When engaging with new prospects, figuring out the best questions to ask in sales can make or break your deal.

This week on INSIDE Inside Sales, Darryl is joined by best-selling author, international keynote speaker, and CEO of Tony Morris International, Tony Morris. Darryl and Tony talk about how powerful a simple ask can be and discuss how to get into an ask mindset. They also share their thoughts on open versus closed questions, how to ask thought-provoking questions, and ways to build relationships, all through the power of an ask. Learn how to ask the questions that keep your clients talking on this episode of INSIDE Inside Sales!




Host: Darryl PraillVanillaSoft

Guest: Tony Morris, Tony Morris International


Darryl Praill: So I have to be honest with you, kids. I have to talk about something. All right, it’s going to sound really lame. I have to admit it’s gonna sound like I’m a 50-ish-year-old man who hasn’t grown up yet, but here it goes. Sit back, relax. And don’t judge me. Here it is. I’ve never admitted this before. I’m really struggling. Okay. I have a super power. It’s true. I have a super power. No, I don’t wear tights, and I don’t have a cape. I don’t stop crime. You know, crime. I don’t help crime fighters. I don’t stop the bad guys. And I don’t help little old ladies cross the street, although I should. I don’t appear in print often and have a direct line to the police chief or the mayor. Little kids do not aspire to be like me, but despite all of this, yes, it’s true. I have a super power. 

Darryl Praill: This is really painful to share cause it’s so vulnerable. What is my super power? Okay. I ask questions. Okay, don’t judge me. I know, I know. You’re thinking to yourself, “Damn, that’s an impressive super power. I’ve never, ever met somebody else who has that super power before. Darryl, tell me more about your super power.” Okay, since you asked, I will. I ask questions. You know, I ask questions when I am talking to a prospect. I ask questions when I’m nervous. I ask questions when I’m meeting somebody for the first time. I ask questions when I want to make a good impression. I ask questions when I’m in a job interview. I ask questions when a reporter is actually asking questions of me. I ask questions of my audience, even though they’re asking me for answers. I ask questions. That’s my super power. So you’re probably saying to yourself, “Darryl, okay. I know you’re vulnerable right now, and you’re feeling exposed.” And you’re right, I am, and I don’t want to be that person, and I’ve heard people say this, but that’s, they say, that’s not a super power, but they’re wrong. And let me explain why they’re wrong. 

Darryl Praill: When I want to make a good impression on an employer, I ask questions like, “So tell me, you know, who do you compete with? Tell me how you’re different. Tell me why I would buy you. Tell me what a happy customer would say. Tell me what a not happy customer would say. Tell me why I should work for you versus anybody else. Tell me what my predecessor did really well. Tell me what my predecessors did wrong. Tell me what I will have done in the first 6, 9, 12 months that made you go, ‘Praill was a good hire.’ Tell me when I meet somebody I don’t know.” I’ll simply say, “So what do you do?” And they’ll say, “I do X, Y, or Z.” And I’ll say, “Well, that’s interesting. So what’s involved in doing X? How long have you been doing X? What skills do you need to do X? Do you like doing X? What does your spouse think of you doing X? Really? Well, when you’re not doing X, what else do you do?” 

Darryl Praill: And what I’m doing is I’m making them at ease, right? Cause they’re talking about something they know really, really well. They’re talking about themselves, and along the way, they’re giving me tons of information I can react to. And really, there’s nothing for me to put myself out there on. I don’t have to be witty or funny or engaging. I’m just asking questions. And I’m looking at them longingly in their eyes. And I’m listening attentively even though my mind, I might be thinking about something, what’s going to be for dinner tonight, or my stomach is upset or, you know, I got that assignment I still need to do for the boss. And you know, my latest social media video could have been more engaging, but in my mind, you know, that’s what’s going on. But outside, I’m asking them questions, and they leave, and they turn to their spouse or their friend, they say, “That Praill guy, he’s just a nice guy. He listens well. He asks the best questions. I really like him.” 

