Office Hours Ep #6: When To Hire

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  • Show Introduction [00:10]
  • How do you think about hiring proactively versus reactively? [00:27]
  • What do you do when they're ready to make the move, but maybe you don't need that person right now, but you know you will in the next six to 12 months? [01:53]
  • How do you keep these prospects warm? [2:46]
  • What happens when you're desperate for people? How much are you willing to cut corners? [4:53]
  • Do you still use that same hiring methodology in your previous company or do you do it differently now? [8:32]
  • Did you train your people personally or you just put them through some sort of training? [8:55]
  • Don't you still have that risk of them piecing out once they get to the threshold? [13:59]
  • How do you identify potential candidates even though they don't have experience? [15:28]
  • How has your hiring methodology impacted the quality of candidates? [16:50]
  • Would you hire one of those product leads externally or would you only promote internally?[19:06]
  • How do you decide who’s going to move up? [20:47]

When To Hire

Kyle: Okay, Greg, the next question that just came in is talking about when you should be hiring versus, you know, I think a lot of folks oftentimes wait until they're underwater before they make a hire versus being proactive and actually hiring a person before they need them fully. What's your thought on that? Especially because he'd grown an operations team by a hundred people in about a year or so.

How do you think about hiring proactively versus reactively?

Greg: Yeah, I mean as much as possible. Hire proactively. I mean I've worked the easy answer. I think like more specifically be realistic with how long it takes to hire. Especially if you're a first time manager or you haven't done that much hiring, it's going to take a very long time. By the time you get the approval from your finance team, figure out how much you're allowed to offer them. Figure out like what the role is, get the job description, give it to your recruiting team, or post it online, start to do phone screens, start to bring people in and go through the offer process.

Like it's a two to three-month process from the time you're like I need help at best. And, so like really what the best thing to do is to always have people on the back burner. So when I was at KeepTruckin, I probably spend a fair amount of time getting drinks and coffee with people just to kind of keep them kind of warm. So I would interview someone or it would just like, I would meet them at like an event where I would meet people through my network and I would just like see him like every, every month or two. There was one person where I got coffee with her probably five or six times and a year after the first coffee she was like, okay, like now I'm ready to leave. And we hired her.

Kyle: Interesting. So your idea is to essentially have all of these candidates in the hopper that are kind of always ready so that when they raise their hand, you're essentially ready to bring them in.

What do you do when they're ready to make the move, but maybe you don't need that person right now, but you know you will in the next six to 12 months?

Greg: So, in that case I would either, if I really liked them, I will find a way to bring them on. So if that means going to finance and being like, hey, we can bring someone on now where we can bring the four months when we planned it. But if we bring them on now we don't have to use recruiting resources. We don't have to use a recruiting agency. They can just start. I've also done it where I use one of my open headcount. I was like, hey, I'm going to turn this headcount into this role and then turn the role that I was going to hire for in a couple months. I'm going to use that switch. This basically switch roles and before you just ask for more headcounts.

How do you keep these prospects warm?

Kyle: Cause I think that it's smart doing coffees and just keeping relationships going. But let's say they're kind of ready to move forward. How do you turn them down because you may find that yeah, they're pretty good, they're a person that I'm interested in but I know I want them in about a year but I don't need them now. How do you keep pushing that off? Cause like if I was at KeepTruckin I'd probably get a little frustrated with this company that kept talking to me but wasn't ready to get married.

Greg: Yeah. So I think you just have to make it about them and about their careers. So when the types of conversations I would have with those people are like, look, realistically I want you in like nine months. And here's why that should be a good thing for you. I can hire you now, but I'm probably going to hire you at this level. But in the next six months, if you can learn these skills, I can just uplevel you. I can give you an extra 10 grand. You can go from a senior analyst to a manager, you know, you can get an extra thousand and 2000 shares.

And so I think the key there is it's not I'm on one side and they're on the other side. It's we're both on the same side. We're trying to get to the same location, you know? And as long as you communicate it as like a same team type thing, in my experience it goes very well.

Kyle: I like that idea of saying that I'm holding off on hiring you because I want to get you more, but you've got to do these things in the meantime. And that's a good way of testing their seriousness, their work ethic, their ability to work independently. Like you get a lot of information by kind of doing that with folks. Right?

Greg: Yeah. I mean I remember very vividly a conversation I have with someone where I was like, your interview is great. You're clearly very smart. People really liked you. Here's the problem. You do not have a big win under your belt. You do not have a single story of a huge initiative that everyone cared about that the CEO personally was like, you did a great job. And you need to get that win. So I really think you should spend the next six months getting that win so that, and like obviously next time, when you're ready, we're not gonna make you phone screen. They come in once just to meet the people again.

