EPISODE 461: Todd Dewett on How to Be More Authentic in Your Sales Efforts and Why You’ll Fail if You Don’t

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[EDITOR’S NOTE: This is a replay of the Optimal Sales Mindset virtual learning session sponsored by the Institute for Excellence in Sales on September 19. 2021. It featured an interview with best-selling leadership author Dr. Todd Dewett, author of Live Hard.]

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TODD’S TIP: “When people say, “Why does authenticity matter?” I go, well, do you want comfort, do you want understanding, do you want rapport? That’s the relationship foundation upon which anything else that might happen will happen, and it begins with being a human being who’s a little more real, authentic.”


Fred Diamond: We’re thrilled today, we have Dr. Todd Dewett and we’ve known about Todd for a long time. He’s a best-selling author, he’s written five books. Show Your Ink, Live Hard, The Little Black Book of Leadership. Todd, prior to the pandemic I was doing these, we weren’t doing them as webinars. I would go to people’s offices and I would interview sales leaders in their office about their journey in sales and how they became sales leaderships. Lessons, tips, those types of things.

I did a show with a VP of Sales from LinkedIn. Her name is Alyssa Merwin, she was basically the Head Sales Leader for the Sales Navigator and Premium products to corporate. We talked about vulnerability, we got like 10,000 views on that and had about 5,000 downloads of the podcast. It was very big topic. I posted on LinkedIn, as I always do, a whole bunch of people commented.

Then the pandemic kicks in and we talk about that all the time, we talk about empathy, we talk about transparency. You are one of the world’s foremost leaders on authenticity. We want to get really deep into why it’s so critical and will it continue? We talked a lot about empathy, everybody on the planet has gone through something similar over the last 18 months and everybody’s experience has been different. They’ve had to deal with the COVID side, then they’ve had to deal with the financial side and then whatever the third thing is that they’ve had to deal with personally.

Let’s get deep and let’s talk into this. First of all, it’s great to see you. Thanks again for joining us today. You’re down in Houston, my old stomping grounds in the mid-90s, I was there for Compaq Computer. Let’s get started, define authenticity and I want to get really deep for the sales professionals listening and watching today. Not just on the 50,000 foot, but I want to get really deep as you tend to do on how they can take this moving forward. Quick definition, let’s get started.

Todd Dewett: First of all, thanks for having me. I’m so glad you had a great relationship or experience with LinkedIn, love those folks, they’ve been so kind to me and we’ve made so many courses together, and they’ve made me think about this issue. When I started branding myself as a leadership expert years ago as something more than just a broad leadership expert, the thing that I landed on for a whole lot of reasons is authenticity, which really can be defined simply as being a little more straightforward, unfiltered, honest, in-the-moment, forthright, candid, owning what you want to say.

That sounds easy, maybe to some people it sounds a little much. But the reason I talk about it – and I’m not the only one, there are a few thousand voices that are obsessed with authenticity just like I am – is humans have natural tendencies and we go to work and deny them hardcore every single day for pretty good reasons.

You know this. We go to work, salespeople in some ways are just like any other professional. They want to meet the expectations of those around them, people who matter to them. So we then sensor a little bit, filter a little bit, do what makes sense according to what we think the norms, rules, regs, expectations are in a given moment. And this is important for your listeners to hear, that makes you socially intelligent, but – huge ‘but’ – what I like to remind people of and the reason we talk about authenticity is we actually do that too much on average. What we bring to an interaction then looks overly done and polished, a truncated, dare I say, fake-ish version of ourselves.

Sales in particular, I know that’s your world and I got to tell you, I love it when people say, “I couldn’t be a salesperson.” As a leadership guy who talks about relationships, I laugh. Everybody’s in sales, you know this and I love reminding people of this. I don’t care what you do, but especially for people actually in sales, everything comes down to relationships. Is there or is there not comfort, understanding and rapport? Without those things, forget about it. When people say, “Why does authenticity matter?” I go, well, do you want comfort, do you want understanding, do you want rapport? That’s the relationship foundation upon which anything else that might happen will happen, and it begins with being a human being who’s a little more real, authentic.

