E17: How to Win More Deals by Turning Losses into Lessons with Cian McLoughlin | CEO Trinity Perspectives

Welcome to the Switch Keys Podcast. This is Priy Saka, and today I'm joined by Kian McLoughlin. Kian, thank you so much.

Hey, Priy, it's great to be here.

Fantastic. Allow me to introduce Kian because he is pretty amazing. So Kian is the author of the Amazon number one bestseller, Rebirth of the Salesman, and he's a regular sales and marketing commentator. In mainstream media and globally recognized keynote speaker. His blog was voted one of the top 50 sales blogs in the world. And for the past 4 years, he was recently chosen as the LinkedIn top sales voice, which congratulations, is incredible. Cian is the founder and CEO of 2 businesses, Trinity Perspectives and Trinity Digital, and guest lectures at the Macquarie University in their business incubator. Prior to founding Trinity, Kian had more than 15 years of B2B experience, including senior roles at companies like Cognos and SAP. So again, Kian, I am so glad that you are chatting with us today. Thank you.

I'm happy to be here.

Fantastic. So Kian, in addition to knowing you, I admire you for the tremendous Quality content and engagement that you've created online, and you just keep giving terrific value. So what was your journey that between being a number one bestseller and then LinkedIn top voice? Both are extremely they're hard to get done. So tell us anything about that. How did you get there?

Look, I think it's definitely been a journey, Pri. I was a sales guy and I was a channel guy, and then I became a bit of a cubicle escapee just over ten years ago because I was. I don't know. I was ready for something different. So I definitely didn't see myself as an expert really in anything. I knew a little bit about a lot, but I didn't necessarily have domain expertise. I think the first most important thing for me was picking a niche, picking an area that I felt passionate about, but also what I saw as a real problem to solve. And that problem was this idea of conducting win and loss reviews at the end of a sales cycle. This was something that occurred to me while I was still employed in the corporate world. I had this kind of epiphany, I suppose you'd call it, that we were putting all of this time and effort and energy and resources and blood, sweat, and tears into these pursuits, which might take 3 months or 6 months or longer, and doing a pretty decent job. And then at the end, we'd either win or lose, and we would never really understand what had influenced the customer to make their decision. So we'd sit around in a room and we'd just make stuff up, and we'd create a kind of an acceptable narrative for what we felt probably influenced their decision. And then we'd move on to the next opportunity. And that just struck me as crazy. Going back to your question, once I started focusing on this area and running a business doing this, something really interesting happened. 2 interesting things happened. The first was I'd picked a niche and so I was referable. Now people understood, oh, you're the win-loss guy. So I started through word of mouth and my network getting good prospects and good customers that way. But also I was getting this really fascinating insight into what actually influences customers. to make their buying decisions, because I was talking to them every day and my consultants were talking to them. So we were peeking behind the curtain and seeing what was really influencing the buying process. And a lot of it didn't align with what I was hearing in the market from, in inverted commas, sales experts who were talking about, oh, you have to do this and you have to do this. So I just started sharing. I just started talking about, this is what we're hearing. This is what people are telling us. Just tried to do it in a very simple, authentic way, as if, just like the conversation you and I are having here today. And for whatever reason, I think being quite authentic and not being salesy, but also sharing stuff which is seen to be actually interesting and valuable and searching for the bit that's engaging for people, it just created a readership. And so that from a LinkedIn perspective was probably where the journey began. And then from the book perspective, it was just taking a bunch of that and saying, what are the things that are most interesting? And then sitting down and Finding the time to write a book. Yeah, that's been the journey.

And I've just got to say, my favorite post among all your posts, which I like so much, is the one about the note that you wrote for your son. That just absolutely struck a very deep chord as a parent, right? I think that's amazing. And for those who are listening, can you just give us the short version on what that note was about?

