CUTTER CONSULTING GROUP

E151: Being A Sales “Leader”

January 5, 2024


How can sales professionals transform into effective leaders to guide prospects to a successful sale?


Are you a leader of sales?

And I am not referring to a sales manager, team lead, VP or owner.


I am talking to you – the salesperson.

Your challenging role as a sales professional is to be a leader.


Of your prospects. To the finish line.

How can you be a sales rep and a leader? Check out this episode.



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Enroll in the Authentic Persuasion Online Course

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  • Show Transcript

    Jason: On today’s episode, I want to talk about sales leadership. Welcome to the sales experience podcast. My name again is Jason Cutter. So glad that you’re listening and on this journey to help make your career in sales better. Your sales team’s life better and your prospects lives better while at the same time doing the right thing for you, for them achieving your goals, helping them get their goals, and so hopefully you’ve been enjoying the show. Make sure to subscribe if you’re not everywhere that podcasts are available. You can also connect with me on cutterconsultinggroup.com you can follow me on LinkedIn and now for today’s topic, what I wanted to talk about is leadership and sales. Now typically what happens is when people hear the term sales leader or leadership and sales, they’re thinking team lead, sales manager, sales coach, consultant, owner, all those people who are in leadership and leadership being a higher level.


    Jason: So somebody is higher up in the org chart or more experience or you know the person on the floor with tons of experience that’s kind of leading the charge every day or helping people feel better when they get down. If he gets some rejection from a prospect or a client that cancels or returns whatever you sold them, you know you’ve got the leader on the floor for the morale and then you’ve got the leaders that everyone thinks about. Now what my topic is for today and what I want to focus on and what I really want to shift for all of you listening who are sales professional salespeople in a sales role dealing directly with prospects, converting them into customers. Cause I want to talk about your role as a leader. Okay, so a lot of times sales people don’t see themselves as a leader and don’t embrace the leadership that is required to be a sales professional.


    Jason: Now let’s talk about leadership. Definition of leadership on a basic easy level is somebody who inspires others to follow them, right? There’s managers and then there’s leaders. Managers manage people tell them what to do. Delegate direct hold people accountable. Leaders on the other hand, they create a framework. They have a vision, they know where they’re going and they inspire other people to follow them, and that’s the big key managers, people who are in charge, people who are running things. Sometimes we’ll use manipulation to get people to do what they want, right, but sometimes it’s the carrot or the stick. There’s some kind of manipulation, whether it’s a forceful, harsh manipulation or it’s just a very subtle and kind of passive no matter what. That’s on the management side. A leader is somebody you want to follow a leader, whether it’s in the church or military or an organization or somebody like that where you encounter that person and you’re like, wherever they are going, I want to go as well.


    Jason: If you’ve gotten a job at an organization, as a salesperson, manager, leader, whatever that is, and you have come into contact with the ownership or you understand the culture and there’s a vision and the mission and core values, then that’s something that you want to be a part of at a deeper level. That’s a different feeling than when you go to work somewhere and it’s a job and you’re told what to do and you don’t really understand the mission and the vision. You don’t really care and you’re not understanding it. Last week I talked about marrying the vision and dating the strategy, right, and that’s about having a vision and knowing where you want to go and having everyone follow. Now it’s a salesperson. Your job is to be the leader of your prospect. Now, I know this sounds weird, rarely ever hear this topic or I’ve never seen anyone really talk about it, but your job as a sales professional is to be a leader and lead your prospects to the finish line, to the promised land of a solution for them.


    Jason: Now, a couple of weeks ago I talked about giving to give and making sure that you’re doing things for your prospects to help them get into a better place and not about you. It’s not about giving them to get, it’s not about pushing them to sell so you can get what you want. It’s about helping other people. When you act as a leader in your sales role with your prospects, it’s about getting them to follow you. Now, how do you get them to follow you, right? They have a problem. They have a need for your service or for your product or your idea, whatever it is that you’ve got. How would you get them to follow you? You’re the sales person. They’re the buyer. You should be directing them. You should be pushing them, should be moving them forward. Well, the key is to do what leaders do, which is to ask questions.


    Jason: It’s to build the framework. It’s to then find the issues that you want to solve instead of having a vision, right? I know that my vision is to help my prospects get from here to here. When they encounter you, when they talk to you on the phone or they meet you in person, wherever you’re at in your sales process, when that occurs, there’s a different energy that leaders have. There’s a different confidence that leaders have, and I’m not saying you have to be that charismatic leader, the one that has lots of stories. That seems to be the life of the party standing on tables. That’s not leadership. That’s a personality trait with highly charismatic extroverted people. I’m talking about leadership. There’s some amazing leaders out there in the world who are very quiet and very passive, but their energy and their power comes through in what they say and where they’re going and people just naturally want to follow them.


