The Sales IQ Podcast

Mastering The Challenger Sales Model, with Jen Allen

March 16, 2022

The Sales IQ Podcast

Join us as host of the show Luigi Prestinenzi talks to thought leaders from around the globe about the art and science of sales and marketing, personal development, and the mindset required to sell more everyday. Luigi is a master of creating pipeline and breaking down targets, he specializes in helping sales professionals build the mindset to achieve greatness and #bethebestyoucanbe.

If you're in need of a sales strategy geek-out, this one is for you. Luigi's guest this week is Jen Allen, Chief Evangelist at Challenger.  A renowned method for B2B deals, and based in research, it's about taking ownership of your sales process.

In the episode, Luigi and Jen examine the why, what, and how of Challenger Sales. Jen tells us why it's so impactful, how it fits in an evolving sales environment, and her favourite ways to apply it.


Jen is most active on LinkedIn, and is co-host of the podcast Winning The Challenger Sale.

Find Luigi on LinkedIn.

If you want to strengthen the structure around your sales process, the Create Pipeline course from Sales IQ, is a great step forward. Next intake closes soon 🚀

Luigi Prestinenzi
CEO & Co-Founder @ Sales IQ + Host @ Sales IQ Podcast
Jen Allen
Chief Evangelist @ Challenger™

[00:00:00] Luigi Prestinenzi: By the Sales IQ Network, this is the Sales IQ Podcast. I'm your host, Luigi Prestinenzi, and each week we'll be going on a journey that will inspire you, motivate you, and help you be the best sales professional you can be. Our focus will be on mindset, tactics, and the strategies that will enable you to create more pipeline, and win more deals.

'No' in the sales process is the worst possible outcome. The reason it's the worst possible outcome. It's because if you've dealt with a prospect and you've progressed the opportunity to appoint a proposal, so you've taken the time to really understand what the problem is. You've determined. There is a benefit.

There is an outcome that the prospect wants to work towards, and then you arrive at a point where the prospect decides, Hey, I don't want to move forward. I'm just going to stay with same. I'm going to stay with the status quo. It's not the best outcome. And it's not just because yes, we as a sales person, whereas a sales professional involved in the process misses out on, you know, the fantastic feeling we get when we close the opportunity and the commission and all the things that come with it, the reality is.

If we were working with a client or a prospect to help them with a proposal to help him put together a business case for change, it means that there is an outcome that we're trying to help them achieve. It means the outcome. That we're helping them scope the solution that we're helping them work towards is something of benefit.

It's something that they need to achieve. So the first thing, you know, when we'd miss out, because of no decision, it's a fact, all the actual client isn't going to achieve the outcome that they want to achieve. But the reality is over 60% of deals are lost to no decision. That's massive when you think about it, but what can you do in that, in that situation?

What can you do when the client decides is as the committee, the buying case. Decides that, that I want to progress the opportunity that I want to progress and go through the pain of change, because remember, with any sale that we work on of sites, I'm not talking about the transactional deals. I'm talking about B2B enterprise selling into mid market enterprise opportunities.

That require multiple people to make a decision. A lot of these opportunities arrive at a point of no decision, and there are things that you can do to avoid arriving at that point. And that's what this week's episode all about. And I'm pumped. I'm absolutely pumped because we have a practitioner, a practice.

All of the challenge of sale. Her name is Jen Allen and yes, the challenge of sale for some reason creates so much debate. Some people either love it, or some people absolutely hate it. And if you haven't read the book, I would recommend reading the book because for me over the book, I'm like, yes, this is fantastic.

I actually really loved the book. Some of the concepts within the book, but I think what's happened is that some people have misinterpreted what the book talks about and what Jen is going to talk about today. She's going to sort of demystify some of the things and the concepts that are in the book, but she's going to talk about some of the tactics and some of the strategies that she employs every single day is to put together large deals, complex deals, where there's multiple stakeholders and Jen shares a really interesting stat.

