CUTTER CONSULTING GROUP

E153: Sales Grit with Catie Ivey - Part 2 of 4

January 5, 2024


How would you define a growth mindset, and why is it considered crucial in personal and professional development?


This is part two of the conversation I had with Catie.


In Part 2, Catie and I talk about:

  • Say YES and testing everything you can
  • Putting the “Team” into sales team
  • Knowing what you want to sell (and what you are good at)
  • Truly passionate people don’t worry about “working after hours” 
  • Recruiting great sales people


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Connect with Jason on LinkedIn

Connect with Catie on LinkedIn



Catie’s Info:
Catie is a seasoned sales leader with a passion for coaching and people development and a track record of quota attainment, driving YoY growth, and building a cultivating true value selling methodologies within an organization.

She believes that great cultures produce great results, that empowered people empower others, and that there is no limit to what a team of gritty, hardworking, genuinely curious people can do when they are committed to winning together.

She is an avid proponent of the power and possibility of digital transformation, a lover of all things digital, and genuinely enthusiastic about technology’s ability to drive human connection. She believes that great brands build great connections and harness best in class technology to drive genuine engagement and build real relationships, which has turned her into a MarTech enthusiast with a love for all things sales and marketing.


Catie’s Links:

LinkedIn: 
https://www.linkedin.com/in/catieivey/

Twitte
rhttps://twitter.com/catiecoutinho

DemandBase: 
https://www.demandbase.com/

  • Show Transcript

    Jason: Welcome back to the sales experience podcast. My name is Jason Cutter. Thank you for being here. So glad that you’re a part of this journey on the sales experience. This is part two of my conversation with Catie Ivey and, uh, I’m just gonna throw it right in here and make sure that you’ve checked out part one, which was yesterday. And let’s just roll right into it. I remember closing them in five deals in five days, and he was shocked because my boss was an operations guy, was, he’s like, it took me a month to close my first deal and I was like, well, you’re an ops guy and I’m a sales guy. And so, you know, but then I could speak to it and train everybody and write the script based on what worked and then, you know, evolve from there. So I think that’s always of


    Catie: Five days, man. I’m jealous of that.


    Jason: Yeah, well, it’s business to consumer, so that helps. So keep that in mind, but still it was, it was what they had never seen done there. And then, uh, you know, set the precedent.


    Catie: I’m in the thick of Q4 close with my reps right now so I can use some five.


    Jason: All right, we’ll work on that for sure. So it’s funny too thinking about the growth mindset that you were talking about. I, I’ve been telling people this a lot these days is I am in a very much of a yes mode right now in my life. And in general, like everything in my mind is a yes right now. So every opportunity, everything with a sales team, everything with marketing, somebody on, you know, cause I consult. So I have several companies I’m working with. Somebody comes up with an idea, we want to try things out. I’m very much yes, like let’s try it. If it’s a test, obviously, you know, set the budget and the time and effort appropriately. But just a yes. Like somebody says it recommends a book. I’m like, okay, sure. Why not? Let’s try it. And I think that’s fascinating. You talk about the growth mindset and also the grit side.


    Catie: Yeah. Do you have any concerns with, I’d love that. And I feel like you, and I think quite similarly in that in terms of like, yes, let’s do it. There’s lots of possibilities, lots of potential. Do you find that ever creates challenges from a time management perspective or even prioritization of how you’re spending your time?


    Jason: Yes, but there’s more hours and uh, you know, it’s all segmented in there and it’s, but I’m also really good at saying yes to things and if it’s in a business perspective, then how do I get help? How do I delegate it? So we want to test this marketing. Okay. So who can help with that? I’m not the only one working on it. I’m just saying like if a salesperson comes in and says, Hey, I’ve got this idea, maybe we should try this, if that makes sense. It’s like, okay, instead of, no, that’s not how it’s done. Or that’s not what we do. Or no, just keep doing what you’ve been doing. Or you know, don’t worry about the marketing side. It’s like, Hey, why not? Let’s try it.


    Catie: Yeah, that’s a really good point. And I think if you can understand very clearly, which I know you do, like what’s the focus on what’s the end goal and the broader priorities. There’s ways for so many things to tie into that and become incorporated into those same goals, even if it’s, you know, different ways of going about it.


