Episode 105 | Posted on

The Art of Selling with Matthew Kimberley

There’s a certain personality type that seems destined for a shining career in sales. These people are outgoing, charming, charismatic, and naturally persuasive. They have the gift of gab and a knack for turning strangers into friends (or customers). Surprisingly, you don’t need to have a sparkling personality to be a successful salesperson. In fact, following the best sales strategies sometimes comes more naturally to less gregarious, more detail-oriented people.

Here to explain all this and much more is Matthew Kimberley, an expert sales trainer and keynote speaker. Matthew is the founder of The School for Selling and the creator of the Principles of Professional Persuasion. Today, we’ll go into depth about sales strategies, tools that can help during various stages of the sales process, and why having a great sales technique is so important.

In this Episode

  • [00:56] – What does Matthew wish that marketers knew about selling?
  • [03:21] – Matthew talks about what he does when he goes into a client organization and teaches their sales team, discussing the importance of discipline and structure.
  • [07:03] – We hear about how a business owner can help position a salesperson to be on a level playing field with a prospect.
  • [08:43] – Scripts work to a degree, Matthew says, but they have problems.
  • [14:14] – Matthew talks about how he optimizes his sales system, which he says is a discipline more than a science. He then talks about how he uses hypotheses to figure out the best sales strategies.
  • [16:40] – Stephan points out that the idea of split-testing with hypotheses is used in SEO as well.
  • [17:52] – Does Matthew do any type of personality assessments with his clients?
  • [19:09] – Stephan is very much into personality testing, he says, and explains how he uses it in his hiring process. Matthew then elaborates on his views on personality tests in roles outside of sales.
  • [22:12] – Matthew discusses some of the ways in which technology can help hold business owners or entrepreneurs accountable.
  • [23:27] – Stephan uses two CRM systems: Capsule and Infusionsoft. Which tools does Matthew use?
  • [26:55] – We hear more about the potential of eliminating the salesperson entirely through technology through bots.
  • [31:07] – Matthew talks more about online car sales, which would have been hard to believe even just a few years ago.
  • [32:11] – Matthew mentions ManyChat and discusses how he has used it.
  • [33:48] – We hear Matthew’s thoughts on the ability to follow instructions and the idea that his job is to eliminate any organization’s dependence upon one tyrannical personality.
  • [36:25] – Why a stand-up meeting? Matthew explains why the understanding that the meeting won’t last long is helpful.
  • [37:31] – Does Matthew have any other morning rituals or routines that might help a person or a team get in the zone for closing lots of deals?
  • [41:05] – Stephan digs into the efficacy of setting monetary values for various milestones in both sales and all aspects of marketing.
  • [42:48] – Matthew talks about his webinars and the role of a joint venture partner in these webinars.
  • [44:45] – Does Matthew have any criteria for choosing joint venture partners based, for example, on the size of their audience?
  • [45:58] – We hear about Matthew’s personal morning rituals, with him explaining that most of his days started slowly until his kids and dog changed things.
  • [47:56] – Stephan explains that we each have our own chronotype and that it’s important to schedule your life around your chronotype instead of forcing yourself to conform to another schedule.
  • [49:19] – Where can listeners go to work with Matthew?


Yes, it’s another sales focused episode because sales is part of marketing after all. This episode, we have Matthew Kimberley joining us. He’s an expert sales trainer and keynote speaker, he’s the founder of the School For Selling, and the creator of the Principles of Professional Persuasion. His first book, How To Get A Grip, sold over 50,000 copies. Let’s jump into Episode 105. Matthew, it’s great to have you on the show.

Thank you for having me, Stephan.

Let’s talk about selling. You’re an expert on selling, sales training and so forth. What do you wish that marketers knew about selling?

I’ve been selling for two decades. I first started learning about marketing probably about a decade ago. Prior to that, I was on the sales floor. When I started my own company I realized that it had to do with marketing as well because selling is converting the leads and marketing is generating the leads. One of the people that I learned from is a guy called Michael Port. Michael Port wrote a book called Book Yourself Solid. I went on to do lots of work with him for about five years. We ran the Book Yourself Solid School of College Training together amongst other things. One of the fundamental truths behind the Book Yourself Solid system is that marketing doesn’t get you clients. In fact, all that marketing does is create awareness about who you are and what you have to offer the world. That’s a very bold statement. If we dig down a little bit deeper, we can interpret it as really very basic leads. Marketing gets you the leads but it’s sales that converts the leads to clients. I know lots of people who are very effective marketers. You probably know some of them as well, Stephan. People with lots of engagement, lots of clicks, lots of views, lots of fans, lots of likes, lots of retweets, lots of double taps and very few customers. I worked primarily with tiny business owners, businesses of maybe one to three people, doing under $3 million a year. There’s a lot of conflation, particularly at the lower end of that revenue scale between marketing engagement and effective marketing that leads to client conversion. I’d like to see all marketers work in tandem with their sales department. In big serious organizations, that happens very well. But certainly in smaller organizations, the one-person business or the two-person business, this idea that marketing reaches the same as revenue is something I’d like to disabuse people of the notion of.

Yeah. That makes a lot of sense. By the way, Michael Port is awesome. I had him on my other show on the Get Yourself Optimized episode number 24 for our listeners. Great episode, focused on being a more effective public speaker. Yeah, he’s very good.

Nobody better. Nobody better, yeah.

Yeah. Let’s talk about what do you do when you go into a client organization and you’re teaching their sales team? What are you teaching them?

