Episode 38: Founder-led Sales Mistake #2
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[00:00:00] 

Alex Allain: Welcome to Decoding Sales, a podcast where an engineer, that's me, Alex, and a salesperson. 

Peter Ahn: That's me, Peter. 

Alex Allain: Talk about the art and science of sales as it relates to life and business. In this episode, we're going to talk about founder led sales mistakes.

Mistake number two, not disqualifying bad fit leads. Peter, I'm really excited for this topic because this is, I think, as you put it, one of the most important things people can get wrong. So tell me a little bit, , when you're talking about this, what are the kinds of situations you're thinking about?

Peter Ahn: Yeah, I think there's a few situations. One is founders who are trying to chase the shiny logo and get enamored by that without realizing that maybe the pain point isn't a good fit or your solution doesn't quite address what they're looking for. , I think that's really dangerous because. No matter how notable the logo is, if they're going to suck up a lot of time and ultimately not [00:01:00] procure your platform, that's going to eat into your resources.

And you don't have a lot of that as a startup, right? And then I would say the other side of this is even if the company is not big or notable, even if you're not dealing with like a Nike or Home Depot, you can also waste a lot of time with smaller companies too, right? Because you have this thought that, , your product is a fit when it's not.

So I think it's just really important when you have limited resources and that's. A lot more of an acute pain point when you're a startup to ensure you're working with people who have a high chance of closing and that align with your way of thinking about the world. 

Alex Allain: , that makes sense. That's great.

So for those two examples, , what are the signs that you're , in a deal process with someone that you should be getting out of?

Peter Ahn: Yeah, I think there's a few signs. One is, , you know, we talk about this in the pitch deck episode as like the pitch deck being a qualification tool versus a pitch deck.

And so, When you're asking questions or asking somebody [00:02:00] to agree or disagree with how you see a certain solution being implemented in their company, if a lot of the answers are disagreement, disagreement, no, we don't agree with that, or that's not a problem, or I don't think this is the right way to approach it.

That's probably a deal you should get out of because you're not going to convince that person or the set of stakeholders to change their view of the world, right? You should be a technology vendor that can fit into their vision, not go against it. So I think, I think that's one example of how this plays out.

Another example is, you know, if we talk about kind of having milestone calendars or timelines or check ins, you know, if, if somebody is saying to you, yup, this timeline makes sense in terms of another demo and then, you know, getting into the procurement process and they continuously miss those milestones that you set up mutually, then that's also probably another deal.

You shouldn't just continue to try and work. You should have a moment where you say, should we just eject out of this so that both our teams are saving [00:03:00] time, , and, and when we're not eating up each other's resources. So those are just a couple of examples of how I see this play out. 

Alex Allain: I like that.

I mean, I think that's really helpful to. You know, sort of these queues that maybe you and the other organization aren't fully aligned., I gotta imagine that in the moment though, you're not going to say, you're not going to get one no and be like, it's time for us to eject. And probably if you got like literally everything was a no, maybe , the other person just wouldn't be continuing to engage.

It's probably some gray area or middle ground here, right? Where you're not really sure. I, I imagine that's like where this gets hard. There's maybe like a gut instinct that something's off to like really making that call. Like, how do you get crisp on when it's time?

Peter Ahn: Yeah. I think the way you get crisp on, on this is to call out very plainly and transparently, like a lowest common denominator of something you're both going to work towards, right? So I'll give you an example of this. Let's say a prospect is like, I don't agree with this, or I think I'm a little bit skeptical around trying to approach it this way.[00:04:00] 

What I would say in the conversation is like, completely understand this is a new way of thinking about things, which is why we're a unique product, but can we at least align that this is a problem that you absolutely need to address in the next month? Right? Or can we at least align on the fact that the old way of doing things just doesn't work?

So I think those types of statements, I think, really help to create clarity when you're trying to figure out, okay, there's a lot of things stacked against me. There are a couple things stacked in my favor. Let me just call out the fact that that's happening and see if there's at least a lowest common denominator of agreement that can help push this forward.

Another thing I think that is helpful, right? If you're very convinced that you can help the company because of The things that they're saying and it's just a mindset issue that your prospect is having. , this is where you can use things like your product to really help catalyze a deal and say, listen, like we think proof is really in the pudding.

So can we at least try the product for two weeks? Because I'm very convinced we can help you. And if [00:05:00] after those two weeks, we don't get to a good, , state of you feeling like this is the right approach, then at that point, let's say no. So I think that's where the gray area comes into play. You're right.

It's not just like a moment. It's a progression of things that you need to work through in terms of, , stacking the chips in your favor and then figuring out, , which elements are important and not. 

