Modern Training to Build Seller Confidence

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John Barrows: We’re going to try to dive into this pretty diverse panel here, so for those who don’t know, I’m John Barrows, JBarrows Consulting, I do sales training mostly, focused on techniques and stuff like that. I worked with Salesforce, LinkedIn, Box, Dropbox, a lot of those companies, so I’ve seen a lot of enablement departments working with them and we’ve got a fantastic group here.

Chris, you want to kind of kick off and just give a background in enablement, where you’re coming from, what the team structure looks like on your side?

Chris Orlob: Yeah, so I am the propeller head who runs product marketing over at Gong, and enablement rolls up into product marketing over at Gong, which I don’t think is totally unique, I think that happens with a bunch of organizations, but it seems to be less and less common today. My background is mostly in sales and sales management, few different SaaS companies, like I said today Gong, previously, and then a co-founder at a previous company.

JB: Cool.

Hillary Anderson: Hello, everyone, my name’s Hillary Anderson. I work for a company called Hired. I’ve been in sales enablement here for the last 16 months building out the program. We have a field of about 160 sales reps and I have been building out our program and infrastructure for sales enablement and training. We’ve been around for about six years.

Gopkiran Rao: John, thanks. Gopkiran Rao, I go by Gop, or as I was just telling Hillary, rhymes with rope or dope, depending on my performance this morning. I’m SVP of strategy at MindTickle, which on any given day is an expansive role or an expanding role. I oversee most of our go-to-market. I’ve been in and out of enablement for the last 18 or 19 years, working with a variety of front office automation vendors, working with sales teams ranging from a few dozen to several hundred across a variety of industries and certainly have a practitioner’s but also a recipient’s point of view on the opportunity or the problem.

JB: Cool. I actually wanted to flip it over to everybody else here, just a survey of the room here, how many of you all are in enablement, or some training or enablement? How many in sales just out of curiosity, anybody? Alright cool, so it’s mostly enablement. For those of us in enablement, how many of you are on the one person show that’s running around like a chicken with your head cut off doing everything, how many one-person shows do we have? Alright, how many are on a team of five or less, just out of curiosity there? And how many five or more? Alright, so actually a pretty solid mix here. Cool, we’re going to try to address all of it, coming from an experience level and also working with the clients, we work with all of them. I’m actually going to start, Gop, with you – little bit more experience, a little bit of the grey beard, same with me. Talk about training and how it’s changed a little bit because I’m going to lead us into confidence, but how it’s changed over the years and why it’s changed over the years. I’ll kind of put some context on this question as it relates to buyer knowledge. The buyer has a lot more knowledge – the technology that’s out there, obviously, and then just from a generational standpoint. So in the past 15, 20 years that you’ve been doing this, have you seen a major shift and was there a significant or has there been a graduation, just out of curiosity for me?

GR: That’s a great multi-dimensional question, John. I’m coming from two perspectives. The first one is – just sort of take a step back and ask, what is the point of sales? In fact, as a seller, I always have a deal with full fundamental questions and I think for enablement professionals it’s particularly important to dwell on these questions. The first one is why this problem space? In my case right now it’s why sales enablement? The second question is why my company? In my case right now, it’s why MindTickle? The third question is why now? And the fourth question is why pay this much? It’s a question about value. As a seller, whether I’m being trained or coached or being taught, these are the four questions that materially impact my livelihood and then relate to the KPIs and the metrics that I’m measured by, whether those metrics are activity metrics; how many opportunities have I logged; how long did they sit in any particular stage whether it’s in Salesforce or dynamics; what kind of quote conversion do I have; what kind of win-loss am I showing and ultimately hitting my quota, a.k.a. quota attainment.

If I take that fundamental concept in terms of what keeps me up at night, what wakes me up in the morning, now I can think about training in that context. I think training has evolved depending on the industry you’re in. I think high complexity, low-velocity industries – industrial manufacturing, insurance, health care, and life sciences – there’s been more of a tendency to think about training in the context of bringing people out of the field and putting them in front of an instructor. That’s been typically the prominence of large training firms, technology vendors, the LMSs of the world. It’s all about imparting boatloads of information, shoehorning it into someone’s head, and hoping that the retention continues beyond. And it continues delivery of training, it’s very high touch, it’s low fidelity but high touch training. Then you’ve got a whole class of high velocity, low complexity industries where it’s really about pushing product out, sometimes through partners, sometimes through direct channels. And that’s where e-learning I think really emerged through the last 10, 15 years. The idea was: can we take a lot of that content that we’ve built, using our custom tailors whether they’re internal or outsourced, and move it into modalities, delivery platforms, where I can pull as opposed to having it pushed to me.

