April 15, 2025 • 32 mins
In this episode, Rob chats with Jack Daly, legendary sales trainer, entrepreneur, author, and endurance athlete. They dive into how business owners can build a culture by design, not by default, no matter if their teams are in-office or remote. Jack shares proven strategies for creating an environment where people want to work, why playbooks are critical across the organization (not just in sales), and the three high-impact changes that help businesses scale effectively. Packed with real-world stories and Jack’s signature energy, this is a must-listen for any business owner serious about growth, alignment, and culture.
Key Takeaway:
A thriving company culture doesn’t happen by accident. Business owners must proactively design their culture, invest in clear communication, and build systems that scale—like playbooks, recognition programs, and robust financial plans. Whether you’re just starting or running a company for 15 years, it’s never too late to realign your business for greater impact.
Questions I ask Jack Daly:
03:15 What should leaders focus on to make Culture by Design intentional rather than just letting it happen?
06:32 Where do you start to start to turn around that culture and make it more intentional?
10:11 What are some considerations that you should make to accommodate and to engage your people who are not in the office?
15:48 Company playbooks are very effective. How should business owners be thinking about playbooks throughout their organizations?
18:22 What are your thoughts about having playbooks in other parts of the organization?
22:14 What are the top three things your coaching clients do that make the biggest impact?
26:37 When we talk about a financial plan, are this KPIs, a full budget, or both revenue and expense projections?
27:00 When it comes to the products, is it just revenue that you're looking at or are there some other things to look at from time to time?
More About Jack:
Check out Jack Daly Sales
Looking for a good read? Explore Jack’s books here
Connect with Jack on LinkedIn.
More About Rob Levin & WorkBetterNow:
Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on LinkedIn.
Visit WorkBetterNow.com
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Jack Daly (00:00):
By design is suggesting proactivity, scheduling these means of communication, and holding to the schedule. And what happens is that people and companies tend to underperform to their capabilities because we rushed to the urgent at the expense of the important; and communication, there's nothing urgent about it, so what happens is it gets kicked down the ladder. This podcast was on my calendar to do, it was on your calendar to do, but if we didn't put it on the calendar, I can tell you, you and I both have a lot of other urgent things to get to, but we're not going to cancel it. So it took place and the urgent will get taken care of later.
(00:01):
Welcome to the Great Talent Great Business podcast, your go-to resource for building exceptional teams and thriving businesses. Each episode delivers actionable insights on harnessing offshore talent, integrating innovative technology, cultivating a vibrant company culture, and attracting and retaining top performers.
Jack is a dynamic speaker accomplished athlete. He has completed close to a hundred marathons, I believe, and at least five Ironmans across several continents.
Let's jump right in. Jack, I wanna start with Culture by Design, which is a term I heard from you many years ago. When you're building a company culture, when you're building a company, what should leaders focus on to make it intentional rather than just letting it happen?
And it comes down to really three things when I think about Branson; vision, really understanding what it is you're trying to build, you can't get there unless you know what there is. Yeah. Then, bringing in key people in key spots. And then the third thing is what you just mentioned, which is an intentionally designed culture. Creating an environment in your company where people want to actually go to work there.
what are you doing to instill that type of an environment in your company? And, I really come down to four legs of a strong culture (00:05):
recognition systems, people are starving for it. Communication systems, people really wanna know what's going on, give me the real skinny and how are we doing and where are we headed? Regular, ongoing, proactive communication. Third, personal and professional development processes, why should I come to work at your company and why should I stay once I'm there? What's in it for me? How are you developing me? And one of the things I wanna underscore there, Rob, is I said personal and professional.
Rob Levin (00:06):
Jack, that's awesome. I'm nodding my head because these are many of the things I talk about, and of course, I'm like, oh, I wonder where I heard these things from; it was probably from seeing you probably 20 years ago, and eventually, I was able to make it come to fruition now with WorkBetterNow.