In an enterprise sale. Now there's over 11 people involved in the buying committee. Now think about that over 11 people, it means that during the sales process, we, as sales professionals need to engage, influence, bring people on gain consensus. There are multiple stages of commitment that we need that need to take place with multiple stakeholders.

And it requires strategy. It requires a lot of thought and it requires an intentional focus on really making sure there's alignment on a problem that everybody agrees that that's the problem they're trying to solve. And this is the pathway that we need to put together, or we need to go on to at particular outcome.

[00:03:54] Sponsor: This podcast is brought to you by the Create Pipeline program from Sales IQ Global.

This program will equip you with the skills, tools, and confidence to run
an outbound strategy so you can generate more qualified opportunities and close more deals.

Hear what Ellis from DocuSign has been able to achieve since joining the program and our incredible community.

"So, my name's Ellis, I work at DocuSign as an ABR. And the reason I started Sales IQ was because I really needed that guidance and that training to make sure that the outreach that I was doing was hitting the nail on the head.

So I was lucky enough to start the program early on in this role and since then I've been pretty successful and last quarter I finished on a 185%. So I've seen some huge results by adopting the principles."

Our next cohort is starting soon. So to learn more, go to, or if you have a team of sellers, talk to us about our in-house offering.

Control your pipeline, control your destiny, with Sales IQ.

[00:05:00] Luigi Prestinenzi: So, this is a fantastic episode for any salesperson working across any vertical and even from a B2C perspective, there is so many things that Jen's going to talk about today that you can apply in any industry across any particular sales process.

Welcome to the show, Jen.

[00:05:19] Jennifer Allen: Thanks so much for having me.

[00:05:21] Luigi Prestinenzi: Yeah. I'm really excited. And I'll tell you why I'm excited because I am a fan of your podcast. And for all of our listeners, we will. A link to where you can listen to Jen's fantastic podcast, but I'm also a big fan of the content that you're sharing on LinkedIn and on using some of the tactics and some of the strategies that you're talking about in my sales process.

So I'm really excited today to really dive in around how sellers can become value creators in the sales process. So welcome to the Sales IQ podcast.

[00:05:52] Jennifer Allen: Thank you so much. And as someone who follows your content, I'm really excited to be here and nerd out about sales with you.

[00:05:58] Luigi Prestinenzi: Yeah. Awesome. Now I want to get into this topic. Because again, I think in 2022, you know, the, the, our profession has come so far, but I think there's still so many gaps. That sellers are creating for themselves. You know, when they're not really creating value in a process and they're kind of pushing the. The features and the kind of pushing their products to clients.

But before we get into that, I would love to know a bit more about you and how you started in the role of selling.

[00:06:29] Jennifer Allen: Yeah. So like probably 99% of your guests never thought I would be good at sales, never wanted to do sales. I kind of fell into it. Back in oh four, I had a roommate working for a company called corporate executive board, which has since been acquired by Gartner.

And she said, Hey, Really smart company, really fun, happy hours. You should just come here while you're trying to figure out what you want to do with your life and just work with me. And I said, that sounds awesome. So I initially interviewed to go into their meetings department because I was doing events management and stuff like that in my previous gig.

And they slotted me into account management and I was fortunate enough to work for an account manager who just. Absolutely blew me away. I thought when we were, when I was in that organization, I was working with CMOs to sell them like an annual, renewable subscription service. And so she would call these CMOs of these really big companies.

And I remember I would just always be in awe of how effortlessly she would kind of challenge their thinking and ask really smart questions. And that's. Drew me and made me want to stick with sales because it felt like such a far reach for me. And so I started in account management, then switched over to new logo acquisition, and then switched into the challenge or segment before we got sold off.

Because at that time I said, okay, now I feel like I've kind of played with account management. I've played with new language, new logo acquisition. Now I want to try bigger, more like, you know, enterprise deals and, and play around there. So that's how I got to where I am today. And then in January I switched into a new role that chief evangelists for a challenger where I'm out there trying to educate the market on some of the problems that we solve. Yeah.

