03: Hiring generalists, building better teams, and building a startup home you want to live in

Hiring is one of the biggest determinants to your success in your business, but it's also one of the hardest things to do as a founder. To be frank it is actually a huge struggle I have in my own business, so I am excited to bring on  the perfect expert to make hiring the right team easier and more streamlined for your business.

For today's episode we have on Shaina Anderson who has spent 15 years building startups. She is the founder and CEO of Hello Generalist, the startup community's home for part-time hiring. She also works as Chief of Staff at Nory AI, as a coach to startup Chief of Staffs and as a startup angel investor. Prior, she was Chief of Staff at Yelp for Restaurants and was an executive at Choose from its seed stage through series 2 acquisition where she led marketplace supply delivery operations and US market expansion. 

In this episode we will cover:

• How to know when and who to hire for your company 
• How to know when to fire someone on your team (and should you have already?)
• The difference between a specialist and a generalist and which is best for your team. 
• Why Shaina believes windy career paths are better than straight forward career paths

To connect with Shaina Anderson:
LinkedIn
Hello Generalist
Website

Book Suggestions:
Range by David Epstein
The Third Door: Mindset for Success
Powerful by Patty McCord

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DM me on Instagram: @mywritehandwoman

Work on Your Messaging or Copy with Me: The Website

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Sign Up for the Exact Factor Sprint

Chapters

• 3:20 What is the difference between a specialist and a generalist?
• 12:49 How to know when and WHO to hire for you start up
• 17:43 Why windy career paths are better than straight career paths
• 29:52 Steps for your first hire // hiring for a role fit vs a value fit
• 37:18 Firing: When to fire and how?

Transcript

Shaina Anderson: [00:00:00] Hiring is the hardest thing ever.

Shaina Anderson: And it's one of the biggest determinants to your success as a business. and so it's this weird activity that especially first time founders or first time hiring managers are looking at and realizing for the first time, but what never stops, even if you've hired 300 people, or if you're hiring your first person is.

Shaina Anderson: What problems do I need solved? And to what extent does this hire need to solve them for me? Hi there. Welcome back to the bold founder, your go to podcast for two real convos on shaking up your success mindset, standing out with your marketing, achieving those stretchy growth goals and making bigger moves all while staying true to who you are as a founder.

Lucy Bedewi: Today is my first guest interview ever, and I'm going to be interviewing Shaina Anderson, who has spent 15 years building startups. She's the founder and CEO of Hello Generalist, the startup community's home for part time hiring, which is why we're going to be talking all day. [00:01:00] all about making the right hires, and also works as chief of staff at Nori AI, as a coach to startup chief of staffs, and as a startup angel investor.

Lucy Bedewi: Prior, she was chief of staff at Yelp for Restaurants, and before was an exec at Choose from its Seed Stage through Series 2. acquisition where she led marketplace supply delivery operations and US market expansion. And for all those people who love traveling and relocating, she lives in London now and she moved from San Francisco.

Lucy Bedewi: Let's get right into it. She has so many nuggets to bring and I know that this is going to help you so much as you continue to expand your team, expand your business and make sure that everyone who's rowing your boat is aligned with your values. So let's dig in.

Lucy Bedewi: The behind the scenes of The Bold Founder today were not very glamorous. If you guys could see me right now, I am running through a hailstorm, trying to get to a [00:02:00] co work that has somewhat stable internet because I have my first interview ever with Shaina, and my hair looks like an absolute tornado, which podcast for this exact reason, so none of you could see me.

Lucy Bedewi: But I just find it so ironic how, Messy this production is, and it's still just going to be an incredible episode. So the reason I'm saying this to you is I think it's so often to think if you're going to do something, you have to do it perfectly, but this is your reminder happening in real time right now, that life looks far from perfect and we're still showing up, we're still making it happen and we're still bringing you all the nuggets, all the value as you hire for your startup or your business.

Lucy Bedewi: So I. hope that gives a little dose of reality so you can see that if you're behind the scenes it looks messy, but your product or offer or whatever you're building looks great, great. That's all we need.

Lucy Bedewi: I am so excited to dive right into this conversation that we're going to be [00:03:00] having today about hiring, specifically hiring generalists. So instead of doing the whole, what is your life story thing that I'm sure a lot of podcasts are doing, I would love just a quick little snappy two sentences on your role in starting Hello Generalist and your mission there.

Shaina Anderson: My role in starting Hello Generalist, well, I'm the founder and CEO. We started this thing about a year and a half ago. We're now a community of a couple hundred people who are all startup pros who are looking for part time work. And we pair them with early stage startups who are looking for real depth of startup expertise, but not ready to hire full time or don't need to hire full time for that particular problem.

