E13a: Fundamentals Week: Bonus Episode – Eric Nelson

December 26, 2023


Why do you think many salespeople often approach rapport-building incorrectly?

In this special bonus guest episode during Fundamentals Week, Eric and I talk about the Rapport and Empathy stages and how important they are to any sale. Whether you are selling a product or service, B2B or B2C – don’t just check off the box to move past these two stages and onto the close.

We cover the following:

  • How most reps view the rapport building step
  • Why rapport matters and how often you should build it
  • Eric’s Levels Of Pain
  • How uncovering pain leads to empathy
  • When empathy can go wrong in many ways


More Information on Eric Nelson:

Website: www.redpillsales.com

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

FaceBook: https://www.facebook.com/RedPillSales

Instagram: TheEricGNelson

  • Show Transcript

    Jason: Welcome to another special bonus episode of the Sales Experience Podcast. My name is Jason Cutter and with me today on the show I have Eric Nelson from Red Pill Sales among lots of other things that he’s all over online. As always I’m going to put a bunch of links that he is given me on where you can find him, his book training, LinkedIn, everything that he’s been producing, awesome content. Literally on the same path where I’m on with just the goal of transforming the sales landscape which is kind of how we connected both synergistically on one what we want the really the sales profession to look like and to operate in and how people to feel. So I asked Eric to come on the show today because I wanted to have a conversation that fits in really nicely with the fundamentals week I have on the show going on right now. When he and I were talking, really wanted to discuss rapport and empathy steps, how that fits in with sales and why that’s so important. Eric, welcome to the sales experience podcast.


    Eric: Jason, thank you so much for having me. It’s an absolute pleasure to be on your show. It’s so fun too because we’re both on this similar journey going down similar paths, on similar timelines. Although you’d beat me to the book process by a bit here. Mine’s not quite done, but podcasting and all these different things, which is fun. So for today for the people listening to this, I wanted to just cover more. I spend my time by myself, just talk into the microphone. But let’s chat about rapport first. Now in the first 2 episodes of fundamentals week, I covered how to build rapport and how not to build rapport. Let me just throw this wiffle ball, t-ball out there to you.


    Jason: Why do you think salespeople do reports so wrong?


    Eric: So 1 of the things that I’ve noticed with rapport and being in B two B and B to C sales is that a lot of sales people are given a script and in the script, they’re given an outline saying these are the things that I want to accomplish. Here’s my rapport step, or here’s my opening step. Here’s my rapport step, here’s my agenda step. Well, a lot of people, they think rapport is just 5% of the conversation. I built rapport, asked them how the weather is, how are things going? Where am I calling you from? Then they just get into the meat and potatoes of the conversation. Then they think rapport stops. Well that’s completely wrong because you’re building rapport throughout the entire conversation. So you’re constantly going in and out of rapport, depending on what you’re saying in the conversation. So it’s not just hey, how are ya? How’s your day going? Where am I calling you from? Then let’s talk about the product. Let’s talk about how this can help you and let’s close the deal. No, cause it’s everything that you say either increases rapport or decreases were poor. Every time that you decrease rapport, you have to loop back and start building rapport up again. So it’s a very fluid thing that’s throughout the entire conversation.


    Jason: It’s so fascinating that you put it that way where a lot of salespeople think it’s like let’s say 5% of their process, you do it once you move on. I’ve noticed and really seen people do is it almost seems like a task where they’re checking off that box. I’ve got to find something where it would warm you up. Start off the conversation gently before I dive into to why I’m here and my sales pitch and just going for the juggler on my sales process. How’s the weather out there? Talk about sports and just check those things off and then jump into it. So it’s interesting you say how it’s really what you do the whole time and how you can lose it. You can do something or say something that may take a step back or lower the rapport. Then you’ve got to build it back up. But it’s a constant weave. The best salespeople I’ve seen, don’t look at rapport as a 1 time box to check, but as an ongoing part of the whole conversation, as a continuous relationship building kind of fundamental.


    Eric: Absolutely. You can use report tactically too. For example, right now I’m working with a client closing a high ticket offer, which is a coaching program. A lot of times you need to break rapport with some of these people and call them out on their BS. Why have you taken 2 years to make a decision? What’s been holding you back? So you’re really breaking rapport, you’re kind of calling them out on their deficiency, on their issues, on their procrastination. Then once they give you a reason that’s acceptable, then you can go back building up rapport again. But in order to do that, you have to build rapport on the front end in order to gain enough trust. That’s really what it comes down to. You have to get enough trust in order to be able to call them out on their crap and then you can break that rapport by calling them out. Basically break them down and then build them back up again at the end.


    Jason: Yeah. I worked for a guy of many, many years ago and he kind of explained it in overall relationship terms with anybody, but he says, kind of like beans. He used the analogy of beans in the bag. It’s like when somebody does something for you, there’s a bean and you’re just kind of filling up this repertoire of the relationship and filling and kind of stacking up points. If you do something wrong, then you lose some of those points and it take backwards. You want to make sure there’s always a positive balance of beans in the bag or marbles or checkmarks. But it’s got to be authentic. You can’t just do a bunch of fake and phony stuff for somebody. Then try to cash that in. But like you said, you’ve got to have that rapport and then the trust, which is super important.