    Jason: Well, and then also tying it back. I love what you said about you’ve got new reps one to three years, they’re saying things you’re learning from it. That growth mindset where you know, you and I, we’re not better than way. We have more experience in some areas, but there’s always more you can learn.


    Catie: Yeah, for sure. 100%


    Jason: So this is one of my questions I may or may not get to officially, but let’s talk about the hiring process. You talked about hiring for genuinely curious people. How do you identify that for any managers or owners out there listening to this, or salespeople trying to get a job in sales, they want to be successful? Like how do you select for that? How are you finding that out?


    Catie: Well, I’ll preface it by saying I don’t think that I have the perfect formula. Okay. I’ve learned that hiring is one of the things that I need to surround myself with. Some other good people because I can tend to be somewhat impulsive. I make quick decisions or gut reactions based on certain things that trigger me specifically. So I’ve learned that I need to incorporate others. Vantage point am very open to feedback. Curiosity though to me is pretty simple. I want to understand how people spend their time both at work as well as outside of work and you can pretty easily figure out like do they do lots of interesting things. You know, maybe they’re an athlete that’s pursuing something really cool outside of work. For me, usually most of the people that I feel like are genuinely interested in business are curious about business. They’re usually either reading books or they’re super into podcasts that they’re learning and they’re bettering themselves in a way that’s not directly tied to how they get paid today.


    Catie: And usually that’s because they’re somewhat focused on a bigger picture. They’ve got some goals and not the standard. You know, where do you see yourself in 10 years? And expecting them to have a clear script for that. But I want to know that they have big ambitions and if they have something that feels big or audacious from my perspective, are they doing things today that actually progress them towards that in some capacity? So that’s feels kind of vague from an answer perspective, but that’s usually what I’m looking for. A lot of times it happens to very natural conversations just like what you and I are having, but I’m stressing to try to figure out what’s the end goal and then are they doing things today that are driving them there?


    Jason: And that makes total sense. And it’s not super vague because I know from those conversations what that could sound like, which is, you know, what are you reading? What do you listen to, what are their stuff, you know, you know, what was the last book you read? And when that kind of question comes up in a conversation and then you find out, you know, have they read anything? Are they reading anything or watching, you know, videos or webinars or listening to podcasts cause everyone takes info in differently for sure. But you know, finding out what they’re doing with all of their free time and their, their drive.


    Catie: Yeah. And there’s different roles. So there’s folks that are selling very different things. I sell in a very specifically B2B marketing space. And so if someone’s interviewing for position with me, if they’re not interested in how revenue operations works, like how are companies going to market and making money from a sales and marketing perspective and sales marketing alignment, they’re not reading the learning something about that. It’s going to be, cause our, every sales process we go through is quite complex, very unique. And you’ve got to be able to position yourself as a trusted advisor. So there’s just gotta be some actual knowledge transfer and share that’s happening there. I feel like in order to be good for what I’m hiring for, that’s certainly different than someone that could be selling, you know, a consumer product or into a very different industry. You know, there’s aspects of my skill set that you know, I’m, I couldn’t be selling an Uber technical, you know, it infrastructure software, that’s not my background and I’m not as curious in that area. But when it comes to how revenue organizations work, like you sure as heck better believe. I’m really curious there


    Jason: And that’s fascinating cause that really reminds me of where I was at. I, like I said, I worked at for a couple of years doing tech support. I thought at the time I wanted to go down that technical path. I thought I had an aptitude and a desire to work in a technical space in a company. Now tech support is a terrible way to start because yes you’re solving problems and yes you’re dealing with technology, however it’s customer service and complaining and painful and you solve one case and there’s 10 more people waiting to blame you for what broke. That’s probably not your fault. And so that’s a terrible like test to see if you want to be in tech. But what I noticed about six months into it, it is, I would come in from the weekend on a Monday and everyone will be talking about what they did on the weekend and my coworkers, a lot of them who loved it and they really saw themselves longterm there.


    Jason: You know, they would talk about the magazine or the articles they read about motherboards and how they were like fixing their computer and what they did and the programs they were working on. And I’m like, yeah, I played some basketball and I hung out and I went to the moon. I’m like, I don’t care. Like I literally realized I didn’t care. And tying it to what you’re talking about, I was like, I wasn’t curious and I had no passion and desire about it. And then many years later I was in mortgage and then helping people in foreclosure and then literally I would spend my evenings and weekends reading like banking and foreclosure, like trade magazines for fun and earmark the pages and highlight things and I’m like, Oh crap. That’s when I realized I’m like, Oh crap. Like, this is where I want to be and everything was just so easy.


