Kushal: Hi there. Welcome to “On the Flip Side”, a podcast for anyone who wants to live their best sales life. We're going to be talking to buyers, sales managers, SDRs and AE's about things like, what does it take to be a great sales manager? Or how can you go home happy month after month? So let's dive right in. 

Hello, and welcome to “On the Flip Side” live with Wingman. I’m Kushal, and I will be your host today as we navigate the mostly blissful waters of prospecting with none other than Jason Bay. Jason is the outbound sales Coach and Trainer for B2B reps & sales teams. He's also the chief prospecting officer at Blissful Prospecting (now, Outbound Squad), and runs the advanced squad for reps who want to be great. Jason, welcome to the show. It's so great to be chatting with you again.

Jason Bay: Yeah, I just got done talking to Shruti before this, now I'm talking to you. It's a Wingman day for me. It sounds like that, sounds like…

Kushal: That sounds like good, like a good way to start off the day.

Jason Bay: Yeah, glad to be here.

Kushal: Great. Jason, just to begin with, you obviously play a lot of very different roles, professionally, personally, I'm sure as well. Of all of these different roles that you play, which one is maybe you know, your most favorite, which one do you really enjoy the most?

Jason Bay: This is actually something I think about a lot is, you know, my role as a business owner, my role as a sales professional, my role as a marketer in my business, you know, I wrestled for a long time with you know, do I identify more as a sales professional or a business owner and it's definitely a business owner. One thing I love about running a business is that I get to market which, I love doing marketing, I get to sell, which obviously, I love sales and prospecting, but I love being able to fulfill and get to like work with the clients too. So I really like my role as a business owner is what I enjoy most, it keeps it fresh. I don't spend too much time in any one of those three areas and that keeps it pretty fresh, you know, for me, so I love running a business. It's my favorite thing to do.

Kushal: That sounds amazing. Even though I'm sure with all of your clients and customers you must have a lot of very interesting stories to tell about sort of running that ship with a lot of different people, but we can keep that discussion for another day for sure. Coming back to prospecting, I know you say Blissful Prospecting. I love the metaphor and how it translates across you know, your business, your podcast, everything that you do. But prospecting, sales prospecting isn't always blissful. It can be stressful. It can be irritating, sometimes for prospects, sometimes for the reps, what would you really say or maybe your top three secrets to kind of keeping prospecting blissful, because you’ve been doing this a while and you've been teaching others?

Jason Bay: Yeah, I mean, I don't know if they’re secrets. But the way that I kind of look at it is I look at outbound as an equation. So I call this the outbound equation. So the number of quality meetings that you generate is a combination of volume, and it's a combination of quality. So if we look at that volume, times quality, I think, where people tend to over focus, and you need it, you need volume, but I think people tend to over focus on volume. Number of calls that you make, number of emails that you send out, they look for auto dialers, and there's nothing against an auto dialer, just, you know, that's not the only way to fix the problem of lack of quality meetings, I tend to focus more on the quality side of things. So on the quality side of the equation, there's really kind of three parts that if you do these, prospecting tends to get a little easier. So the first one is “Fit”. So am I reaching out to a good fit prospect in an acid test? And sort of the questions that I want to ask myself, as I'm working through my account lists are, what accounts can I speak to that represent a pocket within my group of accounts? Who has similarities that I can speak to in a very similar way? So an example of that would be working with a company that sells a customer experience solution, and they verticalized their sales team. So there's people selling into hospitality, which is very different than selling into insurance, it's the same solution, generating really similar outcomes, but very different language that I would talk to those individuals. So I want to think about in terms of fit on the account level, what best represents a good account for me? And where can I find similarities in that account? Where can I find similarities in the persona? So am I segmenting properly? That's the first part, so “Fit”. The second part is “Message”. So that's, what do I say? Where do I say it, all of that kind of stuff. And the big shift that you need to make here is you need to figure out how to talk about your solution from the context of the customer, and not from the context of view, the salesperson. So it needs to be more you-centric instead of me-centric. And I'm happy to provide examples, we can dig into that if you want but the message, each piece is a really big part. And then there's also your ability, like your “Delivery”. So we have fit, message, delivery is your soft skills. So when I get someone on the phone, am I really confident? Do I know how to speak to people all over the phone? Do I know how to write an email? How are my copywriting skills? So those three things make up the quality side of the equation. And prospecting, like I said, gets a lot easier when we take that volume, the fuel, and the rocket ship, and we put, am I reaching out to the right fit? Do I have a good message? And have I worked on the soft skills delivery? Those are the three things that we need to do.