Jack Daly (00:07):
How do you eat an elephant? One bite at a time. I think some easy things, are recognition. I can't help but remember having a sales team of 2,600 salespeople; that's a mega number for most of our listeners here; but 2,600 people operating out of a hundred different locations actually got a personalized birthday card sent to their home from me, and they also got an anniversary card. When they were, you know, three years with a company, eight years with a company, or whatever number it is sent to their home so that they could share it with their significant other and their kids and so forth.
But HR has the birthday of everybody, and they've got the start date of everybody, so I just said on the 15th of every month, have the cards for next month al ready for me to sign and make notes in; and I'd hand them back to HR and say, spread them out into the mail on the appropriate days so they get it on their birthday.
Rob Levin (00:09):
That's something that everybody can do; it's simple, it is a little bit of work. It's fun because as you mentioned there, there's something about giving something to people, right? Yeah. It's a very cathartic thing. It's just a no-brainer. And we'll also share in the show notes a little bit of information on the W Awards, at WorkBetterNow, our recognition system, which is also very easy to do, a great place to start.
Jack when it comes to, you know, so many companies now have remote people or hybrid, and which brings a lot of opportunities and obviously some challenges when it comes to building a culture by design.
I'll take you back over 30 years ago. I would rent an hour time at KOCE-TV in Orange County, California, and I'd go down to the studio and I would speak for an hour; sometimes I'd have guests, the Head of Sales or the Head of Operations and interview them and always giving them an idea of how we're performing financially and where we're headed towards the vision.
And then when I would make an occasional visit to someplace and see somebody, they'd come up and say, I just love who you are as a human because you do these videos and you know, you make mistakes and you just shrug 'em off and you're just interested in making us feel good about the company that we're a part of, right. A newsletter today, we can leverage technology and do it such that you don't have to send it to a printer; back in those days, I had to do this newsletter and then send it to a printer and then send a hard copy out and all of those types of things. It's so much easier to do today, but here's what I would challenge people on, in terms of the newsletter. The newsletters are very often done by HR and they tend to be policy and procedure and dull types of things, what I want it to be is like a family photo album, I want it to be fun, exciting stuff, things that'll make you laugh, throw some information in there, give some recognition in there, and so, I had a company that I grew from, four people to 750 people, and in that first three years, we did that.
In that period of time, our newsletter, grew from one page to over 50 pages and it was monthly. And I personally, as the CEO, took a day every month and wrote it from one to 50 pages. That was the level of importance communication had with our remote people.
Yeah. So the takeaway for the audience, I'm gonna put use my own words here, is over communicate, right? Because it's more than you're probably used to doing when everybody's by the water cooler and, spoiler alert, you don't have to rent the studio, you can do this now, obviously from your desktop, there's editing tools if you even have to do that, and I love the whole thing, you didn't use this word, I'll use the word, just be authentic, just be yourself. And that, that builds trust, and Maybe we'll touch on trust, I know that's a big one with you in a little bit.
This episode is brought to you by Work Better Now, your trusted partner for getting high performing talent from Latin America. Our clients tell us that partnering with Work Better now has transformed their businesses by providing the proactive, reliable, and skilled professionals that they need to thrive.
Jack Daly (00:16):
So you've heard this for two decades. Sports teams are run better than most businesses, and that should bother you if you're a business owner. How are sports teams run better than most businesses? I've got three things; one, they've got a playbook, that doesn't matter, high school, college, professional, they got a playbook.
I'm gonna take you back to my 2,600 salespeople because if I magnify this, it brings home the point really well. Can you imagine? Can you imagine 2,600 salespeople in the field selling 2,600 different ways? I brought them all together and said, that would be insane, there's probably a best way to sell this product or service.
