The 90-Day Hiring Question Every Sales Leader Should Ask with Jason Forget

0:09Welcome to the Revenue Builders podcast, hosted by John McMahon and John Kaplan, brought to you by Force Management. In this segment, we sit down with Jason Forge, President and CRO of Cockroach Labs, whose career spans finance, rev ops, sales leadership, and scaling high-growth revenue organizations. The conversation explores a hiring mistake many leaders make, focusing on whether a candidate can do the job without understanding whether they truly want the realities that come with it. Jason shares the interview question he uses to uncover long-term fit, why energy matters more than credentials in certain roles, and how helping candidates honestly assess themselves can prevent costly hiring mistakes.

0:46For leaders responsible for building high-performing teams, this is a practical lesson in hiring for fit, adaptability, and sustained success. Let's dive in.

1:24It's a different type of grind, but it's a grind. I think it's exponentially more disappointment in the earlier days. Let's talk to traits that they have in the early days versus once you start to get 50 people, 100 people. Well, the traits is they're more transactional. They'll end up doing more deals. There's less of these big deal cycles because you're just trying to knock down those early wins. We always tended to look for people that, you know, if someone came from a home that had a family business, really liked those people. People did sports in college or military, just like people that just, you know, grinded it out and just had to continue to react and be tactical and find those things.

2:10As we grew over. They're resourceful, right? Very resourceful. round like i remember i was on the board of this company and i thought this one guy that wanted to be a cro put him in the cro job and called me and said you know they don't have like expense reports here like yeah make an expense report yeah i mean later and he said you know they don't even have a laptop i said okay so get online and buy a fucking laptop like i realized like within a week he was just absolutely the wrong person even though he did really well in a mid-sized company he was just awful when he came to a startup yeah no you have to be you have to scrounge yeah you gotta you gotta put all those things together you're not gonna get a silver platter of all these things you know um i had something here on this yeah yeah the big part for me is identifying what's required in the like you guys are talking about, but then having, this is why I feel we just miss it too many times.

3:17We're not honest about whether or not somebody has the energy to do that. And it has nothing to do with age. It has nothing to do with intellect. It is like, will that give you energy? So a lot of times I'll say to somebody, hey, I like this person and oh, can they do this? I look at the job profile. They can do this. They can do that. They can do this. I say, yeah, okay, I got it. and they're giving you evidence. Is that what they want to do? And I feel like people miss that. They get the check in the box saying, yeah, they've done it. They were at this company. They did this. They did this. They did this.

3:49And I just feel like how that's evolved for me now. And I didn't ask that too much back in the day. When I ask it all the time now, I'm like, does that give them energy? Will it make them feel like less than 1 % of the population in the world who wakes up in the morning and says, I'm doing exactly what I'm supposed to be doing. Do you ask them why they want to do it? Yeah. Well, I do something similar and I did it more with reps and I do it more with when I hire leaders now and I ask them a question and I ask it relative to whatever the cycle of the company is, if it's a rep in an early stage or if it's a manager now, but the context is the same.

4:26The question is, first I'll say, I don't want an answer to this question. I'm going to ask you a question. You need to reflect on it. And you really got to think about it. But the question is, you're going to tell me all the things why you want this job and why you're excited and what it entails and what it's going to do. And you're a salesperson. You're going to tell me exactly what I want to hear because you know yourself. That's the best product you know how to sell is yourself. But think through 90 days from now. Are we going to have a conversation because we're disappointed because you can't deliver on the expectations of the role because it will come.

4:59We're not just having this discussion on what the requirements are on the role in this time, but the conversation will come in 90 days. So let's anticipate whether we're going to have a good conversation or a bad conversation because we weren't honest with ourselves in terms of what the expectation of the job. I used to do that a lot more in the early days. I would absolutely speak to every rep. It gets harder as we get bigger, but I certainly have this conversation with every leader that we hire because I make sure I speak to every sales leader we hire. Is that that question? Don't, like I would always say, don't tell me you like updating salesforce.com.

5:36You're lying. That's bullshit. But you're going to do it, right? Like, because in 90 days, I'm not coming with my broom to clean up your business because we can predict that that's going to be a problem. So don't answer the question, but like assess if this is really for you. And that was always a good filter, like with reps in the early days. Like, hey, it's going to be chaos. Yeah, you're going to be an SDR. Yeah, you're going to go to the show. You're going to stand and reinvent for 12 hours and lose your voice in that damn dry conference center. Like, yeah, that's what we're going to do. Don't tell me in 90 days that it's not for you.

6:13Like, because that's the job. I'm doing it. You're going to have to do it. That's it. So I sometimes like, and I've had people bow out. They're like, yeah, you know what? That was a good question and thought about it. And you're right. I'm better off at a 10 ,000 person company. And I like to have all these people helping me with these accounts because that's the other end of the spectrum. Like that's the other end of the spectrum. People just can't survive. And then it works both ways. Some people thrive in chaos and they're great at it. You know, it's that's they get energy out of like scrambling and running around and doing those things.

6:47And that's fine. Like, you know, there's different types of people for different types of stages. but letting them like answer the question for themselves. Like it tends to work because otherwise they're going to tell me what I want. They want the job they're trying to sell. A lot of times they don't know. Like, so I'll ask them, okay, so you're talking to me on this real startup and I'll say, okay, so what other companies are you looking at? Well, I'm looking at Salesforce. I'm looking at service now and I'm looking at IBM. I go, what are you doing talking to me? It doesn't make any sense. You don't know what you want yet.

7:17You're talking to those companies and me. you have no idea what you what you want yeah the answer is i want the options well yes but that's not the reason like it's a reason but you're you're just setting yourself up a disappointment in the early days talk about some of the leadership and for the leaders that you're going to hire what are some of the traits you're looking for in the leaders in in the early days yeah i think um excellent excellent you know folks that can deal with ever-changing environment. As we talked about earlier, like you may be pitching a certain product market fit or use like whatever it is.

7:57And you have to be adapt and a spot like if that's not resonating and kind of be the conduit back into the business in the early days. Because feet on the street, you're hearing it, you're testing it, like you got to have a good sense of all of that so that you can take that back and share what's not working because it's early and you don't get it all figured out especially in the first couple million bucks like yeah you get some customers but what i say there is like in the early days the sales people are part sales people part product manager yep 100 i'm ready to be part product manager for a raw startup it's probably not the right job for you because the product's not going to do everything it says it's going to do or is intended to do or eventually will do.

8:48So you have to sell around that at the same time, getting really honest feedback from the customer and giving that to development. 100%. And I think that's a very early stage skill. I think guys that have been at the other side of scaling you've you you have processes and ways to you got product marketing product management teams and a lot of other insights that you can glean those things and you're trying to innovate forward based on customer feedback so that becomes less of a need then but that that's one of those things is that ability to be that is gold it's it's in the interest of the business you know i just had a conversation with a guy the other day um and he was telling me what he hated about his job.

9:33And it was that the product doesn't work yet. And I went back to my notes when I was talking to him and I said, Hey, are you sure? It's like, yeah, I've been, I've done startup. I'm a startup person. And this is where three months later I said, I didn't ask you if you've done that. I said, you obviously have done that and you did it well. Is that what you want to do now. And the reason why he didn't want to stay in this company was the freaking product doesn't work. But the company and the customers don't think the product doesn't work. That person's frustrated because they picked a company that didn't have right comp plans that were going to acknowledge that fact that we're going to have to get feedback from customers.

10:19So you've got to participate in your own rescue. You can't tell yourself, I've done it before, I can do it again. there's a lot of things in my life I've done before. Damn, I don't want to do that again.

10:57You