Shaina Anderson: And my whole mission is about making the world of work more flexible. I started this whole thing because I wanted non full time work with startups. And yet this whole industry of consultants and [00:04:00] contractors and independents, like none of it was for me. None of it spoke to me. so That's why we got into it.

Shaina Anderson: That's why we started this. 

Lucy Bedewi: I'm curious, can you talk us through what a generalist is in comparison to maybe a more traditional contractor or consultant? Quite really simply a generalist is someone whose perspective on solving problems is shaped by a wide range of experiences, usually professional experiences, and what they end up embodying is agility and creativity.

Shaina Anderson: they're known for making complex connections that their specialist peers might not be able to make. and I named this whole company after this concept because I read a book by a guy called David Epstein. he wrote a book called range, which is a weekend read. It's Excellent. No matter who you are.

Shaina Anderson: And there's great Ted talk on it that you should go look up. It's 12 minutes and it's wonderful.[00:05:00] and what David Epstein wrote about was this cultural norm that exists where people argue that if you want to develop a skill or play an instrument or be a leader in a field, You have to start really early.

Shaina Anderson: You have to focus really intensely and you have to rack up as many hours, really deliberate, intense practice as early as possible. And if you delay, or if you stray from that path, you're screwed. You're totally behind the people that have. And what his research did was he took a look at the world's true top performers from professional athletes to Nobel laureates.

Shaina Anderson: And what do you realize is that specialization is the exception. In terms of big success, not the norm. generalists, not specialists are really primed to excel in these areas that are unpredictable or that are complex or that are changing.and you know what this looks like. he writes about examples, everyone from Duke [00:06:00] Ellington to Vincent van Gogh to the inventor of binary code.

Shaina Anderson: They all came to those areas of expertise really late in life. And after exploring a bunch of other varieties of paths, right? like van Gogh famously had 30 different careers before he picked up painting as an example. and what range also talks about is the environment. that generalists really succeed.

Shaina Anderson: He talks about those environments. I'll talk about the other specialist environment first, the environments where specialists succeed, where rules and structure are set. They stay the same year over year. they're predictable. There's clear feedback. Those environments he calls kind environments, things like playing golf or playing chess.

Shaina Anderson: But then in contrast, there's these wicked environments, and it's just the opposite. They're ones that are changing all the time. not a lot of rules in place, not a lot of clear feedback loops. and that's where the [00:07:00] generalist really excels. And, if you're thinking about. Like what a wicked environment feels like, Oh my God.

Shaina Anderson: If you're a startup founder, you live it. I was about to say we're all in the wicked 

Lucy Bedewi: environment. 

Shaina Anderson: Wicked environment. Yes. Early stage startups are wicked environments and we're increasingly living in this world, which is changing all the time and totally unpredictable. So that's a lot of the research that went into me very personally realizing that, Oh my God, I'm a generalist.

Shaina Anderson: And that's an awesome thing. And also me being able to name and bring a definition to why I found such a home in leading early stage tech startups. 

Lucy Bedewi: I think so many founders are looking for that person that's almost their clone because they're out here wearing all the hats.

Lucy Bedewi: All day, and if they're surrounded by specialists and there's no one to help them solve those complex problems that might span different aspects of their company. So I'm curious, is there a feeling in a [00:08:00] founder or a stage in a startup where you would recommend, okay, it's really time for them to start looking at a generalist.

Shaina Anderson: Yeah. It's such a tough question because I don't think about this as a general versus specialist thing. I think it's like all types of people to make up a company. but what tends to be true with hiring inside of startups is that there's two, two things founders are thinking about. They're thinking about one, what's the problem I need to solve?

Shaina Anderson: And I can't solve myself or with the existing people on my team. And two, how much money do I have? Like, how much can I spend on somebody to come in and solve this problem for me? And like that equation sometimes ends in like, Oh, I can go get a tool to do this. So I'm going to buy a tool that will solve my problem, or I'm going to.

Shaina Anderson: play with a GPT and create my own, repetitive process through AI. That's going to solve my problem. But when it comes down to like, no, actually I need a human to come in [00:09:00] and solve my problem. there's all sorts of choices to be made. And I think the smartest founders I see really keep a focus on what's the problem I need to solve and what skill sets are required to solve that problem. At Hello Generalist, our customers are usually pre series B venture backed startups or small, ambitious, growing, privately owned businesses. And what they have in common is that they don't have the budget to hire someone who's worked as a COO in the startup world for 10 years. And also they typically don't need that person for 40 full hours a week.

