from.” Let’s say, “He was condescending and I didn’t think I was set up well for that interview.” And this is something that you might have had no idea about because this engineer is a really, really fantastic, productive engineer, but someone who just hasn’t gone really trained on interviewing. And the importance of really showing up as warm, inviting, and encouraging people to do their best. So a little bit of intervention with interview or training can make a big difference and you might not even realize it if the person hadn’t told you about their experience.

JENNIFER TU: That’s really helpful. What kind of interviewer training are you thinking about when you think about interventions like that?

JENNIFER (JEN) KIM: This is an area that I’ve thought a lot about, have built interviewer trainings around at my previous company and I teach startups on it now. But becoming a great interviewer, just like any other skill, it takes time and we’re kind of learning at different levels from different starting points. So I’ll usually kind of break it out to different levels.

And the first thing I always address to people is that your job as a beginner interviewer, is to just relax. I’ll kind of explain why that is, because I find very common issue with inexperienced interviewers, kind of not really prepared, not really given some guidelines and just thrown to the wolves. “Here, go interview this person and tell me if I should hire them.” What often insecure interviewers will do is get nervous and then pass off their kind of insecurity to the candidate. So this is where they’ll ask questions like, “How would you solve this problem?” Or, “Do you know how to use this tool?” And the candidate feels like, “I can learn.” Or like, “Oh, I don’t have enough information to answer that question because that’s context that you have that I don’t.” So a lot of insecure interviewers, I find, are asking questions that test what the interviewer already knows as opposed to having a conversation.

Step one of interviewer training is I always tell interviewers you need to recognize your power in this process. Even if you’re nervous, the person that’s sitting on the other side of you is even more nervous. So, your job is to not even judge the person and figure out whether you should hire them, but really create the environment where a candidate can show up to do their best performance. It’s all about making small talk and kind of being calm and maintaining your own energy, because if you’re jittery, the candidate will pick up on that and will become jittery as well.

And then I move on to things like how to ask better questions, how to listen, like, really, really listen. Not just do the thing where you’re listening, what you’re actually thinking about, what to say next, how to ask, follow the questions, how to communicate honestly with candidates, how to address kind of curve balls when you get asked a tough question. And then finally, when you kind of mastered all of those, you can start to get comfortable with should we hire this person or not? But often, that gets really skipped. So, interviewer’s signals tend to be not as strong as we would like, without interviewer training having taken place.

JENNIFER TU: That sounds like a really fantastic framework for how to be approaching interviewer trainings with your team. As we wrap up our time together, do you have any final words of advice for our listeners?

JENNIFER (JEN) KIM: I do, yeah. I’m an unabashed recruiting nerd, even though that’s probably not one of the cool nerds. But I’m genuinely so excited about this topic because I think it’s really fun. I actually think the fact that recruiting is so hard is what makes it so interesting and fun to work on. I think where I see a lot of folks from technical backgrounds approach hiring from that is we want to get to certainty. We want to figure out who is the most technically skilled so we can hire them. And that’s definitely a part of it, evaluating skill sets. But at the same time, we’re trying to make decisions about other humans based on a couple hours of conversation. And getting to certainty is really, really hard. And if you think about maybe your own experience or your teams, you’ll find that often the best hires come from unexpected places, from untraditional backgrounds, from moments that you really couldn’t have predicted.

So, I would encourage everyone to think about hiring in a way that’s constantly iterative, really balancing kind of the technical mindset, but also as a way of continuing to stretch and practice your emotional intelligence skills. At the end of the day, hiring is also about using our people skills so we can do our best work possible, which is always going to entail both our technical skills and people skills.

JENNIFER TU: All right. Thanks so much, Jen. If people want to continue the conversation, what’s the best way for them to reach out to you?

JENNIFER (JEN) KIM: I’m a prolific tweeter and writer on all these topics. So, I’m on Twitter @jenistyping. I also teach Startup Recruiting Bootcamp, which is a workshop. We’re fully remote now where we go way more in-depth on all of these topics. And I provide a lot more frameworks and tools, a lot of conversation to community of people that really care about hiring and want to do better. So, I hope your listeners can come join.

JENNIFER TU: Yeah. What was the website for that one again or how to look at more information about it?

JENNIFER (JEN) KIM: That one’s

JENNIFER TU: Awesome. Thanks so much.

JENNIFER (JEN) KIM: Thanks, Jennifer.

JENNIFER TU: Thanks for listening to Storytime with Managers by Cohere. I’m Jennifer Tu. Our theme music is by Kevin MacLeod and we are edited by Mandy Moore and the Dev Rep’s crew.

If you like this episode, please think about leaving us a review on your favorite podcast listening platform. This can make a really big difference in helping other people find and start listening to Storytime with Managers. Thanks so much.

Startup Hiring with Jennifer Kim
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