Burn The Playbook - B2B GTM Strategies with Marc Crosby

Win-Loss Analysis: How to Fix It w/ Cian Mcloughlin

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0:00 | 45:36

Win-loss analysis for B2B sales. Learn how to capture clean, candid buyer feedback, stop guessing in CRM, and turn every pursuit into future wins. Author of “Rebirth of the Salesman” Cian McLaughlin joins Marc Crosby on Burn The Playbook to share 15+ years of hard lessons from enterprise pursuits at SAP, Cognizant, and Trinity.

What you’ll learn

  • Why seller self-reports distort win-loss data and what to do instead
  • How to set debrief expectations during the cycle to boost candor and participation
  • The “separation principle” for unbiased feedback buyers will actually share
  • How to triangulate truth across multiple stakeholders
  • Three frictions that kill enterprise deals but never show up in CRM
  • Why risk beats price, and how to surface value drivers that matter
  • A simple post-sale loop that turns insights into actions buyers notice
  • Where AI helps in prep and follow-up, and where humans must lead

Chapters
00:00 Intro
00:31 Meet Cian + why teams guess on win-loss
01:09 The Emperor’s-New-Clothes problem in sales
04:57 Stop making AEs pick “reasons” in CRM
07:27 Set debrief expectations early
10:33 Why rigorous debriefs impress buyers
12:22 Clean intelligence in practice
15:03 5 principles: context, value, teaching, co-creation, professionalism
18:22 Professionalism as the true differentiator
19:01 3 frictions CRM misses: oral phase, risk, value vs price
23:22 How many deals die in the first meeting?
26:31 After the win: manage risk like an incumbent
29:58 AI with a human in the loop
33:29 What AI still misses
35:59 Burn It or Build It: 10 hot takes
43:32 One thing sales leaders can do tomorrow
44:42 Where to find Cian

Who this helps

  • Enterprise sales leaders and CROs
  • AEs, SEs, and pursuit teams selling complex deals
  • RevOps leaders fixing CRM noise
  • Founders selling to the mid-market and up

Guest

Host


  • 1: Your CRM isn’t truth. Here’s how to get real win-loss signals. #WinLoss
  • 2: Stop guessing why you lost. Ask buyers the right way. #B2B
  • 3: Risk beats price. Learn to surface and share it. #EnterpriseSales
  • 4: Make AEs stop self-reporting reasons. Create separation. #SalesLeadership
  • 5: Close the loop. Show buyers what you fixed. #SalesProcess
  • win-loss analysis, B2B sales, enterprise sales, CRM accuracy, buyer feedback, stakeholder mapping, deal risk, value vs price, oral presentations, pricing vs value; sales professionalism; co-creation; RFP response; QBR; sales risk; oral presentation phase; AI in sales; Trinity usedtrinity; Cian McLaughlin; Rebirth of the Salesman


Views expressed are our own and do not represent any organizations

© 2025 Digital Rebels Consulting. All rights reserved.


Digital Rebels Consulting (00:01.051)
Welcome in I'm Marc Crosby. This is burn the playbook My guest today is Cian McLaughlin who was the author of Amazon number one bestseller rebirth of the salesman and one of the most recognized voices and modern B2B sales a two-time LinkedIn top sales voice and three-time top 50 sales blogger can spend a decade in senior sales leadership roles at Cogniz and SAP before leaving the corporate world to found Trinity. Hey Cian Good welcome

Cian Mcloughlin (00:25.645)
Hi, how are ya?

Digital Rebels Consulting (00:28.546)
So you worked at SAP you left the bill Trinity at what point did you realize that sales organizations had no idea? Why they win or lose deals and maybe why nobody cares?

Cian Mcloughlin (00:41.194)
I sat around in a lot of meeting rooms after we would get that unpleasant call telling us we had been unsuccessful in the sales cycle. And I looked around and we were usually discussing and debating why we'd lost. And we would usually arrive at a plausible narrative for what had happened. We didn't really have our executive alignment lined up. they were leaning towards Oracle. it was a race to the bottom from pricing perspective.

And then we would just create a consensus around a couple of these broad themes and that would become the accepted narrative for what had happened on that deal. And that would happen again. And it would happen when we won. It wasn't only when we lost, we would just make shit up and agree it amongst ourselves and move on. that just struck me as the craziest thing in the world because we put so much time and effort, we'd invested, you know, been very professional right the way through the sales cycle. And then at the, at the very last step of the process, we were just kind of phoning it in and making stuff up. And so I started.

started chatting to other folks in other companies like know IBM and Oracle and elsewhere and I said how do you do your post sales analysis and then it was effectively the same we were all just making it up and so that was the kind of the Emperor's new clothes moment for me Marc where I was like my god we're as an industry we're just missing a huge opportunity here and so it set me off on this weird wild path I've been on for 15 years to try and change that.

Digital Rebels Consulting (02:00.386)
Yeah, it's definitely a worthwhile problem to solve I've been there in those meetings and I'm not gonna say that I didn't make stuff up at times but you can always just push the blame to I guess where wherever you see fit and Kind of everyone just nods their head. Yeah. Yeah, it's price, you know, they're always undercutting us or blah blah blah blah blah or some some reason I guess either to make you feel good or to save your job

Whether as a salesperson or as a sales manager or maybe in an executive leadership and then you just move on to the next deal or the next customer and you probably tend to make the same mistakes. Is that typically what you find in your work?

