EP - 056

Leave No Room for a No

With Mark Drager

Master the art of pitching and transform doubts into deals

The How To Sell More Podcast


February 23, 2024

In this episode of “How to Sell More,” host Mark Drager gets personal. Using a story about his 15-year-old son’s plea for privacy, Mark demonstrates some sure-fire strategies for creating the “perfect” pitch, one that removes all of a prospect’s doubts and uncertainties so they have no choice but to move forward with you.

Clarity and Rationale - When making a request, be clear about what is being asked and provide a rationale for why it's needed. Explain the benefits and the necessity of the request to the decision-maker.

Personalized Approach - Tailor the pitch to your prospect's concerns and interests. Understanding what matters to them and how your request aligns with their values or goals can significantly impact the outcome.

Consistent Follow-up - Demonstrate consistency in your actions and follow up on any commitments made during the pitch. This reinforces your credibility and trust and increases the chances of achieving a positive outcome.

“When we’re trying to influence someone, we can't underestimate what it really takes to be able to remove risk and make things predictable.” -- Mark Drager

Links to This Episode

Key Takeaways

  • Anticipate and Address Objections - Before presenting a request, consider potential objections and address them proactively. This preparation helps remove any doubts or uncertainties and makes it easier for the decision-maker to say yes.
  • Engage with Questions - Encourage dialogue by asking questions to understand concerns or resistance points. This approach not only gathers valuable information but also involves the prospect in finding a mutually beneficial solution.
  • Mentorship and Guidance - Learning from others who have experience in successfully making requests or pitches provides invaluable insights and shortcuts to learning effective strategies.

Top 3 Reasons to Listen

  • What Mark Learned: Discover how teaching his son to create a compelling argument that removed all of his reservations, helped Mark break down some of the necessary ingredients for the perfect pitch.
  • Strategies for Success: One of the best ways to document and present solutions is to write down the request in a structured format. It not only helps you to organize your thoughts and present a coherent argument, but it also demonstrates the time and consideration you’ve given the matter.
  • How to Get More of What You Want:  If you can figure out how to approach people, how to pitch your ideas, and how to ask for things in a way that takes away a lot of uncertainty and the reasons that they might say no, you'll get a lot more of what you need.

More About our Host, Mark Drager

AKA the Badass Brand Architect, 5th Generation Entrepreneur, Host of The How To Sell More Podcast

When he's not podcasting, Mark's the Co-Founder & CEO of SalesLoop. He's a dedicated husband to his high school sweetheart, Jacqueline, and a proud father of four.

Mark didn't follow the typical route to becoming a sales & marketing expert. A connected figure in the entrepreneur community, Mark provides listeners with a unique mix of wit, insight, and straightforward advice.

Some of Mark's unconventional adventures include commandeering a Boeing 737-800 for a day, facing harsh criticism from a billionaire, and shedding 70 lbs in his late 30s. Though he never attended college, Mark stands as proof of the

A Transcription of The Talk

Mark Drager: Welcome to "How to Sell More." In today's episode, I'm talking about the pitch—how to perfect the pitch, get more people to say yes, take away all the doubts and uncertainties, and all of other people's nos. So that way, they have no choice but to move forward with you. I'm going to share a personal story about how and why I thought of this for this episode. We're going to get into all that and a whole lot more. I am Mark Drager; let's get into it.

So, in a recent episode of the podcast, when I was talking about the Beatles, I mentioned this line: never underestimate what it takes to sell. And I heard that in a mastermind group, I was a part of, and I'm not sure who said it originally, but never underestimate what it actually takes to sell something, to sell someone on a concept, on an idea. Because as soon as you start to sell someone on it—and I'm not trying to get into the weeds here about "never be selling," or I'm not even talking about that—when you're trying to influence someone, when you're trying to make an impact on them, when you're trying to convince them of something, or motivate them, or influence them, or sell them something, we can't underestimate what it really takes to be able to remove risk, to be able to remove uncertainty and make things really, really predictable. And to be able to help people part with dollars, which is one of the most challenging things. And the reason why I'm talking about this is because, for any kind of longer-time listeners, you know that I have four kids.

And so, my wife and I are high school sweethearts; we got married—gosh, what, 18, 19 years ago? This year, it'll be 19 years since we got married. And we have four kids. And so, my oldest son, my 15-year-old Jonah, is an incredibly smart kid. But at the same time, not necessarily the most consistent. I mean, what would you expect from a 15-year-old boy? But, you know, as someone who has a lot of ideas going on and tends to be a little bit hyperactive. And not the most consistent means that we find ourselves repeating ourselves a lot. We find ourselves asking him to do things, and then he forgets to do them. And he's just not been the most consistent when it comes to, you know, just things around the house. So I'm not going to get too much into it because it's, you know, he's 15 and his side, but here's what's really interesting.

