S4E40 - Navigating Change Management When Converting AE's to Outbound

Hey everybody, it is Richard Harris and I am not with my partner Scott Leese for the surf and sales podcast. He had something come up at the last minute and cannot join. We will be kind to him in his absence today. Super excited to talk to our good friend Jason Bay. I'll give you a more proper introduction in a second, but first want to give a shout out to the HubSpot company and the HubSpot podcast network they are really grasping and actually implementing on the AI side of the house. They have a ton of AI tools that are obviously tech related built into the CRM. Everything from doing research and pulling reports and helping analyze it to help write copy and craft things. And the cool thing about all this is that it actually can save you some time. You know, they can see that it's taking saving anywhere from one and a half to even four or five hours a day. I'm sorry, yeah, yeah, it does say four to five hours. Yeah, I'm reading my script. Sorry, but this is how we keep it Price. Jason, but imagine, even if it's just one hour a day, a lot of days in the year, what could you do to grow your business that way? Whether you're a marketing leader, sales leader, sales rep, an hour a day would be a lot, even if it means you get to shut down a little early and go spend time with friends or your family. So please check out our friends@HubSpot.com we do appreciate it. And without any further ado, I will introduce our good friend Jason Bay, who is the founder and CEO of Outbound Squad. He's on a mission to help reps and sales teams turn complete strangers into paying customers. A few of his clients include reps and sales teams from Zoom, cbre, Medallion, Xfinity Gong, and many more. Probably a direct competitor of mine, which we can go head to head on some stuff if we want. But Jason, welcome to the surf and sales podcast. Mine is Scott Leese.

It's good to be here. Yeah, I. Scott, maybe he just didn't want to talk to me today. I don't know what's going on with.

Him, but yeah, he's had to reschedule this like four times. So buck Scott for today.

All is good. Jason, you know how this rolls in reality. Tell people a little bit about Outbound Squad.

Do you go in and train the team? Do you do process stuff? Just give some people some context so as we dive into topics they understand where your frame of reference is.

Sure, yeah. So feel like there's a couple different aspects to People in our line of work and what they do. You mentioned process. There's people that say, hey, you use outreach or Salesloft or HubSpot or whatever tool you use, we'll help you figure out how to set it up and set up the process and that sort of stuff. So there's people that focus on tooling and process. I don't touch any of that kind of stuff on purpose. I really kind of hate dealing with all that kind of stuff. Mine is more around soft skills messaging. With prospecting specifically, it's how do I know who I should be reaching out to, what I should say to them. Do I have the soft skills to execute a great cold call? You know, the copywriting skills to write a great cold email. We also work with account executives on discovery demos, multi threading negotiation, and again, it's very much the way I would describe what we do is force management and command a message. I'm a huge fan of. It's how do you take all of the great messaging that they come up with and distill that down into questions that you might ask in a discovery call?

So we definitely compete head to head. So we might have to have a battle of wills today. Well, we'll each pick a topic and then give each other their art or how. How do we train around?

Sure, let's do it, man.

But I want to, I want to come back to one thing because I. I firmly believe. And again, similar to you talk about the soft skills. How do you define the soft skills as you see them with the people you work with?

Yeah, I think there's a couple things come to mind. I'm curious your experience too, because you've been in the game for. For longer than I have. I don't get the impression that most of the reps that I work with, I feel like most of them want to be good at their job. And I think there's a common misconception that the top performers aren't out there and they don't really care and that kind of stuff. I really believe that for the time that they're working, most sales reps, it's too hard of a job for people not to want to do really good at it. So what's the gap between, hey, I want to do good at my job and my team is giving me a little bit of an enablement and you know, I have some messaging and all that kind of stuff.

I think it's a couple of things, man. When we say soft skills, it's. There's a What do I say, how do I say it? Type of thing. And there's a lot of. I don't see a lot of the gap being bridged between. Here's our qualification framework. Medic. Let's say that we're using and how that actually gets executed throughout a sales process and in what order and how I should structure calls and that sort of stuff.

Stuff. Yep.

So the soft skills, I find, are really, really hard to teach when there's not a process in place where people.

Okay. Yeah. So I'm asking you, give me an example of a soft skill.

Well, the soft skill would be, hey, when I pick up the, when a prospect picks up the phone, what's my ability to, you know, do my intro? What do the first 60 seconds look like?

Right.

What's my tonality? What's my pace?

Right.

It's not only what I say, but how I say it. Totally kind of thing. It's your confidence. It's, it's all of those sort of intangible things that, yeah, frankly, are very hard to teach.