So I've got a little boy who's just turned 11 recently. And I came across an article somewhere about how do we create a safe environment for our kids if they have things which are awkward or scary or uncomfortable to talk about. And it struck a chord with me. And so I grabbed a piece of paper and a pen and I wrote a little note for my son. This is going back a couple of years now to let him know that if he ever had something he wanted to talk about that was scary for him or uncomfortable for him or confusing for him, He could bring me this note and at any time, and he wouldn't get in trouble and I wouldn't get mad and we could talk about the thing that was on his mind. And when I initially gave it to him, I think he was about 8 when I gave it to him and he looked at it, he was like, oh yeah, okay, Dad. And he stuck it in his top drawer and didn't think anything of it. And then all of a sudden one day he brought it to me and there was something he wanted to talk about. And over the last couple of years, he's brought me that note multiple times and sometimes for quite small things, sometimes for things that from his perspective are really big and life-threatening or scary. And so because it was such a simple but such a powerful tool in our household, I just thought, you know, it might be something that other people could get some benefit from. So I wrote a little post about that and just got so much interest and traction from people. And a bunch of people have come back to me and said, I did this and this is the conversation I had and this is how it changed our relationship. So it's been really rewarding just to see people getting some benefit from an idea that worked for our household.

And just sharing back with you, that impacted me so much. I actually got— I've got 3 kids, 19, 16, and 12. I've had 3 conversations, which were the same conversations so that hopefully they hear it once, having told them thrice. But I've actually had face-to-face conversations saying that no matter what the situation, and I've enlisted some situations specific to their age group that you come across. Yeah, you can come and talk to me about it. You can— mom and dad are not— and it's been both my wife and I who— so thank you. Before we move on, thank you so much.

You're very welcome.

All right, look, let's jump into win-loss analysis. I know of so many companies that have worked with you Uh, speak of you highly. I have talked about situations where from educating and training their teams to flying out to see clients to your software. This is a very interesting area because a lot of companies do not learn. They keep moving forward and they don't look back. And tell me, in terms of what are some of the key mistakes that you see companies making, especially when they have lost a deal? What are some of the key challenges that you see where companies are not learning from that?

Look, I think the most basic challenge, Pri, is that an awful lot of businesses even still, and I've been preaching this for more than a decade now, the vast majority of B2B businesses still don't do any consistent form of win-loss analysis. Occasionally what happens is someone picks up the phone and calls a customer. Usually that's maybe the GM of sales or someone. Usually they do that when a deal has been lost and when it particularly hurts. And so they decide they want to get a little bit of feedback. But what they don't do is they don't set an expectation with the customer that whatever the outcome, they would love to debrief with them. So that's the first mistake that they make. The second mistake they make is tending only to focus on the losses and not actually focusing on why did we win? What did we do well? And how can we make that a repeatable lesson across the business? The third thing is because it's done in a pretty ad hoc manner, there's no real structure to it. So it'll be a different person asking a different set of questions each time they do it. And then they don't have any mechanism really to do anything with that feedback. So it just disappears into the ether. And the critical bit of feedback that I give to businesses all the time is irrespective if you use an independent third party or you do this in-house, it needs to be consistent. You need to set an expectation with the customer that you're going to be doing it. You need to have a clear set of questions that you want to ask. Ideally, those questions should align to the customer's buying journey, not your sales cycle, because it's much more interesting to ask them about the journey they've gone on. And then you need a mechanism to actually do something with that feedback. So this was a big learning for us when we started doing win-loss reviews more than a decade ago. I thought our job was we'll go and interview the customer, 2 or 3 people. We'll capture what they told us and we'll give it back to you. And initially, that was okay. And then a couple of the sales leaders we were working with said, hey, Cian, could you interpret this for us? And I was like, what do you mean? And they were like, could you tell us what we should do? You're finding this stuff out for us, but what should we actually do? And I was like, oh, I thought that was your job. And they're like, yeah, it is, but it would be helpful if you could do it for us, because then it avoids some of the kind of the internal conversations, and we can just get focused on actually taking some action. So then we started going, okay, here's what they told us. Here's our findings. Here's our recommendations. This is the prioritization. This is what we think you need to go away and fix internally in the business. And that's when it really started to get sticky because all of a sudden businesses were going, okay, now we know what's working, what's not working. We've got some guidance on what we need to fix. The noise kind of settles down and we can focus our attention on— could be a sales enablement issue. It could be a pricing issue. It could be a competitive issue. The ripples go in lots of different directions. But now we've got something concrete and actionable rather than making assumptions, which is what most sales leaders need to do in terms of how do we move the needle, what's working and what's not. So that's the thing that I think is almost the most compelling. It's all of the he said, she said goes away. And now we have a very clear conversation around, we know what the problem is. Do we want to fix it? Or we know why we're doing really well. Now let's spread that learning across the business.