Darryl Praill: You see, when you ask questions, it takes all the burden off of you, and it actually feels like you’re giving control to them, to the person you’re asking the question of, because they’re the one doing all the talking. But the reality is you’re asking a specific question because you probably want to get a specific answer. Even if it’s as simple as saying, “I want to know if this job is right for me, and if I could be successful here. I wanna know if I like this person, do we have anything in common?” It’s really rude to say, “You know what, I’m not sure if I like you. I’m not sure if you’re a cool company. I’m not sure if we have anything in common.” People get upset about that. It’s really weird. And that’s what makes it, my friends, a super power. Because when I ask the question, and the way I asked the question, and the sequence I asked the question, and the intentionality of the question I’m asking, the recipient just gives me information. No cost. Just gives me information. Could you imagine if I said, “Can you afford my product?” “Well, you know, I’ll let you know what I can afford.” Whereas, you know, “So tell me about the size of your team. Tell me, you know, tell me a bit about your tech stack. Tell me about any contractor that you use. Tell me the biggest problem you have.” And if I ask enough questions, I can figure out if this person’s got a budget or not without ever being explicit.

Welcome Tony Morris

Darryl Praill: And all of these reasons are why it’s a super power. It really is. I don’t put it on my resume; I probably should. Maybe I can put it in my LinkedIn profile. What do you think? Maybe people are doing keyword searches on that. Maybe recruiters will be looking for people who can ask questions cause they should be, especially if you’re in sales. So who’s the expert at all things related to asking? Well, I’m glad you asked. Allow me to introduce to you Tony Morris. Tony is an international keynote sales speaker. He’s a bestselling author, and he is the head Poobah at Tony Morris International. He’s coming to us today from London, England. Tony, my friend, welcome to the show, sir.

Tony Morris: Why, thank you for having me, and what a wonderful introduction and love the story, my friend, love it. Thank you for having me.

Darryl Praill: You know, it’s all about storytelling. If you’re going to be good in sales or good in marketing, you got to be able to tell stories, retell stories, make up stories, but it’s got to be about stories. Now, Tony, I’ve watched you from afar. I’ve admired your work. You got some great content out there. I mentioned that he’s a bestselling author. You know, some of his books you’d love. “Coffee’s for Closers.” You know, it sounds awesome, and it is the best real-life sales book you’ll ever read. There’s a positioning statement for you. You can find all of that on Tony’s website, which is tonymorrisinternational.com. So please check them out. Of course, he’s on Twitter. Of course, he’s on LinkedIn. Follow him. Tony, I know you have a particular presentation you give on a semi-regular basis when you’re either public speaking or you’ve been engaged by clients. And if I recall you refer to this, which is why I sought you out today, the three-letter word that will catapult your sales performance. And of course, I don’t wanna give it all away, kids, but you may have noticed my preamble. I used the word ask a lot. So, Tony, you are my ask expert. Not to be confused with Tony, you are an ass — just to be clear. Those are very different things. Okay. Talk to me about why this is a topic you’re so passionate about. Just like why this topic?

Tony Morris: Yeah, no, no good, good question. I was actually talking to my wife a few weeks ago, and I said, “You know, I’ve been in sales for one years.” And I said to her, “What is my super power?” And you know, we were sort of debating, and she said, “You know what it is.” She believes maybe why I’ve had some success in the game of sales is I’m not afraid to ask. And this is not just in sales. This is in life in general. We started having a bit of a laugh about this. I remember it was 2012, you know, a year after 9/11, I was celebrating my birthday and my birthday is on the 12th of September. My wife flew us out as a surprise to New York. And we were in Madison Square Gardens. We had a three-day break, and it was the end of day two. And my wife was desperate to go see a show on Broadway. You know, it was like a dream of hers. And we cued up in Madison Square Garden. It was like a four-and-a-half-hour, five-hour queue. And she was devastated cause we just weren’t going to get to see a show. 

