139: What Great Prospecting Outreach Looks Like With Doug Landis

Thank you to our sponsors, LeadIQ, Costello, SalesLoft, WorkRamp, and Dialpad for helping us produce this podcast. Head over to jbarrels.com slash blog for the highlights of this episode and explore resources you can use right away. Let's make it happen. Good afternoon, everybody. This is John Barrels making it happen Mondays, and I don't even need to introduce this motherfucker. My boy, Doug Landis. What's up, man? How you doing? How's it going? So I think you're like two peas in a pod. Yeah, I was going to say, this one's going to be an easy, this one's actually going to be a hard conversation for us to keep like down to half hour, 45 minutes, I think. But for those of you who don't know, like you came on the podcast way early on, right?

When I first started doing this? Yes. Yeah. So for everybody who doesn't know, Doug Landis, and I go back quite a ways now, about 10 years, I think. Yeah. And it stems from actually using the training, going after Salesforce. Doug was at Salesforce. You want to tell that little story for some context here? Yeah, that's right. That's right. It's funny you say that. We were just talking about this yesterday. In fact, it'll be part of our conversation as we continue. But yeah, so about 10 years ago, I was running productivity at Salesforce. John used his YUY email model and approach, sent an email to Frank Van Vien et al, who at the time might have been the president of Salesforce, and then George Hu, who was the CMO.

They both sent me an email directly and said, hey, we want our people prospecting like this. And I was like, ah, son of a bitch. I don't have to actually take a meeting. True, scary, right? But I reached out to Mr. Hoffman, and he's like, cool, your guy is John. And I'm like, all right, John, what's up? We brought you guys in. And even to this day, I was just hanging out with Frank Perkins, who's still a senior sales leader over at Salesforce. He's been there for 12 years. And he's like, literally, your training was the most important training we did at the time, without question. And it still matters. Although, I think, as you and I have discussed, I think it's time that we shift a little bit away from this YUYU now model, if you will, and actually take it a step or two deeper.

And I know that's something that you've been working on, and I'm a huge fan of it. But yeah, that's how we all came together 10 years ago. Well, and then I tell everybody the story that the way that we became very quickly friends over just business colleagues was my first international trip for business was Hong Kong, Singapore, Australia, and Tokyo. And I had never been to any of those places. And I remember we had one day. I had one day of training, and you had two days. And we were overlapping. And it was like, I only had one day of training in each one of those locations for a week. And they were a week apart. So I had like six, seven days to party in each one of those locations. I didn't know what the fuck I was doing.

And you had already been to all these places. And all of a sudden, we start ripping it up in Hong Kong, Singapore, Australia, and Tokyo. I was like, all right, fuck. All right, now it's cool. So anyways. That's a great way to build a deep-seated friendship early on. Yes, it is. A month in four different countries doing trainings and getting to know one another. Yeah. And so now, and talk to people, because now I think you have a unique perspective, right? Because you went from Google to Oracle to Salesforce. But now you're working with Emergence. And talk to people, because I think this is an important part of your perspective on these conversations is, first of all, what is Emergence? And what do you do specifically over at Emergence?

Yeah, yeah, totally. Which is perfectly relevant to your world, which is why we still get to partner together. So I'm a growth partner at Emergence Capital. We're a tier one early stage B2B SaaS investment firm. We just do A's and B's. We were the first investor in Salesforce and Box and Viva and Yammer and ServiceMax and Steelbrick and Zoom. So we just do B2B enterprise SaaS. And my job is largely, I would argue, one of the best jobs in the world in that I get to partner with companies once we choose to invest and help them on their whole go-to-market strategy. So I'm basically like free go-to-market consulting. And what I often see, you know, you're a million in revenue when you come to us and you're trying to get to 10 or 50 to 100 over the course of, you know, four or five, eight years.

And, you know, all the companies kind of struggle with some of the same things. Largely on the sales side in particular, it's like, all right, you know, I'm going from this inbound model where I get it because I was the shiny penny. I'm getting a ton of inbound leads with not too much marketing to, oh, we want to start moving up market and now we're going to shift to kind of going outbound. And, you know, and so, you know, I bring you in, I share a lot of insights. I'm like, hey, you know, when you're reaching out to these folks, even if it is inbound and you're reaching out to them, you're reaching back out to them, you got to have something to say. You got to have a point of view. And that's actually something I would, I would, so yesterday I was in an event with a bunch of serious baller enterprise sales leaders like Tom Addis, who used to be a box and salesperson people and the CIO of Napa Auto Parts.

And it was hilarious because he was talking about as a CIO, who has like a $500 million budget, the amount of emails and in-mails and, you know, hard mail that he actually gets. And he was actually highlighting, you know, just as a, from his point of view, what works and what doesn't work. And it was just a good reminder of a lot of the things that you and I have been talking about for years and that you anchor around, but there are some nuances now that I think in today's day and age that are even more important. And I think that's, and I, and I think you and I even separately, but now collectively are kind of beating this drum. Cause I was, I'm about to write a post on this as well, which is, you know, the difference, the rage has been personalization, right?

That's the why you, why you now email it's personalized, but it's getting bastardized to the point where these artificial intelligence tools. I mean, you saw me like a while back, like I freaked the fuck out in 2017 when I saw that Shakespeare email that wrote an email better than I'd ever seen. Right. And, but all of a sudden I'm seeing all these other artificial intelligence tools and they're, you know, they follow the formula. There's the why you, why you now they personalized the first part and then they kind of standardized the second part. But the problem is, is this is why I'm not afraid of them anymore. Like I, I literally was like Skynet's here was screwed, but I mean, seriously, but, but now I'm seeing that there's a disconnect, right?

