CUTTER CONSULTING GROUP

E43: Q&A Week: Effective phone sales tactics and shy salespeople

December 28, 2023



Ever wondered about the key to successful over-the-phone sales?

In this episode, I answer questions about effective phone sales tactics and if it’s possible for a shy person to be great sales.



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

  • Show Transcript

    On this episode, I see if I can answer more than one single question in a 10 minute period. Welcome to Episode 43, and my goal this week is to take some of the questions that I’ve received in person, in training, online, things that I’ve read online that other people have asked in groups, and really try to answer them in the best way that I can.


    Yesterday, I was only able to get through one question with my answer, but hopefully that was valuable. I know, it was kind of a summary answer of a lot of stuff I’ve talked about over the last eight weeks as well as what I put online.


    I think a lot of the stuff I covered yesterday was valuable to answering that question about building confidence. And I know, I only got through one question went over time a little bit, hopefully, it was still valuable. If you didn’t check it out, make sure and download Episode 42.


    And if you haven’t already, make sure to subscribe so you can get all the episodes every single day they come out. But for now, whether you’re listening to this while driving, at the gym, going for a walk, you’re at work, taking a break, time to dive into some questions and see how many I can get through.


    The first one on my list today, which I’ve get all the time is what’s a simple but effective over the phone sales tactic? Or variation of this is what is the one thing I can do to close more deals?


    And it’s a tough one to answer and I know where it’s coming from. Everyone and not just in this day and age, in this era, in our current society, but I think this is probably always been true. Everyone wants to know that one key, that one silver bullet, that one way to win all the time, that one shortcut; how can I do this thing? How can I be an expert in the shortest amount of time with one strategy? What’s the one key?


    And no matter what and there are times where somebody who’s mastered something might be able to give you one word advice or one area that you should focus on, and that would be the most successful. But that’s usually at a really high level and there’s a lot of intricacies that happen within that for it to be true.


    And so when I get this question, I always try to answer it. And it’s really not one most effective way. There’s so many different things to be effective over the phone effective and sales, be a good closer, who long term as a professional is closing deals consistently and effectively.


    However, what I will say is that the top three things that I always tell people is to be authentic, be transparent and be honest. I know there’s no simple answer, there’s no like say this one thing and you’ll close deals. Like there’s so many books, and manuals, and podcasts and videos and books all out there giving you all the different tips and tactics.


    I mean, like right now on my shelf, I have a book that I bought because I was super curious about it. It’s on sales tactics and strategies for selling timeshare, which they no longer call timeshare. But selling timeshare, it’s 400 pages of step by step scripting and strategies on how to close time here.


    But there’s no one simple thing. There’s no page that says do this one thing and you’ll be effective. It’s 400 pages of scripts and strategies. And so there isn’t a simple thing. But when you get down to the basics, no matter what you’re selling, and this is universal across everything, be authentic, be transparent, and being honest, that will help you be effective.


    Will you close the most number of deals? Yes, long term, you should, deals that will stay with your company, happy clients, who will be excited and thankful raving fans who will hopefully refer you to other people. Short term, it may not seem like that works very well, but that’s always the key is to be a professional and to be authentic, transparent, honest.


    Just be authentic to who you are, to what you can do. I talked about this before I hammer on it a lot about strengths and who you are. Don’t try to be somebody else. Kind of like in the episode, the guest episode I had last week with Rob Howze, he was talking about that as well.


    He was talking about how he struggled in sales when he was trying to be somebody else and trying to put on a front and trying to be what he thought you were supposed to be in sales. Once he let that go, boom, the roof flew off and he was on off to the races and just being very effective in sales because he was who he was.


    You also want to be transparent. Transparency is so key. Every product and service out there has amazing benefits. That’s why they were created. The person who created it, or the team that created it, whatever it is, thinks it’s amazing and it solves problems. And at the same time, there are downsides to every product or service out there. There’s always something, there’s always one little thing that somebody might not like or that’s kind of a negative.


    It’s all about trade offs. You can’t have 100% good things. So, there’s going to be some downsides, there’s going to be some blind spots, there’s going to be things that aren’t great, but hopefully, the benefits outweigh those costs and that’s why somebody would buy from you. And so be transparent.


