Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, General Catalyst)

Lauren Ipsen (00:00:00):
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing. And I think that should be the case for both candidates and folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So, both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well known commodities in their organizations and get great references.

Lauren Ipsen (00:00:35):
Oftentimes, I encourage founders to simply chat with what good looks like and get a really good sense of what benchmark candidate profiles could be, and who knows where that person will be in a year or what have you, but staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.

Lenny (00:01:05):
Welcome to Lenny's Podcast. I'm Lenny and my goal here is to help you get better at the craft of building and growing products. Today my guest is Lauren Ipsen.

Lenny (00:01:15):
One of the most important skills for founders and senior product leaders to develop is the ability to hire great people. You won't be able to build the best company or the best product if you can't hire the best people. And Lauren is one of the most experienced and successful people in the world when it comes to hiring product leaders. She's placed over 80 senior product leaders across tech companies and has worked with some of the biggest companies out there. When I asked a bunch of really smart product leaders who their favorite product recruiter was, Lauren's name came up a ton.

Lenny (00:01:46):
In our conversation, we get super tactical about what founders need to do to find the best product talent, what product managers should be doing during their career to give themselves the most opportunity, and we also touch on what recruiters themselves often get wrong when trying to attract great talent. This episode is rich with actionable advice for basically everyone, and I am really excited to bring it to you. With that, I bring you Lauren Ipsen.

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Lenny (00:04:45):
Lauren, thank you for being here. Welcome to the podcast.

Lauren Ipsen (00:04:47):
Thanks so much. It's great to be here.

Lenny (00:04:50):
I've been meeting to do an episode on product hiring and recruiting product people for a while, and when I asked a bunch of smart friends who should I have on to talk about this stuff, your name came up a bunch, and so I'm really happy that we're finally doing this.

Lauren Ipsen (00:05:03):
Me too. Absolutely. I'm grateful that you asked.

Lenny (00:05:07):
So, to help listeners get a sense of just your background and kind of the journey you've been on to get to where you are now, can you just spend maybe just a minute kind of talking through the wonderful things you've done in your career and what you're doing now?

Lauren Ipsen (00:05:19):
Yeah, absolutely. So I started my career in broadcast. I originally thought that I wanted to be on the news and quickly realized I didn't necessarily want to be the face of sadness. There's a ton of that happening in the world.

Lauren Ipsen (00:05:36):
So, made a pivot pretty early on and thought, where could I use the communication skills that I've been working so hard on and do something that's impactful in a big way, but maybe just with a little bit of a different angle? And stumbled across executive search.

Lauren Ipsen (00:05:52):
Exec search is not really something that people major in college by any means or think they're going to end up doing. So it was something I found fascinating. I had applied to all of these different companies like Twitter and Snap and Pinterest, hadn't heard back from any of them, was a name in the resumes, and thought, well, how cool would it be if I could work with all of them and have an opportunity to play a part from a different lens?

Lauren Ipsen (00:06:18):
So, got into exec search, was really focused early on on consumer mobile build outs. Was doing a lot of work with Twitter and Reddit and TaskRabbit and Nextdoor, Postmates, you name it, and that was probably 85% of the work I was doing. And then as, on the agency side, 15% was obscure, autonomous helicopters selling into the Department of Defense and then retail and robotics, and it was all very fascinating, but for me, who has wicked bad ADD, it was amazing to be able to be so stimulated by so many different industries and feel like I couldn't really master this.

Lauren Ipsen (00:06:57):
So, long story short, had an awesome career at Daversa Partners, which is a boutique executive search firm, and thought I was going to be there potentially forever. Was tapped by a awesome individual, Abe Shafi, who was founding a company. I had been doing a lot of work for them. They were a client of mine at the time. Placed a couple great hires and they said, "We're either going to kick off a head of talent search with you or you can come over and join us." So I was the first recruiting hire over there, built out the talent function in its entirety.

Lauren Ipsen (00:07:27):
I definitely think there was a part of me that I loved the operating experience, learned a ton, worked side by side some amazing people, but was really missing working with founders, and lots of them, and keeping a pulse on the market. So General Catalyst tapped me most recently, and been working here for the past couple months, and it's been great thus far, and I'm specializing in our consumer and crypto investments.

Lenny (00:07:51):
Awesome. The fact that you're at GC now makes me think about another recruiter that I know who's awesome, Austin Brizendine, and it's interesting that a lot of the best recruiters seem to be heading to VC funds, and I'm curious why that is happening. Is it like a comp thing? Is it other things that are pulling everyone away into funds?

Lauren Ipsen (00:08:09):
It's a great question. It's definitely not a comp thing. I'll say that. I think it could be a stability of life thing. Search is incredibly volatile, and you have to hustle so hard, and as soon as you have three wins, you've got four more things to execute on. And so, there's aspects of it that can be tough, especially in a market like right now where you really do have to chase business and you can't be selective about what you take on, so you could be pitching things that maybe you don't necessarily believe in in its entirety or what have you. So, I think that's one component.

Lauren Ipsen (00:08:39):
In house is obviously difficult right now as well for talent leaders. It's really scary to take a bet on one single company right now and know what it's going to look like six months from now. And so I think those things combined might be the reason for an influx in folks leaning more towards venture, and I think it's just timeliness.

Lenny (00:08:59):
Got it. That makes sense. The downside is it's hard for people to find awesome recruiters because once you're in a fund, you're just going to help those startups. And so we're going to talk later about just how do people find awesome recruiters, what do you look for? But there's roughly three things I want to spend our time chatting through today. One is for founders and hiring managers, just how to find the best talent and what they could do to be successful finding the best talent. Two is for product leaders and PMs, how to give themselves the most opportunity from the flip side. And then third is just for recruiters, what do they often do wrong? How do they miss out on the best product talent? Does that sound good?

Lauren Ipsen (00:09:37):
Yeah, that sounds great.

Lenny (00:09:39):
Okay, cool. So on the hiring front, just diving in, say you are a founder, you're someone really early at a company, and maybe you've got a couple PMs and you're starting to think about we need to hire a really senior product leader or first senior product leader.

Lauren Ipsen (00:09:52):
Sure.

Lenny (00:09:53):
What do you find is often the biggest mistake that founders make when they're trying to hire their first senior product leader?

Lauren Ipsen (00:09:59):
I think especially for founders that haven't hired for this caliber of talent in the past, it's really easy to be distracted by shiny objects and look at huge names. You want to find the CPOs of Google and YouTube or what have you because that seems like it would be such an incredible opportunity for brand recognition. And to an extent, it is. But the fact of the matter is, oftentimes those individuals are pretty far from the work and have a great team of executors that they've put into place that are actually the ones that are in the weeds.

Lauren Ipsen (00:10:33):
And so I think that's the biggest mistake I see people make, especially on the hiring front where they have limited resources, and maybe they're an early stage company and trying so hard to bring in big names is not always the best way to go about it because the fact of the matter is they need to go then hire a team. So, I think looking for someone that's a little closer to the work, maybe someone that can step up into that type of role and do so in a way where some days they might actually be operating like a PM and then other days they might be able to build from a leadership perspective, that's more of the DNA that people should be targeting.

