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Non-Sleazy Selling That Works: Ian Ross on PYP 616
Episode 61611th February 2025 • The Plant Yourself Podcast • Dr Howie Jacobson
00:00:00 01:29:17

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Let's talk about persuasion!

Whether in the form of sales, or a helpful coaching conversation, or "street epistemology" for a cause you care about, it's very useful to understand how human beings make decisions.

Today's guest is Ian Ross, a sales trainer specializing in understanding human psychology and communication.

In our conversation, Ian debunks the common misconception that effective sales techniques are inherently sleazy. Instead, he argues, sales can be all about communicating effectively so that our conversation partner makes a good decision.

It's certainly possible to misuse powerful communication skills, as with any tool. (You should see the havoc I can wreak with a reciprocating saw.) And there is a fine line between influence and manipulation — ultimately, it's all about intent. 

After covering the basic principles of sales psychology, which apply to everyday interactions, we pivot into helping me become better at selling my own consulting and coaching services. 

Ian helps me create a process for the sales call, including the right and wrong questions to ask, how to deal with financial issues, and how to end the call with a decision — whether yes or no — rather than a vague and wriggly "I need to think about it."

Ian's wisdom is invaluable for anyone looking to improve their persuasion skills, in both professional and personal contexts.

Links

Vivid Selling on Instagram

Ian's Substack newsletter

Ian's Close More Sales podcast

Chris Voss on the Plant Yourself Podcast

Transcripts

Dr Howie Jacobson (:

Today, we're talking all about sales, which you might think is a strange topic for this podcast, but I have been in sales. It turns out my entire life, every time I've tried to persuade someone of an opinion, coach someone to change behavior, sell my services or sell products, help people. It's all about.

persuasion, and it's all about understanding how humans make decisions. So my guest, Ian Ross, is a sales trainer, salesperson, brilliant tactician and strategist, but also has a real deep understanding of human nature and how our brains process information. And a lot of this was challenging for me because a lot of what he said was things like, I don't want this to be true because I feel uncomfortable using

what I know to get people to change their minds, to get people to buy from me, to get people to make decisions that maybe I helped implant rather than giving them utter complete autonomy. So he talked me through a lot of this and we end up with me being coached on how to be a better salesperson of my own services. So that part may or may not be interesting to you, but the part all before that around

how humans make decisions and how we can help people become the heroes of their own journeys by becoming mentors to them rather than manipulating them be very useful. And you'll also learn how not to be manipulated if you kind of reverse engineer a lot of what you hear him saying. So I hope you enjoy. Let's get to it without further ado.

Dr Howie Jacobson (:

Ian Ross, welcome to the Plant Yourself podcast.

Ian Ross (:

Thank you so much for having me, Howie.

Dr Howie Jacobson (:

It is going to be fun. you are a sales guy. Which I don't know what kind of reactions you get when you say that in polite company. And I'm guessing they're all over the place.

Ian Ross (:

I am.

In polite company, I tend to get the same reaction, is, and they just kind of move on. So in Nick's company, it can be all over the place for sure. Yeah, especially, but most people don't, there's an inherent belief in most people, which is I understand why, which is that if you sell, it means you.

Dr Howie Jacobson (:

Ahahaha!

okay.

Ian Ross (:

if not outright lie, at least exaggerate or fabricate or push people to do something they don't want to do. And so they have this kind of like, they associate anyone who sells with sort of like the sleazy car salesman vibe who's like, no, this vehicle, this Honda is amazing. You need to get in it. It's pay no attention to the dent and that we cracked open and rolled back to the speedometer.

Dr Howie Jacobson (:

Yeah, so we're going to be talking about sales, but we're going to be talking much more broadly, I think, about the things that you and I are both interested in, which is humans and our behavior and how we think and how we can influence each other for the better.

Ian Ross (:

Yeah. And how I think this will relate to your audience, especially if they're like, well, I'm not in sales. How is this going to be relevant to me is that I'm not necessarily a sales guy, even though that's how I'm introduced and that's the lanes with which I swim. How I think about, how I think of myself is I'm a sales trainer who has a focus on understanding how humans make decisions, understanding psychology and communication and how to get someone to offer up,

a choice to take an action on something so that it was their idea. And fundamentally at the end of the day, the call to action tends to be a monetary exchange for something else. But the principles of what I'm training most salespeople on is just psychology. It's just influence. It's just persuasion. It's communication. So I think it will be relevant to your audience because if they communicate with other people, there are skills that I train people on professionally. Now they pay a lot for it because there's a direct ROI in terms of what they do on a day to day. But what I

actively teach is communication skills.

Dr Howie Jacobson (:

Right. So if someone's thinking, well, you I don't sell anything, but I'm trying to get my neighbors to vote in the next midterm or I want to, know, I want my local store to stop carrying products of animal cruelty or I want to convince, you know, my dad to cut back on red meat and wine because I'm worried about him whatever. Like those are all sales conversations, essentially.

Ian Ross (:

Yes, those are sales conversations. And I would say that what I train people on goes even deeper than that because how you talk to your spouse about whether or not they had a tough day, how you talk to your kids to instill values or get them to learn a lesson. Those are all just microcosms of communication. We're just not going into the next step of then trying to convince. So the situations you gave up, you brought up are very applicable because they involve a kind of like, want an outcome, which is what

how people think about sales. But most of what I train on is really just the communication skills, how to actively listen. I know you had Chris Voss on this podcast, how to listen to what someone's saying, how to be tactically empathetic to their situation, how to demonstrate that empathy in a way where they're offering more information, how they can feel heard and understood so that they're more open to your suggestion or not your suggestion. You don't necessarily have to make a suggestion, but.

people are more open to your suggestion if they feel heard and understood. what I train on, you can choose to stop at any point. It can simply be to have an amazing conversation with your spouse or partner so that they feel listened to. It doesn't have to be, and then once they feel listened to, I can then say, here's how I would make a suggestion for you, then now they're more receptive to it. Wherever you choose to apply the concepts that I train on and teach is entirely up to you. It doesn't have to involve convincing anyone. It's just the most

common comparison.

Dr Howie Jacobson (:

Right. And one of the things I'm going to enjoy about this conversation is, you know, I'm a coach and a coach trainer, and there's a lot of parallels in terms of how to make suggestions when you can kind of offer something and when it's interfering with someone else's autonomy or sense of their own status or self-esteem or whatever. But most of what I teach is what we would call via negativa, which is like things to stop doing. Right.

And I know what you offer are kind of much more advanced. Like once you stop doing those things, then the question is, like, what do you do? And I ask questions in a certain way. But I know that when we've talked in the past, you've kind of shown me like here's nuances. Here's ways to do it even more effectively to to build rapport and even a better way. That's kind of like, you know, 201 and 301 and graduate level.

Whereas a lot of my communication is just I just stopped saying stupid shit.

Ian Ross (:

Which now, to be clear, there's levels of like, what's the lower hanging fruit that gets you the better return on your actions. So stopping saying stupid stuff, stopping putting stupid stuff in your body, starting to move your body basically are all like the lowest couple rungs of the ladder. And if you're trying to like climb to the top echelon without mastering those lower rungs, you're probably making a mistake because like you get

It's a little bit like the 80 20 rule. 80 % of the return is in the basic stuff to just not do the bad things. But usually by the time I'm having a conversation and training someone, it's because they've already gotten past that point and they want that, that next level. I think there's incredible parallels between the right types of sales conversations and coaching because I don't even say I'm necessarily selling something, though. That's how the market thinks of what I do in terms of sales.

I think my job is to teach people how to get someone to want to take action and make it feel like it was their idea. That's the principle that I train on. Because I'm training multiple industries. I'm not just training sales. I'm also training people who are acquiring houses from people and getting people out of tough situations. Like loan officers. People who are loan officers for businesses, like to figure out an interest rate. There's all these nuances that isn't necessarily let me sell you a widget.

let me sell you this physical good, or let me sell you this course or product. It can simply be, how do I get someone to decide to take action based on a conversation and have the internal drive and wherewithal to feel like it was their decision? They weren't sold. They were just talked to and guided to making their own decision. And that is relevant to any human being who interacts with other human beings.

Dr Howie Jacobson (:

All right, so let's get into it. What did you learn about human beings that you needed to know before getting good at this?

Ian Ross (:

Ooh, I think this, that's a really good question. I think the most important thing to understand is that the, many, and so many who will get this wrong in sales in general, this is why people, this likes people is that, and you know, this is a coach very well, but sales people don't know this, which is that to inspire action in someone, make someone feel good about their decision to move forward, it has to feel like their idea. And the way to make it feel like their idea is that

The salesperson or the coach is not the hero. We are the guide, the person making the decision, the prospect, the client, the patient, the friend, they are the hero of their own journey. And so it's how to have a conversation, how to suggest an action where the person who has to take the initiative, the person you're talking to feels like the hero of their own story. Instead of like, let me be the brilliant coach who can tell you exactly what to do.

