What He Learned from 1,000 Interviews

Our guest, Daniel Barber of Datagrail, shares what's he's learned about hiring as a CEO building high-growth teams. He also recaps his popular article "What I've Learned from Interviewing 1,000 People".



Grace and Ben give a warm welcome to Daniel Barber! Daniel has a wealth of tech leadership experience and is currently the CEO & Co-founder at DataGrail. A few years back, he wrote a piece for Salesforce entitled "What I’ve Learned from Interviewing 1,000 People." This article captivated us, and we wanted him on the show! Daniel did not disappoint, chatting about:

  • How the most successful people have deep passion for the mission—and how to discern if candidates have it
  • The importance of building diverse teams—and the dangers of pattern-matching against your own biases.
  • The value of being in person for interviews
  • How to build a "winning team" and look for value alignment, not "culture fit"
  • And of course, don't forget the speed round...are centipedes proof of aliens?!

Thanks for listening to Start with Who: The Interview Intelligence Podcast! This podcast is presented by —where we're on a mission to make hiring and interviewing more efficient and equitable. Come check out what we're building, or connect with Grace and Ben on LinkedIn! See you next time!


(transcribed by robots...sorry for the errors!)

Daniel: No one actually wants to be interviewed, and actually, if we're really being super honest, like the interviewer probably doesn't want to do it either, like they're just they're trying to fill a role like no one is, like, I want to do an interview. You want to do a conversation. You want to do what we're doing right now.

Hosts: Welcome to start with you, the interview intelligence podcast, I'm your host, Grace Tyson, and then the tagliani join us on our journey as we learn about talent acquisition, hiring and tackle the challenge of building an amazing team, one interview at a time. We've invited ceos, innovative people, leaders, talent acquisition experts and DIY movers and shakers as our guides. We'd like to have you join us. Welcome to start with who.

Ben: Welcome back to start with, who were excited to be joined today by Daniel barber. Daniel, Thanks for coming on the show.

Daniel: Great to be here. Appreciate the invitation.

Ben: of course, for those who don't know you. Could you tell us a little bit about you?

Daniel: Yeah so, Daniel, our CEO and co-founder of data privacy platform for the modern organization. I grew up in Australia, spent some time there, spent some time in the midwest, my father's side of the family from there, and then did my MBA in Japan to work for a Japanese company for a little while, moved to the Bay Area in 2011, which seems like an eternity ago, which I guess it is, and then was fortunate to work with a few different successful companies along the way. And now starting to outgrow and advise a couple of other companies as well. So an advisor and outreach Corps study and sign on site a construction technology company in Australia.

Grace: That is amazing. Your background is very impressive. And one of the reasons, Daniel, why we really wanted to have you on the show is because you wrote a very interesting article called what I've learned from interviewing 1,000 people. So we'd love to focus. We have a lot of questions for you as a follow up to what you wrote. The first question I have for you is why is passion such an X factor for you?

Daniel: Interviewing 1,000 people is quite a task. So I would just say, like, first off, it took a while. And what I learned through all of the trials and tribulations of hiring some amazing folks, making some misfires as well, because those are learnings in themselves. But the biggest learning was that passion or sort of drive for the problem that's being solved and drive to succeed. Addressing that problem was the overarching attribute that led to success for folks in the roles that I was hoping for. And a lot of that, I think, stems from attributes you can pick up through the interview process that will give you a picture into how passionate someone is about the role and about the mission of the business. But without that passion, you find that someone may just not be as motivated or not as driven to succeed. And ultimately, that leads to an employee who's just not as engaged in the organization for contact for listeners.

Grace: What are the types of roles that you've hired for and do you find that across the board that applies?

Daniel: Yeah so as a company builder now, I can't even think of the different roles that I have fired for, but a few different ones that come to mind, obviously account executive roles, sales development roles, operational roles. We recently brought on a VP of engineering on the back half of last year, a VP of Customer success applied a couple of those over my tenure folks in marketing of hired head to marketing. I've hired junior marketers. So at this point, pretty much every role it is consistent in that passion for the role. Passion for the mission does ultimately lead to a higher likelihood of success. The thing is, is passion by itself is not a quantitative measurement. Right? you can't measure someone's passion for a role. It's a latent variable. If folks remember back to their stats class. And so you need to derive someone's likelihood of passion through other attributes in the interview process.

Ben: so you mentioned in the article, which I thought was really interesting, was this power law. There's going to be at the high end of the curve some of your best performers that are going to contribute disproportionately. So say something like the top 10% are going to contribute at 3x the median, if you will. And I was thinking about that. And you mentioned, if you want to find those people, look at who those people are already inside your organization. So say, what are the trends of top 10% currently? I'm going to go find more of that. I think I have heard over and over again, that it's sometimes dangerous to go find the same traits that already exist inside your organization when you want to build a diverse organization. So how do you think about the give and take there of existing traits versus new traits in the pool of employees?