    Catie: I love that. That’s such a great example. And cause sometimes people have this negative connotation of people that work after hours or work these long hours or biting off more than they can chew. And I feel like if you’re doing something that you’re truly passionate about and really, really enjoy, then there should be this natural sense of like, Oh, I love learning about this or really enjoying taking my skill set to a new level. And it doesn’t necessarily, of course there’s times where things feel stressful in any job in any career, but it’s got to feel fun at least a good chunk of the time. And I think that’s the perfect example you gave.


    Jason: And it’s funny because for years people ask, you know, always ask polite questions or in conversations like, what are your hobbies? What do you like to do? What do you do for fun? I’m like business and study business and read business books. And most people in the world, maybe even listening to this, you think it like, this dude is nuts and he’s a workaholic. It’s like, no, I just enjoy that and it’s fun. And you know, listening to business podcasts or sales podcasts and, and I used to kinda like shy away from that question in the past or answering it. And then I realized like, there’s nothing wrong with that. I just enjoy it. Right. I enjoy other things too. But you know,


    Catie: it’s really love figuring out how companies make money and helping them make more money. Yeah, that’s exciting.


    Jason: I mean, I’m the kind of person where I go, I’ve done this for years. I go into a frozen yogurt place and I’m sitting there and I’m watching everybody and I’m running the math and figuring out like how much are they making and how does this work? And you know, what’s their business model? So, you know, when you find that in your life, then everything becomes easier. Where that place where you’re just curious and excited and you just, you know, can’t stop learning about it. Yeah, I agree. So let’s talk about, we had kind of discussed this beforehand before jumping on here is the whole topic that I covered in one of my episodes about order takers and how that plays into, you know, what you see now you’re making some decisions and maybe you want to start, cause I just remembered I wanted to ask you about, you said you make gut decisions for hiring that may not always be the best. Are you picking people that are, you’d make your gut and they’re wrong or you’re making your gut decision and they’re right and you’re just bypassing the process.


    Catie: It depends on the specific scenario. I definitely have examples of both. Quite often I can read people relatively well. I’ve worked hard to develop some self-awareness, which then I think is tied into my ability to read other people. But because of that I can read someone relatively quickly and then make a quick decision and not always do the right element of due diligence. That’s when we think specifically, that’s why I will purposely bring other people into the conversation. Yeah. Does that answer that, that piece of the question?


    Jason: It does cause I’m the same way. Like I rarely look at a resume during an interview. It doesn’t matter. Like I’m just having a conversation and I usually know within a minute or two of where I think things will go.


    Catie: Yeah, and even to your point, which I know we’re going to segue into this, your episode on order-takers, I feel like you can also read relatively quickly whether someone has that tendency to simply respond and react, which is a lot of what order takers do versus being willing or brave enough to lead the conversation and even an interview if they come with intelligent questions and are willing to stop it as layer in questions or even push back or give further clarification. All of those things to me are early indicators of the fact that someone has the capacity not just to sit back and react and take orders, but maybe lead conversations.


    Jason: Before we get to the order taker one here, because this keeps reminds me anyway. No, no, no, no, no. For anyone listening to this who’s thinking about getting into sales or is going into interviews. I know that the standard is come in prepared, have questions, build all of that stuff. And I will tell you from me, and I’m sure this is the same for you, Catie, is that anybody who doesn’t have any questions and doesn’t ask any questions, it’s done. Like it’s over. Like if they’re not asking, even whether they’re prepared or not, like written down or they just have them in their head. If I ever say like, so do you have any questions? And they say no, then that’s it. Okay. So now let’s talk about order takers. So what has been your experience with that and how do you see that playing out in the roles that you have and how much do you think is trainable? Kind of fixable. And you know, somebody who just needs some coaching and leadership or you know, that’s just who they are and it’s not gonna work.