    When you’re in sales, tell the good and the bad. Hopefully, it’s mostly good and if people have questions, just be transparent. Don’t try to hide bad things because it will literally come back to bite you in the end.


    And this goes into the third part, which is honesty. Just be honest. At all times, be honest, go with that, it’s always the easiest thing to do because it’s the easiest thing to remember. It’s hard to remember that the lies you say or the things that you avoid or the games that you play with people, if you’re just honest all the time, especially if you’re doing it as your process and you’re consistent, then there’s nothing for you to worry about.


    And you don’t have anything different that you have to remember other than just the truth. And so go with that. And that’s really the one key strategy that I have for success and sales is those three buckets.


    Next question, how can a shy person become a great salesperson?


    If you’ve been listening to any of my episodes or read anything I posted online, you know that my first response to this is probably going to be self awareness, and that’s important. And I’m not going to hammer on that. But even beyond self awareness, how can a shy person be great at sales?


    Well, I think it goes back into the things I talked about in week one, which was being open and being willing. So, you really need to be open to new experiences, open to feedback, and you got to be willing to use and trust what other people are giving you and run with it.


    Shy people are hiding and they’re going to put up kind of the shy person’s version of the ego, where they’re using that as kind of the buffer to stay safe. And you really got to kind of let that go, you got to be willing to take some chances and roll with a system.


    If you’re being hired by a company, put in a sales role, you got to trust that they know what they’re doing. They’re giving you the tools that are going to make you successful and you kind of got to let go a little bit and trust a little bit and go into it with an open mind and a willingness to just run with what they give you. Just trying to do that and trust the process.


    The other big strategy and tip that I will suggest and I tell everybody this, and I know for me, it made a huge difference and kind of shifted my mindset. And I talked about this before is joining Toastmasters. If you’re a shy person and you’re kind of concerned about how that affects you in a sales role or in life in general, go to Toastmasters.


    Now, what’s Toastmasters? I’ve talked about this before. It is a voluntary club where people practice public speaking in front of other people for fun on a regular basis. Now, I know that combination doesn’t make sense. It seems like most people’s worst nightmares. It’s like why the hell would I go to do public speaking voluntarily and not at gunpoint or not because I’m required to for school or class or work, and I would do that with other people and might see that as fun?


    But I’ll tell you Toastmasters, every club I’ve ever been to, every meeting I’ve ever been to, everybody is super supportive, everyone is so nice. They’re all there with the same goal, which is to improve confidence, public speaking, effectiveness, and really communication. It’s all about communication.


    And that’s why a lot of people I tell go to Toastmasters. I suggest that to everybody, literally everybody I can, especially if you’re in a sales role management role, a training role. Because what most people don’t put together as they think Toastmasters or public speaking is all about giving speeches, and doing presentations but it’s not, it’s about communication.


    There’s so many things that you learn about how to communicate effectively, how to put together your thoughts into statements, into presentations. And when you step back, and you look at a sales career, you’re doing presentations and public speaking every single time you talk to that prospect. Even if it doesn’t feel like it, even if you’re not sitting there with three by five cards, with your topic in front of you and you’re doing a presentation, you’re standing up in front of the group.


    Maybe it’s just you over the phone with that prospect. But you have a process, you have a script, you have a goal, you have a journey of where you want them to go from here to there. It’s same thing as it would be in a presentation, same thing with a movie or a play; your goal is to go from here to that point. Toastmasters is huge, it will also build a lot of confidence.


    When you go there and you feel the support and love from a group that’s helping you communicate better, and speak in public and are there for you and giving you feedback that says we’re open and willing. Because they’re going to give you some feedback. At first, they’re going to be nice and as you go more and more, they’re going to get a little more in depth.


    They’re going to tell you all the little things that you do wrong, all the things that are keeping you from being a better communicator, all the strategies and tips you could use and things that you could be doing to help out. They want you to be successful. And it’s amazing how much that will help your confidence in life in general, but then also in sales. Because you now feel like hey, I can communicate, I’ve got the skills, I know what I can do, I know what it’s like.


    And fundamentally, I’ll tell you, most people’s worst fear in life is not death, it’s public speaking. And when you go to something like Toastmasters or any club or have any opportunity to do public speaking, and you conquer that and you get past that, which most people would rather die than do, that gives you this confidence that will then translate into so many different things.