I think that in turn has led to a new generation with the advent of AI, machine learning, mobile, just-in-time, just enough technologies of which we – in particular at Gong, etc., aspire to be part of, which is how can we now personalize and adapt not just learning but also training. So, it’s a little bit of a mixed response to your question, but I think really it’s about the context. The context of the individual, the context of the company, and the context of the industry.

JB: Chris, I’m going to throw this over to you for data. I know by the way if anyone’s not following Gong’s blog, please follow Gong’s blog. is one of my favorites – I’m not trying to promote anything but this is legit one of the best blogs I’ve ever read in my life. But one of the things I’m going to throw over here is, look, as buyer knowledge has increased, it feels like seller confidence has decreased. Are you seeing any of those trends with the millions of calls that you’re seeing? I mean, you compare top sales reps to average sales reps and obviously, confidence has a lot to do with that. But what are you seeing from that standpoint and how do we combat it a little bit?

CO: For anybody that’s not familiar with the type of research we put out, we analyze sales conversations with AI and unpack what the best salespeople are actually doing according to data and not necessarily intuition. This actually relates pretty well because what we’ve found is that the highest performing sellers talk extensively more about buyer-related problems and topics that kind of get looped up underneath the buyer rather than the seller or the product. I think the way that relates to the topic at hand, especially like how all of this has evolved over the last few years, and how the topics of training have evolved is, historically speaking, I don’t know about sales enablement but I know product marketing has historically had a profit and loss responsibility. What is intuitive to a product marketer or a sales enabler to ensure a high P&L is to stuff the sellers with as much product information as they can.

That has worked – that worked 20 years ago, that worked 30 years ago because sellers held the cards, everything was close to their chest, and buyers did not have the luxury of being able to perform a Google search and find this all out on their own. I’m sure everybody in here has already heard this message before, but what works today in training is not what is intuitive, which would be stuffing the sellers’ lips with product information, but helping them understand the buyer and the detailed nuances of that. What are their pain points, what objections come up, and when throughout the sales cycle? Tying that back to confidence, I would actually argue that’s the number one piece of information that you can equip a seller with to skyrocket their confidence.

JB: What is the number one thing?

CO: Equipping sellers with a very deep level of your buyers. Because if you know your buyer persona, or if you don’t buy into personas, just the market you sell to, it almost doesn’t matter what words you’re saying. I mean, it does matter but that’s a cosmetic issue. If you understand the buyer at a very deep level, the right words come out automatically and that’s where confidence –

JB: And this kind of leads to Hillary. From a journey standpoint, getting a new kid on board and all the way through, one of the things I’ve seen is somebody asked me, “John, you’re 42, if you could go back and tell your 22-year-old self something, what would it be?” You know, a couple of answers. One of them was business acumen; I’d be a lot more proactive with my business acumen because my business acumen used to be a byproduct of my activity. I would be meeting with a CEO and I would ask a stupid question to the CEO and the CEO would say, “that’s a stupid question.” And I’d say, “okay, won’t ask that again.” I’d be a lot more proactive with it.

So talk about: what are you doing right now to help onboard reps and build confidence along the way so that they can have those conversations?

HA: I think the one thing that Chris hit on is our buyers now have access to that information, and if our salespeople aren’t enabled with that information as well and know where to find it and how to find it, how to access it quickly, they’re going to go into conversations with their customers and not be prepared and therefore lose their rapport. We all know that rapport is such a big piece of selling.

We need to make sure that we’re delivering content and information and tools and training in ways that are both digestible and accessible to all different types of learners, all different types of levels. For me, one of the things that I have to think about when I’m building our programs is that we have sales teams globally distributed. They’re used to obtaining information in a variety of different ways and we have our new hires start, we have individuals who are fresh out of college, they might have limited sales experience, all the way up to someone who may have 15 years of sales experience. So how do we allow our sales field to collaborate and apply the information that we’re teaching them so that they can, rather than just regurgitate it, actually apply it?

I like to think about our new hire training program as providing our field with a toolkit and not only telling them what’s in the toolkit, but telling them what tool helps in what situation and helping them map so that they can actually go out into the field and handle these different situations and be able to apply and therefore continuously learn. Then over their growth as a salesperson, they’re able to continuously learn and develop so that rather than just regurgitating, they’re actually applying and retaining.

JB: What’s the kind of combo of product knowledge versus skills knowledge from an onboarding standpoint? Because I think the historical – Gop, you said it – the historical is to stuff product knowledge down their throat, let them out into the field, maybe give them some skills and good luck, and actually, I think the more you know about the product, the worse you are at selling. That’s why sales engineers are sales engineers, not sales reps, because sales engineers talk too much about stuff that they know too much about. It’s actually better in my opinion for sales reps to know just enough to be dangerous. Do you have a mix that you introduce that and kind of scale that through?

