- Hi, friends. Welcome to my new podcast episode. It's episode number six today. The number six has always been a very special number for me, so I have prepared a special discussion for this episode, which is very dear to my heart.

- Today, I'd like to discuss how to become a challenger. Many on the sales and marketing side may have heard about the methodology. Some may even have read the book or gone through some training at their companies.

- I've invited one of the challenger evangelists, Jen Allen. Jen is the host of the Challenger Podcast and a part of the Challenger Inc, the consulting company that is providing education and implementation supports to leaders and their organizations who wish to become challengers. Jen and I cross paths at CEB, the company that originated the challenger idea. I'm very excited to interview her today because she spends countless hours every week speaking with senior sales execs refining the methodology as it evolves over the years.

- Even if you think you know challenger, I guarantee you will learn something new today. Ladies and gentlemen, allow me to bring to the virtual stage my special guest, Jen Allen.

- Hi Jen, how are you?

- Hey, I'm great. I'm excited to be here with you. How are you?

- I'm doing well, thanks. You know, I'm very excited to have you on board as well and it's great to have you speak on my podcast episode. I will put the little marque here at the bottom with a call to action for everyone who's watching this to visit Cerebrations.info for a little more information about yourself, and also explore the other episodes that we have within the podcast series. Maybe watch any others that they haven't seen already. But just to get started, before I let you provide a little bit of information about yourself, just wanted to put some context here. So people have heard about the Challenger book and mainly may have actually even experienced it in some sort of training in their corporations, but maybe a lot of those also are not aware that there is a whole organization around it providing education about Challenger and helping companies implement Challenger. So let's start with that. Tell us about yourself and how did you become a Challenger evangelist?

- Yeah, so fun fact, we both started, or not, you didn't start there, but we both spent time at an organization called Corporate Executive Board, or as many people knew it, CEB. I started there back in 2004 working in their sales and marketing practice as an account manager for their subscription memberships. And then back in 2008 when the economy sort of fell apart and we studied what were high performing sellers doing differently than core performers, that's obviously where the challenger research was born. I switched over into that team, gosh, back in, when was that? 2016, out of the subscription side and into the challenger implementation side. And then we split off after Gartner sold us off to private equity. So that's our backstory of how we became Challenger Inc. A lot of people don't know that we ever left the Gartner CEB umbrella. I actually have been a lifelong individual contributor. I never wanted to be a manager, never wanted to be a leader. I always just found that there was so much I could learn about how to improve my selling skills. And so I did different roles like account management, pure hunter, transactional, large, you know, enterprise, all different sizes. And then March of last year, I was a hunter for selling challenger into businesses. And I just started to notice that the frequency and the quality of the leads that we were getting were just ticking down, down, down. And so, you know, I think for many of us who sell, the easy motion is to go to marketing and say, hey, we need better leads, we need more leads. I'm sort of in the school of thought where it's like, if you have a problem that's affecting you, you gotta figure out on your own how do you solve for that problem versus relying someone else. So I looked to LinkedIn and I just said, "what if I start talking about the problems that we help companies address? And what if I share insight in that and just see if it sparks anything?" And from that, a couple things happened. So one, I got on our company's podcast called "Winning the Challenger Sale", which I now host. And then two, I started to notice something really interesting, which is when I would talk about problems on LinkedIn, I would get very senior sales leaders popping up into my DMs saying, "hey, very curious about this. I've heard about Challenger, never really was a fan of it, but this hits on something. Can we talk?" And then when I'd get on the phone with them, I'd say, "just out of curiosity, why didn't you go to our website and just fell out a form?" What they said was, "Jen, I have no idea who the sales rep on the other side of that form may be, but I know through reading your content, watching your podcast, whatever, like I know where you stand, I know your view of the world, so I wanna talk through the problem with you. I'm not even necessarily sure I wanna move to solutions." So that just lit up in me and I was like, gosh, I wonder how many more people like this there are. So I went to our CEO and said, "can we formalize this into a role where the end goal is to really evangelize the problem less so the solution." And that's how I ended up in the role in January.