    Eric: Absolutely. It all comes down to trust cause if you’re asking someone to make a buying decision.  Especially, what I’m doing right now with my current client is I’m asking them to spend a lot of money. I’m asking them to invest a lot of money into a program and they have to really trust me that the information that I’m giving them is accurate and that I’m actually wanting them to succeed and not just collect a commission check.


    Jason:  So you’ve done sales, you’ve led sales teams, all kinds of different experiences. What about going too far with rapport? Have you seen that before or why that would happen in your experience?


    Eric: Yes. So a lot of salespeople, especially in the beginning when they’re brand new to sales, they think, oh gosh, I need to be this person’s best friend. We need to just be buddy buddy and basically you hold hands and skip down the beach, rainbows and unicorns type thing. But that actually hurts the sale. It hurts the prospect. It hurts the salesperson. You need to have some healthy boundaries. The prospect needs to know that you’re the 1 that’s in control. You’re the 1 that’s in charge of the sales conversation. You direct where it goes. Once you have that direction, that authority belt that actually helps build your credibility and your rapport even better.


    Jason: Yeah. It’s interesting because there’s the two extremes. There’s the checking it off the box to move forward because they don’t value rapport. Then there’s going way too much in the rapport side and basically feeling like that person’s gotta love them before they get into their pitch. I talk about it in episode 12 about doing rapport wrong and when reps do it wrong and for various reasons. Like either they don’t believe in themselves or they don’t believe in their product or service they’re selling, they’re not confident or they’re not sure it’s actually a good thing that they’re selling. So they overcompensate on the friend zone side because they think that will carry the weight of their lack of confidence or the bad nature of what they’re selling.


    Eric: It’s really no different than dating it’s guy or girl. No one wants someone that’s super needy that’s gonna oh, what can I do for you? Let me bend over backwards and kiss your butt. They want someone that’s, that’s confident, that’s going to take charge, going to take control depending on the relationship dynamic. It’s no different than in sales. Sales and dating are very similar in how they work.


    Jason: It’s funny because I’ve always used that analogy as well. When we’re talking about this rapport thing, if we talk about checking off the box, it’d be like meeting someone brand new that you’re interested in, a little bit of rapport and saying and hey this is when it’s done wrong. Hey how’s the weather? Are you liking the weather? That’s great. Then going into a sales pitch about yourself and why you’re amazing and awesome and what are, you’re such a catch, but that would be right. You also don’t want to go super, super rapport mode without any action steps or at least even seeing if it makes sense. You built so much rapport even in a dating or a potential dating situation before you even know should we keep this conversation going? Cause it may not be a good fit even if they like the same restaurants or you’re talking about sports for a long time might not be good. So it’s interesting how that plus consultative sales is really similar.


    Eric: Absolutely. Rapport you can easily jump down a rabbit hole and get lost cause you can be talking about baseball or your favorite restaurant or the weather or any other thing that you talk about just in a conversation. But if you go too far with it, you lose the entire point of the conversation in the first place. Why did they cop on the call with you? Why did they set the appointment with you? They obviously have some pain that they need solved and if you just go down the rapport the entire time then you’re not actually getting to the meat and potatoes of the conversation. What’s their pain, why are they talking to you? So you really want to be able to tactfully and artfully direct your rapport building back to what the issue is for the call.


    Jason: I’m sure you’ve gotten this question and your sales leadership career a lot as well. I tell him about the good and the bad, the short bad and the long bed version of report. Then people by extension, say, well, what’s the right amount of rapport? There is no right amount. If the point of rapport is to make a friendly relationship where you can move forward and in some other conversation, then the right amount is whatever it takes for you to get to that point. While at the same time not wanting to chew up too much of your sales interaction time. I talk about this in episode 12. Where I’ve seen some sales reps go really hard on the rapport. They’re talking about it. It actually becomes a really fun conversation. They’re having a great time. Next thing you know, the prospect’s got to go because something comes up, kid starts crying, the phone’s ringing and they’ve got to take another call. They’re late for an appointment, whatever it might be, their phone battery dies. See that all the time. Or a sales rep was on the phone for way too long. Next thing you know, prospects gone, never get ahold of him again. But they got a good buddy. They’re good buds with somebody, but they don’t have anything to show for it. That’s a tough 1. Like you said what’s the right amount? It’s all about that follow-up action. What comes after rapport and moving forward with that, when that feels right. So there’s rapport and then in my mind the next part comes with empathy, which is partially asking questions, discovering, and then obviously being able to relate to that person and wanting to help them. I know you’re that kind of empathetic type salesperson where you want to move people forward. What’s your experience been on the empathy front with too little empathy, too much empathy as far as what’s effective?


    Eric: There’s really an art and a science to empathy. Empathy can be your tonality. If someone’s going through something difficult you want to have a more empathetic tone, you want to kind of lower your voice and be caring and kind. Then if someone is being aggressive and really trying to be difficult, you can raise your tone and get a little more aggressive with them and be a little sharper with how you talked to him. That’s a skill that’s developed over a long time. That’s not just something that you’re going to learn from a book or from a YouTube channel that takes practice. That’s really kind of the first starting point in empathy is really being able to almost mirror what the other person is saying. There’s a really good book called Never Split the Difference by Chris Voss. He was a FBI hostage negotiator and he talks a lot about empathy. He talks about tactical empathy and being able to mirror what the other person is saying. Being able to repeat the 3 to 5 last words that they said or the key words that they said. So that they feel heard, they feel understood. So that way you’re building that trust and that other person.


