00:00:00 Will Collinge: The critical reflection and analysis only really seems to happen upon failure — and that's why it's so important. It's about how do we get better every single day? The thing we've learned is that everything can change throughout a sales cycle. Something you heard a year ago from a senior person might not be true anymore. Small things shift. Maybe someone moved to a different team. Maybe their focus changed. Maybe something else happened in the business. But for us, the key thing was to go back and verify what happened in the decision process. When did it change? Just checking in weekly about the information you have — sitting in the deal review, everything looks great, metrics are fantastic, success criteria, paper process all on track — when did we last check that was actually accurate? Because things can change quite quickly. 00:00:54 Pim Roelofsen: Hey everybody, this is another episode of Elite Dealers. And today we have a very special guest — someone who reached out to our company when I had just started, so it's been a while. Today he is a Regional Director at LexisNexis. Introducing Will Collinge. Welcome to the podcast. 00:01:09 Will Collinge: Thanks, Pim. Great to be here. 00:01:11 Pim Roelofsen: So, for today we're going to get into a couple of topics. The first is a deal that actually went to loss — and is, you know, still in play again. The second part of this conversation will be about complex stakeholder management through enterprise selling — something you and your team know a lot about, because you're a second-line leader now. And since you're on this journey of a MEDDICC initiative with your organization, we're going to dive into some of the learnings you've already had and some of the pitfalls that people thinking about doing the same thing should be mindful of. That's the agenda for today. So, hey, why don't we get right into it — let's talk about that deal you didn't win just yet? 00:02:04 Will Collinge: Yeah, sounds good. I think it's really important to talk about losses. I want to say upfront that we had a great year last year — pretty much every single person hit their number, five Presidents Clubs, it was fantastic. But the point is, the critical reflection and analysis only really seems to happen upon failure — and that's why it's so important. How do we get better every single day? I want to talk about a deal that we lost, and talk about why we lost it, because I think we learn so much more from our losses than our successes. And losing isn't a bad thing as long as you don't make the same mistake twice. So, running through it: this was a sales cycle with a tier-one bank in Europe, and it lasted about 18 months. We did everything right. We found the pain above the noise. We had fantastic champions who identified it, articulated it, implicated it. We ran a fantastic proof of value. The customer understood the decision criteria and decision process. We went through the paper process. I'm skipping forward quite a few steps — but we got to the board meeting, presented at the board meeting, proved the metrics: we're going to save them X billions of dollars per year, the customer experience improvement will go up by X, the operational savings are proven. We presented to the board. They asked us to step out for the second half and made their decision. And we found out we'd lost — or it was a "not now, but maybe later." We just couldn't believe it. Couldn't work out what had gone wrong. We'd done everything right. We had the right champions. We'd met the economic buyers. We had executive-level engagement. We'd agreed the success criteria. But something we kind of glossed over was that the scope changed toward the end. And you might think scope increasing is a good thing — an extra country being added, more value, more everything, it's great. What happened when the scope changed was that it added one more economic buyer, late in the day. And we had to bring in one more person. But we didn't go back to reconfirm everything we'd learned over the previous 18 months. And what happened was that this new economic buyer came from a country that had a really specific data regulation requirement that we didn't understand. Essentially the decision process and the success criteria changed midway through — and we didn't know about it. And it was something we couldn't really overcome at that time. When we had the debrief, we learned exactly what happened. 