So, the playbook is what are the best ways. if we look objections, salespeople's, knees knock on objections; I happen to be thrilled with objections because there's signs that somebody's interested maybe doing business with me, right. And so I wanna get them over their objections, but I don't need to wing it because I can anticipate what they're gonna be, just like a sports team can anticipate what they're going to do when I go back to throw a pass, or make a run, right? So, what are the common objections? There's probably less than a dozen, so why not figure out what the best responses would be, and then drill it into us such that we're comfortable; and by the way, the more comfortable we're getting with understanding that the objections are gonna come and we have the answers, the less our needs are knocking. Yeah. Which means that we're conveying confidence in our company product and service, which is giving comfort to the prospect.
I'll challenge the listener today to say, how quickly is your financial area closing the books? How quickly are you turning around and getting financial statements that tell you how you did, and what the key performance indicators are? So that we can change behavior quick enough to make a difference the following month.
Same thing applies on the operations side of the house, same thing applies in the plant. Just imagine Amazon, where I put an order in yesterday at about four o'clock in the afternoon, I ordered something that had to do with my energy shakes that I take, and I ran out of protein powder and I put my order in, and it'll be delivered today between 4:00 and 8:00 p.m.
And so for example, I'm a Philly guy born and raised, and so I like a good hoagie, a good sub. Jersey Mike's works for me, and no matter where I go, Jersey Mike's is delivering me the sandwich that I want. The one that I get at my local jersey Mike's, is the same one everywhere, and the store has got three to five people typically in their twenties delivering that product exactly the way I want it, no matter where I am. That's because franchises are driven by a playbook, they figured out how to do this in the most effective fashion, not just sales, everything that goes on in the organization.
Rob Levin (00:22):
Right, which goes a long way. Switching gears one more time Jack, you coach a select few business owners who are fortunate to be working with you. If you were to say, looking at the group that you're currently coaching that you have coached. What are the top three things that they end up doing after or while working with you that make the biggest impact?
The successes that I've had with my companies that I built myself, as well as the ones that I've coached along the way, have been driven with a financial planning acumen, holding people to the numbers because that will give us the efficiencies and that will give us the effectiveness and that will improve our margins, and it helps us make this better decisions.
I took on a coach client in Houston, who had been in business for 14 years, and before I start my engagements with my coach clients, I tell them, send me anything that's not bolted down so I can understand your company better. And I give them examples. So, you know, I want the vision, I want the org chart, I want the financial plan and financial business plan, and this guy sends me a note and he says. Hey, you may fire me before we get started, I've got bad news and good news. The bad news is I don't have anything that you're asking me for; the good news is it won't take you long to review it. So he had a sense of humor and we brought his management team out to my house for a couple days and we built this financial plan.
You've met my wife Karen, who recently sold her business, but she had it for over 30 years and it was a $70 million business that she owned exotic fruits and vegetables. And at one stage, their claim to fame was we've got over 200 different fruits and vegetables that are unique to the world that we offer.
So the product offerings is slimming down the line, and then the third thing that I would tell you is too many organizations call in too many customers and would be better served by having better customers and less. And when I work with my clients and ask them to give me their current list of customers ranked by revenue, there's a significant drop off very quickly; and then I look at the amount of work that the operations and salespeople are putting in on accounts that don't merit it, and if we could take their time and shift it to accounts that are similar to the top, that's where we're really jet propulsion, the growth of the company.
As an owner. Yeah. Got it. And then, when it comes to the products, is it just revenue that you're looking at when you're trying to figure out what are the best products or are there some other things to look at from time to time?
Jack Daly (00:28):
Hey Rob, let me go back to that Houston client that I talked about with set six consecutive record months, and the six months were better than any one year full revenue and profit that they had over a thousand customers.
And he guessed about a hundred. And I said, well, but your salespeople are spending 90% of their time on one in $2,000 accounts. You'll get that business, even if you don't call on those customers, you're not their main provider, they're doing business with somebody else, and they only use you in an emergency, so you're gonna get that business anyway, we don't need to call on them anymore. Call on these giants, you're gonna get a lot of rejection, it's gonna take you longer to win them over, but when you win them, now you've got two, three, $400,000 accounts. So you know, all of a sudden, instead of having 10 of those, all of a sudden you've got 30 of those.
jackdalysales.com, that's the easiest way, and Daly is D A L Y no, I, no E. And it's always a pleasure, Rob, to deal with a pro. And I do a lot of podcasts and you followed a process, you were prepared before the call, we weren't going through and winging things, although this was authentic and real, I just felt I was in the room with a professional, and so I thank you for your preparation.