    Jason: Yeah. I think that’s really the key part for that empathy step is asking questions and then actually listening to the answers. Empathy is about understanding what the other person’s situation is that they’re going through relative to the questions you ask in the solution you provide. It’s kind of like your client that you’re talking about that you’re trying to bring on board where you have empathy for their situation, you understand where they’re at and where you see them going and the struggles they’re facing relative to the goals that they actually want to accomplish. You feel for them and you want to help them out.


    Eric: Absolutely. It comes down as well to, to pain or being really being able to understand what your prospect’s pain is and being able to be vulnerable enough to go deep into that pain with them. Because I talk a lot about pain and my podcast and my book and the other articles that I’ve written over the time, and there’s really 3 levels of pain and most salespeople will never get below the first level of pain, which is the surface level of pain. That’s the tactical reason. The reason for the appointment itself my roof is leaking. That’s your surface level pain. That’s the reason for your appointment. Well, a lot of salespeople, they’ll look at that and I’ll say, alright, well, his roof’s leaking. Here’s the solution that we have. We can patch it, we can do an inspection, make sure there’s no mold and everything else like that. But there’s a deeper reason. There’s things that are deeper than that. It’s really your job to be empathetic and to find out what that deeper pain is. Because if you go to level 2, which is your business and financial pain all of a sudden you realize that the homeowner doesn’t have a whole lot of money and the homeowner is thinking, well gosh, if I have to get my roof patched up, what happens if they discover mold up there or other damage? It’s going to wipe me out financially. I’m not going to have any savings left. How am I going to pay the bills, keep the lights on, keep food on the table? I was really counting on that money for X Y Z.


    Now I have to spend it on this stupid leaking roof. So that’s really the business financial pain. Then if you’re able to go even deeper than that, what’s their personal pain now? What’s the real issue? What’s affecting them at the heart and the soul level? Going back to the leaking roof example it’s not something that you can put off. The more you put off, the more exponentially more it’s going to cost. By the way, little Johnny has asthma. So what’s going to happen if you keep the roof a roof leaking and the mold keeps growing, you have mold spores floating around the house. What happens if little Johnny gets an asthma attack that he can’t recover from because you didn’t fix that roof. So tapping into that deepest personal level of pain. Then having the empathy where you want to solve that. It’s not just about uncovering all of that to then use it against them. It’s about actually wanting to improve their situation.


    Jason: Right. Absolutely. I also talked about using pain. It’s both sides. It’s the Jedi and the Sif. Do you want to use it for good or do you want to use it for evil? Because, depending on who you are, you can use it either way. You could really twist the knife on well do you really want little Johnny to have an asthma attack that he can’t recover from? Right. You can be really evil. Doing it the right way you’re going to say, well, we need to fix this problem so that doesn’t happen and here’s the solution that I can provide for that.


    Eric: Yeah. I think that’s 1 of the things where salespeople who give the sales profession kind of the bad connotation are uncovering pain and then using that as leverage and a way to manipulate the client into buying something that may or may not be the right solution but seems to present the right solution. Probably not for the ideal cost or something that they can afford but just leveraging that fear side and the pain so much that they get their way as a salesperson.


    Jason: Right and it just creates resentment in the end. There’s a few sales gurus out there that advocate some of the short term sales tactics. But if you really want to build a career in sales and if you want to do it the right way, use pain for good use pain does to solve that issue. If a client’s just kind of wishy washy but they really need what you’re offering and we use a little bit of that pain to push them over to get them to commit. But if it’s not the right thing for them, don’t use pain as a point of leverage just to me a sale. That’ll never work long term because even if you do get the sale today, they will wake up in the middle of the night or a couple days later or talk to their family and somebody will point out or they will realize what happened once the spell wears off. Then they’d be really angry whether they can return the item or cancel or whatever. Or they just go online, now that that’s just easy to do. It was easy a while ago, actually, I guess not that long ago where you could do some bad stuff to people, our sell things to prospects who didn’t really need it or want it without much ramification. Because while maybe there’s BBB at the time, the Internet, before it became popular and things like Yelp it was hard to really be impacted by some bad sales practices. Not like now it’s really hard to hide now.


    Eric: Absolutely. There is no hiding. They’ll have secrecy. If you’re unethical, you will be found out


    Jason: Eventually it’ll crumble. So then on the other side of the empathy conversation, we’re talking about how to be empathetic and digging deep and finding their pain. Then there’s the other side of salespeople who just don’t have any empathy. Not even just no empathy and they’re gonna use what they find out for evil, but they fundamentally just don’t even care about their prospects. Have you seen that in your, your previous careers or the times with salespeople?


    Eric: I have. Those people just don’t last very long. Honestly, sales is a people profession. If you don’t care about people, you don’t have any business being in sales. Go be an accountant, go be an engineer where you don’t have to deal with people on a sales level.