You've done this long enough, you know that doesn't work. People might nod and say, I'll definitely do it, but then they don't really do it because it didn't feel like their idea. To actually get them to do it and do it consistently, it has to feel like it comes from within and we're the guide in that process. We are not the hero.

Dr Howie Jacobson (:

Yeah, it reminds me of some British whift who said diplomacy is the art of letting someone else have your way.

Ian Ross (:

Exactly right. Yeah, it's that same idea, right? So it's like some of the stuff I train on and the more advanced level stuff. It's kind of like the movie inception and that like, how can I implant this idea in their mind? But it feels like it came from within and the which can feel incredibly manipulative if applied outside of the context of actually trying to help someone. But I always say like the difference between manipulation influences intent. No one thinks that

therapists are manipulative when they don't immediately say exactly what they're thinking about their patients. If they go, I'm going to hold back and ask a question instead of saying, you sound lazy and you're repeating yourself, right? Because it doesn't actually help. And a salesperson who does the same thing in society is often considered manipulative because like you weren't honest with them, but it's like, I was trying to guide you to make your own decision. knew there's ways to get you to feel like you want to take action on this. Assuming I'm selling a good thing or a good product and providing a

service that you actually want need that it comes from within for you. So that's like, that's the focus there. It's like, how do I make it your idea instead of I told you about it and you agree.

Dr Howie Jacobson (:

Yeah, now I've been on both sides of this because I was in marketing for many years. And one of the things that I was taught is if I'm writing, you know, sales copy about some product that I'm selling, especially if it's a little bit complicated, which everything that I do is complicated, don't start with the price. And so I would, know, and then people would ask me, how much is it? And then I would, you know, I had learned.

to say, well, I need to find out more about your needs before I can give you the price. Now, that wasn't always true, because sometimes I had a program that was, you know, it's two K a month. And yet I was still saying, well, let me find out more about your needs because and I find now when I'm on the other side and I'm reading a sales letter and it doesn't say what the price is, I'm pissed. Like, right. So how do how do I how do I stay in integrity knowing that there's

Ian Ross (:

Right.

Dr Howie Jacobson (:

There's a time if I if I start with the price and they don't understand what it is, that they might make a bad decision based on not understanding the value proposition, but also like not being manipulative and not lying and not trying to be tricksy.

Ian Ross (:

The most important thing for you to understand in that context, which I'm sure many other coaches who have been through sales, have been sold in the past and gone through marketing copy, like anyone who's on social media has probably clicked on things and had that type of experience. And so for the professional, for the coach, if you're trying to get someone to want to take action and you believe your thing is good and you think that you could help them, what you have to do is not try and put your brain in their bog.

in the nature of you, you're thinking I'm putting my brain and my awareness and knowing all the tactics in the, in the body of the person reading this letter. And they're going to be pissed if they don't see the price. Cause I would be pissed. Instead, you have to actually see the world through their eyes instead of trying to put your brain in their body and see their body through their eyes with your head. Like with your, your perceptions, your awareness, your knowledge. And the way to do that is to go, okay, even though I might not like this,

This actually across the broadest spectrum might be the way to get to help the most amount of people, assuming I have a good thing. So there can't like, I also don't like lying. So I don't like to say, let me ask you questions, depending on, depending on your answers. I'll give you the price unless that's true, which means I would always set up a thing so I can make that true so I can feel good. So I'm not lying. And I run a process that also works. So there's this weird balance of

making sure you are operating from integrity and believing in what you were saying and not being dishonest and not trying to obfuscate the reality of the process. But then also that is how the perception of the process gets someone to go, wow, I see the value first and now the price seems reasonable. Let me take action on that. You have to go like, they're not thinking the way I'm thinking. I am more educated on this process. I'm more educated on these tactics. I'm more educated on the way marketing works.

And so, but to assume that they will have the same level of resistance is actually hurting them because most of them won't and they would benefit from them trying to sell. So you have to actually see the world through their eyes instead of trying to imagine Howie Jacobson in their situation looking out.

Dr Howie Jacobson (:

Yeah, that's great. That's great. And so if they're the hero and I'm really respecting them and I'm not trying to manipulate them because my intent is good, does that mean that I have to be open to them selling me on something else? Like, yeah, this really isn't right for you. is something like that. Or I think you should talk to my competitor or my colleague.

Do I have to be open to that or do I just try harder to win?

Ian Ross (:

I would say it depends. Often you should be open to it because not everyone's going to be a fit for you. Like that's just a given. So being okay that not everyone would be a fit is one thing. The next level is also the differentiation. I say they're the hero, but we are the guide. And how I apply that is in, if you think of the hero's journey and you think of it in pop culture of the last hundred years, I think of Star Wars, right? Luke Skywalker is the hero.

Yoda and Obi-Wan are the guides, they're more powerful. They actually have more power, but the hero's journey, like I'm stepping aside so they can make the decision. Lord of the Rings, Gandalf is more powerful than Frodo, but like he's guiding him. So in that instance, it doesn't mean just because Frodo goes, I guess I'll just stay in the Shire, doesn't mean Gandalf doesn't guide him to his own journey. He's the guide, but it's the emotional idea is not that I'm the hero and you're tagging along, it's I'm the guy who goes, you can go down that path.

If you go down that path, might encounter orcs and trolls and all that. And maybe that will be good for you. Or you can take this idealic path here. The choice is up to you, but I want to make sure I can guide you towards what you will probably feel is the best thing for you. So you often have more authority, awareness, and understanding of the situation and the challenges that people you're talking to are going through. And it's our responsibility to guide them to be their own hero. So we have more power. We should point in the right direction. But internally, I don't want to think

I'm leading you to that direction. I'm just pointing out and letting you make the decision.

Dr Howie Jacobson (:

Hmm. So that that reminds me of one of the things I learned from my coaching teacher, Peter Bregman, says, I'm not working for you. I'm working for your future self, for future you like that's my that's my client. And there are times where I'm going to have to do things on behalf of future you that present you might not like.

Ian Ross (:

Yeah. Yes.

Part of the challenge for some of the people who would be the absolute best salespeople I can imagine is that they have a resistance to the uncomfortable question for people when they've just met them. And that is often the way to get someone that will actually want to take action. so understanding that I can kind of upset you a little bit in the moment in service of future you not present you is a really powerful mindset shift. And so

Dr Howie Jacobson (:

Can you give me an example?

How might I do that as a coach? Let's say I'm selling to an executive in a company who's they want to up their leadership game and I'm sensing that they're thinking it through in a spreadsheet sort of way. Is this worth it? I really like what would be an example of an uncomfortable question that could move things?

Ian Ross (:

Yeah, so I usually want to do is soften the way I would bring up that question. So I get permission almost through, you're familiar with Chris Foss, almost a type of accusation audit to get permission to go ahead. And then from there I would reframe, like ask permission to kind of reframe and sort of a yes, no basis, and then ask and open up the question so they could verbalize. That's what the flow would look like. So to give you an example in what you're saying, I might say, I'm noticing all these things you're telling me. I have kind of a tough question to ask you.

Dr Howie Jacobson (:

Mmm.

Ian Ross (:

And I

am not sure a right way I can ask you this without actually upsetting you. And I'm feeling it's gonna come off kind of aggressive to you. And you're gonna be like, how dare you ask me that question right now? But I feel like it's something I need to ask. And I leave that expectation so they, I'm not even saying, can I ask you the question? I feel like I need to ask this question. I leave this silence so they offer up, no, go ahead, what is it? There's a reason we're having this conversation. I trust you, I paid you, I'm interested. And so they've asked permission so they're much more receptive to it.

because I left the space and they offered it up. And then I would say something online, I feel like the way you're going through this is spreadsheet oriented and it's not actually people oriented. And that's costing you in ways you're not even aware of right now. Am I totally off base with that? Asking a yes, no question to get them to buy into it. if assuming they can go again, am I totally off base is a really powerful idea because it's not, am I in the ballpark? That's a yes oriented question. It's a no oriented question.

Dr Howie Jacobson (:

Mm.

Ian Ross (:

Totally off base. It's an extreme no oriented. So they're more likely to go. you're not I mean, maybe not totally or hadn't thought of it that way I guess kind of and then I can go can you tell me a little bit more about how maybe you've realized that or how so or kind of just mirroring and so then they start verbalizing in that thought trajectory and that way they start Talking themselves as the hero as to like what's that costing them how they're doing it. So I inserted a new

Idea gotten permission for it through so it's like awkward. have a tough question to ask Ask a tough question use an extreme no oriented statement to get them on board with like no not you're totally off base and then got open-ended either through mirroring a lock-on question so if they say like well, you're not Totally off base and I say when you say I'm not totally off base Could you tell me a little bit more what you mean? Like that's a lock-on question to pick a thing out and ask for more clarity or simply mirroring not totally and then they'll elaborate

Right, so like that's the idea in terms of getting people to introduce like a thing that is tough, but feels like it's in service of who they want to be.