That's amazing. Yeah, look, and I think about the age-old wisdom of history repeating itself. I wonder the true cost to an organization of bottlenecks and weaknesses that have not been identified, and you just continue with your go-to-market motions quarter in, quarter out. And you lose deals and you're not learning from it. Yeah.

Look, it's a really good point you make because there's the obvious impacts, which are, as you say, lost deals. There's a finite amount of opportunities out there. We've got to be winning more of them than we are. So that's the obvious one. But if you're identifying gaps and nothing's being done about it, then that impacts the morale of the team. It impacts your retention of salespeople and sales leaders. And we've seen many examples where People are going, you know what? We know what the problem is. Leadership know what the problem is, but nobody has the appetite to address it because it's too hard or too politically sensitive, or it's a structural change that's required in the business. And as a result, you start losing people. Well, you also start losing customers, not just new prospects, but existing customers, because they can see as an organization that you're not forward-looking, that you're not prepared to make change, that you're not willing to sacrifice the sacred cows that made you successful in the past and do things differently in the future. The impacts are obvious at the top-line perspective, but the bottom-line soft impacts ripple through the business a lot as well. And that's a real challenge.

That's really interesting what you just mentioned, because there's the ripple effect that you're talking about. I think most people only see the tip of the iceberg, which is we didn't lose the deal. But obviously beneath the iceberg, you have a loss of morale because losing a deal impacts everyone who's involved, as well as it exacerbates the pressure that's on the team to meet quota. And obviously there are things that need to be done. Yep, go ahead.

I was gonna say, let me give you a real-world example of this. We worked with a vendor who over the last quarter and a half probably has lost a bunch of deals. And interestingly, a lot of their lost reviews have read like win reviews. Team did a really good job. They were very proactive. They were very responsive, really engaged. And we're like, you read it and you think, this is really weird. But what had happened was they've effectively priced themselves out of the market because they haven't shifted as the market has been shifting around them. And they're somewhat of a commodity solution in terms of what they do. So it's been really interesting from the perspective of the sales team in that organization, as they get these reviews through. On the one hand, it's frustrating for them because they've lost the deals. But on the other hand, they can see that they're getting really good feedback in terms of their performance and their effort. So the management team now are aware of the fact that this isn't actually an issue of sales execution. And ultimately what this has done is this has driven a complete shift in their pricing model because the leadership team have gone up the food chain and said, we need to fix this. We're coming 10th out of 10 from a pricing perspective. Against our peers in the industry, but we're coming first and second against a bunch of other decision criteria. But if we can't solve this value for money and pricing issue, then all the hard work of our team is in vain. So they've completely shifted their pricing in the last 6 weeks. And now they're starting to pick up deals that are $5 million, $10 million that they were losing literally 6, 8 weeks ago, because they've pivoted their strategy and they've made a bunch of really quite considered changes to their go-to-market.

What? And it makes you wonder why it isn't a fundamental— most leaders are obsessing about the forecast, but not looking backwards at why did we lose what we do? Because just changing your win ratio by 10 percentage points or higher can have a tidal effect downstream.

100%. If you can look, there's 3 metrics that I think we influence in a material way. So Your win rate, the velocity of the deals. So how quickly sales cycles are closing, because the other thing that we're observing is we find out where a lot of the invisible friction is in the buying journey for customers. And once you find that invisible friction, you can then actually go away and do something to remove it. So why are deals slowing at this stage? And then you talk to the customer and they say, you asked us to do this and then that happened and then this happened. As a result, everything kind of ground to a halt. Oh, okay. Should we have done that? You can start to unpick that. So Deal velocity improving, win rate improving, but also looking at ways to reduce the need to discount. So we're not eroding margin from these opportunities because what we're seeing, and this will tie in with your worldview, I'm sure, really poor discovery leads to poor sales execution, which leads to the need to discount because we've got nothing else to play with from a negotiation perspective. Where we see really Good discovery combined with responsiveness, not only does the win rate go up, but the margin stays higher on those wins because everybody wants a good deal and everyone deserves a good deal, but a good deal isn't the lowest price unless you've got nothing else to give me, and then I'll demand a low price. So all of these things are interconnected, and that's where it starts to get really interesting. Stop focusing at the front end of the funnel. How do we get more stuff in and start thinking, actually, As pipeline diminishes, as sales cycles are elongating, what can we do to get better with what we have, do more with less in terms of the opportunity? So yeah, that's where my thinking is on that.