Lenny (00:11:09):
Do you think the source of the issue with that going wrong, that they no longer can do that work as well because they've been shielded away from the tactical day to day? Or is it that they're not as hungry as they used to be and they're just like, "I already, I'm a YouTube 10 year super success, I don't need to prove myself anymore," and they're just not as hungry, or something else?

Lauren Ipsen (00:11:29):
I mean, I'm not going to sit here and say that all senior leaders aren't hungry. I think that there's some folks that really lean into the work in a different way and miss that, and often go to startups because they crave building.

Lauren Ipsen (00:11:41):
So it's not necessarily that, but I do tend to lean towards folks that have a chip on their shoulder or have something to prove and want to build a name for themselves. All of that to say, there's a reason that a lot of those people got to where they are, and some of the best talent are some of the senior folks, but just maybe not necessarily the best talent for where this company is today. Right? It could be great for 10 years down the road, but the past five years of that individual's career could have been far more focused on camaraderie, team building, operational components, performance reviews, and then aspects of product vision, which just might not be the innovative AB testing type of profile that you typically look for in these pre-IPO companies.

Lenny (00:12:27):
Got it. I imagine there are stories that you can share about people you've placed like that, that have not worked out. If you can share one, that'd be awesome. But maybe a side question is the general advice, just don't assume someone that's been successful at a big company with a fancy background is going to be great. Sometimes they work out, but not always, is that kind of the takeaway?

Lauren Ipsen (00:12:46):
Yeah. I would say the general advice is who is going to be best for this specific role at this specific time, not necessarily who is the best talent in the world or in the market. Those are two very, very different questions to ask. And I think early on in my recruiting career, I was often just trying to recruit these whales of executives to try and prove myself and say, "Oh, I got this person to entertain this opportunity, how sick is that?" But naturally, that's not necessarily the person that actually can move the needle. And so you need to think very specifically. Just because this is the best talent, that doesn't necessarily mean they are the best talent for this role today.

Lenny (00:13:25):
So to double down on that, say you are hiring and you know you're going to start hiring a senior product leader, what is it that you suggest founders nail down and iron out when they're kicking off the hiring process, either on their own or with a recruiter? Like, in the job description, what else do they have to get right to find the right person?

Lauren Ipsen (00:13:48):
It's a number of things, like product leaders can come in a lot of different flavors, and so I think it's trying to determine where this person should major and minor, where they should spike. Is this someone that's going to really lean into the design efforts? Is it someone that actually kind of needs to just operate like a very senior PM and continue to build out a team? Is this someone that really should be focused on product vision for the long haul? And then thinking more holistically about how to build the rest of the team.

Lauren Ipsen (00:14:12):
There's so many different ways in which you can hire for a product leader. So I think it's trying to work a little bit backwards and think about, what is the actual outcome that we are trying to solve for with this hire? Or are we just hiring a head of product because we feel like we need to hire a head of product? That's so often what I see is the board's telling me we need to hire a head of product and I don't necessarily think that we do, or I'm not exactly sure what we need in this role. And so whenever you're starting a search in that regard, it's kind of doomed from inception, so you need to get incredibly granular on the front end around, what is this person going to be coming in to do? What's their mandate? And if we think about someone that's just absolutely hitting it out of the park and crushing it, what does that look like? So I think just trying to be really specific on the front end.

Lenny (00:14:59):
I love that last piece, just what does success really look like for this person? On the first piece, that's exactly the same advice I give founders when they're looking for a PM is like, what do you concretely need them to do day to day? Not like, "We need someone to help us with product." And that often helps illuminate, okay, I see. We need someone to help us ship more consistently. We need someone to help us hire engineers. Yeah, just make a list. What are they going to do in the first month or two or three?

Lauren Ipsen (00:15:24):
Yeah, yeah, absolutely. I think those are the most important things. Like the 90 day plan is something that's overused but so necessary, and that's just the tip of the iceberg. So that component and then, okay, a year from now, what should this person be doing? Two years from now? Do we want them to grow up into a CPO role? Do we think about that in a different way? How are we thinking about the product direction today, 12 months from now, 18 months from now, through IPO? I think it's really difficult to think about things that way, and so often you're thinking about the task in front of you and just trying to iterate quickly, but that is the type of thought process that needs to be happening from the CEOs and founders.

Lenny (00:16:06):
Are there archetypes of PMs, if you just bucket like here's the three maybe most common types of product leaders that founders hire, because there's an infinite list of skills and things they could do, but just to make it even simpler, like here's probably one of these three you're looking for. Do you have something like that in your head?

Lauren Ipsen (00:16:25):
Yeah, there's platform product leaders or folks that are kind of more indexed on the infrastructure components. There's folks that are typically focused on core product, or consumer product if it's on the consumer side of things. And then you'll have folks that are really indexed and that can include UX individuals, design folks. And then there's also typically specialists, so individuals that are really hyper-focused on growth or monetization or what have you. Those are the three buckets that I would say I see most often.

Lenny (00:16:57):
Do you feel like founders sometimes pick one of the wrong buckets and that's a common mistake, or is it generally it's the wrong bucket but then maybe it's not the right spikes of skills within that bucket?

Lauren Ipsen (00:17:08):
Well, it's kind of twofold. I think sometimes people just bring in a head of product to do everything, so that's probably not the best way to go about things. I think that ends up being a unicorn, which you hear often in the search world, and it becomes really difficult to hone in on what good looks like.

Lauren Ipsen (00:17:25):
And so I think again, it just comes back to having a clear org chart on the front end and determining, are we hiring someone specifically to build out our walled garden ads approach, or are we hiring someone to run product marketing, or are we hiring someone to help from a product perspective to build a better core user experience? Those are all very, very, very different roles, and if you bring in one person to try and do it all, the facts of the matter is, they're going to have to bring in some key lieutenants to help them, so is that something you want to do or are you more focused on bringing in someone imminently to help on the ad side of things, and then we can find that head of product to help them out down the road?

Lauren Ipsen (00:18:05):
That's kind of the way in which I would architect it and think about it, is what's most imminent, and what do you actually need to hire for today, as opposed to just hiring for the sake of hiring and bringing in that leader.

Lenny (00:18:17):
And part of the discussion there is maybe they grow up into this head of product long term, maybe not. Maybe we just need someone to ship the ads platform, right?

Lauren Ipsen (00:18:24):
That's exactly right. Yeah.

Lenny (00:18:26):
You mentioned this title of head of product. There's also VP of product, CPO. There's all these titles and I feel like people sometimes use them interchangeably, don't know which one to use when they're putting out a job description. Do you have any kind of heuristic rule of thumb of just, here's how to think about when to use each of these titles? Or is it not even a big deal for, say, a founder, hiring the first senior product leader?

Lauren Ipsen (00:18:48):
It's a great question and it definitely leads to confusion across the board because I'll have candidates come to me and they'll say, "I'm only looking for a CPO role," when I'm working with a startup where, maybe on the venture side of things, we've actually advised that startup to not hire C-level executives at this point. And so that naturally could eliminate a candidate that could be amazing for the role.