Yeah. You know, it's interesting. I see and say the same things that you're saying and, you know, in, in a different way in that, you know, you know, my phrase is, you know, teaching reps how to earn the right to ask the questions, which questions to ask and when. Yeah, like there's, there's not a revenue leader in the world who doesn't know exactly what that means. And they can pinpoint the reps on their team who need that help. For me, you know, I go into the psychology of decision making so they understand how buyers think about them. And more importantly, it's the part where, you know, managers and leaders don't, you know, they say, well, just do it this way, but they don't know how to explain why you do it that way. So I try to teach that piece. Right. But again, I'm like you, what are the questions? What's the flow of the call look like? How do you handle these things? Right. So, you know, like, another one for me is, you know, I, I, you know, we talk about objection handling all the time, and I, you know, I, I've reframed that. As, you know, we don't handle objections. Nobody wants to be handled. We need to marinate in them when they bring up an objection. I don't need to bring up a battle card and know what to say because of marketing or the competition. I need to spend time talking about it and marinate there. So to me, those things are what I call the soft skills. And equally important around that is helping them feel comfortable using those skills. Right. Which I think is. That's my summation of what I heard you say. I don't know if I'm, if you agree, but that's, that's how I define it. And I, I'm glad to hear. Because I want people to hear different opinions of this kind of stuff.

Yeah, no, totally. I like a really good example is like if we take a, a cold call, for example.

Gong's got some really interesting data on this. And I see the same thing when I listen to recordings. There's this belief, this old belief in sales that you have two ears and one mouth and you should use them proportionately. And I'm like, no, like a cold call in Gong's Data supports it's 55 talk time rep. 45% prospect.

Yep.

But if we step outside of the cold call, the way that I talk about soft skills is let's just talk about everyday life. If you're talking to a stranger and someone that doesn't know who you are, why would you expect them to drive the conversation? That seems like a really big ask. And in a cold call, you're talking to a stranger, you expect a really busy person to drive that conversation and do most of the talking. That's just not going to happen. I think like wrapping your head around like what are the parallels in everyday life? Yep, totally the parallels with cold calling. So that's, that's an example of it. So how do we drive a cold call? I'm a really big fan of permission based openers. I don't think there's any one special one that works in particular better than the others.

But. Pause, pause, pause. What's a provision? Cost opener. Defined provision based opener for those who don't know.

Yeah. So permission based opener is essentially the. So if you want to go around your talk track the. Starting with the why. Right. I really big on why, what how. So permission based opener. The reason why we want to do something like this is the definition of a cold call. My definition is any call that you make to someone that's not expecting it. It doesn't matter. I don't care if you spent 10 hours researching them, it's still a cold call.

Yes.

So when, when they pick up the call.

I think we could agree that 99% of prospects don't pick up cold calls on purpose. They think it's someone else. They're not just picking it up to see what salesperson has to say that day. So A really great way to get a conversation going is to ask if they'd like to participate in it, to get an opt in. That's essentially what a permission based opener is, is I'm allowing the prospect to have an opportunity to opt into this call.

Yep.

And typically when they say yes to this, and a classic one could be. Richard, it's Jason. I know I caught you in the middle of something. You got a minute for me to tell you the reason for my call.

You go in 80 to 90% of the time, you should get a yes. If your tonality, your pace, all that kind of stuff is good. And now I've got the Prospect's attention for 15, 20, 30 seconds.

Yep, yep.

And then the instinct here, and this is where we have to overcome.

Another kind of fundamental belief is that when we're speaking to someone that doesn't know who we are, we have to talk about ourselves first. And that just doesn't work when you're selling stuff. It doesn't work in communication. It doesn't work when you're trying to sell a belief as a leader, whatever it might be. We have to meet a prospect in their world and that's like a really big shift. If you say, hey, I'm going to meet my prospects in their world and add context in their world versus trying to bring them over here.

Yep, totally agree.

So with a permission based opener here, when you get a yes, what your instinct is going to be. And I hear reps at all kinds of companies, 95% of reps still do this. And it's a little tougher to get away with right now because the economic conditions is to pitch. Oh, hey Richard. So at Outbound Squad, thanks for taking my call. We do sales training for some really cool companies like X, Y and Z and yada yada yada. I'd like to set aside some time for us to talk about your team. Yeah, click right. You're going to get a lot of resistance, hang ups, that kind of stuff. And I recommend just doing the exact opposite. I call it a priority drop. So instead of talking about me, I'm going to say, Richard, I'm speaking with a lot of sales leaders right now and I hear a focus in one of two areas. One of them is around AE self sourcing. So they're having to get 4 to 5x pipeline coverage. AES need to do more prospecting and they're just having a heck of a time getting them to do that effectively. And the second thing is around running tighter sales cycles.

Yep.

So A lot more multi threading is needed right now. CFOs are getting engaged in deals. How do we get our reps to really run tight sales cycles? Multi thread. How does that compare to what you're working on and what you're seeing?

