Masterclass with Peak XV’s Jaime Bott: 10x Your Hiring Process in the US

SHOW NOTES

• Good candidate experience: a competitive edge [0:28] 
• Hallmarks of a great hiring process [04:30] 
• The essentials of a good interview process [09:28] 
• The small details that make a big difference [14:27] 
• Common hiring pitfalls and how to avoid them [18:14] 
• Optimize the role of direct reports on the interview panel [25:58]
• Communication: The key to enhancing candidate experience [27:25]
• Audience Q&A excerpts [28:38]

TRANSCRIPT

Jaime: Quick intro, [I am] Jamie Bott. I spent almost 13 years actually working for Sequoia Capital on the US, Europe-side of the business, leading a large global talent team that was supporting our founders with everything from early-stage engineering hiring, all the way through to hiring their VP and C-level executives. My personal spike though, is executive hiring. 

Good candidate experience: a competitive edge [0:28] 

And I’d say at this point, I’ve probably worked with hundreds of founders across thousands of executive searches. So it’s a really large data set to work off of as I talked to you about [how to] 10x your hiring process. In the last six months, I’ve been working exclusively with Peak XV founders who tend to be pretty much international, so not from the US. And during that time, I’ve observed a few mishaps here and there around candidate experience. So I want to talk to you about how we can make a positive impression on candidates that we want to hire in the US.

Before we get into why candidate experience is important and how to do it really well, I just want to quickly define it, because I’m not sure if this is a term that’s used outside of the US, but it’s basically a series of experiences that a candidate will have with your company along your entire recruiting process. And it’s how those experiences make them feel. You want them to walk away feeling good. And basically, it’s the golden rule, which, I don’t know if that’s also universal, but it’s to treat other people how you want to be treated yourself. So very common sense. 

Why does it matter? So there’s a couple of things. Number one is your conversion rate. So, if you provide a great experience when you’re trying to recruit someone, you have a much higher likelihood of being able to convert them to an employee if you decide you want to make an offer. On the flip side, if you run a really bad process, there is a much higher chance that someone’s going to fall out of your process or they’re going to decline your offer when you get to the point of wanting to actually make them an offer. And that is heartbreaking when that happens. 

So when I first got into venture, it was in 2010. And at that point, everyone was talking about a talent war, “Oh! It’s a talent war. It’s really hard to get talent!” And it really was. It was brutal. You would send out a hundred messages and hope that you would get a single-digit percentage replies. And even of those, not all of them were, “Yes, I’ll chat with you.” And that really continued up until about two years ago. And so, if you could actually get a candidate into your process, it was extremely important to make sure that you ran a really strong and positive process, and that people weren’t falling out because you were screwing things up. 

Now the reason why I bring this up is that you all, if you come into the US and you’re hiring here, [and] you don’t have a brand like some of these companies have, and then on top of that, you’re going against companies that were born and raised in this era where talent is scarce. And so they know that they have to run a tight process. They are running a tight process. And so you really have to up your game as far as how you treat candidates and how you evaluate them and run them through your recruiting process. 

The other point I’ll make about the reason why you want to have a great process is that you want every candidate to walk away feeling really good about you and your company and your brand, regardless of whether or not they got an offer. And the reason why is that much like how customers talk to a few people about a positive experience and a lot of people about a negative experience, it’s the same with candidates. So they’re out there, they’re talking to their friends. They’re even posting it on Glassdoor. Now, I don’t know if you’re all familiar with Glassdoor but you do not want negative things said about you on Glassdoor because you cannot unwind it. You cannot take it away and candidates will look at that and make judgments about your culture and your business, based on what they read there. And, it tends to be very negative. So you want to avoid that at all costs. 

And then the last point I’ll make, again on why it matters is, in general, it takes a lot of time, energy, and money to hire people. And if you’ve got a bad process that’s leaking out candidates left and right, you have to add more candidates into it, and then it’s just taking you more time, money, and energy. So let’s just be efficient and have a great process. We don’t have to go through a lot more candidates. 

Hallmarks of a great hiring process [04:30]

So what does a great process look like? I’m going to talk about this in three parts. One is the basics. The second part is about the interview. And the third part is around offers. If you can just at least get these basics right, you’ll be doing much, much better than many other startups that you’re competing with, the international startups. Again, I think it’s a high bar when you’re competing with US-based startups that have been born and raised here, with talent scarcity. 