Tony Morris: And I said, “Why don’t I ask the guy at the front if we can push in?” And she said, “You can’t do that.” I said, “Of course you can.” And I went up to the guy at the front, and I said to him, “Hi there. I’m sorry to bother you, but I’ve got a big favor to ask.” I said, “We’re on vacation, it’s our 10-year wedding anniversary, and my wife is desperate to see the show.” And I said, “Would you mind if I just stood in front of you to get tickets?” And he said, “My friend, be my guest”. And I stood in front, and I got two tickets for the show. And my wife was sitting there, bright red face. Like didn’t even want to associate herself with me and said, “How can you do that?” And I said, “Because we had a goal, and I explained to this kind gentlemen what my outcome was, and I asked the question. And I got an answer that I wanted to hear.” And the truth is Darryl, when I look at the simplicity of that, I look up why do salespeople not do what I did? And I think it comes down to two things. They don’t have the cajones to ask, and a professional term is they don’t have the will, but equally, they don’t have the skill. 

Tony Morris: And I believe when I look at the top salespeople I’ve ever had the pleasure to work with, and I know they’ve all been on your show. You know, Jeb Blount, Anthony Iannarino, Vic Antonio, and the list goes on. Something that they have innate in them is they ask questions. They’re not scared of asking for the business. They’re not scared of asking for the appointment, asking for the referral, asking the questions that will uncover the biggest challenges of our prospects. And I think it comes down to those two things. Salespeople in general that I work with don’t have the will, but they also have the skill to ask the right way. And I don’t just think this is a sales thing. I think this is a life skill that if we can learn from as young as possible of how to ask the question and how to ask it the right way. I think that is the recipe for huge success in sales. So to answer your question, that is why it’s my absolute passion, and that’s why I travel around the world teaching people how to ask. You know, overcoming the barrier to ask and how to ask it the right way.

Darryl Praill: It’s so interesting to hear you frame it that way, Tony, because, I mean, you said a couple of things that I alluded to and everybody, if you don’t know already, this show is 100% not scripted. These are live conversations, and you can probably tell because some episodes are certainly better than other episodes. So you made the comment about you just ask the question, right? You just, and it was, you also said, you asked it, you said you had the cajones to ask it, and I’m gonna circle back to that. But you also said, it’s how you asked it, right? Which is the point I was making on my story at the end there. I could have asked some really blunt questions and turn them off, or I could have asked them very leading questions, some soft questions. I could build, instead of going, wanting the answer I want, like in one question, I could ask three, four, five questions to get there and build their trust and build their engagement. Cause what we know is that the more they talk, the more they respond to you, ironically, the more they open up. It’s like, they’re building a relationship with you. They’re building trust with you, and you spoke to that, but I want to circle back to your point about having the cajones cause I really liked that point. 

Let’s talk about mindset

Darryl Praill: My wife, full disclosure, those who know her or have seen her on the video or heard me talk about her on the show, she’s not a salesperson. She’s an interior designer. And she has said to me many times over the years, she’s like, “I don’t know how you do it. I just don’t know how you do it.” And I said, “It’s your mindset.” I wanted to ask you about mindset. I’m gonna get to that in a second. I said, “It’s your mindset.” In my opinion, it’s your mindset. My mindset is, assuming I asked the question tactfully and contextually so it’s not from left field, what’s the worst that could happen? The absolute worst that can happen, 99% of the time, is you’re gonna have somebody say, “Oh, I’d rather not answer that. Oh, I understand why you’re asking that, but no, I can’t answer that.” Or, “Nice try, Darryl, I’m not giving that away. It’s gonna affect my negotiation skills.” Whatever. In other words, the worst that can happen for 99% of the time is you just don’t get an answer. And most people understand why you’re asking questions too. They understand that there’s a point to this conversation and that 1% of the time, maybe they’ll say, “Praill, let’s sit, this call’s over.” Okay. Again, mindset. The call’s over, fine. Did you blow it? Maybe. Lessons learned. Or maybe what they just did is ended the call, thereby freeing you up to start the next call, and that call could be the deal that you close. 

