CUTTER CONSULTING GROUP

E52: Q&A Week: Sales movies suggestions and managers over your shoulder [E52] Q&A Week: Sales movies suggestions and managers over your shoulder Authentic Persuasion Show

December 28, 2023



What are the best sales related movies to learn from?

In this episode, I answer:


  • What are the best sales related movies to learn from?
  • How do I get my manager to stop standing behind me when I am on a call?


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

  • Show Transcript

    Hello, and welcome to Episode 52 of The Sales Experience Podcast. My name is Jason Cutter and I’m excited to tackle some more questions, answering the best I can, try to give a specific answer to a specific question in the most general way possible so that anybody listening to this that’s either in sales, thinking about getting into sales, or as a leader of a sales team can take this information and apply it to whatever product or service that’s being sold. So, let’s get into the questions right away. All right.


    The first question is, what are the best sales related movies to learn from for sales people?


    Now, I get this one all the time, people always want to talk about it. Salespeople always like to ask what other people watch and study. And of course, there’s Glengarry Glen Ross, there’s Boiler Room, Wolf of Wall Street, those are like the big ones.


    And my advice and what I’ve always found with those is, within those movies within those three movies in particular that almost everyone is familiar with; there is so many golden sales principles and lessons. Always be closing is one of the classic ones that is in both Glengarry Glen Ross, as well as Boiler Room.


    Now, the thing is, is that you’ve got to watch those movies and understand all of what’s going on. Because there’s some really good sales tactics that are used and strategies and ways that you can help people move forward and persuade them.


    However, all of those movies can show the downside, the negative side, the bad side of when sales is done with the wrong intentions for the wrong reasons. Boiler Room, Wolf of Wall Street has the two biggest examples of that, and you’ve got to be careful.


    So, you’ve got to be able to pull out the lessons, pull out the things that work very well without getting drawn into the overall strategy that’s being used in each of those movies, that’s really not effective. Especially in this day and age, especially with the transparency available online with the internet, where that if you’re a bad salesperson, and you’re dealing with customers, at some point, you’re going to be exposed and it’s all going to be crumbling down.


    And that’s a terrible way to live, where you’re trying to go from sales position to sales position company to company, you’re trying to stay ahead of this bad thing that you’re doing constantly. It’s much easier to just always do the right thing, always sell in the right way, always focus on helping people in the right way possible.


    And there is a lot of lessons from those movies that can help, there’s some good things to use, and to say that will make you more effective. And so again, take the good and leave the bad and just use whatever you can from those. All right.


    Next question, how do I get my manager to stop standing behind me when I’m on a call?


    So, the scenario that I’m imagining with this question because this is the one I’ve heard myself literally, so many times from reps. Is that on the phone, working on a call, trying to move it forward, trying to close the deal and your manager is standing behind you, maybe with a headset on, maybe they’re just looking over your shoulder, they’re listening into what you say, maybe they’re giving you feedback, maybe they’re on whisper mode on the headset, maybe they’re giving you things you should say, things you should stop saying, they’re giving you advice, and they’re just all over you trying to help you close that deal.


    The first question I always have with this is, how well are you doing at sales? Because for most sales, people who are successful and doing well, they won’t necessarily have their manager standing over them in the same capacity.


    If you’re doing really well in sales, if you’re performing, if you’re succeeding, then your manager won’t be doing this unless you’ve asked them to because you want them to take you to the next level. Because here’s the fundamental thing is that anybody who’s good in any profession or any trade or any hobby craft, whatever that is, people that are operating at a higher level, actually appreciate more coaching and feedback, not less.


    So, when somebody is at the top of their game, they don’t think I have arrived and so I no longer need help. They think I’m at this level, I know how I got here, which is with tons of support, tons of effort, tons of practice, 10,000 hours of just putting in the work and doing things in a way where I’m getting better and better all the time.


    And so they get to that point and they go, how do I get to the next level? How do I become even better at what I do? The way to do that is with coaching, and help and support and a mentor no matter what level you’re at.


