EPISODE 579: Connecting with Hard to Reach Prospects with Chris Tuff

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[EDITOR’S NOTE: This podcast featured an interview with Chris Tuff, the author of Save Your Asks.]

Find Chris on LinkedIn.

CHRIS’ TIP: “Send video text messages. As you’re talking to prospects, send video text messages as much as possible and put into application. I speak at a lot of events, and I meet executives. The way that I’m able to take it to the next level so quickly is I do it with video text messages.”


Fred Diamond: Chris, I’m excited to have you here. Your book, Save Your Asks, A-S-K-S, what number of book is this? Is this your second or more than that?

Chris Tuff: Yeah, this is my second one. Yep, that’s right.

Fred Diamond: Good for you. It’s a great book and we’re talking today about authentic connectivity, authentic conversations, authentic relationships, and you’re that guy. When you wrote this book, you interviewed some of the world’s greatest leaders, and some of the greatest entrepreneurs as well. It’s basically designed to help salespeople and businesspeople get better through the art of courtship. What exactly does courtship mean in this context?

Chris Tuff: One of the things that I learned in all these interviews is actually this idea that creating relationships is really easy. It’s sustaining them that’s difficult. One of the things I set out to do is, I looked at me being on the receiving end of a lot of asks, as you are, right? As a lot of listeners are. There are askholes all over the place.

If you look at our LinkedIn, people are going in for the ask way too early. One of the pieces that I really wanted to focus this in on is that if we just went into relationships with the desired outcome instead of it being reciprocity, which is networking, and instead just being authentic, genuine connection, then we’d all be not only more successful in what we did as a salesperson and a networker, but also it would be a lot more fulfilling. That was really what I was going after in all of this. My best demonstration of courtship actually is one of my favorite tactics. That is this verb that I was introduced to in 2012 called Shawshanking. Now Fred, do you know Shawshanking? Have you heard of this term before?

Fred Diamond: Here’s what I call Shawshanking. When you’re sitting on your couch watching TV, and you’re flipping through the channels and Shawshank Redemption comes on, and you have to watch it for the next two hours. I coined that aspect. Same thing happens with A Few Good Men and Meet the Parents. Tell us your definition of Shawshanking.

Chris Tuff: [Laughs] Shawshanking was introduced to me 2012. I was at a steak dinner to celebrate my team and a friend, fellow entrepreneur. I just signed the largest deal of both of our lives. I was the buyer, he was the seller on it. I turned to him at this dinner, his name’s Jason Beckerman. I said, “Jason, here we are signing the biggest deal of both of our lives, and I know I’m not an easy person to pin down. You and I met in 2007 in a closed Facebook group and now here we are five or six years later signing this.”

The sales guy in me, I’m Head of Sales for my company that I’m a partner in, “How did you do it?” He goes, “Chris, you really want to know?” I was like, “Yeah.” He goes, “I Shawshanked you.” I was like, “Shawshank? What is that?” He goes, “If you remember in Shawshank Redemption, Andy Dufresne, when he got sent to Shawshank Prison, he had to write a letter a week to get the library funded.”

He never heard back, was a letter a week and it was two years later, he got his first check for $200, but he didn’t stop there. He kept going and it was 10 years later when he escaped Shawshank Prison. They had the nicest library in the whole prison system. He goes, “Chris, every single week since we met in that closed Facebook group, I’ve had some sort of touch point with you. Not once have I gotten in for an ask, but I’ve sent you a message on Facebook Messenger, I’ve sent you text messages, emails and now here we are.”

I was like, “Oh my gosh, Jason.” I just got a call from a CMO of a Fortune 50 company, it was actually on LinkedIn, and she wanted to hire me as their digital and social person. I was super obnoxious in my reply. I was like, “Yeah, I’d love to work with you as your agency partner.” I’m like, I’m going to go try this same approach to them.

I got a hold of the CMO’s cellphone, I called her on her cellphone, and I said, “Listen, let me just come down there to your headquarters and help you.” Because so many people are full of it as it relates to digital social media, I can give you a few candidates, and I can just try to help in whatever way I can. Creating value, creating the touch point, and starting that Shawshanking process, that courtship.