Darryl Praill: Mindset doesn’t focus on the failures. It focuses on the opportunity. Asking a question is an opportunity to get information. If they hang up on you, that’s an opportunity to get another deal somewhere else. And that’s the mindset. So I want to talk to you about mindset. But before I do that, Tony, I have to go to commercial break. I apologize. So kids, don’t go anywhere. We will be right back, stay tuned. Okay, so before the break, I asked you about mindset. I brought it up. That’s my thought process. My question is, I’m going to ask you point-blank, and maybe it’s not mindset, maybe it is mindset. But my question is this. Notice guys, I’m asking a question. Tony, how do you change the mindset of why people won’t, don’t, can’t, shan’t, choose not to ask?

Tony Morris: I believe from the questions I’ve asked of people of why didn’t you ask, that the responses are pretty common. They say, “I’m scared to get a no. Yeah, I don’t want to be rejected. I’m embarrassed. I don’t want to appear desperate.” And these are all internal roadblocks that they’re having. And, to a degree, limiting beliefs. But I remember my late father, bless him, the best advice he ever gave me in sales. And you’ve heard it before Darryl, and I know your listeners would have heard it, but that doesn’t mean they action it, which is, if you don’t ask, you don’t get. And that is so simple, but we know people don’t do it for the reasons I’ve just said. So the way I coach it and change the mindset is this, you know, you’ve gotta be open in sales. I believe if you want to improve, you want to learn, grow, and develop. You gotta be receptive, and you gotta be vulnerable. And therefore, the way I see it, and it was something Nelson Mandela once said. Mandela said, “You never lose.” He said, “You win, and you learn.” And what do they take from that in the sales world is if I ask a question, and I ask the question the way I believe will get me success. If it doesn’t, I’m always looking for that lesson. I always wanna know where is the lesson? What can I gain from that that’s gonna serve me better? 

Tony Morris: So when I understood that it changed my mindset because I’m gonna ask the question to achieve the outcome I want. But if I don’t get the desired outcome, I win anyway, because I’m gonna learn from it and take that experience. And if I go back to my example in New York, I used a technique that I learned from a great book. And I dunno, Darryl, if you’ve come across this, but there’s a book called “Influence”, Robert Cialdini, and Cialdini spoke about clients’ offices. And he said, when he measured this, he said, if you justify why you’re asking for something, you’re more likely to get the outcome you want. So it was a technique, a method that I was aware of. So if I said to the guy at the front of that queue can I come in front, he’d have probably punched me in the face, and I’d deserve a punch. But if I explain to him, like I did, that it was genuine. It was my anniversary. It was my wife’s dream. Could I possibly come in front? Then I justified it, and he was a kind guy, and let me in the front of the queue, you know? And I bought him a beer to say, thank you. And that’s the point. So I think it is a mindset thing. You’re absolutely right. But it’s more about the negative stuff that salespeople are thinking of themselves that’s stopping them asking the question.

Darryl Praill: Okay, so brilliant advice there that Tony’s just given us, and he’s framed it so much better than I did. You know, I talked about what’s the worst thing that could happen, but what Tony said was you don’t lose. You learn. Well, who doesn’t want to learn? I mean, candidly, I think you might come to this podcast cause you just think I’m a handsome devil, and you want to hear my voice. Well, that’s a percentage of the audience, but the vast majority come here to learn. So you, my friend, listening to this episode are of the mindset you want to learn. So I’m asking you if this is you, you don’t ask those questions to extend that, give yourself the grace to ask those questions. They say the best way to overcome a fear, maybe I’m afraid of snakes, or maybe I’m afraid of crowded places, and you know, I can’t speak to this, I don’t have a lot of those kinds of fears, but they say it’s just repetitive exposure. And over time, you learn to manage and handle it. The same is true with asking a question. Many of you are gonna go, “I’m just 23, 24, 25 years old. I can’t ask you, Darryl, who’s 50 and who looks 30, but you’re 50, a question because the disrespect there, and I’m going to look like a fool. I’m gonna look like I don’t know. What if I ask something that you’re just gonna roll your eyes to and say, ‘I can never buy from him.'” 