Dr Howie Jacobson (:

Oh, this is good. I'm just thinking I just got this software that makes like one minute clips for social media, and I'm like, I want it to be like a five minute. I'm going to have to do that one manually because that's so useful. I you know, I love these the ideas and the principles. But honestly, one of the things that I really love about the way you work and teach and train is you give specific words like I can go home and I can practice that.

Ian Ross (:

Sure.

Yeah.

Mm-hmm.

Dr Howie Jacobson (:

You know, am I totally off base there?

Ian Ross (:

Yeah, because what's the reason I have to do that is because I'm a sales trainer. So they have to get an ROI. Like one of the things with coaches is that sometimes people can feel like they're learning, but they're not actively doing it because I'm training teams for companies. Like the team has to perform better to justify the cost of the business owner. So I have to come up with ways to make it immediately actionable for the people I'm talking to so they can apply it right after that call, not just think, wow, that's a new way to think about this.

I want to do that too, because that's also valuable depending on who I'm coaching. But if I can actually give you actionable things to go work on, then you can actually work on it and get the results. And then if I'm training someone's team, the team makes more money and the business owner wants to keep paying for the training. So by the very nature of doing sales trading, instead of sort of broader coaching, I have to play to an audience that needs it. I know you came from the marketing world, like a direct response ROI.

rather than the sensation of change or the feel like I'm making progress.

Dr Howie Jacobson (:

Right

now. So what that brings up for me is, OK, I can learn these phrases and words. They trip off your tongue because you're good at it and you've practiced for a long time and you have a you know, somatic container for it for me. So one of the things I did like four minutes ago when you mentioned Chris Voss, I was like, I need to quickly go to my podcast and find out what number that was so I can tell people to go listen to the Chris Voss episode.

And so I brought that up and you're in a square in the middle and down below, I see my copy about the Chris Voss interview. And I said three days after finishing the book, I used one tactic to save five hundred dollars on a new car. Now, that's a return on investment. What I didn't say then was that I should have saved a thousand. And the reason I didn't is I used the one thing and then I felt too bad about doing it again.

So if you're if you're giving me these these words, like there's a there's a level of comfort or discomfort that that people would feel when you know, OK, I'm going to learn to use this uncomfortable question. I could have the skill. I could have the knowledge, but still something inside me, some emotional learning makes it feel unsafe or makes me feel like I'm a fraud or that, you know, they're going to say I'm going to lose the sale.

Ian Ross (:

Yeah.

Yes.

Dr Howie Jacobson (:

And I know you're you're a huge fan of stoicism. And I'm wondering if those two things come together in terms of, you've trained me. I can do it in a simulation. But how do you help me be brave to do it in the world?

Ian Ross (:

Well, first is understand people have this misconception that because it's a soft skill of learning how to have a conversation with someone that it's knowledge you can just learn and then apply. But it's a soft skill in the same way as like you can watch all the instructional videos on how to play tennis. If you don't actually go out there and get the reps in with swinging the paddle, you won't actually make progress. And so the way I usually coach people is

to tell them to act like in your example, let's just say you were selling the car and you made 500 instead of say 500 in this example, I don't coach that very many, very many car salesman because I actually think car sales is set up in a bad way because they make more money when they screw over customers instead of helping them and I don't really like that. across in that example, let's just say instead of making an extra thousand, you make an extra 500. The way I would give you the instruction is to say the goal is to notice when you are

uncomfortable in asking the question. Like you feel it internally, like, I'm starting to get uncomfortable. And then go once you have that internal feeling, much like if you were working out, you do, you asked one more question, you do one more rep, right? And then you do that over time. And then when you feel uncomfortable is further along the line until you have no difficulty going as far as you want. So how it relates to how I think about stoicism is this idea of a commitment to the process.

Dr Howie Jacobson (:

Yeah, yeah.

Ian Ross (:

rather than the results. And if I just focus on the process and love the process, the results come. And that's very foreign for most people in sales, because most sales cultures are so focused on the result. They ring the gong when they get the sale, they celebrate the commission check, they do all that stuff. And I got good and made a lot more money than everyone else around me. When I didn't get focused on the results, I started focusing on the process. So how I would train you is go,

if you had that more than once, is that once you felt that in your chest, like, I'm uncomfortable, you go, I know that sensation. One more question about this now. One more technique when you feel that. And do that consistently over time, and then your baseline for when you feel that discomfort gets moved incrementally. And it gets moved way quicker than most people realize.

Dr Howie Jacobson (:

So at that moment, is there a way that I can sell myself on the next question?

Ian Ross (:

Do mean to ask it? Like to get yourself to ask it? Yeah.

Dr Howie Jacobson (:

Yeah, some way that, yeah, I

if I assume all these techniques could work, me talking to me, like in my head.

Ian Ross (:

Mm hmm. Yeah. So yes. So the way is just to believe you just have to believe me that much like when you're if you were lifting weights, the additional rep, the hypertrophy on the muscle is what causes the muscle growth. You just have to believe me that the discomfort in the soft skill is the exact same. And once you actually believe me, then you just have to go, I feel it. It's time to do one more. And it's not I have to keep going. I to go deeper. have to be more uncomfortable. It's I feel it.

The way to get out of this feeling is to ask one more. The way to finish this workout is to do one more rep. It's that type of approach. It's like, if you believe once I have that sensation, the way to alleviate this stress is to ask one more and then I can move on. That frees you up. Instead of going, that means I can stop. Just, you have to recognize that pattern in yourself and go, I feel that. I don't wanna ask another question. This is uncomfortable. The tactic makes me feel nervous. One more and then I'm done. And that is how you.

move the line in the trajectory of being as comfortable as you want to use as many questions, techniques, tactics, whatever you want to be able to make as much or save as much money as you'd like, or cause as much change in the people you're talking to really the way to think of it that way.

Dr Howie Jacobson (:

Gotcha.

Gotcha. So you'll appreciate where I learned that was when I first started training for an ultra and I had a 17 mile run on the books, which was about four miles longer than I had ever done. And at mile 15, I totally bonked. had nothing. And it's like, you know, so I'm two miles from my car. Like, you know, I told Geo, my running partner, like, let's walk. And he said, Howard, this two miles is the purpose of the whole run.

Ian Ross (:

Hmm.

Dr Howie Jacobson (:

That's why we did this.

Ian Ross (:

That's exactly right.

That's exactly, man, that is so true. So I think there's a lot of, I use workout examples for tough conversations because I think there's a lot of parallels. found incredible parallels in doing ultra endurance training in getting better at just about anything, right? It doesn't have to be sales. It's just, I like sales because the reason I'm kind of like a sales evangelist, which are well, people in your audience will be like,

Like what are you talking about? Is for me, especially if you believe in what you're selling, you're actually selling a good product, it's a really important thing. Okay. And you're at a culture that doesn't encourage lying and you're not incentivized to screw over your customer. As long as you're in that set up, there's plenty of companies like that, right? There really are. As long as you're in that set up, then sales is a perfect representation of personal development or personal improvement.

because as you get better, you see your bank account go up actually far quicker than as you eat healthier. see the body fat shed or as you lift weights, you see the muscles grow. It's actually faster return as I get better at these techniques and do more activity and pushing and comfortable. make more money in much quicker correlation than many other ways people get better. So to me, it's just another representation of that idea. Yeah.

Dr Howie Jacobson (:

Now, you say that, are you talking

specifically about commissioned salespeople or like anyone in a job? think if anyone in a job, like, you know, I think about the people who bag the groceries where I live. I don't know that they would make more money or a middle manager somewhere. But you're talking specifically about people who are commissioned salespeople, like get it.

Ian Ross (:

They're not in the sales role. No, no, no.

Yeah, maybe not commission, because sometimes it's commission, sometimes it's bonus, right? I differentiate that because it does matter. Sometimes you just have to have a certain number of sales and there's a bonus on it rather than actual commission for how much you sell. But yes, where you are paid more for having a better result, that's where it works. Not for any role. But I think it's a better equivalent in a sales role where you're incentivized to get better than even in business, because I coach a lot of entrepreneurs.

or coaches, coaches are just entrepreneurs, right? In the modern world, a coach, much like a standup comedian, is actually kind of an entrepreneur more than they are their actual thing, because they actually have to set up a business around doing their thing. And so if you are an entrepreneur, oftentimes, even as you get better, sometimes you'll make even less money, because now you're scaling, you're running a new ad, you're going to a new realm or a new, in front of a new audience, and so you actually have a drop-off.

Very rarely is there that level of adjustment in sales. Sure, there can be market corrections or you change jobs or something, but often your activity and how good you are at that activity, if you are paying a commission or a bonus for sales goes up as you get better. And that's why I think it's a great representation of choosing to get better and choosing to.

Dr Howie Jacobson (:

So that makes me rethink something, which is I know that there's a disproportionate number of CEOs of large companies who came up through sales as opposed to anything else. And my thought was, well, that's because they're bringing in the money. And so there's a bias towards them. But I think you might be saying that sales is more of a refiner's fire for leadership, for influence.