And so often, particularly where you started with culture, people will say, well I don't want to put back money out for this because where's my ROI, it's too expensive; when I think about recognition awards for salespeople and, I'm famous for giving away a Mercedes to my top salesperson and people will go, well, that he's playing with a bigger purse than me.
No, no, no. When you understood what the return on that investment was and how much did it take to really do that, it wasn't a lot of money. I was getting a 60 times return on every car that I gave away at 60 x. But on first blush. I hear it so often, too expensive. And so understanding the rigor of saying, what can we measure and can we expect on this investment and holding your people to getting that return, that's the key.
By design is suggesting proactivity, scheduling these means of communication, and holding to the schedule. And what happens is that people and companies tend to underperform to their capabilities because we rushed to the urgent at the expense of the important; and communication, there's nothing urgent about it, so what happens is it gets kicked down the ladder. This podcast was on my calendar to do, it was on your calendar to do, but if we didn't put it on the calendar, I can tell you, you and I both have a lot of other urgent things to get to, but we're not going to cancel it. So it took place and the urgent will get taken care of later.
(00:01):
Welcome to the Great Talent Great Business podcast, your go-to resource for building exceptional teams and thriving businesses. Each episode delivers actionable insights on harnessing offshore talent, integrating innovative technology, cultivating a vibrant company culture, and attracting and retaining top performers.
Jack is a dynamic speaker accomplished athlete. He has completed close to a hundred marathons, I believe, and at least five Ironmans across several continents.
Let's jump right in. Jack, I wanna start with Culture by Design, which is a term I heard from you many years ago. When you're building a company culture, when you're building a company, what should leaders focus on to make it intentional rather than just letting it happen?
And it comes down to really three things when I think about Branson; vision, really understanding what it is you're trying to build, you can't get there unless you know what there is. Yeah. Then, bringing in key people in key spots. And then the third thing is what you just mentioned, which is an intentionally designed culture. Creating an environment in your company where people want to actually go to work there.
what are you doing to instill that type of an environment in your company? And, I really come down to four legs of a strong culture (00:05):
recognition systems, people are starving for it. Communication systems, people really wanna know what's going on, give me the real skinny and how are we doing and where are we headed? Regular, ongoing, proactive communication. Third, personal and professional development processes, why should I come to work at your company and why should I stay once I'm there? What's in it for me? How are you developing me? And one of the things I wanna underscore there, Rob, is I said personal and professional.
Rob Levin (00:06):
Jack, that's awesome. I'm nodding my head because these are many of the things I talk about, and of course, I'm like, oh, I wonder where I heard these things from; it was probably from seeing you probably 20 years ago, and eventually, I was able to make it come to fruition now with WorkBetterNow.
Jack Daly (00:07):
How do you eat an elephant? One bite at a time. I think some easy things, are recognition. I can't help but remember having a sales team of 2,600 salespeople; that's a mega number for most of our listeners here; but 2,600 people operating out of a hundred different locations actually got a personalized birthday card sent to their home from me, and they also got an anniversary card. When they were, you know, three years with a company, eight years with a company, or whatever number it is sent to their home so that they could share it with their significant other and their kids and so forth.
But HR has the birthday of everybody, and they've got the start date of everybody, so I just said on the 15th of every month, have the cards for next month al ready for me to sign and make notes in; and I'd hand them back to HR and say, spread them out into the mail on the appropriate days so they get it on their birthday.
Rob Levin (00:09):
That's something that everybody can do; it's simple, it is a little bit of work. It's fun because as you mentioned there, there's something about giving something to people, right? Yeah. It's a very cathartic thing. It's just a no-brainer. And we'll also share in the show notes a little bit of information on the W Awards, at WorkBetterNow, our recognition system, which is also very easy to do, a great place to start.