Totally agree with everything you said. I love it.

I'll correct myself. I thought you said a provision based opener, not permission based. So I for those who are like, did Richard say provision? Yeah, I did because I heard it wrong. But that's because I'm old and deaf. Yeah. But no big, no big deal. Jason, that's great. I love the fact that you're giving away some tactical practical tips. That's really good. You know, question for you.

Is it the rep's fault that their skills are so bad or is it their leadership's fault?

Well, I don't know whose fault it is, but I know whose responsibility it is.

Really good.

It's both people's responsibilities. I think that there's one camp on LinkedIn that's like, whoa, is rep. It's so hard to be a rep right now. I'm like, yeah, it is. But you also have money and there's lots of great coaching out there and there's lots of free content. Don't you wish, Richard, when you were getting into sales that there was all this free content on podcast and it's crazy right now. Yeah. And you can get courses for 100 bucks, couple hundred bucks, you could reach out to people on LinkedIn that post sales content. A lot of them will help you for free. Go blow up Richard's profile. He'll. He's got a lot of time these days, I hear, to help for. No kidding. The thing that the responsibilities of the rep, like you are responsible for your learning and if you're not getting it at your company, go find another company. Now on the other hand, when I go and work it with a company and I'm sure you see something very similar. It's.

Like as a sales leader and a leadership team, if you're not providing this stuff, how could you possibly expect a large group of people to be doing the thing they're supposed to be doing without you providing some structure? So yeah, it's both parties responsibilities.

I like that because I always like to lay blame because I'm just that jerk. Right. Hashtag, don't be a Richard. But I really appreciate it.

Do you see this is what I'm seeing this year. So it's late August 2023. I'm seeing a lot of companies obviously going through the layoffs in the tech sector we're in that we spend our most time in. And then they're even afraid to actually do anything. It used to be like, okay, recession's coming, we have to trim. We hate that. But now we got to go train who's here. This year it seems like we're cutting people, but we're not going to even try and help train them, you know, because we have to sit on our cash forever. But, you know, the beatings will continue until morale improves. Do you see that as well? Or, or do you see something different?

So hard because I'm a small sample size of, of one, but I'm seeing.

But so am I. You know, I still have, you know.

Yeah.

You know, I mean, are your inbounds going down like the rest of us who are in the business? Are your, you know, is most of your business coming from repeat customers who, you know, moved on or, you know, what do you think?

I think, I think it's been, it's been different through different periods of the year. So Q1 was almost no B2B business for me. Outside of existing clients, there's no new net business. Two of my clients had huge layoffs literally in the same week.

Right.

So announced in the same week. Q2, pipeline picked up in Q3. I'm. This will be our biggest month ever.

That's great.

This month. So I think that what I AM Seeing is two things. One, I'm seeing a lot of companies in the 100, 200, 300 plus rep range going outbound for the first time.

Yeah.

So they literally have hundreds of account executives that if they were doing outbound, it was out of their own volition. They've never formally done outbound before.

Yep, Yep.

Which could be a fun thing for us to talk about because there's a lot of mistakes that I see.

I actually do. I have a couple of questions around that since you brought it up.

Yeah, so I'm seeing that. And then the other half. Yeah, I'm totally seeing the opposite of that too. I mean, one of my longest standing customers, I just literally got an email from them two days ago. They want to cancel our contract. You know what I mean? So that fucking sucked. But. So I'm seeing both. But I am seeing a lot of like, we just made layoffs and our AES need to prospect more and like, we want to invest in them. But those are also companies that are actively looking like that. Those are the companies that would come in bad. You know what I mean? So it's hard for me to tell you what's happening with the other companies.

No, but that's fair. But that's the point. Right. Like, again, there's different perspectives on all this stuff, so. Well, I'm glad to hear that. I hope you have a provision that they have to pay 50% of the remaining balance in your contract. If not, I'll send you my contract verbiage.

Oh, yeah, we already had. All of it. Was pending. Yeah. Pending payments. It's like it's in the Internet. It's in the interwebs.

Yeah. Talk a little bit about what you brought up, though. There's this move to the full cycle rep. Right. And maybe even back to the full cycle rep like I originally came up.

Yeah.

What are the biggest challenges you see at a high level that a managers need to understand when they make this adjustment, or leaders, because it could be a founder or.

Let's talk about that first. But then what's. What do reps need to do to get their arms around this? Because so many of them moved into AE rules because they hated cold calling. So let's start with, man, like, what are the things a leader needs to understand? Got a team of 50 people, right? 10 people, whatever. Yeah. What percentage of those AES do you think are going to be like, all right, no problem. And what percentage are going to be like, okay, and what percentage would be.