- Wow. Okay. That's great. I mean, that's a, first of all, very interesting story and you touched on a lot of things that I was gonna ask you a little later. Thanks, by the way, about saying that it's not always marketing's fault that the quality of the conversion is going down. As a marketing leader, I appreciate that as well.

- Yes. That's great.

- But, yeah, I have a lot of questions that are based on what you just said, but before we do that, you know, going back again to the book, I mean, it's been more than a decades, even people that have read that book multiple times or have gone through training, that may have happened in the past many years ago. I personally, you know, it's been a long time since I read it. I mean you mentioned we both worked at CB. After CB, I became a customer of Challenger actually at one of my previous companies. So we went through some of the formal training as well. Oh nice dog. Hey, hello.

- Scratching and just bring him up.

- So, you know, I've gone through that, but I know that it's an ongoing concept, it's evolving methodology. I mean, let me just pick your brain a little bit about what has evolved about the original Challenger idea over the past decades.

- I love this question because this is one of my... One of the things I think that makes sales so fun is it's not like you get good one year and then you're good for eternity. Every year, buyers behave a little bit differently, right? So if I reflect over the past 10 years, probably the most meaningful shift has been the increase in consensus buying. So back when Challenger like first came out, "The Challenger Sale" book, we didn't talk a lot about it then because it was just starting to change. If we think back to like the early 2000s, it was still very much a time where, you know, a decision maker could sit there and say, I wanna buy something. Maybe I have to touch on procurement, but I could pretty much independently move. After '08, '09, a lot of people got burned carrying the bag and they said, "look, like I'm gonna ask Bob and Susie, can you weigh in on this, right, to deflect risk?" But now, between 2015 when the book, "The Challenger Customer" came out in 2020, which was the last time we studied it, we saw the number of stakeholders on average in a deal rising from 5.4 in 2015 to 11.2 in 2020. I mean, when we think about that from a seller's perspective, it is absolutely crazy, right? And I think many of us have been taught traditionally, you go around and you heard cats, and what do you want? What do you want? What do you want? But you get 12 people, it's just not sustainable, right? By the time I get to the 12th person, like maybe the first- Right? It's like that's a really difficult motion. So I think one of the biggest changes is as a byproduct of that decision making by consensus, we've seen a lot of deals become lost. Not because they don't think you're good enough or your solution isn't good enough, but because good enough is okay, right? Like how I'm currently solving the problem is okay. I don't wanna assume the risk of better, because better means change, better means disruption, better means, you know, risk to my political capital. So one of the things we've largely been talking about lately is how do you compete as a seller with someone who's like, I know you have a better solution, but good is good enough.

- Yeah, yeah. Sticking with the status quo basically rather than jumping on a new ship. It's interesting. I mean like I definitely see the same trends in my world, you know, in the situations where we have to sell in market too. I mean, I'm wondering if part of this in according to you and your research is part of this is also that the solutions that are being offered that are more and more complex and involve different parts of the organization by default because they're more technologically sophisticated. I mean these days everything is a platform, something that needs to plug in into many other different systems and work together. And, you know, CIOs and CTOs have to be involved in that. Is that part of the reason?

- I think you hit on such an important theme, which is if we think about replacing a manual tech, a manual process, right? So I'll use an example. We bought Chili Piper here at Challenger earlier this year.

- I bought it before as well.

- Yes. Right? I'm huge fan of them. And when you look at what they do, there is a clear value prop, right? And it lines back to a clear problem we were having as a business, which is the amount of leads that were filling out forms converting that to first sales conversations, right? So when I saw that, I thought, this is a no brainer. This is gonna be so easy, it's not terribly expensive, no problem. But because of the fact that the technology replaced a manual process and because the fact that there were IT considerations, marketing considerations, sales considerations, legal considerations, right? With the access to customer data, I was shocked by just how many people needed to get involved in that decision, and it had nothing to do with the price. So I think historically, we've always looked at, hey, if you're selling a CRM or an ERP system, you know, that's when you get into consensus buying and that's when you have to navigate buying groups and so on and so forth. But the reality is it's even for smaller price points to your point where the thing that we are buying is disrupting how we've always done something.

