062: Jack Daly - What Goes Behind a Great Sales Playbook?
28 Jan 2026 · 32 min
Jack Daly breaks down what makes a sales playbook work: systems, goal-setting, pipeline management, role-play practice, and accountability. He walks through how to scale a sales team and shares a client growth story that shows these principles in action.
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Bill, by the time you were giving my background, I ended up getting tired just thinking about all those things. Glad to be here.
It is. But you raised the bar for all of us. Thank you for leading the way.
You bet.
Now you're in Southern California today.
Yeah, absolutely. I'm home. I haven't been home for 17 days, so it's a joy.
Yeah. Well, you and I see each other across Facebook and the other social media in different parts of the world on a frequent basis. So it's nice to be talking before we get into how we developed the sales playbook. Talk to us about how you get into this whole line of work and tell us some of your background.
Yeah. Between the ages of 26 and 46 years old, I took a blank sheet of paper. I sketched a business out on it. I had my vision of what I wanted to build. I sold that vision to other people to join me in building the companies. All six companies became nationwide, sold a couple of Wall Street. They're all fast growing at the top and bottom line. And to give you an example, I moved to California from the east coast to just enjoy the weather. I started the company with four people. 18 months later, all organic growth. We went to 750 people. And in our first three years, we made $42 million in earnings. However, at the age of 46, I got burnt out, and I didn't enjoy getting up and working with my salespeople and the rest of the organization. So I pulled the pin and I early retired. But I'm not a retiring guy. And so at 26 years old, I played a lot of golf for a year and got bored with it. And then I did some consulting, which was a lot of work for too little money. And then someone asked me to keynote an annual conference of 750 people held in New Orleans. I knocked the ball out of the park, fell in love, and I've been in love ever since with the speaking business. So I'm about 100, 110 speaking engagements annually around the world.
Yeah. And you bring it every time.
You know what? We're going to talk about how important that is for salespeople to do as well.
Yeah. So tell us a little bit of take us through. I know that the sales playbook has evolved over time. Where did this show up? What's the story of where you learned how to do this and how you've honed it?
Yeah.
So.
Let'S go back to the company that went from four people to 750. I opened up the first of 22 offices. I opened up the first office in Irvine, California. And what we said is, our bhag, our big hairy, audacious goal, was we were going to be the number one mortgage company in Orange County. Now that is a BHAG. And this was back in 1985 when Jim Collins wrote his first book, Built to Last. And that's where BHAG came from. And so I just said, I'm going to drive a stake in the ground. It's going to Be really, really tall. I'm going to be the number one mortgage company in Orange County. Think about this. Bank of America was there. Countrywide Funding was there. Shearson American Express was there. Wells Fargo was there. And Jack and three of his colleagues are going to build a company and kick their own asses. But what we said was once we did that, we would then memorialize the systems and processes of what enabled us to achieve that. And then we would, we would roll that playbook out for each one of our respective offices that we built throughout the nation. So I'm educated and trained as an accountant, quite frankly, a bachelor's degree in accounting, CPA with Arthur Anderson. So systems and processes. Systems and processes are two bywords of mine that I believe very strongly in. And yet in the sales side of most companies, they don't exist. We have each guy doing his own thing, which makes no sense whatsoever to me. So that's where it emanated from.
Absolutely. Well, we see that again and again. And we around coaches and around other groups, we've got people starting and each one's got their own little secret sauce. And that doesn't help the company grow as a whole, right?
Absolutely. In fact, this is the way I used to say it. My largest Salesforce was 2,600 salespeople. And I'd visit over 100 offices with the same speech. What do you say we figure out the best way and then practice those systems and processes so that we sell at the optimal methodology consistently throughout the organization. So I'm going to give you my one liner that's painful to hear but helpful to learn from. Here it is. Sports teams are run better than most businesses. It doesn't matter what your sport is, it doesn't matter what level it is. You could be playing a sport on a field, on a court or on the ice. You could be high school, college or professional. But this much Bill, I can guarantee you there isn't a coach in any sport that would consider putting their players on the field without a playbook. But three years ago, I wrote a best seller called Hyper Sales Growth. And people called me from all over the world and said, I want to engage you to help me, take me to the next level. And I said, perfect. The best way to get this underway is send me your sales playbook and I'll build you the next level up. 98 out of 100 companies could not provide me with a sales playbook, which de facto means that each person is making it up on his own.