Like, yeah, again, I'm with my existing clients. I'm seeing people do this well, and I'm seeing most of them not go about this in a very good way. So.

But what's their mindset going? So, yeah, you know, if you're going to coach a leader who's going to bring you on. Right. And let's say they got 20 reps, are you saying to them, hey, Richard, just so you know, based on my experience, this percentage of people are probably going to do this, this percent. Or even saying, hey, Richard, how many of these people do you think are going to really be on board versus who will go through the motions? Right.

Yeah.

Do you, you know what, do the leaders even get that or do they not?

I'll just. Let me speak to the situations that I'm seeing. I think it'll answer your question.

So no, they don't get it. But now you're going to try to not offend your clients, which is okay too.

Well, no, I mean, I have one client that I'm like, is very timid about it, which I think is bad, where it's like, hey, we're going to go Outbound. And you know that we talked about not doing this before because it's a bad thing and we don't want to bug our prospects and like, yeah, but we're going to do it now and we're going to roll it out over a couple months and do a lot of enablement and we don't even require you to record calls at first and all this other kind of garbage. And I'm like, that is not the way to do it.

Right.

What's going to happen when you do this? Like, let's just think about change. Change is really hard for most people and you're going to have. The thing you have to be willing to do is let go of people that are not hitting quota and then unwilling to do outbound. You have to let the be willing to let those people go. So go into it with that and set the expectation of what we're going to do, what's expected and be willing to let people go if they're not on board with that and they're not hitting quota. I think the second thing though is in terms of how you go about doing this, it's very classic things that you've seen a lot in your career. I'm sure if we're going to expect our reps to do this, the best thing that we can do is allow them to participate in the creation of the process of this so they feel ownership in it and then participate in with them.

Yep.

So the best sales teams I see is it's the old we called it rubbing shoulders back in the day. It's managers getting in the pit. And you know what you're going to do call sessions with your reps also you're going to call on these people and it's that urgency of I had a manager I was working with, I just love that he did this. He was doing a one on one with a rep and she's like, I haven't been able to get a hold of this, you know, contact center leader forever. He's like, what's his phone number? Let's call him right now. He calls the prospect, sets a meeting right there during their one on one with prospect and just like that's how shit gets done. Right. It's that urgency of like what are we waiting for? Let's just go make some shit happen. You know. So I think the getting in the pit bonus points if sales executives participate in that activity in some sort of way too. It could just be sending some emails, but nothing's more badass than a VP of sales, getting their hands dirty in enablement sessions and role playing, and then also picking up the phone one time a month and saying, you know what, you guys, I'm willing to do this too.

I'm gonna. I'm gonna. Yes. And you. Yes. And, you know, sort of in the soft skills world, right. What happens for the leaders is that their ability to be vulnerable, to get on the phone and take the same rejection or hear the same objection or get phone slammed. Just the fact that even if you get on a call as a leader or get on the phone and make 50 dials and you have the worst day ever, your team loves and respects you because you got vulnerable with them. Right. That's. That's an example. I think going back to our first topic of soft skills. Right. Like, so vulnerability. It's a soft skill. And again, it's got to come from the top down. Have you. This is the one thing I encourage people to do too, and maybe you do, is I would even have. I've encouraged VPs of sales and CROs to make some cool calls or do a sales call. It kind of depends.

Yeah.

And then send that gong recording to everybody and say, tear me down. What I miss. Yeah, right. Like, again, lead by that vulnerability.

Yeah.

Right.

So, yeah.

And then the other thing I'll do is, I'll suggest. And maybe you do this too is again, I love giving out tactics to people. I can tell you're writing these down, you're going to use them, so I'll send you a bill.

The other one is if a. If a VP or CRO gets on the phone and cold calls again, you got the whole territory. And who gets, you know, you know, in. In some ways, if you can, based on your territory alignments and those things, you know, you. Then spiff it out. Hey, I did this today. You get this account if you go do two cold calls and get an appointment or whatever. Right? So. So, hey, I'll be vulnerable. Y' all coach me on it. By the way, you get. Someone gets the reward right? In. In some way. So those are just different things I do to try and encourage. To your same point that leading with vulnerability, getting in the weeds with them. Because nothing will motivate your team more than you doing their job. Yep.

No, totally.

I cut off on something. What were you going to say?