Discipline, mainly. There are some people who are naturally inclined towards selling. Those are people who’ve been told their entire life that they have the gift of the gab or they can talk for hind legs of a donkey or they’ve got an answer for everything, they’re charming, they’re witty, they can work the room. These people are often naturally inclined towards selling. It’s essentially a people job. But what these people generally don’t have, these extroverted characters, is attention to detail. People who are not naturally extroverts had fondly enough but people who are good planners, good administrators, good at following guidelines every time tend to do  incredibly well at selling. But because they’re not naturally attracted to it, what I try to do most of the time is rain people in and teach them a little bit of discipline. I believe that sales should be boring and systematic. It doesn’t get people but I think it should be boring and systematic. We’re not looking to improvise the way around a sale. We’re not looking to ad-lib every time. We’re looking to follow a very strict process, whatever that sales process is. For every organization it will be different. Jordan Belfort, The Wolf of Wall Street teaches the straight line system. I’m not very, very familiar with his stuff, I know that he’s in demand as a sales trainer now that he’s on the market again. He teaches something called a straight line system. My interpretation of that, which may be wrong and you should go and check it out directly from the wolf’s mouth if you’re interested, is that it’s your duty to move a prospect from a to zed. That is from initial identification through to close in a straight line as possible. Like with everything, you can do it systematically. If you know that there are going to be certain check boxes that need checking off along the root, then you’re more likely to arrive at that destination quickly and with a minimum of hassle and a minimum of disruption. I really do teach sticking to sales processes. I teach CRM integrity and not trying to make it up every time. If we were to eliminate a sales person, which is being done now with bots and AI, we have a series of if this and that situation. If the customer says this then do this and bring them back to the sale or if the customer objects that then handle that objection and bring them back to the sale and so it continues. Discipline and structure is a very big thing. The other thing which is critical is positioning, the positioning of the sales person. So many salespeople deposition themselves. They put their prospect on the pedestal or they put their client way up there, metaphorically in their brains, and they automatically adapt to subservient position to their prospect. They walk in to see a prospect, metaphorically get down on their knees, sometimes their body language actually looks like they’re down on their knees. They whimper and they simper and they say, “Thank you so much for having me in here. I appreciate how valuable your time is. I promise I won’t keep you very long. If you do need the courtesy of pretending to give me your attention for just three minutes then I’ll walk you through these incredibly dull PowerPoint prospectus and hopefully manage to maintain my dignity long enough for you to show me the door.” That’s a big mistake. I think many salespeople should reposition the prospect to be someone who is on your level, who’s looking you in the eye and who is an equal. That means that when the prospect is giving you questions or they’ll file objections at you or they’re testing you or perhaps they’re trying to get rid of you, then you are not going to succumb to the power play and you maintain a little bit of dignity and your confidence is frankly more attractive and more authoritative and more likely to close the deal.

Yup, yeah. The business owner or the marketer can actually help position that sales person to be on a level playing field with the prospect, right?

Yeah, they really can. They’re the most obvious right there. This is their job titles. I remember when I first started recruitment years ago; I went to a meeting with a senior recruitment consultant. Our business cards said exactly that. Mine said junior consultant, my colleague’s said senior consultant and the prospect didn’t look at me or address a question to me. The minute my business card said something, all of a sudden I was in the room. I think there’s absolutely no harm in saying I’m sending my VP of sales to speak to you. We know that the most effective and consistent closure on any organization is the CEO. Not because necessarily that they’re the sales people but because the prospects take them more seriously. They can certainly be empowered. The salespeople can be empowered by job titles, by the way that the introduction is made in order to be positioned as a consultant who can solve your problems or an order taker who’s come to try and convince you to sign on the dotted line.

We know that the most effective and consistent closure on any organization is the CEO. Not because necessarily that they’re the sales people but because the prospects take them more seriously.

Yeah. Another thing that the company and the marketing department can do to help to position that sales person is to have them featured on the website, have a bio about them just like you’d have the executive team. You take the sales people and you really position them well.

Absolutely right. That is a great idea. Drop the hierarchy. Is it important? The only reason I would want to take a junior with me to a meeting would be to position myself and it doesn’t serve the junior, I guess.

Yeah, for sure. Let’s talk about the systems that will really help. Do sales scripts like for cold calling, do those work? Or are there other systems that you have in mind?