Cian Mcloughlin (02:27.608)
Yeah.

Cian Mcloughlin (02:34.72)
Yeah, very much so. And I think, you know, if for smaller deal values, the default is there's a drop down list in CRM when we're closing out an opportunity with, you know, five or six or seven criteria and you pick one and that then tells you, you know, why you've won or lost. And salespeople being salespeople, invariably, we pick the one that's going to give us the least amount of additional scrutiny after the fact. you know, last do nothing. Okay, I'll pick that one and we'll move on to the next one. And so then all these organizations, I've

spoken to, you know, achieve.

operations people and they're like, we're losing deals for all of these reasons. You know, there's three or four things I'm like, have you scrutinized that? And they're like, what do mean? Cause reps will pick the path of least resistance. And so suddenly we're have this skewed data set that's telling us we're, never losing to competitors because if it leaves the competitors immediately, there's five other pieces of information and red flags pop up and I have to have a conversation with someone else. So I think, you know, both at the enterprise level and at the kind of the run rate SMB level, we've, we've unintentionally

built a system that allows us to be very vague and unstructured as to why we won or lost and then we don't really capture any of the value at the end of the process and we just immediately move on to the next one and dust ourselves off and I think as an industry we thought that was the only way to do it but fundamentally that's wrong. In that last mile there's so much value on the table that you've earned the right to you just need a better mechanism to capture it and actually interpret it.

Digital Rebels Consulting (04:07.615)
So what does that look like? I I've been in Salesforce for many, many years and I know that dropdown box and you just basically, you can either just pick one, just to pick one to move on with your next task of the day, or you just pick one that's convenient for you. So how do you shift or change organizations and account reps and AEs to pick the right one? I don't know. How do you, how do you structure that?

Cian Mcloughlin (04:29.42)
Well, I yeah, I think the reality is it's not the job of the AE to pick the right one because the reality is the AE is far too close to it to actually determine exactly what happened. so

And here, and this is the critical thing, and I'm glad we got here early, Marc, in this conversation, because this is the juicy bit. If as an organization, you believe you've done a good job, if as an organization, you believe you've been professional in your approach to the sales activity, then you've earned the right to capture some feedback. Then you need to ask yourself the question, do we believe that we can do that ourselves, or do we want to get an independent third party to help us with this? And there's pros and cons, obviously, from a cost perspective and effort, whatever. But irrespective of whether you use an external third party or

an internal resource, you need to create separation for the customer between the people they had the interactions with and the feedback that you actually want to capture. So if it's an internal system or process or person, it can't be coming from the rep because if it's coming from the rep, you're immediately going to skew the quality of the feedback you get because because

people giving feedback to other people, where, you know, there's a little bit of EQ and so I don't want to hurt your feelings and so I'll default to price or I'll default to something else. Whereas if you create enough separation and you let the customers know, we would really appreciate you being candid and honest and constructive.

Then suddenly it's like the truth serum hits and they're like, okay, you really want to know. And then, and then you, and then the good stuff flows. And so that has been the real moment for me over 15 plus years. It's that irrespective of whether it's, you know, an internal resource or an external organization, you need to create separation. then depending on the size of the deal, you know, if it's a very large, very strategic deal, it should be done as a, as an in-depth interview. If it's a, if it's a run rate deal, there's a bunch of great tools out there that can help

Cian Mcloughlin (06:23.234)
you to actually capture feedback in a granular data driven but also qualitative as well as quantitative way.

Digital Rebels Consulting (06:32.785)
Understood. And I guess on the other side for the customer interview process, how do you guarantee that they're answering correctly as well as far as providing the most accurate feedback? And it's not just based on one person's opinion.

but as an organization as a whole, far as that decision, how it was made, because as we typically talk about, there's a lot of different people that are involved in deals. think the number's up to 10, 12. So what does that look like as far as triangulating what the actual reason was?

Cian Mcloughlin (06:59.128)
Yeah.

Cian Mcloughlin (07:04.076)
I look, it's a great question. And I think, let me take a step back before I answer that. The first thing you want to do if you want to get really honest, detailed feedback is set an expectation during the sales cycle that irrespective of the outcome, we would really like to do a proper debrief at the end of this process. so you're, you're setting the right tone. You're letting them know this is coming. So it's not a surprise to them because too often what happens is we lose a deal and then we decide we want to do a debrief and the customer is a little bit gun shy and they're a little bit uncertain about, what is this and what's

four etc. So as a

As a way of setting their mind at ease, you let them know that irrespective of the outcome, we would really appreciate the opportunity to do this. The other thing that does is during the sell cycle, that immediately differentiates you in terms of your professionalism and your attention to details and organization. So you get a level up just on that basis, but also the participation rate goes up significantly as well. The second thing that's really important to do is let them know what you're gonna use the feedback for and what you're not gonna use it for.

cases they've built a level of rapport relationship with the sales rep. So if they think this is going to be used to throw a rep under the bus or point the finger of blame, immediately people feel a little bit uncomfortable with that. So they need to understand that this is actually going be used as a mechanism for us to test and prove what we do to get better, to find gaps, to learn, to extract value from our cost of sale. But more importantly, that even if we didn't win it this time around and we have an opportunity to re-engage with you in the future, we'll learn our lessons. You know, this is very

much about watching the game tape back. And so whether that's at the enterprise level and we're doing it through in-depth interviews or work whether it's at the know the SMB level.

