Episode 790 | From Scrappy to Scalable: Evolving Your Role as a Founder

Rob Walling:
It’s another episode of Startups For the Rest Of Us, I’m Rob Walling, and this week I talked to Yaniv Bernstein, who has been both a founder and an executive at companies ranging from small startups up to very large orgs, including 10 years at Google. He’s been a VP of engineering, he’s been a COO, he’s been a consultant and he was a software engineering leader at Google and these days he’s been giving advice to founders that want to go from startup to scale up. He’s seen a lot of companies fail, as many of us do as they try to get past that 1 million, 5 million, 10 million a RR phase. And one of the big drags on a company as it grows is when a founder isn’t able to make that transition from being the CEO of a 10 20 person company up into the 50, a hundred, 200 person company. 

And that’s what we focus on today as we talk about going from scrappy to scalable, what it looks like to evolve your role as a founder, as your company gets bigger. And speaking of growing your company, I run a premium coaching program called the SaaS Institute. SaaS Institute is a private coaching community designed for B2B and B2C SaaS founders doing a million in a RR or more. There’s one-on-one coaching. There are masterminds and there is an amazing online community that will be meeting in person. The idea is to get you the systems and the support you need to scale from a million or more up into the 10, 15 and 20 million marks. We have some incredible coaches, including Jordan Gaul, Taylor Hendrickson and Mark Thomas, and our first group is very small, and that’s amazing because you get a lot of one-on-one attention. In addition, you get to chat with me and get my best advice, SaaS institute.com. We’d love to have you. And with that, let’s dive into my conversation with Yanev Janni Bernstein. Thanks for joining me on Startups For the Rest Of Us.  

Yaniv Bernstein :
Thanks, Robin. Really excited to be on.  

Rob Walling:
Yeah, it’s been a long time coming. I was on your podcast that you co-host called the Startup Podcast, creatively named. I was on that a couple years ago and I think we’re talking about recording another episode soon so folks can go check out. Certainly go check out that episode if they want to hear us. We talked a lot about bootstrapping versus raising funding. I think  

Yaniv Bernstein :
That’s the one.  

Rob Walling:
And you have been a founder, you’ve been a COO, you’ve been, I believe, a VP of engineering. You have been a coach, advisor and investor of a lot of startups, so you have quite the gamut of experience. Did I miss anything?  

Yaniv Bernstein :
Yeah, well, the first 10 years of my career, I was a software engineer at Google, so I started off at Big Tech and I think over the course of career, I’ve been going smaller and smaller earlier and earlier stage to the point now where I’m now the co-founder and chief technology officer of a very early stage company called Violet. So I think one thing that has helped me to do Rob, which maybe we’ll touch on this episode is because I’ve come from later stages to earlier and earlier stages, I kind of know what comes next. So when I’m an early stage founder, I know what it looks like to start to scale and then reach that really large stage as well.  

Rob Walling:
Yeah, and that’s what we’re going to talk about today, right, is the role of a founder slash CEO and how that changes and it changes fondly as you go from listeners will hear Noah this phrase, you build a product, then you build a business, then you build a company, and probably even beyond that, then you do all kinds of stuff, but the role of that founder has to change, and this is where we see folks like myself where my last SaaS app got to 10 people and doing millions in revenue, and I was like, this isn’t very fun. 

I just didn’t enjoy that phase. And so I had the decision of, oh, so do I raise funding and kind of hire a COO? Do I replace myself? And we were growing fast, but a lot relied on me. Do I sell? I had all these options of like, well, it’s not fun, and how long am I going to keep doing this? Then there are other folks who make that great transition and really enjoy, I think managing teams of 30, 40, 50 people. I just talked to Braden Dennis, who’s the founder of fiscal ai, and it was just him and three co-founders, and now they raised a $10 million series A. They thought they were going to bootstrap and they just raised $10 million series A and they’re at 40 people now and they’re going to scale up. So you don’t know what’s coming down the pipe except you kind of do, because as you said, you have seen these later stage and you’ve coached and advised founders in these stages.  