HA: I think when you think about training, we think about the initial intake of a new hire, that initial week where we’re trying to make sure that we give them the information that they need so that when they go to their functional training with either their team or however your company has it structured, that they have that base knowledge and can start applying it. Because what product knowledge a customer success manager might need is going to be very different than what an account executive needs. It just depends on your organizational structure and your product kit, like how extensive or how limited are the products that you sell?

I think the way we currently structure it is I make sure that all new sales hires are aware of the products that we have, but we’re not going deep into the intricacies of those products. One, because I think we want them to retain it, but if you go deep into the weeds, only so much is going to be retained initially. An education of what exists and then an ongoing check-in and application based off of their functional role and based off of what they’re going to be working with on a day-to-day basis. I think if I were to kind of split it up between sales specific training and getting them up and running versus product knowledge in their initial 30 days, I probably would put it at a 70/30 split. 30% being product knowledge because you know they’re going to start using that ongoing and that’s going to develop, and then the 70% being the actual application and selling.

JB: Nice. And Gop, what are you seeing, because you’re obviously using the platform? A lot of people use it differently, but the best organizations you’re seeing from a scale standpoint, how are they introducing product and skills along the way as they map out that journey?

GR: That’s a great question. We are quite fortunate to work with customers around the world that look at a platform for readiness and enablement from a couple of perspectives, like one is, “do I think big, start small, scale fast?” and that corresponds to the classical crawl, walk, run strategy that IT vendors like to tell prospective customers about. Then there are others who look at it in the context of the average seller is working with seven platforms, he’s working with 32 different content sources, he’s got six or seven experts that he’s supposed to work with from moving towards more of a team-based model. There’s more team-based buying going on, regulations are changing, so let’s go pick one problem and solve it really well.

I’m going to take a step back and look at human behavior. No two sellers are the same. Some of the data we capture, for example, tells us when certain kinds of sellers are more likely to engage with learning versus skilling versus assessments versus quizzing, for example. We start seeing an interesting probability distribution across our customers. I would say about a third are focused on events, major SKOs, major expansion of sales teams, an impending acquisition, launch of a new product line. There’s a specific set of activity that you have to drive new sellers, sellers that are sort of in the middle of the distribution, and sellers who are mature, through those events to get to a very defined outcome. The chief commercial officer of a pharma company cares about share of voice. That’s measured in the number of calls you make to a doctor and the number of samples you hand out, the number of coupons that get picked up. Then you’ve got someone who’s looking at bringing a mature sales team to the next level in terms of you have all of the real characteristics because they’ve been doing this for a long time. What you need now are the industry-specific skills and then you have to take it to stand and deliver, which is what Dan was talking about previously. So now, you take a step back and say, “what is the single measure of capability, a.k.a. the revenue productivity power of my organization?” Then you start making decisions around what kind of training, what kind of learning, what kind of technology I’m going to be investing in and when.

It’s a little bit of a roundabout way of answering your question, but I think fundamentally it comes down to those four dimensions that I think are the elements, tools that HR and folks have been thinking about for a long time. These are skill, product knowledge, competitive knowledge, company knowledge, knowledge about my values – which is the discovery, storytelling, objection handling, and ultimately how do I measurably demonstrate this in the field and how does it tie to the metrics I care about as a seller?

JB: I was going to say, Chris, can you measure confidence outside of results? Can you actually see confidence? Because as I was talking about, there’s this moment in every sales rep’s career that I call “catching your sales groove”, where you wake up one day and it’s just a little bit easier than it was the day before. You don’t know really what happens and the best analogy I have for this is for anybody out there who wants to – my favorite sales movie of all time, by the way – and anybody who says Wolf of Wall Street, Boiler Room, or Glengarry Glen Ross are the great sales movies, they’re the worst sales movies I’ve ever seen. I mean, great movies, worst sales movies. You want to see fantastic sales movies, go watch The Pursuit of Happyness, fantastic. My first favorite one, though, is Tommy Boy, so there’s a homework assignment for everybody tonight, by the way.

There’s a scene in Tommy Boy where he catches his sales groove – you all remember where he catches his sales groove? “Helen – you look like a Helen – let me tell you why I suck as a sales rep.” Say you’re going to some guy’s office, he isn’t remotely interested in buying something from you and he goes through this whole ridiculous thing and at the end she’s like, “wow, you’re twisted, I’ll go fire up those wings.” At that moment, he caught his sales groove, because before that he was trying to be his dad. “You could stick your head up a butcher’s ass,” but no, that’s not how you sell, right? Then after he catches his groove, he saves the town, so you could see it happen. That’s why I love that scene and I always look for that. There is a point but I never know when that is or what happened. Can you see it based on what you’re listening to? I mean both internally and with the data that you see but also internally with your reps.