Shaina Anderson: So there's this sweet spot that emerges where it's like, wow, I have all the problems that I might need a fractional COO or a finance advisor or a project doer in HR. But I don't have the budget. I didn't need them full time anyway. Great. Let's bring in those people to come solve that problem. 

Lucy Bedewi: Yeah, I think when it comes to [00:10:00] trying to figure out how to solve problems, it's always that chicken and the egg of budget versus needs versus okay, like, what's actually the problem because I think it's so easy to hire because you think you need to hire.

Lucy Bedewi: And Let's say someone is struggling with budget and even bringing in a generalist is a big stretch for them. how would you advise them if they were trying to navigate maybe bringing on a co-founder or someone to just be in it with them with equity versus hiring a generalist and maintaining more control over their company?

Shaina Anderson: What a question. You know, maybe we'll first, let's talk about what I mean when I say generalist inside of startups. I think that, like the easy assumed definition, we're a platform where people come to hire people to do everything for them, the unicorns, the unicorn, yeah. We're the unicorn factory and like that doesn't exist.

Shaina Anderson: And we're definitely not the company that does that. What tends to be true is that our customers come to us and they say, Shana, I have this [00:11:00] struggle where. We have a wonderful problem where we have too many leads and we don't have the internal system between sales and ops to manage the customers that are coming on and coming in.

Shaina Anderson: And I need somebody to help us build that system. And the founder looks at that as a real generalist role. I need somebody who can stretch across sales and operations and account management and help us build a system to bring in all these leads that are coming in. And what we do at Hello Generalist is we really pick apart that problem.

Shaina Anderson: And what is almost always the case is that when we scope a role out, there's a few clear skillset spikes that go into what's actually needed. Person doesn't need to be an engineer. The person doesn't need to be a finance expert. No, the person needs to have a really real depth of experience. And if you use CRM tools, they need to have familiarity with how a sales team works, how an operations team works.

Shaina Anderson: And based on the extent of the problem they want solved, there's probably a [00:12:00] seniority level. That we're looking for there too. And so generalist to us really refers to that mindset of adaptability that people have, proven and built inside these wicked early stage startup environments and founders for the most part, I've yet to come across someone who really is needing to hire somebody to do everything inside their business. the closest thing to that, we'll work with a bunch of founders who are technical. And who are looking to hire their first business person. And as we scope that role, that first business hire usually owns a mix of internal operations, some finance staff, some HR staff, and some early customer work and support.

Shaina Anderson: That's a common role, but it's still not one of these magical unicorn do everything roles. It's a known entity and the people on our platform have done that type of work several times over inside startups. They're experts. At that skill set spike, [00:13:00] right? 

Lucy Bedewi: Yeah. And I think it's so easy to get caught up in the words, like I need a fractional CMO or I need a fractional COO.

Lucy Bedewi: And I'm curious from an actionable standpoint, when these founders are trying to find that person that can supplement their skillset, do you think that they're getting. A little bit too caught up in these titles, or do you think actually those are really helpful to turn the generalist into something that's a little more tangible.

Shaina Anderson: Yeah, titles are helpful, right titles can say a lot. And I think what I hear you saying is like too often. titles get into this corporate poetry territory. I'm a strategy and operations finance leader or whatever. Nice president, yeah. Yeah, totally. Yeah. Corporate poetry. Yes. Beautiful sounding but actually means nothing.

Shaina Anderson: But titles can be really helpful, in Indicating what the job is in indicating the leveling of the person and their area of [00:14:00] responsibility. Right? and then when you, you know, you bring it to this world of fractional roles or part time roles. What we do is a startup founder comes in and they think they need a fractional CMO. Awesome. That tells me a lot right off the bat about what's on their mind and what problem they're trying to solve. And then what we do is we start every engagement with startups with this scope call where we're going to spend 30 to 45 minutes.

Shaina Anderson: Me, the founder and usually a mural board, and we're going to really pick apart what problems that fractional CMO needs to solve, what outcomes they're trying to reach with that hire. And what we do is we match those types of skills to people in our community who have done that type of work before.

Shaina Anderson: So in many ways, they're practiced and they're experts. solving those problems, but they're doing it in this truly wicked early stage environment where you need to have that adaptability like [00:15:00] you'd be. You'd be shocked to hear who considers themselves a generalist. These are 20 year startup, fractional CFOs.

Shaina Anderson: These are 20 year chief HR officers. These are startup founders who have founded three companies. They're chief of staff who have held three different chief of staff roles over time, and they all identify with this concept of being a generalist, despite their many years of depth. In that area. It's pretty cool.