Lauren Ipsen (00:19:15):
Similarly, people could feel that way if it's a VP of product role, but that in their mind is the most senior product leader within the organization running everything from end to end who they intend to be the CPO down the road but are not in a position where they're ready to hire C-level execs. So, it's tough, and it really depends on the organization and the way in which they're thinking about org charts and leveling.

Lauren Ipsen (00:19:39):
A lot of startups at this point are almost allergic to C titles or VP titles or are just more title agnostic than I've seen in the past, so you see a lot more of these head ofs, and that is sector leaders, up until probably C plus or D stage. And then you get to D and E, and you'll see more of the VP, director, CPO type. And I think that is the way that people should be thinking about it is, if I'm joining a company very, very early days and it's called head of engineering, that is intended to be the most senior engineering leader within the organization.

Lauren Ipsen (00:20:19):
The fact of the matter though is there's good reason sometimes why they're not throwing out that C title, and could this person be layered down the road? Potentially, because maybe the talent they need right now is different than, just as we had spoken to earlier, is different than the talent that they might need from a massive CPO in two and a half years.

Lauren Ipsen (00:20:37):
And so I think that rubs people the wrong way because they want a bit of a promise that things are going to, if they join at this stage, that they'll be in it for the long haul and be that chief product officer that takes a company through an IPO. But companies are so dynamic and things change so quickly.

Lauren Ipsen (00:20:52):
So, I guess a long-winded way of me saying there's different breadth and depth to each role, but I think for the most part, unless it's a very siloed company with multiple different VPs, if you're coming into a company and they say this is the head of product, the VP of product, or the CPO, that all means the same thing dependent on the stage, for the most part.

Lenny (00:21:14):
And the other takeaway there, which is awesome, is if you're early stage startup, probably just start with head of product. Keep it simple.

Lauren Ipsen (00:21:19):
Yeah.

Lenny (00:21:19):
Don't over promise. Everyone understands.

Lauren Ipsen (00:21:22):
Yeah. Because the last thing you want to do is have to demote someone. But once you get to a place of having C-level executives, like that's not going to do any good, but maybe you start as a head of product, and then as the company continues to grow, you lean into the growth side of things more, and so you become that head of growth or an SVP of growth. Like things iterate and change, but you just never know and you can't predict the outcome of a company on the front end, so.

Lenny (00:21:49):
A lot of people listening to this probably aren't hiring senior product leaders right now, but plan to and will in the future, and so I wanted to ask, what should founders do when they know they will hire a head of product, say, in the next year, that could set them up for success down the road? What should they be doing ahead of time?

Lauren Ipsen (00:22:07):
Regardless of whether or not you're hiring, you should always be keeping a pulse on the market. That is the most important thing. And I think that should be the case for both candidates and folks that are hiring. Like, you never want to put yourself in a position where you have no idea what good looks like, whether that's from a company standpoint or from a candidate standpoint. So, both parties should always be having a good understanding of which companies are thriving, which individuals are building great things and are well known commodities in their organizations and get great references.

Lauren Ipsen (00:22:43):
Oftentimes, I encourage founders to simply chat with what good looks like and get a really good sense of what benchmark candidate profiles could be, and who knows where that person will be in a year or what have you, but staying really, really close to really great people and using them from an advising capacity or getting them ingrained in some type of involvement in the product prior to actually having that specific need, I think, is really important.

Lenny (00:23:11):
That sounds awesome and it makes sense. How do you, as a founder, do some of that? Do you just ask folks like, "Hey, who are some of the best product leaders you know? I just want to chat with them. I'm not hiring, just want to kind of meet people who are awesome." Is that the behavior you suggest or is there something else you can do?

Lauren Ipsen (00:23:27):
That's a great way to go about it. And by simply saying, "No agenda, I'm not trying to hire you tomorrow, I just want to know great people." And to be totally honest, people feel flattered by that, typically. Most of the time if you've been referred to someone and heard nothing but great things about them and you really don't have an agenda other than wanting to pick their brain, people are like, "Huh, well, this is different from the day to day. This is fulfilling," and people want to pour their knowledge, especially into companies that they believe in.

Lauren Ipsen (00:23:58):
So, I think more often than not you'll find that, not just products leaders, but executives across the board are actually really inclined to do so and want to help out because it's a little bit different from the day to day monotony of their work life.

Lenny (00:24:12):
So, the advice is keep track of companies who are killing it, who you might be able to kind of poach from in the future, and keep a list and keep warm contact with folks that are awesome.

Lauren Ipsen (00:24:22):
Yeah.

Lenny (00:24:23):
It reminds me of a founder that ... or basically all founders who are really good at hiring and how far ahead they plant seeds and how they just play the long game with the best people they meet, and they just kind of keep the conversation going until they finally convince them to join a year or two later. Do you find that the same thing?

Lauren Ipsen (00:24:41):
Yeah, 1000000%. Yeah. When I was on the executive recruiting side of things at Daversa, the VP of engineering candidate that we ultimately landed, it was a seven month game of courtship, and let's bring him in to help out from an advising capacity, let's ask him how he would think about structuring this organization, let's talk to him about the best talent that he would recommend that we're spending time with. No question that's invasive, but more so just collaborative and exciting, and you'll find that the founder and that leader will build a different level of rapport and trust by not going through a formal interview process and having it feel transactional. And then with that, magic can happen and you can land incredible people.

Lenny (00:25:24):
This all sounds like a lot of work and a lot of time. Do you have guidance on how long it should take to find, like for a early stage startup, say series A or B, to find someone awesome, and/or how much time founders should spend a week, just best practice, on hiring for someone like this?

Lauren Ipsen (00:25:41):
I mean, I think if you're going to search, so if you're looking for this individual, it's really so case to case. There's searches that I've been in that I call three people. I know they're amazing for this. I tell the founder and CEO, "These are the three people you should chat with, hire one of them." And it's that easy.

Lauren Ipsen (00:25:59):
There's others where it's a lot of trying to figure out what the person's actually looking for. If there's some ... they hit it off from an emotional standpoint. There's so many different things that come with it. I would say from a timing perspective, it's not a hard number. It's more of just put yourself in the room with great people. If you have a tremendous amount of respect for someone, continue to harvest that relationship and ask what good looks like. Find excuses to continue to touch base with people that are important in your network. If you remembered that they'd mentioned that they were going to some event and you think that you might want to hire them down the road, in a non-creepy way, show up to that event. These are things that I'm constantly doing, and I think that founders can do a better job of, but just make yourself known and relevant. And then when you reach out and timing is right, it won't feel so obscure or so transactional.

Lenny (00:26:55):
That reminds me of a time at Airbnb where we had these meetups for engineers every month or so where it was a tech talk, and then all the engineers get a target engineer that is coming to the event. Like they get their profile and their picture, and their job is to make sure they have a great time and try to convince them to join someday.

Lauren Ipsen (00:27:14):
Oh my god. But it's so real. It's similar to college trips where you're trying to get recruited for a sport, and you have to ensure that you're, yeah, just continuing to give people the best experience possible and staying top of mind for people.