    Catie: So I’ll preface it by saying with the right mindset and resilience, I think almost anything is teachable and trainable. Just like you and I have given examples of maybe not being a natural in sales early on. I definitely have a fault and improved in a lot of ways that if I thought that a lot of sales capacity was not teachable, I’d be really shit out of luck there. Um, so most things I think are trainable in terms of this concept of being order takers versus true, you know, leaders that drive a conversation. It’s something that I see very often, especially in it’s even more prominent actually, I would say in females. Partly we talk, have an old quarter conversation about that, but we’ve been conditioned to be followers in certain ways and we’ve been conditioned to be people pleasers. Again, making broad generalizations, but to be people-pleasers in a lot of situations.


    Catie: So when you put someone that might be relatively young in their career and not super confident yet, that has also been conditioned to be somewhat of a people pleaser, it’s easy to want to be the person that has all the yes answers that, Oh, you need this, I’ll absolutely do it. What do you want to do next? Oh, absolutely. We can certainly set that up around your schedule. You need this price point, I’ll make it work for you. Like being that person that’s very accommodating. And then there’s other people that of course are on the opposite end of the spectrum and you have to teach them to be a little more graceful. Yeah, absolutely. But to your question around probably that where you start in terms of that individual that is a little bit over accommodating the first steps, definitely making them aware.


    Catie: So we, we use call recording software gong, um, which is amazing from a coaching perspective, but giving them very specific snippets to go back and listen to themselves and give themselves feedback on how they could have been either more direct or ask for something in return. So just the concept of give gets like you might get six different requests at any point in the sales cycle. If we’re going to do those things, what are the things that I can expect in return? And that feels for most reps, whether they are very senior or very junior, very tangible. Like, Oh, if I’m going to give something, I need to figure out what’s in it for me. And is there some sort of reciprocal action because that doesn’t just get you things, which is also important sales, but it builds the sense of perspective. Like, Hey, we’re peers here together. Like, I absolutely want to partner with you and make this worth your while and a win-win, but gotta be mutual in terms of how we’re going about this. I think that’s maybe the concept that you’re trying to breed into these sellers to move beyond just that order-taker capacity that you talked about.


    Jason: All right. That’s it for part two of my conversation with Catie Ivy. Make sure to go to the cutterconsultinggroup.com website to find her links and the transcripts you can connect with me on there. You can also follow me on LinkedIn and as always, keep in mind that everything in life is sales and people will remember the experience you gave them.