00:04:47 Will Collinge: The really key lesson for us was triangulation — checking and verifying again and again and again. One of the things we added to our deal reviews and the way we use MEDDICC is a separate field: when was this specific piece of information last triangulated, and who was it with? Because in these enterprise deals, sometimes I have 30 people on the org chart, it's very political, and sometimes the things we hear aren't true. You can't take anything at face value. The thing we've learned is that everything can change throughout a sales cycle. Something you heard a year ago from a senior person might not still be true — small things shift. Maybe someone moved to a different team, maybe their focus changed, maybe something else happened in the business. For us, the key thing was to go back and verify: what happened in the decision process, when did it change? Just sitting in a deal review — everything looks great, metrics are fantastic, success criteria, paper process all on track — when did we last check that was actually accurate? Because things can change quite quickly. It was a really important learning. And now we can go back with a better structure and different things in place to try and close it this year. But yeah, it was a learning we had to make. 00:06:07 Pim Roelofsen: I think first question here — no matter whether you operate in a true enterprise environment with this many stakeholders or something more mid-market, it's not uncommon for a new stakeholder to come in somewhere mid-cycle and throw a spanner in the works. That's what this sounds like. And correct me if I'm wrong — this wasn't necessarily an economic decision criteria that you missed. It remained a technical decision criteria on the basis of a new country. Is that right? 00:06:32 Will Collinge: Yeah. It was a specific piece of regulation that our champion didn't know about. When the new person came in, we were checking in — is everything still the same? Yes. But we only did it with one person, and we didn't triangulate and double check: this new economic buyer coming in, what does this change? What does that mean? 00:06:52 Pim Roelofsen: So you didn't know that this person was coming in via your champion? Or did the new EB arrive completely as a surprise? 00:07:00 Will Collinge: We knew they were coming in — we just underestimated the impact it would have. And I guess the point is we trusted our champion to understand the impact as well. And they didn't, either. 00:07:09 Pim Roelofsen: Will, I want to go back to something you said at the very beginning — that you learn a lot from mistakes and failures, and that's the mindset you need. I love that. I want to understand how you're using this example with your team now, today, so that it doesn't happen again. You already mentioned the triangulation reminder — can you share a little bit more about how you're taking this example and arming yourself against it happening again? 00:07:46 Will Collinge: Yeah — we carry the scars, right. It was painful. Two things. First is the templates and the way we do deal reviews. Now there are specific prompts for every single category of MEDDICC — whether it's metrics, economic buyer, paper process, champion — and the separate points we review are: when was this last checked, who said it, and how many people have you checked it with? So for example, if we have a metric saying this is going to save this much time, which equals this much cost, which equals this much benefit to the business — when did we last check that? "It was confirmed in June." Great piece of information. But that was eight months ago. I'm not saying it's changed, but let's go back and double-check, because things change quickly: new people join, people leave. That's the first thing. And then secondly, if only one person provided that information, I want to hear it from two or three more people as well. It's going back and checking: who said it, and when — dating the information. I think that was one of the key things we missed in our MEDDICC reviews last time. The MEDDICC looked fantastic but the information was undated. There were no dates against specific pieces of information. So how fresh actually is it? If you're working on a sales cycle of more than six, twelve, eighteen months, that can really come back and bite you. And then secondly, doing loss reviews — and making clear that it isn't a blame session. We're not giving people pats on the back for closing deals, and we're not telling people off for losing deals. We do the proper analysis: what went right, what went wrong. Changing the way we do deal reviews, and tracking and collecting the right information — and doing loss reviews in a safe environment where people can talk openly. If you've made a mistake once, I'm totally fine with that. We all make mistakes — you have to make them to grow. Making it twice, that's where I have a problem. But the first time, if we acknowledge it and understand it and put something in place, like they happen to all of us. 00:09:59 Pim Roelofsen: Will, is a loss review something you do with just the frontline leader and the individual contributor, or more collectively with the broader team? 00:10:07 Will Collinge: We try to do it with the team. We're all busy — obviously we're also actively trying to close deals at the same time, so I don't want to take up people's time unnecessarily. But if it's a problem that I think other people on the team face, or something that may have happened before and could happen again, then yes, we do it collectively with the salespeople. The key thing is it's a safe environment. This isn't about blame — we all know we lost it, we've all moved on from that. It's about: do we know what the mistake was, and what can we put in place to