Cian Mcloughlin (08:47.026)
Back to your question, the next piece is you don't just go to one individual. Ideally, you get a cross-section of feedback from multiple stakeholders. It may be someone in the C-suite who was holding the budget. It may be someone in the business who was responsible for deciding which tool best met their needs. It might be someone in IT. So you need to know from a stakeholder perspective who were the folks that had influence. And ideally, you want to get feedback from multiple. So then you can intertwine those different sources and you get

a more single version of the truth by bringing those different pieces together because also you need to understand how different stakeholders are making these buying decisions if you're going to use this Intel in the future. yeah definitely multiple stakeholders and whether that's you know kind of survey driven at the quantum qual level or more interview driven at the top end of town is really contingent on you know the size of your deals and a bunch of other stuff.

Digital Rebels Consulting (09:42.28)
Do you get any feedback from your clients, customers that this is a differentiator, I guess from competition as far as just showing that upfront professionalism that we're trying to get better. Maybe not this deal, but maybe the next deal so we can make sure that we're improving our process, maybe our pricing, maybe our awareness of what your problems are so we can provide better solutions. Do you find that to be a differentiator?

Cian Mcloughlin (10:05.26)
Yeah, we do. maybe just for your audience, I'll kind of give some context. for many years, we focused on the top end of town. kind of interview driven, in depth interviews. A couple of years ago, we added a SaaS offering for the bid market. And we've kind of actually defaulted back pretty much to enterprise because that's where we feel.

we probably have the most value. But one of the things we hear again and again and again from customers is they're saying, wow, this is actually really impressive that this particular organization has taken the initiative to do this, has brought in an independent third party. They've clearly put effort and...

investment into this and we're actually really impressed because it's very rare that vendors do this. The other thing which is really interesting is different industries have kind of different cadence or a number of at bats with a particular client. So if you're an ERP vendor and you lose a deal, you may not get another chance with that particular client. So yes, you can learn a bunch of lessons, but you'll probably have to apply those into the next pursuit. But if you're a professional services company, you know, there may be three or four or five phases in a given project.

and then another team in your organization engages with that same customer here and another team engages with them over here. So you've got many, many more at-bats and you can learn and take those insights not just into future proceeds, back into that same client. Here's the crazy thing that I've learned. It's that customers will teach you how to sell to them if you ask really intelligent, thoughtful, curious, probing questions and then you really listen to what they tell you and you take action on the basis of what they've shared with you.

And for some organizations, you get the win immediately, literally in the next pursuit, because now they've turned over the piece of the puzzle and you're playing a different game to all of your competitors, because you now know exactly what they need.

Digital Rebels Consulting (11:54.608)
Fantastic. In your book, you have a five step framework that promises clean intelligence. Tell me a little about what that five step framework is and how you apply it to your work today.

Cian Mcloughlin (12:07.734)
Thank

That's a great question. I wrote that book a couple of years ago now, Marc. So I'm probably trying to struggle to remember exactly what those five steps are. for me, know, clean intelligence really comes down to a couple of things. It's about firstly setting the right expectation with the customer that you're going to be asking for it. It's about sharing with them exactly what you're going to use the insights for, which is a really important aspect. It's about ensuring that the people asking for the feedback aren't the people that the feedback is about.

But then it kind of comes back internally and then it's about what are we going to do with this because it's one thing to find out all this rich information from your customers. We've had situations where people are sitting with feedback going...

That's kind of structural. kind of, you know, that's a huge thing for us to try and work out and change. And the difficulty is when you've shone a light on it, your customer now knows that you know, your internal team knows that you know. It's very hard to sweep these things back under the road. So before you embark on this kind of an exercise, there's a level of kind of intestinal fortitude that's required on behalf of a senior management team to say, we're willing to take our medicine. We're willing to hear some things that might be challenging, that might be uncomfortable, but ultimately,

It's in our best interest to learn this and test and improve what we do. And so that kind of step by step process. And then the last piece of the puzzle, and not all companies do this, but the ones that do are really impressive in my mind. They're the ones that close the loop back to the customers and say, hey, these are a couple of really key pieces of information you shared with us. This is what we've done. This is the action we've taken. had one company in the US that we've worked with for many years. And what they used to do is they would traffic light the feedback.

Cian Mcloughlin (13:50.46)
red is negative, orange is neutral, green is good. And then they put work teams on that feedback to say, what do we need to go away and fix? What action are we going to take? And then they would always close the loop with the customers and go back and say, hey, you know that issue you raised around the poor quality of our reporting? Well, this is how we've solved it. And we just wanted to let you know that your feedback directly kind of impacted. And customers love that because if you fill out an MPS or a customer sat survey, invariably that disappears into the ether. You never hear about it.

never see it again. That's really frustrating because you've taken the time to give your thoughts and feedback. So the last step of that process is close the loop and give them the opportunity to understand that you've actually taken some action off the back of their feedback.