Shaina Anderson: And like, to your question earlier about wow, where does this generalist thing fit in against the consultant world and the fractional world and like all this, like word soup, what is it, what does it actually mean? It was kind of the answer from my own lived experience, wanting this type of work and realizing as I looked online that all of these marketplaces are for. matching independent workers to companies. The main message that they promote is, Hey, if you are [00:16:00] a super niched down, independent contractor, we can match you with the super niched down job inside of a big company that wants a consultant. And what I need to be true is that all of my founder friends and every startup I've ever worked in.

Shaina Anderson: We're allergic to the word consultant. you need doers, people that can get in the weeds and get stuck with you and help you figure out what to do next. And so there's this whole missing gap in the market of Startups really needing people, smart people to come help them non full time.

Shaina Anderson: And then a bunch of my friends is where it started. We're in San Francisco. We no longer wanted full time jobs. We wanted to change our lives coming out of COVID and we're trying to find this new mix of independent work. So its generalist was really the. The siren that I put out, all these true experts on paper, deeply resonated with recognition.

Lucy Bedewi: It's so cool because you often will think a [00:17:00] generalist is not someone who has depth in a role or has that kind of career path. And I remember you saying when we were emailing back and forth, like windy career paths. Are actually better than straight career paths. And I would love for you to touch on why you should be looking for people who don't necessarily have that X leads to Y path.

Shaina Anderson: Yeah. I'll speak about all this research that I first read in David Epstein's book Range, and now the first hand in the workplace. So, what his book brings together and consolidates is all this research that shows the cultural narrative. Is this one of 10, 000 hours that you are only excellent at something when you early in your career have spent 10, 000 hours working on something and then you are excellent in it and then you will be successful.

Shaina Anderson: You'll make money and you'll have longevity in your career. But all of the research shows that actually the opposite is true. That people take their time finding [00:18:00] the thing they want to go deep in. Your Vincent van Gogh's, your, Duke Ellington's, your inventor of binary code, they took their time along the way they experimented with different musical instruments or areas of science and learned to adapt their brain along the way to different problem sets.

Shaina Anderson: until they finally found something that really hit them. And when you look at this graph, which is really interesting about someone's age over time, right? Age over time. and, on the X axis and on the Y axis, you can look at how quickly they specialized in something or when they found the thing they went deep in.

Shaina Anderson: What the research shows is that people that specialize. really early, they beat out the late stage specializers. They beat them out in earning money early on in their career because they found something to go really deep in early on.

Shaina Anderson: But over the lifetime, they earn [00:19:00] much less than people. That explore their way into finding their depth, they earn much less and they burn out faster, meaning though they found their specialization early on, they tend to not stick around or have sustainability in that specialization of the long haul compared to people that explore and try different areas and try different things and then find something that sustains and fuels them.

Shaina Anderson: They earn more money over their lifetime and they have more sustainability and longevity. In what they do, so by two metrics that I think are super relevant to a happy long money earning career, earning more money and more longevity in what you do. so there's the research, and then personally, like I've lived to this out.

Shaina Anderson: I'm a college dropout. I dropped out of college to help a friend open up a food truck. And it launched me into this world of entrepreneurship and taught me a lot about restaurant communities and local food [00:20:00] communities. And was this amazing education in the basics of building a business. And,Over my 20s and 30s, I've spent time traveling around the country, selling tickets to dinners around the country.

Shaina Anderson: I've spent my time in venture backed startups as an executive. I've been a founder of several companies. I now work fractionally with teams and have fellow generalists that I build. so it's super windy. and yet I think as I meet people, the perception of me now in my late thirties, since I've explored and tried these different paths, I'm viewed as an expert in what I do.

Shaina Anderson: I'm viewed as an expert in early stage startups. I'm trusted to come in and help other founders figure out what they need to do on their team. I'm trusted as a high partner to help them find great people for their team. So it's counterintuitive in many ways. I'm kind of a living example. this really windy kind of strange path along the way, but along I've found [00:21:00] the thing that I've been able to go deep in and expertise has come. So yeah. So what do you think about that? 

Lucy Bedewi: I 

Shaina Anderson: think it's great 

Lucy Bedewi: because we're always told there's this. Almost like lie narratives sold to us that saying everything has to make sense when you climb a ladder. It's a very linear path and all these things say like, if you're a multi potential light or multi passionate, you need to pull it together and pick one.

Lucy Bedewi: And so I think hearing you say that is so refreshing because especially a lot of founders, we have business ideas. on the reg. And we put them in a notebook. And of course there's something to be said about taking a period of time and focusing and going all in on an idea and growing it.