Lenny (00:27:28):
Yeah. But I can see it being creepy, They have no idea there's this person assigned to them, but it works. It worked great. It was a great tactic.

Lauren Ipsen (00:27:35):
That's awesome.

Lenny (00:27:36):
I want to come back to a question that I asked, but I feel like you'll have an actual more concrete answer to the specific piece of just, what's your guidance per week how much time you should be spending on hiring broadly, and specifically, heads of product, if that's any different. Do you have any just advice? Because I imagine it's always spend more time than you think. It's going to take a lot of time.

Lauren Ipsen (00:27:54):
Yeah, it's definitely spend more time than you think. If you are in an actual search, then you should devote all of your time to it. I know that sucks to hear, but you should be really carving out concrete time.

Lauren Ipsen (00:28:05):
The thing that's tough though is you could spend, I guess what I was trying to say is you could spend one hour on something or you could spend 10 hours on it, but it's more so around, are you doing things to be impactful during that period of time? Are you actually doing things that are going to move the needle? Are you just blindly reaching out to people on LinkedIn? Because that's not going to be the way in which you're going to find the best of the best. Some of the greatest talent, they're not even on LinkedIn.

Lauren Ipsen (00:28:32):
And so I think it's building a really strong network in advance, and then once you actually get to a place where you need to hire that person, calling all of those amazing people that you've built relationships with and saying, "Now tell me who your favorite person is and who the best person you've ever worked with is, and could you put me on a thread with them?" How are you going to differentiate yourself from the rest of the market? So it's less in my mind like a quantitative number of hours and more of, how are you doing things differently than the rest of the market?

Lenny (00:29:01):
I want to pull on this thread. Okay, so spending one hour versus 10 hours, and your point about how you could spend one hour and get as much done maybe in those 10 hours. What sorts of behaviors and actions should folks take to make use of, say, that one hour in hiring? How do you not waste your time?

Lauren Ipsen (00:29:18):
I mean, I would say I've got probably five of my all time favorite product leaders in the world that I tap whenever I'm kicking off a search. And they know that whenever life brings them to an opportunity where they are going to start looking or want to lean into board opportunities, that I'm going to set them up and shout their name from the rooftop, so oftentimes they're willing to point me in the right direction of great people, make those introductions, what have you, and I'm going to know simply because of how great they are that they would never put me in touch with someone that wasn't equally as qualified.

Lauren Ipsen (00:29:55):
So that I think because the quality is there, so I'm not just blindly guessing on quantity, spending a ton of time on LinkedIn, and then having to call unknown entities and ask for back channel references when they also might not even feel comfortable sharing the dirt. You know? So it comes back to rapport and people that you have around you that you know you can trust and tap into and ensuring that you're spending the time in the right areas.

Lenny (00:30:19):
Got it. Yeah, so tapping your network makes a lot of sense. If you don't have that yet, I guess is it worth spending time on LinkedIn just cold messaging people as a founder, and any tips there for just cold outreach that you think work for a founder doing it versus you who are a professional at it?

Lauren Ipsen (00:30:37):
I do think it is worth that time. If you see someone that looks amazing, hell yeah, reach out to them, spend time with them, why not? And oftentimes, again, people are excited to see, oh, this CEO and founder wants to pick my brain, doesn't look like they're coming at me to try and recruit me, but rather just to have an open-ended conversation. For sure, and they can sense. You can definitely sense that type of interaction and feel comfortable with it, whereas sometimes the walls immediately go up when someone senses that they're trying to get poached.

Lauren Ipsen (00:31:08):
And so it's I think something that's worth them doing for sure. It's just if you are going to look for a key executive and are on a time crunch, I don't necessarily think the best use of your time is blindly reaching out to executives when you don't necessarily have the expertise in knowing which companies were thriving during that period of time, which organizations were great, and which were a little bit weaker within companies. All of those things are just the inner workings of the recruiting atmosphere and technology, and I think tapping people, if you don't have the network, talk to a great recruiter or just spend some time kind of doing some research on who's great. You can ask investors or board members in your companies as to who you should be targeting. So there's always got to be one or two people that can at least point you to another three or four.

Lenny (00:31:56):
That reminds me of a tactic Gokul shared on this podcast about one of his best tricks, as you think of, if you're hiring salespeople, instead of looking for who are just the best salespeople, you look for the company that is known for being really good at sales and then you go find people there and try to poach their lieutenant types, not maybe necessarily their head of sales. Do you think that's a good move?

Lauren Ipsen (00:32:17):
Yes and no.

Lenny (00:32:18):
Ooh.

Lauren Ipsen (00:32:19):
Yes and no, because I think if the organization is incredibly good at sales then the majority of the folks are probably amazing, but you always have weak links, and just because someone has a brand on their resume at the right time, I think oftentimes CEOs and founders will do this thing where they kind over generalize, well, Amazon's Prime team at this time was amazing or something like that. It's like, they definitely could have been, but just as any other company, there's going to be people that are breakout, top 1% type individuals, and then other individuals that get to ride the wave and reap the benefits of being at the right place at the right time. And I think that's a good starting place, but then also spending time getting a little bit deeper on who the best people are within that organization. But yeah, we always start with market mapping, so determining who the best companies are within a specific area, and then I just encourage everyone to take that a layer deeper.

Lenny (00:33:16):
Got it. It just comes back to your previous piece of advice. Don't assume someone that has an awesome logo is going to be great, but sometimes they are. There's a question I should have asked you at the beginning that I'm going to ask now. How many folks have you placed? How many companies have you worked with? And then also, is there a story of just your favorite person that you've placed/company you've helped hire that comes to mind?

Lauren Ipsen (00:33:36):
Yeah. So both great questions. I've placed probably 85 executives over the course of my career, and then lots of entry level employees when I was in house, and also some great key leaders. Yeah, probably 85 searches that I've opened and closed, so that's been incredibly fulfilling work. It's also fun too on the exec side of things because you hire the VP of engineering at Postmates and you see firsthand the product change. You know, you watch those types of things happen before your eyes, which is, it's fulfilling stuff, it's really cool.

Lenny (00:34:09):
And delivery gets there faster too.

Lauren Ipsen (00:34:10):
Yeah, yeah, exactly. So, that's really fun. Favorite placement of all time has got to be the VP of engineering that I placed at IRL, which is, to be completely honest, a big reason that I joined that company. Alex Strand is his name, and he is just the most incredible, atypical, high emotional intelligent engineering leader. Still super technical, but has managed teams in the hundreds, built out Amazon Prime Day, then went on to build the core messaging platform at Snapchat, called him and he was like, "Why would I ever leave? There's a ton of financial incentive and a team that I've built that all loves me."

Lauren Ipsen (00:34:54):
And we got him to ultimately make a move in two weeks, which is just kind of unheard of, although it ended up being like a seven month push for a start date, but that was a big reason why I went and joined IRL was to work side by side him and help build out his team and learn to get more deep on the technical side of things. Because oftentimes, on the executive level, as mentioned before, can be sometimes more of that people management type role. And so he just felt like this unique hybrid of an individual, and yeah, you close searches and you cross your fingers and hope for the best and feel very good about it, but he was one where I had all the confidence in the world that I could not have done better. You know? I just felt so great about that. So, that was a good one.