Fred Diamond: It’s interesting you would say this. I was very involved with a series of personal development workshops for a portion of my life and now that I think about it, it was about authenticity. One of the most common phrases was, “You’re being very authentic in your inauthenticity.” You talked about the rehearsed, scripted, “I’m really concerned about you.” Talk a little bit about why people resist it. Is it just how they’re raised? People are taught to be too kind or courteous? Talk a little bit about that.

Todd Dewett: Let me start with what I think you were alluding to there, which is people thinking they’re doing the right thing and coming off like they’re acting. I love to tell people this and let me start with a reminder. I’m a recovering social scientist even though I speak practical speak these days, so I’m not making these things up, I’m just repackaging good things we learned in the organizational sciences in the last 50+ years.

Listen, when you’re insincere, a person of average IQ most of the time will sense that and you will thus – even if you had good intentions – be doing damage to the conversation, maybe to the relationship. I really think it’s important for people to remember that. Now, your next question, why do we do this? Your gut was on the money. We were trained in a variety of ways to be low-risk and polite in social settings, and as you know, that varies by culture hardcore. But it’s still true across cultures. Even in expressive wild and west US, it’s still true here. We were raised with, “Yes, ma’am. No, ma’am.” Raised with, “Listen to adults, don’t speak as much.” We were raised with, “Respect your pastor, your teacher, your older neighbor,” all those things. These are good things, by the way. The question is, do good things sometimes have adverse outcomes we didn’t expect? Yes, they do.

What we do is we educate, allegedly, people and we send them to work for good men and women in corporate organizations around the world and then they go in and they are so nice. They’re the opposite of candid, it’s hilarious. Great leaders almost have to beat kindness out of people. That’s going to sound strange, but I’m being honest here and I’m not suggesting we want negative, ugly, mean-spirited people in the least. We don’t need that at all, we have a few more of those folks to get rid of.

Having said that, we also want real talk. We want people’s opinions on the table now, not later, we want to get to the truth of it. We don’t want people just doing the, “Yes, ma’am” routine to their bosses, we don’t want people sitting on ideas that might be useful, etc. How do you start that? It starts not with a mandate, “Hey, it’s in the employee handbook, thou shalt be more honest.” No, doesn’t work. The only thing that works with humans is interesting things from other humans, which mean leaders who have the microphone and the most power have to start modeling it.

One of my favorite ways to talk about education in any form is modeling it. Once they start acting a little more authentic, others will follow suit which is why your comment about humility hits me like a brick, because authenticity isn’t just simplistically about being candid. What are you being candid about? That means not just talking about the things you’re good at, the wins you’ve had, the things that make everyone go, “That’s a really competent, interesting person.” That’s too easy. We focus too much on that, it gets a lot of people in trouble in terms of relationships.

What then makes candid work? Human stuff. Times you went through a learning moment. Screwed up, failed, had a great setback that taught you something amazing. Talking about humility and vulnerability, the things that we usually hide, in fact, are the things that usually build the strongest bridges if we figure out how succinctly and kindly to share those issues. Now, I don’t want anyone hearing me and going, “That makes sense, I’ve been waiting for somebody to say it. I’m going to start talking that way every day.” Don’t do that.

I do want to tell you, most people never do it because they want to act like they’re perfect when we all, of course, are imperfect. But you are supposed to do it three, four, five times a year with your team or on the podium at the conference or whenever it makes the most sense. Not five times a week, but five times a year. Otherwise, you’re missing out on opportunity to make people, number one, understand you a little better. Number two, and this is the one no one ever sees coming, you make people feel more human when you embrace moments like that because then they can say to themselves, “Not only do I know that person a little bit more, but guess what? I feel a little more okay about who I am because man, can I relate, I got some hilarious stories too.”

Fred Diamond: Todd, questions are flying in here. You’ve thrown a whole bunch of things out there. If you think about sales, you mentioned relationships and you’re one of the world-renowned experts on relationships and authenticity in relationships which is absolutely critical. In sales, you basically have three. You have a relationship with your leaders, your management. You have a relationship with your team and if you’re a leader, that could be downward as well. And of course, you have a relationship with your customer, and you could also say you have a relationship with your partners and vendors, but we may or may not get to them. I want to talk in all three contexts, how do you grow the relationship authentically with your leadership? How do you grow it with your team? Then how do you grow it with your customer?

