CUTTER CONSULTING GROUP

E194: Growth Through Sales with Sean Sheppard – Part 3 of 4

January 8, 2024


Why is it crucial for businesses to deeply understand the mindset and preferences of their customers?


This is the third segment of the conversation I had with Sean. 


In Part 3, Sean and I talk about:

  • Truth + Emotional Intelligence
  • Keeping things simple to solve your prospect’s problem
  • Understanding the five main groups of human behavior
  • Knowing your metrics for moving forward (winning)



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Connect with Sean on LinkedIn


Sean’s Bio:

Sean is a serial entrepreneur VC and co-founder of GrowthX and GrowthX Academy, with three successful exits, who has successfully grown dozens of early-stage companies across a wide variety of products and markets. He was recently named the #2 Online Sales Influencer and contributor at The Huffington Post. He’s now committed to working with countries, companies, entrepreneurs and those who want to work with them on building startup ecosystems and developing the next generation of leaders for the innovation economy.


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  • Show Transcript

    Jason: Alright. Welcome back to the sales experience podcast. Welcome to part three of my conversation with Sean Sheppard. As always, make sure to subscribe to the show so you can catch all these if you haven’t yet. Get part one and part two. Listen to those first so you can hear this continuation of our conversation, but without any further adieu, here we go. Sean and I diving into the third segment 


    Sean: Is because everybody wants that easy button that Apple provides you today but they don’t understand or Amazon, they don’t understand how hard and difficult that is and Amazon is the most valuable company in the world. They don’t make shit except all of us happy.


    Jason: Yup. Make it easy and simple for us to get things that we want.


    Sean: And so you want the optimal experience. That’s the optimal experience. You go into the conversation with a strong value hypothesis about how you think you can help someone and why you think that and then begin to have a conversation to validate that and then create less work and more value through the process, not the other way around.


    Sean: All too often I see the complete opposite and if you are trying to pursue the truth, you have to get people to be honest with you and in today’s market, people will not tell you the truth if it creates more work or conflict. So you have to avoid both of those things. Create an environment where it’s easy for people to give you feedback. That’s part of the growth mindset. Feedback is a gift. Remove the word rejection from your vocabulary. Replace it with feedback and embrace it and behave in a way that allows people to say, yeah, I want to tell you the truth. I can’t wait to tell you. It feels good to talk to someone about these things. That emotional intelligence, care attribute and developing that emotional intelligence aspect of who you are is a critical part of that. But that’s an ongoing experience.


    Sean: You can’t just do this stuff every time you feel like it or you think about it every single day. You need to be learning. You need to set aside time. Don’t listen to the freaking radio on the commute. Pull up the podcast like sales experience. Right? Or something like that. Learn something new. There’s no distinction in the innovation economy between personal and professional development. Do you want to be a great professional? You’d be a great person and you focus on that and you will get there. That’s my sales professional. 


    Jason: Right. So it’s interesting too that you’re talking about making it easier and not harder. I do see that a lot where companies, they don’t quite understand. I mean they think it’s easy cause they’re in it, right? They’re product designers, they’re engineers, they’re creators. They think it’s easy because in their mind it’s all simple.


    Jason: They created it, they know how it works, they over-engineer it, but it’s still, it all makes sense in their brain and it solves a problem that they are excited to focus on and not thinking about the end-user. And then the salesperson is taking that and trying to sell that and overwhelming that prospect, that potential customer, which like you mentioned early on, the lizard brain is what motivates and drives a lot of us and that lizard brain, that primal brain is still imagining a hundred thousand years ago in a cave where afraid of change and buying something has changed and if you’re causing somebody to have to make a change, which is the sales process in a nutshell, and it’s going to be more difficult to get them to see how it improves their lives. Just because you’re excited doesn’t mean anything, then you’re going to have a tough go at it.


    Sean: I’m glad you brought that up. Especially the word change. I tell all of our companies and anybody who listens when I do these workshops and keynotes around the world and all the rest is your number one competitor isn’t some other company or some incumbent. It’s the resistance to change. People naturally do not like or want change. And so when you’re taking something someplace new, you have to recognize that and only focus on working with people who share an innovator or early adopter mindset. Stay away from the mainstream in the skeptics and the laggards because they will eat up your resources but never deliver anything in return. And you have to be ruthless with your own time and how you share it and who you invested in because you don’t have a lot of time. You do no one any good, including yourself in your own family and those that you support much to say nothing of the marketplace itself by wasting your resources in areas that aren’t going to help you stay alive.


