Old School Sales Techniques That Still Work

In this episode of "How to Sell More," sales authority Jack Daly challenges conventional thinking about selling in the digital age. Speaking with host Mark Drager, Daly shares stories from his thirty-year journey from accounting firm CEO to sales leadership expert.

The conversation starts with a surprising admission from Drager. His father, retired twenty years from insurance sales, pointed out issues in Drager's current marketing approach. While Drager initially dismissed these as outdated ideas, every point proved correct - highlighting Daly's central message that core sales principles transcend time.

"Sales has and hasn't changed," Daly explains, addressing the seeming contradiction. He points to technology as the main shift, replacing his old trunk full of Manila folders with digital tools. But the foundation remains: establishing trust and building genuine connections.

Daly shares practical examples throughout the episode. He describes a Florida company whose sales team maintains desks within their top clients' offices. They work there weekly, becoming part of the client's team. Another sales professional turned her ten biggest clients into vacation companions - proving relationships matter more than traditional selling techniques.

The episode turns personal when Drager reflects on his own sales evolution. He describes moving away from a relationship-focused approach toward pure metrics, only to find his results and satisfaction dropping. Daly responds with insights from coaching 2,600 salespeople: numbers follow relationships, not the other way around.

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I send 30% of potential clients to other experts who fit their needs better. When they need my specific strengths, they won't call anyone else - because they trust me. -- Jack Daly

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Top 3 Reasons to Listen

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Double Your Client Base: Learn why top performers call on fewer prospects but write more business. Daly shows how focusing on select relationships leads to larger sales volumes.

Turn Market Challenges Into Sales: See how shifts in your industry open doors while others quit. Daly's mortgage industry example shows how to sell when competitors claim "the market is dead."

Create Client Loyalty: Discover how embedding yourself within client organizations leads to natural sales growth. Daly's desk-at-client strategy shows how to become an insider rather than an outside vendor.

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More About Today's Guest, Jack Daly

A professional sales coach & speaker, offering dynamic sales keynotes, workshops & corporate culture workshops that inspire audiences to act.

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Jack Daly is a leading sales speaker and trainer with over 30 years of sales and executive experience. Jack’s track record is a testament to his real-world knowledge and extensive expertise in sales and sales management. He started his professional journey at CPA firm Arthur Andersen and rose to the CEO level of several corporations, building six companies into national firms along the way, two of which he subsequently sold to the Wall Street firms of Solomon Brothers and First Boston.

In addition to his comprehensive professional background, Jack holds a BS in Accounting, as well as an MBA, and was a Captain in the U.S. Army. Jack Daly is an Amazon Best Selling Author and has written and contributed to many books, including Hyper Sales Growth and The Sales Playbook for Hyper Sales Growth. Jack is a 15-time Ironman competitor and has completed over 93 marathons in 50 states and on seven continents. He achieves these goals and lives life to the fullest by following his own Life by Design techniques.

Born and raised in Philadelphia, Jack currently resides in San Clemente, California.

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Key Takeaways

• Preparation Sets the Foundation - Study both company websites and individual backgrounds before calls. This homework shapes smarter questions and uncovers natural connection points.

• Selective Focus Builds Results - Pick fewer prospects and invest in those relationships. The math shows concentrated attention outperforms scattered outreach.

• Systems Create Excellence - Build repeatable processes for common scenarios. Excellence comes from practicing responses until they flow naturally.

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A Transcription of The Talk

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Mark Drager: Jack Daly, you have over 30 years of sales and executive experience, working your way up in an accounting firm and becoming the CEO, and then going on to lead many organizations. What I wanted to talk to you about is, at your age—and I say that with respect—but, if I can tell you a quick story: I was talking to my dad a few weeks ago. My dad is turning 70 this year. He was an executive in the insurance field for a long time but has been out of the game for almost 20 years now, having retired at 50. The other day, he was leaning on me, nicely pointing out areas in my own marketing and business that he thought weren't up to standards. Part of me, as a 40-year-old guy, wanted to say, "Wow, you've been out of the game for 20 years; you don't really understand how business is now." I wanted to be ageist about it. But honestly, I reflected on it, and every single thing he pointed out was correct. Everything that was relevant to him in the 80s and the 90s in terms of business is still relevant today. I took action on it and am so glad for the push. So, when I was getting ready to sit down with you, I thought, here's a man who has decades of experience. While we could talk about what's happening in 2023, I'm more curious about the lessons, tactics, and strategies that worked in the '80s, '90s, and the 2000s that maybe people my age are ignoring or are simply ageist about, but they're still just as important as ever. What are your thoughts on that?

