CRO Kevin "KD" Dorsey on creating, developing, and deploying playbooks

Mr. Kevin Dorsey, welcome to the show. Appreciate you taking the time, my man.

I will always make time for Kyle Norton. There is not a time that I would not. So I'm pumped to be here, man. This is going to be good. This is going to be good.

Yeah, I'm excited and we've got a topic that I don't see spoken about or covered all that much in Internet land. And so we're going to dive in and I think have a great time. Sorry to interrupt your regularly scheduled programming. I'm Kyle Norton crofonor.com and I'm excited to introduce you to the Revenue Leadership Podcast, a new podcast brought to you by Topline. Every Wednesday we'll be diving into the strategies and tactics that drive success for the best revenue leaders in the world. You'll hear from real operators sharing actionable frameworks that you can use in your role today with no fluff, no sales pitches and just practical insights.

Today's guest is none other than Kevin Dorsey, affectionately known as kd. And KD is currently the CRO at finally, which is a hyper growth Series B startup that is the easiest way for small businesses to manage their finance and accounting. And before Finally, KD was the SVP Sales and Partnerships at Benchmark, VP Inside Sales at Patient, Pop, Head of Sales Development and Enablement at Servicetitan. Just an epic run of really impressive companies and Katie has left an indelible mark on all of them. And Katie also launched recently the Sales Leadership Accelerator, which in my opinion is the best platform and community for sales managers to learn the craft.

KD gives it all away.

I've had access for a while and can vouch that these are some of the best templates that you can swipe and deploy in your business right now. And we're going to go into a bunch of what he's built. So in today's episode we go really deep on Playbooks and frameworks and so we don't just skim the surface, talk about why Playbooks are important. We go really deep into the specifics around how do you build a playbook?

What should you build?

And most importantly, how do you implement this stuff?

How do you get people to adopt it?

This episode is a must. Listen if you want to drive predictable, repeatable, high performance in your go to market teams. I learned a ton. I think this is going to be an awesome lesson for everybody, so please enjoy. But first, a word from our sponsors.

Foreign.

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Oh, man. All right, Kevin Dorsey. Everybody calls me KD at this point. You know, I am blessed to be a husband, a father, a brother, a son, a friend, and I'm a leader of salespeople. That's what I do. I've been building startup sales teams for the last 13, 14 years now. I got a couple unicorns under the belt and they were unicorns when I was actually there and building, not just after the fact, you know, like all up, all up in there. And I'm working on my third right now. And I love this. You know, I'm blessed to be a leader, man. I get to work with people and ideally positively impact people and then share the insights with people, you know, on the, on the Internet, man. So that's. That's me.

Very cool. And you have been quietly working on something in the background yet to be announced, which. And this pod will drop shortly after that comes out. So tell people what you're up to right now. What's the. What's next for kd?

Yeah, so two main things are like happening right now, or I'll say they're next. But now, you know, I just haven't like announced everything. So one is like launching the sales leadership accelerator online, like the full community, the course, the program, like all the. That I have either learned or gotten wrong over the years, like launching that officially, you know, all the modules, all the templates, the community, everything there. So that's one big next now thing. And the second is I'm the CRO now of a company called finally, which in a lot of ways, even the name is very serendipitous to me in terms of like, finally, like finally a place I feel at home. Finally a place that I feel like can be like that last big final run. So the CRO here at finally and, you know, it's SMB and it's really bringing all the tools that SMB owners need into one place. So we do bookkeeping, we do banking, we do payroll, we have a corporate card, expense management, all in one. And so it just allows business owners to run their business and grow their business in just one place versus 17 different tools. So love the space, love the team. Already growing, already breaking some records in my first, you know, like 90 days here. So it's always fun to be like, oh yeah, this shit works. This works like weird, weird how that goes. So. No, man, it's really, really good. I'm really enjoying it.

That's exciting. And so I was a small business owner for a number of years. I serve small business owners today at Owner. So the problem that you talk about is extremely resonant to me as I was the partner that was dealing with QuickBooks and reconciling the bank accounts and all that stuff.

So bringing it all into one, you know, Like, I love SMB, man. I've done the enterprise, I've done all that. I love SMB. I love helping business owners, man. Like, I also, I ran small businesses in la. I ran three personal training studios. Like, so I just have that, like, in my heart type, type setup. So I love it, man. Loving it here, Loving the team. Really. Some big announcements like, come in there that I can't share on here yet. But, like, there's some good popping that I'm, I'm, I'm pumped for.

That's awesome. I'm, I'm excited. What, what is it about SMB that you like so much? So the Mission and serving entrepreneurs. But, but what about the, the, the segment gives you the most excitement.

So definitely, like just the mission behind it. Like, I do, I, I believe, you know, small business owners are the reason this country is what it is. It's like all these big companies at one point were small business businesses. And I think people forget that, right? They hire people, they employ people, they put their savings on the line, right? Like small business owners. What's. The. Small business owners and entrepreneurs are the only people that work 80 hours for themselves to avoid working 40 hours for someone else. You know, it's like they work their ass off to run these things and they don't have a lot of the support they need. But also, I love the, the speed of the deal. I love the speed to impact. I love how fast I can learn through things. I love all of that large space to play in. And oftentimes they're just Forgotten about. Like I, I don't sell SaaS to SaaS. I have avoided that space my entire career, potentially. I don't sell SAS to SaaS. I've avoided it because one, I felt like it was overblown too. I was like a little bit of a Ponzi scheme. Wait, you're not profitable and you're selling to me, who's not profitable and my growth requires you to grow. I didn't. That always scared me. Like that just didn't feel right. So I love that the unsexy space. Home services, medical, accounting, education, like I stay in the unsexy spaces. I also think there's more time to learn things and to apply things that don't get overblown too fast.

Very cool. I have never heard that quote. I absolutely love it. And I'm going to borrow it. Working 80 hours a week.

Oh yeah, exactly. The small business owned to work 80 hours for themselves to avoid working 40 hours for somebody else. You gotta be crazy to run a small business. And that's why I love them.

Yeah. Extremely resonant with selling to mom and pop restaurant owners. Well, cool. And I think the other part of SMB that I love and I know will resonate with you is the opportunity to have access to a ton of data to iterate, to improve, to build, deploy and see those fast cycles. Which allows you to have a very systems engineering mindset. Which we're going to spend a bunch of time on today.