CO: I don’t think you can measure that with data. I think it is an anecdotal thing that you as a human – that AI cannot do – you see that click. I think one of the best ways to make that happen is spelling out or demonstrating to your sales reps what good looks like in each selling scenario that they’re going to encounter. From a broader level, you can define these selling scenarios as the conversations that they’re going to be having throughout the sales process from the first call to close. Discovery, demo, negotiation – what does the broad 30 to 60-minute call look like when done well?

But there are also micro-selling scenarios within each of those conversations. There are objections, there are responses to answers to a particular discovery call. I think when you have the power to demonstrate to sellers, especially new sellers, what does good actually look, sound and feel like in each of those selling scenarios, you see this “finding your sales groove” accelerate. I’ve seen it happen at Gong. I’ve seen some of our greener reps start out and you listen to some of their discovery calls and it’s just a trainwreck. It’s like they get kicked in the teeth because they ask the most generic line of questioning that they possibly could, they dump every piece of product information they can during the demo, and God forbid, come to a negotiation, they drop their pants before they’re even asked to drop their pants. But not when you equip them to understand what is good. Get John and me in a panel, you’re going to get some inappropriate things eventually.

HA: We’re just going to skip that.

CO: But when you equip them to understand what those scenarios each sound like done very well, you see that learning curve really accelerate. That’s what we’ve done really well as far as onboarding at Gong.

HA: Can I add something?

JB: Yeah, I was going to say, Hillary, do you see it?

HA: Yeah. I think the other thing to account for too is: what is good and how does that change for each person? I think it’s important to give them an example, to your point, of what a strong call is, what a strong discovery is, what a strong demo is, etc. But I think that everyone has a different ceiling because it’s subjective. There isn’t data that you can map to the confidence. But one way that we try to get a pulse as to where they’re lying on that confidence radar that doesn’t exist, like I just said, is putting them in situations that are similar to what they’re going to experience in the field with our internal employees. So, we’ll unexpectedly say, “hey, you need to go pitch to our head of HR and see what she says” – it’s our own product, right? Or we put them in front of people at our company that they don’t have exposure to yet to see what panic alarms go off for them, what do they stumble through, what are they doing well? We get a gauge as to where they’re at when we intake them, when they’re new, and then where they’re at three weeks from there, and just constantly kind of benchmarking for each individual, rather than just saying holistically that everyone should be able to crush this aspect of the call or crush this aspect of the demo, but recognizing you’ve got people in different markets. You’ve got people with different levels of skills, and we can’t map everyone to the same confidence marker. But we want to start mapping them to themselves and see where they can go and grow, etc.

JB: Gop, did you want to add anything to that?

GR: You know, with respect, I would say data is the single most important thing that you can capture.

JB: As it relates to confidence and measuring it?

GR: Yes. I think I would even say the role of enablement should actually be to inform even your recruiters that what goes into your ATS tools should come out of the knowledge that you’re capturing on your best sellers because if you think about the role of enablement, it’s really about empowerment. How do you empower people? A) you hire A players. In some cases you can’t do that – just being a little bit controversial here. If you can’t hire A players then you pick your best A players and you surround them with attention. One way to do that, in addition to putting incentive programs in place, is you surround them with coaches. These coaches don’t have to be just frontline managers, they can be peers as John was talking about earlier. They can be experts in other fields within the organization. You can wrap them with more team-based selling, etc.

Then, you invest in them with the best possible tools. You don’t add more tools, you bring down the number of tools, the number of destinations they need to go to. But you put best practices in there together with changed management. Then you start thinking about the journey of the seller from the point they’re HR-onboarded to knowledge onboarding through skilling, through assessment, remediation, development, expertise, mastery. That’s the entire line. You need to be collecting data on your sellers at every single stage of that life cycle and every single interaction they have with learning, with training, with coaching, with assessments, with readiness, through to delivery. That’s the data that needs to go back into the next generation of sellers you bring into the organization. If you can’t do that in a very measurable way – and I think you’re absolutely on point in terms of capability measurements – you’re doing yourself a disservice, the professional a disservice, and frankly a company disservice. This is my holy grail. I think you have to be able to reduce sellers to as much of a quantitative framework based on skill or whatever the appropriate framework is. I think a number of us in the room have points of view that we need to be talking about as a community on this particular topic.