Because what they'll do is they'll personalize that first part, but it's, they make it so irrelevant to the value proposition. It's, it's almost painful. Like you'll see something like, Oh, Hey, Doug, uh, I see you're in San Francisco, you know, goal warriors. And, but then it hard cuts to this, like, Oh, we're the leading provider of cool. I don't care. Exactly. And, and, and I was, I've told the story a couple of times on the podcast, but I think it's real. It's mostly relevant to this conversation, which like my boy, Scott McGregor, right over at edit, try something new. Now he is the CEO of his own company. So he's playing the very long game. So I understand what he did this, but, but this is also what happens.

Like the other, a little while when Charlotte was two, my daughter was two, right? Uh, I get this package in the mail and, and it's this book from Malcolm Mitchell, who's a new England Patriot, right? And it's a children's book and it's fucking signed by Malcolm Mitchell, right? And in, in there's a note from Scott saying, Hey John, I know you're, and by the way, I don't even remember how I knew Scott. I have no idea. I didn't know. I didn't really remember who he was. Um, and it's also, no, not at all. I mean, now we're great friends, right? But, but, uh, all of a sudden, you know, in the, in the notice said, Hey John, I know your daughter's around two years old right now. Cause I talk a lot about her, obviously he's like, which is a great time to be, be reading her bedtime stories.

And I know you're a huge Patriots fan. So I wanted to put this thing. I got this book signed by Malcolm Mitchell and I was just like, what the fuck? Like, this was like the most personalized gift I had ever gotten in my entire life. You know what I mean? Literally even more than my family. Okay. Yeah. Which was, so I gave him my time. Obviously I was like, dude, I don't know who you are. I don't want you need. But at the end of the day, like I was a one man show. I was not hiring at the time and he's a, they were, they were recruited, you know, they're a recruiter. So the relevance, even though he got a conversation and I, and so good for him. Right. But the relevance was zero. So I was like, dude, I appreciate this, but now I understand from his perspective why he did that.

Right. Cause he's a, he's an owner of his own company. He's playing the long game here. Okay. But the problem with that is, is if reps who aren't playing the long game, they're going to be in the SDR role for the next 30 days, the next, you know, three months or six months or whatever it is, or the eight, he's going to bounce to another role, like within a year, like that level of personalization doesn't matter. Yeah. I mean, maybe, maybe just one day when you move on in your career, that person will remember you and come here. Right. But I mean, if we, if we got a married short-term results, right. Yep. With building our brand and being relevant, it's, it's not about personalization. It's about relevance.

Yeah. So, yeah. So I'm on the kick now where personalization is, is overused. Just because you happen to know that you've got a two-year-old daughter doesn't mean that I actually want to engage and have a conversation with you. Just like if you know that I went to the university of Oregon or I'm a surfer or whatever it is, like there's got to be a connection. Right. So I always say, and again, this idea of personalization at scale is a total oxymoron because how can you actually do that? So for me, and part of what the CIO is talking about is it's about timing and relevance. So to your point, like the book itself and my, and here's the other thing too, if you believe that it takes eight to 10 touches for someone to actually get a response, part of it is, is like, what are you trying to do with that outreach?

Maybe if I'm Scott, I'm just trying to say, Hey, I'm here. Right. If, if, if you need to hire people or if you want to talk about it, maybe a different career, I'm here. So maybe that was his objective for sending that book. Um, I think a lot of times it feels like as a buyer, that's your objective. It's always just to get a meeting. Yeah. And part of what the CIO was saying yesterday, it's like, you know, share something interesting with me about my competitor. Um, you know, so it make it, make it relevant. And then I guess what, when the timing is right, if your message is relevant and the timing is right now, I'll engage. Right. So it's, it's, it's about timing and relevance. So can I ask on that?

Cause this is the part where I actually struggle with a little bit, which is, so first of all, I've, I've been talking about, it's the story, right? What's the story? What's the journey you're taking them on? And I make a lot of connections to like Gary Vee, jab, jab, jab, right hook. Like I've stopped doing the whole, let's get 15 minutes. Let's get 15 minutes. Let's get 15 minutes. First of all, for everybody out there listening, just stop asking for 15 minutes. Even the number 15 gets people to roll their eyes at this point. And I'm the offender of it. I'm the one who, you know, push that out there to everybody. You're the propagator of it all. I am. So, so my bad, like, let's stop now. It's old.

Um, but the, so you tell, do you talk about the journey and I agree with you? Like, Hey, I'm here. I just want to let you know, here's a little jab. Whatever it is. But what I struggle with is I don't, so I'm looking at you, Doug, your emergence capital. I know that I kind of looked at your LinkedIn profile. So I get a sense of what you're, what you do and who you focus on. Like, what kind of information can I send a guy like you that you're going to look at and go, Oh, versus some bullshit article that, that is like, okay, this kid, I see the kids, what the kid's trying to do. But again, going back to relevance, right? Right. Like, cause I tell people like, look, but, but every once in a while and I, and I'm actually just noticing us and I'm calling myself out on this.

Um, I noticed this on LinkedIn. I get a ton of people hitting me up. I get 200 in mails a week. Right. And, and, and a lot of people are, Hey, John, I thought this video was going to be really, you know, interesting to you. I thought, you know, here's, here's an article about this. And when I open it up, I'm like, eh, like, first of all, I look at it, I'm like, that just takes more time for me to fucking read. That takes me more time for me to watch. I don't have time for this bullshit from some sales rep who I don't know. But so I guess like, what, what, what are some of those things that we can put in there that would get somebody to pause and go, Oh, that's like, okay, that's a pretty good piece of content.

I'm not going to call the kid right now, but that was, that was worth me even opening and, and looking at for a few minutes here. Totally. Totally. I think one of the things you're describing is the difference between a fishing expedition, which is, I know a little bit about you, John, so I'm going to lob some things over that I think might be relevant to you and your world right now, right? A bit of a fishing expedition, but I would challenge people to actually go one or two steps deeper and understand kind of the business context of why I'm reaching out. Not just reaching out because yeah, I have, again, I'm going to go back to using Scott as an example and say Scott's a recruiter and maybe he can help you find employees as you're, as you're trying to expand, or maybe you have connections that you could pass onto them, right?