Lucy Bedewi: But we became founders because we don't want that linear path. I think that's such a great message to keep saying, especially in this world. That really glamorizes someone who did something since childhood, and then they do it for 30 years. And just what you're saying is no, the windiness [00:22:00] actually makes you stronger and all of the pursuits that you do.

Shaina Anderson: Yeah. And remember that a story like Tiger Woods is the example here. And we love the Tiger Woods story. He has played golf since he was a little kid. He grew up excelling in golf at every stage of the way, and then became Tiger Woods as we know, best golfers in the world. And, that story is so great to latch on to, it's so satisfying and it's made its way into this cultural narrative of what you have to do to find success.

Shaina Anderson: And yet all the research shows that that is so much the exception. So far from the norm and that most successful people find their way to success by scraping through different experiences and trying different things. There's a great book that I love called The Third door. It's awesome.

Shaina Anderson: It's another really quick weekend read. And the third door talks about, this idea of three doors, and three doors to get into a nightclub is an easy way to think about it. The first door is the door that everybody gets into. you [00:23:00] stand in line outside of the club. You're in line with all sorts of other people, like a hundred people in line for this really popular club.

Shaina Anderson: And you have to wait your turn. And then there's a bodyguard at the door who tells you if you can get in or not. That's the first line. The second line is the VIP entrance, where you're really rich, or you know a guy, and you just slap a hundred dollar bill in their hand and they let you in the VIP entrance.

Shaina Anderson: And then the third door is the door where you run around to the back alley. And you climb on top of the dumpster and you kick in the window that's above the dumpster that leads this way into the kitchen and you crawl through the kitchen and then you make it into the club through the backdoor dumpster kitchen window entrance.

Shaina Anderson: And like, very obviously there's a metaphor here, right? Most people think that the best way to get into the club or the success is to stand in the line to do exactly as you're told to get in line to wait one by one for your turn for someone else to tell you that you can come in. Most [00:24:00] people aren't VIPs. So like, don't have the money or don't have the connections to get it through the VIP door. So you're left with this choice of like, okay, I can accept the results that standing in the first door is lying, gets me, which is waiting and somebody else gatekeeping it. Or I can knowingly make the choice to run around to that back alley and climb on top of the dumpster and crawl my way through the kitchen.

Shaina Anderson: And when I read that book, I was just like, yes, I, oh my God, that was, that's so me. And, not surprisingly, that book tells the story of a lot of business leaders and tech founders whose literal path is the moment where they were able to find their way to that back alley and that back door.

Shaina Anderson: So it's, it's more common than you think, but we don't glorify it. And the same way that we do the go to college, be a good girl, wait in line. And then like someday someone I'll let you in. Yeah. 

Lucy Bedewi: Yeah. I mean, We absolutely glorify following that path, but [00:25:00] to do anything differently, or, using that word disrupt, of course you got to crawl in through the kitchen, at least in some elements, because what's waiting, this is definitely not the metaphor of the book, but what's waiting for you at the door is something that's already been done.

Lucy Bedewi: and you need to create that creativity and create that path. Outside, by the 

Shaina Anderson: dumpster, in the back. Yeah, totally. And like,all these metaphors aside, The Third Door, I think is an awesome metaphor, it's an awesome book, totally read it. But I don't want it to be mistaken for this other narrative of The only way to succeed is to get dirty, and be really like, climb through the dumpster in the kitchen. Like, be legal, be ethical. Please. Yeah. there's a lot of ways to live a really wonderful, meaningful life for yourself. Like for me, I did my fair share of kitchen and dumpster climbing, but I also, in coming to start Hello Generalist,woke up and realized that no, I want a project I can work on for the next 10 years if I'm [00:26:00] lucky.

Shaina Anderson: And I want it to be a profitable small business that does good work for my employees and our members and our customers and me and my family. and I'm going to go slow and I'm going to build it profitably and it has nothing to do with the narrative. of bro Twitter about 5am cold showers and that's the way you have to go to climb in through your own third door.

Shaina Anderson: no, I just woke up and posted some stuff on LinkedIn and opened a Squarespace page and worked on it slowly over time and now have a really thriving, profitable small business. just decide the kind of happy life you want to live and go make the choices you need to get there.

Lucy Bedewi: Exactly. And that's the thing is scrappy means getting a Squarespace account. Not staying up until three in the morning with bloodshot eyes, cold calling 800 people to get your vision realized. So I think that's such a great caveat. And I also want to, I want to circle [00:27:00] back speaking of corporate poetry, circle back our conversation to this point that when founders realize, they are scrappy, they are doing the things and they're, they are getting some traction too.

