Working Better Now with Steve Bookbinder, CEO of Digital Media Training

by Andrew Cohen
Published January 31, 2021

WBN Chairman, Rob Levin, speaks with Steve Bookbinder, CEO of Digital Media Training, on how Steve and his team are Working Better Now. Steve shares insights on:

  • The DM Training Team
  • What businesses can do to improve their selling now
  • Why more leads isn’t the answer to better sales
  • How DM Training uses technology to scale and better serve clients
  • How WBN virtual assistants are part of the secret sauce that has helped DM Training grow 
  • A critical question to ask in the final stage of selling
  • Unique opportunities that many companies have during COVID

Here are clips from the discussion. The last video is the discussion in its entirety.

A complete transcript is posted below the videos.

Steve shares why more leads isn’t the answer to better sales:

How DM Training uses technology to scale and better serve clients:

Steve discusses how DM Training is using their virtual assistant:

The entire Working Better Now discussion between Steve and Rob:

Complete Transcript of the Interview

Transcription of video discussion. Please note that edits have been made for readability.

Rob: Okay. Hi and welcome. I’m Rob Levin, chairman and co-founder of Work Better Now. And on behalf of the Work Better Now team I’d like to welcome everybody to our series, Working Better Now, where we do a Q&A with the successful entrepreneur. Today we are very fortunate to have long-time contact. We’ll go into that in a second, Steve long-time contact, Steve Bookbinder, CEO of DM Training. Steve, welcome. Thanks so much for doing this. And let me just start out. We met, I believe we met when you were at a company called DEI. So I guess that’s a good transition to … Why don’t you just tell us about your career and how you got to DM Training?

Steve: Okay, sure. Well, I took a very circuitous route to the point that I’m at now, which is to be the CEO of a global sales training company. Before this I was with another training company called DEI and worked with companies. We did sales training, across many industry verticals and geographic verticals, who’s all over the place, working with companies in every business. But before that I was in advertising. So I always had a love of advertising and was trying to then bring sales training to advertising. And in that process eventually started bumping into digital media businesses. This was late 90s, early 2000, fell in love with the space and realize that’s where the future was, and needed to jump with two feet into that space. Left training, went to work at a company called 24/7 Real Media, eventually bought by WPP. I’m now working at the Group M. Eventually I leave Group M, and eventually the chair of the IAB, Dave Moore, who was also a good friend and a guy that I swam the English channel with in 2008, he asked me in 2009 to launch this company, originally with the goal of bringing the best and the brightest into this very fast growing industry, anybody that wants to be relevant and have a great job, it’s going to be around, go into digital media. And eventually we morphed. We evolved from only training media sales people to training media sales people more about digital media, but teaching non-media sales people things that they now need to know about digital selling. If you’re selling and you’re doing it by virtual meetings and email, and social selling, you’re digital selling and the customer is living in a digital world. So that’s how I got there. And just before I got there, we’re going to advertising. I was doing advertising during the day, I was doing standup comedy at night. So the thing was, how can I get the creativity that I like out of the advertising, the getting on stage that I remember from stand-up comedy, but only during the day, not on holidays and how do I get paid the commission? And that’s what led me to even discover there’s such a thing called sales training. And that’s how I got into that business. So that’s the whole story.

Rob: Gotcha. Gotcha. Again, I think we met while you were at DEI. Although I remember when you went over to 24/7 working with Dave Moore, did you work with Jonathan Sue as well?

Steve: Yep.

Rob: Perfect, great exit that they had. He can take all the credit. So, if you look at the work you’ve done in the past, particularly with smaller businesses, let’s say $20 million in revenue and under, right? What’s the, you walk into it back in the old days when you used to go into a client’s office, walk into a client’s office, you probably know within five minutes what they need, what they can be improving on, what they could be doing better. What is that typically? Let’s go pre-COVID. Pre-COVID, what was the opportunity or maybe still the opportunity today for most small businesses to improve how they sell?