Digital Rebels Consulting (14:35.739)
Yeah, I got the five step framework here. I'm curious, I guess, if you have any one of these steps that stand out more than the others, as far as just effective, you know, salesmanship, if you will. And I think for companies, this is something I think that you could probably just post all over the walls as far as just, I'll read them off here. So number one is context, beats content, value over product, commercial teaching, co-creation, not persuasion, sales as a professional discipline.

those five things there, I think are critically important, for a variety of different reasons, but, co-creation at least for me, is my favorite. And that's something that I've always used for, for decades in sales. because I think that's the way that you, build partnerships, and you, it leads to more sales. And so, you know, listening to your customer and making sure, you know, going back to, your work as far as, helping them understand that, you're there not to sell to them, but you're there to, help solve their problems.

Cian Mcloughlin (15:23.266)
Thank you.

Cian Mcloughlin (15:34.374)
You know, the last one that you mentioned there, that professionalism piece, that's been a really intrinsic part of my world for the last 15 years because like so many people, I fell into sales and like so many people, it took me a long time to come to terms with the fact that I was in sales. You know, I had account manager and partner manager and all those other things and never had the word sales on any of my business cards, but I was carrying a quota or was managing a team with a quota.

And I had the realization that that was because there's so many negative stereotypes about sales.

And then I also had the realization that a lot of us call ourselves sales professionals. But I think the sales that we get for free and the professional that we have to earn over many years through our habits and behaviors each day. And it's that professionalism piece which for me is the critical differentiator in so many of the sales cycles that we've reviewed. And it almost doesn't make sense because we're in the B2B industry or at least that's where I play. And yet so often when we talk to customers they name

drop the individuals they interacted with on the vendor side. They were like, you know, that person was really patient. They were really knowledgeable. They asked great questions. They were really, you know, timely in their follow up and whatever. So they're name dropping the individuals and they're also talking about the attributes of how they showed up. And I think the realization for me is that, you know, we all think we work for a company or the brand in our business card, but in the eyes of our customers, we're the personification of that brand for better or worse.

And so they're actually making a buying decision about all of us as much or if not more so than the product or service that we're selling. And that might run contrary to what a lot of people believe, but...

Cian Mcloughlin (17:20.078)
It's really hard to buy something off somebody who's done a kind of a poor job, they've been unprofessional, they haven't been responsive because we just connect the poor experience we had with our expectations about what the product or service is going to do. so that professionalism piece for me is critically important for anyone who's building their career in sales. You're not 50 % better or 50 % worse than your competitors. There's all these little fractional one and two percents right the way through the customer buying journey. They're the little pieces.

we need to be picking up and when last gives us a bunch of those.

Digital Rebels Consulting (17:54.813)
yeah, I agree with everything that you just said there. And I think that, at least the sales profession, there should be, I don't know, more support around, think, in general, as far as just a continuous improvement. Companies don't seem to provide any of that. And if they do, it's on some sort of digital platform that probably nobody visits, which I think is, I don't know that there's a lot of.

things to unpack there, but I'll leave that one alone for now. As far as CRM and we were talking about that dropdown box and things like that, what are some of the three typical frictions that you think or have found over your research that really kill enterprise deals but don't show up in CRM?

Cian Mcloughlin (18:33.806)
That's a great question. could just spend the next hour talking about that one, Marc. I think...

One of the things that we see, and this is very much at the enterprise level, is we see an awful lot of decisions get made in what you might call the aural phase or the presentation phase in decision making. And yet, in many cases, that doesn't show up in any material way because quite often a customer might have a scoring criteria for how they're going to compare different vendors. And presentation aural may not even be in that. And yet, when we talk to customers time and time time again, they talk about how they should

showed up, how well prepared they were, how they interacted with each other, the questions they asked, the confidence they gave us, the knowledge and the credibility they had and all these other things. So for me, whenever I work with organizations, I talk to them about the importance of that particular phase and I talk to them about doing your dry runs, making sure that you're making your mistakes in the room. And the best little tip for me that I ever had in my own sales career is that invariably there's somebody internally on the other side, on the customer side, who's very invested in this outcome as well.

them along to your dry run. If you've got a relationship with your sponsor or your key stakeholder, let them know we're going to do a dry run on Tuesday ahead of Friday's presentation. You're welcome to come in, you're welcome to sit in on it, you're welcome to poke some holes in it. If they've got a very formal structured process, they may not feel comfortable, but many, many times I've had customers who've said, that'd be great, you know, I'd appreciate it. Because it's their professional

brand that's on the line internally in their own organizations as well. So you're giving them another opportunity to ensure that this is a good experience. that's the first one I think I would talk about. It's that kind of the human piece. Risk is the next one, Marc, that I'd talk about. sometimes risk can show up in CRM, but more often than not, doesn't, not in any material way. And yet risk is the single biggest decision criteria that we've heard from customers over the last 18 months to two years, again and again and again.

Cian Mcloughlin (20:37.904)
shows up in a bunch of different ways. And I know when I was early in my sales career, I ran for the hills to try and avoid conversations around risk. Because in my mind, risk was, this is going to slow the sales cycle down. This is going to lead to revenue recognition issues. This is going lead to this and that and the other. And so I tried to avoid that. You can't avoid risk at this point in time. You've actually got to lean into it. Because what we're seeing is that vendors who do a better job of understanding, managing, mitigating, sharing risk.

they win an unfair share of business at the moment. And so, you know, that would be something I would be strongly suggesting that anyone listening to today's show really leans into. But the fact is that risk is organisational, but it's also personal. And so you really have to tease those things out. And then the last one is price always shows up in CRM, but value rarely shows up.

