Adam Kay (video) argues that when selling to C‑suite executives you should limit the number of questions (ideal ≈4) and use "context-led questions": short, high-value questions preceded by a specific observation or insight demonstrating prior research. He cites a Gong analysis of ~500,000 SVP-level sales calls showing win rates fall after ~4–5 questions, contrasts generic questioning (which irritates executives) with context-led questioning (which signals business acumen), and gives examples (Tim Ferriss/LeBron episode and a fictional sales engagement example).
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So years ago, probably 10 or 12 years ago at this time, I was an account executive, and I was running a sales meeting with a chief operating officer and a director of operations. I had already met with the director of operations once or twice before. I would consider him to have been a champion for that deal. And he sponsored a meeting with the coo. And so this guy was the economic buyer. And I walk into this meeting where, you know, it was done over gotomeeting, and I asked a question, and I kind of got a curt response. And I asked another question, and I got an even more curt response. And after three or four questions, the COO stops me, and he goes, just stop. I don't have time for this generic line of questioning. And then he literally left the GoToMeeting room like, he hung up the call, and me and the director of operations were just kind of sitting there twiddling our thumbs, not knowing what to do next. Now, as a funny side note, the director of operations goes, I'm about as confused as you because we teach our sales reps to ask the exact same questions that you were. So that's one story. That was 10 or 12 years ago, right? I just got absolutely kicked in the teeth. Now Fast forward to 2019, I think. This was the year I did the study. I was working with the GONG data science team to analyze this huge pool of anonymized data. And we analyzed what I remember was probably about half a million sales calls, specifically with SVP level buyers. So, like C suite executives, these were the kind of sales calls we were analyzing. And if you look at the data here, you can see that there's actually a negative correlation. Okay? A negative correlation between the number of questions you ask in a meeting with an SVP or C Suite executives and your likelihood of winning that deal. Right? So your odds of success actually skyrocket after like, three or four questions. Maybe five. But after five or four questions, every additional question you ask starts to decrease your win rate, starts to decrease your likelihood of winning that deal. So what's up with that? Right? Us in sales, or we in sales, we are taught that you should ask more questions and that questions are the key to sales success. Now, it turns out that it's not just asking questions is a negative correlation with success with C suite executives. It's asking typical questions. It's asking generic questions, like I did with that coo. C suite executives do not want to help you gather information. They expect you to have done your homework prior to showing up on a meeting with them. And so you probably have room for four or five questions, but they have to be rock solid questions, right? These are not the kind of questions you ask your champion or coach or other like mid level person in the account. And what you can actually see with this other piece of data is that fewer questions with this, with these C suite executives, you know, led to success. So four questions was the ideal number in winning meetings with C suite executives, and eight was the most common number for meetings that were unsuccessful with C suite executives, for meetings with them that led to deals that didn't close. So what's the answer here? Well, the answer is what I call context led questions. Okay. These are the kind of questions you want to ask C suite executives. And the good news is you probably only need maybe two or three of them. You can ask one or two other questions beyond that, but they signal to the C suite executive that you've done your homework, that you are an A player, that you're not going to waste their time, and frankly, that you have business acumen. So what's a context led question? I'll tell you what it is. I'm going to give you a couple examples so you can go try this yourself. Context led questions are questions that are preceded by sharing an observation or an insight about their business that give context as to why you're asking a question. Okay, so in other words, right before you ask a question, you lead into that question with an observation or an insight that signals that you have a high degree of business sophistication, that you've done your homework. Okay? So if you've ever heard of Tim Ferriss, right? Most of us have. He has this podcast called the Tim Ferriss show where he interviews high performing people from different walks of life, right? Business people, athletes, politicians, even doctors, scientists, all kinds of people. And years ago, he had this episode with LeBron James and LeBron James, personal trainer at the time, whose name was Mike. And what you're looking at here on the screen is an example of a context led question that he asked both Mike and LeBron. It says, Mike, I'd love to dig into recovery and injury prevention. LeBron, you're a bit of a unicorn in the