Ian Ross (:

So I think it can be, it depends the company, it depends why. Sometimes it might literally be because they brought in the money and then there's a bias. It might be. Because the difference between sales and leadership, now there's sales leadership and sales management. So oftentimes if they're coming up through leading a sales department, that works I think. But as an individual contributor, as the person who's having the conversation themselves, you can actually be far more sort of solipsistic.

and self-centered and focused and make more money than actually works in leadership positions. So it's not a direct correlation, but I think if you choose to use it as a vehicle for self-improvement the way I do, I do think there is a correlation there.

Dr Howie Jacobson (:

Because I was in a networking call this morning and the mentor who runs our group was saying one of the things he encourages us to do is to build a community. So for me as a coach, I don't really need a community. I can just go and get clients. But he's saying like build a community around your IP, around your spirit, because that will be a crash course in leadership development. And in this world, we all have to become leaders.

When you put on your total pure sales evangelist hat, what are the personal development benefits of becoming aggressively interested in improving your sales skills?

Ian Ross (:

because you have to understand how other people make decisions to improve your sales skills, which is absolutely leadership, right? And if you sell the right way, it's you helped people feel like it was their idea. There's that. have sales. The main reason people burn out at sales is burnout, right? Like the reason that people quit sales, I should say, is burnout. And the reason they burn out is because of what I, it's the sales roller coaster, meaning you feel like you're on top of the world when you've gotten a few sales. You have a great week.

You feel invincible. You're Tony Stark, you're Superman. Everything's amazing. And then the inverse of that is when you struggle, when you have droughts, you beat yourself up. You have all this negative self-talk and your self-worth struggles. Weathering that storm, having that level of resiliency to keep doing the process almost regardless of the results you are getting is an amazing tool in leadership.

because you will have droughts in your business. You will have droughts with your team. You will have struggles and triumphs and you will go up and down and great quarter, bad quarter and being able to be committed to doing the thing you know you need to do regardless of how you are feeling about the results you are getting is an incredible skill for a leader and you have to develop that to be good in sales.

Dr Howie Jacobson (:

Hmm. It sounds like it's a matter largely of identity and to what you to what you lend your identity outside of yourself. So if you're if you're lending your identity to your hit rate, to your net worth and to your you know, I was talking with a new friend yesterday comparing US and Spain in terms of in the US, if you're unemployed, a lot of people get very depressed beyond.

Ian Ross (:

Mm-hmm, sure.

Dr Howie Jacobson (:

Right.

Because it's like, who am I now? And in Spain, if you're unemployed, it's like, you know, whether you have a job or don't have a job, like that's that's not about you. You know, you got laid off. You know, it sucks. But it's not a personal failing or a, you know, some sort of, you know, judgment about about your your worth. I'm hearing I think I'm hearing you say that.

Ian Ross (:

Right.

Dr Howie Jacobson (:

To be good at sales, have to, again, if you're focusing on your process, on your inputs, bad outputs, bad outcomes can suck, but they don't mean that there's something, you know, fatally wrong with you.

Ian Ross (:

Exactly, right? Because it's an inevitability if you're in it long enough. It's just an inevitability. Like you can't sell everyone. It's impossible. Zig Ziglar, the famous self-improvement or the sales guy from the 20th century had this great quote, is that this sales person who says they can sell anything to anyone is not a sales person, they're a con man. Because what you have is not right for everyone. Like it doesn't make sense. There's nothing that's right for everyone. So you shouldn't sell everyone or you're

selling something bad, like there's no reason for that. So as a result, the identity of someone who is in pursuit of doing the process, regardless of the outcome is a really powerful mindset. And I've, I've used a lot of sort of stoic tools in terms of the traditional stoicism, not the like modern bro-icism, the way it's adopted in Silicon Valley and a lot of places that take a little, I just made that up. I, maybe someone else has said that, that was just me riffing.

like modern broicism of like how to how to just be self-centered and go to the outside world. I really like this idea of being in pursuit of improving the process and doing that through having great virtue and always caring about others more than yourself, but also to know to do that. You have to protect yourself to be able to be effective at doing that. Like I really apply those tools to be good at what I do and

Weathering the storm is a really key part of that because you will have ups and downs.

Dr Howie Jacobson (:

Yeah. Yeah, sorry.

Ian Ross (:

You also touched on, I'll get to touch on one more thing.

A big thing I train on is that, cause you pointed out the identity thing, which is that I train this all the time is that people will pay more for identity than utility. It's a huge thing. So even in the nature of getting good at sales, you understand that people will pay more to either stay congruent with their current identity or to be in pursuit of.

a higher or better identity for how they perceive it or how they view others perceive it. So there's a huge power in understanding of selling to someone's identity instead of the pure utility. It's the whole reason for luxury goods in the first place. A luxury watch is not about the utility of the watch. Obviously, we all know that. Everyone knows that. It's about the identity of someone who could afford that watch. It's a status symbol. It's a representation. And that exists all throughout

life. And so if you can tap into someone's identity as to being the type of person who's willing to invest in a coach, because you understand the value of progression and self change, and it's awesome that they have had this conversation with you, they are more excited and more aligned with wanting to do it rather than selling the pure utility of here's what I do as a coach.

Dr Howie Jacobson (:

guys.

Yeah, I hear that. believe it. And I'm going to tell you how unselfaware I am because I don't believe that's true of me. Right. And I know I'm lying. But like when I think of when I hear you say that, that really rings a lot of sort of manipulation bells in me. like, I'm going for, you Like.

Ian Ross (:

Okay.

Dr Howie Jacobson (:

vanity or self delusion or the need to belong like there's a lot of ways in which identity the need to have to to augment or present an identity is based in trauma, right, is based in lack. And so I'm thinking about when I first started doing Internet marketing, you know, I read this amazing sales letter about this training that I was going to go to and all the amazing things I were going to get.

And then we get there and it was a great training and I learned a ton. But one of the things I said was like, learn this marketers have to learn from the evangelists at tent revivals. Like you get everyone under the tent and then you do the ascension, which is to say to them, know, you know, like, like, you know, get rich overnight. Like now all of you in this room know there's no such thing as getting rich overnight. Right. And we're going to have to work hard.

Ian Ross (:

Right.

Dr Howie Jacobson (:

to end and you know, and you don't you're too smart to believe the hype. But it's the exact same hype that we sold them to get them in the room. And now we're kind of giving them a new identity. So when you say that identity sort of trumps utility, there's a way in which I get very uncomfortable with the way I've seen that play out in the world.

Ian Ross (:

Right.

Yeah. Oh, for sure. For sure. I'm calling out the reality that identity trumps utility. That doesn't mean the very nature that identity trumps utility means that people selling garbage will utilize that technique to sell garbage. Like all multi-level marketing is all about the identity of someone who has passive income, children with their family on the beach. it's Robert Cialdini's book, Influence. He didn't write to teach marketers. He talked to, so people will be aware of the marketing techniques that could be

they could protect themselves. And then marketers are like, my gosh, I can use all this to get people to do stuff. the fact that I'm calling that out, like I get why it makes you uneasy because you've seen it used for ill. There's the idea that's how the tool was used. I have no control. try and orient people to only sell for a thing that's helping people and not selling them garbage or manipulating them in a negative way.

But ultimately the tool that people pay more for identity than utility is absolutely true across the spectrum. In fact, even most people who feel like they prioritize utility, it's because they have an identity of someone who's better than other people because they prioritize utility. And like they want to reinforce that idea. So it's, it's, it's across the board. It's just a reality. It's how you use it has to do with intent. So just because you've seen it be used for ill and I'm really like, this feels terrible. Doesn't mean the technique hack.

Dr Howie Jacobson (:

Uh-huh.

Ian Ross (:

to be used that way, that was just the way they applied it.

Dr Howie Jacobson (:

Yeah. OK,

th,:

Ian Ross (:

Sure.

Dr Howie Jacobson (:

marginal tax rates, it's not it's about identity. It's a you know, and I would say it's a it's a it's a fight between fear, you know, with separation or belonging between like. But, know, and I think actually I think one side is doing a much better job of appealing to identity than the other.

Ian Ross (:

yeah.

That's, that's why they win. It's literally it's because they do a better job of appealing to the way people make decisions. Now you can use it for negative, like negative identity or protection from is a stronger impulse biologically than making things better. Right? So it often tends to without awareness and reality of what's going on using negative messaging.

tends to work better, right? There's this idea in the marketing space, which you will be very familiar with, which is very heavy on this, like, away from language and how to think about it. you need to lose 10 pounds so you can be the woman your husband still wanted to marry. And it's that type of thing. Rather than you can choose to get healthy, right? Like, a towards goal, away goals,

inspire action, but they don't inspire identity change and habit change. And so the coach is very different from marketing materials because the coach should orient towards, yeah.