Yaniv Bernstein :
Yeah, that’s right. And Rob, you said it’s completely true. The role completely changes, so you’re still the founder and CEO or whatever it is, but the role is a completely different thing and you realize that, and you also had the maturities to say, that’s not for me. Both of those things are actually quite rare. I think the two biggest issues I see with people is firstly, they don’t recognize that the role has changed. They think that what got them here, we’ll get them there, that they can keep doing the job the way they did it when it was just them and a co-founder or just them solopreneur it and they actually become a liability to their business. Or another common thing is they recognize that things have to change, but they dunno how to let go. You said, okay, I’m going to sell my business. 

A lot of people are like, well, I hate this, but I’m going to keep doing it anyway. And of course the whole company feels that as well. So yeah, one comparison I like to make is I love how you say you build the product, then you build the business. We sometimes say you build the thing which is a product, and then you build the thing that builds the thing. But actually for those who are parents listening here, I think it’s actually a lot like having a kid except Rob, that you can’t sell your kid, but when you have a newborn, you are their parent. You have one job when they are five years old, 10 years old, 1530, your job is completely different. If you wipe your 15 year old’s butt, you’re not going to have a good time. And so you have to realize that even though your title hasn’t changed, parent, your role has fundamentally altered nearly reversed. You’re doing something completely different from what you were doing at the beginning  

Rob Walling:
And in your mental model of this, I’d love to pick this apart and find out how you think about it. You’ve seen more later stage stuff than I have. I see a lot of early stage stuff, up to 10, 20 employees, and I see a handful that get into the 30 40, but that’s usually like, oh man, they’re going to have a big exit or they’re far beyond where I’m at. But I’m curious if there are some particular stages that you have been brought in to advise or coach or consult that you see it’s like, oh, it’s usually at X revenue or X employees, and then there’s not just one. There has to be kind one at 10 to 15 and one at 30 to 50 pm or something. What’s your mental model of all that?  

Yaniv Bernstein :
Yeah, I mean, the funny thing is this never changes. The first time I realized that this is a problem, that the founder role changes, it was actually my early time at Google. I joined Google in 2006, so that was early-ish, but not very early. We already had 5,000 employees or something, and the founders, Larry and Serge, who are some of the smartest people on the planet, they used to run the company by basically walking into a room asking the team what they did, put it on a whiteboard, and then they would use their superior knowledge and intelligence and context to give really great advice, and you would take their advice and walk away. By the time I was there, we had hundreds of teams, and they would do that once every six months. They had 15 minutes. They’d come in, you tell ’em what you’re up to, they didn’t really understand it, they would give you some bad advice. 

And then when that happened to me, I was straight out of college and I asked, what do we do with this bad advice that we just got? And my tech lead said, oh, ignore it. I thought ignore the founder of one of the most successful companies in tech because those guys had not kept up with the scaling of their organization, they hadn’t adapted their role. So it’s recurring. But yes, I think the first time it happens is probably when you go past five or 10 people where you’re not able to just be all round the table, everyone knows everything that’s going on. You start to build some structure into things, and if you build structure into things, Rob, as you know, without actually being thoughtful about it, you end up with silos. You end up with different parts of the organization. I guess maybe that’s the way of thinking about it, around 10 people. You are now an organization. You can’t just have 10 people in every meeting, in every discussion on every Slack channel. You need to start differentiating it. So you’re organizing your team and organization maybe sounds like something that applies to a very large company, but no, I think it starts at 10  

Rob Walling:
And I want to keep going with that and find out what the next one is. But I want to touch on a couple things first. So many of us Bootstrappers folks who listen to this show left big organizations because they’re political or they’re to work for. And so I know when I went out to start my company, I was like, either I’m going to be totally solo or I’m not going to have any of the craft, the mission, vision, values, the process, what makes it all bad? And then it took me years to realize, oh no, it’s actually, it was working with people who were unmotivated and bad hires and I couldn’t pick who I wanted to. And if I actually hire amazing people, we do need a little bit of mission, vision, values, not too much, but as long as we’re living up to it, like I say, my mission, the mission of this podcast mission at TinySeed MicroConf is to multiply the world’s population of independent self-sustaining startups. 