The word that came to mind when you were sharing that was feedback. And I see so many sales cultures where people are too afraid to give feedback to their leaders, and that is the responsibility of the leader. Right. There to create an environment where people can give feedback. And what's the best way to do that is to take feedback in front of your team and take it well, receive it well. So that idea I love of I'm going to record myself making a cold call, send out to the team for feedback, and make sure to take the feedback well. Though, yes, invite the feedback doesn't mean you have to agree with the feedback, but show that you can take the feedback. So there's this component. If we're going outbound for the first time, we need to rub shoulders and we need to be willing to do the activity. The other thing that's super important too, is when we're rolling out new process like this, reps need to feel like they got to participate in the creation of the process. And that's not as complicated as it sounds. One of it is, if I got a team of 200 people, there's probably a dozen people on that team that, like, are pretty good at outbound and can do it. Why don't I get, like, a group of those people together? And this is the first thing I do when I work with a new company. We do a messaging workshop. We say, hey, what are you guys doing? What are you saying? Let's build out a messaging matrix for our top Personas. And let's get like, your talk tracks down and what do you do? Right. And then when we roll it out to the rest of the team, it's, hey, we're rolling out something that you guys got to create together, and we're asking for feedback on it. And it's this collective brain. They got to come up with what we do.

Participation so much higher. When I get to participate in the creation of it. The last thing I'll say on that too, is just like, when you're selling, you need internal champions.

Yep.

That's the biggest thing I see leaders completely neglect is they don't have those private conversations with Richard. Like, hey, Richard, you're crushing it. Do you mind if I, like, call on you during some of these calls? Do you mind sharing some examples in the Slack channel? Can you share a recording of you doing a call and handling an objection like, the champions need to come from within.

Yep.

And I don't want to sugarcoat it. Going outbound for the first time is very hard. What to do with an entire organ. This is extremely hard thing that will take multiple quarters of rolling it out to get it right.

Yep.

So those are kind of the big things. There's a lot of pitfalls I could share too, if you want to go into those.

No, no, I want to shift the topic in a minute because I feel like we're talking about ourselves a little much. I think we're giving good tactics, but it's like, hey, we're two sales trainers and we're so great. Of course we are, obviously. But, you know.

I agree. I call that the Grumpy Gus. Like, before I even sign contracts with people, I'm like, tell me, who's a grumpy of your 200? Who are the Grumpy Gusses? The one who are going to sit in the back of the room with their arms folded saying, I've been through every sales training ever in the world. Right.

Yeah.

I try to. To your exact same point. I try to get those people on board before the contract's even signed. I even, you know, I'm like, let's have a conversation with them so we understand and respect their experience. Right?

Yeah.

And then I don't do the. The messaging thing. I like that. That's pretty cool. We should talk offline about ideas where we could complement each other, if that's helpful.

Tell me when you know. So how long have you been doing the training stuff? How long have you been in the game? This as a consultant versus being a rep or an ICU or a leader?

I mean, I've been consulting for about 11 years now. Specifically with, like, outbounds. Last six or seven.

Got it.

Yeah. So specifically in B2B tech. Yeah.

What made you pull the trigger? What made you go from I'm cutting the cord from a regular job with security to doing my own thing?

Well, my first job as an adult was in 2008 as a freshman in college going door to door selling house painting services. So I ran a house painting company. So I never wanted to get into business or sales at all prior to that. And that sort of opened my eyes. I made $30,000 over the summer for school, so I was like this whole, like, running a business thing in sales. I really like that, you know? So, yeah, so I was a sales manager for them for three years, and I was a marketing director and got to do, like, sales training with them, all that kind of stuff. And I always had that itch to, like, really do my own thing. And I didn't pull the trigger until about 2013, and that was a really scary thing for me to do, I guess. 2012, 2013. And for me, honestly, the story is that my ex girlfriend in high school wanted to be a professional singer, and then she Moved down to Nashville to go pursue her dreams of being a country singer and got invited by like Gretchen Wilson or whoever it was. And I was like, she's fucking living her dreams out. Like, what am I doing? I've been talking about running a business for years and been too afraid to take the leap. So that's when I did it. I quit my job and I come from construction industry, so the first business I started was actually a construction business that primarily focused on residential repaints and reconstruction and that kind of thing. And it kind of didn't work out with my business partner. We closed a lot of work, but after that I was like, I've spent all of this time in sales and marketing. I want to get back into that training, running workshops, all that stuff I used to do as a sales manager, I want to get back into that. So it's been a kind of a long journey since then. But for me, I would rather. I'd rather make a quarter of what I make now working for myself than to go work for. I will never work for someone else again unless I. I don't know what would have to happen for that. But that's just.

Yeah, no, that's all good. So I'm gonna. Gonna pause here. I'm gonna pre ask you the next question, right. Since you've done this is, you know, but I got to go do the. The mid roll for HubSpot, as you know. But yeah.