So, so if I'm Scott, my, my objective, and here's the, here's the key. I talk about this a lot when I'm, you know, when I do in my storytelling workshop, you got to have a point to your story, like stories suck if you don't have a point, because I have no idea where you're going with it. Same thing with your outreach. You have to have a point. What's my objective? If my objective is to get a meeting, then put yourself in their shoes and go, well, why would they want to meet with you? Because you think that you have something that could be interesting to them, but it has to be interesting to them and their business right now, what their businesses is experiencing. And so if you're, if you're going to do a fishing expedition, at least make it super relevant to their worlds, right?

So, um, Hey, here's some interesting information about your competitors. For example, I work in Emergence Capital. We're a tier one VC firm. You know, what would be interesting is because I, I, you know, I'm on what's called our platform team. Send me some information about other platform teams that tier one VC firms have, or given the fact that like you and I were students to the profession of the profession of sales, right? So, and we talk a lot about like, okay, what is sales 3.0? What's, what's the future of sales look like? And so maybe, maybe it's an article that, you know, from Harvard business review on, um, uh, we'll see, I'm just, I'm riffing right now, but maybe it is like, I hate like the new AI tools.

Well, but actually I was just trying to say that. I'm like, don't send me where AI has taken over sales because that's bullshit. I don't buy it, but maybe something to the effect of like, you know, uh, um, how, where the enterprise is going, right? So that's an interesting concept because every one of our companies, series A moving up into the enterprise, that's pretty relevant. I might actually take that and share that with our portfolio company, right? But then again, the question is, well, what do you want? Do you want a meeting for me? Which I highly, which is highly unlikely because I don't take meetings from vendors. If you're a vendor, don't ever send me a note ever again, because John knows I will not be very nice.

We send shit back and forth to one another about like, holy crap, did you see this? I'm like, send. And I say, take John's training, send. So every time I get one of those, I'm like, I love it when they come and try to pitch you like Salesforce stuff. Like that, that actually cracks me up. It's like when somebody, like they don't look at your background and realize that you fucking worked at Salesforce for years and that, you know, ran the enablement. So, um, it's so, yeah, but I guess like, so what's the balance? Cause I think like enterprise, right? Like I could justify spending an hour, you know, an hour reading through your 10 K and getting to know Doug Landis before I even go after Doug Landis, you know, and, and, and I think like that tool that I forget, and you can mention them here.

What was that tool again that, that, uh, for publicly traded companies, what's that? Databook. Databook, like where it just scrapes the internet for all the publicly information or now it's going to go private too. But, and it kind of gives you a sense of, Hey, what this company is really doing and the nuances. Right. So that's like superpower as far as insights, what, what they do is they identify that it's called this financial case for change. Right. Which is like, what are, so here's the thing. Every business has two or three strategic priorities, right? Every company has two or three strategic priorities and every, every division within the company will, it will, your objectives ladder up to one of those two or three initiatives, right?

Growth or innovation. Boom. If you're a big publicly traded company, it's growth or innovation. And so how do those businesses and a lot of businesses and ladder up to those initiatives and priorities and what are, what would be their financial reason that a CFO would actually sign off on, you know, a hundred, 200, 500, 5 million, $10 million deal with you. It's a financial case for change. And then when is your buying window? Cause guess what? You reached out to me in January and I typically don't start thinking about buying new technology until July. Yes. It doesn't matter. Like it's all going in the trash, right? And here's the other thing too. Actually, you mentioned 10K and 10Q. I just learned this yesterday.

This was bananas. So the 10K and 10Q are nice, but it actually doesn't really tell you what the risks are to the business, right? You have to really, I mean, it's really high level stuff. There's this, there's a report by every, every publicly traded company. I'm going to write about this on LinkedIn. It's called the DEF 14A. It is put out annually and it defines and tells you exactly what the real issues are of the business and how the executives in the company are measured and compensated. Shut the fuck up. What? Yes. Never heard of it before. It's called the DEF 14A. It's an annual report. Usually comes out once a year, right around the time when they're, they're putting out their, um, their, uh, financials as in DEF 14A.

It's a report. Holy shit. Only publicly available. One pager tells you their risks straight up and how each of the executives are measured and how they're calm. How come nobody knows about this? How come I don't know about this? How come you don't know about this? I just learned about this yesterday. So bananas. Yeah. They're doing this for 30 years and I just learned about this yesterday. Hold on a second. I got to fucking write, I got to write this down. Thanks to the guys at data book. Cause they, they, look, they compile all this and make it very useful, right? So that you can actually prioritize your activities. Cause here's the thing. If I have a list of accounts, right. And I know that, you know, of my 50 accounts, that 20 of these aren't going to be in a buying cycle until, you know, third quarter of the year.

Well, guess what? I'm going to change my focus to the ones that may be in a buying cycle in the next three to six months. Right. And now I've got also, I can have some more information from a relative. I've got a relevant perspective to reach out to them. Cause I know the risks and how they're measured. I know what's going on. You know, I want to find out what's going on with their competition. How do they stack rank against their competition? What changes are changing? Like that's the stuff that is relevant to a CIO, a VP of sales, a CFO. You know, these people that you're reaching out to, you want to be relevant. Yeah. It's important. Trust me. It's really important to know that, you know, if you're reaching out to somebody, if they're a vegetarian or not, so don't offer them a steak dinner.