Hell yeah.

Cool. So you know, you've built your reputation on building and sharing incredible frameworks. And so folks that have taken your courses through Pavilion or your own stuff that you're. You're releasing now, most people listening to this will be familiar with the Wiggle and bpsy and a bunch of stuff that you've built. And so we're not going to get into any of the specifics. You've got tons of awesome content out there, which I'll point people to. But we're going to talk about what happens behind these incredible frameworks. Like how have you built them, how do you deploy it, how do you know what to spend time architecting versus not. And so there's two topics for today. One is we'll do a primer on about Playbooks to just give people a frame of reference. And we'll spend the bulk of our time talking about how to build and deploy. So first topic is ground us. Like, what is a playbook, everybody? You know, the word gets thrown around so much. So in your mind, what is a playbook?

Well, and it's funny because in the intro you're like, you know, this isn't something people like, talk about a lot. And it's actually. I smiled a little bit there. It's like, actually I feel like people talk about it a lot. People don't do it well a lot. Right. There are full consulting agencies that all they do is build sales playbooks, and then nothing ever happens with them. So I feel like this actually gets talked about a lot. People just don't do it right. And so when I think about a playbook, what I'm talking about is a documented set of best practices. A documented set of best practices is what I view a playbook on. And I think even that would help a lot of people shift what a playbook is if they thought about it that way. Whereas a lot of times people like to say, oh, the playbook. Here's all the things like that we do. Here's like who? Like, as I know, like, these are best practices, things that need to be done. So that, that's how I define a playbook. A documented set of best practices.

And so what's in there? It's like, what do you have in a, in a playbook? Like, how expansive is it? You know, does the entire business have a playbook? Is it scripting? What types of things are you playbooking?

Yeah, so in my playbooks, I cover the five Ps. So the five Ps of the playbook are people. And we'll break all these down, like people, prospect, problem, process, and product. Those are the five things that go into my playbook. People, prospect, problem, process, and product. That's my framework for the playbook. And then I go through and all those. Funny enough, it's in order for a reason. So when you think about people, so the people section of the playbook is about your people. Right. So this is where my standards of excellence go. This is where my virtues and values go. This is where the expectations of the role goal. This is where goal setting goes. Quotas, promotion, paths. That first section is about your people. When they open up that playbook, the first thing they should be reading about is what does it mean to be a part of, of this org? What do we stand for? What are our values? What we believe? What are our virtues? How we behave. As one of the first exercises, I'm doing it with my own company here now, is like our virtues. Right? You know, you know, celebrate the process, take care of the person and salesperson, seek perpetual growth, own your shit, ecm. Every Conversation matters. Help ytp, help yourself team and prospects. Celebrate the process. Like, those are our. That's how we behave. So that people section is like, this is what it is. And people sign this, by the way, like my virtue. You read them, they're defined and you sign it. We agree to uphold these virtues and hold leadership accountable to them as well. Like that. That my org there. So that's the people section, right? That's where we have our goals. This is the prom. How to get promoted. This is a promotion path. How to be terminated. It's everything. Peoples. That first section is about your people, right?

Is your hiring framework in there?

So the hiring framework isn't in the playbook, but the virtues are how we hire, right? So I have a hiring playbook, right? I have like a checklist and like what we go through there. But this is like the sales playbook. It's just about the org and the people.

Okay. So the sales playbook is 5ps and then you can have different playbooks for how to how your managers are managing their team or the hiring.

Correct. So back to the definition, a documented set of best practices. I have playbooks for everything. Hiring playbook, management, playbook, onboarding, playbook. Like I have playbooks for all of those things. But it doesn't fit like how people think about what a playbook is, right? It's a set of best practices. That's where the wiggle came from, by the way. I know we're going to talk about the wiggle, but the playbook is the documented set of the wiggle, AKA what good looks like. That's what the playbook is, right? Anyone that played a sport, that's what the plays are, what you're supposed to do, where and what good looks like. So that's what a playbook is to me.

Okay, cool. So this is sales playbook. And then. And I think for this conversation, let's talk about it even more broadly for. Because the audience for this podcast is CROs and aspiring revenue leaders. So you've got your sales playbook. And so prospect is about the. The people you're prospecting into. Give me like pro, give me problem, process, product, like super quick.

Yeah. So problem, right? Like how? Well, like what are the actual problems you solve for the prospect? So the prospect section is the titles, the day to day. That's where the buyer's matrix goes, right? One of my favorite exercise from Jill Conrath, the buyer's matrix. Everyone in my org goes through this exercise of like, by Persona and title. What do they care about how are they judged, what does success look like, who do they report to? Like it's really understanding the prospect. And then the second part is then the problem. How well does the team actually know the problems you solve? So these are the key problems for each Persona. Here are the impacts of those problems. Here's how those problems have been solved before. Here's why those problems exist now. Now, right? So the problem section is how well can you define the problems you solve for each one of the Personas? Right? Because the prospect, that's like the industry level as well. What are the trends, what are the key terms? Who are the main players? Right, that's the prospect, problems that problems you solve processes. And this is like what our days today look like. So what is the sales process, our stages, our exit entry criteria, our qualification process? This is where scripting goes in, this is where call scorecards go in. This is where our one on one documentation goes in. Issue, diagnosis, checklist, like that's where like here's how we do our job, right? My goal with a playbook is if you do it, you're good at your job. The playbook doesn't make you great, but the playbook should make you good. If you do what's in the playbook, you should be good at your job. Greatness comes from going above and beyond on that playbook. But like if you follow what's in there, you should be good at your job, right? And so that process is in there, right? And again this is where I'm looking. We'll get into how to build it, but it's like how well documented can I make that process. Here's what good looks like for each one of these steps or each one of these things. Day to day shooting. Some of my orgs, I've literally had like last day of the month process. I love that. Here's the wiggle for the last day of the month, you pull a report on all of your clothes lost, you pull a report on any of your referrals, you pull a report on X, they get a video at the beginning of the day. Like, like we're going to define what the last day of the month needs to look like for our org, right? So that's the process section and then we get to the product section. There's a reason why product is last in. This is because now I can connect product to all those other P's. Whereas too often Playbooks onboarding, they start with the product and they forget everything else. Whereas now how does the product specifically solve Those problems, how does the product specifically align with these prospects? Right. And their Personas? Right? So then the product is at the end. There's not a product training. It's actually how it does the things we say it's supposed to do, not just what it does. So Those are the five Ps.