    Jason: And so your job as a sales professionals to do that same thing. It’s about building that framework, holding that space, and having your prospects come with you on the journey to the finish line with a closed sale. Now I know this might sound very woo, might sound very weird, like we’re just going to sit in a circle and you’re just gonna you know, chance and have your prospects follow you and you’re just going to talk about these theories and hope that they come with you and just grab their credit card and pay. Right? But no, that’s not what I’m talking about. I’m talking about actually being a leader and taking charge of the conversation and then having them follow you, like you know where you want to go so they’re going to follow you in it. And how do you do that? One of the best things to do, and this is some practical information so you know how to do it, is to focus on enrolling and not selling.


    Jason: Now, I’ve talked about this before on the show many, many times, but it’s about enrolling versus selling. When you’re selling something to somebody, you’re trying to persuade them and or manipulate them for your reasons, right? And remember, people don’t like to be sold to. They like to buy, they want to buy for their reasons. They don’t want to be sold to for your reasons. Even if you can see that what makes the most sense for them is very clear. You can’t push them into it or you’re going to have cancels. You’re in a buyer’s remorse. It’s not going to be as effective. So you need to make sure you’re enrolling. Now, what is enrolling? Like? Enrolling is kind of similar to the DMV. When you go there, they’re not trying to sell you anything. They’re just trying to help you. You have forms you need to fill out.


    Jason: They’re going to take your money. They’re going to process, you’re gonna move on. Now, if everyone treated everyone like the DMV does, that’s going to be terrible and no one’s going to want to follow you, right? That’s not a good leadership model, but you want to do is lead your people over it because of your passion and your desire to help them. That energy will come through. Now, here’s a good example as well. If you’ve ever known somebody or been in a relationship where somebody could make better decisions, right? Maybe eat healthier or workout more, you could tell them to work out more. You could tell them to eat healthier or you could just do it yourself and be that guiding post and that one that they want to follow and say, wait a second, it’s working for them. This seems to be good. I’m going to go down that same path.


    Jason: Now, how do you do that as a salesperson? That can be tough at times because you have usually a short window of which you’re trying to lead someone, but you have to make sure that they understand that you are very clear on the vision and the value of what your service or product does for people as well as how you will get there and the process and then what it’s going to feel like at the other end, right? Everybody is in things for themselves. What’s in it for me? Always got to keep that in mind that your prospect only cares about themselves. And so if you can set this framework of where you’re going, the vision and the destination, they will want to follow you there, especially when you put it in terms of what it’s going to feel like for them, what it’s gonna look like for them, and how their life is going to improve.


    Jason: Now keep in mind, it may sound like this only applies to people who are helping others, right? Get out of debt or deal with some personal issues, but that’s not true. The supplies business to business, business to consumer, whether you’re helping companies buy a new CRM or you’re helping an individual buy a car, all of that is about leadership and that vision that you have for them and then getting them to buy into that vision. But that’s enrolling, not selling. If you sell it too hard and you push it, it sounds like you’re trying to get people on board and it’s not going to come across the same. When you’re enrolling people and getting them to enroll in buy into the vision, then they are with you and you can lead them to the promised land. You can lead them across the finish line. Of course, with the caveat that it’s got to apply to them.


    Jason: They’ve, it’s gotta be a good solution. It’s gotta be something that takes care of their problems, their issues or helps them with a goal or a need that they have. But when you do that, when you enroll them into your vision for them with your product or solution as that vehicle that’s going to get them there, then you’re a sales leader. And sales leadership is all about getting people on board, having people follow you, and then also doing whatever it takes. And again, this goes into last week’s conversation about marrying the vision and dating the strategy is the strategy part is overcoming obstacles. How are you going to get there? Who needs to be involved and being very flexible in your sales while at the same time being very clear on what your vision is as the leader of that interaction of that transaction. If you find yourself talking to your prospects and you get done and you realize that you didn’t make the sale and they kind of walked all over you and they asked you lots of questions and they beat you up and they drove the process, you were not acting like a sales leader, you were not leading that conversation and directing it.