If they're vegetarian, they're going to have to do some digging. Right. It's really important to know. By the way, the other thing that he said too, is that publicly traded companies, if you're trying to sell to them, most of the execs cannot accept a gift that's worth $50 or more. Makes sense. Right. So you're like, Hey, I want to give you these tickets to this Warriors game. They're like, cool. Can't accept it too expensive. Yep. Right. So it's these little things that you have to, you have to dig into and understand as you're reaching out. So I would argue in the future, we're actually going to be doing, we're going to slow down to speed up. Explain. Well, so think about that. Slowing down to me means you're going to put in a little bit more time and effort and thought into whatever you're sending to them, if it's an email, a phone call, a text message, email to make it more relevant about them.

Right. It's going to take a little bit more work. Sure. And, and, and to your point earlier, you know, to your point, um, on kind of, I'm going to call the Jay Barrels model 3.0, which I'm fucking blown away by. I think it's bad. Don't go offer, don't go aligning your entire solution to the one person you're reaching out to. Right. So especially like if you're Salesforce or, you know, even if you're box or you have more than one product, you need to align parts of your solution to them and the challenges that they have specifically, right. Versus like, Hey, we are the number one player that does this. You're like, Oh gosh, really? You know what? You know what the challenge. So, so for everybody listening here, the, the, the new messaging equation that we have is the persona.

And if you want to write this down, it's free fucking training, uh, persona plus the, plus, uh, the challenge priority of that persona, plus the component of your solution, plus the result equals the attention grabber. Right. So you can say, Hey, VPs of sales, whose main priority is reducing onboarding time, leverage our online training portal to get their reps ramped and produce the results immediately out of bootcamp. And I can call you up and say 50 times that, right. How do you get away with that though? Cause what, this is a little piece that I'm struggling with a little bit because I had this conversation, a rep brought it up the other day as far as not getting product centric, like, or feature centric.

Right. Cause that's the challenge with it is like, yes, we have this holistic solution, but if I were to call you and say, Hey, Doug, um, you know, our prospecting training is aligned with what you can do there. And you're like, yeah, we, it's all inbound leads for us, kid. Like fuck off. Right now. But now I'm like, but, but, but, but we have all this other stuff like, because you want to be specific. I mean, I wrote a blog post a while ago that I still recycle this day. It's called sell to the 20%, which is my fundamental belief that pick any product or service you own. You only use 10 to 20% of the functionality. So that's how you should sell, right? That's how people buy. Now, customer success is responsible for getting that other 80% there, but sales is that 20%.

But how do you get away with selling a component of your solution without compartmentalizing yourself about the solution itself, right? Swinging and missing. People just think you only do this one thing, right? So they put you in a bucket and they're like, Oh, you only do this one thing. Right. Right. Right. Totally. Well, listen, it kind of goes back to what's my point of reaching out. Yep. My point of reaching out is to connect with you, to engage with you, to, you know, um, deliver something that is relevant and timely, right? And overall, I'm doing all this so that I can get a conversation, right? And in that conversation, I'll explain, I might explain if it makes sense, how this fits into the broader spectrum, right?

Yep. Um, it's about contrast, right? I want to go, here's where you are today. Here's where you could be. Here's the way in which you can get there, right? Here's, it's kind of like your customer journey as we talked about before. Um, but if I, like when you bought your Tesla, whatever the X, it's got so many features that when you were there and you were, you were picking it up and they'd walk you through everything. Did you remember everything? No way. And so it's taking you time to learn the value of certain, you know, kind of certain capabilities of the car. It's the same thing when I'm buying software. I like, it's just, it's a strategy that I keep telling every company, help your buyers understand who you are and the values that you deliver in three steps, crawl with them, walk with them, run with them.

Yes. I want to show you what the panacea is. I want to show you what the promised land looks and feels like, like other customers, just like you or your competitors. But to get there, you're not going to, you're not going to eat the elephant all at one time. You're going to eat it one bite at a time. And so by, by mapping one component of your solution to them, you're not pigeonholing yourself. It's how you position it. It's like, this is one element or this is one step to help us help you get to this promised land. And so, you know, what's also so cool about that is, and it ties into what we had said earlier is, is it's a, to your point, what are we, what are we trying to accomplish with our outreach?

Okay. And if we take it as what, which my opinion is, I'm trying to take him on this journey. Obviously I want to be pinpoint with like, Ooh, like the best case, obviously, Hey, you said you needed this thing. I read about that and I got a solution for you. I'm going to tell you, I can solve that. That's rare. Right? So without knowing too much about you, I'm going to tell this story to you. That's going to consist of five, six, 10, whatever touches that's going to keep like slicing up components of my solution that all fit together. Right? Because I, what I tell reps is, look, there's two ways people tend to prospect, right? One is they do the generic elevator pitch and it's like, Hey, we do sales training, consulting for fortune 500 companies.

It guarantees the results you're looking for, whatever it says, right? And nobody gives a shit about that. Or we do, Hey, we do sales training, consulting, and we do prospecting, meeting execution, negotiation, objection, and closing. Like those are the five things I do. Right? And I could probably wrap a nice tight little message around that. Send a good email, voicemail, whatever. But say I send you that email, I leave you that voicemail and you don't respond. What's my next email? Yeah. Right, right, right. Totally. Yeah. Hey, it's me again. And to me, if you send me that email or that voicemail, I'm like, okay, overkill. I'm like, whoa. Right? However, if we know that in today's age, let's just say I work for a company and one of our competitors just raised a ton of money.

Right? And so you know that I will likely struggle in my sales conversations because that's going to come up often. Right? And so based on that, what you might anchor around is objection handling. Right, right. Right? So I would connect and be like, hey, listen, I know one of your competitors just raised a ton of money. My hunch is, I'm telling you, I know your business, that you're likely going to face more pushback from your prospects because your competitors now perceive as being, you know, maybe more advanced, right? We can help you by, you know, making sure that your reps are, you know, trained in terms of how to handle those objections. Psychology wise, let me ask you this one. Because I like, do you, do you, I like that one.