Awesome. This may seem obvious, but why are playbooks important? Like, why should leaders invest heavily in this? Because it takes a ton of time.

Because it. You. How do you scale without one? Right? How do you coach without one? Can you imagine? And this is what, like, I love it because, you know, sales gets itself in trouble because we sometimes use too many sports analogies. You know, like, we use all these sports analogies. But then you're like, all right, could you imagine talking to a football coach that didn't have a playbook?

Yeah.

Could you imagine talking to a basketball coach? We're like, yeah, we don't run plays like you wouldn't. But then we get sales leaders all the time, like, oh, yeah, we don't have a playbook. Or they do. And it's collecting digital dust somewhere because nobody ever reads it, right? So funny enough, now that my team's back in office is about to happen again, you could actually ping people at stagnation and at patient pop. When you joined, you actually got a physical copy of the playbook, and it was bright red. It was this ugly ass binder and it was bright red. And you took that when you're a new hire, you took it everywhere, right? So we actually. If I found your playbook, there was a fine. Like, if I found your playbook, there was a fine. Because if I found it means you didn't have, like, you carried that playbook with you meeting to meeting, session to session. That was. That was your playbook, right? They do that in the pros. They do that in the military with a lot of things as well. Like, but it was a physical copy as well. But most people, they just never use it, right? So if you're a sales leader without a playbook, what it means at its core is you actually don't have a defined set of best practices, which means you can't scale greatness. You'll just scale suck.

And that's a problem or success will be random. I find this is the other. This is the other thing. It's. You'll have such a wide variance of performance in your organization because people are reliant on figuring things out on their own, which can happen. You can throw certain people into any sales org, no matter what they're going to be successful. And so oftentimes I argue that you should judge a sales leader not by their best performers or really by their worst, but it's. It's that middle section, like, how great are they? Because those are the people that are operating by your playbook and executing and really, like, driven by your coaching.

And we'll get into this, into the building, right? This will probably set us up a little bit, but I was talking with a company, this was about three, four now, about five, six months ago now, where they say, like, yeah, like, our top three reps, they don't follow the playbook at all. Like, what should we do about them? Playbook, Right.

Exact.

I was like, anyone's ever worked with me, like, knows exactly what I did next, right? It's called, like, the. The KD slowdown or the KD pause, where I'll, like. I'll make you say it again slowly. I'll go like, all right. I want you to say that to me one more time, but really slow. Our top three performers don't follow the playbook at all. What does that make you think maybe is actually the problem? Right. You caught it.

The playbook.

If they're not the problem, your top three, those. That's the playbook you need to be following. That's the playbook you need to be defining. And you're looking at it completely the wrong way.

Yeah. I often tell this to folks newer on my team is start with the playbook, but then beat my playbook. If you can beat the playbook in terms of your conversion rates or the approach, the efficiency by which you're tackling the job that is outside of it, then let me know and let's update the playbook, because I want everybody doing it.

The quote that we start our new hires off with is, imitate first, innovate second. Imitate first, do this. Imitate first, innovate second. You know, and we did, like, I lead the first session for onboarding always. It's three hours long. It's the first session. It's with me.

Three hours. Three hours.

Three hours. Once a month, I run that first session. We're covering the playbook. We're covering expectations, we're covering how to succeed. We're covering the virtues and the values. And this is one of the things I talk about, is, y', all, I have gotten more things wrong in this than you even tried yet. I need you to trust my mistakes. I think about this every day, every day for the last 13, 15 years of my Life. Okay. Imitate first, do what I'm asking you to do first, then innovate. How silly would it be to come into an org that is running, that is operating, that is succeeding, and go, I'm going to do something big differently immediately. That's a silly way to approach it. Imitate first be good, then be great.

Yeah. Most of the reason I chose to do this podcast is now I get to drill people I respect with questions for an hour every single week. And this is why, because hearing you say that you spend three hours with every new hire cohort, I'm like, I knew I was going to have something to want to make me up my game. That. That's awesome. Y. Amazing.

Like, I'll just sit speaking to you just personally as, like, as a friend or something. Like, like, the how that sets the tone, bro, is unreal. Like, it's like, look, let's call it all out here. We're going to get you hyped. But also, you know, here are the expectations, here's how you get promoted. Here's what these virtues are. You can hold me to these. If you see shit happening out there that doesn't match these, I want to know about these things. I am going to push you. I am going to challenge you. Right. But here's also what success looks like on the other side. Like, it sets the whole tone. And then they know. They've heard it from you. They've heard it from you. Not from a manager, not from onboarding, not from hr. They've heard it from you. Which then also makes some of the. Any early performance conversations actually very easy.

Yeah.

I just sit down with you and go, Kyle, remember this? And we talked about this.

Yeah. You've got people signing it 100%.

This is your signature. We back on the same page here.

We're in the process of overhauling, overhauling our new hire process. And this is going to go into it for sure. So it can. One of the pieces of feedback I get a lot when I talk to folks about this is it can feel like just overwhelming. I have no idea where to start. Like, you know, people hear you talk about there's five Ps and there's a hiring framework and then there's a playbook for this and that. You know, it. It can just feel overwhelming and I think paralyzing for. For folks. So where. Let's give some advice to early sales leaders and, like, where. Where should they start? Like, how. How should I get going? I want to codify my approach. What are the first things to build.

Yeah. So the first things, you start on the people section. The first thing you build are the virtues and expectations. First, here are the behaviors we expect of the org and what they mean. Here's the expectation of the role. This actually doesn't take that long. It's just blocking the time to do it. So you start. There are the people. That's the most important part of the people. You can build everything else out, but, like, that's the most important. Virtues, expectations of the role. Then you get to prospect. Buyer's matrix. Go Google it, y'. All. Buyer's matrix. Jill Conrath. Go Google it. Free download. Put it in your playbook. Buyer's matrix.

Jill Conrath. Og. Goat.

Og.

You don't.

She doesn't come up as much anymore, but.

