Adam Kay (speaker) teaches sales professionals how to convert small customer issues into large, deal-worthy problems by probing deeper during discovery. Using a Gong-era discovery-call example, he shows how to move from a surface desire for "visibility" to operational problems (long sales cycle), then to financial risk (11-month cash cycle leading to dilutive capital needs), which raises willingness to pay from ~$50k to $500k+. The clip ends with practical tips: ask about the business context that made this a priority and use softening language rather than repeatedly asking "why."
Chapters
If you're a sales professional, you really, really need to etch and emblazon this concept into your consciousness. Okay? Little problems, little commission checks, big problems, big commission checks. Now you can actually turn little problems into big problems, big customer problems, and therefore earn big commission checks. You can manufacture these circumstances in many cases. So let me tell you a quick story. This is a discovery call I was on probably five or six years ago while I was at Gong with one of the reps that worked for me. And we had this discovery call. It was a sales enablement manager in the room, and we also had power in the room, the SVP of sales and services. And they came to us, they came inbound, and we asked them. We kicked off by saying, what motivated you to look into Gong? And the sales enablement manager took over the conversation immediately. And he said, we need visibility into our sales conversations. Okay? So the challenge with that is that's not really a problem. That's not. It's not even a little problem. Right. We're talking about how to turn little problems into big problems. It's not a problem at all. That is a desire for a solution. Right? Visibility and the willingness to spend money on something like that, something that surface level is probably zero. And so we said, okay, well, what's driving you to crave that visibility? And he went on, he peeled the onion one level deeper with us, and he said, well, reps are struggling to power, so we need to coach them up on that. We said, okay, tell us more about what's going on there. And he says, as a result of a weak ability to access and then sell to power, our sales cycle is nine months. And our annual operating plan suggests that it should be six months. Right. Like we've built our company or our annual operating plan around the assumption that our sales cycle is going to be six months. So now we're starting to get to a problem we've transitioned from a desire from us for a solution. Right. Very surface level, to an actual problem. But I would also suggest that this could be considered a little problem depending on the company you're selling to. Right. We don't totally understand the context enough to chalk this up to a little problem or a big problem. Right. Their willingness to pay at this point is probably $50,000. Right. If they have 500 reps, that's not going to be enough to justify a purchase. And so we then took a step back and we used a little bit of softening language to continue peeling back this thread. And we said, this is going to Sound a little bit redundant. I understand that, but you've probably right. If you're like any other sales organization, you probably have six or seven or eight big challenges that you could be solving right now. And I'm curious what's going on in your business that's driving you to prioritize this one among all of the other shiny objects that you could be tackling right now. And notice now that power took over the conversation. Okay, this is worth writing down and remembering. The closer you get to the center of the onion, the core of the problem, the more you're speaking Powers language. And so now that we were getting to the core of the issue, she took over the conversation and she said, well, nine month sales cycles mean we have an 11 month cash cycle. Okay. What she means by that is when they close a deal, on average they sell net 60 payment terms. Right? Which means when they close a deal, a customer doesn't actually wire them the check for another 60 days after close one. So from the time they start a sales cycle to the time cash hits their bank, 11 months. And we asked her in a softer way, tell me why that's such a big deal, tell us more about why this is an issue. And she said, well, this 11 month cash cycle puts our cash position at risk, especially when you forecast the business two years out. And if we don't reduce our cash cycle down to something more manageable, like say eight months or so, then we're going to need to raise more capital. And in this kind of situation, when you're raising capital to bridge a cash flow gap, it's typically very dilutive capital. Okay. It's not the kind of capital where you can get good terms because you're just, you know, pouring gas on growing the business. It's basically a bridge round. And it very likely could be a bridge round, which means millions and millions of potential dollars could not for sure, but could evaporate in terms of valuation for the company. For her specifically, that means she's going to take a big potential financial hit right when it comes to exiting the business and the company will as well. So we have gone from right, look at the screen from left to right, we've gone from we need a little bit of visibility to we need to coach our reps to sell on power to we need to decrease our sales cycle to we need to decrease our cash cycle to millions of dollars worth of company market capitalization or valuation is at risk if we don't solve this. And as a result, the willingness to pay shot up to $500,000 or more. Okay? You can replicate this same motion in your own sales cycle. Now, you do need to be talking to the right people in many cases sometimes. And I get this, mid level people won't always be able to answer all the questions you're trying to get at when you're trying to peel back the onion. But here's a few quick tips to replicate this in your own deals. Okay? Number one, as you start fleshing out the problem, try asking this question, right? When you know you're at like the surface level, try asking what is going on in your business that's driving you to prioritize solving this, right? I imagine you probably had a meeting with colleagues where you all talked and defined the problem and its level of magnitude. What did that conversation sound like that will reveal so much information and context that you didn't realize before that empowers you to build a case for driving urgency and a far, far bigger deal, right? That's how you go from a little problem to that generates little commission checks to a big problem that has the power to generate very, very big commission checks. Now, the second quick tip I'll give you is you can't just ask why, why, why, why, why over and over, even though that's kind of what you're doing, because buyers are going to get annoyed. And so you have to use this softening language that I suggested throughout. So things like, I understand that this question is redundant, but here's why I'm asking it and kind of justifying why you're asking some questions. So use some of that softening language and then try the question that I suggested, right? What's going on in your business that's driving this to be a priority? And you will be shocked and amazed occasionally at some of the answers you get.