And the big differentiator for me is if you say to people, tell me what's important to you as a decision criteria. Price will often be quite high. But if you then say to them, is it price or is it value for money? Price will drop and value for money will go up.

But the challenge with value for money is like value is in the eye of the beholder, like beauty is in the eye of beholder. So a huge part of the role of sellers is to through their discovery, work out what does this customer actually value and then give it to them. That's like negotiation one on one, give people what they want on your terms. But that doesn't show up in CRM either. So there isn't a mechanism to sort of say, you know, what were the really critical value drivers for this particular customer versus what was the price point we came in at? And so

I think CRM is great. It's a great tool for forecasting on the one hand as a customer repository for memory on the other hand you can do a bunch of stuff with it that you used to be able to do. you know absolutely huge fan of great CRM usage but it's not a substitute for the kind of the softer elements that kind of show up in a sales cycle and you've got to get a balance of both of those if you're going to win.

Digital Rebels Consulting (22:43.22)
I haven't done any research on this, but kind of what you were saying as far as practicing before you, you know, you get into that meeting, have some people take a look at your presentation and your pitch and what you're going to say. but I'm curious, do you have any insights on to how many deals are lost in the first meeting?

Cian Mcloughlin (23:01.102)
Yeah, that's a great question. I probably don't have too many insights on that, Marc, and I'll tell you why. Because if a deal is lost on first meeting, we would rarely be asked to go in to do a of a post sales review. for us to do a review, there needs to have been multiple steps in the process. It needs to be a level of complexity and moving backwards and forwards. But I can say...

We've heard some horror stories from customers around some of the poor interactions they've had with salespeople through sales cycles. mean, I'm talking, you know, the usual stuff that you would imagine where it's like they pushed us too hard and they tried to get us to close in their timeframe or whatever, but that's kind of like, that's just small bickies. We've had situations, we had one customer who shared with my consultant when they were doing the debrief, he said, look,

We received a document from this particular vendor as part of their tender response. And somebody had turned on track changes in the right-hand column. And someone had written, I just made up these case studies. And someone else said, that's OK. Just put them in anyway. And then they PDFed it with the track changes. And this individual shared his screen and showed that. And he was like, that was the first impression. And we've had so many of these examples where you're just going,

your head explode. So, you know, I get to work with a lot of sales teams all over the world and one of the things I say to them is like, just don't be like terrible. Don't be unprofessional. Don't be sketchy. Just take your time. And the reason a lot of these things happen, not necessarily that one, but the reason a lot of this stuff happens is because we're,

forcing reps to do three times cover, four times cover, five times cover. So they're just spinning plates all over the place. And now we're trying to leverage AI and we're trying to leverage other tools to help us with our capacity to do things. What happens is stuff starts slipping through the cracks because we're not carving it enough time to do exactly what you just said, to do the dry run, to have someone sanity check it and read it back to us. I spoke to another customer not that long ago and they were making a $50 million buying decision. They had like,

Cian Mcloughlin (25:12.622)
12 or 13 vendors that had all responded to a tender. We were there representing one vendor and the customer said, look, their tender response was so poor that we had a through to the first round, like they had a table in their office and there was one pile which was through to the first round. We're going to take another look. There was one pile that was out and there was a maybe pile.

And they were sitting on the maybe pile because what they'd done is they'd taken the tender, they'd broken it into pieces, they'd sent it off to lots of different people and said, you respond to that, you respond to that. And then they kind of brought it back together and cobbled it into a Frankenstein's Bride kind of response document with intelligent, well articulated response here, gibberish here, different fonts, different. And then they'd given that to the customer as their response document because they just didn't have a good process. That was a $50 million piece of business.

We've just got to level up our expectation. I see a lot of like late 80s, early 90s quality documents coming out from companies. We just can't do that now. We just need to be better.

Digital Rebels Consulting (26:11.801)
for large enterprise deals and ones that I've dealt with in the past, I think that, typically I've said that, you know, you went a hundred million dollar deal and the day after that, you should probably market as risk because, also depending on why you won that deal. But I think that most people, they went a big deal. Everyone's excited. They, you know, they celebrate and they move on to the next deal. But I think you have to just my own opinion. This is how I approach it is as I think you have to hold on.

to everything or the reasons why you won that deal and not just let go of it as far as just, the reasons why you want it and making sure that you're nurturing the champions within the other company and making sure that everyone is still kind of satisfied and meeting those expectations along the way. typically when I've looked in and CRM before we have loads of money and the opportunities, everyone's talking about opportunities and nothing is ever in the risk.

But I think that once you want a business, um, that business is essentially at risk. Cause at some point in time, the people that, uh, you know, gave that business to you might not be there in a year or two and making sure that you're, uh, guess, acutely aware of, um, what those decision, I guess, uh, making processes, how they might shift over time and not losing a hold of that. Because I think that's how competition can come in and steal that from you. Um, what are your thoughts on that?