So first and foremost, as you think about the series of interactions that candidates will have with your company, it very often starts with the website. So you want to make sure that your website feels inclusive. And what I mean by that is if you’re using stock photos for employees, when a candidate goes there, they’re not seeing all one ethnicity, all one gender, all one age group. You want anyone to feel like, “Oh, there’s diversity here. I might fit.” So that’s first and foremost. 

And then secondly, you want to make sure that your messaging is on point and that you have a good employer and employee value proposition. Why would someone want to work at your company? And that’s where you’re really talking about your culture and it goes beyond and deeper than, “Hey, we have ping pong tables here,” right? There’s gotta be more of a mission there. 

Be responsive, please. This is the thing that I see the biggest disconnect between international founders and US-based candidates. I think one of the challenges is that international founders are very accustomed to getting work done on WhatsApp, and US-based candidates are very accustomed to using email. And I can’t tell you the amount of times I’ve done an introduction to a candidate and they followed up with me later and said, “Thanks for the intro, but I wasn’t actually able to connect with the CEO or, “I had a great meeting. There were supposed to be some follow-up steps and then nothing ever happened. I didn’t hear back!” So please respond. And if you’re thinking, “Yeah, but I didn’t really care about the candidate. I don’t really want to move them forward in my process.” So, it goes back to, “We want to treat everybody well,” so that they are saying good things about the company, even if they didn’t get an offer from us. 

Move quickly and communicate all the steps in your process. So as a small startup, you have an advantage here against bigger companies. You have fewer decision makers and your process will be more simple as a result. And so you should be able to move people quickly through and also let them know what to expect. 

This last one. Again, treat people how you want to be treated. So you want to give people proper rejections, close the loop with them and give them feedback on why you’re not moving forward. And so the way I like to frame these, it’s easiest when you actually have a finalist that you really want to move forward with. That’s a much easier conversation. And so the way I’ll typically structure those is, “Hey, really enjoyed meeting you. Here’s what went well. Really sorry. We’re actually moving forward with someone else. There’s no deficiency in your background. We thought you were great, but this person had a slight edge.” 

And the edge can be anything you want, but it has to be something that’s missing from this other person’s background. So an example might be if it’s, let’s say, it’s a sales leader, “Hey, the person that has the slight edge over you has the exact customer Rolodex that we’re trying to break into. Or this person recently spent time in a company in our sector and just deeply understands the space on Day One.” 

It’s a harder conversation if you don’t have a finalist and you’re just like, “This isn’t the one.” And you have to reject them. In that case, don’t say things like, “You’re not a culture fit. We really don’t like you.” In that case, you do need to find something that is a specific gap in their background. And it can’t be obviously on their resume because that will p*ss people off, “Why did you put me through your process? You knew I had this gap. You just completely wasted my time.” But it has to be a gap that you picked up along the way in the interview process and hopefully, something that the person can’t argue with. 

And I will just warn you ahead of time if it’s a sales executive, they might just tell you why that gap isn’t actually a gap, and it’s a much smaller gap than what you’re thinking. So that can be a little bit awkward, but you just need to stick to your guns and just keep moving forward. And it should be done over a call with executive candidates. If they give you multiple hours of their time, please pick up a phone, and give them a ring. For candidates who are not at the executive level, I think it’s okay to pass on an email with positive and constructive feedback, but always offer up a call. And not everyone will take you up on it, but it is the right thing to do. In the US people expect a phone call to decline. 

The essentials of a good interview process [09:28]

Now we’re going to go into the more advanced stuff, around the interview. So what does a great interview process actually look like? First and foremost, you need to define it up front. Know who’s on your interview panel. Make sure that everybody is assessing a different competency and that they have a different question set that they’re working off of. What’s not good is if you have five interviewers go in and they all say, “Tell me about your background.” You’re not going to get good data about that person, and everyone’s going to walk out and not really know if this person can 100% do the job.

Also, do not ask riddles or bizarre questions like, “If you were an animal, what would you be?” That’s not something that US candidates really enjoy or respect. And they’re (the questions) not predictive of job, or future job performance either. In general, be respectful. So that’s showing up on time. Don’t reschedule meetings. Don’t do a no-show for meetings, all the common sense. Treat other people how you want to be treated. Prepare in advance. These candidates put a lot of effort into coming and interviewing with you. So they’re doing a ton of research and it’s really obvious if you come flying in five minutes late if you haven’t read the resume or looked at the background. So just at least do a little bit of prep work and respect for the candidate. 

Make sure you’re allowing time for questions. So every single interaction with candidates, there needs to be time for questions. And, actually, this can be a really great rapport-building tool if you allow candidates to ask their questions at the beginning of the interview and then you interview them after you’ve answered all of their questions. 