What'S the difference? Is there a difference there really a difference about having SaaS sales experience versus construction sales experience? But don't answer yet. Let me go do my mid roll. Hey, you bring up. You still have your podcast, right? Yep. Yeah, we'll talk about that for sure too. But this one, as you know, I've got to bring up is Marco Berge and the Science of Scaling, which is also on the HubSpot podcast network. It is fabulous. It's great. If you don't know Mr. Robert, aside from being the founding CRO at HubSpot and a senior lecturer at Harvard Business School and the co founder of Stage 2 Capital, he's really just a nice guy. Like, he gets it. I've had several conversations with him. I've talked to him about mental health and sales, and he's a big proponent of things like that. But on his podcast, he really brings in the leaders who are running the organizations to share their secrets, which in my opinion also means where they failed so that we don't have to make those same mistakes. Strategies and tactics to scale your company Growth. So please be sure to check out the Science of scaling with Mark Roberge. But anyway, coming Back to you, Mr. Bay. Jason Bay.

What's the difference? Is there really a difference or is that just stupid stuff? People love to say.

Yeah, I mean, sales is sales to a certain extent. But I mean, I originally came from B2C land, which I don't think people realize how closely related B2C and B2B are.

Very, very close to the same thing. Obviously with B2B and larger deal sizes, you're selling to a business and there's multiple stakeholders and there's all of that kind of stuff. But having sat in both seats, I would say a lot of what I train and use because I sell every day and prospect every day. A lot of this is stuff I learned in 2008 and 2009.

I mean, so that's. So my question is, is there really a difference when someone puts on the job Description, you need SaaS sales experience.

Oh, that's garbage. So. And also putting that you need a four year degree. I, I dropped out of college, so I don't even qualify to become a sales rep in SaaS. You know what I mean? So it's, it's. I think all of that kind of stuff is absolute garbage.

That's hilarious. We've got another episode that says you don't need a college degree to be in sales.

It's so stupid.

Yeah, no, I'm glad you, I'm glad you sort of came down hard on that one.

Good. Well, I'm glad to hear that. To all the leaders, please stop pretending like it matters because it doesn't. Their ability to have a conversation, their ability to connect with people, their ability to be a human is the key to any sales as well as any relationship. Right. But you can't go through objection handling with your wife all the time. Right. Right. It just, it doesn't go well.

Yeah. She's the economic buyer.

We can do a whole episode of that. You know what, how spousal relationships are similar to sass or any relationship.

Yeah. My wife is that she's the toughest sale to.

Dude.

Yeah. I mean, it's got to be like I'm a very emotionally. I'm an emotional buyer. If I like the person, that goes a long way, she's not like that.

We got it. We got to work on your pitch to get you to surfing sales in November and December this year. So.

Yeah.

You haven't been yet. You need to come.

So going to, going to flip it here. What questions you want to ask. You know, normally Scott's here to help answer a question. If there's something I can help you with. A question you're curious about.

Question you. You posed this to me earlier, and I was thinking, because this is. You guys put the. The guest in the hot seat on your podcast in the opposite way, you know, as well, it's like, let's become the inner ear.

Did it feel like a hot seat in the first place?

Oh, I feel way more pressure having to ask you questions. No. One of the things, though, that I'm always curious about with, you know, not to age you. You've been in the game a lot longer than I have. You know, one of the things I'm always curious about is like, what have you seen in terms of, you know, last 10, 15 years, trends, anything like that in terms of sales, how it's changed, if at all? And then, like, what would you look at the. How do you think that's going to determine what the next 10, 15 years looks like? You know, kind of thing? I'm always just more. More macro viewpoint of everything that you've seen.

So there's a couple things I think the willingness of the people in the sales industry.

To learn has gotten way better, right? So I'm a Gen Xer. We never shared our tips and secrets, right? We're like, how'd you do that? I don't know. I just kind of talked to them and just sort of, you know, like there was that secretive mode. I didn't want to give up the secret sauce.

But that shifted. And I think you brought it up earlier. You know, as technology evolved and people had more access to get knowledge, those who wanted to could. Right?

You know, you didn't have to go to the library and search microfiche. You know, for most people are gonna be like, well, let's go Google it, everybody.

It basically is like Google, except you had to go to the library and look into a card catalog and then have to go down to the basement because they had to keep the microfiche down there anyway. The willingness of people to learn has gotten way better. Yeah, I think that's wonderful. I think the ability for them to learn on their own has gotten way better. I think the desire to get better is gotten better. I think leaders have gotten better at saying, yeah, I could outsource this and get help. I was the opposite of that leader. I was not the one. I was always afraid, if I hired a consultant like me or you, that, oh, my God, it's going to make me look weak because I don't know what I'm doing. And that's what I'm supposed to be doing, right? And that was a, you know, so. So I think that's gotten better. In some cases, there's still sort of the threat of it, but I think that's the biggest thing is, is just the willingness and ability to learn more has gotten better. I think, obviously the millennials came along and forced my generation, the Gen Xers, to make it better. And, you know, for all the complaining that people say, you know, they make about millennials, it's not the millennials fault, it's the Gen Xers fault. Gen X is very jealous of millennials. They're jealous of all the trophies, they're jealous of all the support and love that we didn't get because so many of us were latchkey kids figuring it out on our own. Like, I walked home from school at the age of 10, a mile each day, like a. That would never happen very much these days. And.