Darryl Praill: Okay. Let me give you permission. We don’t think that way. If they do think that way, you never wanted them as a customer anyway. So fire their sorry ass. They’re not firing you; you’re firing them. All right? Ask the question. Please, for the love of God, ask the question. Give yourself permission to ask the question and do it enough times, and it gets easier and easier. Okay, so Tony, we talked about asking them to ask the question, but maybe they’re afraid as you mentioned, or maybe they’re not. Maybe they’re doing it already, but they’re doing it wrong. So let me go down this road. I wanna know both sides of the coin. What’s the right way and what’s the wrong way to ask a question. Or, even go beyond that, what types of questions should I be asking? Give me the crib sheet. Tony. Over to you, man.

Tony Morris: Excellent. So I think that there’s different types of questioning techniques, right? But ultimately, you need to understand what are you hoping to achieve from the question? So, for example, whenever I get an inquiry where someone’s looking to book me for sales training, one of the things I want is to understand what’s important to the prospect, what they’re gonna base their decision on. I wanna know who are my competition that they’re speaking with? And really I want to know what feedback they have on my competition. So there’s quite a lot of stuff I want to get out, and I might not have the opportunity or the time to ask loads of questions to get all of that out. So what I want to do is come up with what I call a killer question, that in my experience, the better the question you ask, the more likely you are to get the right outcome. And I would frame it with a really good open question like this: “Can I ask, Darryl, what’s the best advice you’ve had so far from the training companies that you’ve spoken to about your problem.” 

Darryl Praill: That’s a great question.

Tony Morris: And what that does, the reason I ask it, just to explain, is it tells me a lot. It tells me who they’ve spoken to, what advice they’ve taken so far, but more importantly, what they considered to be the best advice.

The best questions to ask in sales

Darryl Praill: Yeah, that last point really resonated with me, what they consider to be good advice. I express it a little differently, but it’s the same, same sentiment. I express it as it tells me what they prioritize as important to them. Right? We know you have all of these, your product, your service has all these capabilities and offerings, but when they respond, they said, “Well, the best one really hit marks A, B, and C.” Okay, of my laundry list of what I can do, A, B and C resonated with this prospect. That’s gold. That’s a discovery question. And we’re not even seeing there. This is just asking questions. You’ve got them on the phone, whatever it might be. Okay. So, in a nutshell, then, the right way to ask a question is what is open-ended, closed-ended, leading. Give me the secret formula.

Tony Morris: Yeah, again, it depends on what you want to achieve. If you’re looking for feedback and the only way to get feedback, it has to be open. You have to give the opportunity for the prospect or client to open up and talk, hence, an open question. So it really depends on your desired outcome. And only then can you work out the right question to ask. So, as an example, again, if I get an inquiry, I wanna know who the decision-makers are. So a bad way to ask would be, and I’ve done this before. I was speaking to a managing director who made an inquiry. And I said, Brad, as the MD, I take it, you’re the decision-maker. And he said, “Absolutely, I am.” And I remember I drove three-and-a-half hours to meet with him. We had a fantastic hour-and-a-half meeting. 

Tony Morris: And then when I went to close at the end of the meeting, said, “Look, what dates would you like to book me?” He said, “Tony, hang on. This has been a really good meeting, but I’ve got to run it past my business partner who’s the FD.” And I said, “Oh, okay.” I got that guy’s details, and your meeting was finished. And I sat in the car beating myself up, thinking, why didn’t this guy tell me he had a business partner? Whose fault was that? Mine. I asked the wrong question. Had I have said, “Brad, aside from yourself, who else will be involved in this decision?” He’d have told me about his business partner, Richard, and I’d have made a really good justification statement to get in front of both Brad and Richard, and it should have been able to seal the deal in my one visit. So the key is it’s about asking the right type of question based on the outcome that you desire. And most salespeople, I believe, me included, get that wrong.