I went down there, I met with them and our head of marketing for about an hour and a half and it was about three weeks later they say, “Chris, will you come do a merchant learning session for our thousand merchants?” I was like, “Absolutely.” Then it was six months later, like, “Hey, Chris, will you help us with this thing?” Not once did I ask for a contract or a project. It was 14 months later, we got our first project for a pretty large activation and today there’s 120 people on that one account.

Shawshanking, it’s this idea of not only writing the letter a week, it’s this chipping away piece. One of the exercises I do in my keynotes is I have everyone in the audience take out their cell phone. It’s about 20 minutes into my speech, as I’m talking about these concepts, I say, “Think about the first person that comes to mind who you haven’t had a touch point with in the last six months. I want you to send a text message right now as you’re sitting there saying, “Dear so and so, I just wanted to say what’s up, it’s been a while. I hope you’re having a killer day.”

Everyone takes out their phone and they do it. I revisit that at the end of my speech, it’s 13 minutes later. I say, “Raise of hands, how many people heard back from that person that you texted?” You’d lost touch with them. You probably would have never rekindled that relationship, and it’s always 25% of the audience raised their hand. Now you go, how amazing is that? Because for the first time ever, you went out with the only intention being connection and lifting someone up instead of it being more of this askhole approach.

I’ll say, “Millions of dollars of business will be created in this room off of that one text because you’ve rekindled a relationship that otherwise would have gone dormant. The second piece is for those that have your hands down, it might be a sign that you’re an askhole, and so that’s why they’re not responding back to you.” To me, that’s what the courtship thing is. Being a little bit more longer-term in our thinking and sustaining that, and then finding that right moment when the ask is right.

Fred Diamond: One thing we talk a lot about with sales professionals on the Sales Game Changers podcast, when I talk to leaders, and a lot of times on this particular show I interview VPs of sales who’ve been successful for 20, 30 years. You just don’t wake up one day and say, “You know what? I’m done flipping burgers. I want to be a VP of sales at Microsoft or Hilton or something like that.”

You’ve had to be in the game, but you have to have been passionate, and you had to be motivated to serve at the end of the day. If you’re just like you say, an askhole, then eventually it’s going to dry up because people aren’t really going to see the value. What if you’re a sales professional and you’re struggling right now with understanding what you’re truly passionate about and you notice that that is being an inhibitor towards your sales success? What would be some of your thoughts on how to get past that? Or if you’re a sales manager, sales leader, and you notice that some people on your team, they’re just not as passionate about what I am as the sales leader to help our customers achieve our goals.

Chris Tuff: That is a great question. My response to that would be this, and it comes down to one of my favorite quotes and whatever you call all this stuff that I’m doing now and it’s, curiosity is the backbone of connection. We’re not salespeople, we’re connectors. If we take this mentality that our job is to create connection first and then out of that everything else will flow. What I mean by that is you could be selling the lamest thing in the world. It could be the dongle for my computer or nuts and bolts. That does not matter because the name of the game in this curiosity piece is you take a genuine interest in understanding that person as a human first outside of their business. I call it a race to the medal and a race to the medal is the exercise of finding that common passion point between you and that person.

I call it the Google me exercise where if you are a Google search engine, what are all of those passions that people go to you for advice around? So, for me, it’s like Big Green Egg grilling recipes. For you, it’s a lot of the things you have authority on, but also the nuanced ones. It’s the whole platform around Lyme disease and what you’ve gone through. It’s the sales piece, but it’s also the nuanced pieces. For me, how to learn how to kiteboard.

People go to me for advice there. Cool places to travel to in the Caribbean, being the father of young daughters, they’re all of these things that we can exercise in creating that genuine connection, and then getting to a place of that curiosity to then expand upon it to understand those humans. I also tell people, I’ll watch SportsCenter every Sunday. I don’t even really like sports or football, but it gives me another piece of my ammunition, as I work my way towards a place where that person that I’m selling to, or if they’re on my team and I’m trying to motivate them, it’s the same thing.

We got to create that genuine connection with them and then asking the questions. That’s where the magic happens because then you start, “So tell me more about what you’ve gone through with this whole Lyme disease thing, tell me more about what it is that you’re out to do”. Then you graduate to this place. This is where I get super fired up, where I ask someone, “So what’s your dream?” What fires you up more than anything else in the world?” That’s where the bond and connection is created that’s sustained for life.