    Jason: Sure. You’re not solving sales problems, you’re solving other problems. I think it’s interesting. I think 1 key aspect that’s important for empathy to be really successful as well, and I talk about this a lot, is that you have to have some understanding of what the person’s gone through. Even if you haven’t gone through that same exact thing. Like I will never be a mom with kids and going through a certain situation. But maybe I’ve gone through similar situation, whether it’s financial, whether it’s health, whatever that might be, and some kind of empathy for what they’re going through because I can understand it. That doesn’t always have to mean that you’ve dealt with a lot, that you’re older so that you’ve seen lots of things. I mean, there’s younger people who have gone through some life and it makes them really good at working with someone in a similar situation.


    Whether mental health or whatever, selling something. They’ve been in that prospect shoes, just certain level. I remember I was working with a team of salespeople, this was a long time ago. We’re helping people who were in foreclosure avoid their auction and help them fix their situation, keep their home, get into various programs. It was interesting because most of the sales team that had been hired before I got there were early 20 some things, many of them still living at home with their parents. Then you have this family on the phone who’s crying because their house is going to auction. They literally didn’t even know how to respond because they had no idea what that was like. Nor did they understand what the people were going through and it was just a giant fail. They weren’t very successful.


    Eric: You do have to have it a little bit of life experience in order to be able to empathize with people. Cause some kid that’s had a silver spoon that’s late teens, early 20s is not going understand on any level what a family is going through, going to lose their house. But there does come a certain level where  yeah, I understand that really sucks. I’ve never been through that situation. But let me try to empathize with you the best that I can.


    Jason: Yeah. Even if I haven’t been in your shoes, I know how my product or service helps someone like you in your shoes and the goal of what it is and where I want you to be as a result of this in a more positive, better situation.


    Eric: Absolutely. A lot of times like that comes down to framing the call and the beginning, especially if you don’t have any experience with that situation. Say it’s this is where you are at right now? Where do you want to be and what are the steps that it’s going to take to get there?


    Jason: Yeah. When you take that approach, that’s more of a almost life coach mode, therapist mode where it’s not about me giving you the steps. Yes, I have a potential solution, but it’s about you, Mr. Prospect with your goals and your desires and where you want to be. Then I’m going to facilitate it. But I don’t have to tell you where you need to go. You know where you want to go. I’m just going to help you get there.


    Eric: Yeah, absolutely that’s really what it comes down to for a lot of different things that people sell. It’s not that way for every sale, but it’s that way for the majority of them. The best sales are the ones that you’re leading the prospect, but they think that they’re doing it on their own. They’re coming up with the idea on their own. So I have a quote “sales is about leaving a prospect on a journey of your choosing while let them come up with the solution on their own that you created for them”.


    Jason: Just like being in front of a therapist. A good session with a salesperson, therapy, life coach, whatever that is, is about the professional side who you are in all of those roles, asking some questions, getting the conversation going, and then the other person doing most of the talking and discovery. So for people listening for sales reps across all industries when it comes to the empathy side, anything else you can think of that’s impactful, helpful, know that’s useful for them?


    Eric: I think the biggest thing as far as empathy


    Jason: And/or the pain steps. It’s all kind of in the discovery questions. It’s a lot about asking those right questions to discover it. For example what do you use or what do you say or what have you found works well when relaying the empathy step to somebody that you care and you want the best for them versus just there to sell them crap they don’t need?


    Eric: You really need to make it known up front or you need to let them know if this product is great for you, if this product works for you, then let’s move forward. If it’s not appropriate for you, that’s fine. We’ll shake hands and we’ll still be friends. As long as you let them know I’m looking for your best interests here. I want what’s best for you. If I don’t get a sale out of this, fine. I have a thousand other people in my pipeline that will buy from me. But if it’s not appropriate for you, that’s okay. Yeah, I think that’s a key step, is making sure you relate to them somewhere in the beginning part, maybe after the rapport kind of opening section. Is that your goal isn’t necessarily to sell every person your widget. Your goal is to help people improve their situations. If it makes sense, great. If not, for me if it’s not a good fit, I will give them some steps, some instructions, some ideas, some places to go, recommendations of where they should go or should or should not do. Like stop calling all these places because nobody’s going to have what you need and you need to just go down this path instead.


    Jason: Absolutely. Perfect. Well, Eric, I appreciate this sharing. It’s so tough to cover this, the rapport and the empathy and all these various steps, the pain levels. I know you touched on your 3 levels for the pain. But uh, obviously, I know you well enough to know there’s articles, videos, podcasts, training sessions, probably hours and hours just on that on my side. I appreciate you taking the time covering this on the surface and being a part of this and on this journey to help transform kind of what the sales is all about in the community at large.


    Eric: Absolutely. It’s been an absolute pleasure to talk with you today, Jason. This has been awesome. I really like what you’re doing and I think you and I are both making a positive impact on the sales industry.


    We’re doing what we can, we’ll just keep fighting and keep pushing together in our own ways and doing what impact we can. For everyone listening, like I said, Eric has given me his links.


    I’ve got them in the show notes. There’ll be a transcription of this whole recording available so you can reread through it, find some gems. There’s things that we talked about. If you wanted to see the info on it, and you didn’t get a chance to take notes make sure to check that out. Also, subscribe, rate, share this with everyone. I keep saying this, but one of the things that’s important to me and the mission that both Eric and I have in our own separate paths is that we just want to change the sales community. So please make sure to share this with anybody you know, that’s in sales. Thinking about sales in a sales leadership management role. Do what you can to help shift that conversation towards what sales should be about, which is service to people, to the prospects and helping them off in a better situation. Make sure to subscribe everywhere that the podcast is that. But until next time, always remember that everything in life is sales and people will remember the experience you gave them.


