Episode 473: Smarter Sales, Not Faster: Wes Schaeffer on AI, Trust, and Real Conversations
In this episode of Making Sales Social, host Brynne Tillman sits down with sales veteran and author Wes Schaeffer to unpack what’s really holding sales teams back in today’s AI-driven world. Wes challenges the obsession with speed, automation, and shortcuts, arguing that most sales problems don’t come from a lack of tools but from a lack of clear thinking, discipline, and human connection. Together, Brynne and Wes explore why doing things faster often creates more friction, how “busy work” hides poor strategy, and where AI and automation can actually support, not replace, real sales conversations.
You’ll hear practical insights on: Why sales success comes from being smarter, not faster The danger of over-automating trust-based conversations How AI should support thinking, not replace it What most sales teams misunderstand about productivity and pipelines Why human curiosity and follow-up still outperform any tech stack If you’re using AI, CRMs, or automation in sales, and wondering why results haven’t improved, this episode will help you reset your approach and refocus on what truly moves deals forward.
View Transcript
Wes Schaeffer 00:00
Humanity is the next killer app. People equate it to the medium—Facebook, Instagram, whatever—but at the end of the day, it’s just: are you social? Do you remember there’s a human being on the other end of the screen?
Bob Woods 00:15
Welcome to the Making Sales Social Podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching their clients so you can leverage them for your own virtual and social selling. Enjoy the show.
Brynne Tillman 00:40
Welcome back to Making Sales Social. I’m Brynne Tillman, and today I’m joined by Wes Schaeffer, the Sales Whisperer. Wes is a sales strategist, Air Force veteran, and Brazilian Jiu-Jitsu Black Belt. He’s also the creator of the BJJ and Biz Conference and Podcast. For nearly two decades, he’s been helping sales teams and entrepreneurs master the balance between automation and authenticity, growing revenue while building real trust. He’s worked with companies that have gone from flat to record-breaking performance, often increasing retainers, lead flow, and pricing power—not by adding noise, but by simplifying what actually works. We’re going to dive into the mindset, mechanics, and message behind sustainable sales success, and why shortcuts never last. Well, Wes, welcome to the program.
Wes Schaeffer 01:40
Hey, I need that intro. I’m going to snip that and use it for all my own intros from now on. Oh, good, yeah, feels kind of good. I feel like I’m raising my prices after that intro. All right, all right.
Brynne Tillman 01:56
Well, I’m happy to take a commission, for sure. No, I’m kidding. But I’m really excited that you’re here, and I’m excited to dive into some of your magic. I have, hopefully, questions you’ll enjoy as much as the intro itself. But before we do, we ask all of our guests the same first question: what does making sales social mean to you?
Wes Schaeffer 02:20
I’ve been saying lately that humanity is the next killer app. Social selling is the medium. People equate it to the medium—Facebook, Instagram, whatever—but at the end of the day, it’s: are you social? Do you remember there’s a human being on the other end of the screen? Are you meeting them where they are? Are you answering their questions, calming their fears so they can relax and find the truth? Because sometimes the truth is, no, we’re not a fit. That’s how I view everything I’ve ever done: helping connect with the human and find the truth. Hopefully, the truth is, you do business with me, but often it’s like, we’re not a good fit. So I’ll help you find the right one.
Brynne Tillman 03:23
That aligns with what we do on LinkedIn. Our tagline is: detached from what the prospect is worth to you, attached to what you are worth to the prospect. I feel like that completely aligns with your perspective. Thank you for that. One thing that stood out to me when I was doing my background research was “shortcuts don’t last.” What’s the most common shortcut you see salespeople taking, and what’s the long-term cost?
Wes Schaeffer 03:59
Common? They take all of them.
Brynne Tillman 04:03
Just common ones you’re hearing, right?
Wes Schaeffer 04:06
Yeah. Chasing the shiny object—they’re constantly trying new things. They optimize LinkedIn, then Instagram, then use AI, then cold email—whatever the cool kids are doing. And again, they forget there’s a human on the other end of the screen. They don’t realize they’re coming across just like everybody else. I get the same emails with the same merge fields: “Hey Wes, I really like how you keep it real on your podcast.” Everybody’s getting the same content. If you sound, look, and conduct yourself like your competition, the only way to differentiate yourself is on price. You have to be willing to be yourself.
Brynne Tillman 05:15
Oh, I love it. So the biggest shortcut is trying to do things faster instead of…
Wes Schaeffer 05:21
Smarter. Yeah, you’re so concise, you’re pithy. I need more of you in my life. That was good.
Brynne Tillman 05:27
I’m all about acronyms and one-liners. As a professional who is deeply dyslexic, those one-liners keep me on track and consistent.
Wes Schaeffer 05:50
Well, you said this was a three-hour podcast, so I don’t want to answer too quickly. I need to string these answers out.