We have this rule in our house where our kids are not really allowed to have access to screens anywhere that's private. And you know, with a 17-year-old daughter and a 15-year-old son and a 12-year-old son and a 10-year-old, we try to keep things out in the kind of common areas as much as possible. And so when COVID hit, and we found ourselves with all of these offices—I had 3000 square feet of space, I had space for 26 staff members. And frankly, we were all working remotely; we closed our offices. I brought all of the desks into storage, but I brought some of them home. And so because the kids were doing remote schooling, and we were all home, in our common area, they each had their own desk. They have their own little corporate desk setup with their screens, and it's kind of in a common room. And, you know, my son has been there playing games and recording videos and doing all of the things that teenage boys do, but he wants to be a YouTuber, and he wants to be able to do this stuff. And there's just too much noise. And so he has been asking for a very long time, for well over a year, if he could move his computer and he can move his desk to his room. And frankly, you know, we would start to lose control. I mean, for a kid who does not tend to go to bed on time, who tends to be very tired when we wake him up in the morning, who is kind of inconsistent with getting his chores done—like the last thing we want to do as parents is then say, "Sure, go ahead and have unlimited screen time in your room where you can't hear us, where you can't see us, and frankly, where we have no idea what's going on." I don't know about where you are from a parent's point of view, but that's how we feel. And those are our values, and those are our rules. But he has been asking for a very long time to have his computer and his desk down in his room so he can do recordings.

So, we can podcast, we can do a bunch of creative things. And over Christmas, he said, "I, you know, I've been asking for a year. When can this happen?" We said, "Well, I don't know, Jonah, like there are some things we're concerned with. We're concerned with, you know, your food intake because he takes medication that keeps him very lean. We're concerned with your sleep, because again, he takes medication that makes it hard for him to fall asleep, and he gets insomnia. We're concerned with, you know, inappropriate content and privacy and a whole bunch of things." We gave him the things we were concerned with. And we told him he needed to do better.

And he came back a few days later and he said, "Better at what?" and we said, "Well, we got really specific with what we felt he needs to do better at." And a month later, he comes back to us and he goes, "I've been doing this for a month now. Can I, can I go ahead and move my desk down?" We're like, "Whoa, hold on, hold on. You sure it's been a month?" and yes, I have seen some ways that you've gotten better, but I don't think you've actually gotten better. And he was really upset. He felt that was unfair.

Now, what does this have to do with selling more? What does this have to do with pitching? I'm going to get to that in a minute. But Jonah felt that it was unfair, because he wasn't quite sure what he had to do. He felt that he was doing better. But we didn't think we were seeing that. And here's kind of the gap. And I tried to explain it to Jonah, "Listen, I don't need you to declare to me every time you take out the garbage. If you're taking out the garbage more consistently, and I'm not asking you to take it out, frankly, I'm not going to know that you're doing it because great work goes unrewarded. Great work is silent; great work doesn't need me to call them out all the time. But if I'm constantly having to say, 'Go to bed, and get off your screen, and we need you to take the puppy out, and why isn't the garbage done, and the recycling done? And have you vacuumed this, and have you made your bed?' and all the stuff that we have to bug him with all the time, when we're bugging him all the time, we notice it. But if we're only bugging him for some things, and not others, we're not going to notice it.

And so he got really upset. We said, "We don't think you can move your computer down." And he finally said, "Well, what do I have to do? I feel like I've been doing everything." And here's where it comes to the pitch. I said, "Jonah, you can't just ask us for something, you need to take all of the nos away from me. You have to create such a compelling argument that I have no reason, other than being unreasonable, to say yes to you. So, I want you to think about what you need to do." And then in the meeting, I made him set up a meeting with me and my wife, Jacqueline, his mother. And I said, "Okay, it was a Wednesday night, I said on Friday, we will meet. But on Friday, I need you to come back to me with a proposal, with a pitch. One, if you say for the last month, you've been getting better at all these things, what did you do? What were you doing? Like, I didn't see you getting better, but you may have been. So tell me, what have you changed? What have you learned? How have these changes been consistent? And what are you going to do to keep it consistent? That's number one. Number two, what are you asking for? Like, really? I know you want your computer downstairs. But what are you really asking for?