So we have a mission and that’s what we do. And all of it does it in different ways. Some of it’s given away for free and some of it is giving people money and investing. But I had to come around to that realization of, oh, don’t throw, I threw the baby out with the bathwater. And I think a lot of people do. The other thing is eagle zoning. He’s the founder of Balsamic, did a talk at MicroConf that I think just went live on the YouTube channel, microcomp.com/youtube. Folks want to check that out. And he talked a lot about how he made the mistake of he didn’t want any process and he wanted a completely flat organization. And that lasted until about, I don’t know, 20, 25 people, and he said it was just catastrophic and he was trying to reinvent stuff and he’s like, oh no, there is prior art here, folks 50. There are decades if not centuries of prior art around how to do this. Well, maybe not within a startup per se, but at least how to organize larger numbers of people.  

Yaniv Bernstein :
I think the common problem is not enough structure and process, which is a funny thing to say, right? But if you think about it, there are two pathways that have found has gone through either like you say, they’ve worked at a really big company, they see all the process and all the croft and the mission vision values on the wall that everyone ignores and everything like that. And they say, that’s crap. The problem is all of the process. I’m going to have something without process, which is a misdiagnosis or they’ve never been at a big company and they’ve just never seen process or structure before, so they don’t know what they’re missing. And so you end up with organizations that are under scaffolded, and I made this mistake as well, but what you need is the right amount of process or maybe we call it minimum viable process, that it should be something that’s there to support you, not to strangle you. 

And I think people often give this negative view of it, which is it’s bureaucracy, it’s red tape, it gets in the way. No, it’s there to support you. And if you think about, I’m a software engineer for those who are more technically minded, if you think about building a large code base, you don’t just write the same sort of spaghetti code that you would if you were just building a throwaway script. No, you have tests, you have architecture. Maybe once you’ve reach more than a few people, you document it, right? You’re not doing that to make your life harder. You’re doing it to make your code base maintainable and to maintain a certain level of velocity as you go forward. And I’ve always taken that software engineering way of thinking and I’m like, okay, if you’ve got a system of people, you’re building a system of code, now you’re building a system of people, how do you architect it? How do you actually think about making sure it works efficiently and is robust and maintainable?  

Rob Walling:
Have you read anything or seen any type of resource that talks about this? We are going to get back to your next phase. We got to 10 employees. I want to hear the next one, but have you done any writing on it or talking or seen? Is there a book? Is there something we recommend that kind of talks more in depth? Because you and I will just touch on these things of like, oh, at 10 we should, you said introduce more process. And I’m imagining someone listening to that and being like, what does that mean?  

Yaniv Bernstein :
Well, it’s funny, actually, I have a blog or newsletter that is dormant, I haven’t written in it for years, but it’s called People Engineering precisely for the reason I mentioned. It’s a software engineering approach to running systems of people. So there are a number of articles in there. I wrote that when I first became A COO, which really is about, I think when done right is you are the chief architect of the organization. So yeah, like I said, I haven’t been on it for years, but if you subscribe, you never know, I might start writing in it again. Otherwise, please take a look and it might provide some useful pointers.  

Rob Walling:
You have an archive there. It’s at newsletter dot people, ENG, like people engineering.com, and there’s an archive link in the top of, I’m presuming all your awesome. Let’s talk about the next phase. So someone’s at 10 employees and they’re putting in a little bit of process, just a little bit. I used to tell people this just in time process, I don’t want to ratchet up too much. Where’s the next phase that you see folks stumbling?  

Yaniv Bernstein :
I think the next phase probably around 50. It really does depend on a few factors anyway, between 30 and a hundred, let’s say. But I’d put the mode at 50, right? Where you are now doing more than one thing at a time. You have multiple teams that are each operating autonomously, maybe not quite independently, but that’s the point, right? You can’t just say again, look at some of the bigger teams. You’ve got your engineering team or you’ve got your sales team. You can’t just say, oh, everyone in engineering is just doing one thing or everyone in sales. So maybe that’s one way of thinking about it, Rob, when you get to 10, you can’t just have everyone in every meeting. You might start to say, well, not every engineer attends the meetings. You start to get maybe a bit of a functional breakdown by the time you get to 50, you’re having cross-functional teams, let’s say, right? 