Yep, I think there are a Lot of look, we could look at sports teams, we could look at military units, we could look at a lot of places and you could say, yes, they train for and they tease out all the common scenarios. They train for the worst case and they drill, drill, drill, and they run their playbook again and again and they update it when something changes or whatever. Right. But there's some thinking and organizing and sharing of wisdom across that we don't see all the time. And you see it also with something like the huddle. People are like, oh, I don't want to huddle. That huddle's a nuisance. I'm like, okay, what's the biggest problem around here? Well, we are all in silos.
Right? Right. Right. Well, how about this, let's go back to the sports. There isn't a coach in any sport that we consider putting their players on the field without proper preparation, training and practice. But when I go into organizations and ask, where are the salespeople practicing? There's, there is a debt, there is dead silence. And then I ask it again, where are the salespeople practicing? And then somebody coughs it up and says, you want, you want to give the answer? Go ahead, Bill, you got it. Where are they practicing?
With customers, right?
Yeah, I'm practicing on real deals. I'm practicing on prospects and customers. Who, who in the right mind in sports would put up with a team on the field and say, well, the only time we practice is when we have a game. It's insanity. We're practicing on real opportunities. Practice inside to get better outside. That's the key.
Yeah, absolutely. So why don't you. Actually, I didn't check this, but do you have an example? Can you tell us a story about a company where they didn't have one and they've gone ahead and applied and developed and applied a sales playbook?
Yeah, I could give you. We go way beyond the time of this podcast with examples. Let me give you my most recent, a great example. Last month's Forbes magazine there was a feature article on the 75 self made women in America ranked by net worth. My client was number 39 when I met her. Her company was 19 years ago, 4 million in annual sales with seven salespeople. Today, she's five spots ahead of Barbra Streisand in net worth. Her Co. Is 700 million in annual sales and is a cash machine and is being driven by over 400 salespeople. The way we got her there was building a playbook and teaching and practicing her salespeople on The Playbook.
That's a powerful, powerful story, right? 4 to 700 million. And propelling her to that success, I think is something that everybody's jealous of, right?
Absolutely. Listen, I'm a marathon runner, and she knows that. Two years ago, she said, are you coming in to run New York Marathon? I said, I am. She said, do you have time for me for lunch? And I said, sure. We decided on where and when. I showed up at the restaurant before she got there, and she walked in with my book, Hyper Sales Growth. She put it down on the table where we're going to eat, and. And we hugged each other and then sat down and I just said, what's up with the book? What are you bringing the book for? And she said, oh, I was just hopeful that you're gonna autograph it for me. I'm like, you want me to autograph your book? I mean, you're five spots ahead of Barbara Streisand, for God's sake. And she goes, yeah, but I read this book and I started crying when I finished it because I realized we built our entire company based on what's in this book. It's just the book didn't exist at the time. You were just giving it to us verbally. How cool is that? And that is all basic fundamentals. The blocking and tackling in a playbook of what a salesperson needs to do. Now, let me give you another warning, though, in your listeners. We have helped companies build their playbook, brought it into the company, and heard this by the salespeople. Well, you know, I've been selling for eight years. I have my own style, right? And they're resisting the systems and processes. Well, Well, I can't. Can you imagine? Can you imagine Nick Saban at the university Alabama, who's won four out of the last seven years, the national college football championship, and is the highest paid coach in all of College Sports at $11 million a year. Could you imagine him taking that crap from a high school American that he recruited? Well, coach, I'm a high school American. Been playing since I was pee wee. I've got my own style. There's no way that that would be accepted by any coach in any sport. But I'm telling you, Bill, that is accepted in so many businesses by the sales manager and the leadership of a company. And a lot of times that crap comes out of the mouth of top salespeople as if they have figured it all out.
