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 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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