[00:08:00] Luigi Prestinenzi: What an awesome journey. And it's funny, like you're right. Like I don't, I don't think I have yet to interview guests that say I was, you know, six and. I just don't want to be in sales. Right. I think we've all fell into it. I was just like, yo, I fell into it. Cause I couldn't really do anything at school.

I'm not very smart. So I was like I just want to talk, cause I think, you know, your, your career span and you've got to work with, you know, when we talk about CB, we talk about Gardner. We really are talking about organizations at the forefront. Really, you know, they're working with enterprise grade organizations and they're seeing trends before they occur.

I'd love to know from your perspective, having worked, you know, with net new logos worked with sort of small organizations into enterprise, why is value creation such an important element when it comes to selling to any organization, both, you know, medium to large.

[00:09:01] Jennifer Allen: Yeah. So I'll speak to both what the facts would show as well as just my own anecdotes and observations.

So, candidly, I think for anyone that knows challenger, it was born out of research that we did with customers to understand there's a say, do gap with customers. So if you ask customers what makes you loyal there it is. When you ask them that question, they'll tell you a very different thing than their behavior would suggest and what their behavior would suggest when we analyze it.

Is that out of all the things. Might matter to make a customer pick you and grow with you and buy new products and advocate for you and all these things that we want. You can kind of boil them into four categories, right? So it's like how good they perceive your product and service, like how they look at your company and brand how fair they think your prices and then the experience they have in buying from you.

And so the research back reason that creating value is so important is because. 53% of what drives that customer's loyalty to you has to do with the type of sales experience you deliver. And I love the way that you call it value creation in the sales experience, because customers aren't just looking for the person who's the best at describing their products and services.

They're actually looking for the seller who's coming in and asking really smart questions, helping them think differently or introducing information that conflicts with their current belief system in such a way that they recognize shoo, the way I'm approaching. This is actually costing me or introducing risk or something.

And I look at that seller. As someone who came in and exposed me to that blind spot, like that's what customers want. When you look at it from a data perspective, from just an anecdotal perspective, as someone who's been selling for about 17 years, like if I am a walking, talking brochure, meaning I'm just talking about the PR the value that my products.

Would create if you're a customer, right. There's an inherent step that that customer has to take. They have to buy my stuff. So what value am I adding in the sales experience? Almost none. Right. So I think anecdotally, I don't feel like if I'm just walking, talking the product specs and features and benefits and all that stuff, like candidly, that's all stuff someone can find on our website.

[00:11:07] Luigi Prestinenzi: Seeing some of the data from Gartner, which is showing more and more. The buyers don't value that. And they're actually okay to go in a, in a, in an, in a virtual world to find that information themselves, then get it from a person. Right. So I think that's a scary, it's a scary reality for many sales professionals who are still thinking, you know, the order-taker mentality.

I'm pushing features on an organization, but I think one of the challenges and obviously the book, for some reason, the book does the book has created a lot of debate in the community and the sales community. Some people really love it or on the opposite. Some people really hate it. I'm in the first camp because I really liked it.

Like, I really liked the way it allowed me to think a little bit about using insight to create that value. Right. So. Talk to me about how you, because you've been, you've got you're, you're quite a carrier steel. You've carried a quota for a number of years. How have you been able to use the challenger mentality and create that buying experience that allows buyers to move away from the move away from the obvious need to the unrecognized?

[00:12:26] Jennifer Allen: So I love this question because prior to me reading or being trained on challenger, I actually really identified with the seller profile. That is the relationship builder. So for those that haven't read the book, it's like you, when you're backed into a tough customer situation, you either show up like our relationship builder, a hard worker, a problem solver, a lone Wolf or challenger.

And so I was not born a challenger. In fact, like in my personal life, I run from conflict. I hate to tell people bad news. Like I couldn't be more anti challenger just naturally. And so when I learned about challenger, it actually happened at the right time because relationship building was working really, really well for me.

And then 2008, 2009 happened, the economy fell apart. And all of a sudden these friends that I made at customers. We're nowhere to be found because they were laying off. People are getting fired or, you know, losing budget. And so all of a sudden it was kind of slapped me in the face that this isn't working anymore and I need to pivot, but I didn't know what to pivot to because what I would find is I'd ask a high performer, how are you being successful?