Lenny (00:35:38):
I don't know how much more confidence you could instill in a candidate joining a company than the recruiter also then joining the company.

Lauren Ipsen (00:35:44):
Yeah, I did say that to him. I kept saying, "And if I were to go in house, I swear this is probably the company I would do it for." And then about four weeks after he signed, I'd texted him and I said, "Well, you'll never guess."

Lenny (00:35:58):
Wow.

Lauren Ipsen (00:35:58):
Yeah.

Lenny (00:36:00):
Amazing. What a stamp of confidence.

Lauren Ipsen (00:36:02):
Yeah. And a full circle life moment. I sent him a box of cookies, he sent it back and said, "Your turn."

Lenny (00:36:07):
And is he still there at IRL? Awesome.

Lauren Ipsen (00:36:09):
Yes, he is. He's great.

Lenny (00:36:12):
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Lenny (00:37:29):
I want to shift a little bit to kind of flip to the product person's perspective and talk about, how do you be successful as a product leader in finding new opportunities and giving yourself opportunities in the space? And so maybe a first question is just generally, what should product leaders and PMs focus on to give themselves the most opportunity in their career?

Lauren Ipsen (00:37:51):
I think breadth is incredibly important. It's so critical, especially if someone has an end goal of wanting to step into a product leadership role to have been able to have touched lots of different components, as opposed to specializing in one specific thing. So I would say that's very important, to be able to make sure that you're maximizing opportunities for yourself down the road.

Lauren Ipsen (00:38:12):
And then as mentioned before, just always keeping a pulse on the market, regardless of how happy you are in your current company, regardless of what the project is that you're so incredibly excited about that isn't going to conclude until Q1 of next year. It's just so important that you always know the companies that are doing great things and keep those windows open for people, because you never know what the next 12 months hold, and you want to be in a position where you're never running out the door looking for what's next, but rather being able to be super selective about the things that you have in front of you. And that comes with time and network building and relationship building over years, honestly.

Lenny (00:38:54):
And when you say breadth, are you saying things like work on the platform team for a bit, work on the user facing team, maybe the internal tools team, like different types of product, or something else?

Lauren Ipsen (00:39:04):
Exactly that. Yeah. I think there's people that probably want to just be a specialist in growth, or want to get super deep on ads, and if that's the case, then by all means, do so. And I think there's something to be said about that as well because those types of skillsets will be needed. But if you're looking to diversify your skillset, continue to grow from a career trajectory perspective and think about potentially being in a head of product type role, I think it's really important that you touch all aspects of that.

Lenny (00:39:38):
I'm really happy to hear that because that's exactly the advice I give new PMs is that a variety of experience is one of the most powerful things you can do because you also just become a better PM because you can see how different types of products are built and how different types of teams operate and it just makes you better.

Lauren Ipsen (00:39:52):
Yes. Variety of experience, I think taking a bet on doing something more entrepreneurial, starting something, and then also joining things that are a little bit later and more established to get best practices. I think diversifying your skillset within an organization but also diversifying the work in which you're doing and the companies that you're spending time with is awesome.

Lenny (00:40:15):
Yeah. So on that, something I'm always weary of is folks jumping around between all the fancy companies to get a bunch of logos on the resume. "Oh, I worked at Snap and Facebook and Netflix," and I feel like you're just building a resume and then your life flies by, and you forget that you should enjoy the things you're doing and work on things that are fulfilling and optimized for not a great resume. And, curious your thoughts on just how often you think you should move from company to company, one to optimize for opportunities in the future, or just generally, do you recommend people try to move around or go deeper at their company? There's a bunch of questions there, but take it wherever you want to.

Lauren Ipsen (00:41:01):
Yeah, yeah. Okay. Sounds good. I think it's an interesting one because logo collecting is never something that you want to be known for, and the first thing you're taught, like entry level recruiting 101 is recognize patterns of candidates that jump from place to place and don't give opportunities a full chance. So, you're spot on. That is definitely not something you want to be known for if you're a prospect.

Lauren Ipsen (00:41:27):
There's also something to be said about staying somewhere too long though. And I will say that. I think sometimes you find people that are almost loyal to a fault, and companies have tanked and all executives have left and the writing's on the wall, and they're holding onto the fact that they were hired by a really good guy or gal and they want to make it work because they care about the human being, and I think sometimes in your career you do have to be a little bit more selfish and think about what's going to be best for you in the long haul. And so maybe that is still keeping your head down and working hard while also being thoughtful about other things that are out there and not saying hard nos to opportunities that knock on your door.

Lauren Ipsen (00:42:12):
So it's one where I would say it's an art and a science because you have to be thoughtful about taking on new things and knowing when it's worth taking a bet on yourself, but also you can't run as soon as things get hard because that is recognized, and if there's a riff or an internal dispute or a new leader brought in, and that is so quick as to make you run for the fences, that's not something that people look for because startup world is hard, tech is hard. Look at the crypto world right now. Things are incredibly volatile and difficult, and you want to be able to bring people in that are going to hang with you through the highs and lows.

Lauren Ipsen (00:42:55):
We're always looking to see where people moved the needle, especially on the product side, where their fingerprints were, what they can actually point to that they did and are proud of during their time there. And so if all that they can say that they did was onboarded and moved on, then doesn't matter where you were, but it's not going to be something that I can at least stand on to cheer you on.

Lenny (00:43:22):
I really like that. A lot of this comes down to, what impact have you made? And I was going to touch on that, and your point is, one, kind of heuristic for how long to stay at a place at the minimum is have some meaningful impact you can point to that you led. Does that sound right?

Lauren Ipsen (00:43:35):
Yeah, exactly. And have that meaningful impact be something that others can speak to. I think that's huge. If you built something within the organization that you're proud of but no one knows about it, then that's more difficult to have as your stamp of approval for what you are able to accomplish there. But if you did something that cross-functional leaders were speaking to, that your team all sings the praises of, then that is something that you can put a feather in the cap and say, "Okay, I left this place better than I found it, and that's the reason that I have decided to move forward."

Lenny (00:44:15):
And I imagine part of that is reference checks. People are going to check to see if you actually were successful.

Lauren Ipsen (00:44:20):
All the time. Yup. Whether you are exploratory, opportunistic, not looking at all, people are constantly calling each other, and the world of tech is so, so, so small, and no matter how fired up you were leaving a company or what went sideways, it is so critical that you try to leave the place better than you found it and do so as seamlessly as possible, because you want people to have nothing but positive to say. And oftentimes, that ... The thing that I always find too is if I call 10 people that were a part of the same organization as someone during a given period of time and they can't speak to anything they did, in that case, no news is not necessarily good news. You want to have an impact, you want to be able to say, "I did X, Y and Z. I'm super proud of this and the reason I moved on is because I did what I came in to accomplish."