Alex Allain: That's super helpful. I, I really like The first thing you said there when you're talking about, um, can we at least agree,, I feel like there's a, can we at least catchphrase here.

Yes, definitely. If you, if you sort of can't get to the can we at least and get a yes on that, then that's sort of like a good eject moment. And if you're getting no's, Then you're like, let me implement the, can we at least agree protocol to see if it's time to leave? Yeah.

I, I really like that. , 

Peter Ahn: yeah. I'm glad you like that. I think a lot of it is in like phraseology and how you execute the phrasing. 

Alex Allain: Mm-Hmm, . Well, and, and I seems to me that part of that is also getting to the kind of the heart of the [00:06:00] issue, , because you're trying to like distill it down to its essential essence.

Like can we at least agree that the current model is broken?

Peter Ahn: Yes, exactly. It's a good way to kind of diffuse friction too, right? Um, if there's a bunch of things you're not agreeing on and it helps you to kind of slow the deal down, slow the conversation down and start from like first principles almost and to kind of rebuild your narrative as well because clearly the way that you've Built up the narrative isn't working for this prospect.

So you need to try and figure out a way to reframe. Mm-Hmm, . So that's also another phrase that, , I like to use is like, let me reframe it. Or what if we think about it this way? Because then, , you know, you can change up the communication patterns and really figure out is it a positioning or is it really like that they don't agree with your way of the world?

Alex Allain: Yeah, I really like that. I, something you said, just to go back briefly to that, like, first principles and then rebuild the pitch. I thought that was really interesting.

It really, it's kind of like, if you can't agree on some foundational common ground, [00:07:00] you know that , your foundation doesn't work. You're not going to build a house on top of that. So like, don't even try. 

Peter Ahn: It's a great analogy too. 

Alex Allain: Yeah, exactly. I really like that.

And I guess the other part that I like about that is, , it really highlights the importance of knowing as a salesperson, , your space really well so that you can actually do that rather than just having your pre canned pitch.

Peter Ahn: Yeah, you're right. You're right. You have to show that you're very cerebral and dynamic and how you present things and that you know the lingo too, right?

, and especially in security sales, which I was doing at Twingate. I had to be able to draw parallels to different security platforms to different competitors to different resources that you're protecting. I had to understand the difference between an SSH server and a SaaS app which you know is very obvious to like an engineer.

But Business people are like, well, aren't they all just applications, right? Aren't they all just like, yeah, yeah. And they're all like coming from servers somewhere, right? Like, like, wait a second, AWS, isn't the same thing as GCP, you know? Like, so, so [00:08:00] understanding kind of like the nuances and the lingo, right.

It's definitely very important because it allows you to. Figure out how to go back to the fundamentals if the complexity of the conversation is taking you off the path of aligning with a good fit prospect. 

Alex Allain: Which is a huge advantage if you're a technical founder doing the sale. 

Peter Ahn: Exactly, yeah, because you know the space already, hopefully.

Alex Allain: Exactly, oh boy, if you don't, problems. Yeah, yeah. So, so the other, the other thing you said, I wanted to dive in a little bit more on that one too because I thought it was interesting. This idea of like, if you're really convinced that it's a. If they are going to have their eyes open when they see the proof of concept or the demo, that feels like advice that could easily be misinterpreted.

Um, and somebody could kind of lunge toward that as a solution when they're getting pushback. But you're like, I know they're going to get it once they see it. Even if you're getting all these no's. So I want to like unpack that maybe a little bit more. Like, what are the cues that make you go, this is actually a winning move versus I'm going to burn two weeks of [00:09:00] my team's time supporting a dead on arrival POC?

Peter Ahn: Yeah, I love that you brought that up because, , I think it has a lot to do with multi stakeholder sales actually. So, , you know, let's say you have five people in a room and all five people are like, I don't think this is going to work for me. , then in that case, I probably wouldn't say, let's just try the product because there's inertia, you know, it's like five on one or two where it doesn't work.

It's probably going to be a very, very like arduous uphill battle. I think where this works, where you're like, let's just try it is in multi stakeholder sales, where, you know, that there's detractors and proponents and you feel like you want to take a bet on the proponent really shining through once they try the product.

So I'll give a very tangible example at Twingate, you know, we would often have security folks who are curmudgeony, who are like, Oh, like we need everything in the product, otherwise we're not going to procure it. But I knew with experience and like with the soundbites that I had with Previous customers that if you're a security engineer, if you're a DevOps lead, or if you're an IT manager, you heavily favor [00:10:00] Twingate over anything else.