And they would just like, say these really unhelpful things, because it's hard for them to understand what they do that makes them great. And so part of the, like the criticism of challenges that I hear a lot. Is that people will read it and they say, well, I've already sold this way. There's nothing new about this, but that's kind of the point, right?

Like we did not invent challenge or we just use research to understand what were high performers doing in practice. And so a lot of times when I get into that dialogue with people, it's like, Great. You were one of those high performers that figured it out, but it doesn't negate its value for everybody else who does it.

So for me, it was really about understanding when I'm spending time with a customer. If I am just reacting to what they say they need, because I perceive that that means I'm being helpful. I'm falling so short on value creation. All I'm doing is to your point kind of order taking, right. And I'm being. You know, accessible, which isn't a bad thing, but it's not enough to drive a competitive, a wedge between me and the other person that they're evaluating.

So for me, it's given me structure to say, when I prepare for a customer meeting, when I deliver a customer meeting, when I'm doing a group meeting, I have to intentionally identify a belief or assumption that is causing them to believe they have a set of needs. That doesn't align with what I sell and until I disrupt that respectfully, but also with evidence, with insight, with information, I am only going to be at the mercy of hoping that they've defined a set of needs that we can win on.

Right. And so I think knowing what to be mindful of, knowing that I'm going to have to show evidence. This is a flawed belief or assumption because of this and then building the pain and making them uncomfortable with, if you don't do anything about it, this is going to fester and get worse that none of that came naturally to me.

So that's where I really drew from chow. I still continue to draw from it every day. When I prepare for meetings, I have to rewire my brain to think differently.

[00:15:21] Luigi Prestinenzi: Yeah. I love the, I love some of the things that you've, you've just talked about then, but I actually want to talk about some of that, because I think this is where.

In my opinion, right? I think this is where people get it wrong is they're thinking the challenger sale is about telling a prospect or a client, what they're doing wrong. Versus what you've just said is help them become aware of things they should be considering. That will allow them to achieve a different result.

Right. And I think this is where the misconception, in my opinion lies because no one likes to be told if you're a buyer, Hey, you've just made the wrong decision. Especially, you know, especially if they've been working on a particular project or on a transformation journey, and then someone says, Hey, you've just been doing it all wrong.

Cause you kind of insulting their ego as well. Right. And it can, it can lead to a really disastrous outcome where they just go, you know, I don't want to have a relationship with you. I've actually made that mistake before where I've, I've told a prospect something and I've probably communicated in a way that was you've made this mistake.

And therefore the relationship barrier just came up. There was a lot of relationship tension, and I wasn't able to progress the opportunity. So I would love to understand from your perspective, right? You talk about, you know, leveraging insight and helping them sort of challenge their belief system in a, in a positive way.

How do we do that? So for a sales proficient and listening to these guys, you know what I read the book, but I love what you're saying. I think I'm the relationship builder. I don't really fit that profile yet. What are some of the things that I can do to maneuver the sales process, to bring that insight and, and get them to start to see things a little bit different.

[00:17:04] Jennifer Allen: So, first of all, I love the story you just told because I committed that offense like a hundred times before I got it right. I thought, okay. Schedule the meeting, show them how smart I am. And then they're going to want to take more calls for me. And I wrote a post about this the other day. It was actually the complete opposite.

Right? What it ended up happening is I was talking at customers. They were completely tuning out and here I am thinking, I've just taught them. Obviously I'm going to win this. And it was just, it was completely wrong. It was in my own interpretation of what challenger was. So I love the story because I've lived that and I've got it wrong so much.

So what I, what I believe helped me get it right. Or right more often is challenger. Isn't telling some, someone something, right? Like to your point, when I say you're wrong, I'm right. I'm now creating an offense defense relationship with my customer that is entirely unproductive to a, to a partnership because now we're on two different sides of the table.