Lucy Bedewi: And they think, okay, I need to hire someone who is also scrappy, who has this depth of knowledge, who is able to support me in a specific area, but not a specialist. They're on the path to a generalist. let's say it's their first hire.

Lucy Bedewi: What is the first thing you would tell this founder to do on this path? 

Shaina Anderson: Get clear on what problems you want to solve. And put them in order and rank them and think deeply about them.and that's what. We started working with the founders. Hiring is the hardest thing ever.

Shaina Anderson: And it's one of the biggest determinants to your success as a business. and so it's this weird activity that especially first time founders or first time hiring managers are looking at and realizing for the first time, but what never stops, even if you've hired 300 people, or if you're hiring your first person is.

Shaina Anderson: What [00:28:00] problems do I need solved? And to what extent does this hire need to solve them for me?and at Hello Generalist, I get a laundry list of problems, because they're early stage startups and there's a bunch of problems. But we work to group them and understand the skills needed to solve them and understand how urgent they are.

Shaina Anderson: And then we pair those problems with, people that have solved them before or have seen environments like that before, where they can come in and bring their expertise to that startup.or, in many cases, you know, get a, hungry, scrappy, early career doer in the door who wants to. Maybe it's a really undefined set of growth problems.

Shaina Anderson: Great. let's get that early hungry, scrappy early career doer in the door. Put them in this area and see what they're able to do. but that's my advice. And that advice will scale through when you're a publicly traded company of 10, 000 people. I worked at Yelp for a couple of years as chief [00:29:00] of staff at Yelp restaurants.

Shaina Anderson: And we were an organization of about 300 people inside of Yelp and the same hiring practices. that I'm talking about, we used there, just like we did at choice and a VC backed company. I joined at the seed stage when there were 10 of us in the founder's apartment, trying to figure out what we were hiring for and what we were doing.

Shaina Anderson: Keep thinking about your problems. 

Lucy Bedewi: Yeah. It's so interesting because it feels so clear. It's like, obviously, you know, figure out where your problem is and then fit it in there. But I feel like so often people don't take that time to do that, or it's really easy as a founder to just be like, everything's on fire and I need everyone.

Lucy Bedewi: So exactly what you said with prioritization and. Once they figure out their problem and they decide the direction they're going to go, they're like, okay, I kind of know the generalists I need. I'm going to get someone young and scrappy, or I'm going to get someone who's done it before. Obviously experience is probably that gold standard, but what else should they be [00:30:00] looking for that most founders might overlook when they are trying to hire for this position? 

Shaina Anderson: I think about hiring at a really high level as having two components. It's role fit, and it's values fit, meaning role fit, what's the job, what problems need to get done, what skill sets do you need, at what seniority level do you need to bring to really solve these problems to the extent that I want, role fit.

Shaina Anderson: And then values fit. Values fit is hard because it requires a bunch of things. It requires a founder to have a point of view on, what values do I want this person to bring to building this brand new company that doesn't exist? What values are important to me and the colleagues that I want to work with?

Shaina Anderson: And often the early team members who will shape the future of our culture. What values do I want them to embody? and then being able to interview people and listen carefully for how those values show up. Oh, [00:31:00] that's hard. And it takes practice. and it can be really scary to do, because it requires a level of vulnerability and authenticity.

Shaina Anderson: I think the most successful founders I see have an opinion on the values that they're looking for and what values they prioritize over others. And they're listening for those and asking questions to hear about the way people think about those. And they're taking that role fit and values fit approach, whether they're hiring someone to do a project for them for a month, or whether they're hiring someone to work 20 hours a week.

Shaina Anderson: Or whether they're hiring a full time engineer, that's the core from a really high level. It's 

Lucy Bedewi: So interesting that you say the values fit is the tricky part because I completely agree. And I'm curious, can you give a tangible example of a company that would embody a specific value and then what questions would you encourage them to ask people?

Shaina Anderson: So I'm married to another founder, which is fun. [00:32:00] That'd be a fun kitchen table discussion. I feel like every night Yeah. At first when we both realized, Oh my God, we're starting companies at the same time. We were like, this is a bad word. This isn't going to end well, really stupid.

Shaina Anderson: Why are we doing this to ourselves? But actually it's been wonderful. He's building. He raised, uh, he's a venture backed company. They went through YC and Jason Horowitz backed their round. And so they're on a very different trajectory than Hello Generalist, which is a profitable independent business.