As salespeople, we’ve all been trained to treat work like work and business like business, and you don’t go in that other way. I do the exact opposite. I go into the personal piece, I get to know them. Now we start talking about their business. We talk about some of their struggles, and then you come in and say, “Well, guess what? I’ve got this dongle that we just created and that thing that you were telling me about, it’s going to address all those things.” It’s like, there’s not even an ask at that point. You’re not even a salesperson. It’s like you’re doing them a favor because you have enough data. Look at the process that we all go through, which is, “Hey, can I get 15 minutes of your time to sell you my stuff?” It’s backwards.

Fred Diamond: One of the best bits of advice that we ever got on the Sales Game Changers podcast was by a sales VP, his name is Gary Milwit. He works for JG Wentworth, the company that buys and sells settlements. He said, “Make who you’re talking to feel like they’re the most important person on the planet.” It goes back to a lot of things in that people like to talk about themselves, and they like to be asked questions like, what drives you? When you’re out there on a sales call, I love to ask the question like, why do you do this? Why are you so passionate about serving this? In a lot of the past episodes of the Sales Game Changers podcast, we’ve interviewed people who’ve been selling to the government for 30 years.

I’ll say to them, “Why have you devoted your life, your career towards selling software to the Department of Defense?” It’s always the same answer. It’s because of the mission. “I believe in the mission. My father was in the military, and I believe in how do we protect us, how do we protect our liberties, our freedoms, whatever it might be.” Same thing with people who sell into health care. Same thing with people who sell whatever the solutions might be, it goes back to things that they are completely passionate about.

I want to ask you about the mindset of young professionals right now. One of your previous books, The Millennial Whisperer. One thing we talk a lot about on the podcast is what drives younger people to be successful right now. It’s different than what’s driven a lot of people who are in their 50s and 60s, who have had a certain type of success in sales. Give us some insights for the sales leaders listening to today’s podcast on what drives the younger people in their organization from your experience. What do they want? What are they looking for?

Chris Tuff: There’s a couple things that are happening here. My Millennial Whisperers to Gen Z Whisperers, basically anyone 40 and under are millennials. If you can’t get older millennials right, you’re certainly not going to get Gen Zers right. There’s a couple tension points that are happening right now. One is that the younger you get in the millennial set, so really 35 to the 24, there’s more of an expectation that their passions will be etched when they get to your organization.

They graduate, they come in, and when those passions are not etched, when they’re not actually flexing some of these things that fire them up, they end up leaving. There’s more of that expectation. So, what are we doing within our organizations to take on that role, not just as a boss, but as a mentor and a coach to help people in our organizations pursue those things? That’s one piece.

The other thing, especially in sales, there’s nothing as dynamic as meeting face to face. There is a massive void in that interpersonal muscle, especially in the younger millennials and Gen Zers because of technology. Think about the first time any one of us – and I’m on the cusp of millennial and Xer, I’m 42. But you look at just to flirt with someone. We had to pick up the telephone and write and dial or whatever. We had to get through mom and dad and then we would talk to that person. I would always create a list because I was so nervous. Then I talked to that person for an hour, and then I’d move on to the next because there was none of this. You juxtapose that. That interpersonal muscle was built in us because we didn’t have technology.

Younger millennials and anyone 35 and under, at age 13, they’re given a brand-new iPhone with a Snapchat and Instagram and everything else, and so they’re a lot more comfortable doing this for even their flirtations. We’ve got to implore and help our younger employees develop this interpersonal muscle. Now, you asked about what is it that they’re looking for? Well, the three main leadership characteristics that they are looking for that I emphasize a lot of my workshops and speech around are inspirational leadership, autonomy, and transparency. Those are the big three. Many times people misinterpret what those things should be, and that’s what I spend my time on.

Fred Diamond: If you’ve reached leadership in an organization, you have to have that passion, right? You have to have that commitment or else you’re going to get exposed and you’re not going to make it to the next level. Usually, one of the reasons why you get promoted is because you have the passion. What could be some of the tactics that managers could do to bring that passion, the fulfillment to people who may be struggling with that?

Chris Tuff: There’s this tension that also lies in this idea that the perfect job exists for these young people, and that’s the influence of social media. It’s up to us as leaders. The tactic I do, I call it my 70/30 rule. It’s my job as a leader that 70% of your job should be firing you up and in your zone of passion. But I’m going to tell you straight up right now, 30% of your job is going to suck, and it’s not going to be fun.