You’ve got the team that’s doing your market. Sorry, I know you don’t like marketplaces for boots, traffic. I was going to say marketplace. You’ve got a team that’s doing your mid-market and a team that’s doing enterprise or whatever it is, and they’ve got different roadmaps, they’ve got different processes. And if you’re not careful, then things really start spinning apart there. On the sales team, you might also divide things up by market size or you might say, oh, look, we’ve got our customer success teams and our BDRs and SDRs and all of that. You’re putting more of that structure in. And so I think every time you are in a situation where you upgrade the complexity of your structure because it’s important you’re changing your architecture, you then need to change your way of working to match that,  

Rob Walling:
Not only your way of working, but really your way of thinking, right? It’s like your role is your job title stays the same, but your role completely transitions. Do you have a thinking? When I think about going from zero to 10 employees as let’s say a single founder, and let’s say the founder maybe is a developer who it’s SaaS and they built the product, so they run product, they probably manage the engineers. Usually they have something to do with marketing, although they don’t want to and they had to hire all the people and they’re kind of getting stuff in. So they’re just right now still a utility player and they’re probably managing everyone, or they maybe have one manager. But let’s say you’re at, what is it? What should it look like at 30 people or 50 people? Let’s just pick a number somewhere in there. 

I have 30 employees, 50 employees, and I’m still that founder, CEO, but the org is there and it’s healthy because it could easily be I’m the founder and this is a big flat org, and everyone’s still reports to me a little bit like the Larry and Sergey story you told earlier, which is, well, that sounds like a catastrophe. So what’s a better way to maybe structure the org and to think about what things might we want in place? We probably need some mission vision values. We probably need an HR handbook, probably need some other stuff that I’d love to give folks an idea about.  

Yaniv Bernstein :
I think that there are a couple of things to this, so maybe one way of thinking about it, and again, this is very much similar to having a young baby. At first, you are the person doing everything. You are writing the code, you’re doing the sales calls, everything like that. You’re basically solo. Then up to about 10 people, like you said, everyone reports to you. You are still the person who knows everything, who can hold the complete context of the business in your head, who everyone reports to directly. And so you can be quite directive. Maybe you’re not actually writing every line of code, maybe you’re not taking every call yourself, but you tell people what to do and what you tell them is good is right. It’s a better decision than they could make themselves a lot of the time because you have that superior context and both at the high level, but also all the way down to the granular details at 50, that’s no longer possible. 

You can’t have 50 people reporting to you directly, so you don’t know all the people as well as other folks in the company. You cannot know every granular detail of what’s happening in your company. And it’s funny, and maybe this is, when I say it’s between 30 to 150 people, there are a number of things that affect that number, but one of them is how capable the founder is of just holding vast amounts of context in their head. And it’s one of those classic cases of a strength turning into a liability or into a weakness, which is the more you can hold in your head, the further you can go before it all starts crashing down around you. Maybe you can hold a hundred folks worth of context in your head because you’re very clever and very hardworking, but every person hits their limit, right? 

Larry and Sergei, maybe they could handle a thousand person org, but they couldn’t handle 3000. And so there is that as well. And so you’ve got these increasing levels of indirection, and perhaps to a certain extent it does follow reporting structures as well. First, you’re writing the code, then you’re managing the people who write the code, and then once you get to 50, you need another layer of management in between. And like you said, every person who has had that idea of, oh, I don’t need managers. We can have a flat structure learns that they were wrong. It might seem that, again, management gets a bad name from big companies where you’ve got pointy head bosses just wasting space. But good management is essential to a growing organization. And so then you’ve basically, as a founder, you’ve got an exec team. I know Rob, before the call, we were talking about this and you said, well, bootstrappers don’t necessarily like that term executive, but I actually, I want to bring it up anyway because I think that’s another limiting thought, right? 

Because what you’re saying is, as a founder, not only I’m now acting through my leaders and that team is my team, they are executing, that’s what they call it, executives. And you are there to run that team. So first you’re writing the code, then you’re managing the people who are writing the code. Now you have a team who manages the people who write the code or do the sales calls or whatever it is. And that’s why you talk about mission, vision, values and process and so on. You’re not in every room. You don’t have all the context. So as a founder, you still want to be in control. You still want the company to grow and evolve the way that you want it to. And so now you need to say, how can I make sure that the decisions that are made, the conversations that are happening are the ones that I would want to happen even when I’m not in the room? 