She. She should. Like, that's just like every buyer's matrix. I will forever go through, right? Buyer's matrix. Go through it. And I'm gonna give a bonus tip at the end of all this. Then you get to the problem. So the problem, right? And this is from. From Keenan. If you're trying to do this, just the pic problem implication chart. Here's the problems. Here's the implications of those problems. You write those out. And y', all, if you're listening to this, you probably should be nodding because you already know this stuff. The Playbook is in your head. The problem is in your head, right? Then you get the process. Call scorecards, scripting. But if you don't have scripting, at least call scorecards. Here's a disco scorecard, demo. Scorecard pricing. Scorecard. Cold, like. And again, you already know what your scorecard is because it's in your head. When you sit down with a rep, there's 10 to 15 things you're listening for on a disco call. Get them out of your head, put it on paper, right? Then you get to the product. And the product is basically feature. I've grown up here a little bit, so now it's ctd, but it used to be stfw. Here's the feature. Stfw. Here's the feature. Here's the feature. Now let's connect the dots because I'm growing up, maybe kind of trying, okay? But like, so that right there, y', all, that Playbook would be better than 90% of the playbooks out there. It gets you started that you can build from. But then here's the beauty. You don't build it yourself. You have a team. Guess who helps build my Playbooks?

Managers. Reps enable them.

And everybody Managers, reps, everyone helps me build the playbooks. This is not me going into some ivory tower and walking down like Moses with the tablets, like, hey, I've got, you know, reps out here, even. And this all happened when I had a team of only, like, eight. And then, like, I was like, how do I build this? It's like, all right, Kyle, you've got buyer's matrix for office. Manager. Brian, you've got buyer's matrix for controller. Jenny, you've got buyers. Like, you just assign them out, and it's going to get done 80% of the way. We sit in a room one hour. So actually, I mean, this is a recording. I could show it to you. So on my calendar every week right now, there's an hour blocked with my three main, like, revenue leaders called the Weekly Wiggle. It's called the Weekly Wiggle. It's an hour we get together to build, not to discuss, not to chat. Okay. We are working on the call scorecards today for an hour. You know how long it takes to build a call scorecard, Kyle?

Less than an hour, that's for sure.

Mm. Done. Done. Right? So to give some context here, y', all, as of this recording, I have been in seat for 90 days. As of this recording, I've been in sync for 90 days. Guess what's already done. The five B's, virtues and values. Done. Goal setting. Done. Buyer's matrix. Done. Call scorecards for each one of our main calls and our different sessions. Done. We're right now working through the product STFW feature by feature. And we've already done the problem set. It was already done. And for further context, in these first 90 days, we have already increased close rates by over 38%. Our ACV has gone up by 17% already. In these first 90 days, we've broken two revenue records, and our lead to clients already almost doubled.

Hell yeah, man.

Like, this shit works, y'. All. You just have to go and do it. And it doesn't actually take that much time. It really doesn't. You just have to block it to do it. But I'm leveraging my team. And what do you think that's done with my relationship with the team? When I pull nine or ten of them in and say, hey, I could use some help with this, so I'll keep going down this path. So I actually learned this recently from Patrick Bet David at one of his seminars, and he said, a leader should never do anything alone. I was like, whoa. He's like, if you're ever doing Something alone you're missing. So what I created is like I created, I said, you know, to the team, like, here's the main things I'm working on. If anyone here is interested in these things, let me know. And then I created these. It's called Never Alone Slack Channel. So never Alone Marketing optimization, Never Alone scripting, Never Alone onboarding, Never alone. And I've got people in there that I can say, hey, I'm working on this, could you help me out? And it builds the relationship, right? So leaders, you shouldn't be building this by yourself. Go to the team and if you don't know what the plays need to be, go shadow your best. Go shadow your best. The playbook should be built off of the best practice, not just the practice practice. Like what's the best practice? And do you even know what the best practice is?

Yeah. How much of a framework are you giving them to sort of fill in the blanks.

Oh, okay. Well, actually this is a two parter because I'm gonna go to the ends the other side. One of the biggest shifts I've made with onboarding playbooks is they are fill in the blank. Literally. Literally fill in the blank. So the number one problem for the office manager is, and it's blank, they have to fill it in as they go. So this is a shift I made at my last order that I'm now doing here because that's going to increase retention. If I just give it to you and I tell you, right, you just read it. Oh, the number one problem for like the restaurant owner is blank versus the number one problem the restaurant owner is. And then they have to fill it in as you're teaching it to them, it increases retention. So I build the playbook first and then for my new hires, I blank things out. So as we're teaching it to them, they can fill it in. Right. So that's the actual literal fill in the blank type setup. But on the flip side for frameworks, Right. My goal with frameworks is again, it should make you good. Like if you follow this, you'll be good at your job. And that is pretty specific. Like there are certain things college, you know, make a good disco call, you know. So I'm going to document that and.

That the question's really like, you want to engage the team. And so the process of engaging, you know, you tell a rep, I need your help to build this part of the playbook. If you give them a lot of white space, they're going to be going sort of all over. So Are you saying this is my rough. This is the.

I show them an example. Like, here's one of the ones I've built. Can you go help me build this out here?

Right. So it's all them to fill in the.

Yeah, right. Here's what I need for a pic chart. Right? Yeah. What that problem causes, what are the implications of that problem? Here's one that I did for invoicing. Could you do this for receipt collection? Right. Like it's just always an example they can follow. But then, yeah, then they. They go and do it.

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See you in Austin on the fill in the blanks part of onboarding. If. Are you familiar with Bloom's Taxonomy, I'll send you this. It's exactly what you're talking about. There's certain activities that are going to generate more retention, recall and skill development. And it's a pyramid, just like Maslow's hierarchy. At the bottom is remember, like give somebody information and ask them to remember. And then it's understand, apply, create as the top. Like analyze, create at the very top. And so the more you can architect your any skill development exercises to the top of that hierarchy. So here's a framework. Create a new call script. I'm going to basically throw out those call scripts. But getting somebody to take the principles, like I've got a set of cold calling principles. Pattern, Pattern interrupt. Credibility, Relevance, Intrigue, offer of value. It's like, go write your own call script. I don't want them to use that call script. It's not going to be very good. But the process of creation bakes in. Now I understand. Okay, I need a pattern interrupt to go from system one. System two. So the Bloom's Taxonomy thing is really interesting to get your managers to understand. Because the hard thing is we've gone through an education system. That's all. Just remember, remember and regurgitate, which is the worst form of learning. So. But it's the thing that feels natural to us. So I'll, I'll flip you the. A couple links that I. That are in my management development book.