But I had to go fix my own snack and I had to call my mom and let her know I got home. But, you know, that's just the way it was. So I think Gen X is jealous of the millennials. So millennials listening. It's not your fault, I promise.

We're just bigger about it. Those are the big pieces. I think that through technology, the art and skill of selling.

Has changed and evolved and always will. Right? You know, you got to remember, I remember when sale, you could send your email through Salesforce. I remember, I look, I'm back in the day where emails didn't count for your metrics each day because you couldn't count how many emails you sent. Which is really ironic because guess what? Back in the day, emails were amazing. I'm talking 15 years ago, right? I'm talking like, you know, you got 30 or 40 or 50% open rate. You know, it was like getting a piece of mail in the mail.

So I think, you know, the technology has shifted us and will continue. I think, you know, moving forward, we're going to become better prompt engineers to use the AI the right way. We're going to learn how to ask the questions better, which to me reinforces what you and I teach anyway, of the skills of like, wait, that's not the answer I was looking for. I need to ask the question better, which, you know, of the computer, which then should translate into I need to ask the better question of the rep of the prospect of the customer. So those, those are the high Level things.

How do you, how do you stay connected with young sellers? So I'm sure you like me every year you do sales training. You're like, these reps seem to get younger and younger because the ages I work with tend to be in their mid to late 20s, early 30s maybe. And the SDRs absolutely are, you know, sometimes first out of college. And I'm only 34, so I'm that gen Y. You know, when I make a reference like Super Troopers or a movie I grew up watching, they're like, what the, what is this guy talking about? You know what I mean? How do you stay connected with just younger generation folks, if you think about that at all? So that when you're training. Oh, yeah, just your communication style, the references you use are very relevant to them because it's something my wife helps me out with a lot, but I'm a total boomer dude when it comes to this stuff.

So I, I, you know, I.

Continue with bad dad jokes. I make sure of it.

I try not to over tell my war stories. Nobody wants to hear that stuff from us, right? Unless they ask, hey, Richard, have you ever run into this and then kind of like you, I'd be like, yes, I have and I can answer that. Or are you running into it and you want me to answer it from that perspective? Right. Like, so I try to stay relevant to them. I do make, you know, I have, like, I've got an active listening exercise that I do and depending on the audience, like, I'll either do a Billy Joel tune because everybody knows the song Piano man, but. Or I'll go and pull a Taylor Swift or Beyonce song. And we run the exercise depending on the generation of that stuff.

So I am aware of those things and I Google a lot of stuff too.

In terms of.

What'S going on with these people. How are they seeing the world, what are they doing? And I try to bring that into the conversation.

You know, I think you and I both do a pretty good job on LinkedIn with the social stuff where, you know, we post stuff regularly. That's just good sales advice where, you know, our generational appearance may or may not shine through. Right?

Yeah.

So I think that's it. So I want them to research me and those kind of things. Those are the things I do. I worry about it a little bit. I don't worry about it a lot. I'm more interested in making sure that, you know, my customers, right. Their leaders understand that. I understand the pains that not only the leader has, but also what the Rep has. And to your point.

As part of my process I will always ask them, do you want me to talk to a couple of reps before?

That's such a good process.

And I think, yeah, and I think that's like the most.

So that's, you know, that's already in the funnel though. So I think the other stuff is, you know, just being relevant socially. Right. I'm not. So for, I'll ask you this. Are you tick tocking?

No. Yeah, see me, my wife uses tick tock so I like stay up on what people are doing and kind of what trends are and stuff like that. But I, I am a fan of no personal social media. I have zero personal social media. The only pro social I have is LinkedIn.

I go down that place too. Like where it's like, yeah, I haven't posted much on Facebook. You know, I'll do stuff on Instagram, I'll do a little bit of personal. But it's all the same. And the way I've looked at it is, you know, I have a professional brand. It's not a professional brand or a personal brand. It's a professional. It's both. Right. Work life balance. And so I, you know, I haven't strategized well how much this or how much that. But 95 of what I do is, is LinkedIn to your point? Because that's just, I'm gonna put time into this. That's where I want to put it. Right.

Yeah.

You know, so plus I've got teenagers, but I don't think they really need me like talking about them on social media right now. They don't, they're not happy.

Yeah, I got, I have one more question for you. Actually.

There's this. I think there's a revolution going on right now with sales enablement too, where.