Become a Certified Authentic Persuader

Get the ebooks to help you close more deals

Visit Selling Effectiveness for more tips and get help

Follow Jason on LinkedIn

Or go to Jason’s HUB – www.JasonCutter.com


By Jason Cutter August 27, 2025
Most businesses struggle to grow their sales teams. At some point, they give up on looking for rock stars; they just need a team that shows up every day. In fact, research shows that 52% of sales leaders list recruiting as 'very challenging,' and average sales rep turnover hovers around 26% annually. That means for many leaders, the hiring process feels like a revolving door of wasted time, lost revenue, and constant stress. Here’s how to achieve scalable hiring results without having a massive hiring team and a huge job marketing budget. What Most Companies Do They need to hire salespeople. Maybe it’s one. Maybe it’s their very first salesperson. Maybe they need 10 more. So they: Write a job post about all the things the job involves and who they are looking for, and the type of experience they feel is important Put it on Indeed and/or LinkedIn They get hundreds and hundreds of applications They freak out – stressed at the thought of going through all those submissions They have someone on the team spend hours/days going through all the submissions. Have them call and email everyone whose resume fits what they think they want. A few people respond. So they call again, to ‘check in’ on the candidates to try and get more to respond. If that works, they have dozens and dozens of candidates ready for the first interview. Someone has to then take a week’s worth of time blocks away from their actual job to do first interviews. Most of the candidates don’t show up to the call/meeting. A few candidates make it through to the second interview. The boss or sales manager takes these. Two out of the three show up. Offers are sent to the two. One takes another job because the process took so long. The company ends up with one new hire The company repeats the process over and over again, feeling like the best they can do is one to two new hires after each complete cycle of hiring madness. And it is madness. It is also the definition of insanity – doing the same thing, running the same hiring process out of some playbook that no one can point to its origin or actual stats of success. Recent surveys confirm this frustration: more than half of leaders admit they lack an effective hiring process, and many acknowledge that their comp plans don’t even align with the results they want. The result? Slow hiring, bad hires, and retention issues that eat away at growth. Most companies struggle with filling their sales team, with both quantity and quality. They probably run the hiring process like they run their sales process. They default to old-school business thinking that the only way to hire is to just get experienced salespeople to join the team. But there is a better way. I have spent over 15 years being tasked with keeping teams filled with salespeople. Whether it was for inside sales in a call center environment or work from home, to retail environments, from consumer products and services to B2B, from within the United States to offshore, this framework works, even if you have failed in the past to try and scale your hiring efforts. In working with small and large teams, the key is the balance of quality and quantity. Humans will always surprise you. I have seen the ideal candidate – on paper – be completely ineffective in the role. I have seen reps with very little experience, whom we took a chance on, completely outsell their experienced co-workers. The experience of everything that goes into hiring over 800 salespeople, this framework is designed to help you succeed no matter the size of your hiring team. Here’s how to create a scalable hiring process that doesn’t require a large recruiting team and without losing your mind wasting time on candidates that aren’t a good fit. Step 1: Hire Traits, Not Just Resumes Did you know there are three different types of salespeople? The Newbie, The Entrepreneur, The Sales Veteran (email me, and I will send you the ebook that breaks them down). First, make sure you know what you need on the team, who you have the bandwidth to train, and if you need someone that follows your playbook (do you even have one?) pretty much exactly, or are you okay with them just ‘doing what they do best’ without much structure? Next, you need to figure out the mindset traits you find most successful. A business friend of mine, a long time ago, taught me: “Hire the smile, train the skill.” Given enough time and patience, you can teach anyone how to do anything. But it's really hard to teach someone a different mindset. Most people are who they are when they are applying to be a part of your company. Here is my list, in order, of mindsets that I know are successful for sales (in any sales role, any industry, any company): This aligns with broader studies: while past performance can matter, attitude and coachability are consistently ranked as stronger predictors of sustained success. Leaders who over-prioritize experience often miss the hidden talent right in front of them. Openness Curiosity Creativity Persistence Authenticity As I tell my clients, most leaders think they just need more reps who are ‘persistent’. They blame a lack of sales results on the team not asking for the sale enough or doing enough follow-up. The problem with biasing the screening process for persistence is that if you don’t care about the other traits, you will end up with a team full of persistent assholes who don’t listen to you or their prospects, don’t care to learn anything new, and don’t try to come up with new ways to move people to the close. They just see every prospect as a nail and sales is a giant hammer in their hand, where if they can just hit enough nails hard enough, they will win. [Don’t believe me? Ever heard the phrase ‘sales is just a numbers game’? That is this mindset in action.] The last part you want to define is what type of company culture you have and what personality is a good fit? Is it a fun environment? Does everyone like to joke around? Is it all serious and focused? Is it mission-driven? Do you actually have defined, stated core values that you care about? The answers to these questions will help you determine culture fit. One area that organizations will fall short in their selection process is ignoring culture fit and just wanting people with certain experiences on their resume or skills to help sell more widgets. If not careful, it can lead to bringing someone on board who might be an excellent, technical salesperson (meaning…technically they can do the job), but they are a not a good fit for the team. “The best reps don’t just sell your product — they sell it your way.” It’s not enough to just hire for experience; you need team players. Step 2: Treat Recruiting Like a