    So, top people actually seek out more help to get them to an even higher level. Tiger Woods, which he had his troubles in life for little while there and now he’s bouncing back. But at his prime years and years and years ago, it was said that he had up to seven different coaches; life coaches, mindset coach, financial coach, you know, he’s got his driving coach, his putting coach. And so everything he is moving forward to in becoming the greatest involved getting so much help to fix and support and help all the areas of his life.


    And so if you’re a top rep, you actually are probably seeking out ways to get better. So, if your manager’s standing over your shoulder and your top rep, it’s probably because you invited them there, and you’re hoping they can help you find the little things to get better.


    Now, if you’re not a top rep and your manager standing over your shoulder, it’s probably because you’re not even an average rep, you’re at the bottom of the pack and that manager is trying to help you. Now, it could come across as two different ways.


    One is that they’re there to coach you, support you, and their goal is to help you move from where you are now to where you could be and the potential they see in you. They’re supportive, they’re helpful and what they’re saying is coming from a good place inside of them, and they want to move you forward.


    The other option, and I’ve seen this one as well is where the manager is trying to control you and the process so that you can close deals, and they’re doing it in a micromanaging kind of way with authority and from their own ego. That kind of way doesn’t work too well because even if you do close the sale, it will be because of their pressure and what they were doing for you or with you are to you in that scenario, and it won’t really help you grow.


    If you have the more supportive manager, the first one I mentioned, they’re going to help you learn how to do it on your own. They’re going to teach you how to fish so you can get better at fishing, and fish on your own and feed yourself.


    They’re there because they want to support you and they want you to be successful. And you have the choice, whether it’s a supportive manager or a micromanaging manager to either have an attitude where you want to resist and repel everything they say or you want to be angry, or maybe you do what they say that you should do.


    And then as soon as they walk away, you’re mad, you go back to doing your own way. You bad mouth them to your co workers in the other desks around you. Or you take what they give you whether they’re the supportive one or not and you run with it because you know that what they’re giving you is the advice to help you win either way.


    And so you taken what you can you’ll learn from it, you use those techniques, and you get better at sales. Either one of those managers, that’s their goal is to help you get better at sales.


    And again, like the first question of this episode, you know, sometimes it’s not the best manager, maybe it’s not the best environment, you can just pull out the good techniques, pull out the good things, you learn the good lessons, leave the bad, and then use that as you move forward in your life. But again, my biggest thing when any rep ever ask me, how do I get my manager to stop being behind me or I don’t like it when my manager or the team lead or somebody you know, the mentor, the trainer is there behind me.


    First up, nobody really likes that. It’s always a little stressful no matter what when somebody’s standing behind you. I know, I’ve seen it so many times, I know the way – myself. I’m trying to type someone standing behind me, over my shoulder, all of a sudden I forget how to type and I’m completely ineffective.


    And so just know that it’s the same way that everyone hates listening to themselves talk on a recording, nobody likes having someone behind them. But take it for what it is and appreciate that that person is there to support you and they’re trying to help you win.


    Again, whether they’re being supportive, or micromanaging, whether they’re being nice about it or not, take in the good, use that to get better. And if it’s really a bad environment, move on. Find a different company to work for, a different product or service, take what you’ve got and move forward with it.


    If is a supporting environment, stop resisting it, stop fighting it stop thinking you know better because if you knew better, the manager wouldn’t be behind you. So be open, be willing, I talked about that a lot in mindset week, and just focus on what they’re doing is trying to help you win.


    And sometimes in the moment, you’re mad at your coach, you’re mad at your manager, you’re mad at your parent, you’re mad at the other person who’s trying to teach you and show you how to do it. And then once you get it, once the light bulb turns on, once it all clicks together, then you can look back and go, wow, I’m so thankful that that person did what they did for me.


    In the moment, I couldn’t stand it and I was mad and I didn’t like them. And now I’m so thankful and I appreciate that experience that I had and what they did for me, and the fact that they didn’t stop, and they didn’t let me be mediocre, right? They pushed me to a different place, to a better place to more of what I could be and I’m thankful.


    So hopefully, that helps. If you’re in that situation, try to keep that in mind, try to step back instead of the reaction, which is our ego, which is like I don’t need help. Stop trying to help me. I know what I’m doing. I’m really good at this. That’s the ego trying to protect us, right. I talked a lot about that in mindset week as well, which is our egos trying to keep us safe.