Scripts do work to a degree. As our mutual friend, Taki Moore, no doubt lots of other people. But I’ll tell you the problem with scripts is that the prospect doesn’t have a copy of the script. What you instead have is more of an idealized playbook. That’s why RolePlay, they’re still in great use by tele-canvassing organizations, by marketing organizations who pick up the phone and bother you while you’re having dinner. I understand why because it eliminates human error, it eliminates creativity, it allows you to hire cheap people, lowest common denominator and our simulated robots to read the script. I understand exactly why that’s done, for both. Ideally other than using a script we’re using a set of guidelines. I think choose your own adventure style script would be ideal for most organizations. But for many organizations this is beyond the pale because they’re not prepared to do the homework that goes into every possible permutation of the customer’s answer or a prospect’s answer when you ask them a question. Are you in the market for new windows at the moment? “No, thank you.” Okay. If prospect says no thank you, you ask this: why not? “Because I’m fed up with of your stupid calls.” This never appears as one of the possible permutations in your digital adventure sales script. Process is however or systematic structures are insanely useful. I worked in Timeshare selling probably a long time ago. Almost across the board, two very interesting observations. I almost crossed the board with an average closing rate of about 12%. That means that for every 100 people that came for the door who were completely called prospects, 12 of them would buy something, which was phenomenal. We were over 50 or 60 different sale representatives. Everyone’s closing rate was roughly the same. There were some permutations, some people are closing at 9%, some people were closing at 15%. Average is evened out but even month to month would have great variation. Where individually close to 9% while month to month close at 15%. At least ¼ then drop back down again. The other reason that was possible is because we were all following instruction very, very strictly. There were maybe seven or eight different points in our presentation’s journey. The presentation could take up to six hours, which we have to hit in the first hour warm up. We have spent an hour warming up the prospect, which meant no talk of why we were there or what we’ve been doing. It was information gathering, it was clarification, it was rapport building. Then we’d move on to the initial presentation. Then we’d move on to the logical reasons why people should be interested in our product. Then we’d move on to the site tool. We’d be getting a cab and we drive out to the buildings, the construction site. We’d then build in a hotel and then we come back and we’d show them a video. Then we give them a cup of tea and then we’d push all the emotional hope buttons. Then we do the close. We had to do it in that order every time. I was very heavily pleased. If we’d skipped any of those, then our closing rate shows would’ve suffered. What was really interesting is that people were more effective at the beginning of their careers than they were towards the end of their careers. It was a high turnover industry so people were kicked out without much fun fare at the end of a bad month or two. But once people were comfortable, they thought they could cut corners. They said, “Whoa. This bit is boring, I’m going to skip the video,” or “We don’t really need to go to the construction site to have a look at it. It’s going to take an extra hour and a half. I believe I can close without it,” or they’d say “I’m not going to answer these questions in the qualification form because I’m just so confident and cocky that I can close this anyway. I’m not going to bother.” We’d see that the more experienced, sales reps were actually damaging their own results by thinking they could do better than the system. Although script may not be required, a systematic process is fundamental I’d say. If you think about the way that we measure sales and sales processes that would typically be using a pipeline. We’d do them using our CRM system, using our dashboard that everybody can have a look at whether that’s online or offline. We’re going to be moving our prospects from the left of the screen to the right of the screen or the beginning of the pipeline to the end of the pipeline. Each one of those sections of the pipeline is a section of the sales process that we can’t ignore. The first one might be setting up a meeting, second one would be making a presentation, third one could be making a proposal, fourth one could be following up on the proposal, fifth one could be closing. With any each one of those, what needs to happen at the meeting? What needs to happen during the qualification process? What do we need to include in the proposal? What timeframe are we going to have for the follow up? We can break each section down into 30 sections until we have a checklist that eliminates the margin for error and insures greater likelihood of our successful close.

Is there some sort of a testing process or optimization process to get it right? Like, “Okay, we need to have a video. It needs to be this long,” or “We need to incorporate the showing of that video prior to going on site in the construction site or after it.” How do you optimize that process or that system?

Many people would say that sales is a science. I’d prefer the word discipline. But one thing that we do borrow from the world of science and scientific study is the testing of hypothesis. To be honest Stephan, nobody knows how long should a video be, who knows? Is he going to help her if we include a science, who knows? Do we really need to contact this person seven times before we give up, who knows? The only thing that we can do is lean upon previously available data, ask experts or trainers, ask people who’ve done it before and test the hypothesis. We should also be prepared to accept at what level we’ll be satisfied with the result. For example if you got a system that closes affordable leads at 15% which gives you a 120% return on investment, should you be satisfied with that or should you always be striving to improve? After a while those improvements will become negligible. You should say, “Okay. We’ve got an effective funnel, we’ve got an effective process that close at 15%.” But it all starts by saying, “Let’s do it this way” I hate this expression but it just came to my mind “Let’s hoist it up the flagpole and see who salutes it. Let’s run it. Let’s see how well it works. Then we’ll collect some data. We’ll say okay, first 100 people have done things this way. I did my first 100 calls this way. I did my first 100 pictures this way. I did my first 100 meetings this way. These are the results. Here we go. I have a feeling that if I do this, this and this differently then I’ll get better results.” You then test. You split test your next 100 meetings against the different way of doing things. Edit and that sounds very clearly, calling it handy if you have enough data. If you were just one-person who’s taking massive things five times in a row and you can’t afford to make a mess the sixth time, then maybe you try something completely different. I once sourced a guy called Raymond Aaron who’s in Canada, a great salesperson. Sales on the stage, back of the room selling that kind of stuff. Given absolutely killer presentation, he closed about 35%, 36% of the room which was unheard or that one of these free speak to sell events. I asked him afterwards what’s the secret. He said, “Secret is I’ve been doing it for 20 years or longer. Every time I see something that works, I try it in my own presentation. If it works then I’d keep it in. If it doesn’t work then I’d drop it. Of the 20, 30 years of building up stuff that works and discarding stuff that doesn’t.” He’s got what he believes is a highly effective pitch.

Oh, that’s so cool. This idea of scientific approach and testing your hypothesis, having hypothesis and then testing them, and varying only one thing at a time so that you can split test the stuff and see what works, SES’s very much like that. You don’t take it as the gospel truth, you actually test it. Make sure that it’s real.

That’s right. If you got more than one sales person, your disposal it says more than one of you doing pitches or doing meetings or sending emails. Then you can test individual protest against each other in real time.


There is the problem that what works for one person archetype won’t work for another. But if you can stabilize things as much as possible then you might find that, “Wow. Why is Stephan consistently outperforming Matthew? Is the stuff? Is the stuff, is the fundamental matter in his presentation, in his close different to Matthew’s? Or does he just have better tone of voice?” Because this is something which counts for a lot as well.

Yeah.  Speaking of personality types, do you do any kind of assessments? Personality assessments, DiSC or predictive index or Fascinatetest from Sally Hogshead, anything like that?