What happens when you're desperate for people? How much are you willing to cut corners?

Kyle: Will you kind of reduce your requirements to bring someone in because oftentimes you've got this acute need that needs to be solved. You've got someone that's got 80% of the skills you need. If you bring them in, you may be able to train that last 20% are you in the mind of no, we're going to hold off until we find exactly the right person or will you cut corners?

Greg: Sometimes I will cut corners on experience. I will not cut corners on culture, intelligence, and drive.

Kyle: Smart. You give people the chance to learn more, but you'll never take a douche and turn and hope that they'll become a good person.

Greg: Yeah. Here's a good example. We were trying to hire someone for a deal and we were like interviewing people with like deal with experience and they all kind of stuck. I knew this girl who I had worked with at a previous company and she was the office manager and she's like super driven. She's super smart. She has no experience at all on this. But like she think could do it, and I've got a ton of pushback from HR. Like, yeah, you really just can't do this. Like she's an office manager. She has no relevant experience, blah, blah, blah. And I was like, do you know what? I'm going to get dinner. I'm going to see we should talk to her. And just like be honest, here are the hesitations people have about you. Like I'm being told I can't hire you. Like I can really fight for it. But like, you know, I want to know what your thoughts are and I'm talking to her and I'm explaining this and she's like, Greg, I totally understand. That makes sense. I promise you I will be the best hire you've ever made.

Kyle: Wow.

Greg: And I was like, Oh, this is so easy.

Kyle: I've had that story, but it's gone the opposite direction where someone's like, I'm going to work so hard, I'm going to get this done. And it's like, I mean there are certain roles where yes, that can work. There are certain roles where it's like, like right now if you're hiring a director of sales ops and they've not been in sales ops, that's like a critical skill. Like if you want someone to speak Arabic and they don't speak Arabic, you can't just like flip that switch. There are certain things you can't really cave on in terms of skill, but something where you think a person could be trained. That's where you're willing to cut that corner necessarily on the skills.

Greg: Yeah. So definitely if it's an IC role, I'd like don't care much about the skills. Cause like even in sales ops, when I interview people with five years themselves have experienced, oftentimes they don't know much. So like I don't really care too much about the sales ops experience they have because they're going to end up like learning different stuff anyway. So you're right, like if it's a leadership position, I think there's less, you're less forgiving around the experience. But what I will say is I am less forgiving if they are great people managers am more forgiving if they're great people managers meaning I'm hiring you as a director of sales ops and you haven't really liked cut territories before or you haven't design comm plans or your not sure like how progress folders work. But like people love working for you. And so like one question I ask when I interview for leadership roles is how many people do you manage at your current role? How many of them followed you from a previous company? And like sometimes people like, I manage 10 people. Nine of them came from my last company. I'm like, great. Like I want you all day long.

Kyle: When you were at KeepTruckin, you had a lot of resources in terms of money, you had a lot of resources in terms of training. In your current company you have fewer resources. How do you think about that now? Because you don't have a ton of cash to burn on a person who can't add value on day one cause you're living hand to mouth in terms of that's how bootstrap businesses work. How do you think about that now because your hiring practice has gotta be somewhat different?

Do you still use that same hiring methodology in your previous company or do you do it differently now?

Greg: It's actually more extreme at our company. So, we're now at, we extended an offer today so we're going to be five people in the US and then 65 people in the Philippines. And for the five people in the US none of them had tech experience before they worked here.

Kyle: Did you train your people personally or you just put them through some sort of training?

Greg: Yeah, I trained the first ones I trained Angela who runs our consulting practice and then she has been training the others. And here's the logic behind that. When you hire someone there is a time cost involved. If I hire someone who doesn't know what they're doing, it has no experience, there's going to be a huge time cost upfront. But if I hire somebody like Kyle Morris who knows a lot, there's going to be a huge time cost on the backend because that person's not going want to work for me for five years.

So I would prefer to pay that cost upfront so what our model is we're going to consistently hire people that don't have a lot of experience. That probably if it wasn't for us, like the person could not get jobs in tech but they're smart and they're hungry and like they're going to be loyal and we're going to get them for three or four years instead of 12-18 months.

Kyle: That's a fair point because the cost of turnover is so high. You bring someone on if you whether you train them or not, the opportunity costs of having to spend six months finding another candidate. If you don't have a bunch of irons in the fire, like you do, getting them up to speed and then have them transition out again is tens or hundreds of thousands of dollars to your business continuity to customers. It's a major drain. So is your thought of that having continuity or like loyalty because you've trained them and gave them a shot that's, that's kind of what you're favoring.