Cian Mcloughlin (27:36.456)
like you've set up, you've set a bucket load there. So the first thing is you need to understand why you want it. so, so, you know, you, you win a hundred million dollar deal. I guarantee you there was five things that could have killed that deal for you at certain stages that you probably didn't even have visibility into. So you need to unpack that A so that you can take those learners into other pursuits and win more hundred million dollar deals. But B you can understand where the risk factors were in that sales cycle. But, you're absolutely right. My view is a customer is only a customer when they buy from

you for the second time. The first time they buy, they're giving you an opportunity and contingent on how well you deliver on the promises you made, then all of a sudden the golden gates swing open and you see all the other opportunities. so the handoff from sales to delivery needs to be absolutely perfect. Delivery should be involved before the end of the sales cycle.

whatever you do from an account management or customer success perspective needs to be really crisp and well executed. And you're right, there's a ton of risk in that sales cycle because what we see is we see huge deals lost by incumbents because they just got fat and happy, they got lazy, they took it for granted, they were gonna retain that customer because the cost and the effort to move were so significant. And yes, that is a barrier to entry for other participants, but it will get to a point where the customer is so frustrated with the lack of value

or the diminishing service that they're getting from you, that they will go to market. And then all it takes is one other player to come in and do an incredible job and there's risk there. So given how hard it is to win a net new customer, why not get out ahead of this and build in, just to your point, mechanisms to test for risk. What's the canary in the coal mine at six months, at 12 months, at 18 months? And can we stay ahead of these things? And if you do that, then nobody's got a customer for life, but you may have them for five, 10, 15

years which is pretty good.

Digital Rebels Consulting (29:27.74)
Certainly. Let's shift a little bit into a discussion around AI. I'm curious how you're using that, at least in your business and how that's showing up in some of the conversations that you're having with clients.

Cian Mcloughlin (29:40.462)
So in terms of how we're using it, I came to a realisation quite early that the best mix for us was a combination of human and the loop in AI and that's proven to be the case because at the top end of town when we're working with really, really senior stakeholders and multi-million dollar pieces of work,

You can't have an AI tool step in and have those conversations on your behalf. Maybe in five years you will, but at this point in time you can't. What you can do is do a ton of research ahead of time and use that to ensure that those conversations are as nuanced and as impactful as possible. Obviously, we use it for variety of things like core recording and core transcripts and synopsizing, things like that. so we've used it to do some of the grunt work and the heavy lifting behind the scenes.

but for us it's that kind of human in the loop, that human touch from our really senior...

consultants that gives us a nice balance between the two. I use it all the time as well, know, in my work and the research I do. You know, I write content on LinkedIn. Sometimes I use it to help me kind of come up with ideas for that. But I don't, I haven't used it to write content for me. I haven't used it to write emails for me. Haven't used it to write proposals, know, soup to nuts from start to finish because...

As soon as we start doing that, for me, we're losing that human essence. And people might disagree with me and say, well, Keon, it can sound like your voice. Maybe it can, but it's not going to parse the information the same way. And so I'm trying to find a balance for our organization where we kind of get the best of both worlds. And I think we're doing OK.

Digital Rebels Consulting (31:21.946)
would you feel confident as far as we were just talking about, presentations and pitching and having someone poke holes in it and, objections and things like that. Would you trust AI to, find those things for you?

Cian Mcloughlin (31:31.395)
Yeah.

Cian Mcloughlin (31:36.11)
It's a great question. It's an interesting use case. I don't think I would trust it at this point in time. I think, you know, there's great emerging tools that allow you to kind of speak to camera and have it come back to you and tell you and give you feedback and pointers on that. But quite often there's going to be multiple stakeholders on your side of the table and on the customer side of the table. And so that dynamic, I think, shifts a little bit. So if there's no other mechanism available to you, you don't have an internal boss or coach or manager.

or whatever, then yeah, absolutely, that's a better mechanism and there are some really good tools.

In my old SAP days, I remember what we used to do is we would have to present to a group of folks who weren't involved in the pursuit and they'd get to hold up a card that said, what, every time we gave information in isolation without giving context, which was really annoying and they took great pleasure in doing it. But what it forced us to do was it gave us this muscle memory that instead of just kind of showing up and throwing up, we would give information and give the context as to why that was relevant for the customer. And so that built this kind

of mechanism, where 100,000 people, well, why do they care about that? What that means for you is this, or, and it forced us to say it like we were saying it for the first time, rather than just kind of regurgitate it as we can often do, where you're kind of just drinking from the fire hose and you're regurgitating it back when you've drunk the Kool-Aid. And that was a really useful mechanism for me. And so I'm sure tools like AI will be great at helping out in those situations, but I definitely feel like you still need that human piece.

to just to help you ensure you're on your A game.

Digital Rebels Consulting (33:17.305)
Yeah, certainly. It does miss, I don't know, the little nuances and I'd probably have difficulty as far as articulating what it misses, but I think that typically when you get a response back, just from a human perspective, it misses, I don't know, maybe it's like the emotion that that's lacking there as far as just the buyer emotion. And I guess having empathy for what the buyer is going through, what other people that are in the organization are going through. It does miss that and also history.

Cian Mcloughlin (33:32.93)
Yeah, the subtle cues and yes, those are the things.