make sure we don't make it again? Creating that safe environment is so important, because otherwise it doesn't foster people wanting to engage. It's difficult — it takes a certain type of person to be honest and open and willing to share. But if you've got people with a growth mindset who genuinely want to get better, they will share. "Here's what I've learned from what I lost." 00:11:00 Pim Roelofsen: For me, this goes 100% back to culture. If people feel they can be vulnerable and transparent, and can say "this is why I think we're struggling," then the collective can lean in and level up together. When we think about everything related to MEDDICC, we always say it can only truly thrive in a culture of trust — where people can put their hand up and say, "I've probably got an issue here and I need help," rather than feeling that the onus is entirely on them. So I love this. When we were getting into this session I said we'd probably wrap up with a couple of key takeaways, but whilst you were talking I'd already noted down about eight different things — specifically on the loss review. Because I believe this is a cadence that revenue teams, and especially leaders, should embrace more. Making sure people understand it's a safe environment, considering whether the issue from a specific loss review is relevant across the rest of the team, and underpinning it all with a culture of trust. Is that a fair assessment of the criteria for leaders to think about? 00:12:28 Will Collinge: Yeah, for sure. And one thing I'd add — we've had deal reviews where people only want to share the deals that look fantastic. And that's really not the point. We're all implicated in this together. The perfect time to do a deal review is actually after just one discovery meeting — the earlier the better. And completing the MEDDICC doesn't mean you'll win. There's no prize for completing it. Having gaps is fine — I'd much rather have gaps than false information. So the culture point is so important, and it does take time. But it's really important that this isn't criticism — it's helping each other, because we're all in it together. Having someone take notes, someone doing research, others engaged in active discussion. Someone saying, "I had a very similar situation with a prospect last year — I thought about approaching it this way and it worked." It has to come down to how people feel about being vulnerable and sharing in a team environment. 00:13:38 Pim Roelofsen: Yeah, 100%. I feel there's a risk that you and I could go very deep on deal reviews and talk for another hour on this topic alone — so I'm going to park it for a minute. I know we're going to talk about learnings from your actual MEDDICC implementation. But first — can you talk to us about where you are now with the account you lost? 00:13:55 Will Collinge: Yes. It's an existing customer, so I don't want to go into too much detail. But it's about nurturing now. We understand the regulation. We understand the specific problem we couldn't really overcome. Now it's about staying close. There is something coming — I think in about 18 months — that changes that regulation. So it's about being ready to implement by that point. In those 18 months: nurturing, staying close, regular catch-ups, keeping the theme alive. The pain is still there — it doesn't go away. The pain is actually getting worse every day. So we keep measuring it, keep it alive. The sales cycle is extended. We're not going to forecast it for this year, but it's something I want that salesperson to continue to work on, because it will happen next year. It's just about having a long-term mindset on it. 00:14:56 Pim Roelofsen: That's very clear. And let's agree right now — once this deal has been won next year, Will, we'll do another one of these and talk about it properly. 00:15:05 Will Collinge: That'll be another failure session and loss review! 00:15:08 Pim Roelofsen: Ha! For now, where I'd like to go next is another deal — one that I know you won — with immensely complicated stakeholder management within that account. Where do we start? What's the first thing that comes to mind when you think about that deal? 00:15:35 Will Collinge: Politics. And how you try to ignore them, but you can't — and then they come back. That triangulation piece again. The sheer amount of data you get in these deals is overwhelming. If you take a large bank — at board level you might have eight to ten people, of which you probably have two or three economic buyers across operations, technology and compliance. Within those teams there are hundreds of people. There are working groups you need to engage with to advance the project, and the information you share at board level is very different to what you share with the working group, and vice versa. I can think of examples where we found some really interesting and specific pain — really compelling metrics around the cost to the business every single day — and we shared that with the board and got quite a few people internally in trouble. Going back to that "sharing the ugly thing" point: we did the right thing in discovery, we had really interesting information that would have helped the business case for everyone. We probably shared it the right way but with the wrong people at that moment. So the question becomes: you have the information, do you share it or not? It's absolutely key to the business case. But in doing that, you might alienate people who could be potential champions. It's really tough. It keeps coming back to politics, and it keeps coming back to documenting what people say, being honest about it, and sharing it carefully internally. 