I’m familiar with all of them. It’s not something I’ve ever encouraged my clients to pursue. Certainly on a sales training point of view, I find that useful for a minute. Occasionally I coach business owners individually. It can be useful to find out before we get going what kind of person I’ll say I’m working with. But generally if a sales team is training then they’re all dead to one job. I wouldn’t typically advise my clients, unless their recruitment budget is enormous, to focus on a type of person. I would teach the discipline to the individual rather than try to identify the right individual for a particular role. Traditionally people will say extroverts are good at selling, traditionally, extroverts are attracted to the world of selling but certainly in the more technical sales world. It was moving away from cars or consumer goods in the more technical sales or B2Bs. Slightly more analytical, slightly more fruitful approach has never been harmful. I think you need to have the confidence to hard work. Going back to what I mentioned earlier, look the prospect in the eye and say, “I belong in the room.” It shouldn’t be someone who’s easily intimidated or coward by authority. But beyond that I haven’t found personality testing to be particularly useful.

Okay. I’m big into it. I test people before I hire them. It’s part of my selection process. Like for example with DiSC, I can see if somebody is going to maybe be too much of a renegade and not follow my instructions or they’re not going to be very attentive to detail. If the role requires that, that’s going to be a knot of it. If they’re very introverted instead of gregarious and outgoing, they wouldn’t be good for a sales role probably and that sort of stuff.

Interesting. I think probably outside of sales roles, also this is something I definitely want to look at. If someone’s going to be a project manager, are they good at finishing? If somebody’s going to be an administrator or administrative support, are they diligent at follow up and ticking boxes? What I look for more in a sales person whenever I’ve recruited salespeople is communication ability. That might start within an initial telephone screening. If I’m hiring somebody to do cold outreach or even warm outreach to individual clients, then it’s absolutely critical that they can hold a conversation because without that we’re lost. That means that they have to have a good telephone manner, that means they have to talk in complete sentences, that means they have to not um too much, that means they need to display large levels of empathy. But for sales roles that was always the only thing I look forward for financial control roles or for human resources roles or for operation management roles. Then certainly our personality test would come into play. For sales I believe that communication and an ability to follow a set of rules is all that’s required. When it comes to following rules, I don’t believe you need to be a personality type. I think it just has to be explained to you that, “Look. This is your job.” “Do I have to ask for a referral?” You don’t have to but it is your job. Aside asking, “Do I have to restock the milk in the supermarket when the shelf is empty?” Yeah because it’s your job you just have to do it. This sales discipline, the discipline of following the process is not optional. If it were up to me the computer wouldn’t let you go any further unless you could demonstrate proof that you’d asked for three referrals from everybody you spoke to. Certainly for self-employed business owners who do their own selling, they hold themselves to a much lower standard than they would hold a salaried sales person. I talk to my one person business analyst, freelancer that’s self-employed and I’d say, “How many sales offers did you make this week?” He’d say, “My cow was sick. I got distracted with moving my website header three pixels to the left. I had a ton of emails to work with.” I said, “How many sales you made?” He said, “Well, not many.” I said, “That’s a direct correlation there.” You wouldn’t accept to this answer from a salaried salesperson so don’t accept it from yourself either. We can all hold ourselves to a much higher standard of sales discipline than we do today.

I love that. That’s so true. I am guilty of those.

We all are.

Outreach to a prospect that I’ve been in communication with. Yep.

Technology helps. Technology does help to kick our butts a little bit. For using a CRM system that just says, “Hey. You got to do this now. This is flashing red. This is in danger of rotting and decaying.” or “This person’s getting likely to forget that you even exist. You should ping them right now.” Technology really is our friend. When I first got started, it was all index cards and paper calendars. Reminders to follow up at this person, reminders to follow up that person. Then of the last 20 years, CRM systems have just improved dramatically. I think anybody that doesn’t have a CRM system is a fool, frankly.

Yep. I’m not a fool.

I’ve seen very large organizations, multi, multi-million organizations that don’t have a common company-wide CRM system. I find it astounding. It’s great when they hire me, it sets it right, I believe I can make some immediate improvements. Of course it’s never immediate because adoption of new tools, especially in large organizations they have legacy way of doing things is always a bit of a struggle. You can build your own tool using a device that you paid $20 if you want to. These solutions to make life easier, at least in terms of remembering to follow up process are abundant.

Yep. I use two different CRM systems. One is Capsule and the other is Infusionsoft. Curious what is your preferred CRM? What do you use personally?

I use Infusionsoft for everything which is one to many. Whether that’s email marketing or delivery of improvised shopping cart or an Infusionsoft as well, customer looking after customers. I use Help Scout as a CRM system which integrates with Infusionsoft. If I want to, I could save every help desk to get inside Infusionsoft. I don’t because that sits next to each other quite happily. Pipedrive is what I use for manual sales. I could do this with Infusionsoft, I just prefer Pipedrive for manual one to one sales follow up. There are two sides of my business. One is selling stuff in bulk to a database of people, many of whom I haven’t met or spoken to face to face. The other part is the individual consulting, the individual coaching, the individual sales closing if you like. Pipedrive helps me do that.

Okay. We’ve got a very similar system set up to you. I use Infusionsoft for my one to many. I sell on my courses, membership site, etc. I use Infusionsoft with the email campaigns, the campaign builder and all that sort of stuff. Then for my coaching clients and for my consulting clients for a seal I’m using Capsule CRM.