And you're willing to forego some of the gaps that we had in terms of a full suite of security platform type of thing. So in that situation, I might, you know, take my chances on trying to like lend an olive branch to those proponents, even in the face of the detractor trying to be a gatekeeper. And so that's a moment where I might be like, Hey, can we just try this and get this in front of your team?

Because. There's already some gems out there, nuggets that tell me that there's going to be some positive energy from the people executing or implementing the solutions. I think that's where it helps. This can also work with junior to senior type roles as well, not just departments. But you know, if you have a VP that takes a lot of direction from the people who report to them, then you can.

Start to try and use the product as a way to build up that kind of, um, base and that support. , but if you have a VP that it's their way or the highway, then, you know, testing the product might not actually [00:11:00] be all that fruitful. So I think, you know, I'm glad you brought that up because there are a lot of nuances.

, and it is a tool that you can use to try the product, but you have to use it also intentionally and sparingly. Depending on the different dynamics of the people making the decision. Hmm. 

Alex Allain: Yeah. I like that. I think there's a theme coming through on both of these, you know, that can we at least agree and the demo where you have to have a,, tell me if this is kind of what you're trying to say, , but it seems like what you're really looking for is like, there is some compelling reason that you should.

Be able to get along as an organization that it's either there's like a champion, there's somebody who's really excited that needs to convince other people, or there's like a shared understanding. And if you can't find something that's really like a, a strong reason that someone would want to say yes, then you're probably pushing too hard.

Peter Ahn: Yes, exactly. Yeah, I think that's a great way to frame it. There has to be , even at least, at the very least, a sliver of positivity coming from , what you've presented and the, , and the way in which you're thinking about your product or [00:12:00] the problem that you're trying to solve.

Alex Allain: So let me ask you another question here.

Of course some people are going to be really straight up when something isn't a good fit, but some people can be kind of nice and encouraging. And so, going back to the demo example, you know, or even the can we at least agree. I feel like sometimes people would just sort of say like, well, yeah, I think I can agree with that, but, they're just kind of doing it to be nice and are polite or even just kind of get off the call sometimes without like conflict arising.

And so how do you kind of tease that out in those moments? Or , is this like the wrong frame to be thinking about this in? 

Peter Ahn: No, I think it's a great situation to bring up and I think there's a few ways you can tackle that. One is to try and put a very tangible next step in place where you can see the action happening on the call.

So one example, a very simple example is like, okay, well, if you're very excited, let's actually schedule that second call with the broader stakeholder group. Right? And if you can't do that because they're like, well, I need to check [00:13:00] offline with the people, um, that are going to be the stakeholders, then you could still, you know, have, a mini call to action, which is, okay, who are those people?

Right. By the way, like, who are you going to speak to? So you're basically in both those scenarios, creating, micro milestone moments where somebody has to give you and lean in to your asks. So 

Alex Allain: you're, you're pushing them to make some kind of decision, which forces them to think more seriously.

Whether they actually want to engage with 

Peter Ahn: exactly, exactly. Yeah. And then 

sometimes if you have a product that is very easily sellable within the first five to 10 minutes, let's say, because it's Such a game changing thing. You might even be able to do it on the call to be like, okay, well then can we get the first part of this process started?

Which is for us to integrate with your GitHub code base. So obviously that's like a big ask, but you know, you are at the point, right? It's like, Hey, this is so easy, actually. Like, let's just get the first part of this process started, which is just sign up for our product right now. And I'll show you kind of how to set things up.[00:14:00] 

So. You know, like, and if somebody does that or refuses to do that, that's another signal. So that's another component of this. , you're trying to generate signals and then making the assessment as to whether or not the right signals are being hit for you to continue to invest time 

Alex Allain: yeah. I like that.

The, as an aside, there's a concept that YC has called the Collison install. Oh, interesting. Okay. It's, , in the early days of Stripe, the Collison brothers, when they were pitching And they got somebody who said, yes, I want to use the product. The next thing they'd say is, hand me your laptop. And they would set it up right then and there.

Yeah, that's kind of what you're describing. 

Peter Ahn: Exactly. Yeah. Like, okay, then like, let's put your money where your mouth is. Let's actually get this going, right? If this is so crucial to solving, then there's no reason why we shouldn't get started today. 

Alex Allain: Yeah. So I want to, , I think this is really helpful and I want to like, just continue to build my middle model here.

So basically what you're saying is like, okay, you're in a deal room. You're talking, trying to Make forward progress. You're getting a lot of no's. You're getting a lot [00:15:00] of like meh's from people. Okay, you could just keep pushing, but really the mistake would be to push. Now you need to step back.