Let's be specific with this. Are you asking for unlimited screen time? Are you asking for it just to be down there? And are you going to have friends down there? You have a girlfriend; what are you really asking for? And then beyond that, my wife and I are both concerned that he's just doing what he needs to do to get what he wants. And as soon as we give it to him, he's going to backslide and change. Because we've seen this behavior, you know, in kids, right? Kids, but we've seen this behavior before: they'll do whatever they need to do to get what they want. And then afterwards, they just forget about it. So, I said, "John, I'm really concerned that this is the case. So, I need you to tell me what you are going to do to overcome my concerns?" Three things, right? What have you done? What have you learned? And how are you going to stay consistent in it? What are you really asking for? And let's define what you're really asking for. And number three, how are you going to address my concerns?

The reason why I realized this is such a great exercise is because it hit me that my son, at 15, is in high school, and those in college, and frankly, when I entered the workforce, no one really taught this stuff. When I first started working at an internet marketing franchise, I had a very good relationship with the CEO over time, but when I first got there, my department, was me, and the work I was expected to do, was under-resourced. We did not have the equipment that I thought we had. We did not have the software that we needed to actually get it done. The previous staff member, who I was replacing, actually just brought in pirated software. They just did whatever they had to do to make it work. But when I got there, I was like, "This is unacceptable." Like, that was a production department. We were making videos, and we're making stuff, and I go, "We don't have microphones, and we don't have cables, and we don't have batteries, and we don't have proper cameras, and we don't have access to tape. On the port side, we don't have software, we don't have licensed music." This is in 2005, 2006. There was a lot of stuff we didn't have.

So, my manager said, "Okay, put together a list of everything you need." And I gave it to my manager. I didn't realize my manager was going to end it to the CEO and say, "We now need to buy $13,000 in gear." And so the CEO, and I've only been there a few weeks, the CEO comes up to me, says, "Mark, can I talk to you?" "Sure." He calls me to the boardroom. I remember I remember sitting down—I'm 23—I remember, I remember sitting down there, I'm like 22 years old. And he said, "Mark, if you're going to ask for something, don't ask this way. If you're gonna ask for something, you can't just tell me what it is and what it costs. You need to explain to me why I should spend this money. What will it do for us?

And I didn't quite understand. I mean, I was a student, I was a brand new employee, I was working at this company, and no one had ever taught me how to pitch something, how to ask for something properly. And so I said, like, "What do you mean?" And he said, "Well, like this tripod here. Why do you need this tripod?" And it didn't make any sense to me. I was like, "Well, because the tripod we have is garbage, and I can't work with it. You know, why do we need to spend $1,200 on a tripod?" "Oh, okay. Well, it's going to allow me to do Baba Baba." And "Why do we need the software?" "Well, we don't have the software. The previous person was pirating it." The CEO didn't know that, really, the previous person was pirating. "We had pirated software in my company." "I didn't know that, oh gosh, okay, we better do it." And so he went point by point. But in that exercise, what I realized was I was asking for something. And I wasn't actually telling him what the ask was, and explaining the benefits and explaining why it was mandatory or necessary or a nice to have. I wasn't giving the CEO the information they needed to say, "Yes." I was just asking for something. No one really taught me that up to that point. And I realized I had never taught my son this up to this point. And maybe you're listening to this. Maybe you've learned the hard way, like me, or maybe someone's pulled you aside and mentored you, but maybe you've never learned how important this is.

And so when I was working with Jonah to basically say, "Hey, okay, put this together." And I said, "I need you to put it in writing, I need it to be in a bullet point document. And I need you to walk us through it." These were three key things: put it in writing, make it bullet point, and walk us through it. First, because he has a habit of just wanting to show up and just ramble talk and talk and talk and talk and then—and it's got to be in writing. I need it in writing because I want you to work through the exercise of thinking everything through. Again, if you recall, there were three things I asked him for. What have you done over the last month that's really been different? And what have you learned from it because I wasn't seeing the work? So show it to me. Two, what are you really asking for? And then three, what are you going to do to address our concerns?

Now, he said, "That's a good question. I don't know what your concerns are." What a great question.