Yeah, yeah, yeah, yeah. Well, I remember a guy that I was on the advisory board for years ago. And he was having a whole crisis around. He'd brought in this hotshot salesperson who just was rubbing everyone the wrong way. He's like, I don't know why this is bothering me and why. I'm like, oh, I can tell you why. Look at your values. Your values are all around the team. Look at your whole focus. It's around teamwork and team playing and. And you bought this like strutting rock star of a guy who's running all over everything thinking he's God's gift. And that doesn't fit your approach. And it's just like that. I've got my own style kind of thing. I'm going to do my own thing over here.
And I'll give you the name of the guy in sports that everybody pretty much knows that fits that definition. T. Oh. Terrell Owens. And TO Was a high skilled player in his position, but went to three teams and ruined every one of them with his own style type of approach to the business and then went on to Canada and ruined the team up there before nobody wanted them. Right?
Yeah. When you watch teams play well together, this goes to the, the people practices of having great people who fit your culture and work well together as well. But let's go back to the Playbook. Talk to us about how to develop this Playbook. What are the first steps people need to take to before they've gone and read your books and give them the meat?
Yeah. So I can't help, and I don't want this to be a commercial, but I can't help but tell you that I've had that question asked so many times that I went back and, and wrote a textbook called the Sales Playbook for Hyper Sales Growth. We also put in a free app in it where you can download all of the forms and the processes. It's a. It's like this. It's like Vern Harnish is scaling up for salespeople and sales managers. And so what I would say is that that's the methodology.
Now.
The key in the Playbook is you. One, you don't build it for your salespeople. You build it with your salespeople. It is a document that is going to plow into it the best practices of the team and then enrich it with some of the things that they haven't come up with that you might know by virtue of your experiences or your reading or your modeling. The masters of other companies. But there are component parts of the Playbook that are consistent from company to company, regardless of the industry. For example, every salesperson needs to have their goals in writing with an identification of the high payoff activities that need to take place in order to get those goals accomplished. And they need to be measured because things that get measured, get done. And then lastly, accountability process where we're holding the salespeople to what they said they were going to do. That is one portion of a playbook. A second portion of a playbook is proactive pipeline management. And proactive pipeline management is identifying your basket of prospects in a level and in order of importance and, and then a methodology of staying regularly in touch with them to convert them to customers. We then take the process of customers and rank them and also have a touch system with them, converting them to clients, which clients are different than customers. Clients are regular, ongoing, doing a lot of business with us, whereas a customer is just occasionally doing business with us. The rigorous, the rigor of having those buckets and those buckets prioritized. And then again, someone holding us accountable on a regular, ongoing schedule basis is critical in terms of being a part of the playbook. Now I'm starting to build Bill, some themes here and some of those themes are things that get measured, get done. And another theme is accountability. I am convinced that the resistance of salespeople to a playbook is they don't want to be measured and then held accountable. That's the, that's the breakdown.
Yeah, I see that a lot in a lot of teams, at all levels, not just in sales. Right. People. Accountability gets uncomfortable. And in particular, I think accountability gets uncomfortable because of the morality. They feel bad if they've missed something rather than being curious or interested in how they miss something that they fully intended to do at the moment they said they were going to do it. So we lay out things, we set goals, we do whatever we fully intend them. Except for a few small number of us that are deeply flawed sociopath. But mostly we intend to do it and then we go about doing it and then we get very uncomfortable because we didn't do what we said. But we get into that good, bad, right, wrong. Instead of, huh, I wonder why, what happened at that moment that I didn't do it? Like, you know, where did that go, that forensic examination that's free of morality and full of curiosity.
Yeah, look, particularly in the sales side of the house. 50% or more of selling success has nothing to do with the playbook. 50% or more of selling success has nothing to do with product price, service strategies, tactics. 50% or more of success has to do with the attitude, the six inches between the salesperson's ears. Now, the challenge and the resistance of a salesperson to being held accountable is if you call them out on their shortcomings, they're trying to protect their ego and their positivity in their head. And. And that ego gets in the way of their ability to digest and look for ways that I can take this pointer and enhance my effectiveness in the field and thereby increase my success and my income.