That's really impressive. I think that in terms of the key metrics that you mentioned, you early on, you touched upon some of the criteria and I really liked the 1 out of 10 scoring. You talked about you could have the team executing at a 1 out of 10, but pricing could be, the team executing at a 10 out of 10, but pricing could be at a 1 out of 10. So what are the key criteria? Will you lay out in win reviews, what are some of the most used criteria to assess the situation?

Sure. Yeah. Yeah. So let me just quickly jump back to something for one second and then I'll answer that question pre. The question set that we ask customers when we do a win or a loss review aligns perfectly to the buying journey that they went on with the vendor. So we ask them, What was the catalyst for you coming out to market? Where did you do your research? Who did the research? How well did this vendor show up in the early stages? And then we map it all the way through their buying journey. And as we're asking them questions, we ask them quantitative questions. So could you score this vendor against from 1 to 10? And we asked them a bunch of qualitative questions. What was your impression? What worked? What didn't work, et cetera. So we're getting a really nice balance of this kind of quantitative scoring feedback and qualitative Voice of customer feedback. But there's a couple of consistent trends that emerge in terms of where we see win rates going up. And the most obvious one that we see is if you score really high in responsiveness throughout the sales cycle or throughout the customer buying cycle, the likelihood of you winning is significantly higher. So that's one big tick in the box. If you do nothing else, if your listeners do nothing else but say, I'm going to up my responsiveness in terms of How I interact with my prospects. That will be a 1% tick in the box for them. But these little 1%s add up. Second piece is if you do really good discovery, so they perceive that you've taken the time to understand their business, their problem, their pain point, and then you continue to come back to that as a way to frame the conversations you're having. That's a really important point of differentiation because unfortunately an awful lot of sales reps aren't getting the discovery piece done very well at all. They're trying to skip past that. Straight to the demo, let me show you our stuff bit. So that's the second bit. There's also a really interesting correlation with having enough patience on the one hand, but also being able to guide the customer through the buying journey, which is a really interesting balancing act between not trying to force them kicking and screaming to follow your process, but at the same time, making sure that you do have a process and it feels like you're doing. So that's at the kind of the front end. And then if we come to the back end and we look at some of the things that we're seeing consistently, One of the most interesting trends that we see, and we've seen it for a decade and it's not going away, is that customers see the salespeople and the pre-salespeople as the personification of the brand that they're buying from. If they score you really well in terms of cultural fit, in terms of the quality of your team, again, that correlates really strongly to win rate because one of the criteria that's jumped to the top of the list from a decision-making perspective in the last Certainly 2 or 3 quarters is risk. Risk has jumped really far up the food chain to the very top of the list. So if risk is a really important decision criteria for customers, then it makes sense that they're going to want to work with that, those vendors that will mitigate and manage their risks and share their risks more than others. And then it starts to be, who are the team on the park? Who are the actual people we're going to be engaging with? How responsive are they? What are they going to be like from an account management perspective? Do they understand our risk factors? Have they built them into the proposal documents? Are they doing back-to-back SLAs with us? And a bunch of other stuff. So we're seeing some vendors get really smart and astute about how they have the risk conversation and how they then factor that into the commercials. If I was talking to your listeners and I was saying, here's the 3 or 4 things to think about, I would say, think about the way you're doing your discovery. Think about your responsiveness. Go deeper on risk and be easier to buy from. And if you can do those four things, you put yourself in a really strong position to to win more than your fair share of the opportunities that you're pursuing at the moment.