    Jason: Yeah, and that’s very important to keep in mind as you’re talking about the stage of which accompanies at. So if nobody knows who you are or your product or your service, maybe you’ve created something new, there’s no brand awareness, maybe you don’t have a lot of social proof. You need to find those people who would like to wait outside of a store for hours to be the first one to buy that thing, to say that they bought that thing right when they could have waited a week and paid probably less and not had to wait. 


    Sean: So Geoffrey Moore calls it everybody who was interested. Again, the dynamic of taking a product to market for the first time needs to read Geoffrey Moore’s crossing the chasm or at least get the book summary and understand the five communities of human behavior and how they respond to risk and change and what you just described as the innovator.


    Sean: That’s the person that goes out and buys the latest greatest thing. Even though it’s twice as expensive as it will be in a year and half as good as it will be once all the bugs are worked out. Most people in business, however, don’t have budgets and there’s a reason they don’t have budgets because people don’t trust them. That’s right. But you know what they are great at? they’re great at providing product feedback and they’re very, very useful early on. So when you’re working on features and functions and use cases and trying to understand how people are going to use your product or service, that’s where it’s most effective. But the people that are gonna help you the most are the early adopters. The early adopters are the people that have a strategic interest in helping you become successful because they see an order of magnitude change or transformation in their own life, in their own world.


    Sean: If you succeed with them and they have budgets, they may not have big ones, but that budget’s big enough to build a business and there are enough of them. Now they’re, you know, typically you’re talking about collectively innovators are about one in seven, one at eight people, and early adopters are about one five people. So you’re talking about less than 20% of the market. And we’re not talking about organizational psychologists, we’re talking about individual psychologists. So as it gets complex and you’re selling into multiple people in a large enterprise, right? The average enterprise sale is about seven influencers involved in making decisions. Only two of those seven, just statistically speaking, would even meet the pre chasm, profile that you should be looking for as part of what we call your initial customer profile, which is a very different thing than your ideal customer profile in three or five years.


    Sean: And that’s one of the dynamics that companies and founders have to struggle with. They go out to their investors and they go out into the world and they say, if we get this much of this market, this is what we’re going to be worth. And this is how this all works. That assumes a lot. That assumes that you’ve crossed that chasm and that you’ve gotten innovators and early adopters. Well, you can’t get there without them because the mainstream will not buy from you until they have referenceable use cases from other mainstream players. And they’re not going to get those until you are in a place of maturity with innovators and early adopters even attempt that. So it’s very important to identify those people, flag them early and often and only work with them. And if they don’t exist in an account or an opportunity right now, move on.


    Sean: Because the last thing you want us to spend 6, 8, 10, 12 months on a deal that just goes dark. It never goes anywhere. 


    Jason: And fighting those, you know, late adopters and the people in the middle who literally need tons of convincing and they’re not going to be the first one to take the risk and they’re not going to be the one to put their neck on the line without valid proof. You’re going to spend all your time convincing them when you don’t have the time or the resources. 


    Sean: Like the old adage you, no one ever got fired for hiring IBM. And that’s fine. And so if you take that scenario that we just talked about and you played that out, hopefully now people will understand why knowledge, skills, and behaviors and attributes necessary to be successful in this economy are what they are.


    Sean: Because in order to identify those people, you have to have strong business and market accuracy. You have to have strong emotional intelligence and great communication skills to be able to articulate to people to get their attention. You have to be an amazing cross functional communicator between the market and the product team and everybody else who’s involved in learning from that. You have to be able to embrace ambiguity that you have to have a love for helping people get what they want and you have to be strategic enough in your mindset and your thinking to look beyond not just the person that you’re trying to help, but how they’re measured in their role and how their boss’ and their bosses’ boss and their boss’s boss’s boss and their investors and then their customers and so on, all the way through to see the forest through the trees.


    Sean: Because if you can’t do that, your chances of being successful in this area with limited time, money, resources go dramatically down. 