00:17:27 Pim Roelofsen: And in this context — the working groups you're describing, are these where your champions would typically reside? 00:17:48 Will Collinge: Yeah, it depends. If there's a live project — for example, migrating all critical applications to the cloud — there'll be a working group analyzing vendors who can help with that. You typically find a champion within that working group. But you're not sitting in that working group yourself. So if you already have a relationship with an EB and you have a commitment to update them on a monthly basis, the working group will want to control all the information flowing upwards — which is absolutely correct, and it's how the bank works. But you have those existing commitments and access to those senior people. So what do you do? You've made commitments to these senior stakeholders, and it's the right thing to bring them along. But in doing so, you can upset a few people, and we've found ourselves in that situation several times. The way you manage it is by remembering that these are people, this is their career. Some people at these banks have been there for 20, 30 years. They want to protect their position. You have to be really careful and conscious about that. Even though you've got a great deal and you're confident in it, these are still people — and without them, you won't get the deal closed. It's really challenging to manage, but it all comes back to politics. It takes a village to bring everyone along. And sometimes in doing that, you do upset people along the way. 00:18:58 Pim Roelofsen: So, talking about stakeholder management in a big bank multimillion-dollar contract with many different stakeholders on their end — how does that mirror on your side? What's the number of stakeholders involved on your side of this? 00:19:17 Will Collinge: Good question. Quick answer: between eight and fifteen, maybe. One thing that's really helped in my career is implicating senior leaders in our deals. It's helped with exposure — for me and for my teams and the deals we work on. And when you bring them in, obviously the key thing is making sure the executive-to-executive meeting is set up right. We have two or three execs plugged in to a senior contact on their side — they have their meetings, it's fantastic, and it helps us move things along. But when you have internal blockers, having that executive aligned and bought into the deal makes it a lot easier to have negotiations internally — whether that's a product problem, a pricing issue, or something else. The most important alignment for me is executive alignment across technology and product. Sales? Not that often, to be totally honest — it's usually product or technology that can speak the same language as a CTO or CDO. So yes, it takes a huge team. But that executive implication has been so important in these big deals. 00:20:51 Pim Roelofsen: And in this context, how did you go about getting EB access and engagement? Was it by implicating your leadership internally first, and then using them to multithread? 00:21:00 Will Collinge: A few ways. I always think that if the customer has a pain that you understand — and it's linked to a CEO, CIO, or CDO objective, or it's listed in their annual report or corporate objectives for the year — then you have the right to go direct. So for example: "Mr or Mrs CEO, you mentioned this in your annual statement. This is the impact. This is how we solve the problem. Can we set up a call?" Going direct works if the pain is stated, linked to corporate objectives, and you phrase it correctly. I also find events really useful. You'll notice which events senior execs attend, where they're speaking. Something as simple as sending a LinkedIn message beforehand letting them know you'll be there and asking for five minutes afterwards. And then yes, executive introductions — using your own network. You'd be surprised how many connections senior leaders in your business have if they've come from banks or big tech companies. And then the executive-to-executive introduction is great because they can talk about the specific technology challenges at a different level than a straight sales conversation. Going direct, and the executive introduction, are the two things that typically work. Some of these organizations simply won't take a meeting unless it comes from the same level on your side. 00:22:31 Pim Roelofsen: For me, a lot of this goes back to something you were talking about a few minutes ago — trust. As a leader, are you making sure your team knows you're available to enter