Dr Howie Jacobson (:

Yeah, we have we have to be completely schizophrenic

about this because the because if I start coaching someone on the away negative goals, they're going to fail. But I have to sell them on the negative to get them in the door, right? So one of the things that one of the things I learned was when you're talking to someone, really extend the gap like where are they now? Where do they want to be? What where do they think they'll be if they don't do X, Y, Z and then kind of like rub salt in that wound?

Ian Ross (:

Yes, exactly. So.

Which is exactly right. Yeah.

Yeah, because if you believe in what you're selling, like if you believe in yourself as a coach, in this example, if you believe that if I had this person and they paid me the money that I could help, could I actually help them if I had the time and they showed up? If you believe in that, then I actually would argue you have a kind of, if you feel that way truly and you have the availability, you have almost a moral obligation to make sure they are sold so you can help them. And the way they are sold is orienting around the gap.

and the pain and when they're missing out on. And once they are in, because they've taken the commitment, because a financial exchange to sign up is a type of commitment, then we can shift the language to actually change the habits. it's the, you're reviewing it as schizophrenic, which I'm thinking is not under, I get why you feel that way. To me, it's not, it's there's what gets people in the door. And then once you're inside, how we can actually initiate change. And I just view them as separate steps in the process.

Rather than thinking I have to have the exact coherent message, because I've just seen too many times, that the coherent message of once someone's made a choice to commit is not what gets people through the door. And so I have to go, if I can help people once they're through the door, I have to do what works to get people through the door. Not lying, not manipulating, but do what works, which can be away from language, can be the gap and the pain for not taking action. And then once they're in, we switch up to actually help them and make positive change.

Dr Howie Jacobson (:

Yeah. So I want to say I feel like this requires tremendous self-awareness to do this, to do this, to do this ethically, to to adopt what you're saying. Like it's it's there's so many ways that I think in the past that I might have diluted myself around like why I was doing something.

Ian Ross (:

What does?

Dr Howie Jacobson (:

you know, was it really to help them or because I learned this thing to get them in the door? And, know, like one of my copywriting mentors was we spent two days at a conference learning how to write bullet points, right, to take like to look at the product and to turn it into first, you know, benefits, advantages, and then the bullet point. And he kept saying bullet, bullet, bullet's wound.

Ian Ross (:

Yeah.

Dr Howie Jacobson (:

You are trying to wound them with your bullets. I feel like I got so good at that that it was easy to forget that there are ways in which they wound, but they can also kill that that I could create such fear that the person could that they wouldn't get out of it, that there'd be that the whole interaction, that the whole relationship from that point on would be fear based or that I've re triggered some trauma or re injured.

Ian Ross (:

Yeah.

They true? Yeah.

Dr Howie Jacobson (:

their soul.

Ian Ross (:

It's certainly possible. mean, I, the main thing I am always telling everyone all the time, because I, I try not to have too much of a view of telling anyone this is how you should do something, right? Which is funny because like most of time I'm, doing that, but I try not to think like it's not my job to tell people how to their life, how to spend their days, what to eat, who to love, like how to exist in the world. That's not my job. The only thing I will.

Always every single time always repeat that you should do as Lisa's sales professional is have Intentionality behind why you are saying what you are saying or doing what you were doing There has to be intentionality you have to have awareness. Don't say a thing just because you saw it somewhere What's the goal of it and why and I do that for every I will always harp down like why did you say it that way? What was the goal? Like what what were you thinking what happened?

If you have intentionality, which is honestly a pretty good rule for your life, for what you put in your body, for why you decide to move, for how much you sleep. If you have intentionality behind your choices, your choices will be way, way better. Is this a quote from Stoic Veloster Epictetus, which is like, if you want to be beautiful, make beautiful choices. Having intentionality behind every choice you make is the way to actually make a beautiful choice, to actually think about it. So.

It all comes down to actually questioning why you're doing something and believing that that question is worthy of exploring to really figure out the real reason. That's underlying stuff that I don't usually talk about in this messaging, because I'm trying to get people through the door. And then once they're through the door, that's when I help them with that. So like we even talked about, I don't usually broadcast this idea that first you actually have to have such incredible self-awareness and self-reflection.

Dr Howie Jacobson (:

you

Ian Ross (:

that you're thinking about everything you're doing, that's after. Usually I just say, you're missing out on money, right? Like that's the way to get people through the door.

Dr Howie Jacobson (:

Yeah, but you know what? But you know

what? If you're talking to coaches, you do have to lead with that because every coach is going to come to you going, sales is icky. I know I need to learn it. Like if you don't lead with, know, yes, you can use this for ill, but I teach you techniques and methods for using it for good. Like you you wouldn't sell me, you know, because I'm a great person. No, because I have an I have a self identity. Right.

Ian Ross (:

Okay.

Yeah, that's true.

Dr Howie Jacobson (:

as ethical.

Ian Ross (:

Yeah. Yeah. You have an

identity that you don't want to do that. Yeah. I, I, I think I will, I haven't really fully broached into the focusing on helping coaches, but I think it's a thing I definitely want to prioritize in the future. Cause it does also align with how I think about sales anyway, which is just help coaching people on how to get someone to want to take action and then how to have a consistent process to do that. Like, so one of the biggest mistakes that coaches will make, and I'll say this cause I'm, I'm

You've made this mistake and every single coach you know in the space has made the same mistake It which is that they view their sales call like a mini coaching session And they think if I just provide enough value and coach well enough now They'll sign up and want this for forever. They're actually making yeah, they're doing a trap. They're making a critical Critical mistake and as I do this all the time having sales car I have a sales conversation right after we're after after we're done

Dr Howie Jacobson (:

Right, it's a tryout.

Ian Ross (:

I have to hop on with someone and I have to give them some type of value, but it's not actually if I give them the value of say, paid me for my time to just coach them. There's a differentiation coaching before they paid because you've known when you give that value, they go, great, this is awesome. You think you just gave the value and then you never hear from them again or they, you do and they don't, they don't actually sign up because you made the mistake of giving them enough information that you created quite literally the word like sophomore, sophisticated moron.

You've given someone enough that they can now take action on it, but they're not actually need that. You know, they need more advice on it. They need to check in. need to see if it really works, but you gave enough value that they feel like, I can go do something now. I don't need to pay money, but you as a coach, no, you only, we just, that was the tip of the iceberg. There's so much more, but in their brain, they feel like they've got something actionable. They feel inspired. They can do something. The way to do it is to withhold information in a way.

that actually makes them want to sign up so you can actually help them. Because you know when you gave that person that sort of free session, that tryout, and then they didn't sign up, you know they're not better off than if they actually signed up and went through your whole process. You know that inherently, but I couldn't get them across the line. They couldn't help themselves. You ran a bad process to help them out. There's a way you can do it where it can feel uncomfortable at first because you have to, you want to give the extra piece of advice. That's how you are as a coach. That's how coaches are. It's all the reason you're attracted to this space.

is wanting to help people through conversation and see that reaction. You have to understand that to actually get that, you have to make yourself a little uncomfortable, which is strategically hold back certain pieces of information until after they've signed up and gotten through the door. So that they're committed enough for multiple sessions. And most coaches just are not doing that effectively. They either sell too sleazily. They'll say stuff like, I need this discount only if you sign up today, which rubs everyone the wrong way. They think that's creating scarcity.

ial, uh, just sign up now for:

Dr Howie Jacobson (:

my God.

Ian Ross (:

It's Buddhism, it's the middle way. You gotta find the middle balance between giving value and also strategically holding it back without rubbing people the wrong way so that they're inspired and also got value. And it's a delicate line and I would love to teach coaches that at scale. I'm very excited to that eventually, but right now I'm a little too busy with two under two and everything else I'm doing, but it's something I'm excited to do eventually.

Dr Howie Jacobson (:

Gotcha. So I want to have you choose your own adventure here. I am a coach and I'm not great at selling my coaching. option A, help me be better at selling my coaching. Option B, sell me on your sales training.

Ian Ross (:

Okay.

No, let's help you be better at selling, because that's a better, the reality is, especially probably with your audience, it's probably better selling my sales trading if I help you be better at selling your coaching. Anyway, because that's actually showing the product. So okay, yeah, we can do a little setup to help you be better at selling your coaching. When you said the my God, I want to incentivize action takers, I'm guessing you've seen that many times.

Dr Howie Jacobson (:

It worked

on me, actually, and I nearly the only reason it worked on me is that the coach whom I hired said the first month you get a complete money back guarantee if you don't like it. it kind of and I've been doing some form of a money back guarantee on just about everything. And I tell people that, know, I think you should do this. And of course, I'm biased. And the only way I protect myself against that bias is by.

Ian Ross (:

Okay, yeah.

Dr Howie Jacobson (:

giving you 100 % guarantee that if I'm wrong, that's kind of the way I've talked about it. But yeah, so I do not like false urgency.

Ian Ross (:

So.

Okay, so for you, what, let's say I was, to make you better at coaching, like what's your process, like let's say if you were to have that first conversation, what are you doing currently to determine if you can sign them up or not?