    Jason: Okay, and I’ve mentioned this analogy in the past, but think about the doctor example, go into a doctor’s office. They are leading the process now. They may entertain some of your questions. They may open the floor up to you to for your questions or concerns, but they are leading it the whole way they are driving it. And then based on their professionalism, based on how they’re handling things, and then based on their diagnosis and prescription, you want to follow them and their direction because you know it’s going to get you in a better place because you’ve trust them. They’ve built that trust with you as an authority and as somebody who cares about you and getting you there. That’s how that goes. That’s what that feels like. And that’s what you want to create for your prospects. So hopefully that helps. Remember, always focus on becoming a sales leader, that your prospects literally want to follow and will go with you because you know you’re there to help them and at the end they will be in a better place. So always focus on that, both in sales in life. Just like I say, as always, keep in mind that everything in life is sales and people 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
The Numbers Game Mentality is a Losing Strategy Sales is no longer a “numbers game.” You cannot succeed, long term, by focusing on volume of activity. Making a million dials, sending a million emails, knocking on a million doors (the first two are way easier than that last one) is a scorched earth strategy that will sink your business. You can’t out-dial a bad sales process. It will lead to even more bad online reviews. You can’t out-email a terrible sales funnel process that requires people to jump through poorly planned hoops. You can’t out-knock your way past slimy tactics and bad products/services. The Danger of the "Every No Gets Me Closer to a Yes" Mindset The whole “every no gets me one step closer to a yes” mentally is dangerous. That mindset and strategy assumes that it’s a numbers game. That the only thing that matters is finding the right person who will buy from you. Potentially, no matter what you even say – they are just ready to buy. Not only will this destroy any online reputation you have it will also wreak havoc on your team. It is the fastest and best way to burn out your team. It will lead to a revolving door or hiring, training, and quitting as people realize how unfun the game is you have built and how hard it is to be successful. It will also feel like a mismatch – very few people (and hopefully even less over time) are long-term excited about the business model of calling 500 people a day in hopes of making a few sales. If It’s Not a Numbers Game, Then What Is It? It’s quality over quantity. [Now…note – it does take a certain quantity of activity to fill a sales pipeline. So I am not saying that your sales team can just sit and wait for people to fall into their pipeline with money in hand.] It’s about the Sales Experience. It’s about your team ensuring that they are providing the right and best experience for that potential customer – in a way that sets them up to get into the buying mood and mode. All that matters is the Sales Experience. How can you support your team in terms of the quantity of activity to fill a pipeline, and then the quality of interaction that leads to sales? What Does an Ideal Sales Experience Look Like? What does that look like – the ideal Sales Experience? It’s when your team understands that the potential customer they are speaking with only cares about themselves. They don’t care about the salesperson, your company or the product. They are only focused on themselves. It’s when the Discovery/Empathy portion of the conversation is the most important part. Does your team realize that everything after Discovery – when done right – is just a presentation of the solution? It’s the fact that when you combine the parts of the Authentic Persuasion Pathway (Rapport + Empathy + Trust + Hope + Urgency) that the assumptive close is all you need. If your team is having to ask for the sale they are doing sales wrong. And don’t confuse earning the right to close with asking for the sale. The Sales Leader’s Role in Creating a World-Class Sales Experience Your job as a sales leader is to ensure your team understands that the only thing – above all else – is the sales experience they provide to each potential customer. That customer knows that they have the power and the feeling of unlimited choice. Which means they will decide who to give their money to based on the experience they have with buying from a company. How can you shift your team away from the numbers game mentality to actually providing a world class sales experience to each and every person they speak with?
By Jason Cutter February 17, 2025
The Abundance of Options Today we all have lots of options. While writing this I could speak into my phone and order whatever I want. I can get food delivered before I finish writing this article. I could get a TV delivered to my door before I wake up tomorrow. When someone wants to buy something, they are armed with as much information as they want to access. They can research, read reviews, and watch videos about a product or company. The Shift in Power to the Buyer Because of this, the power balance of sales has shifted away from the salesperson and company to the buyer. Knowledge is power – and they now have all the knowledge they want. With knowing that they have ultimate choice of what to buy (internet and globalization has led to the ability to order anything you want from anywhere…so you are no longer limited to the stores you can drive to and what they have on hand), it means that everything is a commodity in their minds. Nothing is unique or special. Everything is interchangeable. Does the Sales Experience Even Matter? So, this means the sales experience doesn’t matter anymore. There is no reason to put effort into the sales process, the conversations with potential customers. No value in spending time trying to ‘help’ people – since they just view products, salespeople, and companies as interchangeable. You are not special, so there is no benefit in caring. They will walk into your store, and they will decide what they want. They fill out your online for, and they decide if they answer when you call and how the call will go. They walk up to your event/booth, and they decide how the interaction will go and if they want to listen to your elevator pitch. They will let you know if they are interested in moving forward. They will let you know how they want to buy. So, like I said above, there is no real value anymore in the sales experience. Or could it actually be valuable? Is it possible that all that matters IS the sales experience? If people feel they have ultimate information and control of the buying process, how do they decide on what to buy and who to buy from? When I search on Amazon for a product type I have never purchased before, how do I pick? When I want to go shopping for garden supplies for the house, how do I pick where to go? When I need to buy a new fridge, who will I hand my money over to? The cheapest place with terrible service? The place with reasonable prices and great service? The Sales Experience Shapes the Decision I choose based on the sales experience that I will receive. With everything else being equal, I (and I believe most people) will select the place to shop at or the products to buy online based on the experience I receive. To me all that matters is the experience. While I am trying to buy something. Once I receive it – ensure it does what I need it to do. With the feeling of unlimited choices, it can actually be harder now to buy something that in the past. People get into analysis paralysis more often. Which means that for consumers to buy something new they need help. They need a professional salesperson. They need a sales experience that matches their expectations. They want a guide who will help them make the right decision for them, with an experience that goes above and beyond what more people receive any more when they walk into a store, call a company’s toll-free number, or visit a website and have to fill out a form. If you want to succeed in sales – the only thing that matters is the sales experience you provide.
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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