Brynne Tillman 05:57
Three hours would be possible based on our first couple of questions.
Wes Schaeffer 06:07
Listeners would want to—they’ll stick around.
Brynne Tillman 06:09
I have a little buffer if we go over 20 minutes. Talk to me about another thing that stood out: a lot of what I talk about is motivation, but you focus on discipline. What’s the difference, and why is discipline so much more important than motivation in sales performance?
Wes Schaeffer 06:40
I always remember Zig Ziglar said people complain that positive thinking and motivation don’t last. He said, “Well, neither does showering.” That’s why you do it every day. Coming from a military and sports background, motivation is fleeting. I read a quote from a football player: “We play the games for free; the games are fun. They pay us to practice.” Motivation is internal, but so is discipline. Closing a sale is a lagging indicator—just like losing weight. You might want to look good for a wedding or reunion, but do you have the discipline every step along the way: choosing water instead of soda, drinking coffee black, small actions that add up.
I wrote a post years ago about BHAGs—Big Hairy Audacious Goals. People think their BHAGs hold them back because they focus on the end goal instead of what they do daily. Discipline is doing the small, consistent things to reach the big goal. Most people fall flat because they think the small steps are inconsequential. All these little things add up to the big things. That’s why I focus on discipline.
Brynne Tillman 09:08
I love that. I’ve never heard it positioned that way: you have the motivation, but discipline actually gets you there.
Wes Schaeffer 09:18
Daily discipline determines destiny.
Brynne Tillman 09:23
I love that. That’s your one-liner.
Wes Schaeffer 09:28
There’s yours.
Brynne Tillman 09:31
You did good.
Wes Schaeffer 09:31
You’re doing great. I have a two-parter question: you say technology doesn’t build trust—people do. But today we have CRMs, AI, email, LinkedIn. How do salespeople leverage technology while keeping it people-driven and trust-driven, and how can sales leaders ensure they’re not taking shortcuts?
Wes Schaeffer 10:20
Most sales leaders are in trouble. When I started the Sales Whisperer in 2006, I watched Dog Whisperer. Cesar Milan said, “I rehabilitate dogs and train their owners.” I thought, “I rehabilitate salespeople and train their managers.” Most sales managers haven’t had sales management training—or even sales training. Most sales training comes from operations or marketing doing a product demo, then leaving salespeople to their devices: big quota, phone, LinkedIn Sales Navigator—”Go get ‘em, tiger.” Everything is broken: duplicate entries between CRM, marketing, accounting, ERP. Salespeople are frustrated, doing the minimum to make the number.
They forget humanity. I always show a slide in presentations: dating equals selling. I met my wife at a country bar in the ‘90s. Every little detail mattered—what I wore, my cologne, how I approached her. To make any sale, you must make every sale. Everything matters. Do you want to persuade 100 prospects 10% or 10 prospects 100%? Consistently showing up matters. I called my wife the next day—checking the number was right. That effort, consistently showing up, is what counts. People overcomplicate things: perfect merge fields, college references, LinkedIn posts, SEC filings. No. Just show up.
Brynne Tillman 15:57
…in a way that matters to them.
Wes Schaeffer 16:00
For sure, in a way that matters. If I leave a message—a voicemail—like, “Hey, sorry I missed you. This is Wes. I’ll shoot you an email with more info, and I’ll call you tomorrow at 1:00.” You don’t care. It’s a cold call. But if I call tomorrow and say, “I left your message yesterday. I told you I’d call today at 1:00. I’ll send you a case study. Have a good weekend. I’ll call Monday at 8:00 AM,” and you don’t take that call, you’re like, “Who is this guy?” He does what he says he’s going to do.
Then you go back to my first email—oh, that’s interesting. You see I opened the email, clicked the link. Maybe I connect with you on LinkedIn. Now there are three voicemails, three emails, social media touches. Seven touches in three business days. You think, “Hmm, this guy really wants to reach me.” You might still play hard to get, but I’ve piqued your curiosity. Nobody really gets that deliberate and specific. There’s nothing earth-shattering there. It’s discipline. It’s showing up and proving you’re different by being different. I proved to my wife I was interested in her by showing up. Are you showing up?
Some people think, “Should I wait three or five days?” Hit them three times in one day: voicemail, email, social media. If you get their cell phone, text them. Some say, “Oh, you’re going crazy,” maybe—but you’re cutting through the clutter. If you call every three to five days, they’ll forget who you are. If you care enough, reach out and show them you really want to talk—but you better have a damn good reason.
Brynne Tillman 18:15
That’s the key. We typically say: show up with insight and earn the right to get the conversation—bring value and insight. I love that. Because of what I do, I’m LinkedIn-first, but we’re saying the same thing. Touch them on different platforms, different mediums, and figure out which one works. Part of showing up is showing up in a way that matters to them, on the platform that matters to them.