these engagements? I actually posted about this recently: my hypothesis is that if you're not in the trenches with your reps, they either don't feel you can add value — which is something to solve for — or they don't feel you're available, which is also something to solve for. And if you start treating it as a leading indicator — "as a first or second-line leader, I want to be in prospect meetings at least this many times every week or month" — you can start making real impact. Because if there's no executive alignment, many EB engagements don't land. So if you start thinking about measuring EB engagement as a KPI and then working out how to improve it, much of that comes down to leveraging the executive team on your side. And that's a two-way exchange — while AEs and individual contributors can do a lot, it still takes that senior leader to make themselves available, and to make sure reps feel comfortable pulling them in. 00:24:20 Will Collinge: Yeah, we've found our company is great at this — if we need customer meetings, people make themselves available. My CEO will call me beforehand if it's a C-level conversation, and you have to make sure you do the prep and they feel comfortable. But they're willing to support, which is great. And it's a really interesting point about leaders attending meetings — I've always thought it's the most important part of the job. Gong is great and Salesforce is great, but if you're in a full customer meeting and all you can review afterwards is the call recording and the notes in Salesforce, you're missing it. You need to be there and do it. And you can't spend all day reviewing Gong recordings either. If I say, as a leader, "I want to attend five customer meetings every week" — all of a sudden I want to be in those meetings to show we're all in this together, we're all implicated in it together, and this is something I can help with. You can coach on the fly. And I'll be honest — I never want to be one of those leaders who just sits behind a spreadsheet or Salesforce all day. That's the fun part, isn't it? Being in the difficult situations, being tested and challenged — that's the good bit. 00:25:35 Pim Roelofsen: Yeah, absolutely. And the one thing I'd add is: thinking back to the best leaders I've worked with — and I deliberately say with, not for — they were always there in the trenches with me. It was not necessarily me always asking; it was also them making sure I was comfortable pulling them in and leaning into it. Some leaders have that naturally, especially those who've been selling until fairly recently. The other side of the coin is the spreadsheet-only environment, which isn't great. But with my VP, if I said tonight, "I need you to get on a flight to Amsterdam," he'd get on the flight — because I've seen him do it all year long. And then you feel you're genuinely in it together. Team sport. 00:26:39 Will Collinge: Well, that's a good point. And if you do come to Amsterdam — let me know, I'm around! 00:26:43 Pim Roelofsen: Right. Let's get into the last part, because we opened by saying you work at a company where we get to partner on the MEDDICC initiative. It's been 614 days since that first email. So — what have we learned? What are some pitfalls and things you'd share with anyone looking to do something similar — embedding MEDDICC into the day-to-day of how the team works? 00:27:17 Will Collinge: It takes time. Don't expect to do the training and then have everyone immediately aligned. You will have people who resist it. But I think the beauty of MEDDICC is that a lot of the best salespeople are already doing it — it's just about formalizing it and filling in the parts that get missed. So some of the lessons: it takes time, it's about the language you use, it's about the cadences you have, it's about everyone being on the same page. I actually started doing MEDDICC in my team in 2021 — I did it by myself first, off my own back, after hearing about it from people in the industry. After about six months you could see the results. Then we did it with my team, then a couple more teams, and then it grew. So to come back to your question: the big bang approach — unless you've got a lot of champions and advocates from the top — is quite challenging. I'd pick one team or a couple of teams, run it for a defined period, and then have the key metrics to show it worked: we closed more deals, faster, at higher value. And this isn't another sales methodology that comes and goes every couple of years with a change in leadership. This works perfectly alongside your existing customer journey process. Start with a few key points — for the first few months, just get people really focused on one or two things. Champion. That's it. You'll get to paper process when you get to paper process. Once you've got the buy-in, you expand it to another team, and then to the full MEDDICC framework maybe after six months. If we'd tried to roll this out across the whole sales team from day one, people wouldn't have done it. We had to show them internally: here's the situation before, here's the situation after — and one of us can say, "I'm one of you, I can tell you it worked." Manageable champions, proof from a team that's done it, taking it step by step. But it takes time — in the deal reviews, in the catch-ups, in the one-to-ones, using the same language consistently. 