Then, lastly, I would just say feel free to add thoughtful touches along the way. One example is something that I don’t know if you all got to see Doug (Douglas) Leone yesterday – Doug is one of my favorite people on the planet. Doug is a huge fan of this, where he asks all of his founders, for exec-level roles, put together what he calls an opportunity deck. And it’s almost like a pitch deck for money, but you’re like, you’re pitching the candidate on your opportunity. Like, why would they want to join your company? Why would they want to take this role? So it’s all the selling points, and you can give it to them in advance of actually meeting them and it shows a real care for the candidate. Other things like, “Okay, you’re gonna come in and have a full day of interviews. I’ll send you a Starbucks gift card the night before. So you can go get a coffee right before you come in to help boost up your energy.” It’s little thoughtful touches and the sky’s the limit on this. So offers, this is a really important part of the process, but it’s not going to go well if you didn’t do all of the stuff you needed to do before to make candidates feel wanted and loved and excited about the opportunity. 

So hopefully by this time, you’ve been collecting data about the candidate all along the way, like what are their motivations? What gets them excited? Is it learning? Is it an advancement? Is it managing other people? Because when you make your offer, you want to make sure that you’re speaking in their love language, right? What’s going to get them excited? So you want to focus on the things that you know, the things about your role that you know will get them particularly excited when you’re making that offer to them. 

Secondly, before you even get to a point where you’re talking about numbers, I think it’s good to ask the candidate, “What are your outstanding concerns about this opportunity?” So let’s just assume the numbers are going to work. “I want to hear everything that you have hesitations about.” 

Another great question I like to ask is, “What does your spouse or your partner think about this opportunity for you?” That is super illuminating because for some reason they feel more comfortable relaying the objections of their partner than themselves. And that is where you really can get to the heart of, “Okay, those are the real objections. Let’s go through those.” 

And so, once you’ve addressed all of their concerns, hopefully, and you get to a point where you’re ready to give them numbers, it’s really important that the CEO or the founder or whoever the hiring manager is, not an external recruiter, not the HR person, not the internal recruiter, but the actual person that’s going to manage this new hire, is the one to deliver the offer. And ideally doing it in a really thoughtful and delightful way. So what you don’t want to do, I heard this example, it came up the other day was, a CEO took a candidate out to dinner, which is great bonus points taking the candidate out to dinner, but slid the written offer letter across the table and said, “I’m supposed to give this to you in person,” that doesn’t really convey enthusiasm, excitement. “Do I want to jump into that company?”, I don’t think so. So, don’t be that person. 

The small details that make a big difference [14:27]

One thing I’ve seen used to great effect is an offer deck. So having a base template that you can tweak and customize for the person that you’re delivering the offer to, where you talk about your excitement about their fit with the opportunity, the role, the responsibilities, the first 90 days. I like to put an org chart in there with their face and their name as if they’ve already said yes. And then the compensation and the benefits. And it just shows a level of care that most companies are not doing. Very often in delivering offers, people just jump on the phone and say, “Here are the numbers.” And there’s gotta be some preamble and some buildup to it, some excitement, some reminders of why this opportunity is so good for them. 

I think the other area I see that’s a bit of a challenge with international founders coming over here is US talent is really expensive and unfortunately, it just is what it is and you’re not going to get someone below market. You have to just pay [as per the] market. I do think that sharing the comp (compensation) data that you’re leveraging to come to your decision of where you want it, and where you want to pay this person if you can share it with them as well, it goes a long way towards building trust and having the candidate feel like, “Wow, this is a really transparent culture.” Like, “I could see myself here!” 

The other thing that I’ve seen companies do is give candidates an Excel worksheet with, “Here’s what the value of your equity is today and here’s what it could look like in different likely scenarios.” But, we don’t want to be like, “Hey, here’s what it’s going to look like…a $100 million…” Well hopefully [yes] but you know…

So you have the verbal acceptance. It’s time to give them their offer letter. Have you set up a benefits program? Do you have the ability to give equity? Do you have bank accounts? Do you have an offer letter template that you’ve had approved by an attorney? These are all really important things. So you want to make sure you do all that pre-work and lay all that groundwork so that there’s not a big lag between that verbal acceptance and when you can get that offer letter out. Because if you lose momentum, it makes candidates nervous. And that means that they’re still available for someone to come swipe them out from underneath you. So make sure you have all that ready to go. 

Involving the spouse is another thing where you can really get bonus points. And this can be everything from offering to answering the spouse’s questions directly. It could be taking the spouse and your candidate out to dinner. And it could also be just, giving a gift card to the couple, so that they can go out to dinner and talk about the offer and whether or not this is a good fit. So a little thoughtful touches. 