sense that you've played more than, as I understand it, 50,000 minutes in your career. Most hit a wall and deteriorate after 40,000. So you're defying all the predictions of player decline. So, Mike, maybe you could give us a window into some of that. Could you walk us through some of the tools of the trade and the approaches that you use to help with recovery between games. Now that is a powerful question. And if you ever listened to that episode, you know that Mike and LeBron go on a very long, rich tangent about recovery and injury prevention. Now compare that question, right? So Tim used a lot of context. He said, lebron, you've played for 50,000. Typical is 40,000. And then people start to go downhill, right? Lots of context and insight that preceded the question about, walk us through your injury prevention process. Now imagine if Tim did not do that. Imagine if he just dove in and he's like, so, Mike, walk us through how you recover LeBron between games. It would have felt like a pickaxe, right? It's almost like irritating. It feels like, oh, man, this guy's just like pummeling me with questions. Even if you're only a couple questions in, when you overlay your question with insight and observation like this, it buys you time. It's like an investment in their emotions. Bank account. And now they're excited to answer your question instead of annoyed and irritated like the COO that I told you about at the beginning of this. So a couple tips and tactics to make this actionable for you. There are generally three areas you pull from when it comes to asking context led questions and finding the observation you want to share. Okay, all of these, you should do these in your pre call research. But number one is doing research about their company, right? Do they have any public earnings or 10k or anything like that? Or press releases or just executives jumping on podcasts or something that speak to an observation you can share that's relevant to a question you can ask them? That's one. Number two is research about their industry, right? Maybe they're going through consolidation. Maybe there's something geopolitical happening within their greater industry. And then the third source of context led questions is other external factors that might be impacting their business. This often has a lot of overlap with the second one with, you know, like industry insights. And so the goal is to research these three areas and find an observation that you can tee up and then ask a relevant question based on whatever observation you teed up. Right? They have to be connected, the observation and the question. You can't say, hey, I noticed you went public last year and the stock price has been flat. By the way, what's your favorite color? Okay, that's not gonna work. They have to be relevant to each other. The observation, the question. So I'm gonna give you one example, just so you have a sales example. I just walked you through Tim Ferriss's example. It's still a great example, but it's a podcast. So here's what this might look like if I were selling to a sales technology company that decided to enter the sales engagement space, right? Like Outreach and gong and Sales Lofts World. And so let's say I'm, you know, maybe I'm selling to, I don't know, their CRO or coo. It doesn't really matter. Some C suite executive that has influence over decisions like this. I would say, John, I'd love to start by talking about something I read on your company's recent press release. It mentioned your company is entering the sales engagement category and plans on competing in that space going forward. I'll make it clear why it's relevant for us to talk about this, but do you mind if we start by talking about what factors drove the decision to enter that market? Now, in this fictional example, I don't know what we're selling here. I'm assuming it would be relevant to, you know, them entering the sales engagement category. Maybe I'm selling some sort of competitive intelligence tool, knowing that they're going to need that if they're going into that bloodbath of a space. But the fact, the point is, I led with homework. I led with insight and observation about what's going on in their world. It immediately signals to the executive that I am bringing my A game. I've done my homework and I have a level of business acumen that's going to make you want to hang with me on this call instead of what most sellers do and just say, so what drove you into, you know, sales engagement? And they're asking as if it's like some, you know, piece of small talk and the executive just doesn't react well. Maybe they're polite in the answer. Maybe they're not so polite like the COO at the beginning of this video, and they grow visibly irritated. So that's the lesson of the day. Context led questions. You don't have to do every question like this, right? That would be kind of insane as you ran a full discovery call and every question was context led. Honestly, one good one can propel you onto a very productive path. You usually don't have to do more than like two or three of these in a single call. Even that's like starting to, you know, become overkill. Just a couple, even one really good context led question. That is how you resonate with C suite executives, at least when it comes to asking them questions. That's how you impress them. I hope this was helpful, and I will see you in the next video.