Daniel: So really good question. So using the existing traits of top performers to match and patent match against potential top performers outside of the organization and bringing them in, I think that's one method. I think the traits themselves. You can still look for regardless of what you see internally. Some of the examples that I put in the blog post, talk about someone's experiences traveling or someone's experiences with part time work through high school or part-time work through college, or perhaps it's the school that they went to significantly outperforming in the school that they went to, not just the school itself. Right so you can look at traits of individuals. And certainly the school that they went to might be a factor, but it's only one factor. And so I would encourage folks to look. Other attributes, I looked at people's interest in traveling and interest in exposing themselves to a diverse environment, because I do think the most diverse teams in the most inclusive teams build the right solutions, build the best solutions. That's just a fact. If you put more opinions, more perspectives in a pot, you just have a better pot, right? That's fundamentally, what this country was built on as well. And so I tend to think that if you can replicate that diverse and inclusive experience, you're more likely to derive a better solution, a better business and ultimately a better product for your customer.

Ben: So are there specific ways then now that you think about building a diverse team? I know you mentioned talking about diverse experiences, but do you go out of your way to fill the top of the funnel with diverse candidates or any secrets there?

Daniel: That's a really good follow up question. It's really hard, actually. So some of the roles that I hire for now, I have an extensive network of people that I could hire from like very deep network when it comes to sales. I probably have 500 account executives that I have met or interacted with along the way or hired. And so as a result, I could go to my network first, which would make sense, but then I would be pattern matching against potentially my own biases, which is dangerous. And so involving recruiters, involving other sources in the process is actually very valuable to do because it does create diversity in the candidate pool, which leads to, again, a better team, better product, better solution. But I do think that there are attributes which I describe in the post that help filter out all of the noise. So people that are active in high school and active in college, regardless of what college they went to, you can still be active. That's a choice. And so if you are, then you're exhibiting behavior that is perhaps above the rest. Like you don't have to get a part time job, but maybe you do because you come from an environment or you come from an upbringing where you need to get a part time job. And that shows a level of drive, which could be a variable that would elicit the behavior of someone who is passionate about what they're doing.

Grace: A little bit of a follow on question to that, Daniel, but you got me thinking, I mean, do you have any tips, tricks or particular questions that you like to ask in an interview to get to the heart of that. And uncover that passion really quickly and other attributes as well, that you look for?

Daniel: I actually try to have a very conversational approach to interviews. I think, like, no one actually wants to be interviewed. Right and actually, if we're really being super honest, like the interviewer probably doesn't want to do it either. Right like they're trying to they're trying to fill a role like no one is, like, I want to do an interview. You want to do a conversation. You want to do what we're doing right now. Right so I try to, like, keep it fairly conversational because the person is probably quite nervous on the other end as well. So let's be honest, no one really performs at their best when they're really nervous. And then I would say is I try to find a thing, whether it's an activity, whether it's an experience that they may have gone through in their life, not just work life that may elicit a conversation that is more animated. So I'll pick up on something on someone's profile. Maybe they did like a volunteer program in Southeast Asia, helping kids with their literacy program or something. Right and that's on someone's profile. I would like pick that as the item to spend 5 to 10 minutes and talk to them about that. And I want to see how excited they actually are about that thing, because if they get really excited about it, that shows me that they're passionate about the things that they apply their time to, which is actually all I'm trying to figure out. Right when you apply your eight hours, 10 hours in a day, do you actually give a shit. About what you're doing? That's very important.

Grace: Very underrated, seriously. And that's massive. I'm curious to you're talking a lot about the conversational elements of the interview and really going to what will give that person the energy as they're talking about it. And show the passion that you talk about in your article to about relationship building during hiring. So treating people like a human essentially is really important. Does that, in your experience, slow down the process at all? How do you balance efficiency versus truly developing a deep connection or relationship throughout the hiring process?