Absolutely. So we did a subset of this recently of your work with our accelerator programs. And I have been leading three accelerator programs and I change up cities from time to time. But we take very early stage companies now. We regulate coaching clients are averaging a little over $60 million and they're hundreds of people. I work with companies from as little as 5 to over $500 million. But these accelerator folks are really interesting because they're full of passion and largely missing a lot of good basic business entrepreneurship skills. So we bring them together and we take them through all the basics of scaling up work, but really on a kind of not one to a team like I'm normally coaching a team. In this case, we're usually just dealing with the founder, the owner, and sometimes they're solopreneurs. So we took them through the. And we just did two parts of it, right? One, we had them sort of map the funnel out. So we said imagine your. So what's the ideal sale? And let's put that at the end and then when you get that sale, right, what does it look like? And then what's the first step just before that? Right. It's I don't know, handling objections or it's presenting the proposal. And then we worked back through the step and we put numbers and the key tools and the steps and the questions and the things at each point along that working back to the beginning. So whether that was six steps or seven steps or whatever it was, they went from the. And working back to getting the lead in the first place. And. And they then had numbers that they could drive. If you want to hit this revenue goal with these assumptions, you could then start to move people through it. You knew what the steps were. And then we had them work up questions for each questions to qualify, questions to discover, questions to close so that they're not just pitching things. So they're learning, they're confirming and doing that. And those are the key pieces we used of the sales playbook with the early stage companies. But I think that applies to almost everybody. To take the time and work with the team to say, what are these steps? And what are the right questions?
You are 100% plus correct. There's hardly anything that goes on on a sales call that you couldn't anticipate before you get there. As a result, there's no reason to not be better prepared. So the top salespeople in performance don't like me saying this out loud. It's actually complimentary to them, but they are offended by it. Here's the statement. The best salespeople are canned. They're canned. They say the same thing the same way each time they encounter a certain situation. They don't wing it and make it up. The beauty of them is they don't sound canned. It sounds as if it's the very first time they've ever said it. And, and, and that is part of the professionalism. A salesperson, when you go out in the field with a top guy, if you make six calls with him and he hears three times, I'm already happy doing business with a competitor. You don't want to hear three different answers. That's a guy that's just winging it. You want to hear a confident answer that takes that objection and throws it out into the street. And you can figure that out before you get there. How many times as a salesperson are you going to encounter. I'm happy with where I'm sending my business now. You're going to hear that over and over and over again. So why would you not have that in the playbook and be practiced on it? Right.
Yeah. And when I. So I did training, training to be a trainer for years, and then I trained and did speaking training and stuff. And one of the things that they had us do is work with very, very highly scripted language. Right. And the first time we worked with that stuff, it sounded awkward, like not our own words, but I prepared it and I prepared it and I prepared it and I went through lots of different sort of ego phases of preparing what seemed sort of so basic and resisting it and like that. But I. Eventually I got to, you know what? I want to be able to. You wake me up at three in the morning and. And I can reproduce this as if I owned it, as if I was the author of it, making it fully my own instead of resisting it or having opinions about it. And I got very masterful at it. I'm sure I'd be rusty today with some of that work, but that was a level of just sort of surrender and embracing that exact idea of let's distill These common, recurring things, and then just drill the hell out of them until we're masterful.
Yeah. So. So. So I'm going to add one element to that.
Please.
And that is that the very best salespeople take it to a level that I call opening night performance. If you go to the theater in New York and you're going to see Phantom of the Opera and you paid $300 for your sixth row, center seat, you know the show's been there for more than 15 years. It's. It's. It's 50 weeks a year. Eight. Eight shows a week. It doesn't matter. You don't want 15 minutes before curtain time. You don't want the cast getting in the circle and saying, man, we've done this for over 15 years, 50 weeks a year, eight times a week. Let's go make some new stuff up tonight. That's not what you want. What you want is the group to get around in a circle before the curtain opens and says, let's go out and deliver opening night performance. That is difficult for a salesperson who's playing by the playbook and giving that same answer time and time again. You. You cannot sound like the 6pm telemarker who's trying to jam something through the phone at you. You have to be authentic and say it and own it. And the only way you can get that is. Is to get to that level is by practicing. And what you just said, it becomes a part of your DNA. You don't know how to do it any other way.
Yeah. What's the quote about jazz? You just practice, practice, practice, and then you get out there and wail. There's certain something that comes from deep, deeply embedded, rigorous practice that you get to where it uses you. You no longer use it. It flows through you, that preparation. So any particular tips for practicing for folks that you want to stress? Yeah.