I love.

Okay, so last. We're going to skip that. Let's get into building and deploying. I want to be mindful of time here.

So.

You'Ve talked about the components of a sales playbook, but there's problems that just come up in your business. You know, we have a conversion rate issue here. We've got a, we've got a problem with employee retention or mishiring. And so how do, how are you allocating your effort around what playbooks to build, what problems you're focusing on? Do you, do you have a prioritization framework for. Because you know, time is very limited that we're in the resource allocation business. So how do you think about deciding between what things to work on?

I mean, a lot like I'll say like within selling, right? Is I'm looking at what is the impact of it. So a phrase that I use is a CRO. Like, right, that's what I mean. Yeah, that's what I'm looking at is like, what is the impact of this problem that I'm trying to solve, right? So the phrase that gets used often here is volume or volume.

Volume.

Is it a high volume problem, meaning it's loud or is it high volume problem, meaning there's a lot of it. Volume or volume. Too often revenue leaders are focusing on loud problems. They're loud, but it's actually only happening 3% of the time, 8% of the time. I'm trying to focus on the high volume problems, meaning that there's a lot. It's happening a lot, right? So that's my first gamut. If I'm looking at where to solve. Is like, is this a loud problem or is this a high volume problem? There's a lot of it. And then from there, this is where all the metrics come in. Is like, what metric is it attached to? Like what is what metric is this impacting? Okay. And I'm maniacal in terms of prioritization. It's like, yeah, whatever, show rate might be busted. But you know what's worse are closing. I'm going to let show rate burn a little bit. Just tell me this. One of my directors, I was like, dude, so much about Leadership is controlled burns like, all right, the barn is on fire. But if it's controlled, I got to go save the house and I got to go save the house first. And so it always comes back to a metric for me is which metric am I trying to impact to help prioritize where I'm putting resources to solve the problem? That applies to the playbook too. It's like, hey, what's busted? If I look at all my metrics, what's the worst one right now? That's where I'm going to start diagnosing plays. That's where I'm going to start figuring out, like, what needs to be done to solve it. So I filter it through volume and volume, then I connect it to a metric and I go from there.

Cool. And then what are you using for inputs? So you're developing, say it's a playbook you've never had to design before. So it's not a sales playbook that you have an existing framework. But you know, say you've inherited a post sales team for the first time and you need to go build new sets of things for that team that you don't have reference points for. How are you balancing between anecdote and data? Are you participating in calls? Are you relying on, on the team? Like, where, what is your fact finding look like to start?

Yeah, like, I mean, you use the right word there. It's like, I go get my reference points, but I, I observe, I don't ask, I observe, I don't ask people what they do. I watch what they do. Because this happens all the time. You sit down with the top performers, like, what do you do? And they're like, oh, this is what I do. They don't know. Like, they, they don't, they oftentimes have no idea what it is they do do differently than anybody else. Right. So if I was inheriting post sales, quite literally, my first step is who's my best person. My first step is who is my best person, who is the best post sale. And I'm looking at that both in terms of, say, outcome, but also metrics. And it's like there's the revenue, but sales leaders, please hear me. Just because someone has the highest revenue doesn't actually necessarily mean they're your best rep. Right. The metrics are going to help you actually know who the best rep is because let's say someone's closing, whatever, a million a month, but their close rate's 14%. You know, someone else is closing 750k a month. But their close rate's 35%. Who's a better rep to build a playbook around, Right? Yeah, I'm picking that 35 percenter more than I am a 14 percenter to build the playbook. But then, so back to this. I'm observing, I'm going to watch step by step what it is they do to find the patterns. Right. This is. I know I'm not allowed to talk about it, but this is where BPSI comes in. Yeah. Behaviors issue, diagnosis, process, skill. And you. What are the behaviors of that top performer? What do they do that's in their control? What are the skills of that top performer? What is it they do well, what is their process? How do they work through these things? So that's where I'm going to get my reference point. And again, you can learn very quickly, very, very quickly on these things, especially in remote. I can have you record your screen. I can get screen recording played on 2x and watch and document what's occurring there. And then I'm good to go.

Yeah. There's a concept in psychology called stated versus revealed preference. People will state that they don't, like, they don't want to eat sweet foods and bad things, but if you observe them, then it's a totally different set of things occurring. And this is, you know, very. I love your point on observe, don't ask. I think there's some ask, there's some helpfulness in asking.

Always be clear. I'm going to ask like, hey, like, how do you go through this? Like, But I'm always combining that with observation, always. Because I can learn through that faster because I can see what's actually being done. I can't. Again, playbook, a documented set of best practices. A practice is something that is done, not just said, I need to see it done that way. And this, you know, whether this is controversial or not, there are times that I go in to do the thing right, like, all right, like, I'll, I'll make some calls, I'll run some deals. But it's actually rare that that's how I'm going to learn the fastest because that's just me proving I can do do it doesn't actually mean I'm learning the best practice, because best practice also doesn't mean I can do, means can the majority do it. This is also where playbooks go wrong sometimes, is they're built on this. Like, well, here's how I would sell.

There's.

There's stuff you can do, Kyle, that your average AE cannot do. There's stuff that I can pull off that an average AE cannot. That does not mean it's the best practice. That's what goes above the playbook. That's what we get beyond it. But in there, it's like, what can the majority do? And do well? That's. That's what it is.

And do well. By a certain point, there's always this ticking clock. We have to get people ramped fast. And so trying to teach them the master version of some skill versus the.

Yeah, it's just silly. It's. It's just silly. I'm already revamping our onboarding here. It's like, yeah, we get them on the phones in four days. And I know this always fires people up. I'm like, why, though? Why. Why are you getting them on the phone in four days? Well, they gotta get there at Batson. No, that's. That's the game. You're putting them into the game when they're not ready. Why, one, would we burn those leads or deals, but two, what that does to them mentally, That's a. That's not. That's getting them on the phones fast. So I get them ready fast. Right. The playbook also, if you think about it, those are the answers to the test they have. They know what good looks like. They know what they're trying to get to. To your point. So that also speeds up ramp, because they know what they're trying to achieve. Here are some examples of good calls. Like here. So I wish I was in my home office right now. I could bring up a couple playbooks that I have in the office. I could show you. Like, we even had specific role play scenarios in the playbook of. Here's the scenario, here's what you're going to practice. Here's what you're trying to achieve. All that in the playbook?