The way that I observed great challengers and action. Like one of the things they did is instead of telling someone this is right, and this is wrong, they first do really good discovery. This is another misconception about challenger that like challengers don't do discovery. I thought that too. You can't get anywhere if you don't understand who you're talking to and what they're trying to achieve, but it's the way that challengers do discovery.

They're not doing discovery to understand what the customer's needs are so that they can respond with a solution to those needs. They're doing discovery to look at two things. One is what is it that that customer is trying to achieve. So like, for me, I need to know, is it about. Market share. Is it about, you know, put new product growth, whatever the case may be.

I need to know what the end goal is, but I'm doing discovery on the needs to try to ascertain what is it that they believe gets them from a to B, because somewhere in that belief system, There's probably a piece of information or an assumption that they've made that may be outdated and they may just not have the most current information on it.

And so I'm not teaching. Here's how you get from a to B what I'm teaching is actually around the belief or assumption that underlies how they believe they get from a to B. And that's where you can introduce new information, new insight, new data. Completely empathize and understand. That's why the plan is what the plan is.

However, what many people don't realize is this thing down here has changed. And then your goal is to set off a domino effect, right? Because if the belief or assumption underlining, the strategy has changed, they themselves start to question the whole strategy. That's that to me is the key

[00:19:41] Luigi Prestinenzi: So what you're talking about is about leading them to that realization.

Not you telling them. And when they lead, when they arrive at that point of aha you've then created value because you helping them become aware of something they might not have been aware of before gage with you. And so that's quite a powerful, it's a powerful place to help them arrive to right. We'd also love to know, because I think, again, I I'm seeing some really in, in my opinion, I'll say this alarming sort of posts by some experts out there that discoveries, you know, there is no discovery stage of the sales process.

It's not a stage of the sales process. And I, I think, you know what, that's just a bit argumentative because, you know, I think even though discoveries happening throughout, there is a moment of time where you've got to be doing some form of discovery. But again, if I look at the insights, if I look at the, the whole premise of the challenger sale that discovery, where, when should it start?

Should it start before I engage with you? Should it start when I engage with you, like share it, share with us what you do to build that discovery.

[00:20:53] Jennifer Allen: Yeah. And I will say, I think there's differences depending on like your type of sale or what you're selling. So I sell on a very complex sale. Right? I could argue, you could argue if you're selling a transactional product.

Like, I don't know how much it makes sense to go as deep on discovery as I'm going to talk about. But I think for anybody where you've prioritized them as a target, someone that represents, you know, a really good potential fit for your company, I think we owe it to customers to your point to start discovery before the first call.

And what I mean by that. When I first started selling, you know, for like, we didn't have the resources we did today, we would have to start discovery on the phone. But now if I open up an annual report, there's always going to be a CEO level letter to shareholders that states, what is the company trying to do and how their strategy, what their strategy is to get there.

And so the, the other mistake I made a lot is I would take that as. This is just Bible, right? When in reality, you find that sometimes there's a statement up here and there's a different belief down here. And so the way that I would make that mistake is I would call them and I'd say, I understand you're trying to do this.

And this is how you believe you need to get there. And then I would jump right into my insight. What I've since learned is you need to really pause and allow for someone to disagree and open that up. I said, Here's what I understand so far in my own research, but I absolutely guarantee there are things that I've missed.

What's important that I've missed and opening that up to say, I don't assume I know everything. I think sometimes as sellers, we want to prove we did our prep or prove we're like that lazy, but I think you need to open up the conversation, but allow them to correct you on those items before you move forward into this.

[00:22:28] Luigi Prestinenzi: Yeah, I love, you know what, I've actually, I'm really thinking about this is good. This is actually really good because I'm trying to, you know, I'm trying to, now I'm thinking about application, right? Which is fantastic because you're creating value for me. It's about going. I do more research. So I have a point of view, but I'm not just saying, this is my only components say, Hey, this is the point of view that I've got, but also help me understand what other elements of the point of view that I might've missed.

Yes. So I think this is really awesome. And you talk about that research phase of looking at CEO reports, obviously for nested organizations. There's so much information in the public domain. What do you do when it's a private organization? What are some of the things that you look for from a private business?