- Yeah. Yeah. And that's important because I think everyone's goal is to decrease the complexity, shorten the decision making process so that the deal takes place faster, but at the same time, we are offering more and more functionality that actually makes it more sophisticated and complex. I mean, this is kind of a good segue into my next question. Where do you think Challenger is going in the post-pandemic world? Is there a new direction that you see?

- Yeah, so I think the core fundamentals of Challenger do not change, right? When we think about we have to make the cost of inaction greater than the pains of change, or we say like, the pain of same has to be greater than the pain of change. I think it's a little bit Groundhog Day-ish. Like we go through a recession in '08, '09. We learned those lessons. And then the market gets good. And, you know, hey, I've fallen victim to it, we get a little lazy, we can order take, it's fine. So I think the core tenets of Challenger do not change. We have to reflect on how we are communicating with our customers, how we choreograph those conversations, so that we create an urgency to act as opposed to like, hey, that's interesting, call me back in six months. But I think one of the interesting things that we've realized as a business is there are a lot of sellers and candidly even managers and leaders who don't really recognize where sales is falling short in the conversation. Like, we hear things like it's price or it's budget or it's competition or whatever, right? And we're like, hey, like nothing we could do, it wasn't our fault, right? And we go in our CRMs and we log in as close loss budget, close loss competition. And so one of the things that we recognize as a business is half the battle is creating an awareness in the sales teams that there is a conversation gap. So recently, we rolled out a tool, which is, I think, there's a lot of companies who use like a win/loss tool, or we're still ready their, customers post-win/loss. But where we saw there was a gap is like we're not actually doing that during the sales experience, so we have to lose to learn. You know, there's a tool we released earlier this year called Loop, where let's say I do a group meeting, I send this out to seller, or I send it out to the customers and I can get customer feedback on, hey, I came to this call and I really wanted to see a demo, and you just barraged me with a hundred discovery questions, right? So I, as a seller, know where am I going wrong, where am I not meeting the customer where they are. I think that's a huge important piece that frankly we missed as in creating recognition and awareness of that gap.

- It's interesting. So you're basically doing customer satisfaction surveys throughout the whole process all the time, like in real time you're trying to react to those.

- Exactly. And like when I heard that we were releasing this, I mean I couldn't have been more anti it because I thought what most people think, which is nobody fills out customer surveys, right? Like what a stupid idea. But where I was reframed by our head of product is, Jen, you've gotta realize when we traditionally send those, we send them after we lose. What is a motivation for our customer to fill-out a survey to make us better after we didn't do anything to help them, it's zero, right? So it was definitely reframed in the sense that I've sat on calls where I did my research, I came to the call, I had three very important questions I couldn't get addressed by the website and I never got the chance to ask them 'cause, you know, I was run through a script. So I think it's a different motion in the sense that customers are looking for something. If you give them an opportunity to say, hey, I'm not getting what I need, that's a totally different motion than post-close.

- Great. Great. I mean, I'm very curious about this. I mean, you kind of hit on one of my concerns, what are people who feel obliged to fill all these surveys in such a frequent pace, but it looks like it's working out. So I'll definitely look into it a little more. I would like to learn a little bit more about it. This is great idea. One thing I wanted to mention again is as part of my conversation with you, you know, as I've been on both sides of, you know, being part of the organization that's offering Challenger, and then after that being a customer, and now being at an organization where people that come from, you know, like some of the sales folks have been trained and introduced in Challenger at previous organizations, so some come with some knowledge, others come, I mean they may have just heard the name, but they don't know too much. So there's a lot of different opinions out there and I sense a lot of times some skepticism. And especially some of the folks that you've been around longer in sales, they just basically a lot of times say, well, you know, every 10 years, there's a new methodology and, you know, we kinda go through, you know, all these and we recycle and recycle. So what do you think makes Challenger not a hype? Why is it not a hype? I think I lost your audio.