Steve: Most companies do not think about pipeline management. It’s just not a thing they think about it. They don’t think about it in the way I think about it. So what they end up doing instead is they think about let’s hire people who already know how to sell. Maybe they even have a … And smaller companies will often go that route. Either they can’t afford anybody with any kind of skills at all, or they hire somebody where they so-called Rolodex. My father used to be in business and he has an old … I have an old fashioned Rolodex like the museum of sales in my office, an actual Rolodex. And that’s what you’d have. You’d have people that knew people, and that would be the key to making sales. And what companies go through is there’s a ripple effect. Watch how the ripple effect works. The first part of the ripple effect is the salesperson believes they already know how to sell and nothing, nobody’s going to teach them anything. Because their sale is different and no other sale skills would apply because nothing on the planet is like what they do. How do they know? They really don’t know. They only believe that to be the case. But if you look at their resume, they’ve always worked in the same business. I’ve just told you I was in stand-up comedy and advertising sales training with a million different companies. I’ve literally done more than 5,000 workshops. I’ve literally trained more than 50,000 salespeople and sales managers and owners. And when somebody says to me, “Well, we’re different.” I go, “Well, I’m actually a better judge of that.” And you know what? What I’ve learned is a lot of things that you think are different, somebody in some other part in the world in a different industry has the same challenge and maybe came up with a different strategy. So my thing is going around the world, working, and I kind of get a backstage pass if you will. I work with clients generally with their pipeline. So to do that the client has to share with me what their pipelines look like, the forecast look like, including their inaccurate forecasts, the KPIs, including the KPIs which are either dubious or not helpful, or the missing KPIs of things that you should have, but you’re not tracking for some reason. But it starts with the salesperson not wanting to follow a manufacturing process. Here’s the manufacturing process. You start with a goal of what you want the output to be. You come up with a process that produces that. You figure out the inputs that give you over time the outputs. Totally different in sales. In sales we start off with the inputs, with no idea and no connection between what all that inputting is going to be on the output. Not only how much it’s going to close but when it’s going to close. Meanwhile the owner needs to know when it’s going to close. The whole thing is, so the sales process is mysterious and it’s totally opaque. So pipeline management isn’t just simply organize things into a pipeline. It’s, don’t make sales opaque, make it open, make it a community activity, make it so that everybody shares the same language when we use terms that everybody uses like qualified. What does that mean, qualified? I’ve literally asked 15,000 people. What does that mean? Because it’s the first thing you do, right? Qualify. Okay, what does that … When you find somebody’s qualified, what thing is true of them? And here’s what you learn. Well, they could potentially have a need and they could potentially pay for it. Well, guess what, everybody has a potential need potentially.

Rob: You mean, wait, Steve, you mean she took my call, that doesn’t mean that she’s qualified?

Steve: She’s qualified. What I learned is a big part of qualified, which I only discovered after I went into business for myself is, could potentially have a need, could potentially buy and can make a financial budget decision in the next 60 days. That piece becomes actually more important than the other pieces. But 50%, what does 50% mean? How much of sales is a forecast and how many times does salespeople use 50%? Well, if I give you a proposal, either go yes or no. If I call a lead they either meet or they don’t meet, everything is 50%. I go, “Really?” Because watch, your lottery ticket’s either a winner or a loser. Is a lottery ticket 50%? No. If it were every other time you bought, you would win. Well, you apply that to sales what you get is salespeople only prospect as much as they think they have to.

Steve: They think everything that they’re working on is a 50% chance of closing. They stop prospecting early on. Then when they get pressure, they go back to those few people they started prospecting to, and nobody knows what the what’s going on. And they pressure those people, literally dropping their pants, begging for the sale. So they finally close the wrong sale, the wrong deal, not enough, miss the goal. So pipeline management changes that. It says, “How do we create a lead flow and deal flow, which will produce the right number of sales all the time? And where were the sales before the sales?” They’re in the pipeline? So here’s a question I like to ask people. Look at your pipeline. What is your pipeline supposed to look like? Here’s a question I never even thought about. Well, that’s what I talk about with pipeline management. How do you change your goals into a pipeline? How do you make your goals from a dream into action steps? How do you know you’re on progress to get to your goals? You got to inspect, you taught me what is measured is managed. Well, let’s manage the growth. How else are you going to manage if you don’t do it that way? And let’s have everybody on the team speak the same language as each other. And over time what happens is everybody’s happier and they make more money. And the owners know when the money is coming in.

Rob: Perfect. Thanks for that, Steve and I couldn’t agree anymore. In fact, I’ve taken tips from you over the years, went back when I had the New York Enterprise Report and managed Salesforce among others. And it’s, you can really apply a methodology to it. And if you’re not you’re out of your mind. So, that was pre 2020. 2020 of course added just a few extra wrinkles to selling. So in a nutshell, what additional opportunities do companies have now that we’re going through COVID? Where can companies improve in general?

