Make the Sales Conversation Uncomfortable

I don’t think you’re going to be ready to buy. That’s what one of my coaching clients said recently to a prospect on her discovery call. And it completely changed the dynamics of this deal for them. And it took guts. And like that approach takes guts. And it’s the kind of moment that most sellers never really get to because they stop digging in the discovery process way too early. By the way, if you like applying this kind of stuff to your sales process, I go deeper in a newsletter every single week. You can sign up if you want at https://www.google.com/search?q=raiseyouremail.com.

One of the most common themes that I talk about with sellers in coaching is that all roads lead to discovery. And what I mean is all of the questions I get are typically about what to do at the end of the deal. They need to incorporate some other decision makers that I didn't think about, or there's a pricing objection, or they're kind of stalling out, they don't feel like there's any urgency. So I always get questions about what's happening at the end of the process. And I say all roads lead to discovery because all of those things can be traced back to things that we should have learned or could have learned if we were asking the right questions in the discovery process. So all of the things that you're seeing at the end lead back to something that we could have done at the beginning. Right?

And a big one of those things is just understanding pain points. I mean really understanding it. And the vast majority of sellers don't do it well. Like I listen to a lot of calls and it's because they stop at the surface level of things. Right? So they ask the scripted questions or the playbook questions and they get the standard answers from prospects and then they move on to the next question. Right? Like they're filling out a form. Okay, got this question answered, check. Okay, question answered, check. And I'm constantly coaching sellers on pulling on those threads. Like listening to what you're hearing and diving deeper than the surface level answers that you're getting.

And sometimes that means having a really candid discussion with somebody. Or it means challenging a prospect who isn't answering questions or is giving you really surface level answers when there isn't a perceived pain point. Sometimes the best thing you can do is pull on that thread. And when you feel like there's something below the surface that you're not getting to, you've got to be candid sometimes about it. And it's tough. Like it requires emotional intelligence. It requires some courage. Like consultative selling is not for everybody and there's a reason some people are really f***ing good at it and there's a reason that some people aren't.

And I'll give you a specific example. I got an email from a coaching client last week who wanted to share his experience incorporating this. Like going deeper on the pain point. So we've talked about it a lot and a lot. So he did it and wanted to share it with me. And here's what he said. I'm just gonna... I'm just gonna read his email to you.

"I had originally called them through Hubspot..." — he talks about his recording. He says — "He gave me a small amount of pain and seemed to be ready to wrap up the conversation. Honestly, I was about to do the same and walk away disappointed, feeling like I hadn't uncovered much real pain. But instead I decided to dig further. I said to him, from my selfish standpoint of wanting to sell you services, I can absolutely bring you a proposal. It's no problem. But I don't think you're going to be ready to buy. And I'm because I'm not seeing enough of a problem... a big enough problem for us to solve."

Up to that point I'd been speaking to the CIO. Now I was talking directly to the owner. With some hesitation he then shared that the CIO's days may be limited. That he's spending 340 grand a year across three internal IT people and that the CIO has been slow to respond to me even though the owner himself has been pushing this initiative. And the point is this... — This is still his... his email — "The point is this. Don't walk away when you think there's only a little pain. Make the conversation uncomfortable. Keep digging. If there's gold there, you want to find it."

And I couldn't have said it better myself. Like getting that email was like a... it was a fist pump moment. Right? Because the candid conversation that he had completely changed the dynamic of that deal. And it differentiated that seller from every other seller... like if they're talking to other companies, they're all going to be getting surface level answers. But he got to the real problem. Like there was a respectful challenge and there was honesty, there was candor, there's transparency, like all things that I coach on in... in the process. And there was getting below the surface level pain. Like the pain that the prospect didn't want to share but it was necessary. Like as... as a seller to like actually understand what is the problem that you were solving.

If you don't know the problem you were solving, the prescription you were offering is not going to be seen as... as credible as it will be if you do. And because this... it shifted the complete perspective from solving some IT issues to solving a fundamental business problem. Right? One that's costing 'em hundreds of thousands of dollars and allows you as a seller to like get to the core of what's... what's actually going to move the deal forward. What is the real motivation? What is the real urgency? What is the real value of buying your services? So I share this with you to like reinforce that when you apply these lessons, when you dig deeper in discovery and you're more real with people and you're better at getting below the surface, you are going to close more deals. Hope it helps. Adios.