And this is why I want to dig into a little nuance of what you said, which is my hunches, right? This is your problem. What are your thoughts on saying somebody saying, hey, based on that, my hunches versus based on that, we've worked with other companies where that's happened. And this is how we've helped them. Like that, that small nuance there of me telling you, I think I can help you versus, hey, I saw that. And guess what? We've helped other people like that, that has happened with, and because these were the things they face. So is there a nuance there that you think makes a difference? I mean, it's, you're always going to be more, it's always more powerful if you say, listen, X company went through the exact same thing and we helped them.

Right. And so like, it sounds very, it sounds very similar to this other company that we were just working with that went through the exact same thing, competitor raised a bunch of money and they were able to block and tackle. Right. So it's way easier at the end of the day to take yourself out of the conversation and use the voice of your customers. Yep. Always a thousand times better and easier. Be careful about it though, because it's often overused and it's not used in the right way. Right. Saying like, you know, you know, like just name dropping for the sake of name dropping is total bullshit. And that's what ends up happening a lot with customer logos. It's like, Hey, well, we can help you just like we helped this company, this company, this company, this company.

So the nuance is to me with how you communicated is, you know, this reminds me of a similar situation with this company when their competitor raised a bunch of money and we worked with them to help them do X. And it has, there might be, I think there might be some parallels here. Yeah. And I think that to your point, the relevance of that story, you know, what really I've been thinking a lot about those stories too. And it's, you know, the before versus the after. Right. And, and, and I think there's a couple of examples out there that were used where, you know, you gotta, and I think you even said this, like you gotta get your, our first sale is to get people to agree that status quo is not okay.

Right. Like I got to shake you from this foundation that, that status quo is okay, because I can't sell you shit until I convince you that that, because I'm going to lose to no, no decision all day long. By the way, everyone's biggest competitor. Oh, all, oh, a hundred percent. Right. I mean like 95% of our competition is no decision. Right. Cause it's way easier to kind of stay muddling through this versus right. Um, but like, but I gotta get you to believe that the before is you, that, that I have experience with, with the before. Right. So, and that's why I think the really good, the analogy, um, is like the, the, um, Alcoholics Anonymous, right? It's like when you go to AA's website, you don't see somebody saying, Hey, I've been sober for 20 years and AA saved my family and my life.

Right. Like you don't see that. You see a guy standing up there, a woman standing up there going, it started with one drink and then I was missing my kid's soccer practice and then I was drinking at work. And then, and what it's doing is, it's like when you hit that website, you're going, fuck man, that's me. Like, that's me. And this goes back to that Chris Voss book, right? Like you want, you want somebody to say that's right versus you're right. Because me telling you, you have this, me telling you, you have a problem. Oh yeah. Yeah. You're right. I got a problem. I drink too much, whatever. But me explaining a situation and having you say, fuck man, that's right. That's me. Yeah. Now, now you're open to listening.

Well, at the end of the day, what you're talking about is empathy. Right. Right. You're empathizing. And the only way you can empathize is to say this, you know, this is why consultants are so good and they do, you know, a hundred million dollar deals. I was sitting next to somebody yesterday. He's got, he's, he's got an $8 billion number. That's ridiculous. Like bananas. He's got an $8 billion number to hit. And, um, you know, he does a hundred million dollar deals for breakfast. Crazy. Right. And, and what's interesting is, it's like, I, it's really hard for me to empathize. It's really hard for me to understand. I'm like, that's like, that's a lot of revenue. Like everyone around the table is like, okay, you win.

Dude, that's like the GDP of fucking France. You know what I mean? Like, no offense to our French fans. No, no, no. I love French. Um, so I think, you know, at the end of the day, the more, you know, and the more you understand, the more you can empathize. And it's really important to, to know that consultants use words like might and hunch, and they don't say you do and you have, right? So as I said before, my hunch is, you know, you're, you know, or you just remind me of a situation with this company and here was their scenario. Basically what you're doing is you want to build that narrative around that situation or that moment in time that you've chosen as your anchor point, right? Here's my point of the reason why I'm reaching out.

This is just like story time, right? I got a point and there's going to be some contrast. There's, here's how that, where that company was before. Here's where that company is afterwards, right? My hunch is, is you're experiencing, or you might be experiencing something similar. How do you have empathy without experience? So, so again, I think we're talking, right? Like you're talking enterprise, you're talking reps, you know, that billion, I'm guessing he's in his forties or fifties at least, you know what I mean? Like, like a solid 20 years of holy shit experience. I mean, I couldn't sell a billion dollar deal if it fucking punched me in the face. You know what I mean? Like I've never had that experience.

I'm not that smart. Um, so yeah, you're a 22 year old kid and reaching out to a 50 year old. And I, and I actually like, and this is, I also shit on social selling a little bit in this regard, because like talking about being thought leaders, like there are kids who are 22, 23, 24 years old, we're telling, Oh, build your brand and all this other stuff. And it's like, I'm, you know, one of my struggles is, is like you and I, we have it a little bit easier to build our brand in the sense that we, our audience for the most part, like, well, I'll take me for an example. Cause I sell to sales reps. I sell to VPs of sales. Right. So I'm like selling crack to crack heads and they fucking are dying for crack.

You know what I mean? So like, so for me to build my brand is, I don't want to say easy, but it's a hell of a lot easier. Okay. Cause I'm selling to my audience and I know my audience really well. And I am my audience. Right. Yeah, for sure. Whereas that 23, 24, 25 year old kid. Okay. I sell into a CISO. Right. I mean, first of all, brand building, fuck off brand building. I got to figure out how to talk to this person without embarrassing myself. But how do you, how do you empathize with, if you're that 25 year old kid, um, and you're calling into CISOs, you're calling into exec, you're being asked to call into it, right? Yep. And you're also being asked to hit a certain amount of metrics or dials or whatever it is so that you can get to your numbers and all that other stuff.