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Jack Daly: Well, I love the way you've teed it up, because I get in front of my audiences, and my kids are older than the majority of the salespeople in my audiences. So, I'm sensitive to this. I want to take it out of the audience straight away. The question is, "Hey, is sales different today than it was 20-30 years ago?" And the answer to that question is, yes, it is. And no, it isn't.

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Mark Drager: Okay, you left me hanging. I was like, not anywhere where I thought we were going.

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Jack Daly: True. Let me show you. 20 years, 30 years ago, people did business with people they trusted. That's the way it was 30 years ago. By the way, I think that's more profound and more the case today than ever because we've got all these people drooling all over the internet and everything else, masquerading and doing all kinds of things that we didn't have before. So, where is the trust? I mean, I get attacked all day with LinkedIn trolls and all of that type of thing. So, selling, at the end of the day, is about trust. It's a transfer of trust. True today, it was true before. Can we go again? 20-30 years ago, people did business with people they liked. Has that changed? Because if I don't like you, Mark, I'm not buying from you. I mean, that's pretty simple. And the best salespeople are like chameleons, and they morph into being more like the person they're calling on. You see, people do business with people they like, and they tend to like people who are more like them. So, trying to figure out what kind of personality I am dealing with and then modifying yours is essential to getting to the finish line. Now, if I package those two and say, "Okay, then what is the difference?" For me, it's one word: technology. Technology in the last 20 years has changed the game of selling in a profound way. And a salesperson who isn't taking advantage of it is really losing out on the opportunity. For example, I can remember as a sales guy, 20-30 years ago, in the trunk of my car, there were boxes with Manila files on each one of my accounts, and there were like written pads of paper like this.

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Mark Drager: Up until a few years ago, I just threw out literally folders, Manila folders with business cards, stapled to them. All of the handwritten notes, all of the dead leads, like all of the meetings that just didn't go anywhere. And I looked at these boxes, and I thought, "What do I do with them? There are just hundreds and hundreds of folders from like, eight years out of date." I mean, we just threw them all out.

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Jack Daly: Absolutely wrong. In that very busy trunk of the car, I also had demonstration materials, a void problem, like I'm gonna walk in with two big suitcases full of stuff that I can show. My goodness. We don't need to do any of that. Because there's a website up there; people can go and see what we have, what we do, who we are, how we're different, how we're better, all of those types of things. So, the nature of our conversations now as a salesperson has changed dramatically, or I hope they have because you shouldn't be trying to go in and ask questions about things that you could find out on your own by going to the internet, right? A contact management system and leveraging a contact management system just changed the nature of the game. So, the nature of a sales call today is so much more about asking questions that really go deep after you've done your homework before you've even made the call. So, I was in Phoenix yesterday, and I was working with a group of people. And I said to them, "So, how many of you had ever met me before?" And no one had. And I said, "So, how many of you, knowing that you were going to spend five hours of your life with me today, went to my website and checked me out? How many of you went on to my LinkedIn and checked me out?" Not a single person. And these were the sales leaders of the company I was working at. And I said, "Gang, there are 168 hours in a week—that's math, 24 hours times seven. I protect my 168; I would check out anybody before I arrived, and say, 'Is this person going to be worth my time?' And if you haven't done it with me, now, I'm suspecting you haven't done it with your prospects and your customers. So, you're not leveraging the asset that can be leveraged." And that's technology.