JB: Alright, so I’m going to kind of flip this over and say I think that’s in an ideal world where we all have all the money in the world, we can all invest in the best tools and those technologies. What about those of us who are self-funded, no money, scraping and clawing – how the hell am I going to measure that type of stuff? Is it an Excel spreadsheet? You also talked about management. Yes, ideal managers are the ones who coach and all that other stuff, but nine times out of 10, managers don’t have the time to coach, even though it’s the most important thing that they could do. They don’t have time to do it. How can you build a framework to allow for, where do you start? What are the most important things to measure early on and how would you do that? Forget about the technology for a minute. Thoughts?

HA: My other question is how do you balance revenue production versus soft skill and hard skill? Ability, especially. Is that by ways of questionnaires, is that by ways of testing, how do you do that?

GR: I don’t want to be self-serving and speak about the technology, but let’s definitely have an offline conversation about that. I’d love to share what some of our customers do. I’d love to have an offline conversation with anyone who’s interested. I think it’s a great question and it boils down to an answer in three parts. One is there’s a process issue. How do I tie the process of readiness, learning, teaching, and training through the process of the sales process, which is opportunity management, opportunity progression, deal cycle management, through to revenue processes, collections, renewals, upsell, cross-sell? Those are the core processes.

The second piece is the people. How do I tie together people who are in different selling functions, from telemarketing to business development to inside sales to field sales to strategic accounts to global accounts to enterprise accounts, through customer success to support through billing through AP or AR? Connect all those people, that’s the second piece.

The third piece is the tools piece, and I think all too often we get hung up on the tools piece. This needs to be done in CRM, this needs to be done in marketing automation, this needs to be done in Gainsight or some other customer success tool, this needs to happen in CPQ – which is your quote, win-loss information, etc. – or it needs to happen in an execution tool, a content management tool or potentially a training platform. I think if you take a holistic point of view, the tool piece can be solved through integration. It won’t be easy, I’ll give you that. It’s really about driving correlation between an earned capability a.k.a. the skill well framework. This says for me, as an enterprise seller, it’s important to have three parts of discovery, four parts of objection handling and five parts of being able to position my product if I’m an AWS seller against Microsoft.

What computes out of that is an index. That index is my sales readiness index. And now I can take that sales readiness index and I can work with someone in finance or potentially sales op or deal desk to say, “what are the three most important KPIs of revenue predictability?” He’s probably going to say it’s opportunity aging, it’s the number of opportunities converted, and it’s quote win-loss. Now, I can take those and I can take sellers with the highest ROI or a high SCI and look at their appropriate quote-to-cash characteristics, and patterns start emerging. Then I look at the next level down which is the number of calls being made, the number of calls that are converting into a sales qualified lead, the number of demos done, the number of onsite meetings, and now we start seeing a second layer of conversion, of correlation. So, there’s work to be done. I think there are very well-thinking people here, John included, you, I, that really should be thinking more about this at the next level in terms of that end-to-end framework. Then you start thinking about where to put the content and the training and the learning in there.

JB: I’ve always looked at it as a quality-quantity issue. When somebody was onboarding, I figured out the equation: how many dials, how many meetings, how many proposals. I knew that was a pure metrics thing and I would stuff the kid and say, “do that, just do that for the first couple of months, because until you do that I can’t tell whether it’s a quality or a quantity issue.” Do the quantity first, give you crappy leads, make a few phone calls, don’t get the good ones, and then if you hit those numbers and that equation isn’t mapping out, now we can pull down and say here’s the individual skills.

Hillary, I want to go back to something you said which I thought was interesting and then I’m going to flip it back to you guys so any questions you all have, please, we’re going to leave the majority of the rest of the time. But not yet, I’ve got one more. I loved what you said as far as involving the sales reps, getting them to do things internally, leveraging resources, because reps would always have a challenge.

They’ll say, “Hey, John, I’m having a challenge getting through gatekeepers,” and I’d be like “Okay, Shelly, are you a gatekeeper?” Our gatekeeper says, “Yes, John.” “Do you get cold calls from sales reps all day long?” “Yes, John.” “Do you mind talking to Bill here about how to get through a gatekeeper?” “Sure, John.” You know what I mean, it’s like, leverage your resources.

“I can’t talk to CFOs.” “Calvin, are you a CFO?” “Yeah, John.” “Can you talk to one of my reps about how to sell to a CFO?”

HA: And then you get confidence.

JB: Right?

HA: It’s practice. Practice makes perfect. Those of you that are athletes, I’m sure that you know this. Until you’ve done something once, very few people feel confident in their ability to do it a second time.

JB: And what’s the difference between practice and roleplay? Because I like to roleplay, it’s a nice comfortable environment, but who has done really well? Roleplay is kind of bullshit.