But first, we have a question here that comes in from Mick, “I really don’t like being confrontational. Todd, cure me or am I stuck?” That’s a clever question, nice little twist there, Mick. Talk about that and then I want to get into authentic with leadership, with team and with customers. Answer that, I also don’t like being confrontational.

Todd Dewett: Mick, I’m intrigued by that. Very few people enjoy being confrontational, that happens out of necessity in a situation. But generally speaking, most people don’t enjoy it. I’m curious why you ask that because I didn’t say confrontation, the need for or the likelihood of it in any way. If what you’re suggesting is that being a little more candid will be perceived as occasionally confrontational, I’m busted and I will go ahead and say, thank you for saying that. Because even though I am a pied piper for authenticity, even though it is in short supply and I will never stop talking about it during my career, there is some risk to any useful behavior at work.

For authenticity, the risk is that people don’t appreciate personal things as much as straight business talk. There is a risk that they won’t like what you say. There is a risk that they will just judge it as not sound. There is a risk that they will judge it as an upfront to them because you’re not just saying, “Yes,” and, “I like your idea.” I could go on, but the thing I love to summarize in answering your question, Mick, is that those possibilities statistically speaking are right here, and that most of the time there’s a huge need to increase candor and push conversation forward. The average response is not anger, which makes you feel confrontational, the average response and really the most typical is intrigue and reciprocation because most humans like a vibrant conversation instead of one that everyone knows is fake for all the obvious reasons.

Fred Diamond: One thing that we talked a lot about in the last 18 months is the fact that in the customer relationship for the sales professionals, you need to bring what we were calling extreme value. Customers don’t really need you in sales as much as they once did because they can get the information on the internet or via social media. We actually did an interview last week with a VP of Sales at IBM, her name is Jennifer Kady. She’s been at IBM for 22 years, even she said that her customers know what they want before they even reach out to us being in the sales organization. We have to show them such extreme value.

Todd, let’s just go to customers first since I’m broaching the subject. If you think about it, customers don’t need to hear from you unless you’re bringing them something of value. They’re busy, they have their projects, they have things that they need to accomplish here. Let’s broach authenticity with customers for the next five minutes. As it relates to the concept of bringing value, we hear this a lot. People think relationships are about, “Our kids play little league together,” or, “We know each other from the golf club,” or something like that. But relationships are getting more about what is the value you’re bringing me, and not from an artificial perspective but I got big challenges now and the pandemic has made it even bigger for me to accomplish my goals. Let’s get deep into this as it relates to you as a sales professional with your customers.

Todd Dewett: I have to say value’s always going to matter, but I’m going to push back just a little bit. I’m always an outsider on conversations because leadership people get brought in in all kinds of functional discussions and I’ve got to tell you, I’m going to push back a little bit. The reason we care and we know in the sales world we care about long-term relationship building is because short-term you’re not always adding extreme value. You can’t, what’s that? A max a sale every single time you touch base with somebody? No.

The truth is – and I’m going to be provocative on purpose – the goal is not max value short-term, it’s extreme value long-term. Short-term, it’s to be a positive addition to their interactions, not a painful, just barely tolerable or negative addition to their interactions in a given time period that you might talk to them. That is to say, sometimes you’re going to push solution services, products, etc. Other times, you’re going to be talking less about your solutions, more about their problems. Less about their problems sometimes, more about life.

These are the foundations of leadership, so your expectations going into one interaction versus what you expect to get out of the relationship over 50 interactions within a year or three are very, very different. It’s about positive relationship value added, and that is different than the solutions you’re offering as an organization. Sometimes they’ll be in the conversation, other times you’re just supposed to be someone who cares, is authentic, is checking in, is listening. Listening is one of the most underpriced product a salesperson sells, it blows my mind.