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Mark Drager: But you know, I don't know if this is true, but I've picked up from many conversations over the last—oh, this is painful for me to say—the last 20 years, where it's feature and benefit-based selling. And then it's from feature and benefit-based selling to outcome-based selling, and from outcome to insight-based selling, then insight-based selling to story-based driven selling. And it seems like I've heard for far too long people of a certain age or generation saying, "Guys, things have changed. It's not like it was in the old days." And I would look around the room, and I was typically one of the younger people there. And I go, "I mean, this is the new normal for me." Have there been these kinds of subtle shifts in terms of how we should even be approaching sales? Or again, is it just that we maybe have lost the fact that features and benefits are still really important today because we're all so busy focusing on our purpose, our stories, and our authenticity? Have we lost the fundamentals along the way?

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Jack Daly: I'm going to make it real fundamental. And your audience may disconnect here, but here's a piece of advice: great selling. Just forget people showing up and throwing up and putting presentations on. People do not want to be sold. So what is the salesperson set to do if they're not going to sell? And the subtle change I ask is this: help them to buy. So you've got to figure out where the pain points are, where the pleasures are. And are you the right fit? You know, it's interesting, Mark, I get tagged by people all over the world saying, "Come and help me with my company, here are my challenges." 30% of the leads that come in to hire me, that I could close like that, I send to other people that would be better for them with what they need right now. Because if I can do that, when they really need me for my strengths, for my sweet spot, they're not going to call anybody else because they trust me. I mean, I could have done it. But I know people that major in customer service that would eat my lunch doing that, so I'm moving it over there. Whenever they're going to need somebody to talk about sales on demand, right? So, I watch salespeople who are enamoured with their presentations and their laptops and can't wait to just flip that open and start putting it on me. And if you haven't done any diagnostics, and it's a standard canned presentation, I will close your laptop and usher you out of my office, plain and simple, and you can have the perfect service or product for me, but I'm not allowing you into my world without you really digging in and finding out: Is this a good fit? I'm not going to sell to anybody if my product or service isn't what I consider to be the best thing for them.

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Mark Drager: That is such a good point. The thing that we do most—that's not even proper English. That is such a good point. The one mistake that I think most people make, especially when they come to work with us, is they expect the prospect to read between the lines and connect the dots. They expect the prospect to be able to analyze whatever the heck it is that you're saying, look within themselves, their systems, or processes, their opportunities, whatever it might be, and go, "Oh, here's how I can apply it." In most cases, the prospects could figure it out, but they don't want to; they're too lazy, they don't have enough time, or frankly, they don't understand what the hell you're talking about. And so I feel like if you don't take the time to diagnose the challenge or the issue, and then tailor it, and then present it in such a way as to show how it fits right in with their needs, you're expecting the prospect to do too much.

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Jack Daly: What you just did was validate where I was earlier, which is, that if you're a pro at selling, you're spending a fair amount of time doing your homework before the call. Because the more homework you do before the call, the better you're going to be able to simply tie the dots together for the prospect.

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Mark Drager: Okay, so what are the two or three things that we should be doing? Or what is your approach to doing that homework so we can show up to the calls, really not over-prepared? Because I don't know, maybe it's a myth, but I feel like sometimes I could show up over-prepared and then I take the conversation away from the prospect, and I make too many assumptions. So how do we go about this?

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Jack Daly: Well, you just hit on something really well there. And I'll give you are the answer to that. But before I go, the percentage of time on a sales call that you, the salesperson, are talking compared to the percentage of time that the prospect is talking—I would prefer two-thirds of the time to be the prospect talking and a third on the salesperson. What I find is it's flipped or even worse, right? What we call showing up and throwing up. And so that doesn't work for me. But go to the company's website, go to more than the homepage with a purpose that says, "I want to be very curious about these half a dozen things." In surfing through their website, I just have legitimate questions about it, and I just want to have an engaging conversation. Then that's the company. Now I want to go to the individual, to the person. So I'm going to check them out on social media, check them out on LinkedIn, whatever, and see if there's something that maybe we even have in common. I mean, if you did your research on me, like the group yesterday in Phoenix, well, they would have known that I do Ironmans and I do marathons, and I've played the top 100 golf courses in the United States. I mean, I have enough stuff about me that's out there in the universe, that you'd have to be a rock to not find something we enjoy together. Right? You're wearing a Spartan shirt. And immediately, as soon as I got on, I was like, "Oh, do you do Spartan Races?"