I want to take your job description in your first week and figure out what’s in your 70% zone of awesomeness and passionate and what’s in your 30% zone of suck. Then when they go through two weeks of doing Excel, if they’re a super extroverted person like me, I hate Excel and budgeting and stuff, you know you just got to break through to the other side. I’ll go into a lot of organizations where I’ll ask these younger employees, is 70/30, is that the right ratio here? They’re like, “No, it’s like 30/70 where 70% of my job sucks.”

I then turn to leadership and say, now it’s up to you all to help your employees develop some more of these passions, whether it be through side hustles or allowing them to work on projects and other areas within the organization, but it’s up to you to help offset that. You juxtapose that also to this fact that the tenacity and resilience muscle isn’t near as strong in these younger generational people. That’s statistically backed. Once again, it’s a product of snowplow parenting, parents taking every obstacle out of their way and once again, social media getting instant gratification, the guys on Lamborghinis with $100 bills, like that you can all of a sudden just do it. It’s all of those things that I really focus us expanding our viewpoints on but also relieving the tension, and everyone’s overwhelmed.

I’m getting brought into all these organizations because no one can hire or retain talent, especially the younger ones. We got to step out and assess this with a broader perspective. What I run up against the most in Xers and Boomers, the one thing is, statistically you look at the data, what it is that everyone wants? Everyone’s like, “Yeah, I want that too.” But the one thing I run up against is, “Well, I had to do it this way, why don’t they?” It’s this balance that I’m trying to bridge the gap on.

Fred Diamond: I have a question about a little bit of a converse here. Again, we talk about authentic relationships. Chris, we talk about, “Hey, sales professionals”, every day on the Sales Game Changers podcast, “Here’s what you should do.” Yes, we want to have authentic relationships with our customers because even though we’re not going to be asking them immediately – and if we do, we’re going to get shut down right away, because nobody likes the concept, the connecting click, or the pitch slap, I’ve seen a lot recently. No customers. I guess there must be some because people keep doing it.

Give us some insights from the customer perspective. Why would the customer want to also engage in an “authentic” conversation with you? We know why we want to do it because we want to develop this relationship that may lead to something a month, two months, three years from now, because our job is to sell. At the end of the day, our job is to provide service, etc., but companies are hiring us because we need to sell their stuff. Talk about it from the converse. The customer, we know why they’re resistant, but why might they get value in this type of engagement as well?

Chris Tuff: Deep down as human beings, it goes down to Maslow’s hierarchy of needs. If you go back to the basics, and you look at what it is that everyone wants, everyone wants to feel loved, appreciated, recognized, and connected. We all crave this connection deep down even if we don’t admit it. There’s a huge difference when someone reaches out on LinkedIn, and they’re like, “Fred, those books you wrote, it changed the way I look at Lyme disease. I know a handful of people that…” You’re going to respond to that. Absolutely going to respond to that.

Because I can uncover just through a little bit of research as the salesperson calling on you, what it is that your desired purpose and things you’re working on are. It’s going to make you feel pretty good because you’re like, “Wow, it’s starting to work.” Then I bet you’re going want to say, “I want to connect with this person”. Then when you see in my approach with this saving your asks mentality, this actually feels, “This is authentic. I don’t think he has anything up his sleeve. Wow, I want to get to know this person a little bit better”.

But once again, it’s up to me to still continue to offer value for you given these things that I am influential on, outside of just the thing that I am selling. That’s where I get to as fast as possible with any relationship. I try to get to a point where I can sit across from that person. I can do it pretty quickly now. What fires you up? What is your dream? When they tell me that, I’ll do anything in my power to connect them with someone in my network to help them take one step towards it. If it’s writing a book, I’ll send them my nonfiction book planner. If it’s a better understanding of themselves, I’ll take them through my culture index personality quiz that I use. It’s up to me as the salesperson to still offer value and some form of step towards you taking action on the things that you desire. As the being sold to person, you’re like, “Wow, this is amazing. This is new, right?”