Because there are a whole lot of meetings, there are a whole lot of rooms that you are no longer in because you can’t be everywhere at once. And so you’re actually talking about scaling yourself as a leader. And I think when you think of it that way, it seems a lot more appealing than saying, oh, we’ve got a bunch of processes and standards and mission, vision values. It’s saying, this is how I get to be in the room even when I’m not in the room. And that is actually the work that you start doing as a founder.  

Rob Walling:
That is a really good point. And it’s something that I encountered at, well, I guess it was a little bit after selling Drip where I started managing managers, but even more with TinySeed as I’ve promoted folks who become managers, and the thing that I’ve struggled with is I learned how to manage and I feel like I’m a good leader. I’m not phenomenal, but I paint the vision. I get us in a direction nuts in bolts wise of a lot of things I don’t, are not my favorite, but I know how I manage and I know how I think about managing. So then when I promoted someone on our team to become a manager, and they said, okay, how do you think about management? Help me think about this. What should I read? What resources? And I was like, oh, I’ve never trained someone, not never, but I have not trained anyone recently in becoming a manager. 

And I had to then think about what was my process and how do I actually think about this? You can kind of be natural at something and if it works good, but you may not know really what makes you good. What are you doing right and what are you doing poorly? Usually you have blind spots if you’re not examining it. And so that was a big realization for me of like, oh yeah, if I’m not deliberate about this, it’s going to be a mess if I’m not deliberate about making sure that the people that get on the bus are the right ones, but also that the managers are really dialed in and doing this well, suddenly it felt like I was losing control of things because there are folks now in Microcom, TinySeed who don’t report to me, and I only see them every six months at an event. And that’s, we’re not even a huge team. We’re 10 people. But that realization alone that you just set of you’re kind, I think you said duplicating yourself or replicating yourself, that blew my, that’s a tough one. It’s a tough one, and I think it blows a lot of people mind. Do you want to talk more about that? How can one think about doing that? Well,  

Yaniv Bernstein :
Yeah, I mean absolutely. And it starts with that realization that you are highly, highly dependent on your managers. 

Again, I’ll use that child analogy. When you have a baby, you basically own them what you want them to do. That’s what they do, except for crying. As they get older, as they become teenagers, Rob, well, you’re no longer in control, but you can only influence. You can create rules and guardrails and set values and so on because you are no longer their complete dictator. And it’s the same with the company. So you have this team and you can say, yeah, it’s my company. You’re a bootstrapper. Maybe you in a hundred percent of it, but just because you in a hundred percent of it does not mean you’re in 100% control because you have got people and people have their own needs and their own ways of thinking and their own levels of autonomy. And so when you have managers, yes, you need to train them well to be managers, but you also need to keep them very close. 

They’re your eyes, your ears, they’re also your arms and legs. You work through your managers. One of the things I’ve seen, it’s a very common mistake, and it can be so hard. This is part of the letting go, is if I’ve got a team that is reporting to a manager who is reporting to me, and I want that team to do something, it can be so tempting just to talk to someone on that team and say, Hey, could you please do that for me? But then this is the example of this is a teenager, that person’s going to go do it. That manager’s going to feel that you’ve undermined them in their role managing that team. They’re going to be pissed off. They’re going to come to you. The team’s going to get confused. So again, how do you get things done when you don’t get to just tell people what to do anymore? 

It’s AI time at the moment. Everyone’s talking about context, which is great because I think it actually helps you realize how important it is. You only get good responses from AI if you give them the right context. It is the same with people. So your managers and your teams more broadly, you need to give them the right context in order again to make those decisions that you would make if you were in the room. And so that’s when it comes down to all of these big company concepts, Rob, that get a bad name because they’re done poorly at big companies or whatever. You can call it context or internal communications or whatever your job is to say, this is what you need to know in order to make the right decisions. And that is both principles, right? That’s when you talk about the mission, vision, values, this is what we’re trying to achieve, this is how we achieve it, this is what matters to us. 