And then in general my favorite is love bombing. So they have the offer, they’re mulling it over and you want them to feel the love. And so this could be as simple as having the entire interview panel, send a text, send an email, or send a Loom video about how excited they are about the offer and that they hope the person will accept. It could be sending a personalized gift. So for example, I love tequila. If someone sent me a really nice bottle of tequila. I’d be like, “Sure, I’m in. Let’s go.” So it can vary. I’ve heard extreme examples of people getting bicycles, or one person getting a cow! I’m not suggesting we go that extreme, but I think there’s a lot that people could do with this. 

Common hiring pitfalls and how to avoid them [18:14] 

So now we’ve talked about all the things that we should be doing well. I just [also] want to talk about some of the common pitfalls. So starting with grilling. So this very often happens in the very first meeting where a candidate shows up and the CEO or founder thinks, “Great! They’re a candidate. I’m going to grill them and ask them tons of questions.” They’re not a candidate yet, at least in the US. In the US, that’s like a discovery meeting where they’re like, “Do I want to opt into your process?” And for CEOs, it should be like, “Do I want you to opt into my process?” So it’s a very high-level meeting with coffee where you’re doing more selling than buying. You’re telling them, “Hey, here’s a little bit about the story, the company.” Hearing a little bit about their background and the goal is to get them to the next meeting where you actually can start to assess. Don’t judge candidates for showing up maybe not having done a ton of research for this first meeting, because they don’t know yet if they want to put in the effort. So this is your chance to pitch them and see, and get them going. 

Speed or pace. So we talked about, “Hey, it’s an advantage to move quickly,” but you also need to pace yourself, because it’s not a good experience if you run someone through your process so fast, and then you’re like, “Okay! Sit there. Wait a second. We got to go meet other people and see if you’re the one.” So that’s not good either. So you really need to pace it out. Not too fast, not too slow. 

Indifference. I had one candidate come back to me and tell me that a CEO was very stoic in the conversation, and that it wasn’t really inspirational or really exciting. Make sure you show up. Not just in your offer, but in every touch point with your passion. Like you’re all passionate people. You started a company for a reason. And so let that come out and share that with candidates. 

Being inconsiderate. So we talked about hey, show up on time and don’t miss meetings, things like that. I would add on this one to be mindful of time zones. So don’t offer up time slots that are like 3 a.m., 4 a.m. in the candidate’s time zone because that’s not being very thoughtful. And it makes them nervous too, “Oh man! Is this person going to think… Do I have to work at 3 a.m. or 4 a.m. in the morning?” So it doesn’t put a good foot forward. 

Asking inappropriate questions. There’s a lot of questions in the US that you cannot ask. Things like, “What’s your religion? What’s your political affiliation? What’s your sexual orientation? What’s your age?” And then there’s like, secondary questions that could get to that, “Are you married? Do you have kids?” So you have to be really careful about that and know what the questions are and just don’t ask them. 

Vague feedback. “That candidate was good, not great.” That drives me crazy! What is that? That means…were you even in the conversation? Were you listening? So, I recommend taking notes and telling the candidate, “Hey, I’m taking notes.” And candidates love that because it feels like you’re really listening deeply and taking it super seriously. Now later on you have notes to reflect on, “Why was this candidate good, not great? What are specific examples I can tease out?” Don’t make your recruiters crazy. “Good, not great,” that makes me so mad. 

Case studies. Don’t assign these massive case studies really early in the process when someone hasn’t fully bought into your company. If you’re going to leverage them at all, and I’m not saying you should or shouldn’t, they are at the end of the process. And it’s for your two or three finalists. And I think a good structure for this is, “Hey, can you put together a six to 12 month plan, if you had the role? What are the resources that you would need?” And then, “Let’s sit down and have a conversation about it and make sure we’re aligned. Would I be willing to fund what you need and are we aligned?” And I think it’s a good baseline so that when the person does start, if they do start, you’ve already agreed on a lot of things. Obviously it would be tweaked because the person doesn’t have as much information, the insider baseline knowledge about the company as you do. And so once they get in, things will evolve.

Marquee companies. We all love a nice brand name company, and it’s okay to have that be part of the criteria, but can’t be the only criteria. Bad hires come from everywhere. So make sure you do your due diligence, even if they worked at, I don’t know, Snowflake and all of the [other] good ones. 