Dr Howie Jacobson (:

Mm-hmm.

Yeah. Yeah.

So well, mean, there's some degree of marketing that's preceded it, where ideally it's a referral. Or they've read a book, or they've been listening to me for 200 podcast episodes. And I'm on some sort of a credibility pedestal already. But regardless, I want to know, so you know,

Ian Ross (:

Mm-hmm.

Okay, yep, definitely, definitely the best.

Yeah.

Dr Howie Jacobson (:

Tell me about what's going on in your life right now that you would like help with. What are you looking to achieve? And then they'll say, and I'll say, OK, great. What's been getting in your way? What's been slowing you down? What's been stopping you? What are the obstacles? And we'll have a discussion. And I've gotten better at not telling them what to do. I still have the urge.

Ian Ross (:

Yeah.

Dr Howie Jacobson (:

So I would say I'm following a process, but I don't think I'm I don't have any of the nuances that you've talked about about the more sophisticated thing. And at the end, don't really I get very uncomfortable about any sort of commitment or ABC or call to action where it's like, OK, well, you know, great. Let me know what you think.

Right. And I turn into.

Ian Ross (:

Mm. my gosh, Howie,

you're killing me. That's that's the well, that's also the worst possible closing line I can imagine. it's literally the worst thing I can imagine. Okay. Yes. I mean, because that flow there to have the conversation is pretty good. I would probably start with some aspect of setting expectations.

Dr Howie Jacobson (:

So you're saying there's room for improvement?

Ian Ross (:

So they have a idea so like the goal of this is to like for me to ask you questions to Determine it if it makes sense for us to work together I'm obviously hoping it does based on what you tell me, but I have to ask you questions first through this I'll learn a little bit more about you your circumstances What you're currently doing what you feel is holding you back at the end of this I'll see it and we'll talk about if it makes sense for next steps If I don't think we're gonna be a good fit for whatever reason

Is it okay if I tell you no? Like that I don't think would be a good fit. Everyone's fine with that. And by the way, I tell people no all the time. Sometimes someone just says, I have no money. And then I won't even tell them the cost. Cause I go, my stuff is too expensive for you. I don't even want to talk to you. I don't want to waste your time. So I do this all the time. I have to make sure if I'm going to say this, it's cause I believe it. Don't just say this stuff and not really do it.

Dr Howie Jacobson (:

OK, so I want to

come in with another thing that happens a lot is that we get to that point way too late. Like I was saying, I don't want to lead with the price because we want to discuss value rather than just saying, it's 2K a month. And then we get to how much it is, and they're like, this was never going to happen.

Ian Ross (:

Okay.

Yeah.

Right. So that's, like to start, that's why I call it setting expectations. Most people have that at the end, but you just wasted both your time. Right. So I'd rather say, Hey, like if I think either you're the budget doesn't align or you don't think there's going to be value in what we're doing is okay. If I tell you, okay. At the same time, are you comfortable telling me? No, this is a really powerful stuff because we're most people know sales, the sales conversation, which is what you're having, even though you're doing this sort of trial coach is trying to orient towards a yes.

So I tell you right away, no is okay. Which you think is like, but this seems sleazy. It helps people if you do it right. You have the right tonality and the right intention. People feeling like no isn't okay means the conversation flows better because they're not in pursuit of a yes, they're in pursuit of a yes or a no. The only thing I tend not to want to hear is exactly how you ended, which is like, I want to think about it. Just because to me, I tell people,

I often say I'm a little too busy to do sort of like the constant follow-up game, which is true. It's not a made up thing. So as a result, if I hear, need to think it over. tend to take that as a no. Is that fair enough for you? Assuming that we're aligned on everything today. And they will, if they go, well, I have to talk to my sister or whatever, like, well, now I know. And so can expect, okay. So like we could, we can prepare for that at the end. So there's a different expectation, but I never want to hear. need to think about it.

Instead of no because then I waste my time falling off and no one no one likes that dance So I'm calling out the awkwardness of front so something like that Then your questions were pretty good as long as you don't actually tell them what to do At the end. I never want to say like in the questions, which want to make sure you're gathering. Okay

Dr Howie Jacobson (:

one more thing to interject.

So the process I learned was that after we go, what do you want, basically? What's stopping you? I'm supposed to do things like, and what would it mean to you to get that? And what would that mean? And what would that mean? yeah, that's good and it works. And I have felt uncomfortable doing like that feels manipulative.

Like it's almost it should be obvious and we don't even have to talk about it or it's not for it's it's it's not for me to understand more, although it kind of is as a coach, like if they don't have the if they don't have the motivation, then I'm also wasting my time. Like, why does this matter?

Ian Ross (:

Yeah.

It is.

Right. So why do you think exactly right? So why do you feel like you're afraid to ask that all actually afraid to ask that question? If you know both, it will help them because maybe they haven't actually verbalized, you know, enough people haven't actually verb. They've gone one layer deep, but they don't go even to. And also it helps you. Why are you afraid to ask the question?

Dr Howie Jacobson (:

Boy, you made me feel like that was my idea.

because I don't want anyone in the world to think anything bad of me. And if I do sales, then there are people who are going to think, what a sleazy fucker.

Ian Ross (:

Okay.

Okay, is there a terrorist in some country right now that default thinks bad of you just by who you are?

Dr Howie Jacobson (:

Ha

Yes.

Ian Ross (:

Right, someone already thinks badly about you.

Right now. You don't know them, you'll never see them, you'll never meet them. It makes no difference. You will also help more people in profound ways where they tell everyone about the experience you have with them. If you can actually sell them appropriately, then the people who maybe were never gonna be a fit anyway, who will forget you in a week. And I think you know that, but the fear of that little

bursts of like, it didn't feel good in the moment. Is it possible you're letting that stop you from asking the more impactful questions to help more people? Is that possible? Okay.

Dr Howie Jacobson (:

Yeah, yeah, I yeah, I mean,

if I were to psychoanalyze myself, would say, you know, there's definitely like from how I grew up, I had to be the golden boy. Right. I could never reflect badly. My dad was a labor organizer. You know, I grew up sort of in the public eye and we were all we always had to do the right thing and be selfless and put other people first.

Ian Ross (:

Right. Right.

Dr Howie Jacobson (:

So if I'm using this technique that I think might get someone to buy and I know that I'm trying to inflame their emotions a little bit to make them more likely to take action, some part of me is like, people are going to think that I'm one of those sleazy sales guys.

Ian Ross (:

If you were selling something that a sleazy sales guy sold, that's probably true. Are you selling something with it? Are you selling the same thing the sleazy sales guy sells?

Dr Howie Jacobson (:

Wow, was pretty sleazy. Same thing as sleazy sense guys. I can't even say that. Absolutely not. I am selling high quality personal development and professional success.

Ian Ross (:

Yeah, right

I know, yeah, it's a complete, even though I had a tongue twister in there, you're letting, like, here's the most important thing, because I'll even ask this question. If you were coaching yourself for somebody who was like, hey, I'm trying to coach people, and like, I know I've got a great thing for them, but I'm afraid they ask the uncomfortable question. Not coaching yourself, coaching someone just like you. And they had this exact same challenge.

Dr Howie Jacobson (:

Yeah.

Ian Ross (:

and you knew how good their product was. You knew their heart was beyond in the right place. It was so in the right place that they were hurting themselves, which by extension was mean they weren't helping more people. What would you tell them to overcome that discomfort?

Dr Howie Jacobson (:

Well, I would do my process to get them to see the coherence of why they're they're sabotaging themselves and show them and help them find counter examples. And so it disappears. And like if I know this comes from childhood, it has no bearing on reality now. So maybe it poofed. Maybe maybe you helped me do that already.

Ian Ross (:

Okay.

Okay.

Okay, if it has no, yeah, so I'm asking that because usually what I would say if I was selling you was how can I do that same thing for you now?

after you just told me what you would tell a friend. Like if you had a friend you were coaching and you said, so let's say in the example of, know I need, I know I need this sales training or whatever. And I, I've just been struggling and I just, I just, I need to actually commit. Okay. If you were, if you had a friend who was in the same situation you were in, what would you show me yourselves? What would you tell them? How would you ask? What question would you ask them? How would you inspire them to actually do that? If they had that same situation, they'll tell me and cause it's their words, it's not mine.

And I'd say, can I do that same thing for you now? How can I be that friend for you? Or how is this any different? Or something like that. And then they realize through, people, as you know, people are, have endless advice to give friends, family and strangers, but they don't apply it to themselves. And so you already have it within you, the hero of your own journey. I was just the guide pointing the direction. So anyway, that's a separate thing, but like, yeah, you should probably ask those questions. And then at the end of the call, it's very powerful to collect like,

and maybe not the coaching is:

My concern is that we'll get to the end of this and you're like, this is amazing. I want this. can't like, I know I need this. I know this is going to help me, but because the pricing is going to be more than you're expecting, I'm worried you'll go, gosh, it's, it sounds so scary. I just need to think about this for a while. And then I never hear from you again. And you're not able to help yourself. I'm worried that's going to happen by the nature of calling out the objection myself. They tend to overcome it because they're their own words and their own reasoning is more powerful than me trying to over.