HA: It’s like baseball or basketball.

JB: Sorry.

HA: I think you’re right, there is a differentiation between the two but you think about again, a sports analogy, which is so typical. You’re a basketball player, you shoot free throws even though you won’t do that for the entirety of the game, you scrimmage with your team half court, you scrimmage with your team full court and then you condition. Training for sales is similar. There are things you need to do in a repetitive nature so that it’s, to your point, like second nature. So you talked about just quantitative “hit the phones”, repetition to know that that’s the motion, which is like your free throws I guess, and then you think about what needs to happen in terms of fine tweaking the things that might not be as natural. So for those BDRs, for those SDRs, we need to get them in front of the people that they’re already afraid to talk to. And not roleplay, but practice. Then when we want them to fine tune that practice, perhaps a roleplay.

JB: Chris, are you–

CO: Yeah, I think there’s a lot of value in practice because I think it initially builds some of the muscle memory that they’re going to have to deploy in the field. But I will say this: I think a lot of sales enablement and just sales organizations as a whole are pretty gun-shy about letting their new sellers actually get into the field and get their teeth kicked in because you can give the perfect demo in a practice environment or a roleplay environment. Once you actually get in front of somebody, that’s where the real learning is going to happen. And if you keep deferring that first call, that first discovery call, or that first demo into the future, really what you’re doing is you are deferring that person’s time to full quota. There’s a little bit of sacrifice that goes on here, you don’t want to give them the lead that’s like the CEO of a Fortune 500.

JB: The best leads. So I was going to say, how do you do that?

CO: For the record, I don’t think you should give them the worst leads either. That’s not necessarily representative of what they’re going to be dealing with. If I sell to B2B sales organizations and I give my new seller a farmer, that just doesn’t represent our target market. It’s not really a learning experience – but maybe somebody who’s not 100% on our ideal customer profile but maybe 70 or 80% of the way there. So there’s a little bit of a give and take. I’d argue that being less gun-shy about getting your new sellers on the phone or on the web conferencing platform a little bit sooner can be a tremendous opportunity if you balance it with not giving them the COO of a Fortune 500 lead.

JB: Alright, just to finish up: one actionable quick tip that everybody could do to build confidence, rapid fire. I’ll give one to start with so you guys can think about this. I’m not throwing it on you, because I didn’t prepare any of these questions today, by the way. But one of them is, caller confidence, get four people in a room with a speakerphone and do round robin dials on a speakerphone. You will see confidence go up on the phone immediately because one person makes a cold call, they screw up, they get hung up on – the next person won’t do that, they do something different. The next person picks up on it. You do an hour call blitz with a defined list, with a defined thing, and everybody crushes it and walks out of there.

I used to do contests with my team, four people in this room, four people in this room, whoever got the most meetings, the other team had to buy them beer. Whoever had the biggest trainwreck – I used to have a trainwreck medallion – so whoever had the worst trainwreck call I’d be like, “Hey, congratulations with the trainwreck.” Just have some fun with it, realize we’re selling stuff, we’re not brain surgeons here, you know what I mean? That would be my tip of something actionable you can do to help build confidence right out of the gate. Anybody else?

CO: I’ve actually got two, and one I’m kind of stealing from you. First of all, educate your new sellers very deeply about your buyer personas, but instead of making that just a one-way monologue, make your sellers go do the research and then give you a presentation about these buyer personas. What do they care about, what are their objections? And then the second quick tip, I would just say, be less gun-shy about giving your reps a live environment.

JB: Love it. Hillary?

HA: Well, now I’m going to kind of steal like you stole. I say create a fail-safe environment. You’d much rather your sellers fail and have that bad call and have that uncomfortable experience internally than when they are customer-facing, but also allow them to know that when the trainwreck calls happen, it’s okay, that’s how we learn. We remember the things that go poorly much more often than we remember the things that go well. So, use your internal team to help replicate the buying process, have them get in front of the CFO, have them get in front of your CMO, have them get in front of your CEO, pitch the product and hear the objections. Sell your product to your company so that they can have that relationship, have that access, but be in an environment where they can fail and feel comfortable failing.

GR: That’s a great tip. I’d say make your customers your coaches. You’d be surprised how many customers would be willing to take an invitation from you to come in and spend time with your sellers because the only thing that they hate more than their time being wasted is actually wasting a seller’s time. So, it’s a win-win here, where you can almost come in and do a workshop with them and have them just listen to pitches and give you feedback on how your sellers can improve.