Kushal: I think that's an incredibly amazing and simple way of really sort of breaking down the basics of what, you know, good prospecting looks like. Is anyone born with these skills, Jason? Are they sort of acquired over time? How much time do you think people really need to invest to really master these skills? Can someone pick them up in a couple of weeks, months? How does it look?

Jason Bay: I mean, it depends. Everyone's favorite answer. So I kind of look at this, like athletics. You know, someone like Michael Jordan obviously has just a very gifted individual that was very athletic. But he also needed that work ethic to be really good at what he did to write because everyone in the NBA is a hard worker. So that doesn't like, everyone's talented, excuse me. So it's like your raw talent doesn't become the differentiator. I think sales is the same way, there are certain qualities that, you know, if I'm naturally more empathetic due to my upbringing, that's gonna help me out in sales quite a bit. If I'm used to speaking to people and explaining things, because I have experienced doing that other areas of my life, that's gonna give me an advantage for sure. So I think there are people that have some of these innate qualities. But everyone, if you want to be an elite sales professional and sell large, mid-market, enterprise strategic type sales, you have to invest the time to get good at it. And I think where people tend to over index is on sales tactics and strategies in tooling and none of that stuff is bad, but where I would rather over index is, “do I really understand the people that I'm reaching out to?” 

So I have a client that sells, like I said, into, like, customer experience. So it's like digital experience is one of their personas, none of the people that I help have done that job before. So how do I learn what's really important to these people, what their priorities are, how they currently get the job done, the problems that they have, what's important to them, so that when I speak to them, I can speak in their language. That's where I would over index. If you spent most of your time learning that, the sales part is pretty simple, the prospecting part is pretty simple. Because I'm just going to talk to you through the context of what you care about. And I think that prospecting, especially cold calling, you guys have a lot of great data behind this, it's not about talking less as a percentage of talk time in a cold call than the prospect, it's about talking more about the prospect. That's the important part. In order to talk more about you as a prospect, I need to know your world, and understand what people like you tend to be focused on. And that comes back to the fit part that we talked about before. If I can reach out to people in like small clusters, I can speak to every VP of sales that I talked to in a very similar way, or every marketer that I talked to in a very similar way. I forget what your original question was, by the way.

Kushal: No, it was really about kind of the top secrets to keeping prospecting really blissful and you know, taking it from there. It sounds like you really have the science down on breaking up prospecting between, you know, the messaging, the tactics, the tools, all of those things. Given that sales isn't really taught institutionally in a lot of ways, it increasingly is being done in a lot of great schools, communities, etc. to just kind of learn sales, if you had to really set up, you know, a course on this, how would you really structure it? How would you run it, you know, tactics, messaging, tools? How would you really kind of go about structuring a course on this?

Jason Bay: It's such a great question. So I would talk through the way they'll answer this is, let's pretend the course is like a college course, or a high school course. Let's say it's to prep people that may not even know if they want to get into sales or not. So the way that I would structure a course like that is very similar to in my very first job. I worked for a company that… they were like a $35 Million company at the time, I think, and they taught college students how to run a house painting business. So that was my first sales job. I would go door to door in my small hometown of Brookings, Oregon, and I would knock on people's doors and sell them a paint job that was $2500 to sometimes up to $12,000. The thing that… when I went up through the ranks at that company I started with leading trainings and we would teach new college students 18, 19, 20 years old, maybe that didn't even want to get into sales, how to sell? The question we would always ask in front of the room is, what did you want to be when you grew up? In America, people say firemen and police officer, you know, whatever, astronauts. 

Kushal: No one says salesperson, I'm guessing.

Jason Bay: Exactly. Like, hey, no one said sales professional. Let's talk about what sales actually is. Me talking in front of you guys right now teaching you something that’s sales, when you guys got this job, the interview process you had to go through if you had to sell yourself that’s sales. So getting people to see that sales translates across multiple areas of their life that's interesting, right? That it’s going to have application whether people chose to pursue a career in sales or not, it's going to have that application. So I'm talking about what sales is and what sales is not. That's the very first thing that I would do to set the stage. And then we'll talk about mostly soft skills. What does it mean to talk less about yourself and more about the other person? That's a shift versus support response. So when you're talking to me, what is my ability to really engage and be genuinely interested in you and what you care about versus my agenda you know? How do I pay more attention to people's buying behaviors and what they respond to, what they don't like? That's all of the stuff that I would focus on first, basic, basic 100 level stuff before I ever taught anything, tactics. Just how do we understand how to be more compelling in our everyday lives to get what we want?