Greg: Yeah, exactly. I would much rather. Andrew and I had this conversation like a year ago and I was like, look, like we can essentially have like one of two strategies we can adopt. I don't care which one it is, but we need to do that for everyone. I was like, we can either consistently pay like market or above market, get really good people and just be okay with them every 12 to 18 months they're gonna leave because as soon as you get in and start consulting with the company, they're going to be like, hey, can we just bring you in Dallas? Yeah. Like, which side are you? Like how much would it be to hire you? So and we just have to accept that eventually it's gonna happen or we can do what we're doing now and we would probably pay like a lot less because they don't have the skills. So we would get like up financial discount. We would have to spend a lot more time training but we would probably get like a three to four-year life cycle for them.

Kyle: So I do have a different perspective on this and I'm really, we're in a growth inflection point. In my business right now and we're bringing on multiple people in different roles and I'm really thinking a lot about the type of person we want because we're in the situation of do we look for junior people and develop them or do we hire really senior people above market rates and, and hope that they stick around. And I think your point is really well received about like they're going to transition every 12 to 18. You gotta deal with that. I guess my hope is that if I can build a business where they don't want to transition in 12 to 18 that money is not the primary driver. Maybe I can make the same thing happen and I mean the vision I have for what I want my company to be is you've heard of like the 10 out of 10 engineer or 10 out of 10 sales rep. What do they look like? What does a 10 out of 10 operations person look like? They're through the roof in terms of their capacity. You may be paying two or 300 K a year. In my mind, you'll get double or triple than a person that you've got to start from scratch and develop just because this person will have seen so many more, they'll have more at bats on day one than person who you're bringing in and they may never see some of those edge cases and so my thought is if I can hire 10 people at 300K a year, am I in a better position than 30 people at a 100K a year?

That just happens to have developed because you can move faster. Right? It's like a a team of Delta Force guys. Like they're the best people on earth at operating. Let's make them the best people from my team and you know, execute. That's what I have in mind. What's your thought on that idea?

Greg: I mean I think that's totally valid. I think it is a function of where you want to spend your time. So for Angela and myself, we're not great operations people, like we were not the kind of people that get a ton of enjoyment from problem-solving and putting together process was like we are people people like we really like to manage and develop. So this really works for us because I would much rather be in a one-on-one than in a strategy session.

Kyle: Oh interesting. That's so different. Cause my mind is, let me come up with the vision and the operations and figure out how we build it together more than I want to sit down and like spend hours teach you about process builders and when you use apex versus flows. And that's interesting that our biases are totally impacting how we're going to hire. I guess it's not that surprising but you're going to bias towards training cause that's what you feel most comfortable doing. I feel more comfortable building a system. Like the way I think of it or I've been thinking about it is let's imagine I get a bunch of spinning plates. I just show this person how to spin that plate really well or they already know how to do it. I didn't realize that was your bias towards training people. That's what you like doing more.

Greg: Yeah. And I think even to your point, it's also the other reason why even if I didn't have that bias, I think I might still do this cause it's like so much less risky.

Kyle: In terms of class, yeah. Cause you don't have that big fixed cost of paying someone 20K a month or 10K a month to keep them around because you're step was very junior and you're going to get them up to that point.

Don't you still have that risk of them piecing out once they get to the threshold?

Kyle: Because the people that we're hiring are in very high demand and if you get someone to the threshold where you're paying them 80K they may be able to get 130 somewhere else.

Greg: Yeah. I think for sure. I think the reason why that does not worry me is I think in general when you hire people that don't have a lot of experience, you engender a lot of loyalty. But I think also the personality types that we tend to go for are people that prefer consulting. They prefer to solve one problem at 10 different companies and like get a ton of experience versus 10 problems at one company.

Greg: Because it's like it is really hard if you're somebody who just works from, it goes from company to company. It is almost impossible to have as much experience as someone who consults.

Kyle: Absolutely. That's such a big selling point to people that are interested in being developed is saying that you are going to see more problems in a year then you could see in 10 years at one company.

Greg: Yeah. And so that's the problem is or that's kind of why I'm not as worried because the people on our team know like, hey man, like maybe I could get an extra 20, 30, 40 grand if I just joined this company. But if this is not my forever company or if I don't think I can spend three or four years here and this is just another series A company then a year from now I'm going to be stagnated. And the reason they think that is because most of the people we work with are somewhat stagnated compared to the knowledge of our team.

How do you identify potential candidates even though they don't have experience?

Kyle: So if you're looking for people that maybe don't have experiences, a sales operations person, how do you even identify them as a potential candidate? You just put the job req out there and when they apply you actually talked to everybody cause it feels like there's so much, so much noise. Like I put a job posting on AngelList where no one's even reading the job description. Because I say make sure you include this in your cover letter. And no one even writes cover letters and certainly is not including that. So like it's just random people applying for a job. Like how do you actually identify those people?