You need to evaluate. Do I have any champions? Can I find common ground? Can we at least agree? Okay. If you start to have some of those slivers, then don't just like dive in fully, use that to first redirect your strategy and then find a way to turn that into a way that they can reject you or commit to more action, and then that gives you a second data point.

If they commit, then the next data point is whether or not they then follow through. And if they aren't following through. What do you do then? How do you decide? Well, sometimes people are just late by a day, you know, so like let's say they agree to do an install, but they don't get it done. , how do you then kind of make that judgment call of keep pushing versus don't bother responding and following up?

Peter Ahn: So, I think that's where phrasing can also be very powerful. Right, where there's one way to follow up on action or inaction, which is just to follow up and say [00:16:00] like, I'm just following up on this because we agreed to do this. That's one way, which I think is like the wrong way.

Another way is to say, Hey, I haven't heard from you like the past two weeks. You seem really excited about this, but I know priorities can shift. So should we hit pause for now until you regroup? Or is this a situation where you still definitely want to prioritize this and something else is going on?

Mm hmm. Mm hmm. You know, and, and, , obviously, like, ideally, you say that on a call, but you can also say that in an email in a way where you get a definitive answer because you're giving your prospect options, and all buyers love options. , you know, no buyer likes to be painted in a corner. And the reality is that things do shift so you want to be able to provide the foundation to allow them to tell them things have shifted or allow them to tell you this is still a go but there's some things that are outside of your control as a salesperson that I can't explain.

And then if people don't reply to that type of message You know, I'm not the type of person, this is my style and you have to kind of come into your own style. But I think that I would highly recommend this for startup [00:17:00] founders. Don't worry about continuing to follow up because that in and of itself is a signal.

I hate to be the beggar in situations. I think that sets up a very poor power dynamic and If you have something that really is game changing and you did such a good job on the pitch, which is why you focused so much on the first call, then there's no reason why you should be following up on your feeds.

They should be coming back to you because , they're confident you can solve a problem. So, so that, that's kind of what I would say. Does that answer your question? 

Alex Allain: I thought that was great. Yeah, One of the things that I was thinking about as you were talking about that phrasing was Normally think about like make it easy to say yes, but actually I think you also want to make it easy to say no 

Peter Ahn: Yeah, make it easier to say no actually, right?

Yeah, make it harder to say yes, because When somebody says yes, that creates a lot of work for you That's true. 

Alex Allain: I, there are nuances here. 

Peter Ahn: Yeah, yeah, yeah, there are nuances, but 

Alex Allain: you get the point of that. You don't want to make it hard to say yes because they have to do a bunch of work that you could have gotten done for them so they won't bother doing it, but they would still say yes.[00:18:00] 

Yeah, you want to 

Peter Ahn: basically, what I'm saying is like, creating a little bit of friction actually is not bad. 

Alex Allain: Yeah, yeah, I like that. I think that's really smart and, and something that

should, I feel like we've kind of taken a few different tools in our arsenal and like make it easy to back out, really, to like decommit so that you can stop wasting your time and they can stop stressing about it and you can stop stressing about it. It seems really powerful. 

Peter Ahn: Yeah, yeah, exactly, exactly.

Everybody's busy, so there's nothing bad about giving people time back and giving your team time back, right, if there's not clarity in the deal. Yeah, 

Alex Allain: this also feels like the kind of thing where like leadership, like obviously for an early stage founder, it's fine. They are the one who is holding themselves accountable.

Maybe they have a co founder, but I imagine also when you were running a your, you know, your first couple of hires, it's actually really important to also set the, Expectation in the environment that not every deal is going to come through because those sales leaders could easily waste a lot of their time chasing these kind of dead leads too.

I'm wondering if you have any thoughts on that aspect of it. 

Peter Ahn: Yeah, definitely. I think it's really important to remind the [00:19:00] team that you can't win every single deal. , and to remind folks how cross functional the sales process is, right? So that's the other thing I think for new sales leaders who, um, Um, you have to, with every deal, keep a lot of stakeholders updated and involve a lot of stakeholders too, right?

Like if you're the only person doing something for a deal, there's something wrong. And so I think you need to really set that dynamic of , you know, use as much of my time as a CEO as you need to, to get deals closed. But that also means the impact radius of you spending time on a bad fit lead is a lot larger than just you.

You know, you could be impacting four executives. And in fact, that's what was going on at Twingate because I was talking to my CEO, my CTO and CPO regularly on the big deals. So then it's just not just my time. It's like their time as well. Taking my CTO away from product development to Think about like a contract clause as an example that has implications for [00:20:00] like the operations of how the engineering team works.