Lenny (00:45:20):
It's a little bit innately tricky for product leaders. I imagine you run into this, that sometimes you have to upset people as a product leader to get stuff done that needs to get done and maybe they disagree and then later it's like, okay, I see what you did. Is that true? Do you deal with that or is it generally like, oh, yeah, they're the great people everyone knows, like a hundred percent of people will say they're awesome?

Lauren Ipsen (00:45:38):
It's a really good question. I think there's a way to navigate conflict without rubbing people the wrong way so that they'll say negative things. There's a way to be an impactful product leader and disagree and make change, and maybe your engineering leader and design leader and marketing leader completely disagree with the direction in which you're going, but because you have all of the data to support it and because you have gone about things in a way that feels very fact first and less emotional, it's really difficult for them to then point to why they disliked this person.

Lenny (00:46:19):
Yeah. This is interesting. So say you make those 10 calls, in your experience, the leaders you want to hire, are you finding 10 out of 10 are generally like, "Yes, this person's amazing, you should hire them"?

Lauren Ipsen (00:46:31):
There's ones that are slam dunks and no one has any negative to say. That's incredibly rare. More often you find some people like to just have something negative to say, just to have something negative to say. I also take all of my back channels with a grain of salt. Maybe the person I'm calling to back channel this person with I also haven't back channeled, right?

Lauren Ipsen (00:46:50):
So every single thing that you hear, you just take, make note of, and then move on and think more holistically about. But I think typically what I would say is the glaring nos are very obvious. People that are polarizing individuals or have done wrong within an organization or made bad calls across the board are, you can get that information typically pretty quick.

Lauren Ipsen (00:47:13):
It's the mixed ones where it's, "I think that person was decent," those are pretty tough, and you need to really find people that worked super closely with them because otherwise it's pretty difficult to say whether or not they were able to make an impact. Which again comes back to why right off the bat it's so nice to just have people that you can tap within every organization that's like an academy company or a great company and say, "Point me in the direction of the three best people." I don't want to have to go through the burden of having to try and back channel all of the maybe middle 50% or what have you.

Lenny (00:47:48):
Yeah, most people don't have that, which is a reason to hire, work with a recruiter. You come build in with all of that network.

Lauren Ipsen (00:47:55):
Totally. Totally there. Yeah.

Lenny (00:47:56):
There's a couple things I want to touch on that I wasn't planning to touch on, but reference calls. You do a lot of them, I imagine. And I'm curious, do you have any tips for how to ask questions on a reference call where you actually get useful advice where it's not just, "Yes, I like them, they're great. Hire them"?

Lauren Ipsen (00:48:11):
Especially on references, provided references, I've only had two candidates where provided references have come back negative, which that's tough. Outside of that, typically references are a standard. It is important to dig pretty deep and ask the hard questions.

Lenny (00:48:28):
What's the hard questions?

Lauren Ipsen (00:48:29):
Yeah, why would I not hire this person? What are their biggest weaknesses? And then if they give you the typical, "Oh, if they work too hard," it's like, no, tell me more. What are their actual weaknesses? What are things that we should be really cognizant of? Would you hire this person again? Would you report to this person? Would you endorse this person if you knew that your name was attached to it? Things like that I think get people thinking, and even if you just sense the slightest pause, that in itself will be enough to make you think twice. Right?

Lauren Ipsen (00:49:04):
So it's a lot of reading the room and probing harder than you think necessary, which is tough. But back channel references I think will always provide a greater source of truth than provided. It's similar to an Instagram Reel as opposed to the photos you're tagged in. That's the way I think of it. It's like this is what you want the world to see or think of you as, and then these are what your peers and your direct reports and the people around you actually say about the work that you did during this time.

Lenny (00:49:33):
Awesome. Coming back to a point you made about recruiter training 101, you learn how to find patterns and red flags in people's resume. What else is a red flag in your resume that you want to avoid/there's a rule of thumb of like, if you're at a place for less than a year, it's bad. Is that true? How do you feel about that? How do hiring managers generally feel about that?

Lauren Ipsen (00:49:53):
It definitely depends, with regards to being at a place less than a year. If that's a recurring theme, of course that's a big red flag. Even if it's happened two or three times, three definitely. If it's happened twice, it's like, "Huh, that feels off." You got to let people tell their story though and their side of things, and again, it comes back to reaching out to different people and understanding if what they're saying is true was actually the truth. And so when you have a really good pulse on what's happening in tech and whether there was a riff and the reason that person was let go was actually because they weren't prioritizing a certain part of the product or whatever, like those things, it happens. That's life, especially right now, right? If we were to X every single person that has a short stint that joined a new company over the course of the past year, that wouldn't do anyone any good.

Lauren Ipsen (00:50:44):
Another thing I've found that's pretty interesting is that people will often, because they're so afraid of that narrative, they'll often not include on their resume companies that they didn't stay for a year. And in my personal opinion, that's actually almost more of a red flag because that did happen, and you don't want to just pretend like that wasn't a decision you made in your life, and usually is handled with grace. You can speak to the reason that you decided to make a bet, the reason that you went there, and the reason that you moved on, in a way that people can typically resonate with. But I've seen executives just put that they've simply been advising for two years or something like that, when in reality they had two companies that failed.

Lauren Ipsen (00:51:33):
And the fact of the matter is, I have some CFO candidates I'm talking to right now and their past three years have been short stints because they were brought in to take a company through an IPO and then that changed, or they were brought in to enter into a SPAC and then that became less of the buzz. Right?

Lauren Ipsen (00:51:51):
So these things happen and roles change, and I think it's just allowing people to tell their story is the most important thing. So I would say red flag is, for me, just always be honest about when you started, when you left a company. If I see that someone still has present on their LinkedIn but they've been gone for two years and they kind of are acting like they're still there, that doesn't feel good. Just want people to give you the truth, the straight facts, so that you can support them and tell their story and represent them in a way that makes you feel like you have all the details.

Lenny (00:52:23):
Got it. So basically, don't lie. That makes sense. That reminds me a little bit of people kind of upgrade their titles a little bit because maybe they don't have an official title or they just want to sound a little important. How do you feel about when people do that on their resumes?

Lauren Ipsen (00:52:35):
Yeah, I don't love that. I also don't love on the resume when people, and some people do this and it's okay, but when people say silly, vague names like they'll say something along the lines of, "Whatever at Reddit," as their title or, "Master of blank at this," and it's like, okay, what were you actually doing?

Lenny (00:52:58):
But I think they do that to avoid recruiters reaching out to them.

Lauren Ipsen (00:53:00):
Exactly. As their direct target, I'm pissed. So I feel directly attacked in that regard. So that's something that throws me off, but that could definitely be a personal thing. And I think overall, for the most part, people don't have any other things that really just throw me for a loop. And the fact of the matter is, resumes we look at less and less, especially at the executive level, and it's a lot more of allowing people to tell their story, meeting in person, talking with their different people that support them, and getting kind of more of the big picture around who they are.

Lenny (00:53:33):
I want to talk about what recruiters often do wrong and what you've learned there. But before we get there, one last question: do you have any tips for a product manager in the interviewing process, how to be more successful interviewing?