Digital Rebels Consulting (33:44.969)
as far as with, with the account potentially and how that, guess, ties into kind of what the current state of affairs in are with, your business today. it actually gives me the thinking. So when I was typically taking over like a new account or a bunch of different accounts, I would typically go into Salesforce and I would just manually read call reports, from the last year from the account rep from years ago, just so I can get a sense.

of kind of like what's going on in this account and how can I provide value because we might show up to a hostile environment if you will. And you kind of need to know that. And if that's not given to you by the prior account manager or maybe your boss, I think that's something that you kind of need to know. And guess the question is, is that something that you help, I guess, some of your clients with as far as extracting out that information as far as the customer history in order to reshape?

and make a better pitch and a presentation.

Cian Mcloughlin (34:42.634)
No, in short, we don't do that. Although I agree with you, that's incredibly important. What we do is kind of at the other end of the spectrum, Marc. So we will usually do a debrief with the account team before we go and speak to the customer so that we get the context, we understand, are they, know, what's the context? Because I'm less interested in the reps.

views or not in a disparaging way, but what fascinates me is what happens behind the curtain, what's influencing the buying decision, why are customers doing what they're doing. And so that's the bit that we really kind of double down on. So we get context from the sales team and the sales management team as to what their experience was with that customer, were they hostile, were they engaged, et cetera. But ultimately, I'm more interested in hearing directly from the decision makers.

Digital Rebels Consulting (35:29.338)
Gotcha, understood. Let's pivot over to our rapid fire segment called burn it or build it. I will give you 10 hot takes and B2B. You answer burn it or build it and maybe a brief reason why. Are you ready? All right, let's go. Number one, cold email sequences.

Cian Mcloughlin (35:48.174)
I've used them myself in the past. I think they're becoming less and less and less valuable. I will say build it, but build it really, really well or else it'll be pointless and it won't get you anything. So build it just.

Digital Rebels Consulting (36:07.619)
Gotcha, build it carefully. Number two, typical quarterly and discount rituals.

Cian Mcloughlin (36:17.358)
Burn it.

We're teaching our customers the wrong thing. We're teaching them to come looking for a discount. We're teaching them to dig their heels in until the end of the quarter. We're teaching them terrible habits. the thing I learned, right, first thing I learned is, you know, a discount takes money out of your own back pocket. And bizarrely, it took me quite a while to learn that. The penny didn't drop. But the other thing is we're setting an expectation with our customers. Like we're digging into future deals because now I've discounted. So their expectation is that's the minimum. For me, everybody wants a good deal and everyone deserves a good deal. But a good deal is rarely the cheapest price.

unless there's nothing else we can give them. And if there isn't, we probably haven't done our discovery well enough.

Digital Rebels Consulting (36:55.887)
Yeah, certainly. I agree. It just creates a habit, if you will. And if I'm a buyer, I can just look at the calendar and say, I'll just wait a couple of weeks and maybe I'll get a couple of points off. Number three, gated content for leads.

Cian Mcloughlin (37:04.364)
Yeah. Yeah.

Cian Mcloughlin (37:11.436)
I'm not a big fan of gated content for leads. The philosophy I've had for the whole time I've been running my business is like...

is give people value early in the sales cycle because they will reciprocate in kind. And so, you know, if it's incredible content, maybe you get it. But I think most of what sits behind those firewalls is actually not incredible content at all. I would much rather give it to my sellers and allow them to drip feed that content because what that does apart from anything else is it creates reciprocity. People want to reciprocate because they've been getting value from you all the way through. So my view is actually

look at the customer buying journey, line up all of your content assets against where they're at in their buying journey, give it to them, and you'll start to separate yourself from the pack, but also you'll create that kind of warm reciprocity, and that can be great leverage at some point in the sales cycle. I think you've got to bring your IP to the surface, you've got to turn it into assets, you've got to share it with the world, and then you've got to back yourself that...

the ripples will go out and they'll come back to you.

Digital Rebels Consulting (38:20.697)
Gotcha. Number four, sales frameworks. like Bant, Spice, Medic, Med Pick, just all these different frameworks, burn those or build them.

Cian Mcloughlin (38:35.822)
Like if you're young and coming into sales for the first time, there's definitely value in those kind of frameworks because it gives you a structure. The challenge I have with it is they've become, people have defaulted them to such an extent. They're like, no, we're a med pic organization. We're this, we're that. Whereas sales cycles don't happen in between those kind of different channels. So I'm probably gonna say, burn it. that'll probably come back to bite me, but yeah, screw it, burn it.

Digital Rebels Consulting (38:59.598)
No, I agree. I think it's a burn it as well. think ideally, um, typically everything in the CRM and the frameworks, everything's just linear and you do step one, step two, step three. And in these complex deals and large deals, these hundred million dollar deals, it's not a step, step, step, step. Um, but you should, you should at least, uh, I guess understand maybe some of the information I need.

Cian Mcloughlin (39:08.462)
Yeah.

Cian Mcloughlin (39:15.788)
It is easy.

Understand it. Yeah. Yeah. It's like it's like great artists who understand all the things and then they ignore it and do their own thing. So yeah, maybe maybe learn at the start. Learn it then burn it might be the way to go.

Digital Rebels Consulting (39:30.626)
Gotcha, hence the name, burn the playbook. Number five, win loss via seller self-reports. I think we talked a little bit about this as far as just a self-report.