Sales Funnel Now that you know who is open to bringing on board, what that winning combination could look like, it’s time to start building the hiring process. In sales, the initial key to success is attracting the right leads into your funnel. This is the job of marketing. Not just in the steps they take, but the messages they put out there to the world. Like fishing, putting out a hook with bait on it where the right fish that is interested will want to take that bait. Marketing should be doing the same thing for your revops. Your hiring team should be doing the same thing with the job posts and the hiring process. Your goal is to write a job post, like your marketing team writes their content, in a way that your ideal candidate would read it and say “holy crap, that is me!” Part 2 is to build in some hoops. One area that I see pretty much every organization fail at is building and managing candidate lead flow. They put a job post out there, get a shit ton of candidates, go from excited ( “We have so many candidates, we will definitely find all the reps we need!” ) to despair ( “How the hell are we going to get through all these resumes, and then what about all the interviews?” ). So many orgs are not ready for the flood of applicants. And did they even want that many applicants? If you haven’t noticed…recruiting is like sales. Well, to be specific, everything in life is sales, and selling, and persuasion. So building a recruiting process is like building a sales process. Sales teams think it would be great to be flooded with leads until it happens, and so much potential business falls through the cracks of inefficiencies and bandwidth limitations. This is why we want to put in a) hoops and b) templates for our hiring process. Let’s start with hoops. Think about it: in sales, 63% of managers admit their teams do a poor job managing the sales pipeline. If you can’t expect discipline in pipeline follow-up from a candidate during the hiring process, you certainly can’t expect it once they’re in the field. The hoops should be similar to what your prospects have to go through to become a customer. The logic is that your salespeople will run that process with their prospects, so you need to identify those sales reps who are naturally built for it. It’s similar to Alex Hormozi’s take on hiring – that what is more important than the years of experience someone has, is evaluating and selecting for traits like intelligence, work ethic, adaptability, and coachability. This is what we want our hoops to do – help the candidates show us what they are really made of. Some hoop examples: Do you require your sales team to use scripts? Yes, yes, yes…I know…salespeople shouldn’t use scripts…scripts are bad…scripts make everyone sound robotic…scripts are the problem. Bullshit. You are wrong if you think that. Alright…soap-box-moment over…back to scripts. If you require your reps to use scripts…let’s say for an intro, elevator pitch portion, compliance/disclosures – then one valuable hoop to put in place is to make your candidates memorize a short script in the hiring process. There are many ways to do it [email me, I can give you some examples of how, when, and what for this hoop], but it is an amazing filter for candidates. This is how you filter out the people who are not open/curious (remember, my top two sales success mindset traits above) – because they will decline your requirement to memorize the script. Or they will take the script, say they will work on it, and then disappear into the wind, never to be heard from again. And…that is the perfect result. I promise, no matter what fantastic story they spun on their resume or tried to present to you in the interview…their resistance to this step is all you need to know. Truly. The ones who say, “ Sure, sounds good, I will memorize this and get back to you, ” are the ones you want. Not because they are actually good at memorizing things – because I know I am terrible at it – but because they are willing to do it. A tiger can’t change its stripes. Is it a short sales cycle or a long one? If it is more than a one-call close, then you want to put hoops into your process that will help differentiate the short-term commitment versus long-term commitment people. Some salespeople out there are just too impatient to handle making follow-up calls, delays by stakeholders, and rejection after long sales cycles. They need immediate gratification. (and here is a contrarian thought…they are probably also single…because how someone is with work, they are in their life. If they can’t handle long sales cycles and long-term relationship building in a sales role, they probably aren’t very good at it in their personal life. And that’s okay…there is nothing wrong with that mode. The question is – is that what fits your sales cycle/length/mode? If you need reps who can do more than build enough rapport to sell someone something in the next 20 minutes before never seeing them again, then filter those people out by adding layers to your hiring process that extend the length. Now, I am not saying that if your sales cycle takes an average of six months, that your hiring process should do the same, but it should be relatively long. Definitely don’t interview people and then have them start the following Monday. Is there a lot of follow-up in your sales process? Do you expect your team to actually manage their pipeline of valuable leads to ensure they close? Then you want to build in a hoop that requires candidates to follow up with you. We want to test them on how well they will treat their future sales pipeline. If they won’t even follow up with you on their progress in the process, then they aren’t the type of salesperson who will follow up on their own leads. Or, they just don’t care that much about this job. Either way, this is a perfect filter to remove those candidates from your pipeline. If you want my ultimate filter process/scripting for this hoop – email me with the subject “ candidate follow up, ” and I will send you what I have done to successfully apply this filter. While that might look like a lot of hoops and processes to build out, it doesn’t take much to both eliminate the candidates who are not a good fit and allow the ones who are to raise their hand so you can pick them. Remember, no matter how desperate you may feel you are – needing to fill your sales team today, it’s never worth bringing on bad hires, especially in a sales role. The cost of their onboarding, training, combined with the cost to your leads (aka – the wake of revenue and reputation destruction that is caused by terrible sales reps speaking with your hard-earned, expensive leads is almost immeasurable) is not worth it. Fight the urge and bad business advice to just get butts in seats. And I guess that you are here reading this because you have already tried that mode and it failed. And with annual sales turnover costing companies