I don't try and overcome objections. I try and get them to overcome their own objections because if you can overcome it yourself, it's so much more powerful than me just talking at you. So there's that idea. So as you collect the pain, it's used that you help solve like the challenges you would help them overcome. Go ahead.

Dr Howie Jacobson (:

So what might that sound like?

I'm collecting the pain of someone whose behavior is keeping them from rising in the organization, or they're feeling cut out of some decision making, or they're not on the core executive team.

Ian Ross (:

There you go. Good enough. Good enough. That's all three. I got three right there. It could be way more. But let's just say it's all those things. I would say, Hey, if I can, if we can go through this coaching, I can make sure like, you don't feel like, you know, the sensation of being cut out of the, executive team, we're able to get you positioned so that you're at least in pursuit of not being cut out anymore. You can

have those better conversations with the people under you so that you can actually inspire action to get better results within your organization, the higher-ups can see that. And finally, you are creating lasting change in your personal life in addition to this, that the ripple effects of this could impact you throughout your entire day. I have to ask you, is this something you even want to prioritize?

I list the pain I'm helping solve and ask an open-ended question around priority. Right? And so it's a micro commitment of like, yeah, I do want to practice or not. If like not right now, I just don't have the money. but like, it feels very powerful. Like, yeah, I want to prioritize it. Okay.

Dr Howie Jacobson (:

So just

to clarify, I heard a closed-ended question, yes or no question.

Ian Ross (:

Great, because then I'm now going to, once they verbalize that, I will then get open-ended. And anytime I'm asking closed-ended questions, it's to introduce a new concept. I often ask, how should we prioritize this? But depending on the level of commitment and resistance, closed-ended is only to introduce an open-ended. So it's introducing an idea. Is this something you would want to prioritize? Yes, it is. Okay. But I guess my question is, it is something you want to prioritize. What do you feel like we should do now?

That's my open-ended question. That's how I close most people. What do you feel like we should do now? Not, let me know what you think. What do feel like we should do? And the answer is, I feel like I I should go ahead and get in the program. That's like the most common thing. I feel like I should do that. And then I still double down on that or even pull away, but not today. I'll say that and they're like, no, no, today. Okay, let's go ahead. Like that, that's how I'm closing people.

Dr Howie Jacobson (:

wow.

Ian Ross (:

It's I'm listen. It always is. There's always variables that are based on the pain that you can help solve and in asking something open. And so I get the buy-in of a yes or how should we prioritize this? It should, I know we should absolutely prioritize it. So I'm also using, plural language. How should we prioritize this? It's my most common closing question. it's a huge priority. Okay. What do feel like we should do now? And that's usually.

my closing question, not do you want to get started today? Do you want to get in this Toyota today? I don't like that, that type of stuff because I don't want counterfeit yeses. That's always going to open ended. If I ask a closed end question like that, it's always to then ask an open ended once they got like a micro commitment to the process that then they can verbalize the next steps. So that closing question will help you way more than let me know what you think. Just that alone is what you actually will help them with. And you can write it down as you go through it. Like I'm gonna, I'll take notes of this, what you're saying. I'll write down, I usually,

The structure is if I can take care of X and we can take care of Y, we definitely make sure C is a priority. How should we prioritize this? Or another sometimes, sometimes I'll ask a close-ended question if someone's really struggling. It's very rare, but like, do you feel like that would be helpful if we can solve all these things together? Yeah, it'd be super helpful. I have kind of an uncomfortable question then, Howie. Do you want my help?

Sometimes I'll do that. Depending on how you're coaching, that can be very helpful for certain avatars.

Dr Howie Jacobson (:

OK, but at this point, we still haven't

talked money, right? You've just said it's expensive.

Ian Ross (:

Well, it depends. so I'm sometimes I'll throw in like in the recapping of like, can do all these things going forward, like the sport of that that's 2000 a month, which I know is a lot more than something we pay for some often. Another idea, this will make you feel bad, but often it helps people to understand the 2000 if you have anything you paid that you've charged more for. It's an anchoring device. We see it all the time. There's a reason we all pay everything that's marked 99 that has a red slash through it for the discount.

the price seems more manageable for people. You know plenty of people are like, I won't buy this unless it's on sale. Even though they want it, they feel like there's a price anchoring of a higher price. So for instance, the most common program I sell is 5,000 for a year, right now at this exact time. And I will also have a business that's paying 10,000 a month for customized stuff for the team. So I will tell people, even upfront, I have to ask questions to determine what to recommend for you.

Some people are paying us 120,000 a year. That's usually too much for people. So I have to ask these questions. I've just anchored them on around a real number. didn't make it up out of the blue that some businesses are paying us. And then they're anchored, oh my gosh, it's so much. And now I ask the question, doing all this, the cost is 4,997, 5,000. If we can do all these things, how should we prioritize this?

Dr Howie Jacobson (:

Right.

Ian Ross (:

That's, that's usually how I do it. include the price within the pain because it tethers the pain to the value or the price, the value, I mean, rather.

Dr Howie Jacobson (:

Mm.

OK, so then you say, what was the exact words? Like, what do you want my help?

Ian Ross (:

If we can take care of if we can get so for like for you to be comfortable, because I don't think you'll like, do you want my help? I don't think that'll be too hard for you. I'm guessing. So probably if we can take care of X, we can take care of Y and take care of Z. That is the structure. How should we prioritize this? Okay. And that's it. If they verbalize it in some positive way, like, again, this is assuming the price is already covered. it would say, Hey, the cost is 2000 a month.

going forward after I've anchored them with a higher price a little bit earlier in some realistic way. And if we can do X, we can do Y, we can do Z. How should we prioritize this? Okay. Well, the question then I have is what do you feel like we should do now? That will help you wait. Cause that gets people out of the way. Once you say, let me know what you think, you're telling them the processes I should think about. And also if you set the expectations of

I don't really have time to play the follow up. So if I hear I need to think about it, I just assume that's a no. I set that up front. They're more primed to actually feel like they're supposed to make the decision now anyway. That will help you in the coaching space for sure.

Dr Howie Jacobson (:

Okay, so then what do you feel like we should do now? And they'll say, yeah, let's get started. And then you say, but not today. Like that feels a little advanced for me.

Ian Ross (:

Well, so no,

no, so you don't have to you don't you don't have to say like, I'm often, if I'm, it's usually if it's wishy washy, I would say if it's let's get started, we can just go ahead. Right? Like, you don't have to do that. But if someone's like, I feel like I should probably do this. Right? So it's really once they're committed, you don't necessarily have to do that.

Dr Howie Jacobson (:

Mm-hmm. Okay.

Okay.

Yeah. OK. Now, at that

point, if I know, and it's different if I'm working with someone who's the company's paying, at which point at which point the price conversation never comes up with the coachee because they don't care. Right. It's what's what's their, you know, HR or their boss or something or whoever I'm talking to. But let's say if it's you know, solopreneur startup guy or small business owner who's going to be making the decision.

Ian Ross (:

Right. Yeah.

Dr Howie Jacobson (:

And then we're going to be doing it on credit card. At that point, the thing I would want to do is like, great, I'll send you an email with the link to sign up.

Ian Ross (:

my God, I never do that. I always take it on the phone. Or I'm on the phone with them or zoom with them, whatever, while they sign up.

Dr Howie Jacobson (:

Okay, so how

do we do that? Because now that feels like, you know, I'm like, okay, yes, good. Give me your money before you change your mind.

Ian Ross (:

so the reason,

the reason is you want to have to make sure you're doing you, you set them up to set the first appointment after they actually sign up. So you have a real reason to still be on the phone with them. Right. So like, because other, when it's like, Hey, like the thing is to get started and then when that's signed up, I want to on the phone with you. We'll pick the, we'll either pick an onboarding call to go through everything and we'll next steps or we'll set that first appointment. And so it's become this natural extension of

We do this after you pay while I'm still on the call with you. So it's not an art. Otherwise it's just give me your money. And we don't want that sensation. It's I want to set the next call. I can't set our call until you've paid because that's, that's what you pay for. And so it becomes a natural extension. It's we're in pursuit of setting that call, but we have to pay for us to be able to do that. And so it feels like a natural progression to set the call.

Dr Howie Jacobson (:

I see.

Okay,

awesome. All right.

Ian Ross (:

Yeah, does that make sense?

So it's like, yeah, so we want to set the next call. I want to figure out your availability and make sure we can set some consistent time. Because if we're just winging it right now, it's never effective. So I'll send you the link. And once you're done with that, we'll pick the first time. So all right, just got sent to you now. That was the email. I think same email before as I sent you before. OK, let me know once that's through. I'll probably see that come through. And we'll pick a time.

Dr Howie Jacobson (:

Okay, so I have to be willing to sort of sit there while they go through that.