Steve: And there’s a bunch of things all coming together all at once. I think a bunch of things that were happening anyway accelerated because of COVID. Just like 9/11 accelerated things that were already happening. Well, in this case, here’s what, where we are. We’re in a world of quantity and quality. You cannot solve sales problems with quantity anymore. However, you’ve got a lot of quantity tools. So you’ve got marketing platforms and you’ve got CRMs and things of that nature. So with salespeople I see is happening is this. They’re at home, they’re under pressure, and it’s hard. Many people don’t have a home really designed to be a work environment too. So they’re trying to work with the washing machine behind them and the kids running around and all the other distractions, it’s hard. They don’t know how to organize themselves, their time, in that environment. And I’ll give you an example of something. In an office from nine to five, you take a couple of breaks. If you took more than a couple of breaks people would talk, “Hey, come this guys. I was on a break.” When you’re at home, you’re at work pretty much by the time you open your eyes. You open your eyes you’re already at work. You glance at the computer and your email just before you go to sleep. So your workday maybe is 18 hours. So given that you got to take breaks, you got to take real breaks. You got to organize yourself. You have to say to yourself, “If I don’t organize my day right, I will get tired. I will get frustrated. I will get bored.” So you need to create bench … You’re going to be your own coach and your own cheerleader. You got to create benchmarks that’ll keep. You can get a street going that you can keep yourself motivated. You need to have other kinds of KPIs that you could measure progress. So it’s not about the quantity of how many emails are sent or even the number of hours you were working in a row. It’s the quality of did you get one person to meet with you better than if you send out 50,000 emails? And I mention this because when people get frustrated they go, “Quantity. I just always want to feel like more, is more likely, throw a lot of stuff against the wall. I know it sounds stupid, but I can’t help but throw a lot of stuff against the wall. And I’m not comfortable unless there’s a lot of stuff on the wall.” And so I think people are just driven by the wrong behavior. They end up getting frustrated. They don’t set up their time right. And then watch on the quantity thing. We have now gotten to the point that you could very easily send a lot of emails. If the goal is to send a lot of emails, well, you could automate. Here’s what people can do easily, and they need to do. They need to take their big mailing list and break it in and think like a marketer, break it into a bunch of smaller lists by personas with now you got to think like a real marketer. You got to think about a cadence strategy, AB and ABC tests of templates. You need to be tracking what is the frequency cap on the number of times you need to send somebody an email before it becomes ineffective. You also need, most salespeople they kind of get it, but they don’t. Here’s what they do. Well, this is what 99% of them do. They write an email like Shakespeare. They go, what would get this person who I’m sending this email to, to be so excited they’re going to buy it for me? And so they load up the email with every sales benefit you could possibly come. Then they’re out there. They’ve exhausted themselves. Second email they have nothing else to say. So they say, “Did you see my first email.” Third email, now they’re frustrated. “Hey, a simple reply would have been nice, you know?” Now they’re shaming you into it. Why did you think you were never… You’re only going to send one email in the first place? So this notion of a communication cadence, personalized email. You know the problem with that? It’s hard work. You know what’s a lot easier? Just send out more emails. So that’s what I see. I see the biggest problem in today’s world is not an over-reliance on technology. It’s not knowing how to properly use the technology. The purpose of these marketing platforms that everybody believes in is not just to send out a lot of stuff. It’s to improve your conversion rate. Ah, improve my conversion rate? Yeah. You don’t get paid if you send out a lot of stuff, you only get if there’s a conversion. And so what just on thinking outcome first, and then building every part of your process to how do I achieve that outcome? Look, for example, no sales person miss the news they should prepare for a meeting. Nobody miss that news. But when I ask people, “What is the purpose of prepare? How do you measure successful preparation?” This is where they go, “Oh,” and you could always tell salespeople when they’re making it up as they go along, because they do it the way cartoon characters run, which is like this. First the cartoon character is not running. Then it starts to run, but it doesn’t go anywhere. Then a lot of smoke occurs around the legs. And then with a funny sound effect, it’s gone. And the same thing with, but how do you measure the product? I don’t know. Here’s how you measure. Did you get a scheduled next step at the end of your meeting? If you really prepared right, then you know what would have happened. You would have had to schedule the next day. If you’re not actually tracking that, then you can’t track if you’re preparing the right things in the first place. So, I guess to answer your question, you know what I see, the devil in the detail. There’s marketing, but there’s not personal marketing involving social selling email correctly. There’s doing marketing things, but there’s not thinking like a marketer. There’s preparing for a sale, but not preparing for it the way like the military would prepare with targets and benchmarks and training and steps and even questions, like nobody miss the news you should ask the question, two ears, one mouth questions. And yet people cannot think of … People think of first-level questions. I do a whole program at second level questions. What questions should you ask that you didn’t ask? I’ll give you an example of this one. This comes up in practically at every sale, because so many sales now involve multiple influencers and other people, even if they’re customers that, “I’m the decision maker.” By the time you get to the proposal, all of a sudden there’s another person. At some point the customer says to the salesperson, “I’ve got to talk to the team or my boss or the committee or somebody else.” Typical sales person says, “Can I come with you?” That’s the question. Here’s a better question. When you talk to the team, when you talk to the boss, when you talk to the committee, will you be recommending us? Wouldn’t it be a better question? Because now the answer would be, “I am.” “Oh, great. Because then I don’t need to be there,” versus, “Well, I don’t want to influence the others unfair. I’m not going to really recommend, but I got to hear that.” [crosstalk 00:17:18] So what’s going to happen in the rooms when I’m not in the room? I just wrote this book, Echo Selling. It’s all about that. It’s how do you get your sales pitch to echo into places that you can’t get into? So that’s what I really see. It’s not like this new skills other than the devil in the details. Although echo selling is a new skill because buyers have absolutely measurably changed.