millions, every wrong hire creates a hidden tax on growth that most leaders underestimate. Mads Faurholt-Jorgensen spoke about it in his TEDx Talk titled “ How To Master Recruiting ” with a focus on hidden talents over resumes. He called it the “whispering talents” – and in sales, we want that person who just automatically does the sales activities with the right mindset that fits your organization, sales process, and target customer type. TL;DR Most companies hire salespeople the same broken way: post a generic job, drown in resumes, waste hours interviewing, and end up with one shaky hire. It’s slow, costly, and sets teams up for turnover. The fix? Stop hiring based on resumes alone. Instead: Hire traits, not just experience (openness, curiosity, persistence, authenticity). Treat recruiting like a sales funnel by writing magnetic job posts, adding “hoops” that filter out the wrong candidates, and testing real-world behaviors like follow-up. This approach flips hiring from chaos into a scalable system—so you attract the right reps, faster, and avoid the expensive revolving door. In Part 2 of this series, I’ll show you exactly how I scaled this process to hire 50 salespeople without the chaos—complete with templates, filters, and lessons learned. Don’t miss it. And if you think that there might be some ways to improve your hiring process, contact us and we can do a free Hiring System Assessment to determine where the biggest impact can be made to help you fill your sales team.
By Jason Cutter February 26, 2025
How Can You Predict The Future Of Sales Ops? One of the keys to sales success is to be able to predict the future – what that other person is thinking, what they might say, what they will experience, how they will feel about the product/service. But what can you do – from a sales ops leadership perspective – to predict the future in masse of all the potential customers that will flow into and out of the sales process/funnel? That is a really tough one, but it is doable. Meeting Prospective Customers Where They Are The key is to always meet the prospective customers where they are and with the experience they hope to find. It’s a common theme now in these articles because it’s important AND widely disregarded – your potential customers do not care about you, your sales team, your company, your industry. They don’t care about your stats, your testimonials, your logos. They don’t care about your mission statement or your values. They only care about themselves. They also firmly believe that there is currently unlimited choice for any product/service, which means that everything in their mind is a commodity. Easily replaceable and interchangeable. Nothing (other than iPhones…which you can only get from Apple) is special to consumers unless they feel like it should be special. Are You Still Making It All About You? There is a good chance you are still running a marketing, sales funnel that is all about you. I bet if I looked at your company’s website that from the top down it’s all about you (the company). How great you are. What you do for people. What you have done for others. I bet if I tried to speak with your sales team, I will be made to go through your process whether I like it or not. Maybe fill out a form and wait for a response. Or made to call into a toll free number, even though I don’t want to talk to someone yet. Or made to use a chat widget on a site to get started. I bet when I speak with your sales team, 70-80% of the conversation will be about them, your company, and how amazing you all believe you are. This is all fair. No one starts a company to be mediocre. The goal is to provide value and make money. The missing piece, again like I said above, is no one cares about your goals. They only care about themselves. Predicting What Customers Want From The Sales Experience Back to your mission as sales ops leader – predict what massive amounts of prospective customers are going to want from the Sales Experience. It’s why I wrote about it last week and even offered up a book for free to help in any way that I can. To succeed at your mission, you have to stay ahead of the curve of what the public, and specifically – your buying demographic, psychographic, and valuegraphics, want from that experience. Key Questions To Shape The Sales Experience Do they want to call, text, email or chat? Probably all of them…so can you offer each one? (Don’t make someone decide if they want to go through your hoops…remove all the hoops) Do they need to see pricing online – should it be available and transparent? (In most cases, yes) What sales process will be ideal for moving the most people through the sales conversation to a successful outcome? (More discovery, empathy, active listening. More front-loaded about them, not you. Use the Authentic Persuasion Pathway as your model) Who are the decision makers? Is that individual going to decide or do they need to check with others for approval? (Set them up for success, and don’t force them to make a decision in the moment – you will just lose the potential sale) What type of follow up do they want and need until they make the buying decision? What type of post-purchase follow up would go above and beyond a) their expectations and b) what others in your industry do? If there is an ‘onboarding’ stage after the sale – how can you make that actually customer centric and successful? (It is rarely both) Can You Stay Ahead of the Curve? Remember – evolution is natural. The buying public is always evolving their desired sales experience. Can you predict the future of what they want so that when they encounter your company it matches what they were hoping to find – both in the experience and the solution to their need?
By Jason Cutter February 25, 2025
How do you, as a sales leader, help your team become Oracles that can predict the future? [make sure to read the Selling Effectiveness article this week https://go.sellingeffectiveness.com/LI.2.25.AM ] There are five ways to facilitate their Oracle-ness. Be Present in the Moment First, you have to get your salespeople to be in the moment. The challenge that most salespeople (and…humans, for that matter) experience is they are always thinking ahead. Salespeople default to thinking about what they will say next. The next part of their script or process. The next question they want to ask so they can get through discovery. The next part of the agreement they need to discuss and review. Their mind is too busy thinking about what they are going to say and do next, that they aren’t present. As weird as it sounds, if you want to predict the future you must be present. I have said this for decades: the moment you no longer need to think about what you are going to say/do next and can actually be present with your prospect and truly listen to what they say (and don’t say) – you will become a sales professional. Master Active Listening Second is