Being non-transparent. Over the years, I’ve had a lot of candidates reach out to me and I’m surprised like, “Hey, you just landed. What’s going on?” Well, “I was told a different story when I was interviewing and then when I got in the door, It was a hot mess! And so I’ve left and now I’m looking again.” Do not misrepresent yourself, your company and the business metrics, because what will end up happening is the person will end up leaving and then they’ll be saying bad things about your company out in the market.

Over-delegation. Sorry, I feel like I’m on a soapbox because I just see this stuff all the time, and it makes me crazy. So I’m hoping that you all won’t make these mistakes. But anyway, over delegation – CEOs, founders, you all get busy and you delegate. So you can’t do that with executive hires. You can’t have your chief of staff, your head of HR, or your internal recruiter be in the first meeting with an executive because the message you’re sending is, “This role is not important to me. I don’t give a crap about this function, and I’m super disengaged.” And so executive candidates, their spidey sense goes off and they’re like, “Okay! No thanks, I’ve got plenty of options.” 

Poor communication. So we talked a little bit about hey, be responsive, let people know what to expect. This is also things like, no ghosting. I see that happen a lot. And the other thing is, make sure you don’t ignore your backup candidate. A lot of times your top candidate may not work out. And you’re going to want that backup candidate. If you haven’t been talking to them in the past three weeks, they’re no longer a candidate. Or you’re going to have to damage control because the radio silence speaks volumes. They know that they are not your top pick and now you’re not their top pick either. So make sure at least once a week you’re sending a text or an email, a no-update update, so that they feel they’re still in the process with you. 

Mock pitches. This is specific to sales. I would not ask sales leaders to do mock pitches. However, if you were going to do it you would definitely not ask them, “Hey, do a mock pitch of my super technical product that only I and the sales engineer can actually sell,” because it’s not really fair. What you might do is say, “Hey, I’d love to know, how do you pitch your company and product? Tell me a little bit about your…” And don’t even make it like, “Oh, give me the sales pitch.” Disguise it a little bit and just see how they talk about it when they’re in an area where they’re fully ramped.

Toxicity. Do not talk negatively about anyone in the company, out of the company, customers, board members, or clients. It’s just bad. And candidates will assume if you’re talking negatively about someone who’s not in the room that you’re going to do it to them and it’s going to spook them and they’re going to walk away. So just don’t do it. Again, golden rule, treat people how you want to be treated. 

Optimize the role of direct reports on the interview panel [25:58]

And then the last area is around direct reports. So I see this a lot. Companies are small, there’s not a lot of people to put on the interview panel, so you bring in the direct reports, they’re part of the interview panel. And people get a little funky when they’re interviewing someone that might become their boss. They’re not the most unbiased. So I recommend that if you’re going to do it, you pick just maybe one to two people on the team. They only interview the finalists and you make sure that they’re not alone with the finalists. Maybe there’s two people on the team and they’re with the finalists together and that will avoid any company bashing. So I’ve seen things like, on these one-on-ones, the employee of the company, the junior employee of the company will scare the candidate with how bad everything is internally. And so if you have two people in the room, there’s less company bashing that’s likely to happen. I think another thing you could do, which I love and I think candidates really like, is a reverse interview. So it’s going to be two employees, And you tell them, “Hey, you’re not interviewing this person. They are interviewing you so they can understand everything that’s going on with the company and the team and get your feedback and your insights.” And of course we want to know what you think. At the end of the day, it’s the leadership’s team decision on whether or not this person’s going to join. So that’s that. 

Communication: The key to enhancing candidate experience [27:25]

And then if I could just leave you with one final thought, which is if you don’t do anything different, from this presentation, nothing because you just, you don’t have bandwidth, the one thing that you can do that’s very low lift and we’ll have probably the greatest amount of impact is to over communicate with your candidates. 

I think of it like, I don’t know if you’ve all heard this before, but doctors who have a great bedside manner are less likely to get sued regardless of their competency. And so, I think founders who overly communicate with candidates, they’re forgiven a lot [even] if your process sucks, but you’re communicating constantly, I think candidates can get over a lot. And so you can get away with a lot. And it’s super easy to build it into your workflow. Just add a calendar invite on your, just put a reminder on your calendar, 30 minutes every week, candidates. And you just send a text or you send a quick email, “Hey, I’m thinking about you. Sorry, we’re taking so long. We’ve got a couple other people. We’re trying to get them to the same point you are. Let me know if you have any offers coming because I really don’t want to miss out on you as a candidate.” It could be just that simple. So, I’ll hit pause. 

I don’t know if anyone has any questions.

Audience Q&A [28:38]

Audience: Thanks for that. What’s the culture here around asking a candidate about their current compensation or their expectations around compensation? 