Shaina Anderson: So anyway, One of the values we talk about all the time. One of the values on his team, he looks for people, especially engineers with a really high bias for action, really high degree of ownership, big bias for action. He wants his engineer. He's a CTO. He wants his engineering team to not just be ticket takers.

Shaina Anderson: And be assigned stuff to go do. He wants people to fully, he wants his engineers to fully understand the task at hand, to work with people [00:33:00] across the company, to ruthlessly pull at it till they fully understand what they're building and not call it complete until the metric has moved that they wanted it to move.

Shaina Anderson: So to the point that it's not about shipping. It's not about taking a box and just deploying the thing you were told to do. No, it's about a full understanding of it. And then it's about chasing down the impact of what you deployed, after it's out there. So that's one of the things. So 

Lucy Bedewi: Well said I've always just said proactive and I am about to steal that because that is, I think what all of us want.

Lucy Bedewi: And that was said so beautifully. 

Shaina Anderson: Yeah, totally. We all want that, right? And I'm like, my gosh, especially in your first engineers, you really don't want them to just be taking assignments from you, the founder who, we can be honest, like as a founder trying to, I'm a non technical founder. And as I built our product, I came to my.

Shaina Anderson: Engineers with a big murky idea of what I think I want. [00:34:00] And then lots of specific weird stuff that I think needs to be in there. It's awful. And God bless Elise, our engineer. Tear it apart. Tear apart my ideas and make them actually good. Exactly. Exactly. Obsess over it. Get really clear on it. So anyway, his, his interview process is meant to, He tests for all the technical skill sets, but he's also the conversations that they're having and the tell me about a time questions that he's asking the situational behavioral questions that he's asking during these interviews are written really purposefully to pull out Stories of that type of ownership.

Shaina Anderson: And then as they're telling their story, he's asking lots of questions to try to really hear more. and he's regularly turning down really good technical engineers who are strong role fits, poor values fits. So he's holding that value, that commitment. To the team he wants [00:35:00] to see and to no surprise his team moves so fast and they're so fun to work with because they're so high ownership.

Shaina Anderson: They get really excited about the work that their name is on and it's an excellent product on the other side. another thing I'll add in here and this is like a tangent. There's a coach. whose work I've listened to over the years, he's a founder coach and he talks about this concept of as a founder, the startup is your house.

Shaina Anderson: It's your house that you own. You live here for the long run and you have employees that come and live in the house for a time, but they are guests. They're not the owners of the house in the same way you are. And that can be really tough to hear, especially as an early stage hire who has great ownership and who really makes that house a big part of their life.

Shaina Anderson: But the truth is that it's not the same as being a founder of the company. So when you think about the metaphor of someone's [00:36:00] house in their life, I live here. It's my home. It's my safe, comforting home. I think about it nonstop. I live in it constantly. It's your responsibility as a founder to build your home in a way that's sustainable for you.

Shaina Anderson: A lot of that is the people that you let into your home and you allow to stay in your home long term. And it's the hardest thing to do. but it is what will give you as a founder, the real freedom. To feel sustainability in your own company, to feel like your home is yours and that you're not a prisoner of it, which can happen as companies grow really fast or as founders fill their homes with people that are not living their values. so I think that's one that's really helped me over the years. It's ah, that's right. I need to build this as my house. This is sustainable for me. And Excellent and warm and comforting and hospitable for everybody that walks in the door, sustainable for them to come and live here too.

Shaina Anderson: But [00:37:00] ultimately the decisions of who comes in and out are mine. and my values need to be present in that 

Lucy Bedewi: It's such a good metaphor, especially because as you were saying, if you're lucky you're in that startup, you're in that business for the long haul. And I think this actually is such a good segue into a little bit of an uncomfortable conversation around firing.

Lucy Bedewi: Because it is. If you let someone into your home and you even mentioned it, who comes in and who comes out, oftentimes I think you have that intuitive pull of okay, this person needs to go, but are there any kind of tangible tips you can give around that? If you do hire someone, maybe you didn't really define your problem very well, or you didn't do that whole values, that values fit, or maybe the role just not right, or you didn't even know you could hire a generalist, whatever the reason.

Lucy Bedewi: How do you recognize in yourself that you might have made the wrong decision? 

Shaina Anderson: I'll pile on first and I'll tell you more reasons why firing is hard. Firing is hard because it is [00:38:00] rarely, if ever, you're lucky if it's really clear that you should fire somebody. it is rarely clear that somebody should go.

Shaina Anderson: And it's hard because it's easy to make excuses. Wow, this team has changed so quickly. Wow, we don't have the resources they need to really be successful. Oh, they've done such great work for us to date. I really. Want them on the team. Oh God, I don't have the muscle. So backfilling them is going to be a nightmare.