Active Listening and paying closer attention. It’s actively listening…it’s taking what I mentioned above and putting into place. First step is to be present, second is to actually listen. For what they say. For what they aren’t saying. For changes in their tone. For when they are talking to someone on the side – who are they talking to, and is it about your sales conversation? If you sell in person, reading their body language and facial expressions. You must help them develop an almost sixth sense of listening (and yes, I know hearing is one of our senses…but this goes beyond hearing…it’s truly, deeply listening). Ask Better Questions Third, is to help them ask better questions. So many people in sales ask the discovery questions they are required to ask in order to check the discovery ‘box’. Or, they have done sales long enough they know all the answers, they think they know what everyone wants and why, so no reason to even ask questions. [Note – this type of salesperson thinks two dangerous things: 1 - everyone is the same and wants the same thing, 2 – people like to be sold to.] When your team asks better, deeper discovery questions with a focus on uncovering the what and the WHY, they will get better answers. Remember this – when you ask the right questions and you listen close enough, each prospect will tell you EXACTLY how to help them buy. Build Up Experience Fourth, build up experience. If you want to predict the future it comes from enough experience to know the probability of what will happen. For example, when I am in a season of commuting from home to an office, I am the type of person that can predict exactly what will happen on the freeway. Which lane is always faster around certain exits, which lanes always slow down, how much leaving five minutes later can make the drive suck a lot more. How do I know what will happen on a freeway with hundreds and hundreds of random people? Because of experience (and the fact that most people are just going through the motions in life so they become predictable). The more experience your team has with sales scenarios, they more they can predict the future. I generally see that it takes about six months for most people in a new sales role to have seen enough scenarios where they can start to know what will come next before it happens. Trust Intuition The fifth and final trait to help them with is intuition. One definition of intuition is “a thing that one knows or considers likely from instinctive feeling rather than conscious reasoning.” It’s that feeling you get when you know something, even if you cannot explain it. It’s what Malcom Gladwell wrote about in Blink! It’s what we do very well as humans, even if we don’t listen to it. The more you can help your team tune into their intuition and listen and trust it – the better they will do in helping persuade that other human. This goes back to the first suggestion – about being present. When your team trusts they know what to do and say next and they are mentally living in the moment with that prospective client, they can let their intuition guide them. Conclusion When I do trainings, public speaking, facilitating meetings, interviews, and sales – this is my main key to success. I trust and know that I have the experience to handle whatever comes my way in the present moment, while also knowing the destination I am heading towards. I can be present, let that experience and my intuition guide me instead of getting stuck in my head and worrying about what I will say next. Get your team to do some or all of these five steps – and they will become an amazing Oracle.
By Jason Cutter February 25, 2025
The Oracle’s Role in The Matrix If you have seen the Matrix movies, starring Keanu Reeves (as Neo), then you are familiar with an Oracle. In the movies, the Oracle knows what will happen. She has seen it, and it is predestined. In the Oracles mind there is no such thing as free will. In the first Matrix movie, Neo goes to visit her and knocks a vase off the shelf, and it hits the ground and breaks. Right before he hits it, she says “Don’t worry about the vase.” Neo says, “How did you know?” Then the Oracle responds with “What’s really going to bake your noodle later on, is would you still have broken it if I hadn’t said anything.” Becoming an Oracle in Sales Your mission as a sales professional is to be an Oracle for your prospects and clients. To know the future. Then be able to see around corners, as they say. Which means you know what is going to happen before it happens, because you have enough experience that you have become a psychic. You want to be able to predict, with amazing accuracy: What will happen next What will happen after that What issues will pop up What your prospect/client is thinking before they think it What concerns they might have before they have them Eliminating the Fear of the Unknown During your presentation/demo you want to set the expectation of what is going to occur next. Remember, humans fear the unknown. They want to avoid risk as much as possible. Your sales presentation is risky and dangerous and very unknown. They don’t know if you have good intentions or not. Are you going to persuade them? Are you going to try to manipulate them? Are you going to overcharge them? Will you actually care about what they need and want? Dealing with salespeople is so scary. Yet they still need and/or want something, so it’s the dangerous game they must mentally play. Guiding the Buyer Step by Step When you explain what you are going to do in part 1 of your process, and then what that part is done you let them know the plan for part 2, and so on – they will be at ease in the moment. They will feel like they have control over this portion, that there is an exit they can take if they don’t want to proceed. That level of control will help them accept the risk of part 1, and part 2, and part 3. Tell them what you will do. Do it. Tell them what you did. This will validate that you can be trusted. Predicting Thoughts and Feelings The next level is being able to predict what they will think and feel before they do. You can use this information in your presentation (without telling them what you are doing). You can also verbalize it, which could sound like “I am guessing from experience that you are probably wondering about _____, so let’s cover that right now.” Or “most people I speak with ask about _____.” They will think – wow this person knows what I am thinking, he/she is in my mind! And that’s a good thing. A really good thing. Conclusion The more they feel like you know what you are doing, know what they are thinking, know what they are afraid of – the more they trust you as a Guide. Because Guides only know what they know because they have helped other Heros successfully accomplish their journeys. Your mission as a sales professional: Become an Oracle.
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?
Show More