Kushal: Jason, you have any obviously trained a lot of folks, you've given a lot of advice, worked with a lot of salespeople on really their prospecting, selling all those techniques? Do you think people are really ready? Do they expect it to be this much and this type of work, but they're starting out? And do you think they would be ready to put in the work?

Jason Bay: So your question is for people just getting started, do they understand how much work it is? Another good question. I don't think that most people understand how much work it takes to be really good at anything in general, let alone sales. 

Kushal: That makes sense. 

Jason Bay: So I mean, the 10,000 hour rule by Malcolm Gladwell has been kind of debunked, but there's some definite logic there. And that deliberate practice is what it takes to be really good at a skill in sales. Just like marketing, just like playing basketball, it's a skill. It's a learnable skill. That's the coolest part about it. But one thing that people tend to have a really tough time doing is committing every day to practicing and getting better at something. That's the 1% rule, getting 1% better every day. I think that that's really hard for most people. So if you're unwilling to commit long term to getting good at sales, why are you in the profession is sort of always my question. Because it's one of the hardest professions you can be in. It's like the next closest thing, I think, to running a business, it's like you're in charge of your own destiny. Why do something that hard if you're not going to invest time to get better at it, where you're exponentially rewarded for having a better skill set? Like you're rewarded financially for that? How cool is that? But to answer your question, I don't think that most people understand how much it takes to be really proficient at this, like how many years it takes and, and the deliberate practice that needs to go into that to really be a world class sales professional, I don't think people really understand what goes into it.

Kushal: I think you made a really great point about really kind of improving maybe 1% every day. And that's something that applies to most things in life. Do you want to exercise? Do you want to get healthier? Do you want to get wiser, anything, you know, to get better at anything you sort of need to put in that work consistently. I think, however, as human beings, we seem to be wired to have an all or nothing sort of mentality, either to have everything go all out, or I won't do anything at all. So I guess maybe that's one of the, you know, stumbling blocks for a lot of us when we get started with learning something and typically even more so when things are sort of difficult. It becomes much easier when you have people sort of mentoring you along the way, sharing advice, guidance, being a supportive community. I think all of those things definitely help. And I think we owe it as people, you know, wherever we are in our journey to either help people who maybe don't know, things that we know, and also reach out to others and kind of try and upskill even as we grow professionally, which sort of takes me back to one of the points you made about, you know, when you started out you were selling paint jobs door to door right. I'm sure that must have been a great learning experience. What's maybe something that you wish someone had told you about selling and sales back then, that you kind of have found out the hard way yourself?

Jason Bay: Yeah, the thing I always come back to is like, I think it's two big things. One is adopting my own sales style. So the very first book I read was Little Red Book of Selling by Jeffrey Gitomer. And I'm a big Gitomer fan. And I feel like I was like channeling my inner Gitomer. And I did that a little too long. I think it's natural to do when you first learn how to do something to… even in basketball, I wanted to emulate Michael Jordan, of course, you know what I mean? So it's natural to want to emulate that. But I think stepping into your own style and being comfortable with who you are as a person, that probably just takes time. I don't know if I could have figured that out earlier. But one thing I do wish that I would have spent time on, and I learned this by going through therapy actually is that I didn't really actually… I was able to do the tactic of empathizing with someone, but I wasn't really having empathy for them. So I wasn't really sitting in the seat of the buyer and thinking about, “Oh, my sales team is struggling, I can't get them to pick up the phone, more land appointments, what might it feel like to be in that position?” You know, I didn't really think about that stuff until honestly, very recently, maybe two or three years ago. So I wasn't, people would say, you need more empathy in this email, or whatever might be. And I honestly didn't know what they were talking about. I was like, I don't really understand what that means. And I wish that I could have invested in learning that skill earlier. And again, maybe that's just maturity, maybe it's just I needed time to do that but that's one thing, I think that would have helped me a ton early on in my career all the way around.

