Lenny's Podcast: Product | Career | Growth
00:18:48 · Jen Abel
[00:18:48] S1: Yes. Okay. This is the most important call out of all of them, okay? Because you are setting the tone with how they think about you, how they respect you in your role and your craft. And the information they will tell you on the first call, they will clam up moving forward because it starts to feel like a sales process. So all of the information edge you can gain as a seller is on this first call, okay? So keep it ... And this is what I like to do, super informal. Don't show them anything. Don't show them a demo. Don't show them slides. Focus on them. Have a one-on-one dialogue for 30 minutes, okay? Now again, if they're bringing in a C-suite executive, you better have your founder join that call as well. I don't know any founder that wouldn't want to be in the room with a Fortune 100 C-suite executive. So make sure you bring in your founder if you have that person on. But let's say you had the N minus one, you had the VP up. Okay, super brief, "Hey," and this is how I typically open, "Hey, I'm going to keep this super informal. I don't even know if we need a full 30 minutes." Put them on the back for like, "Oh, this person's not trying to take up my time." "All I would like to do is swap intros. And if it makes sense, we can always get on another call and go much, much deeper, but I just want to better understand who you are and I'd love to share what we are doing and why I specifically reached out to you." So I say, "Would you like to go first?" Always let them go first. Give yourself the edge, right? Because the more information you are receiving before you speak, the more you can frame it and tighten it to what they specifically care about. So-
00:20:29 · Lenny Rachitsky
[00:20:29] S0: And they also aren't sitting there now listening to a pitch.
00:20:31 · Jen Abel
[00:20:31] S1: Yeah, exactly. Now they're talking. Now they're conversing. Now it's like, "Okay, now it's fun. Now this person's not pitching me. I'm in a conversation and a dialogue." Okay, so now you're talking to them and they usually do a very brief open. They're like, "Hey," we didn't get a chance to look up the chief legal officers at SpaceX. Obviously, this is just a case, but whoever that person's name is, "I oversee the legal team and blah, blah, blah." "Okay, okay, great." They usually don't give you much. So they say, "Okay, interesting. How are you thinking about ... Do you guys have an AI mandate going on at the organization? How are you thinking about the existing way you guys are doing work? What are you looking for going into 2027? Does anything need to change?" Ask, "Does anything need to change?" Because again, what they're going to usually default to is what conversations have happened above them and have been transcended down. So the change is usually dictated from the top, which is great, "So what needs to change going into 2027 that you did in 2026 or maybe not at all?" And that's when they start to open up. And again, you don't want to be too pointed of anchoring them towards your product, because again, the more they speak, you can start to pull on the strings that matter. So they could say something along the lines of, I'm making this up at this point, but, "We are really looking to figure out how to bring more of this work in-house and rely far less on external law firms because now we have more tools and capabilities." "Okay, is there a measurement to that right now? What does that look like internally in terms of if you've done that successfully in 2027?" And then they'll say ... You're trying to understand how mature is this thought, right? Okay, so now they're going in and they say they can't really answer that fully. "Okay, why is that important now? Why not wait another year? You guys have so much going on. You just had this massive IPO. What's causing the team to want to reshape this or rework the way that they're managing internally?" And that's usually the moment of where they start to really guide you in terms of how they want to structure their team. So now you're getting all of this information about where they want to go, right? Now when you talk about what you do, now you're the vehicle to get them there, right?
00:22:59 · Jen Abel
And so I try and spend maybe 10 minutes, the back 10 minutes explaining what we do and just keep asking them questions. Be like, "Oh, that's so interesting. What an exciting role to be in." Be like, okay, full disclosure ... And by the way, I take a step back to that. Do not bring a recorder to this call. Do not record the call. They will not be open. They will not be vulnerable. They might assume it's being recorded because I think everyone operates under that assumption right now, but for the benefit of yourself, do not have a recorder present. Just be, "Off the record between the two of us talking right now of what you just shared, what really matters or what do you want to own or what's the chronological ..." Keep digging, digging deep, because the more you dig, the deeper you go, the more information they give, okay? Now you can't sit there and just pepper them with questions. This is that art piece of, "How open is this person?" Some people are poker faces, some people are not. You will be able to go much deeper with some and not deeper than others. You just have to improv, okay? But after you now have that intel and you can now understand, "Okay, here's the frame I'm going to take," now you can give them the pitch, okay? I will confirm every single conversation I have, the storyline that I tell looks slightly different. I do not have a scripted pitch or frame for any call because it feels artificial. They feel it. It feels like you're putting them into a square box. The best thing you can do is listen actively and then feel confident enough to craft the pitch around what they just shared for you.
00:24:41 · Lenny Rachitsky, Jen Abel
[00:24:41] S0: That last part seems really hard to- [00:24:44] S1: Yeah, it's very hard. [00:24:44] S0: ... adjust and make up like, "Here's what you're focusing on and here's how a product is going to solve that problem for you." So that's where that art and skill comes in. [00:24:52] S1: That's right. In enterprise sales, it's so, so hard to hire for, because the more someone is trained in sales, the less natural it feels. I know this is counterintuitive and we spoke about this on another call. The most successful salespeople are not trained salespeople. That's why founders are so good at this. They don't give themselves enough credit. What are they not good at? Probably following this process. What are they great at? Pulling out information, pulling on strings, getting people excited by vision. No one can do that better than they can. [00:25:27] S0: What percentage of the time are you just like, "Okay, this isn't actually going to help you that much"? So just what [inaudible 00:25:32] ... Okay, you're nodding, that happens. [00:25:35] S1: I would say, two to three out of every four calls, there's something real. One- [00:25:39] S0: There's something real?
00:25:39 · Lenny Rachitsky, Jen Abel
[00:25:39] S0: There's something real? [00:25:42] S1: Yeah, there's something real. One out of every four calls, I'm like, "Listen, based off of the maturity of where you guys are and where we are, it's too much of a gap. I'd love to revisit this in a year once you guys have a chance to solve for X, Y or Z." That's such a great question about the qualification. Most people are not going to be qualified, not because necessarily you're talking to the wrong person, because if you're an enterprise executive or enterprise account executive, your job is to know who to talk to, okay? And your job is also to quickly disqualify someone. And it's probably one in every four calls simply because of maturity. [00:26:22] S0: Cool. So you don't have to have this intense pressure to nail it on every call and, "Here's the pitch." Okay, awesome. What I also want to comment on is this idea of getting them to share a bunch. It may feel tricky, like you're tricking them to sharing all this, but really they have problems they want to solve and you're there to help them solve a problem. And so why would they not want to just like, "Okay, here's what we need help with. Here's the problem. Here's our priority"? [00:26:48] S1: Their job is to buy solutions to these problems, right? That's why they have budgets, right? So that's why the fastest way to commoditize yourself is to go into some sales script like, "Budget authority need timing." That should be in the back of your brain. You never actually ask those questions.