The Ultimate Win-Loss Guide w/ Ryan Sorley | Coffee & Compete

Hey, everyone. Welcome to Coffee and Compete, the show about the news, gossip and tactics of competitive business strategy. I'm Your host, Adam McQueen joined with me as always. The guy at Clue that uses Clue is Hunter Stones. Hunter, what's going on, buddy?

Staying alive, my friends. Staying alive.

Like.

Like the Bee Gees.

Like the Bee Gees, exactly. Joined with us today is a very, very, very, very special guest.

You missed a very in there.

Yeah, sorry. Very, very, very special guest. Future best selling author of the book Blind Spots, VP of Win Loss and co founder at Clue, it's Ryan Sorley. Ryan, thank you for joining us.

And what's on your shirt there? Adam did it.

Teddy bear in a cool hoodie with a basketball says Chinatown.

I love it.

I'm trying to fit in with the use. We've got a lot of young folks in this office. I hit 30 and I need to hang out with the 20 year olds more and like blend in like camouflage.

Did your stylist for the show pick that out for you?

My stylist is Grayson and Grayson's 26 going on 46. So yeah, it's, it's an uphill battle for me right now.

I love it.

We're going to dig into Ryan's book because it's coming out April 2nd and everyone should read it. We're going to get into everything that's within that book before we do some more housekeeping as well. Ryan, you're running a workshop in person with folks. You get a signed book with Ryan too. Workshops happening in London, April 10 and Boston. Did I do that right? Boston, Boston, April 15. And we're putting Ryan to work here too. It's not like he has other responsibilities other than cranking out content for our team. He's also running a power half hour for the Compete network community as well. And that one is on April 4th. So we got a lot on the go. You know what, another one as well. Trends Report. We're recording beforehand, but this will be live. We, we have our 2025 win loss trends report where we broke down how different companies are running their win loss programs. The strategic priorities they're focusing on, where they're putting budget, all of the above. It's awesome. Go check that out as well. Got all out of the way. Ryan, tell us about the book.

Well, the book is called blind spots. 250 pages of win Loss goodness. It is really helping to frame what Win Loss programs are all about. Bringing people through all of the key steps associated with building a super valuable, actionable, insightful program. So it's a bit of storytelling, a lot of stories woven into the fabric of the book to help bring things to life a bit. It's a bit of strategy around how to approach leaders within your organization about how to push a win loss program, get it going. So it's, it's something for somebody who is running a mature program today. They can get something out of it as well. As for people who are brand new to the win loss programs, never run one before. Maybe they're being asked to do it for the first time. So, yeah, a lot of win loss love in there. And it's available April 2nd.

Ryan, I got to ask the competitive differentiation question. There are some pretty good win loss books out there. I know Ellen Naylor, she put one out a few years ago. I've read it. It's incredible. What was it that sort of like set the scene? Like, why did the world need another win loss book and what makes yours different?

Well, Ellen's book as well as Richard Schroeder's book were books that I read way back when I was looking to figure out this whole win loss world, kind of build a business out of it. So they were playbooks for me and I tooted their horns when I sent out my own LinkedIn announcement about the book coming out. I think this book is a little bit more of a modern take. Those books have been written, they were written a while ago and what I was hoping to do with this book is maybe make it a little bit more contemporary, a little bit edgier with some of the stories and funness that's within the book. And yeah, things have evolved and the win loss space continues to evolve. So with that, we need to continue to evolve our thinking and the content that we're creating to keep up, keep up with things. And frankly, like, this book is something that's been worked on for the past four years. We need another book that will come out after this one that takes into consideration a lot more Genai stuff, a lot more about how the world is changing so rapidly. So I think there's another book here as well. There's an add on to Blind Spots. Blind spots part 2. AI.

You heard it here first, folks. This is Win Loss part of the Win Loss trilogy.

The trilogy.

Yeah, exactly.

Ryan, you mentioned, and this is one thing I love within the book too. Stories, stories, stories, stories. What is your favorite story within the book?

