Selling to the C-Suite: Why Better Questions Beat More Questions (Part 1)

Chris Orlob (CEO, Pclub IO) introduces a short course on selling to senior executives by replacing generic discovery questions with "context-led questions." He frames the problem with an anecdote of a COO rejecting generic questioning, cites Forrester findings (9% of sales calls perceived as valuable; 7% lead to follow-ups), and a Gong analysis of 39,105 deals showing successful executive meetings average ~4 questions while unsuccessful ones average ~8. The course promises to teach techniques that produce longer, richer responses and improve credibility, close rates, and relationship advancement.
Questions this video answers
9% (Forrester)
7% (Forrester)
39,105 deals (Gong analysis)
Successful meetings: ~4 questions on average; Unsuccessful meetings: ~8 questions on average
Chapters
My name is Chris Orlob. I'm CEO of Pclub IO. When asking advanced level questions like the ones you're going to learn in this course, your goal is to earn massive credibility with even senior buyers and get long, rich, powerful, positive responses to your questions in a way that helps you close more deals or otherwise advance the relationship. Okay, so this course is for those of you who already have some of the core fundamentals of discovery in place. This should not be the first ever discovery training you've taken. So assuming that's the case, we're going to start with a little bit of a pop quiz. Okay, so I want you to answer this before I show the answer. What percentage of sales calls do C suite executives agree the time they spent on the call was valuable and time well spent. What percentage of sales calls do C suite executives feel the time they spent on the call was valuable? A According to Forrester, that answer is just 9%. Less than 1 in 10. That's a pretty low hit rate. Now here's another one. What percentage of sales calls are C suite executives willing to schedule a follow up on? Okay, what percentage do you think that is? Before I show the answer, take a wild guess. Again, according to Forrester, the answer is 7%. So while those are pretty dismal numbers, right. C suite executives are not exactly having great sales experiences with us as sales and customer facing professionals. It also represents a massive, massive opportunity for you because if you can up level your skills and cut through this and not be a statistic, then you're automatically going to make a very sharp, contrasting positive impression. Okay, so this course is not just for selling to C suite executives or senior executives. But I'm going to tell a story that illustrates those statistics so that you understand some of the problems you are going to be able to solve for yourself by mastering these skills. And here's how the story goes. This was probably over 10 years ago at this point. I was in a gotomeeting room with a COO and his director of operations and he says just stop. The COO practically spat that through the at the time gotomeeting conference room and he said I don't have time for this generic line of questioning. Okay, so at the time I was about two years years into my first account executive sales job. I thought I was doing everything right. I asked open ended questions to unearth pain just like the sales books told me to do. And yet this COO kicked me in the teeth, leaving me and his ops manager twiddling our thumbs. He actually Left the meeting room and the ops manager said, I'm as confused as you. We teach our reps to ask the exact same questions, which I thought was kind of funny, but I'm curious if you've ever been there before, been asking a C suite executive or really anybody discovery questions, and it just feels like they do not want to answer them. Okay. If you're in sales or a customer facing role, you've probably felt that before. And in this course and in this lesson, we're going to unpack how to prevent that from happening, among several other things. Because the COO in my story, he wasn't just a cranky guy. He wasn't just having a bad day. Here's why. He kind of jerked me around and actually stormed out. Open ended discovery too. Open ended generic discovery can backfire with C suite executives and really anybody. Okay. All of this still applies to you if you're not selling to C suite executives. For example, if you sell K through 12. Right. Maybe a superintendent or to government or something like that. So a few years ago, when I was still at Gong, I led an analysis of 39,105 deals. Okay. The Zoom calls were analyzed with AI to find successful and unsuccessful selling behaviors. And this study revealed a pretty counterintuitive insight. And it turns out that according to this data, asking discovery questions to C suite executives can decrease your win rate. It has a correlation with decreases in win rate. And what you're looking at is a chart that showcased that data. Once you've asked a small handful of questions to a C suite executive, you can see that on the growth curve on the way up, every additional question decreases your odds of success. In fact, according to the same dataset, successful meetings with the C suite only involve about four questions on average. And unsuccessful meetings have about eight questions on average. It's worth emphasizing a point I skimmed over when it came to this data set. This data was based on sales calls and deals where an SVP or C suite buyer was present on the call. Okay, so senior executives have what I call discovery fatigue. Okay, this takes us back to our opening story. The COO who kicked me in the teeth, a senior decision maker. He probably felt like he was being interrogated. Okay. He had probably already been through the quote, unquote discovery dance with two to three other competitive sellers at that point, before he even got to me. And it probably felt taxing to answer all of those questions to him. To him, especially because admittedly, they were generic questions. But it's not just him. Okay, Senior decision Makers in general and many buyers are becoming fatigued by sales people's generic questions. Okay? Those questions can feel a little bit like pickaxes. Okay? They're becoming fatigued by them. So what do we do about that? That's the important question. When every sales book on the planet tells you to ask more, not fewer questions, where do we turn to close more deals when we have to sell to executives or other buyers that might have fatigue from those types of questions? Well, the answer is not to stop asking them questions. That is not the takeaway from the lesson. And I want to be super clear about that. It's not that the C Suite hates being asked questions. It's that they hate being asked dumb questions. Okay? They hate being asked generic questions, questions that you should have asked somebody else in their organization to prepare for the meeting with them. They don't want to be your research assistant. So the answer then is, instead of doing that is it's to answer or to ask rather context led questions. And that is the topic of this course. Okay? So this short course is designed to improve the response you get to your questions, whether you're an ae, AM or csm. Okay? It's to get more positive, rich, longer responses that lead to closing more deals or advancing the relationship. It's to eliminate that buyer irritability or impatience with discovery that I showcased with that story and with that data. It's to deliver powerful first impressions to even senior buyers that immediately separate you from other sellers, that put you into a bucket of. This person actually knows what they're talking about. And that's equally true if you're an account manager or csm. This course is going to help you establish credibility and business acumen in eyes of executives so that you have equal business stature and you have a posture of being able to influence them. Okay? This course, once you get really good at these skills, it's going to give you a powerful feeling of confidence, maybe even peace of mind. And ultimately, this is going to help you boost your close rates and income. And the way I can make that claim, or the reason why I can make that claim is once again, according to some of this GONG data, there is a direct correlation between the length of response to your questions and success rates, be it close rates, advancing the deal to the next stage. Whatever the case is, there's a very strong correlation, as you can see on this graph. This was done a few years ago, but I imagine it still holds up to be true. So when you get really good at context led questions, you'll get very long, rich response which correlates with sales success or customer facing success. And so the way we're going to do this is with a new, modern, powerful questioning technique that we call context led questions. I'm going to tell you more about this in the next lesson. I'll see you there.
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