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Mark Drager: Can I tell you, I was going to—I never wear branded clothing on these recordings—and I was going to change into plain black or my sales blue shirt. And I left it on specifically because I saw that you did.

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Jack Daly: Right. So what happened? As soon as we got together, right before we went live, we started engaging in a very human way, which is the strategic advantage in sales. So, people do business with people they like and find a way to have some commonality. And I know unless somebody is just not playing in any of those worlds, which I don't think they ought to be on your prospect list, because they're probably not very good anyway, right? Be selective, be selective about your marketplace. Too many salespeople call on too many people that don't deserve to be called on. When I go in, I look at the very top producers all around the world in sales, no matter what industry it is. They call on fewer people and they write more business. They're cherry-picking, right? The key is they call on the right people. You know, I've had salespeople, 100% commission only, working for me and my companies that are making seven figures every year in commissions. And then I looked and 90% of their business is from 10 people, and they just focused on the ones that really are worth investing in. I have one salesperson who told me, "I actually don't sell, and I haven't sold in over a decade. I just do business with my friends." And I said, "Well, Cindy, did you all go to high school together or something?" And she said, "I didn't know any of them until I called on them. But we evolved in time. We go on vacations together, we go all over the place, we go to dinners, and blah, blah, blah, blah. I hold a golf tournament with the top 10 and give away putters and drivers, you know." Like, and then there are the other salespeople that are mediocre and they're going after 1000 accounts, unable to build a relationship with anybody. That business is a crazy thing. Or, you know, I'm holding in my iPhone here, because this thing at the end of the day will have over 100 people trying to approach me on LinkedIn with a message that says, somehow they're going to turn my life into Shangri-La. They said the exact same words to another 500 people this week, right? Do you really believe that that's going to garner your business?

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Mark Drager: The amazing thing, though, is also if you narrow your focus and you narrow your targets, and you spend more time pouring into them, it just eliminates the competition, because you're not competing for everyone's attention all the time. You are literally going in, and you are creating, I guess, a connection that can't have any competition if you know what I mean.

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Jack Daly: I'll take it to another level, Mark. I have a client in South Florida, and he has salespeople all over the nation. Their goal is to get a desk in the clients' offices.

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Mark Drager: I do that all the time, not with a desk, but anytime I have a conversation with someone, I would offer to drive down and meet with them in person simply so I could walk the halls. Because going from the elevator to reception to the meeting room, I would often pass the same people, and I would get to know them. Yeah. And then suddenly now it's like, it's like you're walking into high school, you're like, "Hey, how's it going," and you're like, you can have so many conversations between reception and the boardroom if you start to know people.

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Jack Daly: When this client gets a salesperson with a desk, they need to size into companies, they need a badge to get into the building. So they wear their badge. And so all of a sudden, the people forget that they're an outside force, that they're just coming by the desk to order some more stuff. And so these guys sit at the desk one day a week, in their top five clients, that's where they operate from. And most of the time, they're working on other business with other clients sitting at that desk. Now the other competitors are trying to get through the gatekeeper and the receptionist up there, and they're gone. You might as well just poke your head out of your desk and go, "Yeah," and make funny faces at the guy at reception who's struggling to get in.

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Mark Drager: Yeah, you know what you just reminded me of? When I started my career right out of school, I actually spent almost a year as an embedded sales rep in a hotel. So I worked for an AV company, the AV company had a contract with a hotel, I had a desk, I had a phone, I worked for the AV company, but I spent all day every day embedded in that hotel, helping the hotel, helping their clients. And I never even saw or even spoke to anyone at head office. It was like I basically worked for Novotel as opposed to working, you know, for this other company.

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Jack Daly: Why did we forget those things?