Wes Schaeffer 19:04
Yes. You have to meet them where they are. You are not your client. If I’m not visible on TikTok but my demographic hangs out there, I’ll get good at TikTok. If I’m selling retirement plans, medical treatments for the elderly, or retirement homes, maybe I’ll do a billboard, direct mail, even the Yellow Pages. You have to give them what they want.
Brynne Tillman 20:02
Exactly. When we talk about LinkedIn content, we always say: stop sharing content you want them to consume; share content they want to consume. No point sending stuff they don’t care about.
Wes Schaeffer 20:20
Vegans don’t buy bacon—even if it’s on sale.
Brynne Tillman 20:25
Love that. Brilliant. Caesar Milan’s advice still sticks with me too.
Back to sales: you talk about how ego doesn’t belong on the mat or in sales. How do you coach confidence without crossing into arrogance?
Wes Schaeffer 21:06
That’s hard. Jiu-Jitsu beats ego out of you. In the military, they’d say: “The beatings will continue until morale improves.” In sales, you hire for it. Personality profiles, psychographics—sometimes people are narcissists or psychopaths. You need to weed them out. If they’re young or new, you can help them develop good habits. Many are broken and remain broken.
Salespeople often talk excessively to soothe themselves. Body language reveals it—they hug themselves, rub their arms or legs. They may lie or walk through uncertainty. Many are dysfunctional to some degree. I intentionally went into sales after resigning my Air Force commission. Others start sales because they were laid off or couldn’t find a job. They didn’t go to school for sales, so they don’t feel good about what they’re doing. They talk and talk to convince themselves they’re good.
The more they learn their product, the more egotistical they become: “You need what I have. You’re lucky to get me on the phone. I’ve made Presidents Club three years in a row.” Maybe that’s true, but you’re not getting my money with that attitude.
Brynne Tillman 24:19
Side note: I’m blown away by how much our thinking parallels each other. I’m more motivation-focused; you’re discipline-focused. I’m writing my next book: The Narcissistic Salesperson in the Journey to Recovery.
Wes Schaeffer 24:46
Did something spur that?
Brynne Tillman 24:57
I train salespeople every day on LinkedIn. I started by writing blog posts about the pitches I received—it spurred a lot. I’m surrounded by narcissism; I was raised by narcissists.
Wes Schaeffer 25:28
Do you see it more in men or women?
Brynne Tillman 25:33
It shows up differently. Men show ego. Women show a need to be right. I want you to think I’m amazing. Money motivates me, but affirmation motivates women in this context. Much of this comes from a male-dominated sales world.
Wes Schaeffer 26:29
Fighting as a minority against the stream.
Brynne Tillman 26:32
Exactly. Being right matters more than anything else.
Wes Schaeffer 26:37
Do you see equal percentages of men and women?
Brynne Tillman 26:45
I’m gathering interviews, not data yet. More people like you are emerging—trust-based salespeople who start conversations without being salesy. Narcissists focus on the $12,000 sale and commission, not the solution. You show up to help or refer the right solution. That’s the opposite of narcissism.
Wes Schaeffer 28:34
No, that’s awesome.
Brynne Tillman 28:38
I could talk all day—maybe we will. I have nine more questions, but for our listeners…
Wes Schaeffer 28:54
Captions, they read the captions.
Brynne Tillman 28:58
We have show notes, like Apple/Spotify. As we wrap up, Wes, is there a question I should have asked but didn’t?
Wes Schaeffer 29:16
We could go on forever. I love sales. It’s about serving. You can make as much money as you want if you find a need and fill it. We hit the important questions. Discipline vs. motivation: when grinding, it’s hard to stay motivated. One skipped day matters. Even imperfect effort counts. Showing up daily, despite fatigue or obstacles, builds discipline. Results follow.
Brynne Tillman 32:01
Exactly. Motivation alone isn’t enough—you need discipline. For me, I always reminded myself: “I only need one cookie.” One is enough. Discipline leads to the goal.
Wes Schaeffer 33:20
People can reach me at my landing page: 12weekstopeak.com. Everything is there. I’m moving content to Substack for updates. Follow along for my journey—imperfection and progress, not perfection.
Brynne Tillman 34:53
What’s your Substack handle?
Wes Schaeffer 34:57
It’s my name: west.substack.com.
Brynne Tillman 35:11
Thank you so much for being here.
Wes Schaeffer 35:19
I didn’t hear your dog—you’ve got a good mic. I’ve got seven kids, four grandkids, always something going on.
Brynne Tillman 35:29
I have five kids and two grandkids—lots in common. Thank you so much. Listeners, go to 12weekstopeak.com. Don’t forget to make your sales social.
Outro 35:55
Thanks for watching. Join us again for guest instructors sharing marketing, sales, training, and social selling strategies. Subscribe for the latest episodes, give a thumbs up, and comment what you want to hear next. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.