Jack when it comes to, you know, so many companies now have remote people or hybrid, and which brings a lot of opportunities and obviously some challenges when it comes to building a culture by design.
I'll take you back over 30 years ago. I would rent an hour time at KOCE-TV in Orange County, California, and I'd go down to the studio and I would speak for an hour; sometimes I'd have guests, the Head of Sales or the Head of Operations and interview them and always giving them an idea of how we're performing financially and where we're headed towards the vision.
And then when I would make an occasional visit to someplace and see somebody, they'd come up and say, I just love who you are as a human because you do these videos and you know, you make mistakes and you just shrug 'em off and you're just interested in making us feel good about the company that we're a part of, right. A newsletter today, we can leverage technology and do it such that you don't have to send it to a printer; back in those days, I had to do this newsletter and then send it to a printer and then send a hard copy out and all of those types of things. It's so much easier to do today, but here's what I would challenge people on, in terms of the newsletter. The newsletters are very often done by HR and they tend to be policy and procedure and dull types of things, what I want it to be is like a family photo album, I want it to be fun, exciting stuff, things that'll make you laugh, throw some information in there, give some recognition in there, and so, I had a company that I grew from, four people to 750 people, and in that first three years, we did that.
In that period of time, our newsletter, grew from one page to over 50 pages and it was monthly. And I personally, as the CEO, took a day every month and wrote it from one to 50 pages. That was the level of importance communication had with our remote people.
Yeah. So the takeaway for the audience, I'm gonna put use my own words here, is over communicate, right? Because it's more than you're probably used to doing when everybody's by the water cooler and, spoiler alert, you don't have to rent the studio, you can do this now, obviously from your desktop, there's editing tools if you even have to do that, and I love the whole thing, you didn't use this word, I'll use the word, just be authentic, just be yourself. And that, that builds trust, and Maybe we'll touch on trust, I know that's a big one with you in a little bit.
This episode is brought to you by Work Better Now, your trusted partner for getting high performing talent from Latin America. Our clients tell us that partnering with Work Better now has transformed their businesses by providing the proactive, reliable, and skilled professionals that they need to thrive.
Jack Daly (00:16):
So you've heard this for two decades. Sports teams are run better than most businesses, and that should bother you if you're a business owner. How are sports teams run better than most businesses? I've got three things; one, they've got a playbook, that doesn't matter, high school, college, professional, they got a playbook.
I'm gonna take you back to my 2,600 salespeople because if I magnify this, it brings home the point really well. Can you imagine? Can you imagine 2,600 salespeople in the field selling 2,600 different ways? I brought them all together and said, that would be insane, there's probably a best way to sell this product or service.
So, the playbook is what are the best ways. if we look objections, salespeople's, knees knock on objections; I happen to be thrilled with objections because there's signs that somebody's interested maybe doing business with me, right. And so I wanna get them over their objections, but I don't need to wing it because I can anticipate what they're gonna be, just like a sports team can anticipate what they're going to do when I go back to throw a pass, or make a run, right? So, what are the common objections? There's probably less than a dozen, so why not figure out what the best responses would be, and then drill it into us such that we're comfortable; and by the way, the more comfortable we're getting with understanding that the objections are gonna come and we have the answers, the less our needs are knocking. Yeah. Which means that we're conveying confidence in our company product and service, which is giving comfort to the prospect.
I'll challenge the listener today to say, how quickly is your financial area closing the books? How quickly are you turning around and getting financial statements that tell you how you did, and what the key performance indicators are? So that we can change behavior quick enough to make a difference the following month.
Same thing applies on the operations side of the house, same thing applies in the plant. Just imagine Amazon, where I put an order in yesterday at about four o'clock in the afternoon, I ordered something that had to do with my energy shakes that I take, and I ran out of protein powder and I put my order in, and it'll be delivered today between 4:00 and 8:00 p.m.