Cian Mcloughlin (39:41.238)
Yeah, I'm massively biased here, Marc, but I would say there's almost no value in the seller self-reporting. You can get somebody internally in the organization. it's not vendors can't self-report. It's the rep who is involved in the pursuit. I see very limited value in that. And that's no, I'm not throwing shade on reps. You know, I carried a number and I completely understand it. It's just, you're just not in the right position to be giving that feedback because nobody will share it with you, honestly.

Digital Rebels Consulting (40:11.393)
Gotcha. Number six, RFP sales motions.

Cian Mcloughlin (40:17.922)
I've kind of flip-flopped on this one. I was of the opinion many years ago that if you haven't helped to write the RFP, then you're not going to stand a good chance of winning it. I call BS on that now. I think if you can respond in a really articulate, clever, timely way, you can absolutely win very significant pieces of work. The critical thing for me is how you do your upfront discovery. And I see a lot of businesses who've rushed that and do a poor job of that. It comes back to what I said earlier. Customers will teach us how to sell to them if we show up in the right way.

So it's a huge amount of effort, it's huge amount of cost. The very least you should do is say, you know, in exchange for my cost of sale, I want to do a proper debrief and get some value back off the table. But I think at the top end of town, you have to do them. You just need to do them better.

Digital Rebels Consulting (41:03.757)
Okay. Number seven, MPS as an account health metric.

Cian Mcloughlin (41:10.616)
Burn it. Yeah, I think NPS has been... But when it came out first, probably great, but it's become less and less valuable and valid in my opinion. And people just game it. They send it to someone and say, I need a nine or a 10 here. We recently bought a new car. The car salesman told us, I need a nine or a 10 or I'm not gonna get my bonus or whatever. It's pointless. burn it.

Digital Rebels Consulting (41:34.006)
Do you ask for a discount, I guess, if you're gonna give him a

Cian Mcloughlin (41:36.204)
We only did that after we pulled the car, so was smart enough, yeah.

Digital Rebels Consulting (41:40.076)
Number so it's a burn it for NPS number eight demo heavy sales cycles

Cian Mcloughlin (41:45.218)
Yeah, right.

Cian Mcloughlin (41:52.354)
I'm not a big fan of demo for the sake of demo. I think sometimes we hide behind our demos and our laptops. So I'm going to say, I'm going to say burn it. But with the caveat that you've got to be led by your customers. it's really dependent on what they need at what point. And if they bring in more more stakeholders, you'll have to do more demos. as a default standard, I don't think demo heavy is the way to go. So I would say burn it.

Digital Rebels Consulting (42:17.942)
Burnit. Number nine, AI generated sales call summaries.

Cian Mcloughlin (42:22.542)
Yeah, I'm big fan. I think they're really helpful.

I think the worst step of the sales process is the follow-up. That's where I see many, many sellers fall down. They do a decent enough job in the outreach, they do an okay job in the meetings, and then they do a really poor job in that. So I think there's a ton of value in terms of getting that feedback, distilling it down, turning that into the follow-up email that you're going to send, then kind of, you know, nuancing and curating it as a human and maintaining that kind of rhythm with the customer. So used intelligently, I think there's lots of value in that.

Yeah, build it.

Digital Rebels Consulting (42:59.393)
Build it. Number 10, last one, quarterly business reviews.

Cian Mcloughlin (43:03.918)
QBRs, don't we love to hate them? More often than not, I find people start off with the right intentions and then we just phone it in and phone it in. So I think done right, could be very valuable. Done wrong, they're just a waste of everyone's time. And so I'll have to sit on the fence on this one because some organizations I think it's a great thing and others it's just pointless.

Digital Rebels Consulting (43:28.704)
Gotcha. You get the final word today, something that sales leaders can implement tomorrow. So if you're a sales leader, what's the one thing that they can do tomorrow? Let's just say there's no budget, no software, no approvals that they can improve their win rate.

Cian Mcloughlin (43:42.414)
Look, I'm going to say set an expectation with your customer that you'd like to get some feedback at the end of the sales cycle or tell your reps to do that because I think it's crazy that we call ourselves professionals and we don't watch the game tape back as an industry. I think it's the biggest dirty secret in the sales industry. There's so much wastage. We spend vast amounts of time and money and cost of sale on these pursuits and that's kind of the only way.

It doesn't mean we can't get some value back in return. And customers are very, we've been doing it for 15 years and sellers are constantly saying, but customers won't tell, yeah, they will. Yeah, they won't tell the truth. Yeah, they will. They won't, know, yeah, they will. So, so take advantage of it. You don't need to spend a dime. Just get someone else in the organization, put a little bit of structure around it. I have a framework that tells you exactly how to build it internally in your own organization at no cost. Reach out to me. I'll give it to you.

Don't leave this stuff behind. You've done a good job. You've earned the right to it. Capture it. So that'd be my feedback on that one more.

Digital Rebels Consulting (44:45.759)
Fantastic final word. Where can people learn more about Trinity and your work?

Cian Mcloughlin (44:52.11)
So you can head to our website which is usedtrinity.com or you can hit me up on LinkedIn. I tend to write and share content there as well. And yeah, please do. I'm always interested to meet with sales leaders and sales people and I've got a bunch of assets I'm very happy to kind of share and put them out into the world. reach out to me.

Digital Rebels Consulting (45:12.35)
Fantastic. Thank you for the time.

Cian Mcloughlin (45:15.16)
Pleasure, great to be here.


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Marc Crosby - Digital Rebels

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