Yeah, yeah. We're piloting and deploying this new tool. It's like an AI roleplay. It's an AI roleplay tool, but it's built off of all of our stuff. It's what you all use.

Or you can put it in the chat, because I'm using one too right now, and I'm.

It's called Ramp Systems.

Okay. I'm using hyperbound.

Hyperbound. See, I looked at hyperbound and I. I didn't know how custom I could get it to my environment. But I've given ramp calls, playbooks, scorecarding, a bunch of stuff, and it was like, sort of scary accurate. And so we're now trying to this, this idea of practice field, playing field, getting, giving reps an opportunity to just do way more practice reps. I have this, this concept of called isolation drilling and a lot of it's from talent code. So progressive resistance, the 60, 80% learning zone. Like, I want to be pretty prescriptive about how mock calls and practice is done, but reps don't want to do it. Managers, managers don't like doing role play either. I'm willing to bet that is the case for 90% of people. And so by using a tool to give people, hey, like I need you to do an hour of handling knee jerks and over the course of a couple of days, I need you to do an hour of dealing with late call objections or asking for the business. And so I think there's a lot of opportunity to extend. We are in the like four, four days get people on the phones camp right now. But that's a lot because of the speed our business is moving at. But I don't actually think it's the right thing from an outcomes perspective. And so hopefully with tooling in place, I can extend that. Give people more practice and training and have them more prepared for the ride.

Yeah, yeah, we're doing the same thing with Hyperbound. My team practices every single day now. Every day, Entire team, every day. They are in there. They're my new reps. I mean, they will literally be practicing for three to four hours a day. And that's how I build my onboarding, by the way, right? Is my. When I look at onboarding, I'm like, how fast can I get you ready? Not how fast can I get you on, Right?

Yeah.

So you're practicing for three to four hours a day even when you have people, right? Because the beauty is if you have a team in place, right? Like that's literally they would spend 30 minutes with a rep or manager the last three to four hours of each and every day practicing the intro. They just spent 30 minutes with you practicing the intro. Then they're going to go with someone else and practice the intro and they're going to someone else to practice the intro. But by the time they're on the phones, they are ready. Like, I have this weird idea that if you can't do it in practice, I know you can't do it in the game. Shocking, right? It's like, why would I put someone in the game when I know they can't do the thing? Man, I'm controversial, right? This is why they pay me the big bucks. It's like why would I put some game when they can't do it at practice? But the tooling now makes it so much easier. I love it. I absolutely love it.

Yeah, we'll have to swap notes on these tools. I looked at a few. So do you have a hard stop at the top of the hour, by the way?

I can go a little bit over.

Okay, let's talk about operationalizing a playbook. I think this is the thing that potentially leaders have the hardest challenge with. It's, I've built a playbook, and now nobody's using it. And we've talked about one of the problems, which is, like, maybe the playbook's not all that good. And for me, that's about trust building. Like, you have to build enough trust that people can bring you problems. Like, hey, this part of the playbook's no good. And that's like a psychological safety thing. But so let's just say that the playbook is good for this question. How do you operationalize it? So I've built something new. Like, you're changing. Let's say we're changing BDR scripting, which I'm imagining you've done recently. How do you think about deploying this? Getting adherence measuring. Like, what's your process there for deployment?

So it's a few places. So one, funny enough, first and foremost, is through practice leaders. Hear me out here. A playbook is meant to be practiced, not read. You don't read a playbook. You don't go to football practice and read it. You practice the plays. So this is the first place that most orgs miss is they're not practicing the plays. They wrote it down and it's there, but they're not practicing it. That's the first part. Like, the playbook is much. So how much. How much practice until they can do it.

Okay, give a frame of reference. So you're deploying a new BDR script on Monday. What's the volume of practice that you're likely having them do to get that?

If it's. If it's scripting, 30 minutes a day.

Okay. Okay. So playbooks need to be practiced. That's one part of deployment.

Yep. Second is they need to be referenced, meaning send your people to the playbook. Send them to the playbook. If you're getting asked questions about things that you know are in the playbook, send them to the playbook. Too often as leaders. What do we do? We just answer it?

Yeah.

Hey, Kyle. I keep getting this. You know, not interested. Objection. What should I do? We put Our super coach cap on and we say, oh, let me teach you. Hey Ashley, jump into the playbook real quick. I think it's like page 13. Give that a read and then we can talk about it. So you reference them to the playbook, right? That's the next step is you need to be bringing it up often. Third, we use the playbook in our trainings and coaching sessions where the scorecards, they're in the playbook, where the Persona guys, they're in the playbook. Like it's, it's there. So we actually bring them into the sessions that we are running. But then the truth of the last, I'll say in terms of like deployment to get it, like to stick is the updating of it. If you are bringing it back up and updating it with new information, that also keeps the team engaged with it. Whereas like, all right, this is the new plays that we're supposed to be running, right? So consistently updating it also keeps the engagement and deployment high because they're seeing it more often. Right. In my one on one docs, there's a link to the playbook right there. In the one on one doc, there's a link to the playbook right in there. People can go and reference it. So those are the biggest things I say. You practice it, you reference it, you send people to it. Right. You bring it up often and use it in places and then you keep updating it because that keeps it top of mind. Whereas too often a playbook, like you know, where I, you know, I joined, joined finally and I was like, you know, send me the sales playbook and they sent it to me and I pull up that version history and I know exactly when the last time that thing was updated. Which means I know exactly the last time anybody even looked at that thing. Right. Gotta bring it up more often.

And how, how frequently are you updating things? Would you say?

Whenever I learn something new, like if I learned something new, I'm updating the playbook and then I'm sharing that information with the team, right? So this is something where, so we do the, we do the quarterly wiggle, right? So every quarter it's called studying. Greatness is the name of the exercise. So every quarter I assign to my managers either a metric or a process. So all right, so Kyle, you've got acv. Jenny you've got close rate. And it's that person's job to identify who has the highest of that metric or who performs at the best and to study them. What can we learn about Their process. What's the bipsy for Kyle on close rate? Why do we believe he's closing at 34% when everyone else is at 19%? So every quarter, there's an intentional exercise with my leadership team of can we understand greatness? And almost every time we learn something new that that person is doing, that goes into the playbook. And now, full circle back, they were updating the playbook based off best practices from the team, which also gets buy in. Hey, y', all, we're changing how we're doing pricing because Julia has a higher ACV than everybody else, and we figured out why she presents pricing like this. This is how I want us to work on this now. Playbook is updated. Scorecard is updated. Practices run over the next, like, three to weeks to get it down. Cycle continues.