[00:23:15] Jennifer Allen: Yeah, so I think one of the saving graces in selling today is that even if it's a private company and they don't have an annual report or a CEO leverage letter to shareholders there's a much higher likelihood, at least with the, the obviously I'm selling to salespeople. But they have a voice somewhere.

If it's LinkedIn, if it's, they're doing podcasts like this, if they're doing, you know meetings with potential investors or whatever the case may be, I just think it's, it's very rare. It's not, it's not never, but it's very rare today. I can't find something. That shows that executive or that company's perspective on what they believe they need to do.

Candidly podcasts interviews are a great source because we tend to get more human and how they're talking about it, as opposed to the rigid statements you find it like on an annual report,

[00:23:59] Luigi Prestinenzi: Really great insight. And all right, so I want to kind of break these down now because we're talking about okay, but a top of funnel, a bit about sort of we've, we've, we're leveraging a point of view.

We're getting a conversation. We may be having that discovery meeting. From it from your perspective and the one that you've used, some of this insight and that challenge, our kind of mentality, visit, just stop at that discovery stage. Or are you continuing to leverage that insight and helping them as you get closer to that point of decision?

[00:24:34] Jennifer Allen: I feel like you listened to all of my bad sales calls and are bringing up all the mistakes I've used to bake and it's making me very uncomfortable now. That was the mistake I used to think. You use insight to win over that stakeholder. And then from there on out, there's no place for insight. What I've realized is insight plays a role early, mid.

So early, we've already talked about right. Mid it's about now maybe I have an activated stakeholder, but now I need to help that stakeholders socialize that insight to everybody else who has an opinion on the problem, the solution, the vendor we pick. Right? So that insight becomes essential because that is our grounding element.

I have to get everybody to agree with this belief or assumption or this insight. And if I don't. Like candidly, I won't even get to proposal or solution phase because I know it's just going to break down anyway. So middle that's where insight plays a role. And then end is the one that I'm newer to like being consistent about, which is when you get to the end and you've agreed on a proposal.

We've all been in those deals where they just start to. Extended and extended it's taking time. And so the really interesting tactic I learned from challenger was this notion of cost of delay. So in the beginning, right, we're talking about cost of the problem, but now as we're getting, sitting and waiting, where we can really have an impact is to go back to that initial insight and say, remember who we talked about, you're losing.

You know, a thousand dollars a day for this, it's been 20 days since we initiated MSA review. So now you've accused this cost, like how do we create urgency internally? And so you're revisiting the insight, but putting an amount to the cost of the delay. Oh, I bet

[00:26:11] Luigi Prestinenzi: That's the clip, you know, that, that is, that is an incredible cost of delay.

I think this is a mate because you're right, because I think, and then what we find is because. That, when that momentum starts to slow down is a lot of people then start to do the old I am following up on. Right. I'm just touching base bubbling these to the top of your inbox. And for me, I hate that because it's like, what value are you actually creating?

What you're doing with this is you're actually saying, Hey, when we spoke about this, this is a priority. This is what it's costing. And it's again, bringing that to the top to say, easily steal a priority. And if so, we've got to take action because every day we don't, it's having a further negative impact on the business.

Love a lump. Totally love what you're saying here. Yeah. You know, I, I was listening to one of your podcasts and I actually want to get a bit of feedback on coaching on this. Right. Because when we think about in the buying process, especially in enterprise, maybe not in the, you know, single stakeholder decision deals.

Right. But definitely in enterprise. And I think Gartner released some data that says. Nine to 13 stakeholders are involved in a decision making process. And we seen that buying by committee, but often, you know, there's got to be a commitment to collaborate, commitment, to gain consensus internally, the commitment to change before they commit to budget.

Right. We know that we know there are certain stages of commitment and organization needs to take for me. I find that. That commitment for alignment, you know, getting alignment within an organization can sometimes be difficult, especially when people have conflicting parties and. Often when we're selling something to an organization, we are selling an unrecognized need, which therefore it's not budgeted.