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By Jason Cutter February 19, 2025
What does it take to build the ideal Sales Experience? Why does it even matter? Maybe you think you already have one. You are a professional sales ops leader. You have put everything you can in place to help your salespeople sell more. You have optimized the processes so that your sales team can focus on one thing – selling. But I promise – even if you think all of that is true, it’s not. The Reality: No Perfect Sales Experience Exists I have never seen any company or team with the ‘ideal’ Sales Experience and operation. And to be honest – I have never built one successfully. Why would I admit that? Because the ideal Sales Experience is aspirational and business, teams, processes, and customer needs/desires are constantly changing. So as soon as you put new processes in place, something else needs to change and evolve. The Scalable Sales Success Iceberg In my Scalable Sales Success Iceberg – there are 24 categories that, when built out, create a scalable sales machine – where you can add in an input and get way more output. I would love to see companies have all 24 categories set up and running optimally. But that’s not even possible – because, as I mentioned, things are always changing. Focusing on the Biggest Levers Here is the key – to build the ideal Sales Experience takes focus on the biggest levers. The ones that, when pulled, create the biggest and best results. There are many processes and systems that you can put in place – but those are going to get you a few percentage points of improvement. Instead of putting it all in here, I want to make you a special offer. Email me at jason@sellingeffectiveness.com with your mailing address, and I will mail you the book that I co-wrote with Nick Glimsdahl called Reasons Not To Focus On The Sales Experience. It will be your starter guide, facilitating the creation of your ideal Sales Experience.
By Jason Cutter February 18, 2025
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By Jason Cutter February 17, 2025
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By Jason Cutter February 13, 2025
The Balance of Effort in Sales The blogs this week have been about the other person going most of the way. Whether it’s a prospective customer and your salesperson, where the salesperson truly can’t want the deal or make most of it happen for that customer to truly be successful. On the path for that prospect to becoming a customer, they should go at least 51/49. Whether it’s your team and their manager, the manager can’t want the team to succeed more than the team actually wants it for themselves. It’s not scalable for the coach (manager) to run on the field every play to win the game for the salespeople. What about sales ops processes and systems? What about the tools available to the sales team and the ones that are classified as sales enablement? In a reversal of philosophy, I believe the sales ops processes should go 90, the team should only have to go 10. Why Do We Need Salespeople? Let’s start where it matters – what is the point of having salespeople? I know many owners question the need and desire to have salespeople. They are hard to manage, tough to deal with, always want more money (potentially for doing less work and closing less deals), and are very resistant to change. Of course, that is a generalization. Of course, there are salespeople who don’t check those boxes. However, having worked with a lot of teams in a lot of industries, that generalization isn’t completely wrong or unfair. So if there is even a small part of that which is accurate, why would we even mess with the messiness of having salespeople? Of needing to employ and manage humans? The Human Element in Sales We need them. That’s why. Even in 2025, AI and technology has not successfully replicated the requirements of sales – which is about helping a human (prospect/customer) make the right decision and move outside of their comfort zone to buy something new. It still takes your human (salesperson) to persuade that other human. It’s why I say all the time that its not B2B, B2C, Retail, SaaS, etc. – it’s H2H. Sure, people can buy something online or even in a store without speaking to someone. But if it’s a considered purchase where there are options and decisions to be considered – it still takes a human being involved. That means ultimately your human (salesperson) has one job, and one job only – persuade the right prospective humans to buy. Minimizing Distractions for Salespeople Everything outside of that mission, task, focus is a distraction that takes away from their highest and best use. Imagine if we had a surgeon who had to prep the room, prep the patient, schedule the surgery and meetings, and do all the parts of the surgery themselves. Nope – they show up for the surgery and do what they do best. Then they take off their gown, gloves, and walk away to get cleaned up and move on to the next thing. Your goal as a sales ops leader is to support the team with systems and processes that allow them to focus on the one thing you need them for. The human part. It would be amazing if they could show up, talk to people, and make sales happen. Of course, there is more that they (and any professional) need to do before, during, and after the sales conversation. But your goal is to minimize all that. Every hour that your salespeople aren’t selling or doing sales-related activities, they aren’t moving revenue forward. The Ultimate Goal of Sales Ops What processes can you put in place that go 90 percent of the way, where the salesperson can do the last 10 percent? An example would be building an email campaign that runs automatically, and when the right people reply, the salesperson gets involved in getting that person from email to phone call. Another example would be your CRM serving up people for the salesperson to call – leads or anyone in the sales pipeline flow – with all the backstory, research, data, intel needed for them to review it then take action. What can you put into place that takes away as much distraction and effort from your sales team such that they can focus on the one thing you need to focus on – other humans?
By Jason Cutter February 12, 2025