Yeah. That’s a really good set up. But I’d say you don’t need everything. You could just have Infusionsoft if you want to. I believe some of the other automation tools are somewhat overly familiar with things like ConvertKit or Drip or so have very good CRM capabilities now, not just email automation. The thing that I’ve been using as a secret weapon item for the last forever is something called Contactually. Contactually, I use that purely for follow up reminders. The beauty of Contactually is it syncs with your email inbox, it syncs with your address book as does Pipedrive and probably Capsule’s well but I say, “Look. I want to stay in touch with Stephan every 90 days.” Then I’ll say, “I want to stay in touch with Barb every 60 days. I want to stay in touch with Sue every 120 days.” I just go through my entire list of contacts and say how frequently should I keep in touch with these people in order to maintain a good relationship with them. To be clear it wouldn’t more than 90 days in any one case. I tell Contactually, “If I’m not in touch with Stephan in the next 90 days, remind me.” It sits on top of my emails and says, “I don’t think you spoke to Stephan in 90 days. Time to follow up with him.” This has really served like nothing else in terms of keeping your network of important people aware that you exist. Yes, my mother is in there as well. You haven’t spoken with your mother in a week. Oops, sorry.

Very good. You’re a good son.

Well, thanks to technology.

Yeah right. That’s just a facilitator. You’re a good son who happens to set up the tool because you care.


I do love the minimum 90-day contact frequency. That’s critical, it really is.


We talked earlier about the potential to eliminate the sales person altogether through bots and AI and so forth. Talk a bit more about that. What sort of bots are you using or have you seen? Does it really get close to being able to eliminate the sales person?

No, I’m just dipping my toe in the water. I know plenty of people who are going really deep on this. People like Scott Oldford, if you said who’s your go-to guy for bots. I’ll say Scott is the person that I’ve learned the most from. I only implemented it once in my business personally. This is when I was hired to sell tickets for an in-person event or shall I say assist with the marketing of clean bots and seats for an in-person event. One thing that we want to do is offer military and veteran discount code. We set up a Facebook chat bot. I’m sure it was the most rudimentary implementation of it but I was so curious, everyone was talking about it. I wanted to offer a discount code to active members or former members of the military as an expression of gratitude. There’s a marketing tool but I didn’t want to just update a Facebook page that said, “Hey. Use this discount code.” It would’ve been abused and it would’ve seemed to be non-exclusive and we would’ve been able to get to meet people who are interested but didn’t buy. Many people opt in to get the discount code. The way they had to do that was by leaving a comment on the Facebook status update, which automatically filed a bot which says, “Hey. I’m little Matthew, your robot friend. Are you here because you want a military discount? Say yes if you are.” If they said yes, we give them the discount. We could track exactly how many people opted in for it versus how many used it. That was incredibly useful for us. This is something that I’ll definitely explore in the future. One thing that I was adamant about is that it wasn’t going to be about pretending to be a person.


That makes me feel sick. I was adamant about that. The introduction was on a robot. I think you say it can help my feelings, yeah. If you want you could speak to a human, just type speak to a human. I’ve seen it in use very effectively for diminishing cues and for support tickets, which is absolutely a part of a pre-sales support. Do you have any questions or anything that’s stopping you from buying? That’s one person to go as far as to say, “Is it the price that you don’t like?” Yes. “If I could offer you a price that was 20% better, do you think it’s something that you do right now?” Yes. “Do you promise?” Yes. “Okay. Use this code to check out.”

Oh, nice.

Anything that could be programmed could be included. I think tone of voice is important, I think the way that you position the bot is important. I guess it’s how many things can diminish help desk inquiries. Could this be answered by a robot? This is a question you should be asking yourself when you’re running pre-sales support anyway. That’s why we have FAQs, that’s why we have pop-ups on our page which have to be manned sometimes but people would tell them, “Hey. It’s actually Matthew here. I see you’re on my page. Do you want to buy something?” These are very useful. I can’t remember what it’s called, is it called proof or you might be able to tell me this. I’ve seen recently on sales pages kind of social proof style that pops up and says, “Hey. This person here just bought this thing, which is automated social proof thing.” I think they’re absolutely fascinating. I think for some sales, I’m sure test that get by without ever using a sales person five years from now. I think it’ll probably do probably 50% or 60% of the sales without human intervention. “Right now can I order in fully mode a car online?” Yes. “Will there be a need for sales person?” No. “Why?” Because marketing and product delivery are doing  such a great job. Really what we want marketing to do is to render the sales person’s job irrelevant.

Really what we want marketing to do is to render the sales person’s job irrelevant. Click To Tweet


Because they do such great job. What marketing department will do to make the sales person’s job easier, every salesperson dreams to be an order taker in as much as they want laid down. They want people who won’t raise any objections, they want people who will walk in and say, “I’ve got a board of cash. How could I spend it?” But until that happens, the salesperson will continue to be highly paid because they have a job which is to help people over those obstacles and to become a customer today instead of tomorrow. As long as that is true, sales will be a very valuable position for anybody, bots are not.

Yeah. I love that Tesla example that you gave. I know that they had the most successful online launch in history. I participated; I’ve put my $1,000 down.


Eventually I’ll build my Tesla.

Right. A few years ago, maybe two years ago, if you said to someone that you can sell a, I don’t know if they sell the previous models online but certainly you’ll be able to sell $35,000 to $50,000 to $60,000 cars online without any human intervention. Even three years ago people did said, “Yeah, right.”


Maybe your groceries on Amazon but people are never going to buy a car online. Actually, you’re already wrong.

Yeah, pretty amazing.

Yes, phenomenal.

Yeah. I do love the example you gave of you using bots in scanning the comments for the veterans to use the particular keyword that you asked them to use. That’s amazing. So many people are hence manually doing this where they’re saying, “Go ahead and type into the comments below I’m in and I’ll get you set up with blah blah blah” whatever. They say that in the video. People say I’m in and then they have to go in and manually say, “Okay. I just sent you a private message.”