Jaime: Yeah, no, that’s a great question. So you cannot…its state by state. So I think most companies have just adopted a blanket “Let’s just say the most strict rule and follow that.” So you can’t ask people, “What are you currently making?” And the reason is there are lots of women, other people and underrepresented minorities that have historically had wage suppression. And so, when you ask someone that and you know their compensation and you pay them the same or just slightly above, it just keeps perpetuating that wage suppression. 

But what we can ask is, “What are your comp expectations?” That is perfectly acceptable. And what I found really interesting with sales leaders is they always want to tell you their compensation. They always want to tell you because it’s high. And they’re like, “Here’s my compensation. It’s high. And that’s what I want.” But yes, that’s a good question. Thank you. I meant to mention something about that. 

Audience: Maybe one question around ‘delighting’. You’re probably hiring across multiple different job bands. And I do understand that maybe for associate managers and up [but] how do you see this delighting and going the extra mile with gift cards etc., across the different job bands. 

Jaime: I think you want to scale up the effort, the more senior the person, right? Like I think for junior people, they probably aren’t getting a lot of wooing and attention and everything. And so like giving them some, they come for their interview and they get the Starbucks gift card and they get some swag (promotional giveaways). It can be very simple. But for executive talent, sorry, this is like a pretty executive level focused presentation, but for execs you do need to go up beyond that because it just isn’t enough. Basically, to impress them with swag.

Audience: So actually wanted to ask more about reference checks and the best way to conduct them, and the reason why I’m asking is that we are now a 20-member team, and so far we have only disqualified maybe two people in the final reference checks, but there have been folks who… we have had to let them go, at least two of them. So probably there’s something that we are missing in the reference check. And I’d love to know what is the best way to conduct them and, how can you get the maximum insights out of it?

Jaime: Yeah, I am a massive fan of background checks, sorry, of referencing and back channels in particular. So the difference between references and back channels is that references are front door. The candidate has provided you with the names. Presumably these people are going to say good things. And back channels are just like through your network. Who do you know that’s worked with this person that you can get an insight back? Scoop on them and presumably a more honest perspective. It’s really hard to know from an interview 100% if someone is going to be really successful in the job, and especially if it’s in a job function that you’ve never done yourself. And I think back channels and references are a great way to verify if someone actually has the skills to do the job that you want them to do. And if they’ve got the social skills, the EQ, and they’re going to fit in well with the team. It’s harder with more junior employees to do back channels. There’s just so many of them and it’s such a vast pool. And so for those, I rely more on those front channel references. And you can still extract really good information from those even though they are provided references.

One strategy I have is to try to keep the person talking on the phone for as long as I can. If I can do like a 20-30 minute call with a front channel reference, I get really good data. Because I ask a lot of questions, a lot of follow up 30 minutes straight. They might be able to lie for the first 10 minutes or so, they’ve got like their spiel about the person, blah, blah, blah. But as you start to ask those follow up questions around, “What did this person do? Give me something where their fingerprints were on it, and they really moved the needle.” And you just keep drilling, and then you’ll get really good data even from those front channel ones. 

On the back channels, those are much easier because there’s relatively low risk for the person because the candidate doesn’t know that you’re talking to them so that they might be jeopardizing this role for them. And that’s much easier to do at the executive level. So it de-risks it, basically. It re-risks it a lot. But you have to put in the effort and it does take time. I love to do a lot of referencing.

Audience: And how do you figure out the culture fit especially at the executive level. 

 Jaime: Yeah, that’s really hard to quantify. There’s obviously like, “Did people get along with this person? Did they feel like a good fit?” And then that’s where I would be leaning on those back channels. So if you know there are certain characteristics that you’re looking for that will fit well with your culture, ask the person, “Well tell me about the culture of that company and how did that person fit in? And can I tell you a little bit about our culture? And you tell me if you think there’s some overlap with where this person would fit.” It is hard. It is hard. Mainly with the referencing and back channels, you’re looking for a history of [did] they play well with others. That’s pretty much the best you can do, I think. 

 Audience: Jaime, I really enjoyed the session. Thank you. Most of the slides you did were focused on executive hiring. Let’s say in the early stages, you want to go after individual contributors. I’ve had this one challenge where you do the love bombing, you get them for the interview. But then there are two challenges I’ve run into. One is because you were the one reaching out to them. They’re not necessarily willing to go through the grunt work or your process. Let’s say it’s a technical hire. You want them to go through a couple of assessments or head of content. You want them to do a case study. Just because you’re reaching out to them, they’re less likely to do it. That’s one challenge. And then the other thing is how many do you reach out to in the process? And then you finally find out that you’ve invested like to get five or eight interested, and that’s like a lot of time, but you don’t end up liking any. So how do you scale up that sort of process and any tips on what has worked for hiring the ICs (individual contributors)? 