Ian Ross (:

Yes,

that will also be uncomfortable, especially starting it. You're gonna be like, So what's really important is to not talk too much, because what's gonna happen is you're gonna feel nervous, and when you feel nervous, you'll wanna start talking, and you can literally blow up the sail by starting to be like, yes, absolutely, and also today I'm gonna go for a walk, and you don't wanna do any of that stuff, because it just, they want,

The feeling they feel tense to it just got sent a link. It's probably more money than they were planning to spend. Like that's a normal feeling. So we don't want to ease the tension you're trying. You have to be comfortable sitting in that tension until they've paid. And then the ease of the tension is in sending the next call and talking about next steps. Like if you can get more comfortable with the awkward tension in that moment, then them, cause it's just, it's a natural thing. We're about everyone is on edge around the actual payment. Like it doesn't matter if it's.

no money at all to you if you're a multimillionaire and it's $20. There's a tension in the exchange of money and value. So it's a normal thing to expect. It doesn't mean they're forced, they're uncomfortable, they're not going to be grateful. The amount of times I've sold someone, like, boy, I hope that that's a little tense at the end. And they're like, oh my gosh, I got the most amazing testimony. That was incredible. Thank you for getting me signed up is probably that's actually probably more common if it was tense at the end because

by the very nature of it being tense is because they were often in their own way. And by me being willing to sit in that tension form, it helped be the guide to help them start getting out of their own way. So I try and go, if it's tense, it means they probably need this even more because they have this inclination. They wouldn't have done it themselves. Right. And so I, I try and always try and reverse, like extend out the time horizon of like the someone who was tense means they needed this more, which means I have to be grateful for the tension because I will get a better testimonial and

a better result and feel better as a coach or as a trainer or whatever, if I'm willing to be comfortable in this tension now. And so I extend out the like, and I think about that at all times. If I can extend out the time horizon for which I'm viewing my tension or my discomfort or struggle, it makes it way easier for them to be on board with what I'm pushing towards.

Dr Howie Jacobson (:

Cool, cool. I can't wait to download this and ask ChatGPT to write me a sales script based on it. I'm very excited.

Ian Ross (:

I sure.

Dr Howie Jacobson (:

This is really awesome. I feel like you've given me the cape. Now I just have to practice flying.

Ian Ross (:

Listen.

Yeah, it's very true. so the practice flying is really important because I, how I think about, learning is like the knowledge itself is just planting a seed in the dirt, right? Without actively watering it, it doesn't actually grow into a plant and water is doing the work and plenty of people are doing a lot of watering, but there's no seeds. And so all they're doing is making mud. It has to come with both. It has to be the actual like

I've learned the knowledge, I've learned how to do this, I've learned the recipe, I've learned the framework, I've learned the mindset, I've learned the words to use, whatever. And then the actual real learning comes in doing the watering of that knowledge, which is actually using it. And those two things going hand in hand. I would say, if I were to sell you coaching, I'll make sure I'm there side by side with you as you do the watering and the new challenges come up and I'm like, I don't feel good saying this and I can make, so.

Dr Howie Jacobson (:

Excellent. Cool. So let's do a close. I know you're not selling sales coaching, sales training for coaches at this moment. You're not selling, you know, be a better activist or be a better partner. But you do have Substack. How would you like people who are like, my God, I got to know what this guy knows. Where can they stay in touch with you and follow you?

Ian Ross (:

Anyway, that's the... yeah.

Sure.

Mm-hmm. Yeah.

So my, I'm most often like on Instagram and then my sub stack is vivid selling, which is also my Instagram name. Vivid selling is my framework for the right questions and the right order to get someone to feel like it was their idea. I didn't even go into that on this, but like if I was running a process, I have questions that I ask in a certain order. And then the nuance of like, Hey, I've got a tough thing to ask you. And I'm afraid this might not, it just might come across the wrong way. If I asked you, might even go, how dare you ask this.

That's the guided persuasion of being the guide and persuading them to come to their conclusion of how you move in between those questions. And I go over all of that on my sub stack. So I think it's vividselling.substack.com. I'm vivid selling on Instagram. The acronym Vivid is a vision, identify, validate, impact decision. We can go over that some other time, but eventually that will be relevant. But yeah, I'm trying to make that.

Dr Howie Jacobson (:

Okay.

Ian Ross (:

a weekly thing that I cover, which is I just break down the principles I'm talking about and try and give it in a actionable way so people can apply it the same way you talked about. like, I can go say that tomorrow. I can practice that. I try and put that in the newsletter.

Dr Howie Jacobson (:

Excellent.

And when you say some other time, I'm taking that as a buying signal that I can invite you back to the podcast at some point.

Ian Ross (:

I would love to come back to the podcast, Howie.

Dr Howie Jacobson (:

awesome,

awesome, well when you you come back and you see me wearing my Rolex from all my sales

Ian Ross (:

Yeah,

exactly. I'll know my job is complete. I was like, now this student has become the master. He's wearing the Rolex now instead of me.

Dr Howie Jacobson (:

Yeah.

I just want to say for anyone who thinks I'm serious that a $20 Casio is more than enough watch for me.

Ian Ross (:

I promise you your audience does not think you're serious. They know you well enough. You're good to go, don't worry. You've got a smart audience. They've got good taste.

Dr Howie Jacobson (:

Good. Right.

Ian, thank you so much. This has been awesome. It's been incredibly valuable for me. hope it's been valuable for I think I think there's a lot of ways in which people selling anything or communicating anything can extrapolate a lot of these ideas and techniques. And I hope people will follow your substack vivid selling. I used to be just search for those two words. They'll find you on all the

all the platforms.

Ian Ross (:

Yeah, and YouTube and stuff like that. I've got a podcast to the close more sales podcast where I kind of talk for, I do a talking head for like half an hour about stuff like that. Now that's geared towards the sales professional entrepreneur. So it's not necessarily geared towards someone who's just trying to apply this to everyday life. So if you're not a sales professional or entrepreneur, it probably won't be relevant to you necessarily. But if you sell anything, if you sell your services, if you're a yoga instructor who's selling your, you know, people to sign up for your program, if you're a coach, if you're a dietitian,

If you do anything where you have to sell, the Close More Sales Podcasts available wherever you find podcasts and also on YouTube would be valuable for the regular layman person who just wants to learn how to communicate better, probably my Instagram and the Substack.

Dr Howie Jacobson (:

OK,

IGSS and podcast. I'll include all those in the show notes. And there they will be. So Ian, thank you so much. This is awesome. And I look forward to more conversations.

Ian Ross (:

Awesome.

Me too, it was a pleasure, Howie, thank you.

Dr Howie Jacobson (:

And that's a wrap. You can find the show notes with links to the stuff we talked about at PlantYourself.com slash 616. So for the last three weeks, I've been doing three workouts.

a week instead of two. And I got to say it's working. I've got to say that amping up the frequency has increased the intensity all by itself. did yesterday we did 100, 500, which is basically do 100 jump ropes and then 20 push ups. And you repeat that four more times. So ultimately you end up with 500 jump ropes and 100 push ups. And I got really close. I got to 89 push ups.

startups

in five sets, which is way better than I've ever done before. So stuff is working. Thank you, Jay, Mr. Trainer. And also we had a really fun Beach Ultimate training where basically I felt like a golden lab where they threw the disc and I just had to run after it. was pairs of us. One was on offense. One was on defense. We basically running after for these long throws. And I was amazed at how

how many times I could run to try to catch these or try to defend them. If you had just told me to run, if you just said, OK, we're going to do sprints.

I would have been gassed halfway through because there was like a game to play because there was a ball to chase. And I remember throwing the ball for Burt, my friend, Peter's golden retriever, like in the early 90s. And this dog would just be tired, like tongue lolling, lying down on the grass. And then you throw the ball and the dog had no choice, had to run after it because of his nature. And I think

I

think part of my nature is to chase after the frisbee, which meant I got a lot of exercise. So movement is doing pretty good gearing up for in April. There's a grass ultimate tournament in Girona. So it'll be nice to strap on the cleats and get out onto grass and not have to deal with sand, although it always does take more of a toll. So that's about it for movement.

Couple of things if if so I'll practice my new newfound scale sales skills and make an offer here, which is on behalf of my daughter, Yelzivan, whom you will have heard if you listen to episode. What is it? Six one.

3 613, PlannedYourself.com, slash 613. You'll meet her. She is a brilliant coach using techniques of memory, reconsolidation and therapeutic techniques from the experiential therapy movement. So if you're feeling stuck on something, if you want to improve a health behavior or change a habit or improve your internal emotional state, I'd highly recommend you get in touch with her. And right now she doesn't quite have the

website set up. So if you email me, HJ at PlantYourself.com and let me know you're interested, I can facilitate that connection. And if you'd like to work with me as a coach around your life goals, your career goals, hit me up again. HJ at PlantYourself.com. That's about it for this week. As always, be well, my friends.

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