Daniel: Yeah, so it's really sad where we're here, right. We have to resume interviews now like it's not an option. But I do find it funny when someone tells me, oh, I did a phone screen. Man, that sounds horrible. What was that you. On a telephone call, oh, man, a phone screen that doesn't preclude the fact that that sounds horrible. I screamed to them, no, you want to make the person feel really comfortable, right? So, like, maybe that's getting on a Zoom at a minimum. But here's what we also calculated. When we are doing interviews at scale. But tallied up and responses, the person's actually going to work at your company like that's the goal. You actually want them to work there. You don't want to screen them. You actually want them to work at your company. So if that's the goal, then make them feel really comfortable and expose them to more stimuli which will likely lead to a better conversion in the process. So let's just back into what I'm describing there. If you could expose them to 30 minutes of time. And interview them through a phone screen, or you could have them catch the bus, come to your office or catch the bot or whatever service you're using, public transport, or maybe they drive and they come to your office and they go to your reception and they get to look all around the office. Right and see what the experience is like. And then they spend exactly 30 minutes in your office meeting with you. That's actually the exact same amount of time that you would have spent with them on that horrible phone screen idea. I just described earlier. So it's the same amount of time for the person who's, quote unquote, having the conversation or interview, if we have to call it that. So why would you not just have them do the conversation in person? Because then they get to actually see the office and interact with the person who's at the front desk and maybe another person on the team meets them indirectly because they walk them to the office or the room where you're doing the interview. So in the environment, appre covid, we would do in-person meetings for every single row and in-person meetings for every single first meeting. And the other reason why you do that is because ultimately, you want everyone to work at the company. Right? if the ideal case were there, but the ones that you don't want working at the company, you still want them to have an amazing experience. So when they finish that, you want them to leave an extremely positive experience on Glassdoor that says, man, that data. Great I wish I could have worked there, but I just didn't get past the first interview. But man, did I want to work there. And you want that on your Glassdoor because then everyone else wants to work there. And so you want every single person that comes into your building or gets on a Zoom with you to walk away saying, I wish I could work at that company. Some of them will get to a lot of them will not.

Ben: Yeah so what are you going to do about that moving forward? I mean, you mentioned you move to zoom, you talk a ton in the article about the importance of being a person, catching little body language and emotion, things. Will you go back to office visits? How are you?

Daniel: Well, yeah, Yeah. I mean, now we have a distributed team, so we're working within the bounds of what we have. So there will be zoom's and we can't help that. And that's what we'll do. But yeah, for folks interviewing in a location that has an office. So right now, that's just San Francisco. But that's changing this year, we will do in-person meetings for the first meeting because it's just the likelihood of conversion increases, which isn't that the whole purpose of the exercise? Right you want the person to work at your company. That's why you're talking to them. Sometimes I wonder. Yeah, like, why would you not do that? And that makes sense. So, OK, you're talking a lot about candidate experience. And basically what I'm hearing, which I completely agree with, is the importance of getting the candidate excited. You're not just, quote unquote screening them and trying to disqualify them out of your process. You're also trying to create an amazing candidate experience because people talk and there's Glassdoor and all these things you mentioned, you could spin this as a positive or a negative question. I always prefer the negative version, but so what do you think people really mess up when it comes to candidate experience? Like what are the horror stories of the list along like so long? The easiest one, though, and I see this. So often. And it pains me even to say it right, is people do a fine screen, it's a 30 minute interview, and they'll screen the person 10 minutes and cut the interview short to 10 minutes. That is insulting me. Like that person is going to leave your shit glass door of you. And I hope they do. Yep and if that, if that happens. And with that person who's interviewing is fired like, no, that's not our interviewing works. The person has spent a lot of their day probably preparing for that conversation. And if you're going to give them 10 minutes of your time, that's insulting. That's the most common thing that I see people do on the first interview. And I think the next one is that they don't think about necessarily the skills that you're trying to interview for. You can give people an assignment like our steps. Perhaps the easiest one to remember is like an account executive or an s.r.o. you give someone an assignment that reflects what their job would ask. Actually, b, because assignment based assessments actually are higher than emotional based assessments, which is what an interview is. So if someone has to do a live assignment, that's probably a better reflection of the job. So if you can try to set up assignments for a job, you should do that. But I see a lot of companies that don't do that. And so they'll have rather subjective based interviewing run by people who probably aren't trained to assess whether someone is a good fit. And then the last one, I would say the most common thing I also see is like, would I have a beer with them? What does that have to do with anything like syriza? What does that. Do you like? And we're going to put out a blog post on this topic. Like darro is not a family like Reid Hoffman is. Write a book about this. This is not a family. If you can't shoot and score or assist the person, that shooting or maybe your job is to clean the floor. Right I'm giving an analogy of a basketball game, but like this is a team. If you're not playing your part on the team, you're fired. And if you don't like the team, go look at another team. That's fine. Like, that's absolutely, totally fine. But like, the concept of like a family is odd. And it's tied to this concept of like, would I have a beer with them, which is ultimately tied to do. I want to be friends with them, right? No, we're on a business venture here. We're solving a mission of solving a particular problem, whatever that may be. It has nothing to do with friendship. Now, it might be like business friendship. That's cool. That's a bonus. I hope I find people that I want to be business friends with and maybe long term friends after we don't work together. But at the end of the day, it has nothing to do with do you want to have a beer with that person? That creates a significant amount of bias in the interview process and you end up hiring and not an inclusive team because you often want to have beers with people that are similar to you.