    And anyone else, any comments, any suggestions, any coaching, if you’re not careful that will be seen as an attack on us, attack on our personality, on our soul, on who we are. And of course, we’re going to get defensive and block that out. So, just let that part go, take in the feedback, whatever is valuable, use that and work on improving all the time.


    All right. That’s it for another episode. Make sure to subscribe, comment, send me a message all the same stuff I say every episode. I mean it, I appreciate it all. I’m so thankful if you’re listening to this and if you subscribe, if you’ve commented, thank you so much. And until next time, always remember that everything in for sales and people will remember the experience you gave them.


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By Jason Cutter February 17, 2025
The Abundance of Options Today we all have lots of options. While writing this I could speak into my phone and order whatever I want. I can get food delivered before I finish writing this article. I could get a TV delivered to my door before I wake up tomorrow. When someone wants to buy something, they are armed with as much information as they want to access. They can research, read reviews, and watch videos about a product or company. The Shift in Power to the Buyer Because of this, the power balance of sales has shifted away from the salesperson and company to the buyer. Knowledge is power – and they now have all the knowledge they want. With knowing that they have ultimate choice of what to buy (internet and globalization has led to the ability to order anything you want from anywhere…so you are no longer limited to the stores you can drive to and what they have on hand), it means that everything is a commodity in their minds. Nothing is unique or special. Everything is interchangeable. Does the Sales Experience Even Matter? So, this means the sales experience doesn’t matter anymore. There is no reason to put effort into the sales process, the conversations with potential customers. No value in spending time trying to ‘help’ people – since they just view products, salespeople, and companies as interchangeable. You are not special, so there is no benefit in caring. They will walk into your store, and they will decide what they want. They fill out your online for, and they decide if they answer when you call and how the call will go. They walk up to your event/booth, and they decide how the interaction will go and if they want to listen to your elevator pitch. They will let you know if they are interested in moving forward. They will let you know how they want to buy. So, like I said above, there is no real value anymore in the sales experience. Or could it actually be valuable? Is it possible that all that matters IS the sales experience? If people feel they have ultimate information and control of the buying process, how do they decide on what to buy and who to buy from? When I search on Amazon for a product type I have never purchased before, how do I pick? When I want to go shopping for garden supplies for the house, how do I pick where to go? When I need to buy a new fridge, who will I hand my money over to? The cheapest place with terrible service? The place with reasonable prices and great service? The Sales Experience Shapes the Decision I choose based on the sales experience that I will receive. With everything else being equal, I (and I believe most people) will select the place to shop at or the products to buy online based on the experience I receive. To me all that matters is the experience. While I am trying to buy something. Once I receive it – ensure it does what I need it to do. With the feeling of unlimited choices, it can actually be harder now to buy something that in the past. People get into analysis paralysis more often. Which means that for consumers to buy something new they need help. They need a professional salesperson. They need a sales experience that matches their expectations. They want a guide who will help them make the right decision for them, with an experience that goes above and beyond what more people receive any more when they walk into a store, call a company’s toll-free number, or visit a website and have to fill out a form. If you want to succeed in sales – the only thing that matters is the sales experience you provide.
By Jason Cutter February 13, 2025
The Balance of Effort in Sales The blogs this week have been about the other person going most of the way. Whether it’s a prospective customer and your salesperson, where the salesperson truly can’t want the deal or make most of it happen for that customer to truly be successful. On the path for that prospect to becoming a customer, they should go at least 51/49. Whether it’s your team and their manager, the manager can’t want the team to succeed more than the team actually wants it for themselves. It’s not scalable for the coach (manager) to run on the field every play to win the game for the salespeople. What about sales ops processes and systems? What about the tools available to the sales team and the ones that are classified as sales enablement? In a reversal of philosophy, I believe the sales ops processes should go 90, the team should only have to go 10. Why Do We Need Salespeople? Let’s start where it matters – what is the point of having salespeople? I know many owners question the need and desire to have