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Mark Drager: I don't know. Yeah. So let me ask you this. I just had this thought a few weeks ago, back when I started my agency in 2006. And kind of over the next 5-10 years, let's say, I used to sell in this really old school way, what I imagined as this old school European approach. So imagine if you were a little kid, and you had a pocketful of change. You go into the local deli or corner shop, and there's this lovely gentleman or woman there. You pull out your money and say, "I want to buy this chocolate bar and I want to buy this or that." They would look at your money and see that you kind of don't have enough. But they would say, "Let me see what I can do. Let me take care of you." They might help you out, or they might say, "No, you can have this, but you can't have that." But it would be that feeling of like, old-school mechanics. I feel like they used to be this way: you'd come with a problem, they would take you in and say, "Let me see what I can do to send you on your way safely." And I've just been reflecting on the fact that for maybe 10 or 12 years, I think I sold that way. People would come to us with a problem or a challenge, and I would say, "Let me see what I can do." And I would look at it, and I would send them on their way, giving them the very best that we could with what they had to work with, better than anyone else. And I was really proud of it. And then, somewhere in the last five or seven years, I focused on numbers and results, and like all of these hard things of these hard numbers, this hard data, this objective approach. And I lost this old school, "Let me take care of you and send you on your way." And I've been reflecting on this because the old way that I used to do it, frankly, got better results. And I had more fun, and everyone liked it. But it felt like it was cheating, kind of. It didn't feel like it was following the system and following the numbers. And I'm leaving money on the table and all that crap people talk about. Help me understand these two approaches, and is there really any right or wrong way if it works?

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Jack Daly: So my degree is in accounting, and my background is a numbers guy. I was once a CFO of a company. And margins are important, profits are important, and you can't get profit without revenues, which is sales. That's the drill. And none of it matters to me if I'm not doing right by the customer. And if I do right by the customer, then all of those things are the aftereffects. It's the wrong positioning to put those on the front. So you might get a transaction or two out of that, but you're not going to build a career. And so I'm pretty well known, Mark, around the world for this sentence: sports teams are run better than most businesses. And, you know, if I look at John Wooden, now I'm dating myself, but he was the coach at UCLA basketball, and out of 11 seasons, nine of them he won the national championship. And he's got prolific books all over the place. And he basically ran everything the same way. He just said, "We're going to work on the basics. We're going to practice more than anybody else out there. And we're going to play by the playbook that we designed for each game. We're going to practice those plays. And if we practice the fundamentals and show up at each game, the scoreboard will take care of itself." And that's exactly where I come from, from selling. If I do the homework, build the playbook, and practice the playbook, I don't think anybody's going to be disappointed with the top line and the bottom line of the company, period. And so all I want to do when I'm in the field with a salesperson, and I'm their coach, is to see if they're operating that way. My largest sales force, Mark, was 2,600 salespeople. And when I would visit over 100 locations, I'd have a similar message wherever I went: "There aren't 2,600 best ways to sell this stuff. What do you say we figure out the best way, build a system and process, practice the system and process, and I bet you we win more than we lose. End of story." And so when I'm out with the very best salespeople, they're canned. And what I mean by canned is not phony. They say the same thing the same way each time they encounter a certain situation.

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When somebody says, "I'm already happy doing business with a competitor," there's no hesitancy, it's full confidence. And they just lock and load. And they're ready to go. Because they've heard it so many times. Why are you going to make up something new each time you hear it? And so they're pros, and it comes across as so professional. And so it's all about preparation. I talked about it earlier with you. Go to the websites, do your homework, and have your questions ready before you get to the prospect. Really listen and not think about what you're going to ask next. And that's all preparation. Now I'm talking about them figuring out best practices and putting them into a playbook and practicing the playbook. Look, I've done these virtual sales trainings for four hours where people can buy a seat for four hours. And a couple of weeks ago, I had five salespeople from the same company. I said, "Take yourself off mute. And I want you to answer this question: Why should I do business with your company?" And each guy, here's what their answers were: experienced, knowledgeable, competitive, wide array of choice, good customer service. So those were the five answers. And I'm going, "Wait a second, if I had a competitor of yours in here, and I asked them, wouldn't they tell me the same thing?" And if you don't know why we should buy from you that's different and better than somebody else, how am I as the prospect supposed to know that? So every salesperson is going to hear that same order. It's going to go unsaid. And after you've left, they're going to say, "Why should I buy from that individual?" Well, on a sales call, figure out how you're better and different than everybody else. And then hit them up with that. That to me is all preparation.