Like, how do you, how do you become empathetic to, to the people that you're reaching out to? So I've got, I've got two points in this. First of all, um, if you're an SDR, 22 year old kid, don't reach out to C-suite. I'm sorry. Just don't. It's just the truth. Do a draft on behalf. Uh, let me send it to my VP of sales to send to the C-suite. Even if I'm just using their email address, it can't come from you because they don't give a shit. Like you're just an SDR and it can, I can tell. I read messages when I look down and I'm like, Oh, BDR. I'm like, silly. I don't, I'm not going to talk to you. I don't have time for you and I don't mean to be an asshole, but that's just the reality. It's like, I want to talk to somebody who is in my mind, my peer.

They're going to bring value to me. The C-suite. Yeah. They're going to be, bring value because they have a level of understanding in my belief that will make our conversation more relevant. And so, so on the one hand, just be smart about that. If you're reaching out to C-suite, they're not going to respond. I'm just saying. So, so do a draft on behalf. But the other thing is you also, in order to build empathy, you have to understand them. In order to understand them, you have to put yourself in their shoes. In order to put yourself in their shoes, you've got to understand their business, how they make money, how they're measured. You know, how you're going to get, I got to understand core business acumen and have a business conversation, not a feature conversation and not a certainly a conversation about you.

And the problem that we found, again, I used to sit around the table yesterday with 10 baller enterprise sales leaders and the CIO, you know, he's got a $500 million budget. And the reality is, is like, unfortunately, a lot of people are terrible at having business conversations. They don't have the great business acumen to understand what is a 10K or a 10Q or, to be honest, the DEF 14A. You know, look, we're all guilty that we didn't even know about that. But the truth is, there's a language like EBITDA. Anybody know what EBITDA means and why it's important and who cares about EBITDA? FCS. Anybody know what that means? Now, again, I'm not saying as an SDR, you need to know that. But you need to understand it if you're reaching out to a business that you think is a good fit for your product, you need to understand why.

Why is that a good fit? So you want to hear... And that to me is how you can start to build empathy, right? The more you know and understand. Dude, have in your weekly team meetings or brown bag sessions, have one person get up there and just do like, I'm going to give you a breakdown of a company and this industry so we understand this industry inside and out and how they make money and where the competition is. Is the market growing? Who are their competitors? Are they coming from China? Are they coming from Europe? Like what's going on in this sector so that you know it and you can viscerally talk about it? Yeah. I mean, you want to do... I do this all the time. It's kind of embarrassing to the group, but here's something that you can have some fun with talking about business.

Because I actually just did a session yesterday, as a matter of fact, with the Bravado team on this exact topic, on business acumen, about how if there was one thing I wish I took more seriously and was more proactive about earlier in my career, it was business acumen, right? Yeah, I agree. Right. My business acumen was... You all can get better at it. Right. I mean, mine was a byproduct of my activity. I would just go, go, go, go, go, go, go. And I would ask a stupid question to a CEO and the CEO would say, that's a stupid question. And I would say, okay, I guess I won't ask that again. You know what I mean? But now, if I could go back, right, and I would learn about what these... I would read the job descriptions of these people.

I would try to seek out and not sell them, but try to seek out people in my network, maybe, that were in those roles and ask them, hey, I'm not trying to sell you shit. Could you just tell me what a day in the life looks like for you and what you're being held accountable for? Totally. And the way I know that business acumen is so sorely missing in sales, right, is I sit in front of technical... Like, I train teams who sell technical solutions to technical people, and I ask them, and I have this conversation about business acumen, and I say, okay, I'm going to prove a point here. Who in this room knows the difference between a CTO and a CIO? Oh, yeah. We've talked about this before. Everyone's got like...

Crickets. And I'm talking like senior, senior sales reps. And by the way, I'm going to put myself in this boat. You know how I learned this? At 35 years old, I was talking to a CTO, and the guy stopped me mid-conversation, and he goes, can I ask you, do you know what the difference is between a CTO and a CIO? And I fucking deer in headlights. I was just like... You're like, oh, good Lord. Why did you ask that question? I'm like, oh, come on. Really? You know what I mean? And I didn't have an answer. Yeah. And he was just like, you fucking sales reps all the time. You're talking to me about all this stuff that you think you know about, but you don't. So I don't think we need to know... So here's my little hack, right?

Because you know me. I don't read, right? I'm not a reader. Especially of books. I think books are fucking full of shit because there's like 80% fluff and 20% good. But I've read almost every business book there is because I use, you know, not Blinklist, but Get Abstract, where it's a five-page summary of every one of the business books, which is the key points and the key messages around that, right? And the reason I do that is because guys like you, executives, whoever, most of you all have read those books, right? And so I don't ever want to be in a conversation where I can't at least add value into the conversation based on something that you guys are talking about. So that's why I read enough about it, not to pretend like I know what I'm talking about, but to know enough so I can ask a contextual question.

Like you said earlier, and I couldn't agree more, that the only way that we're going to get anything of substance is to understand the top two or three initiatives and how our shit aligns, right? So I've always been a priority-based seller, but the problem is, is the way I used to get there is with the very lazy approach of saying, tell me about your priorities. Oh gosh. Right? Oh my gosh. Like you want to talk about the one biggest no-no in today's world of outreach or prospecting or whatever it may be? Don't ever ask that. What keeps you up at night? Oh my God. Yeah. My answer to that one is my, yeah, exactly. My answer is my daughter. Every time somebody asks me that question, I'm like, my daughter, fuck off.

Next question. It's true, right? So here's the thing, and this is really hard, but I challenge everybody that's listening to this, get really good at developing a point of view. And so you can have a point of view about their business and about the, you know, where the business is going and about how, you know, maybe how the market is, is, is impacting their business and what value actually means to them and how you can deliver value. But at the end of the day, at the point of view, it's also not set in stone and don't ever force it upon them. But you got, this is like when the more you know and understand about someone is the more you can build a point of view, right? Like, so the more that I know and understand about you and look, it's been 10 years and you just came out with this whole messaging matrix that, you know, you're going to be doing actually a workshop at Rev 2020 coming up here of a sales loss conference.