Darryl Praill: I want to go one step further only because I saw this the other day written online by another individual — clearly not Tony Morris, but Tony Morris is something, this is what he would say. And what I liked about it cause he’s a savvy cat, what I liked about it was the whole question about open-ended versus closed-ended. And Tony just talked about why you use open-ended if you really want them to expound on it and to really, you know, give you lots of areas that you can pick and choose where you want to explore. Now they give you a lot. For example, his question is to know what attributes did the best sales trainers have that intrigued you? Well, they offered A, B and C. Okay, now I can choose to explore all three of those or two of those or one of those, whatever I wanna do. It’s up to me, open-ended. 

Darryl Praill: But the conversation comes up, and you always hear people say, never use a closed-ended question, but I’d love this comment this individual said. He goes, “If you know, the call is not qualified, you’re having a hard time shutting ’em down. Or they’re taking forever, they’re very verbose on the phone, and you’ve already got what you needed out of them. The best way to set a conversation down quickly is with closed-ended questions.” So am I asking a yes, no, uh-huh, whatever, mm-mm, answer question that can be answered that way. There is no storytelling. There is no long winded-answers, and you can quickly use a series of closed-ended questions to wrap things up and move things on to continue the deal for the next call — total sidebar.  

How engaging are you?

Darryl Praill: Okay. I want to talk to you about it. I see this a lot. People can ask the question, but they’re not engaging when they do it. So, I mean, do you see that? And you know, you can ask me the longest question. For example, “Yeah, Mr. Praill, um, I’m, uh, I was wondering if you had, um, to pick a…” Shoot me now! You know, just ask the damn question, be engaging. All right. So, talk to me about how they can not just ask the questions, but they can be engaging with those asking the questions, such that the engagement level, just necessitates an engaging response back.

Tony Morris: Totally, and I think there’s a couple of ways. You’ve gotta be thought-provoking. So again, if I look at my business, often, I’d be in a meeting with a sales director MD, and I would say, “What are you looking to achieve from my sales training?” And often the response, 99% of the time, would be to get more sales. And I just thought, that’s accurate because everyone says that. And that can’t be the only goal. And I realized I was asking the wrong question, and I wasn’t engaging the prospect’s brain to give me the real answer. So that’s when I used what’s called a future pace question. And I said to the sales director or MD, “Imagine we fast forward three months from today. How do you know my training has been a success?” 

Tony Morris: And what was fascinating is it gave me so many different responses. I used to say things like, “Mike, the morale in my office has gone through the roof; the team are buzzing.” Or “The level of call activities gone crazy there. They’re making three times the amount of calls they’ve ever made.” Or “Our conversion rates have doubled.” Or “Our cost per lead has reduced by 25%.” And now, I’m understanding the real motives. And the way to do that, the way to engage better is to ask better, more intelligent, thought-provoking questions. And I see this in every industry. I do a lot in the real estate market, and the sort of questions that they ask their buyers are things like, “Have you been looking for a property long?” Closed question. And the buyer will go, “Yeah, I’ve been looking for a good few weeks.” And then they’ll go, “Have you seen anything that you liked?” No, which is why I’m speaking to you, you numpty! It’s just questions, right? So then I said to this agent, “Be creative, get them talking.” And then they come up with a killer question: “What’s the best you’ve seen so far?” And that just cuts through the noise, right? It’s good to know you’ve been looking for three weeks. It’s good to see, no, you’ve seen 17 you’ve disqualified. All want to know about the bungalow, the grade two listed bungalow that your wife loved, but you just didn’t love it. I want to know about that house. So if I ask a killer question, I will always engage you more and get out much better information.

Darryl Praill: There you have it, folks. The three-letter word is going to catapult your sales performance is the word, ask, A-S-K. It feels like that needs an acronym. We’ll work on that. In the meantime, I’m Darryl Praill. This is the “INSIDE… Inside Sales” show, and you’ve been listening to my good friend, Tony Morris. Check him out, Tony Morris International. Tony, thank you so much for joining us today. Please, folks, follow him on LinkedIn. Follow him on Twitter. And if you get a chance, give us a positive review on SpotifyApple, whatever. We’d be grateful. We hope you enjoyed today’s show. We hope to see you back soon. I’ll talk to ya.

Tony Morris: Thanks.

Darryl Praill: Take care. Bye-bye.