- Sorry about that. I relate to that, because if you just Google sales methodology, I mean, you could spend six hours on Google going through all of the responses. So I empathize with that. I totally hear it. I think the thing that makes Challenger not a hype is because a lot of methodologies are born out of someone doing something, realizing it's working for them and then saying, hey, I'm gonna teach this out to other people. So it's a little bit subjective. It's like, hey, this is what worked for me. And candidly, like some of them originated 20, 30, 40 years ago. And it's not to say that they are not good, right? I look at any methodology is a step in the right direction because we are giving our sellers guidance on how to think through the conversation. So I'm a fan of methodology in general. I think the thing that's different about Challenger is it wasn't us sitting in a room saying, this is what we think sellers should be doing. It was us sitting there and saying, let's just study sellers, right? Let's look at 40,000 sellers at this point and isolate, are there spikes in behaviors and skills because of how the sellers are treating the conversation differently. So that's, I think, what makes it unique is it's data driven. It is not our opinion of what sellers should be doing.

- Yeah, that's a very important distinction. So kind of similar to that, a lot of companies have implemented or tried to implement Challenger. Where do you think they typically go wrong? Why do some try it? I mean, like I said earlier, even sales folks that come from environments where they've been trained on Challenger kind of comes skeptical.

- Yeah, this is a really good question and candidly, I think we got it wrong in the beginning. Like when we released the book, we were like, okay, let's just throw everybody in a training classroom and teach 'em how to be challengers. And, you know, I think a lot of organizations have learned a lot that like you can say all the right things, you can teach all the right things, you can do a really high impact classroom, but we are rewiring how sellers believe they win. We're rewiring the things that are coming out of seller's mouth, which we all hold very close dearly to us. So putting people in a training classroom and just teaching them this is what challengers do candidly is a really fast way to fail. So where we see a lot of companies miss is they'll put those sellers in a classroom and they'll change nothing around them. So I am a seller, I still get the same coaching I got before. No coaching around how am I thinking about the reframer? What do I believe this customer's status quo is? I get the, like, when was the last time you talked to them? What do they sell? And just like the same basic questions. Or two, you know, I get content collateral from marketing or product, and it's all about us, right? So how as a seller can I actually implement this training if all of my enablement is wired around a product sale or a question based sale or whatever methodology we used before. So I think what we've come to learn is it is so much more about the organization than it is the individual. And when you neglect those things, what you do is you make it infinitely harder for that salesperson to be able to adopt and implement Challenger. So we have to really step back and say, sellers should be the last piece of the puzzle. We need to look at the messages. We're creating the pitch decks. We're creating the collateral, the coaching, the enablement, and make sure that aligns to this way of selling so that when we bring the sellers in, we don't have sellers saying, yeah, but nothing I have supports this. And again, I think that's a lesson we learn the hard way early on. And now that's how we're structured in supporting our customers.

- That's a very good point. I mean, you mentioned marketing and collateral. And partially one of the things that I discussed with you when I first reached out for this podcast episode is that overall, a lot that I hear out there, you know, in public domain is conversations about Challenger focuses on sales. I mean, it's a sales methodology. But there is a role for marketing and I'm a marketer. So, you know, how do you become a Challenger in marketing? What is the role of marketing in Challenger?

- So I actually, I love the way you just said that, because I agree. It's traditionally been viewed as a sales training model whereas I like to think of it as a mindset. It is a mindset regardless if I'm in product, marketing, sales, I don't care. It's what I believe I need to say and do to help a customer realize the cost of an action and give them urgency to act. So if I'm in marketing, right, one of the things that we observe is companies who are really savvy at marketing and sales, both doing it, marketing is sitting there saying, my job is to spark curiosity in the problem. It is not to sell the solution, but it is to help a customer say, hmm, never thought about the problem like that. How can I learn how relevant this is to me? And then how can I learn more? And I think in marketing, we have to lean in to this idea that customers don't wanna just pick up the phone as soon as they think they might have a problem. We wanna learn, we wanna learn on our own, we wanna get educated, right? So marketing's role shifts in a challenger mindset because we are sparking curiosity and then we're giving customers things that help them assess how big or small is this problem for me. So think like a diagnostic or some self-assessment that allows me to kinda benchmark myself. And then I'm opening the door to a further conversation. And you think about that motion, right? We're teaching sellers, here's an insight to lead with, here's how to have these conversations. Marketing then starts priming the pump. So when I, as a seller, get a lead, it is someone who has already expressed explicit interest in the insight that we've taught through the marketing channel. And now, I, as a seller, have an open door to say, let's go deeper on that, right? Like, let's have a conversation about what you're seeing and how it's working. And that I think is when this all works out. So I think to be a challenger in marketing, to answer your very specific question, we really have to align with sales on what are the problems our customers are under appreciating in their business that's costing them, how do we help them size it, and then how do we spark curiosity through our messaging our content in the channels where our customers are going to learn, which is different for every industry. I have an easy. LinkedIn's a great place advice where sellers learn. So I know if I spend time there, I am likely to see leads pop out on the other side.