When humans believe – and it has to be sincere, we’ve said that several times on purpose now – others are listening and attentive, caring, not acting like they’re listening, and wanting to understand, it’s one of the most valuable things they’ll ever see. They love that, it makes them feel affirmed and what more can you do as a salesperson building a relationship than help someone feel understood, heard and affirmed?

Fred Diamond: Todd, whenever somebody mentions the word ‘listening’ I always reply back, because listening comes up all the time. I ask sales leaders, “How can you be a better sales professional?” “You’ve got to be a better listener, two ears, one mouth, 66% solution.” Todd, you’re the expert on this, give us two examples on how sales professionals listening today or watching today can be better listeners.

Todd Dewett: There’s a short-term/long-term way to think about that. Short-term, you listen by saying nothing, by using eye contact – by the way, you’re not supposed to use eye contact in any situation full time, that’s weird. Everyone says eye contact’s great, they never tell you the truth. The truth is you need 70% – 80% eye contact or it gets strange. The rest of the time, you’re supposed to be looking and I’m going to give you the answer. You’re going to look down to where you’re taking notes because a great listener wants to show the importance of what they’re hearing by capturing some of the essence. Note, note, note, that’s what you do, then you go back and look at them. That’s one answer.

The second answer is you can bring into a conversation something that you learned about them at a prior time. One of the best ways to show listening, understanding, maybe even caring if you feel it, if you mean it, is to bring up something. “You remember the conversation that we had last time about the…?” Now they know you’re invested in a long-term, ongoing, not a one-time conversation. I would say a lot of looking, nodding, note-taking, really trying to not speak. Then number two, bringing up an occasional thing or two, not much that sounds like it’s contrived, just a thing or two from the past that shows them, reminds them they’re part of a continuing conversation and you’ve been listening.

Fred Diamond: That is a great answer in a couple different ways. One is we’ve had so many amazing leaders like Jennifer Kady, she was at IBM for 22 years, and we had Tamara Greenspan who’s been at Oracle 30 years and they talked about the lifespan of the relationships with their customers. “I started working with this customer 30 years ago and now I’m working with them again.” What people need to remember is that salespeople may move jobs and stuff, but customers typically don’t, especially if they’re in industries like government or healthcare. They’ll want to stay in their jobs if they’re in IT or finance or operations. They don’t move around as much as we do.

I want to say one quick comment, your answer about notetaking was brilliant. Our good friend, one of the good friends of the Institute for Excellence in Sales, John Asher, would say, “Ask if you can take notes.” Say, “Can I take notes?” Not, “Do you mind if I can take notes?” Because the answer’s always going to be no. You always want to say, “Can I take notes?” The answer’s always going to be yes and you’ve already gotten the first yes from a customer. Great answer, Todd.

We’ve got a bunch of questions flying in. I’ll just do one quick follow-up on notetaking, our good friend Jill says, “A question about notetaking. iPads, iPhones or good old pen and paper?” What are your thoughts on that, Todd?

Todd Dewett: Thanks, Jill. Two competing thoughts here. One is what’s most comfortable for you to accurately, quickly get what you need to get? Number two is what are they doing? Because there is some psychology which has hit the sales world many times around the idea of mirroring, which somehow makes a lot of people comfortable. You might want to consider that, but then again, because I love sincerity and authenticity, I say don’t get hung up on mirroring. Maybe that’s worth looking at, but don’t get hung up on that, do what’s comfortable because it’s not disruptive so honestly, Jill, it won’t matter that much. As long as you’re doing 20%, 30% of taking some notes and then listening, they’re not going to care what method you’re using, they’re just intrigued that you’re trying your best to listen.

Fred Diamond: Show them that you care, show them that you’re interested, that’s what they love. One of the great quotes that we got on one of our past shows was from a guy named Gary Milwit, his strategy is make everybody you talk to feel important and it falls in line with this as well. We got another question here, Todd, that comes in from Dan. “Is there a way to establish authenticity in email? In other words, if I’m introducing myself to a prospect, how do I establish authentic credibility?”