I think my favorite story is the story I open the book with, which is my origin story. And, and when I was working at GARTNER and prior to that, a company called AMR Research. I worked with a lot of retail leaders, people who are chief information officers, people who are looking at buying technology for their organizations. And on one particular day, I was sitting with a CIO of a major shoe retailer, actually out of the UK who had a North American office in Boston. And, you know, I was his trusted advisor, helping him navigate this big $40 million retail ERP decision that they were looking to make. And he was complaining to me, opening up about how dissatisfied he was with one of the providers who was his preferred option. And they kept showing up with 10 different people who couldn't answer any of his questions. Those people would leave, and 10 more people would come. I called the corporate clown car in the book, and none of those folks were able to really get him to where he needed to be. So he opted for the company who was not the front runner, who was kind of second, and he chose them ultimately. So the company he preferred lost this $40 million deal. The company he didn't prefer, he chose because they have their act together. They were able to answer all of his questions. They were clear about the roadmap and vision for where they were going. They had great client testimonials, great references that he could speak to. So his. His perspective changed. And it was like that moment where I realized, geez, if I had the power of taking this information and giving it to that front runner, the one that ultimately lost the deal, to help them change the way that they do things, or at least take that story and consider making modifications, they could actually raise the bar, and they could continue to raise the bar over and over and over. When I went back to the CIO and I asked what their reaction was to the loss, he was like, they didn't even ask. They just moved on. So, like, why? You lose this $40 million deal, and you don't even take the time to really dig into the why? So I saw an opportunity there, and that led to rolling out a double check. And where I am here today with Blind spots, the book. So that's my favorite story, Adam, is that first story.

What part of the book took you the longest to write? What section did you go back, revisit, tweak, stare at a blank page for hours on end? I want to know.

I mean, the whole thing, honestly, like, you know, it's. It's. You want to make sure that you're sharing sage advice in the book and that you're not shortcutting things just to get a chapter done. So a lot of it was going back, making sure that it made sense, that I believed strongly in what, what advice I was providing in the book, that it was written in a way that was clear, clear and concise and you know, like hit, hit the point. So I, I think, I don't know if there was any particular section of the book that took me longer. There were certain points that took longer to unpack. Like there's a section within the book which talks about this concept of a mountain range. And mountains, you know, they have high mountains and low mountains. Like it's mountain range, you have high peaks and low peaks and, and the concept there is when you're going out there and conducting win loss interviews, those peaks are your objectives. And when you go into these interviews, you really have to have a plan. Like I want as much competitive intelligence as possible or I want to know as little as possible about our sales experience because I don't really care about that. I just care about competitive intelligence. So you've got a low peak and a high peak and then within those mountain mountains you have snow caps, right? Which represents like smaller portions of the mountain mostly. And those are online survey opportunities. Like I just want to kind of dip, dip into what's, what's happening here. I want to send a survey out to collect some information. And the base of the mountain is that deep, detailed interview where you're going to ask open ended questions and connect dots and be really interested and passionate about what the interviewee is sharing. And then the valley below is where all of that stuff kind of comes together to create insights. You know, it's like connecting the dots to be able to drive insights that lead to actions that lead to change. So I know that was a long answer to your short question, but I think that concept in using a mountain range took a while to formulate. So I'll point to that.

Ryan, one thing I'm curious too is like as you were putting together the book, by the way, how long did the book actually take you to write? Was it something that you kind of like you did in a short period of time or was this an extended writing process?

It was a four year period and I've had a lot of stuff happen in the last four years. So it wasn't like sitting down, steady flow writing. I think that if I had nothing else to do and nothing else going on in my life and I just sat down, I could probably have knocked it out in eight to 10 months. There's a whole publishing process, technical editing, there's A lot that goes into a book above and beyond just writing the book. But yeah, I was probably over that four years, a solid, eight months of work.

Okay. And the thing I was really curious about is like as you were writing the book over that period of time, did you have like an idea of, okay, this is the, this is like the one or like two things that I really want someone to take away from this book. Like obviously there's a lot of content. We scroll through it, it's a thick book, there's a lot in there. But what was the idea behind like the one or two things that you really wanted someone to take away from the book after reading it?

I think that the one primary thing was to empower people. Product marketers, Competitive intelligence leads win loss program owners to have almost like a bible that they could turn to to really understand like how all of the different aspects of a win loss program are connected and the logical flow of things. So it wasn't so much like I wanted them to walk away with this thought. It was more about, I wanted to educate people based on all of the things that we've done and developed over the last 10 years to create what we believe is the best in class program. So I would say like that's not, it's a non answer to your question. But yeah, I can't, I can't pick one or two specific things. It's more about like the story of the, of the, of the process.

Okay. So it's less of okay, great, I, I have my takeaway. This one's going on the shelf more. This is something that I expect to come back to time and time again as a reference guide for how to do winloss. It's, that's kind of what I'm hearing.