The Danger of Doing Too Much as a Sales Leader Alright – so maybe they don’t need to go 90. In true servant leadership mode, you would go way more than 10% of the way to your team. But you have to be careful, as a sales leader. The inclination might be to do it all for them. To help them close their sales. To make excuses for them to your leadership as to why they aren’t closing more sales. Especially considering the very high likelihood that you are a sales manager because you were a great salesperson in the role that you are now managing. And there is a slight chance that you are a player-coach…so you are leading and selling. This can make it really tough not to want to run out on the field to win the game each time. But that doesn’t scale. That doesn’t lead to increased results. You can only sell so much as one person. Creating a Culture of Ownership So, you need to have people on your team that are coming to you. What does that look like? The pinnacle is a salesperson who doesn’t close a deal, comes to you right away and asks for feedback. They want some critiques as to where they could have done things better, different that would have led to the desired result – a closed sale. That takes a healthy level of ego by a professional who has the ultimate growth mindset. They know there are always ways to improve. They want to improve. And they are willing to risk their ego (and the internal, protective, primal part of our brain that doesn’t want to risk our place in the tribe) by asking for feedback that could be negative. Whenever you can, encourage that type of response. Ensure that the team knows that the team itself, and you as their leader, is a safe space – where the goal is to improve, grow, win and that everything done to support each other is done in that mode. They truly have to feel safe to share their mistakes and to get support in learning how to do more, better. Feedback That Drives Growth Part of this takes team and individual meetings that are actually filled with positive support. That doesn’t mean it’s always positive, motivational fluff. It’s not even about the shallow strategy of the feedback sandwich. Its about being real, honest, and empathetic – meaning “I see you are here, I know you want to be there, I will help you get there – even if its hard and it means saying hard things.” It should never feel mean or abusive or like an attack. But you can give some really direct feedback that will sting that ego I mentioned, but the person will know the intent behind it. The second part is hiring this type of person. Hiring people for the team that wants to win, grow, succeed. And they know that you don’t get better by being coddled, sheltered, or protected. You want people who don’t like the thought of perpetually living safely in their comfort zone. And they are excited about the opportunity to be a part of a team that pushes everyone, empathetically, outside of their comfort zone. Are You Leading or Just Managing? If you find yourself as a leader having to push your team, or going to them most of the time, or most of the way mentally – then they see you as a manager not a leader. They see you as someone who manages them, pushes them, and wants them to do things they don’t want to do. I have written some blogs here that go into what your role should be – as a leader, not a manager. Pulling people along with you, inspiring people, and supporting yourself with a team of people who want to win. Not just those that want to show up, do as little as they can and hopefully go unnoticed (yet – complain about not making enough money and how the comp plan isn’t fair, or the leads are bad, or their schedule means they can’t be successful.) Make sure your team knows that they need to come to you – at least 51/49. They should be asking for help, guidance, training, feedback, and support more than you are having to push it down onto them.
By Jason Cutter February 3, 2025
If you have seen the movie Hitch, then you know the scene. Will Smith’s character (Hitch) is trying to coach Kevin James’ character (Albert) on how to finish out his upcoming first date. He is giving him pointers, one being that if his date fumbles with her keys at the door, it could mean she wants a kiss. So Hitch wants to see if Albert knows what to do – for a good night kiss. Hitch gives him the advice “you go 90 percent, and then wait for her to go 10%” which Albert then asks “wait for how long?” Hitch: “as long as it takes.” Albert leads in, Hitch is holding back to see if Albert will wait, and then Albert goes all the way and gives him a kiss. Hitch gets upset, and says “You go 90, I go 10 – you don’t go the whole 100%.” The Sales Analogy Kissing our prospective customers is not acceptable (just ask HR!). But the concept is the same. You don’t want to ever make 100% of the effort for your prospective customers. You don’t want to be the one who is doing all the work. Fundamentally, it is not good practice to want the deal more than the other person. When you go your 90, you need to wait – as long as it takes – for the prospect to go to their 10. And I would say that you want to go somewhere between 10-49, in reality. How Successful Sales Professionals Balance Effort Successful sales professionals know how far they have to go to meet the prospect where they are, while also knowing how much effort the prospect needs to put in to show they are committed. Where most salespeople get in trouble is they get desperate. They want the sale (kiss) more than the other person and they go the full 100%. Of course, persistence is important. And you won’t get what you don’t ask for (although…if you have followed me for any length of time, you will know I am very against having to ask for the sale). But you also have to ensure that your prospects actually want what you are selling. And they want it for their reasons and their motivations. They are driven to pursue your production option(s). They must go 10, 40, 60% of the way to you. The Pitfall of Chasing Your Prospect Just like courtship and relationships – if you find yourself chasing and one-sided-pursing the other person then it means you want it more than they do. It also means they own you. You are essentially begging them for the relationship – convincing, manipulating, begging, bribing, persuading your way forward. Which means they consciously and/or subconsciously know that they are in control. Because if they say no, you will keep pursuing and offering solutions. In sales – that looks like a salesperson who is calling, emailing, stalking a prospect – making offers, offering discounts and trials, and trying to find any way to make deal work. They are going 90-100% of the way for the prospect, not requiring them to go anywhere towards the agreement. This will end terribly. If they do decide to buy – taking the discount, free trial, taking the sale bait – they will not be happy (since they weren’t bought in for their reasons), they will look for reasons confirming why they didn’t really want to buy anyway, and they will know that they own you. Your company will have to convince them on a regular basis to stay in the relationship. The Right Balance for Customer Ownership You fundamentally need that prospective customer to come to you. Not 100% where you are just an Order Taker. But potentially 51% of the way – so they want it more than you. The more you can get them across that 50/50 threshold, the more they will be a satisfied customer. But remember – at 51/49 – they still need persuading, they still need to understand the value of your product for where they ultimately want to be in their life/business, and they still need your support. They lean in the right amount, you lean in the right amount = sales magic!
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