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Mark Drager: Oh, this is so good. If you'd like to know more about Jack Daly, you can head over to jackdalysales.com. He has a bunch of workshops, digital workshops, there are coaching programs, there are books as he mentioned. I could just pick your brain all day. I love it so much. But unfortunately, we have to wrap things up. So, I want to hit you with this final question I have: What is your number one tip or strategy to help us sell more?

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Jack Daly: I'm a voracious reader. I'll read probably 100 books this year. And I'm going to give you my favorite book that everybody should take down: "Mindset" by Carol Dweck. And that puts us either into a growth mindset or a fixed mindset. And if you're in a fixed mindset, by the way, we're not born that way, we get to choose, and you can choose that anytime at any age. But here's what I will tell you, you can read all the sales books you want in your life, if you're a fixed mindset person, you ain't going to be successful.

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Mark Drager: I used to be the mayor of Fixed Mindset City; like, I ran for governor of it. And I still struggle with it often. Fixed mindset and scarcity mindset are two things that I still bump up against.

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Jack Daly: You know, I was in the mortgage business years ago, and I'm watching the mortgage industry right now. And 15 months ago, the interest rates were about 3% on a 30-year fixed-rate mortgage, and now they're at about seven. And the salespeople are going, "Well, I gotta go find a new profession, because nobody's going to do a loan at seven." Well, wait a second.

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Mark Drager: That's not true, though. Because just last month, because there was a drop in rates, I think there was an uptick in the number of mortgages being written.

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Jack Daly: Yeah, yeah. Because people are like, "Oh, they're going down again. I'll take loans." I took loans at 17 and a half percent. Like, it's just a mindset error. Hey, every time you're confronted with a challenge, like the pandemic, by the way, as a professional speaker, I traveled hundreds to thousands of miles to speak to large groups of people. The pandemic, I'm in lockdown. Well, most people would say, "Well, then your career and your business are shot." I built a virtual studio, and I doubled my revenue and profits during the pandemic. And I didn't have to get on an airplane or stay at a hotel. It's a mindset, right? And so, whenever you're confronted with the economy being wrapped, or interest rates, whatever the issue is, some supply chain issues, ask yourself: "How can I make this a win for me? Is there a win here? And where is the route to the win?" Because the majority of people are going to close their laptops and go spend their time at the gym or something because they can't sell. I'm going to use that as my opportunity to go right by the majority of them. And when whatever catastrophe is over and they come back in, I will be the premier leader. Growth mindset.

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Resources & Go Deeper

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"A Brief History of Modern Sales Methodologies for Sales Leaders"

The article dives  into the history of salesmanship, starting from manipulative techniques to modern-day approaches that focus on customer needs and trust-building​.

A brief history of modern sales methodologies for sales leaders (membrain.com)

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“6 Sales Fundamentals: The Dos & Don’ts in Winning More Deals”

Korn Ferry's article discusses six fundamental data points of selling that impact the dos and don’ts in the sales process. It highlights the importance of efficient use of selling time, engaging key decision-makers, providing insights to clients, and the significance of questioning skills in establishing customer needs​. 

6 sales fundamentals: The dos & don’ts in winning more deals (kornferry.com)

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“The Evolution of Sales Techniques: A Comprehensive Journey Through Time”

This article from Rizologic traces the history of sales techniques from the early 1900s to the 2010s. It discusses various sales approaches like trust-based selling, scientific selling, mood selling, and consultative selling. The article also covers the rise of relationship selling and solutions selling in the latter part of the 20th century.

The Evolution of Sales Techniques: A Comprehensive Journey Through Time | Rizologic

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“How Important Are "Techniques" To Sales?”

This blog post on Partners in EXCELLENCE explores the role of techniques in sales. It emphasizes the importance of establishing trust and building business relationships as key to successful sales, rather than relying solely on sales techniques. The post also discusses the potential drawbacks of manipulative sales techniques and the value of authentic customer engagement​.

How Important Are "Techniques" To Sales? - Partners in EXCELLENCE (partnersinexcellenceblog.com)

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