And it's like, I saw that when we were hanging out, watching the Super Bowl with Keanu Reeves. Awesome time. So cool. I still have, that fucking blows me away though. Yeah, totally. So I can still feel so many questions, but when you show that to me, I'm like, okay, this is, this is John Barrow's 3.0. It's like, this is the next, why you, why you now is super impactful five, seven, eight years ago. It's great. This is the next wave, which is, it's got to be super relevant. It has to be connected to my challenges. I have to be part of the solution, not the whole solution. And guess what? It is a, there's a, there's a vehicle for creating these messages because when you're using these, these tools, whether it's sales loss, outreach, or whatever else, maybe even Salesforce, it's, that's just a, to me, that's just a, a, like a, a holding tank, if you will.

And you need the information to put in there to actually start getting value. And so I, I hold everyone accountable for doing their level of homework to understand the right level of business acumen, especially around the products that you sell and the industries that you sell into and the people that you sell to. And then I, and then I hold it on the rest of your organization to help kind of build in that messaging that's relevant to them so that you've got the right vehicle, get away from this notion of why you, why you now. Yeah. And I, and I think some small hacks on that, uh, that I, that I do myself. And I actually, I'd like to, I'd like to hear your hacks for, for business acumen, right?

And what you, Doug Landis does, like what I do is, so Feedly, right? You know, Feedly, uh, RSS aggregator. I actually set up folders and Feedly for the stuff that I'm interested in, but also my audiences, right? So artificial intelligence and sales, that's something I want to stay on top of social selling, obviously sales blog, sales training, and then, you know, niche stuff like SAS, right? Cause that's mainly my industry. So what I do is I, I set up a, all those folders and Feedly, and then I go follow all the thought leaders who are way smarter than I am in those regions, in those areas and who are writing about it and all that other stuff. Right. I'll just Google like, uh, sales AI thought leaders, 2020, right.

And find like the top five or six people who are writing about it, put them in there. And that's my morning routine. So instead of like reading, you know, reading my fantasy leagues or getting all pissed off about that type of shit, those like, I'm just reading an article or two every morning, you know what I mean? Yeah. Yeah. And that's how I've been able to have better conversations, better insights, that type of stuff. Is there anything specific you do to stay on top of without, without it being like this big, heavy, Oh my God, I have to learn this thing. Right. Like in the plan for a test. We, we, we do the exact same thing. I do the exact same thing. I mean, my, my reading, uh, to your point about reading books, I love reading books.

I just don't read them as much. Cause I read, I read articles, blog posts. Um, you know, I, I, I listened to podcasts, like it's everything in the go-to-market domain. Now, the other thing is too, I'm also, because I'm an adventure world, I read about startups that are coming up. So, you know, uh, uh, fortune has some great, um, email. That come out every day about new companies that are getting funding crunch based is the same thing. So I'm looking at startups. I'm also looking at go-to-market strategies. Um, I'm looking at more specific sales strategies. I'm looking at marketing strategies. I'm looking at customer success. So I always have like 14 tabs open of articles that I want to read, which sucks when your laptop crashes, you know, cause then you got to read them all.

It's such a pain in the ass. Um, but you know, like corporate vision has great information around kind of messaging and positioning. Um, and they just launched a new book called the expansion fail. Don't need to read the whole book cause you can go on their blog and read more about kind of the ethos of that. Um, that's kind of one that I'm, I'm a big fan of largely because I think messaging and positioning, even to your point, your messaging matrix that you've created, it's so important because it's what you say and how you say it that actually gets somebody to respond. Um, I storytelling is my big, my big anchor for the year. Um, and this whole idea of how to build a narrative. Um, I'm actually writing a book about that.

Um, funny enough. Uh, but it's, it's, but the truth is, is like, it's a skillset that we all need to get better at, right? Just like it's a skillset building a point of view or learning how, you know, learning what the difference is between a CIO and CTO is, um, you know, we need to, we need to put the effort in. So yeah, I spent all my time reading blogs and, and, uh, and articles, not, not as many, not as many books. And I also talk to people like, so, you know, I talked to VCs and sales. I'm like, what are you thinking about these days? And, and like, so for example, you, you read articles on AI and sales, right? So what you're doing as you're reading those articles is you're building a point of view in your own head about where, you know, how AI will impact or could impact.

So that's all I'm saying you need to do. If you're calling on a company, let's say you're calling on a BPSL, you're build a point of view about AI and sales, because guess what? When I have, when I'm having a conversation with BPSL, I might ask him like, Hey, what's your point of view as like how AI is going to fit into your world? You could actually steal points of view. You totally can. I do this all the time, like sports radio. So like with the, you know, like here in Boston, obviously we do ridiculous sports, right? And there's like 15 talk radio and when like, that's how I stay up to date with my point of view on like the Patriots or the Celtics, the Red Sox is I'll listen to the guys who I respect and I like, and I'll be like, you know what?

That's a good fucking point. And then I will legitimately, like when I'm talking to my boys, I will regurgitate like that. Like it's my, like, I was the one who came up with the idea. I'd be like, Oh, did you see like the Kevin, you know, Kevin Garnett, they're having his, uh, his, uh, number retired as a, as a Celtic. And he was only here for five years. Um, but he won us a championship and there's a whole host of people who are like, fuck that, you know, blah, blah, blah. He was only here for five years. I'm like, no way. Now I personally have my point of view. I think he should, because he's in body's passion and he brought, you know, pride back to the city and all this other stuff. But it's like, I steal from other people and we all steal from other people.