JB: And actually, I’m going to bring that around to have your new hires call into existing customers and ask them, why did you buy, why do you stay with us. Those stories that those reps learn from those customers, first of all, hopefully, you’ll gather information from a customer success standpoint, there might be some things that they uncover there, but then all that translates to confidence over the phone when making a call so the reps can say, “Hey, I was just talking to one of our customers, and they said before using our stuff they were doing this and now they’re doing this. You fit a similar profile, I’d love to chat with you about it.” So, you go through an interview process for existing customers. I love that one. Cool. Alright, let’s flip it around to questions that you guys have.

Host: If you have a question, raise your hand. I’m going to come around with the mic. We’re going to try to get as many questions done in the next 10 or so minutes, so if you have a question, think about if there’s a specific panelist that you want to ask it to. So if you have a question, please raise your hand.

Audience 1: Hello, first I just want to say thanks to everyone for coming, this has been really great. So we just touched on something about being gun-shy about getting new reps in front of clients. I agree that sometimes you’ve got to let them tread water a little bit. So in those environments, where you’re like, “we’re going to see if you can swim a little bit,” as a manager on a call with the rep, how long do you let them flounder before you jump in? And what is the appropriate ratio, because clearly you don’t want to lose deals but they need to struggle a little bit, so I’m interested in your perspective on that.

CO: I think that that is a judgment that you learn over time. I don’t think I could give you a perfect ratio where it’s like let them talk for 68.2% of the call and you for the rest.

JB: Come on, man, what’s with the data? Right, seriously?

CO: Everybody thinks that I have data behind everything I say. Very often that’s not the case. I would say if you ride along on enough calls, if you shadow enough calls, or if you listen to enough call recordings, you start to get the sense of when you should jump in. I will say this: I think most managers are a little bit too aggressive about jumping in, and they should kind of let their sales rep hang out to dry so to speak, like these scenarios where they kind of have to figure it out for themselves. I wish I had a better answer for you. I don’t. Hopefully that helps.

JB: To chime in real quick, what I would do is structure the call. I wrote a blog post a while ago called “Executives are like children, they need structure.” Without structure, they tend to take over. If anybody’s ever done a ride along with a manager, if there’s no structure to that call, within five minutes of that call, the manager’s in. But if you set the stage of, “Hey, you know what, let’s graduate you through this process. Why don’t you do the intro to the call and ask a few of the questions, and then I’m going to take it from there.” And then you say, “Okay, now you do the intro, you ask some questions, and then you present this, but then I’m going to close it out.” You know what I mean? So without that structure, it’s going to be a disaster because then managers will just jump in whenever, wherever, when they feel comfortable because it’s like, “Oh there’s an opportunity, shut up, my turn, you missed it.” But if they know when they’re supposed to talk, and the rep does too, it’ll be a lot more comfortable.

CO: We’re going to pretend that I gave you that answer.

HA: I think it’s also important to let the rep signal when they need help. I think that’s how you build a good bond between a manager and an employee when they feel comfortable expressing, “Okay, I might not know this,” and having that set up in advance of the call.

JB: Cool. Anybody else? Yeah.

Audience 2: I’ll direct this to Chris, but if anybody else has a perspective, that would be great. Chris, you had mentioned about building out a really good, deep understanding of the buyer. Can you talk a little bit more about what you actually do there? Is it that you build buyer personas and is that in a complex sale? Do you build one for the CFO, for the CMO, the CSO, the CEO, the COO, whatever? And if not, do you build out specific buyer personas for specific situations to give to the sales rep when they’re in a particular situation? You look up John Smith and you figure out what you want to understand about John Smith to tell the sales rep?

CO: Our buyer personas are not a one-to-one thing. We identify our repeatable, predictable buyers and what their pain points tend to be. There’s always going to be a little more nuance to that, but the high-level overview as far as how we approach it is we have these buyer persona cheat sheets, they’re not multiple pages. Contrary to this message that I said you should know your buyers in depth, I think over-complicating a buyer persona cheat sheet or some sort of learning material is done a little bit too often.

So that’s how we do it, we do it by the buyer that is involved in our typical sales process. We’ve got a VP of sales, we’ve got sales enablement, sales managers, and a few others. I think as far as how you structure your buyer personas, like I’m talking about right now like we have these buyer personas that are involved in a typical sale, your market needs to dictate how you structure your own buyer personas. We structure our own buyer personas because that’s how our market is actually laid out. Other companies are a little bit different. They might structure their buyer personas by vertical instead of the specific people that are involved in a sale, regardless of which vertical that is.