Somebody should read it and cover to cover and then, yeah, be able to go back to it if they need to. I think there's a lot of product marketers, competitive intelligence folks out there who have been put in charge of running a win loss program and they struggle to get others to come along or to do the things that they need them to do to, to create a best in class program. And I think people need a reference guide to be able to say, hey whoever, you know, head of sales or head of customer success or head of marketing. It's not just me asking you to do something. Look like this is a best practice. Look at page 265. Now look at page 163 where it clearly outlines that this only will work if we have buying from the sales organization, because we need you all to be in on the learning objective development, the outcome, the enablement associated with the outcomes. And then also like we need you to be a partner in making sure that we're asking people to provide feedback and you know, connecting us with those people, making sure they're the right people. So I believe our clients and people who are running Win loss programs are thinking about it, need that thing to be able to go to somebody else and say, hey, this isn't just me asking you to do something. Look, here's a story, here's another story. Here's another story. So I think it's like ammunition for them to be able to back them up when they're making asks within the organization.

So you mentioned there prime marketers folks often get put in charge of win loss and maybe they don't know what good looks like or how to really drive impact or change. What is an example that you've seen firsthand of someone? The hero's journey. You mentioned a person taking on Win loss. Can you give me a specific example or story of someone that really was able to enact impactful change in their business because of win loss?

I think the story that I'll share here is it was a cybersecurity company that we, we work with today. But the story is from, from many years ago and the person who is leading the effort was super smart and they've gone on to do great things including being a CEO of a software company and they were very clear on what their objectives were for the program. So thinking about a wind loss program, a lot of people, you know, they kind of know what they're looking to get out of it. We need to educate a lot of folks on the possibility of what they could get. This person was very sure of what they were looking for and they were looking for data to serve a very specific purpose, an agenda that they were looking to push within the organization. They were having trouble with pricing. Their salespeople were having a difficult time explaining it. Customers were having a difficult time understanding it. It caused this, this kind of lack of trust. There was this lack of transparency. It was just a bad situation. And they knew that if they solved, he knew that if they could solve that problem then they would win more deals and ultimately be in a better place. So he used the data collected to be able to show leadership that they had a big pricing problem. They actually gave him budget to hire a full time pricing manager that when hired enacted a new pricing model that totally turned things around. It included the hire, the budget for the hire, it included the new model, it included enablement that really pushed this idea of change within the organization that led to a tremendous growth as far as competitive win rates were concerned. So that's one of many stories about how a smart, talented product marketer took the data to really turn it into action that led to positive change for that cybersecurity company.

One, I love that story. Two, I think this is kind of in reference to. There's not one or two takeaways from this book because something that I've heard you say many times rhyme like win loss is sort of this living breathing entity within an organization. And so there's not just always going to be like, here are the obvious outcomes, it's going to shift. We talked to Dan from Salesforce a couple weeks ago. He's like, agent force is really important to us. So my win loss is geared towards that. So it's always like moving around. I don't think there's always going to be. We know that there's like the typical things you want to look at like sales processes, product roadmap, pricing, but like you really can orient it to what matters most in that moment too. And so I love hearing those specific stories. Like it's not necessarily like that outcome might be different to another person that's leading a really successful win loss program.

The other one that, that a lot of people don't do but should is to use your win loss program to verify data that's coming in from other sources. So, you know, we all at Clue have a compete channel. When we hear something competitive, we drop it in Slack and we, we, we all jump on it. Oh my God, this competitor is discounting that competitor has an integration, whatever it might be. And you know, I, I look at that as a researcher, I'm like, well that's sample size of 1. Is that true? Is that not true? And Hunter over there, responsible for competitive intelligence, has to figure out, should I put that, is that a thing or is that not a thing? Should I put that in a newsletter? Should I put my stamp that this has been verified on that piece of data or not, right? So when loss research is a way to, to do that, you can look at your gong calls too. But if you look at your win loss interview data, you have a source to say, yep, that's true. Because I've actually heard that five, five times in recent interviews or I've heard that five times in recent gong calls. So that win loss intel direct from buyers is so Important for turning kind of false, fake news into verified Hunter approved insight that people can take to the bank. So I think, you know, that's not like a, a use case related to collecting product feedback or understanding how the sales team is performing. It's more so focused on like how do I verify the data, the great data that's coming in from all kinds of places to back it, to make sure that it's something that, you know, Hunter feels really strongly about, that it's a thing and that we should push it. And the other piece is, does that thing, now that I've verified it, I'm Hunter, I've verified it. Does that thing apply across the board to all of the products that competitors is offering or all the organizations that it's serving? Is that just an enterprise level thing? Like maybe they're doing some sort of an integration for free at the enterprise level or is that something that they're offering across the board? So Hunter has a super tough job of figuring out like is it a thing and where does it fit? And I think the win loss intel that Hunter and our team is collecting really helps to ensure that what we're sharing out and putting our stamp on is reliable intel. So that's just like another use case that more organizations should, should consider.