A bot can do that for you.

Yeah, absolutely. Certainly the tool I use, maybe it’s called ManyChat.


I’m really just dipping my toe in it. I said, “Do you want to send a message to everybody? Do you want to send a message to nobody? Do you want to send a message only to people and include keywords?” I said only people and include keywords. Then you have to give specific instructions. But then you have to think what’s every permutation of this keyword is. What if people misspell it? What if people say yeah instead of yes, or yep instead of yeah. Then you’d go to your own test again to all of these possible permutations. No, I wasn’t interested in using a bot for them. I was going to have to do anything manually.


That for me defies the –

Defies the purpose, yeah.

It defies the purpose, yeah.

Yeah. ManyChat’s the tool that I use as well for Facebook bots. Cool. One thing that I just thought of that I wanted to follow up on, we were talking about sales people candidates and you screen for communication ability. One thing that popped in my mind is I recently started incorporating this into my job adverts. Not for sales people per se but just for any role like a virtual assistant. Have them leave a voicemail instead of replying to the job advert via email or sending an application. Because if they leave a voicemail, you can hear how they are on the phone, you can see how well they follow directions. Because if they didn’t even follow your directions in the job advert to leave a voicemail with the various details and instead they just sent you an email, they are already out.

Well, absolutely right. I couldn’t agree more, the ability to follow basic instructions. There is something about, I don’t think it’s true anymore maybe in some industries, traditionally sales people were seen as hard to control. Certainly when I was in Timeshare, it was understood that some people would not show for work for three weeks because they’re off on a bender. Then they’d show up at work the next day, they’d be given the stern talking to and put back to work. But it was forgiven because that was their character and they were so valuable to the organization. Then they’d just pitch rehab for a couple of weeks. Then they’d come back again or something similar. There has been this understanding that the really valuable sales people, the closes are worth keeping around any cost. I guess my duty as a sales trainer is to eliminate any organization’s dependence upon one tyrannical personality than the organization. If we can systematize it then you’re not reliant upon these rainmakers. Every organization has them. Obviously the small organization might be really dependent upon them. But if you can build up the necessary redundancy that you’re not dependent upon one maverick person who can get away with murder, then you’re a healthier organization for many reasons.

Yeah. Also that brings the whole culture down and the rapport is broken amongst all the team. If you have one person who can get away with murder that’s toxic to the entire company culture.

It’s usually around. One thing that I’ve seen a lot of companies do recently is set up entirely decentralized organizations. Whereby results only work environments has been talked about for a long time. But I’ve only really seen them implemented properly since this idea of virtual offices has become a reality over the last five or six years. Large technology firms were staff really only meet on Zoom or on whatever chat tool they’re using on a daily basis, but they don’t go into the office, where their job really, really is based entirely on the results. That’s great. But also for many naturally gifted sales people, self-motivation is very difficult as well. One of my clients here in Malta has recently implemented a stand-up meeting every day. Despite much resistance over many years, they finally said that it might be a good idea to do a stand-up meeting on a daily basis, 15 minutes quick book style thing before the day starts. That extra level of motivation accountability provided from a central structure has been incredibly beneficial to their results.

Why a stand-up meeting? I’m familiar with this but I’m curious.

The idea is that it’s a thing that happens daily and it’s a thing that doesn’t take more than 15 minutes. If you’re going to call your entire sales force, in their case it’s about 40 people, into a meeting on a daily basis to sit down and talk about things then that becomes a mood killer. Whereas if everybody is standing up, only understand but they don’t have time to go anywhere, they can listen to a little bit of motivation and get really daily accountability. Say, “Today I’m going to do this. Round of applause for whoever closes those deals. Yesterday we have set the most appointments. What are you going to do today? Who’s going to give us five new leads? Who’s going to give us 10 fantastic? You’re in competition against each other. Here’s some important industry update. Go get them.” That has been very, very old school and still really, really works incredibly well to help keep sales people motivated because self-motivation is a difficult thing.

Yeah. Do you have any other morning rituals or morning routine type stuff besides a stand-up meeting that would really help a person or a team get in the zone for closing lots of deals?

I think the morning meeting is the most important one. If you’re an organization whether it’s able to happen if you were centralized, if you were a common location I think that is the thing that really helps. It sets the mood for the day, it sets the main focus. When I ran the company, the coffee had been made before the morning meeting. You could come in whenever you want to. The morning meeting was at [9:00]AM. By 20 past 9 you you’re at your desks and you are working. That was fatigue; it gives the day a hard start. In terms of reporting and accounting and numbers, I think two things are useful. One, every sales person and all of their colleagues must be aware of their numbers. Stephan if we’re working together, I’d want to know that for every three meetings you made a sale and it took you 10 calls to get three meetings. I’d know this because the numbers were flashing up on the dashboard in the office. They were written on a whiteboard in the office or they were in the homepage of the internet of your office. I’d want any sales person to check any of the sales person numbers in real time. Because when you know your numbers, it helps you motivate yourself a little bit more. For example I used to get my guys to make 20 telephone calls or 20 qualified phone calls today when I ran a recruitment company. That meant in many cases they had to pick up the phone maybe eight times. That’d be 80 dials to get 20 qualified calls. A qualified call is something other than they’re not here, call back later. It would have to be getting some new information. They have to pick up five times. That can’t be a killer. Yeah, it really can day in, day out. It’s the date and time that said nobody likes cold calls but some people just have to do them. It could be a motivation killer unless we could assign a monetary value to every single telephone call. Every time you pick up the phone, that’s going to be worth $5 to you. How do we know that? Because you have to pick up the phone 80 times to talk to 20 people. You have to talk to 20 people to get two meetings. You have to get one meeting to make one sale. We say so if it takes 80 calls to make one sale, I need to say this is worth whatever 80 times 5 is $400. Then every single time you pick up the phone you just made $5, even if you haven’t spoken to anybody. Knowing your numbers is critical. Because if people are too focused on the bottom end of the pipeline which is where the money comes out, that’s the bit we cannot control. We cannot control the outcome, we can only control the activity that we import. If we say we know that we do 80 calls, those 80 calls are going to make us $400 then every call is worth $5.