Right. We totally do. So, so steal somebody else's point of view, but, but have one. I think that's, that's. Yeah. But also be able to back it up. Right. So if you're going to steal somebody else's point of view, like cool, Kevin Garnett or AI himself, but also have, you know, be able to back it up. Be like, listen, I was reading this article. I listened to, you know, uh, whatever the bench. Yeah. 95. Yeah. Exactly. Like I, you know, I, I was listening, I was reading, I was doing something and it gave me this insight and this is how I've got my point of view. And I'm curious as to what your point of view is too. Yeah. Um, yeah. Yeah. I just anchor around point of view, because when you have a point of view, by the way, it comes across in your prospecting messaging.

It comes across in your conversation. Um, you know, and largely look, that's what we're doing in the world of sales. We're just having a conversation to determine if it makes sense for us to have another one. Last question. Cause I've been asking this a lot. Can you teach genuine curiosity? I think you can teach curiosity. I think you can teach active listening. I think you can teach, uh, like, I don't, I don't think you can. Okay. And, and, and here's my point of view on this. I don't think you can because genuine curiosity comes from a place of giving a shit. I mean, caring deeply. And, and so I think, I think this in genuine curiosity comes across when it feels like this is rote. This is a machine.

You're just sitting out. You're just trying to hit a number. You're just trying to get a meeting. So you can check the box. You can get paid and move on. Right. To me, genuine curiosity shows that you actually cared. And so by doing that, you show that you actually put yourself in my shoes and understand and get a little bit to try and understand of me and my world. Right. That's genuine curiosity. And you either, you either have it or you don't. Now, what can help you get there is the fact that you may lose your job or you're not doing so well. So like, you know, morale, your morale is a little low and you're like, I need to, I need to up, I want to up my game. Need and want are very different.

The moment you feel like you need to do something or you have to do something by default as human beings, we want to resist it. Right. We just have a resistance to it. The moment we realize, you know what? I want to do this because I want to get better. I want to deliver a better experience. I want to take care of my customers because I love my company. I love my product. And I love, I understand. I love the value that we deliver. And I want to share that with you. I don't necessarily need anything in return. Right. It's that it's like, I want to share without the expectation of having to get something back. To me, that's real caring. So you just ended up my point of like, I tell people all this all the time.

And this is why I still as a 44 year old man who runs his own company and has 90, 95% of my business comes through inbound. I still prospect almost every day. And there's a reason for it is because I want to put myself in a position where I want your business. I don't need it. Because if I want your business, I sell the right way. I ask the right questions. I sell on your timeline. I push when is necessary. I get to power when I need to. When I need your business, I do some shady shit. You panic. Yeah. Like I give you the discount at the end of the month. You didn't even ask for, you know what I mean? I go over your head because I'm not a power fuck, right? Like that's if I need it. I want it, man.

I don't give a shit when you close, right? Yeah, yeah. It's true. Well, and also too, by the way, when you want it, you actually, you open yourself up to so much more creativity. Oh, way more. Right? It's amazing how much more creative you can get with that. Whether that's with your outreach or just you're building a point of view about something. Like it's incredible how creative you can get when you want something and it's deep inside of you versus you need it. Love it. Awesome, man. Well, as always, we went way over time as usual, but that's why we do this, right? So let's do this. Doug, what do you want to get out there these days? I know you said you're working on a book. Anything you want people to know about or how to connect with you or anything like that?

No, I mean, you can always find me on LinkedIn, you can find me on Twitter, although I tend to be on LinkedIn, Facebook more than I am on Twitter. I just can't keep up with the noise. But I am, this whole year right now is all about building in a narrative. So I'm writing a book called The Narrative and it's like how to tell your company products and personal story in a manner that actually gets people to care. And the reality is this narrative building is something that we do naturally, like you and I do it all the time. But it's like, how do we actually bring that into the workplace and how do we be more mindful about that? Even if it's around building a point of view or prospecting, whatever it may be.

So my draft should be out this summer and hopefully the book will be out in the fall for Dreamforce. And you said you're writing a post on this Def 14A thing? Yeah, so I'm going to write something on LinkedIn because I just learned about this yesterday. I'm going to do a little bit more research, but my friends over at Databook, these guys are, I mean, take prospecting to a whole nother level, take enterprise selling to a whole nother level, taught me about Def 14A. So I'll just send it out to everybody. Largely, actually, if you're ever selling in the enterprise, you need to know about Def 14A and then you have to understand the metrics and the language that align to every function in an organization, B Suite, all the way down to individual contributors.

And I'll post a little slide about that so you can go do your homework on all the language. And that right there is a hack to help you get better and build more understanding, which will get you to empathy. Do me a favor, tag me in that when you post that. Absolutely. All right. You got it. All right, brother. Thank you very much, as always. Always love the conversation. Let's grab another beer with Keanu next time we see each other. We'll be in March out here in San Francisco at Rev 2020. Giddy up. Yeah, actually, come to that. Rev to a little free promo here for Rev 2020. We're going to be out there, both Doug and I. It's going to be, what, March 9th, 10th, 11th out in San Francisco. I'm speaking of which, too.

If you liked this conversation and you're in the Midwest, come to the Sales Assembly Conference. I can't remember actually when it is, right? It's coming up. Actually, I think I have a link on it. Yeah, when is that? I don't know. It's June 17th. June 17th. June 17th in Chicago. And John and I are actually doing a keynote together. Yeah, that's going to be fun. You and I will be on stage together. And we're probably going to talk about some of these things that we just talked about today, right? Absolutely. what not to do and how to get better at doing what you do love it awesome well doug thank you and everybody hopefully you got as much value out of this conversation as i did um and like i say all the time even if you have a shitty day go make somebody smile because if you make somebody smile today you know you had a good day so uh let's try to make this world a little bit brighter as we go okay doug thank you all very much all right brother see you guys Thank you.