salespeople. They are hard to manage, tough to deal with, always want more money (potentially for doing less work and closing less deals), and are very resistant to change. Of course, that is a generalization. Of course, there are salespeople who don’t check those boxes. However, having worked with a lot of teams in a lot of industries, that generalization isn’t completely wrong or unfair. So if there is even a small part of that which is accurate, why would we even mess with the messiness of having salespeople? Of needing to employ and manage humans? The Human Element in Sales We need them. That’s why. Even in 2025, AI and technology has not successfully replicated the requirements of sales – which is about helping a human (prospect/customer) make the right decision and move outside of their comfort zone to buy something new. It still takes your human (salesperson) to persuade that other human. It’s why I say all the time that its not B2B, B2C, Retail, SaaS, etc. – it’s H2H. Sure, people can buy something online or even in a store without speaking to someone. But if it’s a considered purchase where there are options and decisions to be considered – it still takes a human being involved. That means ultimately your human (salesperson) has one job, and one job only – persuade the right prospective humans to buy. Minimizing Distractions for Salespeople Everything outside of that mission, task, focus is a distraction that takes away from their highest and best use. Imagine if we had a surgeon who had to prep the room, prep the patient, schedule the surgery and meetings, and do all the parts of the surgery themselves. Nope – they show up for the surgery and do what they do best. Then they take off their gown, gloves, and walk away to get cleaned up and move on to the next thing. Your goal as a sales ops leader is to support the team with systems and processes that allow them to focus on the one thing you need them for. The human part. It would be amazing if they could show up, talk to people, and make sales happen. Of course, there is more that they (and any professional) need to do before, during, and after the sales conversation. But your goal is to minimize all that. Every hour that your salespeople aren’t selling or doing sales-related activities, they aren’t moving revenue forward. The Ultimate Goal of Sales Ops What processes can you put in place that go 90 percent of the way, where the salesperson can do the last 10 percent? An example would be building an email campaign that runs automatically, and when the right people reply, the salesperson gets involved in getting that person from email to phone call. Another example would be your CRM serving up people for the salesperson to call – leads or anyone in the sales pipeline flow – with all the backstory, research, data, intel needed for them to review it then take action. What can you put into place that takes away as much distraction and effort from your sales team such that they can focus on the one thing you need to focus on – other humans?
By Jason Cutter February 12, 2025
The Danger of Doing Too Much as a Sales Leader Alright – so maybe they don’t need to go 90. In true servant leadership mode, you would go way more than 10% of the way to your team. But you have to be careful, as a sales leader. The inclination might be to do it all for them. To help them close their sales. To make excuses for them to your leadership as to why they aren’t closing more sales. Especially considering the very high likelihood that you are a sales manager because you were a great salesperson in the role that you are now managing. And there is a slight chance that you are a player-coach…so you are leading and selling. This can make it really tough not to want to run out on the field to win the game each time. But that doesn’t scale. That doesn’t lead to increased results. You can only sell so much as one person. Creating a Culture of Ownership So, you need to have people on your team that are coming to you. What does that look like? The pinnacle is a salesperson who doesn’t close a deal, comes to you right away and asks for feedback. They want some critiques as to where they could have done things better, different that would have led to the desired result – a closed sale. That takes a healthy level of ego by a professional who has the ultimate growth mindset. They know there are always ways to improve. They want to improve. And they are willing to risk their ego (and the internal, protective, primal part of our brain that doesn’t want to risk our place in the tribe) by asking for feedback that could be negative. Whenever you can, encourage that type of response. Ensure that the team knows that the team itself, and you as their leader, is a safe space – where the goal is to improve, grow, win and that everything done to support each other is done in that mode. They truly have to feel safe to share their mistakes and to get support in learning how to do more, better. Feedback That Drives Growth Part of this takes team and individual meetings that are actually filled with positive support. That doesn’t mean it’s always positive, motivational fluff. It’s not even about the shallow strategy of the feedback sandwich. Its about being real, honest, and empathetic – meaning “I see you are here, I know you want to be there, I will help you get there – even if its hard and it means saying hard things.” It should never feel mean or