    So that’s my suggestion. Always, if you want to build confidence, you want to build effectiveness. If you’re a sales manager, if you’re a sales trainer, all of that is presentations, all of that is communication and all of that can be benefited by going to Toastmasters or a club like that or having opportunities to speak; recording yourself listening to it. Even though that’s painful and no one likes to hear themselves speak, or watching yourself on video and then just learning how to be more effective.


    Well, that’s it for this episode. I got through two questions today so that’s pretty amazing. Make sure again to subscribe rate review, let me know any comments, any questions you have. I love to hear people’s input their feedback.


    And if you have any suggestions for future topics, not just questions, but themes for different weeks or something that you want to hear about or that you think would be interesting for you or your organization to share, make sure to send me a message you can do it through the CutterConsultingGroup.com website. You can do it through LinkedIn, just hit me up. Let me know your thoughts because if it’s something you’re looking to hear more about, I’m sure other people would find value from it as well. And 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 19, 2025
What does it take to build the ideal Sales Experience? Why does it even matter? Maybe you think you already have one. You are a professional sales ops leader. You have put everything you can in place to help your salespeople sell more. You have optimized the processes so that your sales team can focus on one thing – selling. But I promise – even if you think all of that is true, it’s not. The Reality: No Perfect Sales Experience Exists I have never seen any company or team with the ‘ideal’ Sales Experience and operation. And to be honest – I have never built one successfully. Why would I admit that? Because the ideal Sales Experience is aspirational and business, teams, processes, and customer needs/desires are constantly changing. So as soon as you put new processes in place, something else needs to change and evolve. The Scalable Sales Success Iceberg In my Scalable Sales Success Iceberg – there are 24 categories that, when built out, create a scalable sales machine – where you can add in an input and get way more output. I would love to see companies have all 24 categories set up and running optimally. But that’s not even possible – because, as I mentioned, things are always changing. Focusing on the Biggest Levers Here is the key – to build the ideal Sales Experience takes focus on the biggest levers. The ones that, when pulled, create the biggest and best results. There are many processes and systems that you can put in place – but those are going to get you a few percentage points of improvement. Instead of putting it all in here, I want to make you a special offer. Email me at jason@sellingeffectiveness.com with your mailing address, and I will mail you the book that I co-wrote with Nick Glimsdahl called Reasons Not To Focus On The Sales Experience. It will be your starter guide, facilitating the creation of your ideal Sales Experience.
By Jason Cutter February 18, 2025
The Numbers Game Mentality is a Losing Strategy Sales is no longer a “numbers game.” You cannot succeed, long term, by focusing on volume of activity. Making a million dials, sending a million emails, knocking on a million doors (the first two are way easier than that last one) is a scorched earth strategy that will sink your business. You can’t out-dial a bad sales process. It will lead to even more bad online reviews. You can’t out-email a terrible sales funnel process that requires people to jump through poorly planned hoops. You can’t out-knock your way past slimy tactics and bad products/services. The Danger of the "Every No Gets Me Closer to a Yes" Mindset The whole “every no gets me one step closer to a yes” mentally is dangerous. That mindset and strategy assumes that it’s a numbers game. That the only thing that matters is finding the right person who will buy from you. Potentially, no matter what you even say – they are just ready to buy. Not only will this destroy any online reputation you have it will also wreak havoc on your team. It is the fastest and best way to burn out your team. It will lead to a revolving door or hiring, training, and quitting as people realize how unfun the game is you have built and how hard it is to be successful. It will also feel like a mismatch – very few people (and hopefully even less over time) are long-term excited about the business model of calling 500 people a day in hopes of making a few sales. If It’s Not a Numbers Game, Then What Is It? It’s quality over quantity. [Now…note – it does take a certain quantity of activity to fill a sales pipeline. So I am not saying that your sales team can just sit and wait for people to fall into their pipeline with money in hand.] It’s about the Sales Experience. It’s about your team ensuring that they are providing the right and best experience for that potential customer – in a way that sets them up to get into the buying mood and mode. All that matters is the Sales Experience. How can you support your team in terms of the quantity of activity to fill a pipeline, and then the quality of interaction that leads to sales? What Does an Ideal Sales Experience Look Like? What does that look like – the ideal Sales Experience? It’s when your team understands that the potential customer they are speaking with only cares about