This is what good looks like to us as a company. It is also certain process things and there’s context. You start to be a person whose job it is to make sure everyone in the business knows what they need to know about the business in order to make good decisions. If they make bad decisions because they don’t have the right context that’s on you. And so that’s the hardest thing. And like you said, I actually think a lot of founders don’t like it. To your point, you sold Drip because you realize you didn’t like it, but a lot of founders aren’t able to let go. And then at least as well, you have to realize your job is now context setting process or structure creation. Let’s say. If you’re actually doing the thing itself, then you become a liability to your own company. And that’s a very painful realization, I think, for a lot of folks, but it’s just the reality of it.  

Rob Walling:
Yeah, that makes sense. I did want to add, by the way that we sold Drip part of it, I was unhappy with the fact that I was managing 10 people. I would’ve kept doing it. The other part is that we had a bunch of inbound interest and then we got an offer that we couldn’t refuse, so that helped grease the wheels, so to speak.  

Yaniv Bernstein :
Of course,  

Rob Walling:
It wasn’t just like, oh, I don’t want to manage the 11th person. I’m going to sell this thing. It is more to it than that. Okay, so context. How do we communicate that to people? Is it status meetings? Is it an orientation of this admission, vision, values, principles, this how I make, this is how we make decisions, this is how we operate, this is how we treat our customers, and then it’s keeping them in the loop with weekly meetings or biweekly. What is that? How do you get that into, especially your managers? How do you get that into their system?  

Yaniv Bernstein :
Well, I think this is how I personally say this is how you can still keep it fresh and feel that sense of control is you get to choose, right? This is a design exercise where you say, okay, and again, come back to that people engineering thing. There is more than one way to get this done. What is a way that you as a founder resonate with, are you good at all hands meetings or are you good at writing emails, or are you good at having one-on-one conversations? That’s up to you. The end result is everyone in your organization needs to understand the ground rules, the protocols for making decisions and for getting things done, what matters and what’s happening in the company that affects them, that affects their ability to make the right choices. I talk a lot about decisions because ultimately every bit of work that you do is a series of smaller and bigger decisions. 

It’s fractal all the way down to what do I name this variable or how do I talk about my company? But it comes down to you need to tell them, otherwise they’ll figure it out for themselves, and what they figure out for themselves may not be what you want them to. I like an all hands meeting, but other people might like writing. I’ve seen leaders who even from quite an early stage communicate effectively to their teams with a weekly newsletter, and that’s great. That scales really well as the company grows. But actually, I think the biggest one, Rob, and my favorite book in this whole area is Five Dysfunctions of A Team by Patrick Lencioni. It’s quite a famous book, and what it is actually about is it’s about managing managers ultimately, and that the point that they make is as a leader, the managers who report to you, they are your team and you are their team. 

So if I’m the head of customer success and you ask me as the head of customer success, who is your team? It’s tempting to say, oh, my team is the customer success team. All the people who report to me, no, your first team is the leadership team that you’re a part of. You are running the company together. And so you need to be thinking, okay, that’s as a leader, that is your vessel for pushing context. That’s your main control mechanism is we’ve got a team and it makes it a lot less lonely and not quite the main topic of this episode, being a founder is really lonely. Being a CEO is really lonely, but if you realize you have a team, so when you have a problem, you don’t say, what do I do? We say, what do we do? How do we solve this problem? As a team? It makes it so much less lonely, but it also means you’re able to push your message, your context, so much more effectively across everybody in your, let’s say, your 50 person organization because all of your leaders are on the same page because they’re part of one team.  

Rob Walling:
I like that. The other thing that we haven’t touched on, but I think should be completely obvious, but it might not be is it’s not just the things that you’ve said. It’s that you have to be really careful about hiring the right people because no amount of context or no amount of everything we just said will save you if you hire someone who is a manager or is bad with people or is too scared to ever disagree with the boss and is hiding. There’s all these types of real kind of weaknesses, I will say, or issues that someone can bring that you can’t get around just by being, again, just by being the perfect boss and the perfect communicator and the perfect founder.  