abusive or like an attack. But you can give some really direct feedback that will sting that ego I mentioned, but the person will know the intent behind it. The second part is hiring this type of person. Hiring people for the team that wants to win, grow, succeed. And they know that you don’t get better by being coddled, sheltered, or protected. You want people who don’t like the thought of perpetually living safely in their comfort zone. And they are excited about the opportunity to be a part of a team that pushes everyone, empathetically, outside of their comfort zone. Are You Leading or Just Managing? If you find yourself as a leader having to push your team, or going to them most of the time, or most of the way mentally – then they see you as a manager not a leader. They see you as someone who manages them, pushes them, and wants them to do things they don’t want to do. I have written some blogs here that go into what your role should be – as a leader, not a manager. Pulling people along with you, inspiring people, and supporting yourself with a team of people who want to win. Not just those that want to show up, do as little as they can and hopefully go unnoticed (yet – complain about not making enough money and how the comp plan isn’t fair, or the leads are bad, or their schedule means they can’t be successful.) Make sure your team knows that they need to come to you – at least 51/49. They should be asking for help, guidance, training, feedback, and support more than you are having to push it down onto them.
By Jason Cutter February 3, 2025
If you have seen the movie Hitch, then you know the scene. Will Smith’s character (Hitch) is trying to coach Kevin James’ character (Albert) on how to finish out his upcoming first date. He is giving him pointers, one being that if his date fumbles with her keys at the door, it could mean she wants a kiss. So Hitch wants to see if Albert knows what to do – for a good night kiss. Hitch gives him the advice “you go 90 percent, and then wait for her to go 10%” which Albert then asks “wait for how long?” Hitch: “as long as it takes.” Albert leads in, Hitch is holding back to see if Albert will wait, and then Albert goes all the way and gives him a kiss. Hitch gets upset, and says “You go 90, I go 10 – you don’t go the whole 100%.” The Sales Analogy Kissing our prospective customers is not acceptable (just ask HR!). But the concept is the same. You don’t want to ever make 100% of the effort for your prospective customers. You don’t want to be the one who is doing all the work. Fundamentally, it is not good practice to want the deal more than the other person. When you go your 90, you need to wait – as long as it takes – for the prospect to go to their 10. And I would say that you want to go somewhere between 10-49, in reality. How Successful Sales Professionals Balance Effort Successful sales professionals know how far they have to go to meet the prospect where they are, while also knowing how much effort the prospect needs to put in to show they are committed. Where most salespeople get in trouble is they get desperate. They want the sale (kiss) more than the other person and they go the full 100%. Of course, persistence is important. And you won’t get what you don’t ask for (although…if you have followed me for any length of time, you will know I am very against having to ask for the sale). But you also have to ensure that your prospects actually want what you are selling. And they want it for their reasons and their motivations. They are driven to pursue your production option(s). They must go 10, 40, 60% of the way to you. The Pitfall of Chasing Your Prospect Just like courtship and relationships – if you find yourself chasing and one-sided-pursing the other person then it means you want it more than they do. It also means they own you. You are essentially begging them for the relationship – convincing, manipulating, begging, bribing, persuading your way forward. Which means they consciously and/or subconsciously know that they are in control. Because if they say no, you will keep pursuing and offering solutions. In sales – that looks like a salesperson who is calling, emailing, stalking a prospect – making offers, offering discounts and trials, and trying to find any way to make deal work. They are going 90-100% of the way for the prospect, not requiring them to go anywhere towards the agreement. This will end terribly. If they do decide to buy – taking the discount, free trial, taking the sale bait – they will not be happy (since they weren’t bought in for their reasons), they will look for reasons confirming why they didn’t really want to buy anyway, and they will know that they own you. Your company will have to convince them on a regular basis to stay in the relationship. The Right Balance for Customer Ownership You fundamentally need that prospective customer to come to you. Not 100% where you are just an Order Taker. But potentially 51% of the way – so they want it more than you. The more you can get them across that 50/50 threshold, the more they will be a satisfied customer. But remember – at 51/49 – they still need persuading, they still need to understand the value of your product for where they ultimately want to be in their life/business, and they still need your support. They lean in the right amount, you lean in the right amount = sales magic!
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