Todd Dewett: It’s a great question and it is possible. It’s a whole lot more difficult because any kind of communication becomes easier and more full of possibilities the richer the communication channel is. The richest by far is face-to-face. Second would be what we’re doing right now or some version of it, video live talking to each other. Then there’s the phone, then there’s email, then there’s text and so on. It’s not considered a rich medium, that’s the first thing I have to say anytime anyone asks me about anything in email. Number two, I have to say that whatever you write is going to be interpreted differently than you probably think it is. That is the simple compromised nature of writing inside an email program.

We have a love affair with the efficiency, but believe me, the effectiveness is very questionable which is why, if you want to make an impact and be authentic, I would say that’s not the vehicle for you. Use that to do mechanical operational things like get a phone call or a video call. Then you have much higher odds of having something authentic about yourself be perceived as such. I don’t think it’s impossible, I’m not avoiding answering. You can use words to talk about ideas that indicate you’re full of raw, awesome realness if you want to, but how they’re interpreted is less predictable and has less impact, even if interpreted correctly via email as a channel. I would say, use it for setting appointments and other mechanical things and don’t try to make super relationship inroads with that channel.

Fred Diamond: The second audience we want to be talking about is the authentic relationships with your leadership. Let’s go upwards. We have a lot of leaders who listen to the Sales Game Changers podcast, but let’s do it the other way around. Let’s do it from the sales professionals who report up to somebody, because it’s a challenge. We all talk about transparency and it has to be transparent so that your company can understand where sales are coming from and we talk a lot about asking for support.

I did a LinkedIn poll three weeks ago on a Thursday, I had something like 80,000 people who viewed the poll and like 1,000 votes on, “Are you comfortable asking for help?” Give us some of your insights on, you’re a rank-in-file or first-level management, authentic communications and relationships with those above you.

Todd Dewett: I love the question, it’s very important. In fact, you didn’t know this but I’ve got a course on that over at LinkedIn Learning. I love the topic because it’s a terribly important relationship, maybe the most in your career is the relationship you have with your supervisor. And if you’re only going to them when you’re asking for help, you’re not managing that relationship correct at all. That is a thing you have to do. But the question is how can you add value? And you’re going to start by trying to realize this, their world is different than yours. They’re focused on some of what you’re focused on and they’re focused on a lot of things you are not focused on. You have to understand that before you go speak to them, number one.

Number two, make sure you think long-term a little bit about the variety of interactions you have with them. How do you get authentic? It’s not just talking about what you know, what you need, or asking for help. It’s about things that might help them, a connection that you can help, an insight that from a win or a screwup or the team’s win or the team’s screwup that you can offer them. That helps them with that other thing you know they’re doing next Wednesday that doesn’t involve you, because you’re just trying to be a great colleague, not just a great employee to them. Those are versions of authenticity that talk about you, that add value, that get a little candid because you’re talking about learning, for example, and that requires humility. That’s different than, “Let me tell you what I know and let me tell you the help that I need.” Those would be the places to start, for sure.

Fred Diamond: I get a lot of that from junior sales professionals who have challenges, “They expect me to make 50 phone calls and I can only make 40.” I’m like, “Listen, your boss is managing 6 people which means he’s responsible for 300 phone calls, not just the 40 you can’t do. And his boss is managing 3,000 phone calls, so that’s why you need to make the 50 phone calls if that’s what your company says you need to do. You need to understand that.” It’s a beautiful answer.

We talked about the relationship with leadership, we talked about the relationship with your customers. Talk about the relationship with your team, and you mentioned colleagues before. I’m just curious because of social media and of course, we’re going to start getting back, but what is your suggestion for people? Should work and home be separate? Should you be buddy-buddy with people you work with? They’re not really your competitors, they are your teammates but with a lot of junior people you see things on social media that are like, “I don’t know if I would have done that with my coworkers back in the day.” Give us some of your thoughts about authentic conversations and authentic relationships right now with your team members.