Lauren Ipsen (00:53:45):
I've had this come up a few times when I've interviewed product folks that they'll speak down on their counterparts or say that the reason they weren't able to meet deadlines or push product in the right way was because of the engineering team or because of other components of the business and it wasn't them. And so I think that's never a good way to go about it. So it seems obvious, but you would be surprised how not obvious it is.

Lauren Ipsen (00:54:10):
So thinking about things more holistically, speaking honestly about your strengths and things that you want to continue to grow and improve upon, and then being able to tell your story, like practice telling your story. So often people don't do that, especially when they're not looking for jobs, and then it's not until their 10th interview that they know how to tell their story and what they did and what they impacted and why they were someone to be missed when they moved on. Those are things that you want to know how to speak to, and unless it's something you've been doing or practicing, it's less natural. That's some advice I think just off the top of the head.

Lenny (00:54:45):
Awesome. That's really good advice. One thing that makes me think about, I know I want to get to this last section, but do you think the best product leaders have their kind of story figured out in the future and work backwards from that and have a sense of where they want to end up, or just kind of take it as it goes? Because I'm the latter. I had no plan, I just went to see ... follow the path that was presented. Do you think that is generally true for folks that end up being successful, or do you recommend people think about, "Here's where I want to be in five years, here's what I need to do to get there"? Do you have any guidance there?

Lauren Ipsen (00:55:18):
I mean, for what it's worth, I'm definitely more with you. I don't know where I want to be in five years, so it's tough for me to say. But I do think that typically someone that has the end goal of being a CEO will put the pieces into place to try and get there, and so it's not a bad idea if you do have an end goal of wanting to run your own thing to inch towards that. So maybe you go from being a product specific leader to then operating in some type of GM of a business unit capacity and owning a P&L, and then although it's more of a product oriented role, you're still getting closer and closer to that end goal of COO or CEO.

Lauren Ipsen (00:55:53):
So if it's something like that, then I think that naturally makes sense. Do think people can be enticed by shiny objects, so excited because it's a step up from a title perspective and things like that, and I think that's just so not important in the grand scheme of things. You could be the VP of product or a CPO of what, you know? That's so vague. If someone just says, "I want to be a chief product officer, that's the end goal," I always say, "Of what?" You could be the chief product officer of your household. Is it of a multi-billion dollar consumer brand or ...

Lauren Ipsen (00:56:32):
So I guess what I'm trying to say is work backwards from a goal for sure, but don't allow titles or valuation bubbles or other things to derail something that feels good. If you're in a role and you feel like you're making an impact and you're learning and you're growing and are excited about the work you're doing, do not allow a title of some other company to make you feel like what you're doing isn't worthwhile.

Lenny (00:57:01):
I love that advice. So many people just chase some fancy new role, new title, new logo, and end up getting there like, "Man, this sucks."

Lauren Ipsen (00:57:08):
Exactly. Yeah.

Lenny (00:57:09):
This reminds me, I did a meditation retreat once and one of the teachings there was you don't want to be fixated with achieving a specific thing, but you want to push your cart in that direction, just like head that direction and have a general sense, but not, "I need to be that thing and that's what'll make me happy."

Lauren Ipsen (00:57:26):
Exactly. I think that's exactly right.

Lenny (00:57:27):
Awesome. Okay. Final topic is from the recruiter perspective, what do you find recruiters do wrong most often or miss when they're trying to attract great product talent to a company?

Lauren Ipsen (00:57:38):
Yeah, so this is one I feel especially passionate about because I do think recruiters have a bit of a reputation, and I think that it's for some good reason. There's naturally people that forget that these are human beings that we're dealing with every single day that have lives, have families, have careers, or ambitions outside of their career.

Lauren Ipsen (00:58:01):
So I think it's essential that you remember that this is another human being on the other end of things and that you should treat them with the same level of respect that you would expect to be treated.

Lauren Ipsen (00:58:15):
This has become even more apparent now that I have gone through some of my own recruiting cycles where I was looking for different jobs, and a transactional recruiting call just will rub you so the wrong way and will make you want to put things on your resume like I just alluded to that say things like, "Whatever at Reddit," or what have you because you just don't want to deal with it.

Lauren Ipsen (00:58:36):
And so I think you have to be a human, you have to start with a relationship, find common ground, build rapport, listen to people, like actually listen, and remember what they say. So if someone says, "I never want to do a crypto company," and I just am only shoving crypto companies down their throat, that's just insanely tone deaf. Or if they say, "I have this vest that I really want to be around for in May of next year," and I just keep hitting them up prior to that, that's just so not receptive to what they just said.

Lauren Ipsen (00:59:12):
Things like that, make notes if easier, because we speak to so many people all day long so it's definitely not easy to do. But I'll have a note on my calendar that John Kim's vest just happened in March, and then I'll be like, "Oh, okay, might be a good time for me to catch up." I won't say, "Congrats on the recent vest." I'll say, "You want to grab a coffee, or do you want to catch up about this?" Or, "Hey, I saw that you were speaking at this conference, love what you spoke about with regards to this." You got to find ways to connect with people outside of just shoving them into a job.

Lauren Ipsen (00:59:46):
And so I would say something that I've learned and become very good at is starting with a foundation of relationship building, gaining trust from people, because once you have that, then people will hear you out on jobs and people will listen to you and actually trust your advice from a career direction and perspective, but that takes time to build that, and it's definitely not going to be built by just chucking things at the wall and seeing what sticks with people and seeing where you can shove them temporarily. In fact, that will make them lose trust. And once you lose trust in a candidate, it's impossible to get it back.

Lenny (01:00:22):
It's interesting how one of the recurring themes of our chat so far is just play the long game in every way, which takes more time.

Lauren Ipsen (01:00:28):
Yes.

Lenny (01:00:28):
Kind of sucks that you have to put in all this time ahead of time before you really need to get something done, but what you keep coming back to is just that's how you end up being successful as a recruiter, as a product leader, as a hiring manager, as a founder.

Lauren Ipsen (01:00:39):
A million percent. Yeah. Yeah. And it's really easy when you've got a quota to hit and you've got people to provide for and a mortgage to just think about the numbers, but you have to play the long game because people aren't just a commodity. It's so much more.

Lenny (01:00:56):
And one of the perks of working with a recruiter is they have done that already for you, and so I was going to ask, when does it make sense for a founder to engage with a recruiter like yourself and when should they not?

Lauren Ipsen (01:01:08):
Engaging with recruiters sooner rather than later in a proactive way is always a positive thing. It's just sometimes companies aren't at the stage where they can necessarily hire a full-time recruiter because of resources and how expensive it is to bring in an exec recruiter.

Lauren Ipsen (01:01:26):
So having someone that you can bounce things off of in a more informal capacity, bringing in someone like a talent advisor that can help in a consultative way, those types of things, a million percent. Leaning into the venture firms that have backed you, which is a lot of what I'm doing right now, that is definitely areas in which early CEO founders should be leaning into that and trying to get as knowledgeable as possible. And then I would say typically series B feels ... series A, dependent on the check size, and then series B feels like a good time to bring in a couple key big players, if the company's well positioned to do so.