It’s one thing saying, it’s another thing doing, and what drives me crazy with a lot of these authors and speakers is they say one thing and do another. I practice this stuff and part of how when I was writing Save Your Asks, I was like, I’m going to use this as a touch point to create relationships with the untouchables. One of the guys I interviewed for it was the guy, serial entrepreneur that’s super private. I’m not going to disclose his name, but I met him in the process of writing the book. I’ve now Shawshanked and developed that to a place where he just flew me out to Kelly Slater surf ranch. It was me, Eddie Vedder, Kelly Slater, Drew Brees. There was 15 of us on this manmade wave and I’m like, “How did this all happen?” I’m best friends with this entrepreneur and I’m like, “This is crazy.” Not once have I gone in for an ask. This is now three years later, but I look at what’s happened I’m like, this stuff really works. How exciting is that? That’s one of my ways to inspire.

Fred Diamond: One thing we’ve learned over the last two and a half years, it’s really funny, I tell the story many, many times. Right before the pandemic, I did a show, it was with a sales leader at LinkedIn. Her name is Alyssa Merwin. We talked about vulnerability. I said, “Why are you so successful as a sales leader?” She says, “I’m very vulnerable. I let my people know that and I wavered on my sleeve,” type of thing. That was a unique approach prior to March of 2020. Now, like I say, everybody is vulnerable, but people open up.

The other thing too I want to say is, back to my question, I loved your answer. Not every sales professional is doing this. Not every sales professional is really interested, really, to be honest with you, in what is going on with their customer beyond a cursory question just to make it seem like they care. “Okay, great, good, he just answered the question about how he’s doing. Now, let me tell you about my new print managed service solution and it sounds like you’re struggling with managing your printers.” Well, no, I’m not.

But here’s the other thing, too. If you’re a sales professional, Chris Tuff, you should be a sales professional for the next 15, 20 years of your life. Back to the Shawshank example,  I just got a customer recently who I’ve known for 15 years, and we haven’t had one transaction and we’ve gone years without talking not because we didn’t talk, we just did talk. If you keep being consistent in your message, salespeople out there, the mechanisms like LinkedIn, whatever it might be, and you continue to Shawshank as Chris calls it, and to touch the right way and you be authentic and you be a good person, then eventually, it’s going to shine through and hopefully there’ll be a need at some point.

Chris, first off, I want to acknowledge you for the new book, Save Your Asks and for The Millennial Whisperer. You’ve provided so much value to sales professionals and entrepreneurs and business owners out there with your unique approach. I just want to acknowledge you. You actually live in Atlanta where I went to college and you went to college in Nashville where I’ve spent a lot of time. I spent a lot of time on the Centennial Square at the Parthenon and Pancake Pantry. Do you ever go there? Pancake Pantry?

Chris Tuff: Oh, yeah, the lines are crazy.

Fred Diamond: Very first time I went there, I actually ordered a goat cheese omelet, which was a mistake. Anyway, I want to acknowledge you. Chris, as we like to end every Sales Game Changers podcast, give us one final action step. You’ve given us 15 or 20 great ideas, give us one specific action people should employ right now to take their sales career to the next level.

Chris Tuff: It’s going to sound super simple in nature, but I promise you this works. It’s video text messages. There’s all these services like BombBomb and that’s fine but all I’m saying is as you’re talking to prospects, as you’re shawshanking, send video text messages as much as possible and put into application. I speak at a lot of events, and I meet these executives. The way that I’m able to take it to the next level so quickly is I do it with video text messages.

I just say, “I met an executive of Fortune 100 Company six months ago on a retreat that I was hoping to lead and then sure enough, I did video text messages. I hosted him at dinner at my house with my family and then he just hired me to do a huge global thing for them.” Send that video text message to whoever it is that you are courting. Here’s what’s so fascinating is even if it’s someone that’s never video text messaged back, they will always video text message you back. It becomes this kind of back and forth to where you’re able to move to that place of authentic connection faster using technology.

Fred Diamond: That’s a great idea. I’m actually going to do that right now. I’m going to hang up when we do today’s Sales Game Changers podcast, and I’m going to send three video text messages, which is something I really haven’t done. I’ve done some audio, but I love the idea of the video texts. Once again, thank you everybody for listening. Thanks Chris Tuff, the author of Save Your Asks for the great insights. My name is Fred Diamond. This is the Sales Game Changers podcast.

Transcribed by Mariana Badillo

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