Rob: Yeah.

Steve: They meet with a sales person later in the process. They hardly meet with them at all. We’ve got to create a way to get our sales pitch to echo among people that were in meetings every week when we’re not in the room with them.

Rob: Yeah, I haven’t thought about that. It’s about changing, the sales person can help change the point of view of the person they’re talking to if they’re on their way of doing that. But that’s a discussion for another time. Let’s talk a little bit more about DM Training. So I think you have a pretty lean team. I also know you rely on technology a lot. Tell us about the team and how you’re able to serve all of the clients that you do?

Steve: I have a lean team. I’ve also got a very big team. Watch how I make my team very big. A few years ago I had a team that was a small team relative to companies. I had maybe 15 people. And of those 15 people approximately 10 of them were salespeople. And everybody else had some other job. One of the things I’ve learned is to work instead through partnerships. So one of the partnerships that I work with are trade organizations, a lot of media trade organizations and non-media trade organizations. When I work with a trade organization, I’m helping the trade organization contact who represented the trade organization, helping that organization make more money and provide more value. When they see my relationship, the relationship with me is helping them make more value to their members, they realize it’ll help them hold onto the members, get more membership fees, get more money, actually make money with our training. So what happens? They sell their members for me. I have three different organizations I’m working with currently right now, one in London, one in Italy and one in the United States, giant organizations that are marketing to their people. And the salesperson? I’m not paying them a salary. They are also a small business owner, or they’re the head of this association. And so I have tried to find ways to work through partnerships and that’s how I’ve expanded my team. I find people want to work this hard because they own their own company, rather than a payroll employee. So I have a minimal payroll employees, maximum partnerships, and that part works great.

Rob: Gotcha. How long did it take you to figure that out?

Steve: Well, we had a really bad year in 2016 and it was then. The company started falling apart and I realized that I really don’t have any other job I could do other than this. I have to find a way to reinvent the same company. So what do I really need? I really need people who can help me produce videos and make online training and make the webinars more interesting. And if they need more production things, or I needed people. My feeling is find people that already have a relationship with the people you want to know. So I mean, I guess like a prospect everybody, but somebody who’s already got that relationship. Why can’t I work through them?

Rob: Gotcha. Gotcha. So tell us a little bit about the technology that you use, whether it’s to run the company and or to deliver your training.

Steve: A couple of different technologies. So one from the client perspective looking at us, the biggest technology that they see is a learning management system, which is our online platform. One of the things we’ve learned about online, we tried to make our own, we’ve spend millions of dollars doing that. We’ve eventually licensed a very great LMS and it’s … So that LMS will generally like the human brain have way more capabilities than anybody is using them for. So you could grow within that. I have all these interesting business models. I have other trainers that have a need for online training, would like to have on online training, but don’t have any assets. So I actually rent space on my LMS for other trainers. Two women trainers that I’m working with just won some award for their online training, which in fact is hosted by my platform. So I feel like a part of their reward. But that’s a main one, but here’s what I’ve learned. And it’s a lesson that you see throughout digital media. Every obstacle will block users. So here’s an obstacle, you have content on one page of a website. You want users to go from this page to this other page of the same website. Generally speaking you’ll lose half of the audience. That’s going from one page to another page of the same website, you lose your audience. If you’re on LinkedIn and you want people to go from LinkedIn to a website, you’re going to lose them because some people just want to stay in LinkedIn or just in Facebook. They don’t want to leave that environment. So every time you leave the environment it’s a problem. One of the ways we’ve solved the problem is we look at the training business from the sales person’s point of view. There’s a million little pieces of paper and Post-it notes and all kinds of files hidden all over. Where is that training that I’m supposed to find? So we’ve created a landing page where all the training can always be found. So there’s one landing page. We just keep updating it. So let’s say I’m working with your company all year long and every week or two we had another training video, the people could just click to the next asset. They go one page. They don’t have to go into my app and use a login and get there. So I’ve just simplified the technology and we also will make good use of Google Docs. When we have to share stuff, we’ll use that, make it easier. Internally we use Dropbox a lot. We use HubSpot as well for our work.