Greg: We don't really do those job posting. We've done it in the past and just gotten like tons of bad candidates. So the way that we do is basically just kind of from our network. So the people that work of the four other employees that we have five of their employees that we have now. Like one of them, I went to elementary school with, two of them I went to high school with, one of them used to work with me at KeepTruckin, and one of them is the wife of a friend of mine.

Kyle: Okay. So your network is really the critical. It's word of mouth is how you're identifying people.

Greg: Yeah. And because I know that that's what I want to do and because I don't trust these job sites, I'd place a lot of effort into spending time with people. And my mindset when I meet new people is like, oh, I wonder like what your story is. I wonder if like we can work together someday. I always think that when I first meet people.

How has your hiring methodology impacted the quality of candidates?

Kyle: Because you've got to have a lot of conversations where you're like, this isn't going to work. Or do you just see every conversation as how can I make this work?

Greg: Yeah, it's more like how can I make this work? So there's a lot of times when someone's like, hey, like I really want to work for Clarus. I cannot tell you the number of times someone had said they want to get into sales ops and they want to work for me. And I tell them like-- great, go take the Salesforce Trailhead course and send me your results and like I have never heard back from them.

Kyle: I guess we're coming at this with different expectations. Like the folks that I hire, I guess I expect that on day one they should be able to add value and in your mind on day one, you should begin to train them to add value.

Greg: Yeah. So like in my mind it's like the way I'm thinking about it is like at the beginning of month two, you should be able to do simple shit on your own. After six months you should be able to start to own client relationships. But we structure our company like a product managers team. So the people on our team that are really experienced, they're basically product managers. They're meeting with clients. They're taking their needs and writing up requirements. And then our newer people that don't know the business side or don't have the client basic skills yet, but know how to like build workflows and process builders and you do data loads. They're the ones that actually doing, they're the "engineers" doing the actual work.

Kyle: They're all doing everything behind the scenes in sandbox. So if they make a mistake, it's really not the end of the world. Cause that should get caught by your product leads.

Greg: Correct. And like everyone knows if like hey, you're going to start out as a Salesforce admin, you're going to be doing everything behind the scenes and as you get more experienced, you know, maybe eventually at the three month mark, we'll take you on a call with us and you'll be responsible for writing up the product requirements from this and that.

Kyle: So our structure is not this similar where we have, we call it a project manager, but kind of the same thing where they're interfacing with the customer pulling requirements, writing up in passing to the admin dev team. But would you cut corners too?

Would you hire one of those product leads externally or would you only promote internally?

Greg: I would definitely hire externally.

Kyle: Would you hire a person without experience to be able to do that or is that something, a situation where, I can't really cut that corner.

Greg: So if they don't have any experience, I would probably not hire them into that. I would start them as an admin. And depending on the type of experience they have, I would just move them up faster.

Kyle: I see. Cause you said before an IC role, you're not so concerned about individual contributors and their skill set because they're working behind the scenes. But one of those project or product leads that's not quite an IC, that's kind of like a management role in your mind.

Greg: Correct. So like I got a guy, I know a guy right now who used to manage an SDR team and has also done great stuff and he wants to do consulting. And so in terms of like talking to clients and the MG relationships, he's amazing. He just doesn't know anything about Salesforce. So, in that case, I could just start them out in that, my kind of product role. But if I were hiring, I think what I would probably do is make it him an admin for just a month or two so he can like learn some of it and then move them on.

Kyle: I mean we're getting into specific consulting problems. I guess it's different when you're internal at a company with five operations people that's different than the problems we're talking about are very specific to it. But you know, if you were back at KeepTruckin and a person wanted one of those product leads, you would bring them in as an IC, test them out for a little while, kind of get the basics going and then move them up. What if a person had been there longer and you know, maybe has more skills and we'll use Salesforce as an example. Would you bring this person in and then say, look, there's someone that's actually more talented than you in Salesforce, so we're going to move them up.

How do you decide who’s going to move up?

Kyle: You get a lot of individual contributors and it wasn't just one person wanted to move up. They probably all wanted to. So how do you prioritize who's going to make it? Cause you're bringing people in with this idea of we're going to fast track you, but there are other people involved as well.

Greg: Yeah. So I think in general, the attitude that I have and the attitude that I kind of preach to my team is we do not want people that are worried about which slice of the pie they get. We want people that are worried about growing the pie so instead of saying like, how do I become manager, let's just figure out how we can be so successful that we need two managers.

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