00:29:46 Pim Roelofsen: I resonate with this a lot. I was a customer here before, in a pretty similar role to the one you're in at your company. And I'd say that in organizations where you don't necessarily have a lot of champions and top-level buying, or real commitment — "this is how we're going to do things going forward" — you'll get pockets of success, and your time to value with the MEDDICC initiative is just going to take longer. But I have seen customers where there was that top-level buy-in, a complete approach with commitment and conviction, and a plan to focus on chunks first — and they got to a point of second-nature MEDDICC collectively across a thousand people in under six months, at least from a language proficiency perspective. There's a very clear set of ingredients you need, and it typically starts with senior-level commitment, flowing through the layers of leadership — because leaders are a force multiplier for any initiative. They create the environment in which this will either thrive or die down. And not all MEDDICC is equal, right? Depending on where you've learned about it, your depth of understanding will vary. If you've worked with us, for example, you'll know about the ones and twos and threes. If you haven't, you probably don't. But that depth in training and enablement is great — and then the next step is recognizing that not all MEDDICC initiatives are equal either. You need to consider all these ingredients. For you and for me, it made sense to start with a small group, because the collective buy-in all the way from the top across a thousand people wasn't there from day one. That took time. But there are organizations that can do it more broadly from the start and get to a much faster time to value. It really depends on the ingredients you're working with and where someone like you — as a champion — sits in the organization. 00:32:36 Will Collinge: Strong sales leadership is a lot of it. And it does come from the top down. One thing I remember — digressing slightly — is that I've been on the other side of the buying process with you three or four times now. It was really interesting being a buyer while also learning MEDDICC, because I could see the situations I was being put into. When you were doing the right thing, Pim, you'd put me in quite uncomfortable situations: "We need to meet this person." And I was thinking, is it the right time? But you were right — we needed to meet that person. And before that, you and I needed to make sure we were completely aligned on the metrics and that the pain was articulated and implicated to the VP in a simple, concise way. If you have strong VP and strong leadership, it can really work. But that person has to be bought in. 00:33:14 Pim Roelofsen: And what you're describing are the signs of a strong champion — someone who challenges you before giving you access to an economic buyer is probably the best you can get from a champion. Because ultimately it takes coaching on how to win, and empowering a champion to sell on your behalf when you're not there. The vested interest was clear in your case. But there's a lot in that behavior — the pushing back a little, the "we need to be really concise and clear on this before I'll take you there" — that says a lot about the power and influence your proposed champion actually has. 00:33:57 Pim Roelofsen: Well, before we wrap up — is there one more key insight you'd want to share? 00:34:03 Will Collinge: I think the success of it comes down to what you said earlier — the environment you create. This isn't about blame. It's about all of us trying to get better together. It's not "you're being blamed for not having this or doing it that way" — it's "we can all get better by doing this together." Some people will want to join in straightaway, and that's great. Maybe it takes a bit longer for others, and that's okay too. The culture you create and the way you do it is as important as what you're actually doing. Most important: sales and revenue teams should want to get into it. That begins with the leader. The one thing that really hit hard for me was: when was this last checked? Because things change — especially in longer sales cycles of twelve to eighteen months. Dating your information, knowing where it stems from, is key. And the focused approach — this is what we do first, building MEDDICC maturity step by step — sometimes it's better to do fewer things but do them better, to ultimately get to that true second-nature stage. 00:35:23 Pim Roelofsen: Will, I absolutely loved having you on Elite Dealers. Thank you for contributing to another great episode. 00:35:30 Will Collinge: Thanks, Pim. Let's do it again. 00:35:33 Pim Roelofsen: Absolutely. And we'll mark the diary for about a year and a quarter from now to discuss the win. Deal? 00:35:40 Will Collinge: Sounds good. See you then.