Yaniv Bernstein :
Yeah, strong agree. I think one of the lessons in humility, again, going back to a parent, being a parent, is you don’t get to dictate how your kid turns out. If you hire somebody, you have limited control. Even if you’re the best manager in the world, you have a limited ability to influence how effective that person is at their job. So I think this is not about saying you shouldn’t do absolutely everything you can as a manager, as a leader to help a person, but ultimately it’s up to them. It’s about who they are and what they can do. And so yes, hiring well and firing well, which is the unfortunate part of the job, but also a really important one, and you don’t ever have to love it or even stop hating letting people go, but I hesitate to think that it’s possible to do a really great job of running a company without letting people go sometimes. 

So hire carefully. And for me, that’s really about, there are two things for me. I’m being interested in your thoughts on hiring. One is starting with formulating the role. The way I think about it is people are very, again, this is a bad habit that they do learn from big companies. It’s like, let’s write 15 bullet points on five years of experience with this or that technology or doing that, and I’m like, no, okay, let’s start with the problem we’re trying to solve. Same as the startup itself. What is the shape of the hole in my organization that I’m trying to fill or in my team? And then reverse engineer that too. This is the type of person who is the right shape for that hole. And so I think if you do it that way, you have a much better shot at actually attracting the sort of people that you’re looking for, but also evaluating them accurately rather than against their accomplishments or particular skills. 

It’s like what is the shape of the whole? Are they the right person for that? And then the other thing is no matter how good your interview process is or your decision making processes, I’ve learned the humility to realize that there’s still a lot of noise. There’s a lot of error around that. So you need to think what is the way to get to defer the decision as long as possible, which means can you have that person on a contract for a while, do a trial. If you’re in a country where you can have at will employment or probation periods, make sure you actually structure that in. You won’t know for sure if someone’s really great until three or six months of working together, and so how do you get to that point that you have that if you can’t do that, then you are going to end up carrying people who are not right for your team.  

Rob Walling:
It’s an important point to drive home is most people wait. Almost everybody waits too long to fire and making a decision of who to bring on your team based on a cover letter and 2, 3, 1 hour interviews, but it’s kind of how we do it, but it’s tough. You’re not going to be right all the time.  

Yaniv Bernstein :
Yeah, I think that’s the point. I used to obsess over the perfect interview process. What is the ideal interview process? And again, I still think it’s important, but I also recognize the limitations of any set of three one hour interviews. By the way, actually, one thing that is valuable is reference checking again, which I think nearly everybody gets wrong. Either people don’t bother checking references or they do these kind of bland milk toast sort of reference checks where everyone just says, oh, yeah, I worked with him and she was great, or whatever, and you don’t actually get to know anything about them. I treat reference calls as an interview. I’m basically interviewing the person on behalf of the other one, right? I’m like, tell me about them. What are their strengths? What are their weaknesses? That can actually give you a big leg up, but like I said, there is no process. There’s no perfect process. Like you said, people always wait too long to let people go. You know what I’ve never heard in my career is I regret letting that person go. You know what I hear all the time is we should have done it sooner. And so by the time you’re wondering whether you should let that person go, my advice is you’ve probably already waited too long,  

Rob Walling:
And it’s tough because nobody likes to do it, and it’s not fun. Nobody likes to do it  

Yaniv Bernstein :
Unless you’re a psychopath. But this is not the podcast for psychopaths, right?  

Rob Walling:
No, it’s not. There’s a few of those in the startup space, but not  

Yaniv Bernstein :
Here. Yeah, that’s right.  

Rob Walling:
Well, Jan, I get the feeling we could talk for hours about this topic, but we are at time. Your name is Yanev Bernstein. Folks can find you on LinkedIn as well as since they’re listening to this podcast, of course they might like your podcast. It’s called The Startup Podcast, and they can find it wherever greater podcasts are served,  

Yaniv Bernstein :
And on YouTube as well  

Rob Walling:
And on YouTube. There it is. Yeah. Thanks for joining me today.  

Yaniv Bernstein :
Alright, thanks so much, Rob. I really enjoyed the chat.  

Rob Walling:
Thanks again to Janna for joining me on the show. It’s been great having you this week and every week. This is Rob Walling signing off from episode 790.