In this sales‑training session Dan Smith argues that the single most important skill for any salesperson is the ability to ask great questions. He outlines three categories of questions: closed‑ended (yes/no or factual), open‑ended (any response beyond a single fact), and "trick" questions, which combine a closed‑ended question to set context followed by an open‑ended question to elicit detail. Smith demonstrates that asking only open‑ended questions can backfire, as vague prompts like “What keeps you up at night?” often produce irrelevant or unhelpful answers. Instead, he recommends a two‑step approach: start with a closed‑ended question to establish a concrete fact, then follow with an open‑ended question that builds on that fact. Through a live role‑play with audience member Alex, Smith shows how to identify whether a question is closed or open, how to use follow‑up probes (e.g., “What was good about it?”) to move a conversation out of a "conversational cul‑de‑sac" and avoid an interrogation feel. He emphasizes active listening—mirroring the prospect’s language and digging deeper on specific cues. Smith also ties these techniques to Dale Carnegie’s principles from How to Win Friends and Influence People, stressing the importance of making the prospect feel heard and important. The session concludes with a call to practice converting the weekend‑analogy exercise into real sales conversations with strangers.
Chapters
Okay, let's go into the next part. The most critical skill in sales is asking great questions. What are the 2 fundamental types of questions that we can ask? 2 fundamental types of questions. What? Ask me the question. What's up? Now I want you to consider the types of questions based on the answer that you get. If I say nothing, what kind of question did that make it? Close or open? Close, because I answered with one word. A closed-ended question is yes, no, or fact. How many employees do you have? What tool are you using today? What is your title? All of those are closed-ended questions. On the opposite side, we have open-ended questions. Can anybody define an open-ended question? It's basically anything else. Gets them to open up. Okay, how was your day today? Requires me to go forward a little bit. Or be a little bit more open-ended. What is the only type of question we should ask in sales? Open or closed?
Open.
That was an example of the third type of question. That's called a trick question. You need to ask both. I was always taught to only ask open-ended questions, but what if I asked you, what keeps you up at night? How would you answer that question?
Uh.
You could go all over the place. Oh, I was staying up too late studying, or I have a new puppy at home. All of these things that your software solution or your service cannot solve. So an open-ended question like that is a bad question to ask in sales, because the customer will not know how to respond to it. So what I recommend you ask is a closed-ended, And then an open-ended question. And the closed-ended helps you set context. Open-ended question gets them to elaborate. What is going on? Now, the trick here that I have found is that we all tend to make it about ourselves. So, I need 2 people from the audience to come up on stage with me, and I wanna show you an example about how closed and open-ended questions work together. Anybody feeling like they really wanna learn how to become a great salesperson? Come on up. Come on up. Yes, I haven't talked to you yet in the blue sweater. I love it. Anybody else who I haven't talked to yet? Love your engagement. Love your engagement. Anybody else? No, you. Yeah. No, no, no. You've answered before. I love it. I'm coming back to you. You can help me coach on this. Come on up here. Okay. What's up?
What's up?
What's your name? Alex.
Alex.
And your name? Alex. 2 Alexes. Well, bless my lucky stars. This will be easy. Okay, so what I want you to do, I want you to be the customer, I want you to be the salesperson, and in this case, all I want you to do is ask him about his weekend, and I want you to listen to his response and get him to tell you more. Go a little bit deeper. Just keep asking questions about his weekend. You can make it up. Don't, like, go crazy, but, like, you don't have to be personal if you don't want to. The exercise here is listening to the questions, and I want you guys to try and point out, are these closed-ended or For this scenario, this is now getting into the 20% of how you learn something. You just learned open and close. I want you to start this off as the customer and say, ring ring, this is Alex. And then you will know to take it away. Ring ring, this is Alex.
Hey Alex, how was your weekend?
Uh, good.
That's good. Uh, what did you end up doing?
Nothing.
Uh, I thought you decided that you were gonna go to the roller derby.
Okay, so Alex, you were being tough right now. How did he respond to those questions? One word, right? It's very tough for you to go through. So let's go through the first question. What was the first question you asked?
How was your weekend?
How was your weekend? Is that an open or closed-ended question? Now this is a weird question. I realize that there's an actual terminology for it. This is called a conversational cul-de-sac. It's an open-ended question But if somebody like this guy makes it closed, there's not a lot of room to work with. So here's the way to get him to open up. He said his weekend was good. What's a way that you can use that word in a follow-up question?
Like, you just start with good.
What was good about it? What was good about it? What made it good?
Yeah.
And now you are showing the next step of it. This is called active listening, because remember, your second question you asked, what did you What did you do? And he said nothing. But if he said it was good and then you follow up with that, what made it good? He can't say nothing.
Yeah.
So now we're getting him to open up. You're making him guide in a certain way. Thank you. Right. So let's try that again from the top, and I want you to pick up these tone words that he says and get him to elaborate deeper. You ready for it? Yep. Ring ring, this is Alex.
Hey Alex, how was your weekend?
It's pretty good.
That's good. What was good about it?
I went to the roller rink.
Yeah, how was the, how was the, the rink?
It was good. I rolled around on blades.
What kind of blades do you have?
Plastic ones.
What kind of plastic are they? Black.
Okay, so now we're getting into this mode right now. So first of all, round of applause. Thank you guys for doing that. That was a really good example. I really appreciate it. Okay, so there was a lot of questions going on right there, about 10 questions that I felt in a row. Now, this is a problem when it comes to sales. If I were Alex in this case, I would feel like, why are you asking me all of these questions in a row? It starts to feel like an interrogation.
Defensive.
Defensive, right? You'd be like, all right, where is this going? It's not fun for you necessarily to answer all these closed-ended questions. So what we need to do is turn it into an open-ended. So you asked him, what did you do? What made it so good? He said he went to the roller rink. And then what did you ask? Do you remember? How was the rink? And then now you know he's a closed-ended guy, so he's gonna say it was good. What's a way that I could get him to open up? What's an open-ended question I could follow through on that? Potentially. So the feedback was try and engage with it, try and add some personal connotation with it. Oh, I love going to the roller skate rink. Unfortunately, that makes it about you. It's a little bit too early to bring you in. And here's now the second book that I wanna recommend to you, How to Win Friends and Influence People. Has anybody read that book? I love it. The big thing— oh, a lot of you, good, good, good. So a lot of the things that I picked up from that book come down to this simple idea that if you want somebody to like you, what do you have to do? Accept them for who they are. Make them feel important. Absolutely. When you talk about that person, get them to open up about themselves. If all you do in a conversation is get them to talk about themselves, they're gonna leave and be like, wow, that Alex, most interesting person in the room. So all you need to do in this case is ask an open-ended question. What made you choose to go to the roller rink? Is roller skating a passion of yours? What made you passionate about it? Why did you choose to become passionate about roller skating rinks? What happened in your childhood? Get them to open up in a way that they can't answer with these one-word answers. Now, the weekend analogy here is something that's accessible to all of us, but I want you to now try and convert that into a sales conversation, and I want you to practice this with strangers.