themselves. They don’t care about the salesperson, your company or the product. They are only focused on themselves. It’s when the Discovery/Empathy portion of the conversation is the most important part. Does your team realize that everything after Discovery – when done right – is just a presentation of the solution? It’s the fact that when you combine the parts of the Authentic Persuasion Pathway (Rapport + Empathy + Trust + Hope + Urgency) that the assumptive close is all you need. If your team is having to ask for the sale they are doing sales wrong. And don’t confuse earning the right to close with asking for the sale. The Sales Leader’s Role in Creating a World-Class Sales Experience Your job as a sales leader is to ensure your team understands that the only thing – above all else – is the sales experience they provide to each potential customer. That customer knows that they have the power and the feeling of unlimited choice. Which means they will decide who to give their money to based on the experience they have with buying from a company. How can you shift your team away from the numbers game mentality to actually providing a world class sales experience to each and every person they speak with?
By Jason Cutter February 17, 2025
The Abundance of Options Today we all have lots of options. While writing this I could speak into my phone and order whatever I want. I can get food delivered before I finish writing this article. I could get a TV delivered to my door before I wake up tomorrow. When someone wants to buy something, they are armed with as much information as they want to access. They can research, read reviews, and watch videos about a product or company. The Shift in Power to the Buyer Because of this, the power balance of sales has shifted away from the salesperson and company to the buyer. Knowledge is power – and they now have all the knowledge they want. With knowing that they have ultimate choice of what to buy (internet and globalization has led to the ability to order anything you want from anywhere…so you are no longer limited to the stores you can drive to and what they have on hand), it means that everything is a commodity in their minds. Nothing is unique or special. Everything is interchangeable. Does the Sales Experience Even Matter? So, this means the sales experience doesn’t matter anymore. There is no reason to put effort into the sales process, the conversations with potential customers. No value in spending time trying to ‘help’ people – since they just view products, salespeople, and companies as interchangeable. You are not special, so there is no benefit in caring. They will walk into your store, and they will decide what they want. They fill out your online for, and they decide if they answer when you call and how the call will go. They walk up to your event/booth, and they decide how the interaction will go and if they want to listen to your elevator pitch. They will let you know if they are interested in moving forward. They will let you know how they want to buy. So, like I said above, there is no real value anymore in the sales experience. Or could it actually be valuable? Is it possible that all that matters IS the sales experience? If people feel they have ultimate information and control of the buying process, how do they decide on what to buy and who to buy from? When I search on Amazon for a product type I have never purchased before, how do I pick? When I want to go shopping for garden supplies for the house, how do I pick where to go? When I need to buy a new fridge, who will I hand my money over to? The cheapest place with terrible service? The place with reasonable prices and great service? The Sales Experience Shapes the Decision I choose based on the sales experience that I will receive. With everything else being equal, I (and I believe most people) will select the place to shop at or the products to buy online based on the experience I receive. To me all that matters is the experience. While I am trying to buy something. Once I receive it – ensure it does what I need it to do. With the feeling of unlimited choices, it can actually be harder now to buy something that in the past. People get into analysis paralysis more often. Which means that for consumers to buy something new they need help. They need a professional salesperson. They need a sales experience that matches their expectations. They want a guide who will help them make the right decision for them, with an experience that goes above and beyond what more people receive any more when they walk into a store, call a company’s toll-free number, or visit a website and have to fill out a form. If you want to succeed in sales – the only thing that matters is the sales experience you provide.
By Jason Cutter February 13, 2025