Right. So they're going to go have to create the budget. And in some cases, that budget that we're trying to create, another stakeholder sees that as an opportunity to go, well, this is my opportunity to get some budget for something that I want. Right. So now we've got a very unique boardroom conversation, huh?

Your podcast, discuss that question. That alignment question is everyone on this call or is everybody within this room align with the strategy that we're working on? Talk to us about why that question and understanding alignment is really important when trying to progress a deal to that point of decision with multiple sites.

[00:28:45] Jennifer Allen: Yeah. So I love that question. I'll nerd out for a second and then I'll get real tactical again. So when we studied actually what happens when you have a customer who sees value in what you have to offer, right? Like I want to buy from you, but when you look at the number of stakeholders that get involved, if you have one stakeholder and they see value in what you do, you have like.

Some percent chance that they buy that's logical. That's not earth shattering. Right? But you get down to six stakeholders, which is far less than what we've seen. We've tracked it to be 11.2 in our most recent study, I think was 2019. When you look at six it's down in the 30% range. Right. And it makes sense.

And we had we did a webinar last week and we had one of our attendees raise this. So I want to give them credit. I did not come up with this. They said, A great way to think about this is pretend you're going to order pizza with 10 people and everybody has to agree on the toppings. What do you end up with?

You end up with cheese because cheese is the only thing that doesn't alienate somebody or they're not allergic to, or whatever the case may be. It's the same thing with B2B buying. Like we end up making decisions based on the lowest common denominator, which means we often just settle on what we're currently doing and.

Yep. And so the reason it's important is because when you just get 10 humans together on any topic to try to make a decision, it's hard, let alone when it's a massive capital investment. And so what's really key here is, is actually less about aligning on the solution and more about aligning on the problem.

So I would always seek agreement on, does this feel like the right solution to pursue. But what I, what I missed is oftentimes people don't voice up until you're off the line that this isn't really, even the problem I want to solve to your point. And this came up on a call. I did about two weeks ago, and we had this debate around, like I explicitly asked, like, what is the problem?

We've all agreed that we're solving. And it was like L and D sales leaders, business leaders, private equity owners. And that question alone was 20 minutes of dialogue because half the people wanted to solve for retention, half the people wanted to solve for new logo acquisition, and it's like, it's all sales, but it's different flavors.

And so I knew as much as they had set the agenda, we want to see your solution because we're looking at another vendor. We want to compare the two I had to have, like what I view as the discipline of taking control to say. I'm going to take control of this agenda. You don't even know what you want to buy.

I can't propose a solution for that. So getting agreement on the problem to me is the thing that I always use to screw up and have since really tried to put discipline around.

[00:31:10] Luigi Prestinenzi: Yeah, we are nerding out here, right. Because it's gold. You know, I just want to style now and, and add some of these strategies and tactics that you talking about, but, and when you talk about that alignment, How do you then circulate it? So, because often you might have a great meeting, you might have multiple stakeholders in, as you said, you know, that's a lot, I live in 0.2, et cetera.

How do you then circulate? Post-meeting the way to confirm I've got my own, but I'd love to hear how you, how you have done it to sort of say, this is what we discussed, and this is what we've agreed about.

[00:31:45] Jennifer Allen: Yeah. So two things that I always try, I don't always achieve, but I always intentionally tries on that group meeting.

I'm trying to manage my time. So I get them to either agree that we disagree and we're not ready to look at a solution and we need to go back and learn and hopefully learn with me. Or two, if we can get to an agreement. We also try to get to an agreement of what happens if we do nothing. So your audit, your customer's going to want to know how do we fix the problem?

We finally have agreement. What do we do? That's a place where I think we have to resist the urge to jump to solution and say, before we get there, let's talk about what happens if we do nothing differently, because doing nothing is a complete possibility, right? I know it. You know it, your boss knows.

Let's address it and then say, and get agreement on what does it cost us to do nothing. Then that's what I'm socializing, right then I've said, now I'm sending out an email to everybody in the audience to say, here is what we agreed the problem we're looking to solve it. Here's what we agreed is the cost.