Then what we do at the end of the month is say, “Great. How can we make every call worth $5.50?” That’s when we start to improve the form. Say you’ve got activity plus form equals the strong sales muscles. Form on its own is not good because you’re going to back it up with, I guess theoretical knowledge about selling is no good, on selling you must couple it with activity. Activity on its own is actually better than theoretical knowledge. But we want to combine the two so the activity is really highly effective. I’ve made every sales person aware of their number and everybody else’s. Then they’ll have a reason for doing the boring stuff, they’ll have a reason for going to the meetings, they’ll have a reason for picking up the phone and have a reason for making pictures that don’t make them anything today. The other thing it does is in gender’s competition, which is super healthy in numerable studies on this time. But nobody wants to be at the bottom of the leaderboard. If they do, you probably then want a new organization.

Yeah. It’s kind of like management by embarrassment.

I’d prefer management by motivation, or the other way around. Everybody wants to be at the top of the leaderboard, right?

Yeah. That’s very, very cool. Putting a monetary value to these various milestones is effective not just in sales but all aspects of marketing. You could say, “We have a long lead cycle for selling a big consulting deal. We can put a monetary value to the white paper downloads and say that’s worth x amount of dollars because whatever percentage of the time does white paper downloads turn into the big ticket consulting deals.”

Absolutely right. As you know marketing, if you don’t know your numbers, it’s a fairly fruitless endeavor or a blind endeavor if you don’t know your numbers and selling as well. Yeah, marketing if you want to know how much you’re buying your clicks for. Are you making money on them today or tomorrow or within 90 days or whatever’s acceptable to you? If so, great. Who is it said something about the ability to outspend the competition? You probably know that quote. You really want to be in a position where you can comfortably outspend your competition. Because the more valuable your clicks are, the more you can afford to spend that one which means you can beat the competition. When I’m doing webinars for example, I can be sometimes dispirited if I see that I have only 50 people on my webinar. But I know that I’m going to get $80 per show up based on historical data. As long as the source of the lead is roughly the same and the pitch doesn’t go dreadfully and I don’t have a cold and I’m on form, then it saved some of my concerns, alleviate some of my worries. I say, “Okay. There are only 50 people here but hey, I’m going to get paid based on historical data. It’s a reassuring thing.”

Yup, very true. Do you do webinars quite a lot?

I have one webinar. I do webinars for my community. I have a community called The Professional Persuasion Program which will probably change its name, it’s actually more for business owners than people who see themselves as salespeople. But we have life teaching webinars three times a month offering some element, Q&A. But I also sell one of my products, The School for Selling. I sell that on a webinar to joint venture partners at a slight discount from what you pay if you went straight to the sales page. I have something that’s been honed over time. I know that for every person who shows up, I’m going to get paid roughly $80. Half of that will go to the joint venture partner. My job is to get as many people to show up as possible.

Yep, got it. That’s pretty calm and model for doing this JV type of webinar. Does the joint venture partner show up on the webinar with you and introduce you? Are you doing a live webinar or are you using pre-recorded stuff? How does that work?

Today I’m doing it 100% live. Hence the joint venture partner doesn’t have to show up. I prefer if they do just for the transfer of credibility. Normally I learned in these JV webinars people who know me a little bit. We can talk and flirt and joke a bit in the beginning, which put people at ease. One thing that I will certainly do in the future is roll that out and have a green automated webinar. That I would not do for joint venture partners but I would do for cold traffic. I’d buy some leads. I expect that will convert roughly 50% as well. But the leads might be cheaper; I hope they’d be cheaper. If I have to pay $40 per attendee for a JV webinar, maybe I only have to pay $15 on a webinar that’s cold traffic. We’ll find out. I don’t know the answer to that yet. But certainly early next year I will roll the matter.

Yup. Do you have any criteria you use to select these JV partners in terms of their size or reach or anything like a half tail of a certain size email list, minimum or anything like that?

No, not at all. I do it for friends. One of the things that I’m quite good at Stephan is keeping in touch with people. I use the CRM system stuff.

And Contactually, yes.

Right. I mention it to people but I’ll never hard pitch it. Yeah. Now it’s got to this stage where people say, “Well, that was worth doing. I’d like to do it again.” Everyone’s busy with JV promos. I never want to be the phone in your side. I never want to be the one saying, “Hey, Stephan. What about that webinar? Hey, Stephan. What about that webinar? Hey, what about that webinar? Hey, when are you going to promote me? When are you going to promote virtually? Because that’s boring. I run away from people like that.” I don’t want to be that person. But I’m incredibly patient and I’m very good at keeping in touch with people. Eventually people will say, “Hey. I heard you did a great webinar with Bob. Do you want to try doing one with me?” I’ll say, “Sure. Just put it in the calendar.” I’d be dispirited when one person, he’d have 30 people show up but it doesn’t matter, it doesn’t affect the relationship. If I can’t spare an hour of my time for friends to try and make us both a bit of call then I can’t really call myself a good friend.

