E51: Q&A Week: Rewards of selling, hacks, and red flags

December 28, 2023



What is the most rewarding aspect of working in sales?

Welcome to Week 3 of Q&A mode on TSEP.

In this episode, I answer:


  • What is the most rewarding aspect of working in sales?
  • What are the most important hacks in sales you should have known earlier?
  • What red flags do prospects demonstrate that effective salespeople understand as a proper reason to abandon the sale?


If you have any sales or mindset related questions, send me a message through the contact page or via LinkedIn.

  • Show Transcript

    Welcome to Episode 51 of The Sales Experience Podcast. So excited for another week of questions and answers. Hopefully, you’re enjoying it. The last two weeks I’ve gone through different questions, sales related sales manager related, things that I know from experience that a lot of reps have asked, as well as things I’ve seen online or been asked through LinkedIn, Facebook.


    And I just thought this is a fun way to share kind of my experience and knowledge with everybody that’s listening and address different questions that come up. So here we are going to go into the third week of this episode 51. Like I said, very excited.


    Make sure if you haven’t already, subscribe, rate, rank the show, leave comments, do whatever you can to show others the value you’re getting from it. And if you have questions of your own, make sure to send me a message, you can do it through the CutterConsultingGroup.com website.


    You can find me on LinkedIn and send me a message there. I love chatting with people about sales. Like I’ve said, recently, I consider myself a sales nerd. Everything sales related psychology, behavior, selling, whether it’s business to business, business to consumer, I just enjoy all of it and the process behind it, why some people are successful, why some people struggle. Like all of that is just super fun for me and I love talking about it.


    So reach out to me, we can get on a call, we can chat online, whatever it is just love talking about sales. So also send me your questions if you have something you want me to address them but for now, let’s jump into it.


    Now the first question I have is, what is the most rewarding aspect of working in sales?


    I’m going to speak from my experience personally, for me, the most rewarding thing about being in sales is helping other people get what they want or need. So, when you’re dealing with a prospect, when you’re dealing with a customer of lead and you’re trying to convert them into a client, then the biggest thing I enjoy is helping them transform.


    Now part of that is just my own personal mission where I enjoy and love helping people transform from where they’re at now to where they’d rather be or to a better state or getting a goal or solving a problem or working through a transition. Like for me, that’s very rewarding and I do a lot of that with sales as the vehicle in the same way that some people could do it with personal coaching, life coaching various other things.


    For me, sales is that way to take somebody from where they’re at, to where they could be, should be rather be whatever it is. If that was selling cars, it’s where they want to be, something they want to own, something they’ve dreamed about owning.


    If it’s helping somebody who’s in financial struggles, it’s helping them get from a bad place where they’re at now where they’re struggling and waking up at two in the morning, and just stressed about their situation and they have no idea how they’re going to get out of it to a place where now they’re on the right path. Sleep at night, they know that they’re going the right direction, they’re solving their problems, they’re taking the right steps, and they can be in a better place. So all of that for me, that’s the most rewarding aspect.


    Now there’s the money side, that’s why most people get into sales is that cash reward. It’s the money, it’s the bonuses, it’s all of that, that drives some people. And if that’s for you, then that’s great.


    And you also know that the only way to get that is by helping other people get what they want, that’s how you get paid. And like they say, the bigger the problems you solve, or the more problems that you can solve, the more value you have, and the higher pay that you will receive. So hopefully that helps answers that one.


    Now second question, what are the most important hacks in sales you should have known earlier?


    And I get this one a lot where people just want to know the quickest way or what can I do right now, how can I be successful, what should I know so that I can close more sales and be more effective? I think really the biggest thing, and this is in the vein of what Gary Vaynerchuk has been talking a lot in the last few years is self awareness.


    I think the most important thing, and what kind of got in my own way in the first, let’s say 12-24 months of my actual sales career was that I didn’t really know who I was. I didn’t really know my sales style and I really didn’t understand how that affected other people.


    I talked about this a lot in the behavior weeks, where I covered the different types, the four different behavior and personality groups that you can kind of narrow people down into. And when I talked about the analysts, which I am, I didn’t realize what I did in my head and then how I approach the sales process.