And so you've got an operating cadence for Playbook development. So you've got a quarterly wiggle. So that's. Every manager is going to go study one sort of skill or outcome. Yep. Are there any other operating rhythms that you have in place for Playbook development? Updating, monitoring.

So the development. That's the weekly wiggle that I'm doing right now with my. With my managers is we're getting together every.

The weekly wiggle to build.

Right. Here's what we're focused on. Actually, there's a dock. I mean, I don't know if this is a. Are we doing any video on this or.

Video.

All right, I can. I can pull this up here real quick. I'll share this real quick so people can see. Where did it go? There we go. So one of the first docs that I built for my leadership team is project code name the Wiggle. What do we need to savage the wiggle for lead handling? Need Towering, cold telling, social. These are all the things that we have to establish the wiggle for. What are the steps of that? The diagnosis. Okay, who's the best at this? Can we define? Once it's been diagnosed, we have to document it, demonstrate it. So we're literally week by week, picking the wiggle, working on it for an hour. Right. So, like, this is like that process that we're going through, but it's blocked on the calendar. We get together, we know what one we're working on. Because also, I think you have it. You have three different teams. So the wiggle for disco for this team is different than the wiggle for disco on this team. And I need that separated. Right. But we're coming together to work on it at the same time. Just to make sure it gets done. Because too often people think this takes way longer than it does. Right. You know this stuff. Right. Anyone that watches like you know what good looks like for this and get it out of your head, put it on paper.

Yeah. And that process is that in your.

New course, the how to build, like how to build a sales playbook is in there. Yep. How to scale greatness. It's in there.

Cool. Nice. I am a strong supporter of the KD content. There's so much, there's so much bad stuff out there right now. I'll go on the record as putting my name behind your stuff. One of my reps, one of my managers did, I don't know what of your courses, but a lot of that's where I borrowed your end of week miracle or whatever you call it.

Yep.

Yeah, we, we, so we have our own version of that now. But, but that was a really valuable course for him. I looked at a bunch of content. I mean I, I read a bunch of urine Jake Dunlop stuff which I liked. So there is a world of crap content out there. But folks should definitely, if you're a newer VP, sales, even experienced VPs of sales like you can accelerate yourself fast with borrowing some of these concepts.

Hell yeah.

Okay, last, last question. Measurement. So how do you measure whether or not a playbook is actually being adhered to?

So it depends on like what part of the playbook. Right. But like let's say like scripting. While measuring that in the call recordings and the transcripts, like I know whether or not that's occurring.

That's what that call manual by the managers. And are they like filling, doing a checklist, Are they scorecarding? Like what's, what's the.

Yeah, so that, I mean that shows up in their one on ones. Right. So in the one on one process which is also documented of like here's how we run a one on one. We have our one on one doc that's updated. Like in there is like here's what we're working on with the reps. So the manager one on one for me is, you know, there's team performance but where we spend most our time is rep by rep. What's the number one metric? What's the issue, diagnosis? What's the coaching plan for it? That's where we spend most of our time in the manager one on ones. And so that's where I'm learning what is happening or what is not happening. And then the managers obviously run their one on ones with their reps. Same Idea. What's the number one metric we're focused on? What's our process to improve it? Where we focus coaching wise. So that's my first measurement is within the one on one process. But more often than not, the easiest measurement is, is the metric where I want it to be?

Right.

Because the metric is where I want it to be. Then I can have a strong assumption that the play is being run if someone is below right. If someone, let's say like one of my reps right now, they have a show rate of like 47%. What do I already know, Kyle? Like I can guarantee they're not running the plays they're supposed to run when it comes to show rate. And that's also, you know, this is in the playbook, but I don't know if we call it a playbook. That's where the issue diagnosis checklist comes in. So I have an issue diagnosis checklist for every key metric in my org. So if someone has a low show rate, this is what you look for. How far are they booking the meeting? Are they getting the calendar invite accepted? Do the calendar reminders have a problem based language in them? Who are the booking with? Did they establish a problem on the cold call? Did they sell the ae? Did they sell the meeting? There's like three other things. What do you think the odds are someone's doing all of that and they're not having a good show rate?

Slims at absolutely zero.

Absolutely zero. Unless they're completely cheating the system somehow. Right. If they're just booking fake meetings, well then show rate is going to be down like you become ungamable. So that's, that's the checklist. Right? So number one metric issue diagnosis, coaching plan. And again, that's fast. I can very quickly figure out like, oh, shoot, they're booking them out two weeks from now.

Cool.

Well, that's awesome.

All right, we're coming up on time, so I want to get into a quick fire. What do you wish you knew as a new leader that you only came to understand sort of many years into it? If you could go back and give yourself one piece of advice as a, as like a new people leader, a new second line leader.

One piece of advice, one and one only. All right, can I do two fast or just one? Two fast. Because one. One's tactical, one's theoretical. The theoretical thing I would have said to my younger self is you don't turn people into you. You can't turn them into you. Your job is to make them better. And early on in my leadership life, I was trying to make everybody like me, work like me, sell like me. Like, that's not what true leadership is. Your goal is not to make people like you, your people, is to make them better. That's on the theological side of this tactical side is document the wiggle. Like, so much of the wiggle lives in our head and we wonder why we can't scale or why we're the bottleneck or why we have to get involved in everything is because the wiggle's in between our ears. We never documented it, and I think I learned documentation earlier than most. I wish I had learned it way earlier. Of like, this is what good looks like documented. This is what good looks like documented. And then update the documents. That would be my number two. So one, don't try to make people. You two, document the wiggle. That would have changed my leadership life immensely.

Very cool. Not in the rapid fire, but how much time a week do you think leaders should be spending on documenting the wiggle and playbooking?

I mean, depends on if you have it or not. Like, once it's built, it's actually not a lot of time. Right.

If you're so say they don't have much. Because I think that's.