It's so true. It's so true because I can think of many examples at Clue where there have been things that have come up anecdotally or even, you know, go into a competitor's website and you make an assumption about this could be a differentiator for us, or hey, maybe this is a differentiator for them that we have to be able to. Objection. Handle. But then going back to the data and the win loss interviews and you know, coming to terms with either this is something that's showing up, we're asking about it explicitly, or it's not. And then that helps kind of point you in the right direction or at least you know, cement you in a little bit of reality. So that is very, very helpful.

I think this is where Hunter and I, you know, have had, have had some, some one on one conversations about like data that's being pushed out. I'm like, Hunter, I'm not sure. Are we sure about that?

That's where I have to put my foot down. That's where I've got to give that Hunter stamp.

So I, I think it's just a really important use case.

How do you think about, I guess different types of competitive intel data in that case? Like this was, this is kind of a top of mind. I think for a lot of competitive intel practitioners, win losses sort of among a whole flurry of different types of competitive Intel. Where do you sort of see it fitting into a broader, sort of a broader set of types of data?

I think that we all have to look at all of those different sources of competitive intelligence and we have to assign them a reliability score. And we have to look at things like how reliable is the source of data overall and then like how easy or difficult is it for us to verify. So when you look at something like win loss data, it's hard to get. We're getting it directly from the source. We're tapping into the source, the person who has all of the intel super reliable because we of the source. And in the quadrant of competitive intelligence reliability, it should be the top right hand corner, kind of like the Gartner magic quadrant up top hand, top right hand corner where you have other data. Like, I don't know, something somebody posts in Reddit or Twitter, which is questionable. Like, that's data. Point of one. I'm not sure who this person is. They could be, you know, a competitor writing something bad about us. It's like fodder. Maybe they have a burner account. And then you look at things like G2, which is great Intel. We know it's coming from the buyer or customer, but we also know that the vendor probably gave them a $50 gift card to write that review. And you know, it's void of all of the real reviews, right? All of the stuff that the real people out there who are not getting paid to write a review feel about about each provider. So the matrix that I Posted today in LinkedIn really places all of these different sources in key areas associated with reliability. And I think each person who owns a compete program really needs to think hard about all of the data they're collecting and apply scores to that data so that when they're sharing it out, they could say, hey, this is a level four piece of information which is actually really reliable versus a level one. Or I can't remember if I flipped that level one piece which is unreliable. But, but like when they're, when they're pushing the information out, it's like you can trust this or maybe you shouldn't trust this, but I want to share it with you. So that's, that's my view on, on like where it fits top right hand corner and like how everything else ultimately needs to fit into this matrix, this quadrant.

I am just impressed that you know what a burner account is Ryan that's you're hip to the trends, my friend. 1 this is awesome. Getting to talk to you. Get a little peek inside the book again, folks. Hold it up for the folks that are watching on the YouTubes here. Ryan, go get blind spots. April 2nd Bang. And join Ryan if you're in Boston or London or in that area, join them for the workshops. Ryan, give us a little teaser. What can folks expect? Why should they come to the workshop?

So the workshop is really focused on programming. There's a lot of people who venture into win loss programs and they're not quite ready and they start to find these friction points within their program. So what we're going to be talking about is what organizations need to really build a best in class win loss program. We're going to be going over our readiness assessment which is a model that we created last year to help support that process. And we're actually going to be taking people through a self assessment so that they can get a score immediately to figure out like where they fall on the level of maturity and then also like what things they should do to improve their maturity score. So it's going to be a great event. There's also going to be networking. I think food and drink involved as well. And yeah, copy of the book 100.

If you anyone came to compete week in person. Not to brag. I mean I really wasn't a part of a lot of the event planning but people knocked it out the park at Clue. The experience was awesome and it's gonna be just the same for these two workshops. So make sure you come hang out with your peers. Meet Ryan and yeah, have some food and drink.

Ryan, thanks for coming on.

A pleasure. Thanks for having me.

And we'll catch everyone next.

Sam.