Jaime: In terms of scaling, the love bombing is stuff that really should be happening with your finalist candidates. And then with the interview process, the light gentle touches of the swag and those sorts of things. You should only be love-bombing people that have an offer. So this is presumably like, one person at the end of the search. And maybe they fall through and then you have to go through the process again and you get another person. 

And then, how do you get people to do the case studies when you were the one that reached out to them to get them engaged? People are either going to do it or not. And people definitely do drop off. If it’s too crazy of a case study where you’re just like many hours of work, like nobody wants to do that. People have full time jobs. They may have families. They’re really busy. So you have to be reasonable with what you’re asking them to do. And you have to be smart when you’re asking them to do it. Like you have to get them almost to the end of the process where they are in love with you as you are with them. And then, “Hey, this is a hard requirement for us.” Maybe the case study you’re asking for is something that you can ask them to do in person with you versus a take home assignment. And so that’s easier to get people to opt into that like, “Hey, we’ve got this case study. You can either take it and spend an hour on it or you could do it here. We can give you a laptop,” and just make it very low lift for them to opt in. But yeah, definitely people will drop out of the process over that. 

Audience: How do you make it scalable? I mean, you do it with seven, eight people and you don’t end up liking any, but you wait for a month or two. So is there something that we’re doing wrong in like, going after the right people? 

Jaime: Well, it’s hard to know without seeing who you’re going after. I wonder if everyone uses the term ICP, ideal customer profile. You could say the same for candidates. Ideal candidate profile. Are you targeting people from, marquee? Are you overemphasizing marquee companies? And they’re like, “I don’t really want to go to a startup. And this seems like a lot of work. And they’re making me do this assessment thing!” I just don’t have enough info to be able to tell you for sure what the problem is with the process. 

But I suspect if you have that many and you don’t like any of them, then maybe something was wrong with the original profile that you’re targeting. 

Audience: So what are the typical expectations of the candidates around working long hours, [working] weekends and that kind of stuff, especially in this area. Because there are certain geographies where people are very opinionated about work-life balance and not working long hours.

Jaime: Yeah, that’s a great question. 

Audience: I think, Jaime, I’ll quickly ask a follow on question because you just said something about not being too crazy with things and I was talking to a founder last week before joining Peak XV. I was working with a company located in the US and we were talking about how a process should be and they, I just asked them, “Hey, for an early, because we were talking about people early in their careers maybe this is a rapid fire question and we could work later on creating a resource for everyone but they mentioned that they do at least eight, nine, rounds of interviewing, no matter who they’re hiring. And it’s probably a practice like common practice in India, just doing like very, having very long hiring processes. So if somebody is hiring in the US what’s typical, I know there are startups in the US that hire pretty quickly, and maybe that’s also too crazy, just like doing two rounds of interviews and you just get a job. But what’s typically a good process for executive and also IC hiring? That’s really typical in the US. If you could share that. 

Jaime: So let me answer his question first. I might ask you to repeat yours because my memory sucks. So I do think, as I mentioned, back in 2010, the war for talent started. And even though we’ve had layoffs the last couple of years, and the macro [economy] here is not great, I can tell you that good people are still working or they’re sitting on the sidelines acting like they’re venture investors, about to invest millions of dollars in your company. 

Going on and saying, “Well I don’t know about the valuation!” and asking all the hard questions on the metrics and stuff. They’re being incredibly picky. So no, they’re not going to come in and work insane out. Yeah, they’ll probably do 10-hour days, but at the exec level, most of them have families. And a question that I frequently get is, “Oh! These founders are from India, Southeast Asia. What does that mean for calls and stuff? Am I going to be on calls late into the night or super early in the morning?” Because they have families and so they’re expensive and they’re not going to work 12-hour days. With IC level folks, I have a little bit less experience there, but my team did a lot of recruiting of engineers and my sense was, yeah, there was a lot of entitlement there as well because they were in such crazy demand. And so maybe some of it simmered out a little bit because of the layoffs, but yeah, I don’t think you’re going to see people working insane hours. 