They don't have. They don't have much. I will throw a question back to the audience first, which is how valuable do you think it would be to have your best practices documented for your org? And the moment you answer that question should tell you how much time it's worth to do so. My recommendation, like, I think you and I have talked about this in the back. I love something that's called a dark week. Sales leaders, this is going to give you nightmares, but it's going to change your life. So dark week is a week off of work, to work on work. So it's. You're not in meetings, you're not in the office, you're not in Slack, you're not in emails. It's like you're on vacation. But it's an entire week dedicated to working on your orc. I leave a dark week more energized than any vacation I've ever. I ever take anything. Because you get done right in one. If you did a one dark week, you'd have all this done. One dark week, you'd have literally all of it done. That's when I build out scorecards. That's when I do observation and like, like studying of things, going through transcripts, documenting. But if you can't. And also you're like, well, I can't take a dark week then. That's exactly why you should. Because if you think you being gone for a week is going to break your org, your org is not set up the right way. That should actually be your signal. You're the bottleneck that if you aren't there, shit falls apart. That means you don't have your best practices in place and you don't have a leadership system in place to run it. So dark week, you just knock it out. But if not, at least three hours a week. Three hours a week, 90 minute sessions per week until this is all done. It'll take you about a month and a half. Most Cool. Nice.

What's the most common advice you give to your new leaders and or mentees?

The most common advice is funny, you.

Get the one you're just repeating yourself constantly on.

I am not you, you are not me. We are not them, they are not us. I am not you, you are not me. We are not them. They are not us. And it's a constant reminder of we cannot just lead the way that we like to be led and we cannot expect them to think the way that we think or to operate that we the way that we operate. I am not you, you are not me. We are not them. They're not us. That's my number one always. Because too often leaders are like, oh, like they're not, they're not doing this, they're not doing that. It's like, okay, but like, they are not us. Does not matter how you sold or how we did things. That's why you're a CRO. You're better and you're different. There's nothing wrong with that. But you're better and you're different. The rest need a certain type of comms to come through. That's probably my most common far and away most common. Second would be like, what's the cause? Do you know what's causing. Right. The result. Right. Both good or bad. Right. Do you know what's causing bad result? You can't just tell me the result's bad, what's causing it? Or do you know what's causing the good result? Which is actually where most sales leaders miss. They don't know what causes the good. So like we have, we have a phrase we use. If you can't explain it, you can't claim it. You can't explain why your team did well. You can't claim that success. You need to be able to explain.

I like that my management team likes to Tease me. They'll quote me and say, what drove this? Because I'm constantly saying, somebody brings me something, oh, this awesome thing happened this week, and they know I'm going to respond, what drove this? Because I'm always obsessively trying to figure out what's on. Okay, last two questions. What's the hardest lesson you've had to learn?

Releasing control. Releasing control. As a seller, you control. You control your destiny, you control your output. You control oftentimes how much you produce. As a leader, as much as you think you're in control, you actually have less control. You can't control things as a leader. You can put systems and process in place, but releasing control, one of the biggest lessons for sure. I say, like, it does. Just doesn't always work out. Like, you know, like, sometimes it's just not a good fit. Sometimes it's just not the right place for you. That's a hard lesson because our egos get in the way. Our. Our heads get in the way of being like, oh, like, I'll figure this out. Sometimes it's just not a good fit and being okay. Say, like, it's just not a good fit.

Yeah. I was listening to a podcast with this author, Brian Klass, who wrote a new book, which I just picked up, but I haven't read, called Fluke, and this quote stuck with me. He's like, you control nothing, but you influence everything. And I think it's such a good reminder. It's like, you don't control how people behave, but you have an insane amount of influence. And I think that's a. It's a. It's an important shift as a leader because you could. You have so much more direct influence as. As a rep on. On a ton. Even though there's a lot outside your control. Is your patch good? Did you get the right Bluebird deals?

But happens, right? But it's like, it's. It. Selling is selling so much easier than leadership. So much easier. There's probably about a week that goes by. I'm like, man, I should just go back and sell. Like, that was fun. So it's easy, like, you know, but this is what we do, man. We're builders, we're scalers, we're coaches, we're leaders. It's just who we. Who we are. But no, selling, you know, was easier. Just was.

Yeah. What's the best thing you've read in the last 12 months?

Ooh. I really. I actually really did enjoy Friction Project. I thought that was a very really. I thought that Was a really good read. So that one was. Was fun. I came back to the Almanac of Novel Ravikant again this year. It's been a couple of years that I read still one of the most highlighted books. That one was, was really, really good. I really liked Friction Project. It was a good, good reference point of like the whole concept of the book is where can you decrease friction where you want more of something to happen. Where can you increase friction in places that you want something less to happen? And then like being able to look at your org and your processes to go like, okay, like, where can I make things easier because I want more of it? Where can I make something harder to prevent it? So Friction Project is a really good recent read. And then Almanac of Novel Ravikant is just phenomenal. Just so good.

Very cool. There's an awesome book called Nudge, which is by Richard Thaler, one of the early behavioral economics guys. Very similar thing like, how do you add friction? There's another talk that I frequently share by Lauren Nordgren. And so he's a researcher and he talks about like the difference between fuel and friction. He's like, we're obsessed with fuel and giving things fuel to make them go better, but really we need to think about removing friction. So lots of the same concepts. I'm going to have to grab this.

One because he talks about in the Friction Project too, of just how often adders are rewarded, choppers are not, and our default is to add something. So if something's not going well, our default's like to add to it. Okay, let's do more of it. More people. Let's add more meetings, let's add more steps, let's add more. When it's like, it's the eliminators that actually, and I'm not saying eliminating people. Calm down everybody. But it's like our defaults to add when oftentimes subtraction is a better process to go through. So it's a great, It's a great read. Biology was another good one. Bui ology, that was also really good book on like how we make buying decisions.

Nice. Cool. So where can people find more from you? I'm sure lots of people are going to be wanting more. So where should we sell them?

So definitely, you know, LinkedIn, you can find me there. And then sales leadershipaccelerator.com. that's where I'm putting all this stuff. And all the content, all the programs, all the courses definitely go there. Sales Leadership Accelerator.com. that's it.

My man, that's awesome. Well, appreciate the time. I have a whole raft of notes and I'm feeling like I got to step up my game now. So this was a great conversation. I'm excited for people to listen to it. I think it's going to be a really valuable one. So appreciate your time.

Hell yeah, man. Thank you for having me.

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