Sales enablement was not too long ago. It was a lot of like certificates, completions of courses, like gong recordings of like did they mention our methodology stuff that we're asking them to do or not? And I am seeing a big trend and a lot of the data would support this too around more connection with like actual sales outcomes. And where I'm kind of going with the question is how do you think about like retention of the training? So when you're teaching something, the format of what you teach, the reinforcement of the teaching, the follow up, what role enablement plays, where the playbooks are stored, like all of that kind of stuff. Like I see a lot of organizations struggling with that piece and a lot of them acknowledging that they don't quite have it figured out.

Yeah.

But getting stuff to stick with reps, how do you, how do you think about that?

Well, that's where I upsell them to management training.

Yeah, it's all about the leaders, dude.

Right. It's like now there is, in my training program, there is a reinforcement automatically included that spend has a little bit of time with both the managers and the reps for a week or a couple of weeks after the actual training. Right. So that that connection can occur. And there is some enablement for me to make sure they know what they're doing as leaders, what to listen for, how to coach, what they're hearing, all that kind of stuff. So I think it starts there.

If it's beyond that, then it's, you know, they need someone to come in and help build that out. Right. Like, that's a playbook too. It doesn't necessarily have to be documented in the playbook format, but it, it's. It is. You know, if they're lacking that stuff, well, I'm not going to do it for free. Right. You know, you can find it, but that's how I approach it. So. But there is to that point, you know, with my training, you know, probably like, I don't know how you do it, but it's like there's a workbook and a handout, and if they want to record it, there's an option for them to do that so that they can go and use this stuff again. And then there's reinforcement stuff after the actual training to make sure they're sticking with it.

Beyond that, to your point, now, it is about their own accountability. Right. I've led them, you know, so I don't show up, throw up and leave that day. Right. Like, you know, it's not like Richard's here one day and he's gone. Like, there's tons of stuff. So that's how I see it. The enablement factor, I agree with you, is that, you know, to me, the certifications are around particularly early during onboarding. Is they're certified enough to get on the phone or to handle the calls? Right. If you're going to make it a certification in any way, shape or form, even without a certification, are they good enough? Right. Are they at 60%? Because it's very different for you to teach them how to have the competitor conversation, have them role play it, have them nail it. They're going to get it 70 to 80%. Right. The first time it comes up, they're going to get 100%. Right. The 10th time it comes up. So to me, it's. It's about that.

And figuring out where B plus is good enough to move forward to, then get them to the A. So that's how I see this enablement thing.

Yeah, no, totally. The leadership reinforcement is.

I can't believe that companies. It's just almost zero investment, even internally.

Like, how do you deliver coaching? Because most coaching from managers is delivered like this. Richard, you're not doing this thing. You need to start doing this thing.

Yep.

Got it. Cool. Awesome. Okay. I'm going to listen to it, or you tell me next time or don't even bring it up again. You know, there's just no. I think being a sales manager, there's a debate around the hardest job in sales all the time. I think sales managers got to be damn near at the top of the list. It's like, you get very little training. You take an immediate pay cut from being a rep. And a lot of the sales managers and SaaS that I've seen is at the large SaaS companies, 20 hours of their week is spent building reports and forecasts and gathering all.

Dude, we could do a whole episode on this. We could. We could do a whole episode on this.

You know, I. I agree with you 100. And yeah, they're not taught this. I. So I. I do have this program and I do. I run it for free a couple of times with. With Vidyard. I did one this week, actually, where we walk through these skills of how to train a manager to be a manager. Because you're right, we didn't get promoted for that. We got promoted for handling objections and closing deals. And maybe we helped with the interview process, and maybe we helped do some onboarding. It's like, oh, you want to be a manager, Right? There's nowhere. Did they talk about, what do you do when you have a rep who refuses to do something? Yeah. You know, what do you do, Jason, when you have an absentee issue and it's your best rep on the team, how do you handle it? Right. Like, nobody teaches you that until it's too late. Right. And how to prevent it. So I agree with you. So. All right, bud, we got to wrap it up. We went great on this. This was awesome. How can people get a hold of you, Mr. Bay?

Outboundsquad.com's the best place. So we got tons of free content there. So there's a place to find our LinkedIn content that I post on a daily basis. The Outbound Squad podcast and then we have programs for reps and teams as well. So if you're wanting any help in implementing some of the stuff we talked about today, Outbound Squad dot com. The awesome place to check us out. Yeah.

And you have a podcast as well, right?

Yep. Outbound Squad.

Yep. It is the Outbound Squad podcast. You're part of HubSpot, too, right?

No, not anymore.

Sorry.

For another time.

All right.

Beautiful. All right, Jason, it's good chatting with you and catching up with you, my man. Always here if you need me.

Yeah, you too.