Got it. Cool. Back to this topic of morning rituals and that sort of thing, did you incorporate any kind of motivation or gratitude or anything into your own personal morning ritual?

I’ve usually been quite bad at that. I’m naturally more effective later in the day which means that my days have started very slowly. But actually most of my clients and correspondents being in North America and me being in Europe. I’ve, in the past, been able to afford to take mornings more slowly. However, now my seven year old and my four year old boys are both school age. I can no longer hide under the covers and pretend that the morning school run doesn’t have to happen. The day starts pretty early for me. The alarm is set for 6AM, [6:30]AM. Boys are loaded onto the bus and off by [7:30]AM. The dog gets walked either by my wife or I. My wife runs to work, I’d grab a coffee and start the day quite early. As long as there’s a shower and a coffee before I have to do anything, I’ll preferably have an hour stretch in the legs with the dog then I’m good to go. I wrote a self-help book years ago, which sold very well in the UK. The promise of that was I think you need to take responsibility for yourself and that you need to take yourself less seriously. I think you need to get better doing things. I focus more on the what than the how. I think that’s probably been my mantra for life: focus on the what. My life would probably be easier if I did gratitude generally or meditation or similar. But other than that, it’s a walk with the dog, coffee and don’t beat myself up about what time I start working.

You need to take responsibility for yourself and that you need to take yourself less seriously.

Okay. Yup. Are you a night owl type of person?

Yeah. It’s frustrating as well because I’ve always envied people who can be up in a cockle doo and having a coach hour, doing 20 laps in the pole and then writing 5000 words by the time I’m getting into the office. But it just never sat well with me. I’m going to be 40 soon. I figured why fight it? I know that I work quite efficiently, I can spend time with my kids, I don’t work every hour, and when possible, I’m home in time to take them into bed and read them a story, weekends I never work. I’m not going to try to be that morning person anymore because that was creating conflict that wasn’t useful, frankly.

Yeah. If you’re not wired that way, I mean we actually have our own chronotype, which for some it’s a wolf or a bear or a dolphin. For me I’m a wolf which is essentially a night owl. This is a chronotype as developed by Dr. Michael Breus. He wrote The Power of When.


Great episode by the way I have on my other podcast on Get Yourself Optimized about getting better sleep by discovering your chronotype, episode 58 listeners. Yeah, it’s so helpful to not work against your chronotype but instead schedule your life around your chronotype so that you’re working at your optimum.

Right. Are you familiar with Ronald Freedman?

No, I’m not.

Okay. Ronald Freedman did the Peak Performance Summit, a friend of mine. He’s got a PhD in this stuff: productivity and chronotypes and when you should be doing stuff without beating yourself up. Let’s see if I can find a URL for you, ignite80.com. He wrote a book called The Best Place to Work, psychologists to behave with change expert. Very good guide, and writes extensively on this kind of stuff as well.

Okay, cool. We’ll put that in the show notes as well with the other links that we talked about. Let’s leave our listeners with some place to go for working with you like on a one to one basis, on a one to many basis. Where would people go to work with you?

I think almost exclusively Stephan, the best place to go would be to matthewkimberley.com. I think I own every permutation of that spelling. But it’s two t’s, ley, .com at the end. Sign up for the emails. On the home page there are two or three places where you can enter your email address. All you get then is a copy of my guide which is called Five Things You Need To Do Every Morning To Get More Clients In The Next 60 days. It’s an explanation of my keep in touch rituals, it’s how I use Contactually and how I manage my relationships. But the challenge in it to do it for yourself, then you get an email from me sporadically. One of your first emails will say, “Hey. Write back and introduce yourself.” That’s typically how good relationship starts. Yeah, matthewkimberley.com.

Awesome. It’s not a bot that’s going to respond to that?

Well, it’ll be a bot that sends the first email that says, “Hey, congratulations.” But after that when you hit reply, I’ll read it.

That’s pretty cool. Alright, awesome. Thank you, Matthew. This was a lot of fun. I think it’s going to really help people with their businesses. I encourage my listeners to reach out to you and work with you because you are an awesome dude. Thank you. Thank you, listeners. We’ll catch you in the next episode of Marketing Speak. This is Stephan Spencer signing off.

Important Links:

Your Checklist of Actions to Take

☑ Pay close attention to detail when I am doing my sales strategy. Make sure to leave no stone left unturned.

☑ Be systematic and meticulously follow guidelines. Sales is not all about ad-libs and improvisations.

☑ Adapt my sales strategy depending on my organization. There are specific ways to approach prospects based on what I’m selling.

☑ Create a sales checklist and make sure I mark everything off and follow a strict process.

☑ Position myself as an authority in the field to gain more respect from my prospects. For example, VP of Sales is a better job description than Sales Consultant.

☑ Use my learning experiences to adjust my sales process by evaluating what works and what doesn’t.

☑ Continuously work on my communication skills. I should be able to hold conversations, avoid using filler words, and speak with empathy.

☑ Keep an updated CRM to access all my data in one place. Recommended tools include Infusionsoft, Capsule, Help Scout and Pipedrive.

☑ Use technology to my advantage. Utilize bots and artificial intelligence to eliminate human work and help me focus on my warm leads.

☑ Keep in touch with the people I’ve closed deals with. Make sure they know I am available if they need anything.

About Matthew Kimberley

Matthew Kimberley is a sales trainer and keynote speaker. Hes the former Head of the Book Yourself Solid® School of Coach Training, the founder of The School for Selling and the Single Malt Mastermind and the creator of the Principles of Professional Persuasion. His first book is How To Get A Grip (John Blake, 2011) sold over 50,000 copies.

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