And so for example, I'm a Philly guy born and raised, and so I like a good hoagie, a good sub. Jersey Mike's works for me, and no matter where I go, Jersey Mike's is delivering me the sandwich that I want. The one that I get at my local jersey Mike's, is the same one everywhere, and the store has got three to five people typically in their twenties delivering that product exactly the way I want it, no matter where I am. That's because franchises are driven by a playbook, they figured out how to do this in the most effective fashion, not just sales, everything that goes on in the organization.
Rob Levin (00:22):
Right, which goes a long way. Switching gears one more time Jack, you coach a select few business owners who are fortunate to be working with you. If you were to say, looking at the group that you're currently coaching that you have coached. What are the top three things that they end up doing after or while working with you that make the biggest impact?
The successes that I've had with my companies that I built myself, as well as the ones that I've coached along the way, have been driven with a financial planning acumen, holding people to the numbers because that will give us the efficiencies and that will give us the effectiveness and that will improve our margins, and it helps us make this better decisions.
I took on a coach client in Houston, who had been in business for 14 years, and before I start my engagements with my coach clients, I tell them, send me anything that's not bolted down so I can understand your company better. And I give them examples. So, you know, I want the vision, I want the org chart, I want the financial plan and financial business plan, and this guy sends me a note and he says. Hey, you may fire me before we get started, I've got bad news and good news. The bad news is I don't have anything that you're asking me for; the good news is it won't take you long to review it. So he had a sense of humor and we brought his management team out to my house for a couple days and we built this financial plan.
You've met my wife Karen, who recently sold her business, but she had it for over 30 years and it was a $70 million business that she owned exotic fruits and vegetables. And at one stage, their claim to fame was we've got over 200 different fruits and vegetables that are unique to the world that we offer.
So the product offerings is slimming down the line, and then the third thing that I would tell you is too many organizations call in too many customers and would be better served by having better customers and less. And when I work with my clients and ask them to give me their current list of customers ranked by revenue, there's a significant drop off very quickly; and then I look at the amount of work that the operations and salespeople are putting in on accounts that don't merit it, and if we could take their time and shift it to accounts that are similar to the top, that's where we're really jet propulsion, the growth of the company.
As an owner. Yeah. Got it. And then, when it comes to the products, is it just revenue that you're looking at when you're trying to figure out what are the best products or are there some other things to look at from time to time?
Jack Daly (00:28):
Hey Rob, let me go back to that Houston client that I talked about with set six consecutive record months, and the six months were better than any one year full revenue and profit that they had over a thousand customers.
And he guessed about a hundred. And I said, well, but your salespeople are spending 90% of their time on one in $2,000 accounts. You'll get that business, even if you don't call on those customers, you're not their main provider, they're doing business with somebody else, and they only use you in an emergency, so you're gonna get that business anyway, we don't need to call on them anymore. Call on these giants, you're gonna get a lot of rejection, it's gonna take you longer to win them over, but when you win them, now you've got two, three, $400,000 accounts. So you know, all of a sudden, instead of having 10 of those, all of a sudden you've got 30 of those.
jackdalysales.com, that's the easiest way, and Daly is D A L Y no, I, no E. And it's always a pleasure, Rob, to deal with a pro. And I do a lot of podcasts and you followed a process, you were prepared before the call, we weren't going through and winging things, although this was authentic and real, I just felt I was in the room with a professional, and so I thank you for your preparation.
And so often, particularly where you started with culture, people will say, well I don't want to put back money out for this because where's my ROI, it's too expensive; when I think about recognition awards for salespeople and, I'm famous for giving away a Mercedes to my top salesperson and people will go, well, that he's playing with a bigger purse than me.
No, no, no. When you understood what the return on that investment was and how much did it take to really do that, it wasn't a lot of money. I was getting a 60 times return on every car that I gave away at 60 x. But on first blush. I hear it so often, too expensive. And so understanding the rigor of saying, what can we measure and can we expect on this investment and holding your people to getting that return, that's the key.
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