The Balance of Effort in Sales The blogs this week have been about the other person going most of the way. Whether it’s a prospective customer and your salesperson, where the salesperson truly can’t want the deal or make most of it happen for that customer to truly be successful. On the path for that prospect to becoming a customer, they should go at least 51/49. Whether it’s your team and their manager, the manager can’t want the team to succeed more than the team actually wants it for themselves. It’s not scalable for the coach (manager) to run on the field every play to win the game for the salespeople. What about sales ops processes and systems? What about the tools available to the sales team and the ones that are classified as sales enablement? In a reversal of philosophy, I believe the sales ops processes should go 90, the team should only have to go 10. Why Do We Need Salespeople? Let’s start where it matters – what is the point of having salespeople? I know many owners question the need and desire to have salespeople. They are hard to manage, tough to deal with, always want more money (potentially for doing less work and closing less deals), and are very resistant to change. Of course, that is a generalization. Of course, there are salespeople who don’t check those boxes. However, having worked with a lot of teams in a lot of industries, that generalization isn’t completely wrong or unfair. So if there is even a small part of that which is accurate, why would we even mess with the messiness of having salespeople? Of needing to employ and manage humans? The Human Element in Sales We need them. That’s why. Even in 2025, AI and technology has not successfully replicated the requirements of sales – which is about helping a human (prospect/customer) make the right decision and move outside of their comfort zone to buy something new. It still takes your human (salesperson) to persuade that other human. It’s why I say all the time that its not B2B, B2C, Retail, SaaS, etc. – it’s H2H. Sure, people can buy something online or even in a store without speaking to someone. But if it’s a considered purchase where there are options and decisions to be considered – it still takes a human being involved. That means ultimately your human (salesperson) has one job, and one job only – persuade the right prospective humans to buy. Minimizing Distractions for Salespeople Everything outside of that mission, task, focus is a distraction that takes away from their highest and best use. Imagine if we had a surgeon who had to prep the room, prep the patient, schedule the surgery and meetings, and do all the parts of the surgery themselves. Nope – they show up for the surgery and do what they do best. Then they take off their gown, gloves, and walk away to get cleaned up and move on to the next thing. Your goal as a sales ops leader is to support the team with systems and processes that allow them to focus on the one thing you need them for. The human part. It would be amazing if they could show up, talk to people, and make sales happen. Of course, there is more that they (and any professional) need to do before, during, and after the sales conversation. But your goal is to minimize all that. Every hour that your salespeople aren’t selling or doing sales-related activities, they aren’t moving revenue forward. The Ultimate Goal of Sales Ops What processes can you put in place that go 90 percent of the way, where the salesperson can do the last 10 percent? An example would be building an email campaign that runs automatically, and when the right people reply, the salesperson gets involved in getting that person from email to phone call. Another example would be your CRM serving up people for the salesperson to call – leads or anyone in the sales pipeline flow – with all the backstory, research, data, intel needed for them to review it then take action. What can you put into place that takes away as much distraction and effort from your sales team such that they can focus on the one thing you need to focus on – other humans?
By Jason Cutter February 12, 2025
The Danger of Doing Too Much as a Sales Leader Alright – so maybe they don’t need to go 90. In true servant leadership mode, you would go way more than 10% of the way to your team. But you have to be careful, as a sales leader. The inclination might be to do it all for them. To help them close their sales. To make excuses for them to your leadership as to why they aren’t closing more sales. Especially considering the very high likelihood that you are a sales manager because you were a great salesperson in the role that you are now managing. And there is a slight chance that you are a player-coach…so you are leading and selling. This can make it really tough not to want to run out on the field to win the game each time. But that doesn’t scale. That doesn’t lead to increased results. You can only sell so much as one person. Creating a Culture of Ownership So, you need to have people on your team that are coming to you. What does that look like? The pinnacle is a salesperson who doesn’t close a deal, comes to you right away and asks for feedback. They want some critiques as to where they could have done things better, different that would have led to the desired result – a closed sale. That takes a healthy level of ego by a professional who has the ultimate growth mindset. They know there are always ways to improve. They want to improve. And they are willing to risk their ego (and the internal, protective, primal part of our brain that doesn’t want to risk our place in the tribe) by asking for feedback that could be negative. Whenever you can, encourage that type of response. Ensure that the team knows that the team itself, and you as their leader, is a safe space – where the goal is to improve, grow, win and that everything done to support each other is done in that mode. They truly have to feel safe to share their mistakes and to get support in learning how to do more, better. Feedback That Drives Growth Part of this takes team and individual meetings that are actually filled with positive support. That doesn’t mean it’s always positive, motivational fluff. It’s not even about the shallow strategy of the feedback sandwich. Its about being real, honest, and empathetic – meaning “I see you are here, I