Kushal: I think it's so important to really kind of pick up what's working, maybe get inspired by the greats and the best, and then kind of make something your own and add your own flavor to it, do your own research, do it in your own style. And this is across sales and marketing and everything else. The idea really at some point is to understand it, I think one of the biggest challenges facing sales, whether that's prospecting, marketing, again, whether that's reaching out to prospects, whatever it is, is that everyone's aspiring to be the same which is great. I mean, it's good to kind of, you know, be great at what you're doing. But I think it's really important in today's day and age to really stand out from what everyone else is doing. And the only way to do that really is to capitalize on yourself, really to kind of double down on what you think is unique really about you and that kind of bring that out. 

And I know a lot of people especially do talk about this in the context of prospecting, whether that's sending a cold email or you know, a cold call, or you know, a LinkedIn message. And even as a prospect honestly, I've… everyone receives messages, cold, you know, LinkedIn, etc, on different platforms. The messages that I think stand out the most or maybe lead to a long term conversation, maybe are those that are sort of personalized, individualized for something standing out. In one case, for instance, there were maybe three dogs on the corner in someone's room, when they were recording a message that stood out to me. It made that person seem different from everyone else, different and genuine. I feel like that's probably the key. 

So I think there's so much to be said about really bringing your whole authentic self. And like you said, so much to be said about empathy. Overall, I think that's a super key thing for everyone across sales, marketing, really across almost every function to kind of do more of. It almost feels like all of these things that make us better our sales are actually things that make us better people as well. It seems like a two for one might as well improve one skill, and you know get good at sales and at life in some sense.

Jason Bay: Yeah, 100%. One of my favorite quotes is from a guy named Michael Port. He said “Business problems are really personal problems in disguise”. And when I think about my own personal limitations, those have been the things that have held me back, career wise, you know, not being able to really sit and have empathy, not being able to, you know, have boundaries, you know, with people in my personal life and not having worked boundaries, you're… not asking for what I deserve, you know, not looking out for myself, I all of it totally translates you're totally nailed it.

Kushal: Yeah, I'm just going a little ahead, Jason. Everyone's, of course, talking about, you know, the economic slowdown, some signs of the recession, some more of the signs, the recession, all of those things sadly. Do you think something needs to change in the way that we're prospecting? Or do you think the basics remain the same? And I know you've talked about this in different places, which is great. But I think for us, that's really the question to ask. Like, is it business as usual for prospecting? Or, you know, from the signs that you're hearing from customers and prospects that you're reaching out to or your trained folks reaching out to, what does it sound like? Does it sound like people want sales reps to be changing their tone to be adapting or is it business as usual for most folks?

Jason Bay: Well, I mean, I've noticed this just recently, in the last couple of weeks that people are starting, sales leaders are starting to take the recession stuff more seriously because their prospects are starting to talk about it more. A couple of months ago, I was like, “Hey, you guys, this is coming. We don't know when, but we need to kind of be thinking about how we prepare our messaging for this”. So people are taking it more seriously, most of my clients, especially those that sell enterprise, they're selling to companies, those are the companies doing the layoffs. And so those are the ones impacted right now. In terms of the framework, the framework does not change. So that framework of volume times quality, I need to know fit, I need to know my message, and I need to be able to deliver, the delivery of that needs to be effective. Those three things don't change. The fit, you might adjust it, though, right, I did a webinar with Todd Caponi, and he's got a really just a lot of good stuff around this. But one of the things fit wise is I want to adjust my ideal client profiles. And I want to focus on industries that are least affected by this. 

So during COVID, you know, it was hospitality and travel and like, I'm gonna stay away from verticals like that. So think about, and you can find this on Google, just look at what industries tend to be most affected that you sell to right now and shift away from those and shift into the ones that are doing better. Right, so that's the fifth piece, the message piece, again, your message probably doesn't really change, I just need to lean really hard into a few things that prospects are really going to care about right now. One of those is reducing costs, and the other one is reducing risk. 

So I'll give you an example that customer experience solution that I talked about that one of my clients helps with. One of the really big value props they have is their solution will actually help their customers reduce their cost to serve their customers. So if I work in support, I'm a VP of support, one thing I really care about is the more people that call into our call center, the higher the cost is to serve our clients, that's the most costly thing someone could do is call us and for us to hop on the phone with them. So if they're not self-serving, we're losing money. So one of the things I'm really going to focus on when I'm talking to my prospects is how we can help them reduce their cost to serve, I should have already been doing that anyways. I should have already been leaning into that messaging. But that's like doubly important now. So I need to think about how does my solution fit into a business problem that someone is having, that a company is having during a recession, they want to reduce costs, reduce risk, I need to think about how my solution can do those things, and how we can help them do those things. So those are kind of the areas that we want to adjust. Fit and message are probably the two places that I would focus on the most right now. 