Shaina Anderson: And I'm going to have to go without an engineering leader or a sales leader for a while. it is so hard to know, but what I can tell you from my experience and what. As you talk to managers and leaders, you'll hear the same thing, which is. Never have I once fired someone too soon. The opposite is always true.

Shaina Anderson: Every time I fired somebody, it was months too late and I will work my whole professional life to build the muscle, which is an [00:39:00] internal self reflective muscle to know it is time to fire somebody and I'm going to do it now. Never have I once fired someone too soon. And the repercussions for that are felt everywhere.

Shaina Anderson: Your team feels that the rest of your team feels that the time you waste agonizing over it, that you could be bringing someone in that is much more functional. There's a great question that a COO of mine, many years ago gave me. and His question to me was Shana, knowing what you know about this person today.

Shaina Anderson: Knowing what you know about how they perform, how they show up, the work that they do, knowing what you know about them right now, would you hire them again for the job today? And nine times out of 10, I should say 10 times out of 10, every single time I'm talking to a founder and we're talking about this, we're coaching them through something.

Shaina Anderson: I get the, like the look on their face, looking back at me or like, Oh God, no, I wouldn't. No way. And yet when pressed, Grace, [00:40:00] that being so, what are you going to do? It becomes an internal game of waffle making, just waffling. Oh, it's the resources or the backfill or the waffle making a lot of waffles. and that's cause it's just so hard and painful to do. This is one of the journeys that founders will go on. You're going to face it. There's no avoiding it. And when you face it. will get to choose how you show up. Do I show up in a way that honors their work and I give them the feedback and I send them off to go find a place where they are going to be cherished and successful?

Shaina Anderson: Or do I enable them wallowing here? And bringing our company down in the meantime, go read the book, powerful by Patty McCord. She led HR at Netflix early on. She has a really extreme view on this. Netflix had a really hardcore view here, but it's really inspiring. because it is simple and makes a lot of stuff.

Shaina Anderson: It's like [00:41:00] internal agony. 

Lucy Bedewi: I'm definitely going to read that. And I really appreciate the mindset shift that you offered in terms of almost bringing it back to rejection is redirection. And the fact that yes, they're not doing so hot at your company, but if you let them go, there is going to be another role that they are better suited for.

Lucy Bedewi: And any founders listening to this. No, that you have options and people who can help you make those better hires, especially, as you backtrack and think, okay, would I have hired them again? Maybe your problems have changed. You're at a different point in your company. So it's a whole different discussion.

Lucy Bedewi: thank you for taking us through that, very, fun, actionable experience. We went from what people should do if they're kind of making that hire all the way to the end of the life cycle. If it gets there, we hope it doesn't.

Lucy Bedewi: And I would love to hear, is there anything that you would like to add to the conversation of when a founder is hiring that you feel like [00:42:00] we did not get to today? 

Shaina Anderson: I would just add an underline that there are very few rules. We live in this amazing moment to build a startup. Where you can hire people from anywhere in the world for a huge range of budgets and a huge range of scale sets. So we are very far away from the day when you needed to hire somebody full time in your town to come into your office.

Shaina Anderson: And the extent that you explore that spectrum is totally up to you. There's no one right way to do this. You don't have to pick a path that stays with you forever. You can try different things on. And that's awesome. so I just want to underline that there's no rules to this whole thing and you've got a bunch of options for you out there.

Lucy Bedewi: Yes. Go find your people wherever they live in this remote world. Yeah. You can meet them at a bar. You can meet them at the zoo. I love that. 

Lucy Bedewi: I'm going to end on a little bit of a vulnerable note. [00:43:00] One of the main reasons why I wanted to start the launch of this podcast with an episode on hiring is because I have been a weak hirer. I've been a bad manager. I have gone through periods where there was so much turnover. And I asked myself, what am I doing wrong?

Lucy Bedewi: It's so easy to think that hiring is something that maybe you're good at, or you're not good at, or it's something you should just know. But hiring is such an art. And if you are in this stage where you're thinking I'm making bad decisions and I'm not a good manager, I'm not a good hire, or if, If any of those stories are going through your head, know that they sometimes go through my head.

Lucy Bedewi: They definitely went through my head before I got help and listened to experts like Shaina. So allow yourself to forgive yourself for not making the best hiring decisions. And I really hope this episode helped ground you from a specialist. Well, ironically, a generalist helped ground you as you make [00:44:00] your next hiring decisions.

Lucy Bedewi: So thanks so much for listening and we'll see you next time.