- Yeah, that's very important. I mean I kind of remember from some of the training that I've done on Challenger that on the marketing side, I mean kind of like the three main types of content you should think about are the spark. You mentioned some sparks, right? Spark interest. The inform parts where you provide more information about it and then confront, and that's the diagnostics. I mean I know what a diagnostic is. I think a lot of people out out there who haven't been part of the Challenger world may think about it is from a purely clinical point of view. But let's think about benchmarking surveys, self-assessments, things like that. So these are important tools and I see them sometimes and I'm very curious. When I see one of these, I actually click on them even I may not be interested in buying just to kinda explore the the customer journey.

- Yeah.

- Yeah, but it's not that often. So there's still a lot of room for improvement. And I'm covering this here.

- I mean you look at most websites, right? And I would say to a certain extent, we've even fallen victim to this too and we're working on fixing it, but most websites are geared around here's who we are because traditionally that has been the motion, right? Like let me tell you all about us because you're here, you clearly wanna hear about us. And I think it's a missed opportunity, right? I think in a customer's mind, we're sitting here saying, how big is this problem? Do I wanna risk going to my boss to ask for money if I don't feel confident that I can demonstrate that there's a huge problem on the other side that if left unfixed, it's costing us, I might shy away. So I love how you talked about that and I love that you're a student of the game, right? Like I'm gonna click into it and see how they do it regardless if I need it or not, 'cause I think that's where diagnostics really play a role is help me make a case that this problem is actually bigger than it should be.

- Great. So my podcast is intended for both sales and marketing audiences. And, you know, we spend a little bit of time here on marketing, but let me get back to sales a little bit at the end just to ask you about one question that maybe has been covered in the past, but I personally think it's a little more in the periphery of what the discussion has been about challenger. So there's a lot that is being done on the training side. You mentioned earlier that just training by itself is not enough, and obviously, it has to come from the top. Like the leaders in the organization need to show that they've changed their own behavior to get everyone else around them. All the stakeholders that are supporting the sales process, marketing, product, et cetera, they need to also change the way of thinking, the mindset that you mentioned. But what about just even ensuring that when you're hiring new sales folks, new sales executives, that you are getting the right candidates. So I guess my question is how can sales leaders tell a challenger great candidate apart from anyone else that they may be seeing as part of their hiring process? Are there some specific attributes that may lead to higher likelihood of success in a challenger environment?