Yeah, that's fantastic. And I think that what you've laid out here is again lifting the bar on what I often see sales teams. getting focused on because even starting with— some people just talk about being consultative, which is one subsection of being of good discovery. But going through the 4 stages as you've outlined it is going to cover so much more ground than what they're currently doing. And I can just see that having a huge impact. I have to mention, I was talking to Chris Wood on this podcast and he talked about MedPic. A couple of months back. And what he said, something that really resonated and stuck with me. And he said that trust is important in teams, but not enough people talk about transparency. Transparency is where you are willing, you can create an environment where people feel safe, that information needs to be shared, discussed, analyzed, questioned. And I just wonder, In an environment where you've lost a deal and people are either trying to protect themselves or afraid of reprisal for having lost a deal. Tell me a little bit more about that. What is your thought on how to create a safe environment and an environment where people are willing to embrace not only the wins, but the losses and the information that they might have contributed to themselves?

That's a really good question, Priya. And I think it was one of the big concerns I had in my mind when I started out on this path a decade ago. The first thing I'd say is, having done win-loss reviews for as long as I have, I could count on one hand the number of times we've had really negative feedback from a customer about an individual. Because if they're taking the time to give feedback, they're usually either positive or constructive. It's not really in their best interest to just be negative. So There's very few people getting thrown under buses in the reviews that we do, but they often will be constructive. So let's assume that you've received some constructive feedback. It now speaks to the culture of the vendor. Are they the sort of organization that looks for scapegoats? Are they the sort of organization that is trying to point the finger of blame for a big loss? Because if they are, hopefully from our perspective, we've realized that early enough in the piece that we actually don't work with them. There's been a couple of occasions where we've worked with companies, we found out a bunch of stuff for them. And then unfortunately, they have either done one of two things, either tried to use that as a stick to beat the sales team with, or they've said, this is all too politically sensitive, and they've just swept it back under the carpet. We try and qualify out those sort of organizations as early as we can, because there's no point doing this because they just don't have the appetite, A, to hear it, and B, to take action. But The vast majority of companies that we've worked with are really open to listening and then being really proactive. And the really best ones, what they do is they actually close the loop with the customer and they say, hey, you know that thing you told us? This is what we've done to fix that. This is how we've done to address that. This is the impact your feedback has had. Because when we started to build our SaaS offering about 2 years ago, one of the things we did was we went and looked at what does everyone hate about surveys? And there's an awful lot of stuff that people hate about surveys. Like, the list goes on and on and on. And we tried to reverse engineer as much of that out of our platform as we could. But one of the things that people hate about surveys is, I don't know what you're going to do with my answers. I don't know how you're going to use them. I don't know if you're even going to listen to them or take action on them. And so as a result, quite often we just don't do it because it feels like a waste of time. So for us, the reason we get as much really detailed feedback as we do is not because of anything amazing that we do. It's because if you've done a good job as a salesperson, You've created a level of professional courtesy with your customer and they want to reciprocate some value back to you. And if giving 5 or 10 minutes worth of feedback is valuable to you, they're actually really willing and prepared to do that. And if you explain it to them appropriately, they'll actually be really candid in the feedback they give you as well. Sometimes they'll talk about your competitors. Sometimes they won't. Sometimes they'll go into detail about pricing. Sometimes they won't. But pretty much everything else is open season. They'll answer questions and they'll be very honest in that feedback. But you have to culturally as an organization be really open to feedback as a gift. Whatever we get is a positive. At least we're extracting some value from our effort and our cost of sale, and we'll get better next time around. So there's a vendor that we're doing some work with at the moment, and they're probably the best organization I've ever seen in terms of taking action. So what they do is they get our feedback and then they traffic light it. Red is negative, orange is neutral, green is good. And then they put work teams on what are we going to do to move the needle in each of these areas? And then they close the loop back with the customer and say, this is what we've done based on what you told us. Just best practice. We didn't tell them to do that. That's just their own internal initiative. But they lose less, they win more. They're winning bigger deals. They're taking more market share. Now they've started asking us if we can go in and analyze from their existing customers how happy they are, how much return on investment they're getting, what else could they do for them. So they're just really proactive in their thinking. And we have this untapped resource, which is all of this feedback and goodwill from our customers and our prospects. And so many businesses are walking away. Their cost of sales should have paid for that, but they're walking away because they just don't understand or they don't have a mechanism to capture it. And so they just continue to make the same mistakes time after time.