    I used to give people so many choices when they came to me. I was in the mortgage business at the time and I would give them every loan type. I made this giant spreadsheet that, you know, it was on par with a cheesecake factory menu of choices.


    And it literally cost analysis paralysis in most of the people I were talking to, and they literally wouldn’t move forward and didn’t end up using me to either buy a house or refinance because literally I just overwhelmed them. Soon as I realized that and I was more self aware of who I am my strengths, and then also what other people want, instead of giving them what I think I want, I gave them what I think they want.


    And all of a sudden I would give them two choices or three choices or one choice based on all of the questions I asked and dove into. And then it was an intelligent discovery with an intelligent presentation, which then made all the difference.


    So for me, the biggest hack that I wish I had known early earlier on in my sales career as well as in life is just self awareness, just understanding who I was, and my strengths, and my weaknesses and where I fit in best and what I enjoy the most and what I can do even though it’s a struggle, and how to blend all that together and make that into a successful sales career.


    There’s some people who operate on a different level in sales. There’s how I operate, and everyone is kind of different, but the key is knowing who you are, because then you can apply that to anything.


    All right. Third question, what red flags do prospects demonstrate that effective sales people understand this proper reasons to abandon the sale?


    Now this one is tough to answer as a general thing for everybody who might be listening to this because your specific product or service will have its own red flags. It will have its own things that make a prospect either not qualified or not somebody who would be a good fit for whatever you’re selling.


    And I think the key is to take a general approach to this answer, which is you need to discover what the red flags are for you and your product or service. It could be financial, could be time it could be resources, could be availability, whatever that looks like you need to determine that for your specific product or service, and figure out what that is that would disqualify somebody from being a good customer.


    Because again, this podcast, my focus, all of the coaching I do and training is built around having a product or service that isn’t necessarily a good fit for everyone. It’s more of a consultative approach. or you have a product or service that could apply to everyone.


    However, there’s going to be a different combination, a different formula, a different kind of section of the catalog of menu options, right, [??? 7:19] that would apply to somebody else. So, if you’re a financial planner, yes, you could help anyone with their financial planning, but the presentation you make to somebody in this category is going to be different than that category.


    Now, the red flags that you’re going to have are going to be specific to what you have to offer and who it makes sense for and who it doesn’t. And you need to look at that and basically write all of that out and create that list in your mind as far as what to look for where you don’t want to move forward with the sale.


    Now, with that being said, a lot of times you have to be careful because I see a lot of reps, and this is why I want to address this question, even though this is kind of a general generic kind of answer to it. But the key is, is that I see a lot of sales reps, over time, they develop in their mind a list of red flags.


    Then what happens is, they go into every conversation with this list on their mind. And based on their experience, they know certain people don’t buy or don’t move forward. And then what they end up doing is prejudging prospects early on in the process.


    The classic to this is if you’ve ever gone into a jewelry store or a car lot and you’re dressed in bummy clothes, like maybe shorts, flip flops t-shirt, you don’t look the part of somebody who’s there for business who’s going to buy and you’ve observed how sales reps treat you.


    I used to do this when I would go into jewelry stores and I would be in Birkenstocks, shorts and a t-shirt. And it was interesting how many different stores the wraps that people behind the counter would literally ignore me.


    And I would wait like four or five minutes to see if they would come over, they would ignore me and I would just move on to the next store. And I would do that over and over again until I found a store where as soon as I walked in, they greeted me and they didn’t prejudge me.


    And then right there, they had my money because I appreciated the service. So, you have to be careful as a salesperson not to take that list of red flags and then use that as a way to prejudge and kill sales early on in the process because you don’t want to do that.


    Now, there will always be pre qualifying questions and things that you have and parameters where not everyone’s going to be a good fit. But you got to make sure you don’t go into that prejudging zone because somebody that you think isn’t going to buy and doesn’t meet your parameters could really be interested in could really be the right person if you had given them more of an opportunity instead of cutting them off too quickly.


    All right. That’s it for today’s episode, Episode 51 in the books. Make sure again, to subscribe and send me a message, I appreciate hearing from you. But until next time, always remember that everything in life is sales and people will remember the experience you gave them.


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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?
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.
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