- Yeah, this is a really good question because finding existing challengers is a little bit like finding a needle in a haystack. Like I forget the exact step, but it's something like 17% of all sales reps are challengers. So the likelihood that you're getting one in your hiring pipeline is not very high, right? So first of all, to find the ones that are, one of the best techniques to do it is behavioral based interview questions. So really, what we're gauging is someone's mindset, right? Like when I'm backed into a corner in a tough situation, what are the belief systems and the assumptions around what I need to do in order to get out of it? So when you think about a situation, like let's say, a customer is asking you for a discount late stage, how do you respond? A relationship builder or a hard worker may go to the... Or actually, let's just say on a relationship builder. A relationship builder is gonna be like, let me go to my boss and let me fight this fight for you and let me see what I can do for you, because their judgment tells me I have to be liked by the customer. So I have to show them what I will do for them, right? And they might tell a story of, you know, I went to my boss and I was able to show this, this, and this. That would give me a kind of signal that that might be a relationship builder mindset. Versus a challenger will say, that is a signal to me that I have failed earlier on to demonstrate the cost of doing nothing. So I'm gonna go back and I'm gonna align with that buyer on let's make sure we're on the same page with the size of the problem that we're solving, right? So when you do behavioral based interview questions, it exposes the belief system of that seller as opposed to, you know, tell me about a deal that you won. I think what we wanna gear those questions towards are obstacles, difficulties, things you can see what is the, again, that belief system. So that's one piece. The second piece is challenger can be learned, right? It's not like a nature thing you have to be born with it, that you have to have brown hair, blonde hair, whatever. You can learn to be a challenger. So what we also wanna look for is the propensity for someone to receive coaching, the propensity for someone to be comfortable with the, you know, the idea of a no. So we created a tool called Challenger Hire, which basically is an assessment tool that happens after your screening interview, but before your manager interview. And basically, what you get on the other side is the manager walks into their interview with you with a scale that says like zero to a hundred, this person is, you know, 35 on relationship builder, they're 60 on hard worker, they're 40 on problem solver. And then that helps you understand, what do I need to push on? Because what we often have to be mindful of is there are some sellers who won't learn new tricks, right? It's a will issue, it's not a skill issue, they just don't want to. But if you don't have a will issue, most sellers can learn to become a challenger. I think our data suggests like 23% of this overall sales population will fall short of doing it, but oftentimes it's that will issue. So I think you wanna be looking for how firm and set in beliefs is this individual, or are they someone who is open to learning and that can be then taught and coached to become a challenger.

- Interesting. I think that's very relevant not only for challenger, but in general, the sales environment is changing. I mean it's becoming more technology driven. I mean we talked about technology earlier, but, you know, it's impacting everyone's life. I mean, a few years ago, there would be distinction digital marketing versus traditional marketing. Nowadays, I mean it's all digital, it doesn't matter. And it's becoming the same for sales, especially after the pandemic and during the pandemic. It's more and more virtual in many ways. So you have to learn how to use new systems and you have to be open to that. So that's the assessment that you're doing from that point of view, I think, it's important, not just from a challenger standpoint but also for any kind of aptitude to learn new things and adapt to the environments that are changing. So that's great. What are the key takeaways? I always ask this question at the end. I want this to be educational. So when people watch this, what should they try to retain as the key takeaways from the sales going forward?

- Yeah, so I'll break it into sales and marketing. If I am in sales, I want anybody listening here to reflect on the choreography, whether it's intentional or it's just in our head that we believe we need to go through to get our customer to change and have an honest conversation around how often is that yielding customer action. Like that is a moment we, as salespeople, need to have of reflection to say, am I from the school of thought that if I show how much better our solution is, somebody buys, or am I from the school of thought that says to get someone to buy, I need them to realize that the cost of an action is actually greater because the pains of changed are the things that are gonna kill us in the end. So that definitely one big takeaway. Have that honest moment with yourself. Look at how you traditionally lead sales calls and see which camp you fall into. That's for sales. For marketing, look at the content we're producing, right? There is a time and place for talking about us and what we do, but if 99% of our content is skewed towards that, we are only hitting the 3% of the market that's actively shopping and we're missing a huge opportunity to prime the pump for sales by getting people, creating demand for customers to say, hey, I wanna take another look at how I approach this problem. And so for marketing, again, same thing. Look at the choreography of our content. Are we starting with us talking about the value of our solutions, our ROI and call to action of where they can buy from us? Or are we starting with an insight? Are we helping a customer size the size of the problem in their business relative to that insight? And then leading that into why they would have a conversation with sales, like what are they gonna get out of that? So I think both two in the same vein of intention, but sales marketing kind of looking at it a little bit differently.

- Great. Yeah. That's a great summary at the end. So really appreciate it. Well, I think we are at the end of our interview right now and we covered so many topics in just about 30 minutes. So really I'm very happy and excited to re-watch this after that and kind of learn more things, 'cause I was trying to follow a lot of things you're saying, but some of it requires a little more kind of like internalizing and trying to apply it to your own situation, like you said at the end. So great stuff. I really appreciate it. Thanks, Jen. I hope you enjoyed it as well and-

- Absolutely.

- Looking forward to speaking with you again.

- Likewise. Thank you so much for having me.

- All right. Thank you. Buh-bye.