Yes. I can just see the ramifications downstream. When you don't have a capture and analysis mechanism in place, because when I look at forecasts and QBRs and deal reviews, it's very much being reported by the team internally. It is, it does not include the customer, the voice of the customer. And when you look at CRM systems, which are populated by feedback that the team has put in there, it's very one-sided sometimes. So I think to have— tell me a little bit, we've got a little more time.

Okay.

Let's— tell us about your platform. Why do you need a platform? Tell me about your platform, because that just seems an amazing and a no-brainer for any organization to be able to capture customer intelligence and actually achieve some true competitive advantage, especially at a time when deals are fewer and timelines are extended. It seems super, super relevant that they have a platform like the one that you offer.

So for years, we've been doing win-loss reviews by interviewing key people on the customer side. And that's great, but it's also expensive and time-consuming. So we tended only to do that on very large, very strategic deals, which meant only big businesses could afford to do it. But people kept asking me, random people were asking me, hey, could you do this on smaller deals? Could you do it on $20K deals or $50K deals or $100K deals? And I was like, I actually don't know. And then when COVID hit, I'd been, I had this idea rolling around in my head for the longest time. So COVID hit, I wasn't traveling, I had a little bit more time on my hands. I had a really great technical guy that I'd done some work with previously. And I said to him, look, I have this idea, I want to see if we could take what we do as a consulting service and build it into a platform. Can you work with me? And let's see if we can just create a little clickable prototype. So we did that. And we took it and showed it to some folks and said, if we were to build this thing, would you be interested? And the feedback was, yeah, I don't know if you could do it. But yes, we would. So we're like, okay, let's take everything we've learned. Let's chunk it down to what could be a 5, 6, or 7-minute review for a customer. So we built that and then we tested it and we said, okay, all we need is your opportunity data. So bring out your data, your wins, your losses, and your do-nothing outcomes. Give us that customer data and we'll do the outreach on your behalf. And lo and behold, customers started responding and giving us a bunch of feedback, really detailed, really honest, really candid. We were asking them to record their voice or video or type text in as well as answer the quantitative questions. We didn't know if they'd do that. They did. They did it. We didn't know if we'd get 2 out of 100. Some of our customers are getting 80, 90% response rate. And again, it's not because of us. It's because they're asking for it. And it's a really valid resource. So now we've just announced our partnership with Salesforce. We'll be building it into the Salesforce CRM system so that people can click without ever leaving Salesforce, click win-loss review and schedule it. And then the feedback will come back in, never having to leave CRM, which has been a dream of mine for the longest time, but I never knew If it would work or how we would do it. And now we're at that point. So my view is this, irrespective of the size of organization you are, if you're B2B, if you're putting in a reasonable amount of time and effort and energy into your sales pursuits, you deserve to get some value back in return, something you can use to test and improve what you do. I use the sporting analogy all the time. You should be watching the game tape back and learning from it. If you want to call yourself a professional, a sales professional, you've got to do professional things. We can't continue to act like amateurs and call ourselves professionals. So that's what we're doing. We're trying to add in one step at the end of the sales cycle that we all know so well. And that step is, irrespective of the outcome, win-loss review. Irrespective of the outcome, capture some feedback. Irrespective of the outcome, get some value in return.

Kieran, amazing. I can just think of so many situations that It would have—it would affect customers. It would affect careers. It would affect quotas. It would affect pressure levels. It's just affecting everything. So, thank you so much. This has been an incredible masterclass, so as to speak, in terms of what companies can. And I would encourage anyone who listens to that and is tired of losing deals but not having any insight and actually. creating a best-in-class team and a best-in-class career and a best-in-class organization to get in touch with Kian. So thank you today. Thank you for joining us and thank you for sharing this with me.

My pleasure, Preet. It was great to be here as always.

Fantastic. Thank you.