And then as far as like the optimal number of interviewers, so Google did like an actual study many years ago because they were sitting on all this interview data and they’re very quantitative in their hiring process, and they uncovered that, four interviewers was the optimal number to predict job performance, at least in the context of Google. So I don’t know if that data still holds or stands, but I would say, it’s probably somewhere between four to six interviews. And the CEO or the hiring manager should meet with the candidate multiple times. You can’t make a decision based on one 45-minute [session] and neither can the candidate. There need to be more touch points than that [to assess], “Hey, can we work well together? We are going to work together, so how’s this going to go?” 

But yeah, I think eight to nine meetings, where it’s eight or nine individual interviewers, that’s too much and it’s not predictive. And if anything [at all] it decreases the chance that someone’s gonna get over the finish line. You’re gonna get a lot of false negatives, it’s not gonna increase the positives. So yeah, I would err on fewer interviewers and more time with the CEO or the hiring manager, whoever that might be.

Audience: You touched upon rejecting candidates earlier by giving them constructive feedback. So I have a question both for that use case or that scenario and firing employees. So I’ve seen a lot of companies don’t actually give feedback because they’re afraid of legal ramifications. So do you have any thoughts there?

Jaime: So, for that, I’m not a HR expert. I would definitely talk to whichever attorney you’re working with over here, because they’ll have a perspective on it. But how I think it’s typically played out is that people shouldn’t be surprised when they get fired, right? They should have been getting feedback all along the way about their performance and how they could be improving it. So when you actually do let them go, it should not be a surprise. And there shouldn’t even need to be a discussion because they know, they’ve gotten all this feedback on why things [happened]. There’s no need to rehash it at that moment. You’ve made your decision, you’re moving on. And yes, there is this risk that anything you say could be used against you in court, and so you want to keep it really simple when you are letting someone go and not give them a ton of feedback, but hopefully give them lots of feedback along the way. Did I answer your question? 

Audience: Yes, but is that not a concern when rejecting candidates during your interviewing process? Or is that the same situation there? 

Jaime: No, I think it’s fine. If it’s job-based and it’s not, “Hey, I didn’t like you!” Or like, “You’re not a culture fit!” So it has to be facts and it is something like a gap. They don’t have it in their background. 

Audience: I’m curious. Earlier today we were talking about the first 10 employees being typically generalists and that’s pretty common. But when you go from 10 to 50 employees, I’m curious what, if you’ve got an opinion on whether you should bias more towards generalists still or more towards specialists. Obviously you can hire extreme specialists, but sometimes that can be too early. And if there’s a right way to approach that, especially when you’re looking at bringing entirely new functions as well. 

Jaime: Yeah, I do think there is a point where you definitely need to have specialists. Otherwise, everyone’s going to be running around learning how to do things on the fly and you do need experts at a certain point to help move the needle forward in your different functions. I remember with DoorDash, I was working with that CEO when it was just launched. It was a tiny baby company. And he had that model. He loved hiring really smart people with consulting backgrounds and that took them surprisingly far actually. But eventually they had to hire their first executives and they almost skipped a phase. Like, for a lot of companies their first specialist will be director-level and they skipped that. And then they had to hire VPs like straight up. And there was a bit of a learning curve of, “Oh, how do we work with these VPs who are functional specialists,” and they hadn’t really done it before when it was lower stakes. So I think they actually waited too long. It didn’t hold them back. They’re obviously a very successful company. But yeah I do think at a certain point and it is usually like, you start with a head of… or a director. And then, eventually you bring in the VP above that person. 

Audience: So, let’s say if there is a specific role and my team ends up interviewing 10 to 15 people. And otherwise, [in another situation] they might end up interviewing two people and then hire them. Is it too quick?

Jaime: Oh, like how many people is the right number of people to get to who is your [right] person! Yeah. I don’t think there’s a magic number there. I’ve seen, there’s like this recruiting funnel where it’s like, “Okay, you have to reach…” And this is specific to the US and again, this is also specific to the talent war. You reached out to 100 people. Hopefully you get some sort of response from 30 of them. Maybe you get to phone interview 10 of them. And then maybe, three of them, come for an onsite and of those three, you pick one. And again, that’s been the US situation because it was so hard to get candidates to engage and respond. And so you had to reach out to a high volume. So, I don’t think there is a magic number and even if you’re bringing people in for an onsite, you need to be constantly adding new people to the pipeline, because you just don’t know who ultimately is going to get the role, right? You can have people interviewing on site and none of them could be a fit, and hopefully, the recruiting pipeline didn’t stop. 

But yeah, no magic number, but if you followed that funnel, I guess it would be three for an on site to get to a yes, potentially or seven to eight like that gentleman. Okay, anyone else? All right thanks everyone. 

This transcript has been edited for clarity.