Rob: Gotcha. And Steve, you hired one of our, well actually you went through, you had two of our VAs this year. Tell us a little bit about your experience in how WBN VAs have helped you, what they’ve done for you and what that’s been like?

Steve: Okay. First of all, it ended up what I’m using your virtual assistants for now is very different then what I originally envisioned. You had told me that that would happen, and yet I could not have visualized it. So initially I had my right arm person went on a maternity leave, could not function without somebody taking up some of that slack. And so thank God, Work Better Now is there to get me a virtual assistant. But what I learned was, first of all, we’re in a pandemic. Nobody can be in the same room with anybody anyway, but what’s interesting is if you’re working on a creative project, which for me means a document, an infographic, PowerPoint, physically how can you work with a second person unless you’re both in a remote location looking at a shared screen? In other words, if you were literally in the same room with me, unless we position the monitor, you’d have to like sit on my lap for us to look at it together. So chances are going to be in a separate room looking at a shared document. Since that’s the case anyway, what difference does it make where the person is? So what I ended up doing is working with a person in El Salvador who is able to look at the same document. We sit there together and looking at something and go, “What about this? Can you make that? Good.” Well, what I did not anticipate was every time the need was, can we operate this other software? Is there another app that does the thing we need? That the VA could A find it, find that there is in fact another app, and B find out how to work it. Read the instructions, watch the YouTube video, or call somebody else that’s another virtual assistant. And between all those things we were able to solve a whole bunch of technical problems. We’ve even solved it this way. I would have a technical problem on my end, could not solve it. The whole show was stopping because I could not figure something out. Put the virtual assistant on the screen with me. “How do I change the thing and make this thing work?” And she looks at it, she goes, “We just do this, that, and the other thing, and it’s done.” [inaudible 00:26:16], I had no place to go, needed help in this moment. I don’t have an EV department, IT department down the hall. And so there’s that person. Well, I thought the original need was for calendar management because we have a lot of calendar management issues, a lot of production and schedules and overlapping and so on. What I now have VAs doing is producing videos, helping me with marketing, helping me proofread my notes. In fact, one of the things, and this may sound stupid, but I like working with other people. I just like being in a group. I swim in a relay, I like … So there are certain tasks that we do that we just do it together. And there are certain tasks we do that the virtual assistant is doing something while I’m doing the other part of the same project. What’s great is I will shoot a video against the green screen. They will take that and produce a whole video with openings and closes and backgrounds and editing and all kinds of stuff. So what happened? I just did the part that I’m good at. She did a bunch of things that she wasn’t even necessarily good at six months ago, but she’s great at now.

Rob: Very cool. That’s awesome to hear. So Steve, when you’re not working and you’re not making videos and you’re not helping companies and all that, whenever that is-

Steve: Exactly.

Rob: Hopefully you have more time now, now that you have one of our VAs helping you, what do you do in your free time? What do you like to do in your free time?

Steve: I read. Well, I mean, I walk when I can, I’ll be swimming more if my pool was open, but I read a lot. And we’re in a world where we have to mostly, especially salespeople, have to write stuff. And what makes you a better writer? Reading. It’s impossible to read anything without learning something. And it’s also impossible to read without getting better as a writer. So I enjoy novels. And so I alternate between a business book and a novel, and people said, “You read sales books?” I do. But my sales book is on psychology or it’s on game theory or it’s on the wide range of books which I now think of as sales books.

Rob: Right.

Steve: So reading, big thing.

Rob: Gotcha. And Steve, finally, where can people find out more about you and DM Training?

Steve: Well, you could find me on LinkedIn. You could also go to www.dmtraining.net, and you’ll see our courses. We have a lot of free stuff, including playbooks and newsletters and podcasts. We also have announcements about webinar series and things of that nature. And every so often we run specials, coaching specials. We’re running a kickoff special right now. So you find all that on our website.

Rob: Fantastic. Steve, it’s always a pleasure. Thanks a lot for taking part in the Working Better Now series. I’ll be speaking with you soon.

Steve: Great. Thank you so much for involving me. Take care, everybody.

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