know you want to be there, I will help you get there – even if its hard and it means saying hard things.” It should never feel mean or abusive or like an attack. But you can give some really direct feedback that will sting that ego I mentioned, but the person will know the intent behind it. The second part is hiring this type of person. Hiring people for the team that wants to win, grow, succeed. And they know that you don’t get better by being coddled, sheltered, or protected. You want people who don’t like the thought of perpetually living safely in their comfort zone. And they are excited about the opportunity to be a part of a team that pushes everyone, empathetically, outside of their comfort zone. Are You Leading or Just Managing? If you find yourself as a leader having to push your team, or going to them most of the time, or most of the way mentally – then they see you as a manager not a leader. They see you as someone who manages them, pushes them, and wants them to do things they don’t want to do. I have written some blogs here that go into what your role should be – as a leader, not a manager. Pulling people along with you, inspiring people, and supporting yourself with a team of people who want to win. Not just those that want to show up, do as little as they can and hopefully go unnoticed (yet – complain about not making enough money and how the comp plan isn’t fair, or the leads are bad, or their schedule means they can’t be successful.) Make sure your team knows that they need to come to you – at least 51/49. They should be asking for help, guidance, training, feedback, and support more than you are having to push it down onto them.
By Jason Cutter February 3, 2025
If you have seen the movie Hitch, then you know the scene. Will Smith’s character (Hitch) is trying to coach Kevin James’ character (Albert) on how to finish out his upcoming first date. He is giving him pointers, one being that if his date fumbles with her keys at the door, it could mean she wants a kiss. So Hitch wants to see if Albert knows what to do – for a good night kiss. Hitch gives him the advice “you go 90 percent, and then wait for her to go 10%” which Albert then asks “wait for how long?” Hitch: “as long as it takes.” Albert leads in, Hitch is holding back to see if Albert will wait, and then Albert goes all the way and gives him a kiss. Hitch gets upset, and says “You go 90, I go 10 – you don’t go the whole 100%.” The Sales Analogy Kissing our prospective customers is not acceptable (just ask HR!). But the concept is the same. You don’t want to ever make 100% of the effort for your prospective customers. You don’t want to be the one who is doing all the work. Fundamentally, it is not good practice to want the deal more than the other person. When you go your 90, you need to wait – as long as it takes – for the prospect to go to their 10. And I would say that you want to go somewhere between 10-49, in reality. How Successful Sales Professionals Balance Effort Successful sales professionals know how far they have to go to meet the prospect where they are, while also knowing how much effort the prospect needs to put in to show they are committed. Where most salespeople get in trouble is they get desperate. They want the sale (kiss) more than the other person and they go the full 100%. Of course, persistence is important. And you won’t get what you don’t ask for (although…if you have followed me for any length of time, you will know I am very against having to ask for the sale). But you also have to ensure that your prospects actually want what you are selling. And they want it for their reasons and their motivations. They are driven to pursue your production option(s). They must go 10, 40, 60% of the way to you. The Pitfall of Chasing Your Prospect Just like courtship and relationships – if you find yourself chasing and one-sided-pursing the other person then it means you want it more than they do. It also means they own you. You are essentially begging them for the relationship – convincing, manipulating, begging, bribing, persuading your way forward. Which means they consciously and/or subconsciously know that they are in control. Because if they say no, you will keep pursuing and offering solutions. In sales – that looks like a salesperson who is calling, emailing, stalking a prospect – making offers, offering discounts and trials, and trying to find any way to make deal work. They are going 90-100% of the way for the prospect, not requiring them to go anywhere towards the agreement. This will end terribly. If they do decide to buy – taking the discount, free trial, taking the sale bait – they will not be happy (since they weren’t bought in for their reasons), they will look for reasons confirming why they didn’t really want to buy anyway, and they will know that they own you. Your company will have to convince them on a regular basis to stay in the relationship. The Right Balance for Customer Ownership You fundamentally need that prospective customer to come to you. Not 100% where you are just an Order Taker. But potentially 51% of the way – so they want it more than you. The more you can get them across that 50/50 threshold, the more they will be a satisfied customer. But remember – at 51/49 – they still need persuading, they still need to understand the value of your product for where they ultimately want to be in their life/business, and they still need your support. They lean in the right amount, you lean in the right amount = sales magic!
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