"I don't know what your concerns are. So how can I address your concerns?" I said, "Jonah, why don't you ask me?" I said, "I will give you all of my concerns." And I met with my wife, and we put together a list. And we openly handed it to him. And I said, "Jonah, like, I'm going to tell you, I'm literally making this so easy for you. Here are the five things that we're worried about. Now you tell me why we shouldn't be worried about these five things." Right? I am doing for my son, for Jonah, what the CEO did for me: pulled me aside and said, "Listen, you've got to figure out how to ask for things better. Because if you just ask for it on face value, the immediate answer's like 'No, why should it be?'"

So Jonah puts this document together. And because I made them take two days, and I made him put it in writing, he came back and he thought of things and he asked things. And so he puts together a document. And he says, "Do you just want to read it?" I said, "Send it to us in advance. So that way we can review it and then walk us through it." And here's what was really amazing. When my wife took a look at it, because she didn't know I was asking for this. She didn't know any of the stuff was happening. When she took a look, she said, "This is a really thoughtful document." And I was like, "You know what? It is a thoughtful document." Jonah walked us through it. He walked us through everything he's done over the last month, and why he feels he deserves or has worked for the desk in his room. What the specific ask was, and addressing our five concerns, what he's going to do to make sure he doesn't backslide.

And then here's what it allowed me to do. It allowed me to say, "Okay, you have taken all of the negatives away from me, you've reduced the risk. You have removed all the uncertainty, we've made everything clear. But here's now what I can do, Jonah. If you're telling me you're going to be doing these things, if you don't, here's the punishment. So you better hold yourself accountable to these things because we now have them clear, we now have them in writing."

And then a few days later, he came up to me, he said, "You know, it's wintertime up here in Canada. Last year, in high school, he had two bikes stolen at this high school. He had one bike stripped for parts, and we had to deal with the police and all this stuff. And then we bought him a replacement bike. And then someone came along, they call them 'community members,' but basically, criminals came along and stole his replacement bike, and it's all on camera and everything. So anyway, he doesn't have a bike right now. It's wintertime; we agreed this happened in November, we agreed that we'd buy a new bike in the spring—again now a third bike in one year we're buying for this guy. And Jonah loves his bike, and he's really concerned; he takes care of his stuff."

And so, here's what's so amazing. There he goes, "You know, I'm thinking of pitching the principal." "You're thinking about pitching the principal? What are you talking about?" He said, "Well, because my bikes have been stolen. The vice principal knows me, out of the 1400 or 1500 students who go to the high school, the vice principal, I have a personal relationship with her, and she knows me. And she knows that my bike has been stolen twice. And she knows I have to keep dealing with this. So one, I feel like I have a relationship with her. So I could probably approach her and say, 'Hey, what can we do to make sure that my next bike doesn't get stolen?' First. Second, I thought that maybe I could keep it in a room with the teachers. And here's the rationale and reason why. And third," and he just goes on to this. And I could see that he took this structure off again, thinking, "What has he done? Or what's happened? Or what's the backstory? Or what's the rationale? What is the specific ask?"

"Now, if you can take it a step further to already do the like two or three possible solutions, which is what he's coming up with, 'Oh, I could keep it here with the student lounge. But here are some pros and cons. I could potentially do this over here. But here are some pros and cons.' But he is already thinking in terms of 'This is the backstory in that situation. Here is what I'm asking for here are the two or three possible solutions. Here's my recommendation for a solution.' And then I said, 'Jonah, you've got to take away all the nos, you've got to think through all of the reasons why they would say no to any of these suggestions, and you have to address them in advance. If you do that, any rational person has to say yes.

And so, this may not be the most tactical episode ever. And this may not be something that's like, super, like you're gonna just pick it up off the shelf, you can implement it right away. But I was amazed at this, two or three weeks of working with my son, Jonah, and how quickly he picked up on it. And frankly, I know that this is going to serve him for a very long time. Because if you can figure out how to approach people, how to pitch people, how to propose things, how to ask for things in a way that takes away a lot of uncertainty and a lot of risk. And frankly, the reasons that they might say no. Well, you're just gonna get a lot more of what you need, and a lot more of what you want. And we all want that, don't we?

So, are you like me? Do you feel like there's a proper way to approach any given ask to be able to get what you want? If you have extra tips, strategies, or things that I could be doing to get better at it or even maybe teach my staff and teach my sons, let me know. Head over to LinkedIn. Give me a search-up—a look-up. My name is Mark Drager. I am the black and white photo with the blue background. Drop me a DM and pass along any of those little secret tips that you may use. And while you're over there, why not drop me a connection request as well? I would love to connect with you. 

And with that, we will wrap up this episode of The How to Sell More podcast. I am Mark Drager, and I will catch you in the next episode.