If we do nothing now in our next conversation, we're going to look at what is the, you know, three or four steps we're going to take in working with you to solve that problem and reduce that cost of nothing. If anyone disagrees. Re email me independently, right? Like, don't feel like you got to have this back channel conversation.

And so what I'm trying to walk into that next meeting with is here's the problem. And my, all my slides start with one page summary. Here's the problem we agreed on. Here's what we agreed. It has going to happen. If you do nothing about it. Now let's look at a solution. And the reason I do that, So by the time we get to that pretty cost page, it's not the cost versus nothing.

It's the cost versus the cost of it, of doing nothing. And then they have a comparison point.

[00:33:18] Luigi Prestinenzi: Yeah. I think I love that. And I, I think from what I'm taking away from this, right, it's transparent. You're guiding them through the process as well, because that's the other thing that I find that often when we're helping our buyers arrive at a point of decision, they're not buying what we sell all the time.

So they don't always know how to. Certain things, right. How to get that alignment, how to do that cost assessment so that they can see the business case and the Richard burn on that investment that they're going to make versus a cost. Because there's always that equation that's going to be had that somebody is going to be asking the question, can we achieve what we need to achieve without making this investment?

Right. And that's, you know, commercially, most businesses should be having that conversation. So I love the way that you're talking about gaining alignment and trying to understand, are there any things that will concern, not have alignment so that you can address that before going to solution? And I think the other thing that I've heard as well, You're being really disciplined to hold back that final proposal to make sure that when you do put that proposal in place, you've got consensus, you've got alignment and you've got a clear understanding of the problem that the business is looking to solve.

So therefore your solution does allow them to see how they can solve that problem. So I absolutely love the sales process that you've shared with us. I think I've had, I dunno over you know, was the passing 170 episodes? I think you're actually going to be my first guest that would probably come on for a second episode

Because there's so much content here. I think for sellers right now, like this is good content. This is actionable content that hopefully my listeners are looking at this. You know what I'm nerding out as well. I can see applications of this. So I just want to say thanks for the content that you share with us today, but before we let you go where's the best place.

And I will put in the show notes where they can find your podcasts because it's a great podcast. We'll listen to it every month when it comes out where can they find you? And where's the best place for them to engage.

[00:35:24] Jennifer Allen: Yeah, so I'm big on LinkedIn. I spent a lot of time there. So Jen Allen, LinkedIn, you can find me pretty easily with Challenger. And then to your point, it candidly, the whole idea of the Winning the Challenger Sale podcast is not to go over the stuff that was in the book. Everybody can pick up the book and read it. We don't have to teach people like it's not a, it's an, a bedtime story time. What it is very much about is I think we heard a lot of people saying I read the book, but I still don't get how to do.

And so we have conversations like this, where we break down things like discovery, negotiation, running group meetings, and just say, what is it? What is it not? And candidly, a lot of the conversation is me just sharing my experience and stuff. I got wrong and what challenger taught me to do differently. So definitely encourage you to check it out.

You'll hear lots of perspective there, but we'd love to connect as well.

[00:36:04] Luigi Prestinenzi: First of all, Jen, I just want to say thank you for the contribution you make to our community, because again, have personally taken some of the tactics that you've talked to. Implemented in my role and I'm seeing a benefit to that.

So just want to say, thanks for coming on the podcast.

[00:36:20] Jennifer Allen: Thank you so much. And thanks for asking some really great questions and nerding out with me. It's the most fun part of the job.

[00:36:27] Credits: This show has been recorded remotely produced by Sales IQ Global, audio editing and music production by Stefan Malliate. Show notes by Victoria Mathieson and graphic design by Julie Marshall.

Don't forget to leave a rating and review on your podcast player. And if you want to find more about the programs that we offer at Sales IQ, head to

This episode was digitally transcribed.

apple podcast icongoogle podcast iconspotify iconrss feed icon

Ready to grow and scale your revenue?

By clicking “Accept All Cookies”, you agree to the storing of cookies on your device to enhance site navigation, analyze site usage, and assist in our marketing efforts. View our Privacy Policy for more information.