Kushal: Got it. And, Jason, just kind of to go back to maybe, you know, something that we spoke about a little earlier when you talked about, you know, the main things that kind of keep prospecting on track. What are maybe using the top 10 factors that really make your prospecting better, whether that's, you know, on the job, for instance, you know, fit and message which you just spoke about, and maybe you know, even off the job, for instance, you know, building up your network, which is not something you typically think of, you know, in a 9-5, not that sales, is a 9-5 job anymore, or any other job for that matter maybe. But what are maybe some of the most important things that you think are really part of the job and you know, not part of the job, in some sense, but you think are equally important to succeed in sales?

Jason Bay: Yeah, if we apply the 80-20 rule here, I think there's a few things that really have like the biggest effect. “Small hinges move big doors” is what one of my mentors would say. So I think some of those small hinges that I would be thinking about as, like I said earlier, any I'm going to over index on anything that helps me learn more about my prospects. So having dedicated time, every week, could be a half hour day, 15 minutes a day, or all I do is just consume information about my prospects. I'm listening to podcasts that they listen to, I'm attending webinars that they might attend, I'm downloading white papers, I'm doing all of the kinds of stuff that my prospects will be doing to educate themselves. That one has a huge return. The next thing that I'm going to look for is, there's huge, just immense value to having peers that you have relationships with and then mentors. One of the things I think I neglected for a really long time in my career is having a mentor or mentors. And this is not a formal relationship where I'm like, “Hey, Kushal, can you be my mentor?” It's not like that. Like this could just be someone that you look up to within your company, or that's written a sales book or whatever it might be, and just like reaching out to them and having a conversation with them and getting advice. It's been so helpful for me. And I think peers are really underrated too. You should be friends with the best reps at your company.

Kushal: Instead of always competing.

Jason Bay: Yeah, or a little accountability pot, or do you meet on a regular basis and you help each other. And those are some of the really big things. Another thing that I don't think people talk about a lot, and I'm not a personal finance expert and my giving finance advice right now, but having a runway, so important, having six to 12 months of cash, especially right now, where things are kind of volatile, to where you know, something happens if you don't hit quota for a couple months, or you heaven forbid you get laid off, like, you're going to be cool. 

There's something that it does to your mindset when you have a little bit of abundance, and there isn't so much pressure to hit your number this month, like financial pressure. So if you can have a little bit of a runway, I recommend it 12 months, that's what we do. But that's been an absolute game changer. I don't take on deals that are bad because we don't need the money right now. You know what I mean? I think that's super, super important. Especially through a recession, I don't want to have to make stupid decisions for money. “Quick money is bad money” is what I always say. So I want to put myself in a position where I can think several months ahead, a year ahead and think about what's best for me three to six months plus from now what's not best for me right now. So there's a couple of things that come to mind.

Kushal: I think those are some really great tips. And I think what they do is really move you to a position of financial independence in some sense. So that and professional independence to right with building a network, finding your mentors, bonding with your peers, learning from them, because all of these things really kind of give you a lot of freedom and give you a lot of leverage. I think otherwise, you know, you kind of lose out on and like you said, you end up making decisions for the short term that maybe aren't the best decisions for you. So I think all those make a lot of sense to do as a long term strategy. 

Jason Bay: Yeah. 

Kushal: Jason, I know I promised you 30 minutes, I know we're almost out. But before we go, we have a super fun segment coming up, which is my last segment. It's called wrong meanings only. What we're going to do is I'm going to throw three terms at you one after the other. And I want you to give me what you think is the wrong definition for each of these, are we ready for this?

Jason Bay: The wrong definition, okay, all right.

Kushal: Great. The first one here we go is “Outbound Sales”.

Jason Bay: It's just a numbers game.

Kushal: Okay, the next one is “Decision Makers”.

Jason Bay: There's only one.

Kushal: And here's the last one, “Revenue”.

Jason Bay: The wrong definition of revenue, money that hasn't hit the bank yet.

Kushal: Okay, I like all of those. I think those are super useful for us, Jason. Thanks so much. This has been an incredible 30 minutes with you. I hope you go on and have a great day ahead. And thanks so much for tuning in everyone else. 

Jason Bay: Yep, thanks everyone. See you.