So I think that's like really important to think through and you're exactly right. It's, it's very, very important. Doubly important because you don't have teams built up to do this team based selling. It's literally the execs and the founders helping you. 

Alex Allain: Yeah, I love that. That's a great point. Um, and a great example. 

So Peter, you know, one of the things that we talked about at the very beginning, one of the examples was going after one of these really large logo deals.

Obviously that's really exciting. , there's a lot of like, Momentum and desire and probably pressure even within the team when somebody sees like, oh, we might get a Nike, for example, or a NBC that's going to make you want to really push hard to get that deal. And all these tactics obviously are the way to go and handle that.

But I wonder if you have anything to say about how to handle the psychology as well in that moment of being really Amped up and wanting to take home and, you know, get the big scalp or however you want to put it. 

Peter Ahn: Yeah, I love this question. [00:21:00] I think expectation setting is huge. So I'll give you an example.

, I'm helping a client with their sales process and there's a particular lead that is slightly outside of the true ideal customer profile, but it's a really big logo. And so, , you know, what we did there was we said as a team, like the salesperson is like, Hey, I just want to flag that this is outside of our,, ideal customer profile, but it's a big logo.

Peter Ahn: And here's the opportunity of a big logo. It could lead to expansion. I've set up the conversation in such a way where they don't think that we focus squarely on their use case, but that we're more focused on this particular persona. , so, I've, I've done some expectation setting with the lead, but also on the flip side, there's a risk because if we engage, we might lose the deal because it's outside of who we support.

And so, to answer your question, I guess it's a long winded way of answering your question, but basically, it's all about expectation setting and outlining the opportunities, but [00:22:00] also the risks, and make sure you're doing that in a way that's balanced, so that nobody's surprised either way. Mm hmm. So , that's the first thing.

The second thing is to set up a lot more, , points of rejection and leading indicators for the deal progressing. So if it's a large deal, because it's not going to close probably within like a quarter or two, you have to be able to say these are like the 30 things that we're going to track. And if by the time we accomplish the 10th thing, like the 11th thing is really arduous and hard, we know that we might need to leave the deal at that point.

, but here are the perfect storm of events that we need to orchestrate, but know that if at any point one of those items gets derailed, we might need to actually say, okay, it was a good try, but We've now hit our end point with this particular prospect. By the way, if that happens with an enterprise deal, what I'm going to do is audit the [00:23:00] process because there's probably going to be a lot of learnings, even if we didn't close the deal.

So again, it's expectation setting too, where you're saying the value of a big deal, isn't just the big deal. There's learnings, there are micro milestones you're tracking, and then there's also risk. And so communicating all of that upfront, I think is really important. makes for a much healthier team dynamic when the deal doesn't close.

And then obviously when the deal closes, you don't have to worry about the dynamics because people are going to be super jazzed and happy regardless of how the deal closed. 

Alex Allain: I like that. I really like what you said, particularly, I mean, obviously the expectation setting piece sounds really critical. And also once it's been set that way with the pros and the cons, It probably helps you like reset your own psychology.

You know, you, you sort of get off of the little high of like, Oh, Nike reached out to like, okay, there's a balanced view of that. And then I think the second thing that you, you really highlighted that I liked quite a lot was the importance of those milestones and [00:24:00] micro milestones, the leading indicators of the deal.

I mean, I feel like that's something that applies everywhere, but, , also is. Really, really important for something as a long cycle as this. Yes, exactly. 

Peter Ahn: You need to be aligned on the leading indicators. 

Alex Allain: All right. Well, Peter, I feel like we've covered a lot here. We touched on how do you, in the moment , you're seeing a deal that might be going off track and you need to tell if you should eject to get to those, can we at least agree statements, finding , Some energy, some positive reason to go forward, but also then using that to give them a chance to say no and making it easy to say no, so that they will actually do it so you don't waste your time and then setting clear expectations and really thinking about the leading indicators of a deal throughout the process and relying on and trusting those leading indicators as well, which I imagine probably takes a little bit of experience to do, that collectively I think is a good toolkit for folks to take away from this.

, [00:25:00] anything you want to add on to that? 

Peter Ahn: No, I think, I think that's a good summary. , don't waste time with deals that are never going to close. And yeah, there's a lot of nuances you pointed out too. So there's not like a black and white approach to this, but hopefully we've provided enough things to think about, , when you're in one of these situations.

Alex Allain: I hope everyone comes away with that phrase, don't waste time with deals that won't close. When you said that, I was like, yeah, that's what people should really remember from this. And then there's a bunch of tactics. Yes, exactly. Cool. Love it. Alright, well, as, , we want to thank our audience again. We would love to see some likes and subscribes.

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