Grace: Thank you for saying all of that. I want to take what you just said and send it to a lot of hiring manager. So there are a lot of us are guilty of that. Well, with that in mind, Daniel, what do you think about the term culture fit as a term? Or maybe we want to frame it more as culture ad, you know, but how do you think about that in the interview process and not, oh, do I want to grab a beer with this person?

Daniel: Yeah, I mean, look, it's really hard. This is not easy stuff. I think you ultimately need to build your company values in a way they reflect the type of company that you are. You need to have values that are regularly described and illustrated with employee's behavior. And that behavior is the thing that you're looking to mimic, not the attributes of the person. That's not what you're trying to do. You're trying to elicit similar behaviors that you want that drives success for your customer. So starting with the values first is the way to do that. And I think tying how you will assess those values throughout your interview process is likely what will reinforce the culture that you're looking to build now? Again, I'll just state the obvious. A more diverse and inclusive environment will be a winning team again. Obviously, that is like just keep reinforcing that. So trying to assess for those, at least for grow, that's first and foremost, what we think about how do we build a winning team, which a winning team is a diverse and inclusive team. But you have to start with your company values. And then intertwine those through the interview process to assess for behaviors that you're looking to find perfect.

Ben: Last question. As Greece and I try to build a company here, you've done this a few times. Is there any big pitfalls you would advise to executives who are building a skill up or a startup company that you really need to be hyper aware of?

Daniel: I'll give one of my own failures just because those are more fun to share. It's so easy to go to domain experience and people like over index on that all the time in that you think, oh, the person has experience in security or the person has experience in. How are they going to be a great fit? Not at all. It's an attribute. So you should think about it. But I would put it in the same bucket as the other attributes. And I've personally made mistakes both as a company builder and as an operator in scenarios where I've over indexed on. Oh wow. They have marketing experience that's going to help. Not necessarily all. They have Sas experience that's going to help. Right not necessarily. If they're passionate to solve the problem or you've got to look for is if they like doing what they're doing, even if they're not good at it, they're going to get good at it because they like doing what they're doing. That has not. Thing to do with domain experience, so I have made that mistake and said, oh, this person has 10 years of privacy experience, they're going to be awesome. No yeah, they what?

Grace: That's really good advice, Daniel. I've also I've seen that play out poorly experience as well. Yet Thank you so much. That was amazing. We love to do one last little thing with you. Like to do a speed round with some fun, non-work related questions. So listeners can get to know you. So first, rapid fire question. Whatever comes to mind first for you. What brings you joy outside of work? Try to love it. Say, what's one thing you do during COVID or quarantine that you didn't do before?

Daniel: Working out at home, what do you do to work out at home out of curiosity? My fiance and I have a workout schedule with different routines that I never would have thought I would do at home. It's amazing. Good for you. It's hard to stay motivated at home, I found. Yes there's no gym. So there's no personal trainer, like literally telling me what I'm supposed to do. So that's hard.

Ben: Yes agreed. Do you have a go to takeout spot in COVID or delivery?

Daniel: Pacino's in Potrero hill. It's a good Italian restaurant and I'm very particular about Italian food, and it's actually good.

Grace: That's great. Sounds really good. One thing you think everyone should either watch or read this year?

Daniel: Ben Horowitz book what you do is who you are from 2019.

Grace: I will add that to the list. All right. And we ask everyone this. Do you believe aliens exist? Why or why not?

Daniel: 100 percent, I do know why. So many planets, too many solar systems, too many galaxies, signs.

Grace: I'm with you Daniel.

Ben: I'm not convinced yet. We're working on that.

Grace:  And we're working on that. I didn't ask him this in the interview process.

Daniel: And I should have I encourage you to find a magnifying glass and look at a centipede and then tell me that that's not the case.

Grace: That's a brilliant. That's brilliant. Yes I'm like, thank you for that. A thank you.

Daniel: Why is there hundreds of legs of the centipede?

Grace: Thank you, Daniel.

Daniel: Yeah go do that, then.

Ben: I'm on it. Centipede hunting, I'm, taking the afternoon off. Here I go.

Grace: Yes, thank you. Please do you prioritize this over all your other work. Daniel, thank you so much for joining us. We appreciate it.

Daniel: Yeah, this is fun.

Hosts: Thanks for joining us for another episode of start with who, the interview intelligence podcast presented by Pillar. Find out more about Pillar and how to do the best interviewing of your life and build an amazing team, all starting at pillar.hr. And if you like this episode, leave us a review or shoot us a note. We'd love to hear from you. Thanks for listening. We'll see you next time.