    Jason: Yeah. It’s interesting because the clients that I work with, the salespeople are just thinking about how their product solution can help that business. Right, and they’re thinking very narrow. I’ve been training people and telling them, what does your prospective customer, that individual at that company, what keeps them up at night, what wakes them up at two in the morning worried or wondering what their boss is going to call them out on or ask them about or could, you know, push them on at any moment and how can you solve that to make them the hero, right? And then just keep pushing that up the line instead of thinking, well, I have this thing that’s amazing and you should want it. Right? Think about that other person.


    Sean: It’s what I call finding fit. Everything is about finding fit. At this stage, we’re not trying to sell anything to anybody. What we’re trying to do is seek fit. See if you’re a startup and you have one person responsible for building a product and another person responsible for building a market, how many people can you actually freaking talk to everyday? Not many. No. So in what metrics are going to guarantee that you get to that next round of money or that you get to break even so you can stay on the field longer or some interim step? Can I get two or three paid customers so that I can demonstrate that whatever it is, we call it a market milestone. You establish a market milestone by reverse engineering your funnel from the bottom up. Number one, you define an organizational objective. You turn that into a definable win.


    Sean: Like I said, maybe three proofs of concept that are paid, maybe three free pilots, maybe converting free customers to pay customers, maybe doing 30 customer interviews with key profiles that you’ve identified or personas you’ve identified. I dunno picky right? Yeah. Maybe it is a revenue number, but it’d be based on something thoughtful though is predicting revenue results and forecasting revenue on a future when you don’t have a past is bullshit and a waste of everyone’s time. Yeah, so it needs to be traction-based for it to actually mean something. That’s why I say like the number of proofs of concept. I say I need three customers with this profile over the next six months, and you assign a deadline timeline to it and then you build your funnel, right? I need X number of qualified opportunities to do that. I need X number of qualified conversations to do that.


    Sean: I need X number of qualified prospects to reach out to to do that. Right? And so when you’re doing that, you recognize that, alright, everything I’m doing is a hypothesis I’ve constructed based on a lot of thoughtful research and interaction and experience to determine that this might be the ideal initial customer profile and proof of concept necessary to meet those needs. So every conversation you’re having in the market needs to be centered around whether or not this person or this entity or this opportunity is actually a fit. You’d have to have a mindset of disqualifying people out of your funnel, not a mindset of qualifying. And you need to be okay with moving somebody out of your qualified opportunities and into your nurture framework or what we call it, nurture and opportunity framework, where we take them out of the opportunity pipeline qualified ops, and we put them into a qualified nurture pipeline.


    Sean: It says maybe one day down the road because they’re a mainstream customer, right, and they’re not going to give us a list. Now we know that they may say otherwise, but I’ve been through this. There’s no point right now cause all I need are three customers. I just need three. 


    Jason: You need to find those three innovative or early adopters. 


    Sean: Absolutely. So I’m going to be tight on fit, right? This is all about establishing criteria. This is why I call the mindset not selling products to customers, but recruiting partners. You need to have a recruitment mindset. When you’re taking something, someplace in it, you have a reality and you have a vision. You share the vision, you’re honest about your reality and early adopters and innovators. We’ll meet you in that Venn diagram if you share it with them in an honest way. The ones that will nurture themselves closer to you will understand, will absolutely buy into your vision, but also respect your reality and be willing to invest the two things that matter more than anything else at this stage.


    Sean: The time and the truth. That’s all I want from you. I want time and truth. I want the time of you and or X number of people in your team and I want them all to tell me the truth and if you guys do that, I promise you’ll get what you want. 


    Jason: Alright, everybody, that’s it for part three. Thank you so much for listening. I appreciate if you’re listening to these episodes, if you’re tuning in, if you’re listening to this conversation, Sean and I have because hopefully, that means either you’re on the same mission, the same path as us in building the right sales experience for success for companies and for customers, or you’re looking at sales or you’re looking at how you change your sales experience and you’re looking for tips and this is the vehicle to help you get there. Make sure to subscribe. You can also go to cutterconsultinggroup.com to find the episode, the show notes, the links, the transcript. As always, keep in mind everything in life is sales and people remember the experience you gave them.




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By Jason Cutter February 19, 2025
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By Jason Cutter February 18, 2025
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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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