And the final note that I would add to buyer personas is making sure it is based on fact rather than just kind of guessing. I know a lot of people who have a lot of domain knowledge, and they just kind of go into a room for a few hours and they write up a buyer persona cheat sheet and they say, “I know a lot about this market, this is good enough.” And they send it out into the field and it misinforms the salesforce pretty wildly. You want to make sure you’re talking to buyers and every line you put on these cheat sheets or however you approach it should be from their mouth, not your mind.

HA: Validated.

Host: Cool, thank you very much. We have time for probably two more questions, so one here, and if anybody else has a burning question raise your hand.

Audience 3: This one’s for you, John. I was wondering from a psychological perspective, you’re dealing with sellers on the front line all the time. What do you think has the biggest impacts in terms of the sellers’ beliefs, their expectations, their emotional state, their actions or their past experiences? What do you think has the biggest impact on confidence, or a seller’s confidence?

JB: That’s a good question. I think just being cool to fail, you know what I mean? I think we’re in such a short term, month-to-month, go go go, have to hit every number, and I just wish that we would back off a little bit. That’s what shatters confidence is when you push so hard to get a number and the kid doesn’t hit that number and then it’s this self-defeating prophecy and it just gets worse because now they just feel worse and then they do the wrong activities more and more and more. So I think just – I wish I could just say chill out but –

HA: You can.

JB: You know what I mean? Just chill out, let them fail, give them some mediocre leads, not the worst.

HA: Some quick wins.

JB: Yeah, actually that’s a great point. I just hired Morgan Ingram about a year ago and our buyer personas were mainly VPs of sales and VPs of enablement. I was a VP of sales so I can kind of coach him on that, but he was an SDR and an SDR manager. He didn’t even know what enablement was. So I had him go and do his homework, I actually said, “go do some research” and he did a great job. He actually went on LinkedIn and said, “Hey I’m now selling to enablement, can anybody help me out?” And a whole bunch of people said, “I’ll get on a call with you, I’ll get on a call with you,” and he had good conversations with them.

But to get him some quick wins – he was an SDR and an SDR manager – I’m like, “Start cold calling into SDR managers because you know how to speak that language. So just call into them.” He got a lot of deals but they all stuck there because they’re not in power and I have to figure out how to actually help him, coach him on that problem. But getting him started and having some quick wins and making it fun – I see too many people take this way too seriously. You know what I mean? Like call blitzes – can I beg everybody here, please do not have a call blitz day. Don’t ever have a call blitz day, there is not enough Red Bull out there for me to get hyped up for a day’s worth of cold calling. An hour, have some fun with it, do power hours so everybody’s doing it at the same time so it’s not like one person’s making calls and one person’s sending emails and one person’s doing research. Make it a team. Yes, sales is an individual thing, we’re all hitting our individual quotas, but if you don’t make it a team event it becomes really boring really fast. And then different confidence levels rise above based on personalities alone. You don’t want to let that happen.

Audience 3: My question is about, do you guys see or use mindset training or neurolinguistic programming so that sales reps at the right level understand the nuances of assumptions and expectations and the space between speaking and listening and all that kind of stuff, or is it all just tactical metrics actions?

HA: That’s literally the first thing that we cover is mindset when we have our new hire sales training program. So, we don’t go super deep, I am certainly not a psychologist, that would be terrifying, but we do start off by making sure everyone has the same mindset and mentality when they come to work around how we talk about our customers, how we talk to our customers, and how we work together as a team. I think that creating that sales culture and forming that mindset, that’s a group mindset. One positive is that it can be really impactful when you’re not hitting your numbers, when you hit those bumps in the road that as salespeople we are all bound to hit. It’s that reminder that as a group, how we think about this and how we approach this is in a positive light. But again, it’s not a scientifically proven method.

GR: I’ll just add, on our part we are investing more in personalized learning for our sellers, and using different learning methodologies. There’s a basis for that whether it’s book-based learning or problem-based learning, so it drives more situational awareness for example. I suspect in your question about when do I put a new seller in front of a customer, there’s a lot more emphasis in creating learning that is aligned with the persona of the end buyer, the personality of the seller, and to some extent the learning experience, in terms of whether it’s drip drop to an unmotivated learner or it’s more of a full based model to a motivated learner.

JB: Chris, anything to add?

CO: No, I’m just laughing to myself because the only mindset training I do is I listen to Britney Spears on the way to work every morning.

HA: Do you sing to it or do you just listen?

CO: Oh, I just listen.

Host: Maybe that’s the secret, Britney Spears on the way to work.

JB: A cheat on that and then we’ll finish up, there’s a product called Crystal Knows, have you ever heard of Crystal Knows? Crystal Knows, and it’s not a drug site. It’s Crystal Knows. It gives a personality profile of every single one of your buyers, disc-based, and it tells you how to communicate with them, so there’s a cheat for you.

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