So there's a couple different thoughts. The first one is do it in a threesome. One person becomes the prospect, one person becomes the salesperson, and the third person is the observer, who only takes notes and doesn't talk. At the end of the session, the observer then downloads the good, the bad, and suggestions for improvement. Once that session is completed, then change hats and do it again with a new situation. And once the debrief is over, do it a third time. Anytime that we've put three people into the threesome and wore all three hats, we've always come out with two takeaways. One, the third time we did it, we were way better than the first and the second takeaway is of the three hats we wore, the one we learned the most wearing was the observer.
Yeah. You get to watch people. You get to imagine yourself. You get to think about, well, how did I or how will I do that? You get to see it through, then you experience actually doing it.
The other two guys, the prospect and the salesperson are so, they're so involved in the actual call. There's not as much an opportunity to learn until you get that debrief and fresh eyes. Right. The other thing, other thing that I would tell you is that when we do our sessions where we can, where people can buy a seat and learn sales from us, and they come from all different industries, majority of my business, I'm hired by clients to work with their salespeople. But we do public events. When we have these public events, we put people from three different industries and three different companies in the same threesome. And we're told that that is even better than working with three salespeople in the same company because you get three different viewpoints and you don't get the biases that exist in your company and industry.
No, I can totally get that.
Right. And I also want to point out what I just said. If a salesperson is tuning in here, literally, you don't have to wait for your company to call a practice session. You grab two salespeople that are friends of yours, it doesn't matter what industry, agree to meet with them at a coffee shop three times a week before you start work that day and do a 15 minute role practice with a debrief. Yeah, perfect.
This role play makes all the difference in the world. And the first time I was introduced to role play in my early 20s, getting started in selling, it was so uncomfortable. But over time, I've just come to embrace it and use it frequently in selling and negotiating and presenting and all of those things that the listener, the audience, the presenter and rotating around the position is super powerful.
Look, take anything that you want in life and I don't care what you pick. If you want to pick the people that are best at whatever you just chose, I'm telling you, they got there by practicing.
Absolutely. And finding appropriate ways to practice. Right. Effective, appropriate ways. So look, this is about a show and I want to underscore a couple things. So your best salespeople are going to can and prepare their things in a sales playbook, but they'll need to prepare it and practice it and then deliver opening night performances on a consistent basis because making it their own delivering it masterfully. Jack's books and programs and things like that will help you to fill in that we talked about some of the things about thinking through the process, about developing questions, about practicing. But that is ultimately what you're going after. You can go to the Sales Playbook for Hypersales Growth. You can read Hypersales Growth. You can read his other books. You can find those on Amazon and get into that stuff. Jack's website is jackdaily.net we'll also put up some links to some YouTube videos in the show notes that you'll get so I want to thank Jack for being on the show. I also want to direct you to if you love these shows and this topic, we've got stuff like this every single week for you and a steady stream of things to boost your sales, your business growth and everything from the world of Scaling Up. And you'll find all that at Scaling Up Business. You can also go there and download our Growth Guide which will tell you how to get started running planning and strategy sessions for your leadership team. Give you an overview of the Scaling up book and methodology, give you an agenda and worksheets and things like that so you can get started. And it's absolutely free. So go there, subscribe and get in our world and get these podcasts on a weekly basis. Jack, thanks so much for being on the show. I know I've wanted to have you on for a long time. I'm so glad to finally connect with you.
You betcha. It's been a pleasure.
All right, and everybody else, we'll see you next time. Thanks for joining us on the Scaling Up Business podcast. Are you ready to turn your goals into daily wins? You should check out our Scoreboard software. Powered by Align, it's the official software for Scaling Up With Scoreboard, you'll get an AI driven coach for priorities and KPIs and it'll help keep your team focused on what matters most. With Align, you can track your goals in real time and you'll even see results on the go. With their mobile app, you can rest easy knowing that Align has world class onboarding and support to set your team up for success. This is really more than just software. It's what I actually use to manage growth in our Scaling up client teams. Unlock clarity and results with Scoreboard by Align. To try it now, go to aligntoday.com Bill G One more time. Aligntoday.com Bill G that's aligntoday.com Bill G Check it out and try it now.