Todd Dewett: I’ll tell you what, man. It’s a whole other couple of podcasts you’ll have to do with someone other than me about the precarious nature of social media, but the answer to the questions you just asked were no and no. Are you trying to be best friends? No. Are you business-only? No. There’s good science here and there’s also my world of experience, and I want to tell you this. You’re supposed to be first and foremost a professional. What are the tasks, roles, and responsibilities? How do I also serve and help my team on the task side based on prescribed goals that we all have? That is the foundation and it’s not impressive, it’s not enough to make you a super star, it’s really not.

What you have to do beyond that is also be a person because what most humans want is a connection and some sense of purpose. Believe it or not, no matter what you do, if you’re in the right relationship, the sense of purpose can be realized so you’re not supposed to be best friends. That’s rosy-colored glasses problems that we don’t want. You’re supposed to be – and this is the beautiful middle sweet spot that’s always neglected which gives me room to play, as you know. You’re not supposed to be just a competent professional, you’re not supposed to be best friends. Right in the middle is a professional who cares about the bigger life we’re all leading, who cares about your feelings, your interest, your likes and some of those friend-like things but stop short of trying to put that in terms of priorities ahead of the business goals we’re all chasing. You want to struggle with that middle ground, that is the best answer I found so far.

Fred Diamond: Before we ask you for your final action step, I want to thank you for all the value you’re bringing today. I want to go back to the last thing you just said and that’s something that we learned. Actually, I have a comment here from Dan which says, “If you’re a professional, be a professional.”

One thing we learned in the beginning of the pandemic, Todd, we started doing the webinars and transactions weren’t happening for obvious reasons. Everybody thought 2020 was going to be their best year ever and then all of a sudden, everything shifted. If you were selling cloud services, you were probably doing a ton of transactions. Obviously if you’re selling masks and respirators and those kinds of things. But for the most part, most transactions really slowed down and we kept saying, if you’re a sales professional, what should you be doing? Because you’re not making transactions right now, work on understanding your customer, work on your presentation skills.

Before I ask you for your final action step, Todd, this may be a broad question, define professional as it relates to context here. You’ve given us some really great points about long-term, and I loved your answer to Dan before about the email should be designed to get you to the phone call, which will then get you into the relationship. I’m just curious, from your perspective, how does professionalism play into the authentic matter that we’re talking about?

Todd Dewett: I’ll be honest with you. I think this is going to encompass my last thought I would offer as well. A professional is a person that is competent or that is working very, very diligently to be competent, that cares about a variety of things, even if they’re not yet world-class at them. That is communicating, that is supporting their colleagues, that is building the task knowledge to do what they were hired to do and maybe even branching out in a backup sense to be useful and sometimes a safety net for others on the team. That’s the minimum for me about what it means to be a professional, but how do you do that?

If you were then to say, Todd, we’ve got to go in a minute, what’s the one last thing you really want to share with these folks? I would say, and it builds so nicely on what I just said. All of the things that we just talked about can really be seen as skills. It is not true that you were born simplistically great at sales or not. You might know someone, believe me, on average it’s not true, though. What is true is anything communication related is a skill that you can build. You want to end my little rough definition of a professional? It’s a person that knows that what they know today isn’t good enough tomorrow, certainly might be dead, not even on the shelf in five years, so they take learning and growth as central to what it means to be a professional. Today, this is what’s so fun to share with your folks, there’s a million ways low-cost and free to continuously learn for the rest of your career, now more than ever.

Fred Diamond: Continuous learning. Todd, I want to thank you for not just what you’ve given us in the last 30 minutes, but when we announced that you were going to be one of the guests on our Optimal Sales Mindset, I got a whole slew of people who reached out and said, “About time you got Todd on the show,” or, “Good job, I look forward to hearing from him.” Nick, who asked a question before says, “Great job, Todd.” We have a comment here from Suzanne, “Thank you so much, Fred, for bringing Todd.”

I want to acknowledge you for all the great work that you’ve done not just for sales professionals that we try to help take their careers to the next level, but leadership, teams and executives all around the globe. Great companies like Google and IBM, Pepsi and hundreds of more who you have impacted. I want to thank you, I want to thank all of the listeners of today’s webcast and all the listeners of the Sales Game Changers podcast. Thanks, Todd.

Todd Dewett: Thanks, take care.

Transcribed by Mariana Badillo

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