Lenny (01:02:06):
And bring in meaning full-time in-house recruiters or a firm?

Lauren Ipsen (01:02:09):
Probably bring in a firm. Yeah. That would be my recommendation. I think you can bring in one or two recruiters in the early days like seed, if it makes sense for the company and they're growing quickly, but it's all kind of case to case.

Lenny (01:02:22):
The fact that you're kind of off the table for most founders now that you're at GC, which is a part ... And is that true? Like you basically at this point work for General Catalyst founders, is that correct?

Lauren Ipsen (01:02:32):
I am supporting all of our GC founders in the consumer and crypto portfolio. That being said, I spend all day every single day networking and chatting with amazing entrepreneurs, people that could be founding a company down the road and need some advice, great people that want to help in an advising capacity. So it is, I would say, 50% networking, 50% actual parachuting into portfolio.

Lenny (01:03:00):
Got it. Okay.

Lauren Ipsen (01:03:01):
Supporting them.

Lenny (01:03:01):
That's cool. I didn't know that part.

Lauren Ipsen (01:03:03):
Yeah.

Lenny (01:03:03):
So outside of that, what do you suggest founders look for when they're looking for a recruiter, and the second to last question, what are signs that this is a good firm, a good recruiter? Just what should you be looking for when you're looking to hire a recruiter, either in house or a firm?

Lauren Ipsen (01:03:15):
I think it's important to provide them with some direction and then see if they can recite it back to you. Tell them the types of things you're looking for and then say, "Did that resonate? Because I'd love to hear from you what you took away from that and what you think we should be looking for."

Lauren Ipsen (01:03:32):
And then kind of off the bat, ask them for a couple candidate ideas. Don't give them time to just go call other people. In real time, ask them for some candidate ideas. Where does their brain go? Who are people they would call tomorrow on this? The more that you can get that dynamic relationship formed before you even go to search, the more you can determine whether this is someone you want to calibrate with.

Lauren Ipsen (01:03:54):
So yeah, I think just putting them on the spot a little bit and asking them to show their work rather than just sending over a deck of searches that could have been done by other partners or could have just been done by other people on their team. You want to actually understand who this person is. So that first question is testing their listening skills and their ability to actually hear what you're saying and what you're looking for, and then the second is, okay, now how quickly can we get calibrated on what this profile should look like.

Lenny (01:04:21):
Awesome. That is great advice. Very tactical. Any final words or wisdom before we get to our very exciting lightning round?

Lauren Ipsen (01:04:26):
This has been awesome, by the way. I think more generally, the advice is just treat people like human beings, build rapport, play the long game, and gain trust, and that takes time. And so those are the most important things from a recruiting standpoint, is being able to tap people and have them feel like you genuinely have their best interest at heart and that you care about their career and life outside their career. And so I think that's what makes for a really good recruiter.

Lenny (01:04:53):
Simple advice, but often forgotten and easy to overlook. Awesome. All right. We've reached our very exciting lightning round. I'm going to give you six questions, whatever comes to mind, we'll go through them real fast. Does that sound good?

Lauren Ipsen (01:05:08):
Okay. Yes. Let's do it.

Lenny (01:05:10):
Let's do it. What are two or three books that you recommend most to other people?

Lauren Ipsen (01:05:14):
The Power of Now and You Are Here.

Lenny (01:05:17):
Wow. Awesome. What are favorite other podcasts that you listen to other than this one?

Lauren Ipsen (01:05:22):
I mean, there's tech ones, but Your Own Backyard because I went to Cal Poly, so that one hits a little close to home.

Lenny (01:05:28):
Wow, I haven't heard of that. Cool. What's a recent movie or TV show that you've watched that you've enjoyed?

Lauren Ipsen (01:05:34):
Top Gun I've watched too many times and-

Lenny (01:05:39):
The new Top Gun.

Lauren Ipsen (01:05:39):
Yeah. And then TV show. Oh, it's all trash reality, so I just can't tell you.

Lenny (01:05:45):
I get that. I understand. My wife has that and she can't tell anyone. Yeah.

Lauren Ipsen (01:05:51):
That's my one secret.

Lenny (01:05:51):
All right. Okay, great. We'll move on, but that's great. What's a favorite ... Oh, this is interesting. What's a favorite interview question that you like to ask or maybe you've seen someone ask?

Lauren Ipsen (01:06:01):
I love the good strengths and weaknesses question. I think it's really good to see how people self-analyze themselves.

Lenny (01:06:06):
What do you look for in their answer that's the sign that it's well answered?

Lauren Ipsen (01:06:10):
Honesty, authenticity. Can read right through a, "Work too hard," answer or a perfectionist type answer. What are your weaknesses? Let's talk about it.

Lenny (01:06:19):
For real.

Lauren Ipsen (01:06:21):
So that one I think is always a really good test of character.

Lenny (01:06:24):
What are some favorite apps right now?

Lauren Ipsen (01:06:27):
I've been playing around on BeReal. I mean, I love Spotify, it's straightforward. And then I've been on Strava, I've been running, so that are the-

Lenny (01:06:34):
That's a good combination of apps. That's like a full life.

Lauren Ipsen (01:06:37):
Thank you. Thanks so much. Trying to be.

Lenny (01:06:41):
Final question. Who else in the industry would you say that you most respect as a leader and a thought leader influence type person?

Lauren Ipsen (01:06:49):
My first boss out of college, Joe Suliman, is awesome. He's always taught me to lead with that relationship-based approach and it's really so easy to say that you do that, but then to actually do it and live it out for the people that work for you, as well as the people that are in industry and speak of you, is something else. And so he's always taught me to do that, and I just learned a ton from him and he's just incredibly smart and in tune with what's happening in industry and makes great stances and opinions on how to navigate those types of things. So, he's someone that I have an immense amount of respect for.

Lenny (01:07:24):
Sounds like an amazing person. Lauren, this was excellent. I feel like this is going to be useful to so many people, product managers, founders, other recruiters, all kinds of other people. Thank you so much for doing this and making the time. Two final questions. Where can folks find you online if they want to reach out or maybe collaborate with you and learn more? And how can listeners be useful to you?

Lauren Ipsen (01:07:44):
Yes, absolutely. And also, thank you. This has been so much fun. They can reach out to me on LinkedIn. I happen to be on that one quite a bit, so definitely can DM me there, can send me an email, and I can shoot you that over as well. And then the way they can be helpful is if there's people that they think the world of, shoot them my way. If they have questions around best ways to go through an interview process or how to navigate different things, please, by all means, a huge part of my job is trying to help people that are going through this for the first time. Happy to just be a sounding board or of help in any capacity.

Lenny (01:08:19):
So if you're an awesome product leader, you want to see what's out there, find Lauren on LinkedIn. Is that the best place to find you?

Lauren Ipsen (01:08:24):
That's perfect.

Lenny (01:08:25):
All right. Awesome.

Lauren Ipsen (01:08:25):
Yep.

Lenny (01:08:25):
Thanks, Lauren.

Lauren Ipsen (01:08:26):
Thanks so much. Appreciate it.

Lenny (01:08:29):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.