
Pillar Talk: Building Sales Leadership with Rick Smolen
Join Rick Smolen and other seasoned B2B sales leaders on the quest for defining great sales leadership. Learn the pillars of successful leadership, hear stories about what works and what doesn’t, lessons learned, and come away with specific tactics you can apply to your job or career right now.
Pillar Talk: Building Sales Leadership with Rick Smolen
Checklists, Coaching, and Conversion: Sales Leadership Lessons from Wade Callison
Wade Callison, CRO of Files.com, shares his journey from product leadership to sales and reveals how technical domain expertise creates credibility that transforms selling relationships from transactional to consultative.
Curiosity, coachability, growth mindset, and self-awareness form Wade's core framework for identifying and developing sales talent.
Wade details creating a culture of continuous learning helps sales teams adapt and improve. In one example, Wade outlines the pre-call brief that models it's thinking on the pre-flight plan that pilots benefit from.
Currently focused on improving win rates at Files.com, Wade shares his strategic approach: rather than trying to fix everything at once, he's identified specific leverage points like establishing value before discussing price and strengthening champion enablement. This targeted methodology exemplifies the thoughtful, measured leadership style that has defined his career.
Whether you're an aspiring sales leader or looking to refine your coaching approach, Wade's insights offer practical guidance for transforming individual contributors into cohesive, high-performing teams. Connect with him on LinkedIn to continue the conversation and exchange ideas about sales leadership excellence.
Music by Ben Cina & Ayler Young
Hello everyone and welcome to another episode of Pillar Talk, where we build the foundations of sales leadership and create clarity in terms of what good looks like for current and aspiring sales leaders. Before we jump in, I always like to review what the six pillars of successful sales leadership are, or what I came up with to try to define what the behaviors of good leadership is in a sales leadership capacity. It starts with talent, identification and attraction. Obviously, building and maintaining the team of winners is critical to success. Building your overall operating rhythm of how you run the business. Business planning, which is your cross-functional collaboration to make decisions for the future rather than continuously reacting to the events that are happening to you.
Speaker 1:We have communication, which, in the world we live in today, takes many mediums and many forms. Ownership, which is about how much do you, as a leader, do on your own versus looking for direction, and it's also about how much are you about your team versus being about the business, and how do you find balance between the two. The last one and obviously like, at the end of the day, when you're in sales trying to grow a business, mastering the craft, how do you help your team win? So we've got lots of elements that we explore in this podcast to try to provide tactical insights and actions to help aspiring leaders be better at the actual task of sales leadership. So today joining us on Pillar Talk, we have Wade Callison. Wade is a sales leader currently serving as the CRO of Filescom, a file transfer automation company. Along with many other things that Files can do, wade previously served in sales leadership positions at ActiveVM, squid and Intralinks, just to name a few. Wade, welcome to Pillar Talk.
Speaker 2:Thanks, rick, good to be here.
Speaker 1:Yeah, it's good to be with you. So, Wade, you recently relocated from the Northeast down to Texas. What's one story of surprise that you didn't anticipate in terms of doing that of surprise that you didn't anticipate in terms of doing that.
Speaker 2:You know it's just been the all the logistics of relocating. We've been in the Northeast for 16 years and you end up accumulating a lot of life with four kids over 16 years and for us it's just been all the logistics. It's been exciting, but it's definitely been been something that has taxed us over the last few months, especially with starting a new job. Starting a new job and moving it's like all the major stressors of your life all in the same way. But we're loving being down in Austin. It's a great city. It's been really welcoming to us, so it's been a lot of fun.
Speaker 1:Well, congratulations. Thank you, wade. When our paths have crossed in the past, one of the roles that I observed you perform in is as probably the most strategic account executive in the organization. You did not work in a context where you had a repeatable solution and you simply went and tried to maximize the volume of purchases that got made, but you had to create solutions on a curated basis based on strategic customers, and so I thought what we would cover today is focus on mastering the craft I saved. You know the best for last year and how you evolved in the days of being a strategic account executive into a leader that is helping to coach and help the team ultimately win. As you have grown in a leadership capacity, were there any formative moments? Were there any lessons learned along the way that helped set the stage for how you pragmatically or practically coach and help your team win today?
Speaker 2:Yeah, look for me. I didn't come to sales in the typical journey. I didn't come out of college and go to be a BDR or a salesperson. I really spent a bulk of my career in consulting in product companies. In fact, when you and I first met, I was running a product organization and was enjoying and loving that and I felt like my whole career that I was a bit of a closeted salesperson. I was always a salesperson but never actually had the guts to go be one.
Speaker 2:And I went to our former chief revenue officer, who ended up becoming the CEO, and I said to him after a sales kickoff I stood on stage and rolled out this brand new product and then afterwards I said to him I said I think I want to be a salesperson and he's like do you think you can be a salesperson?
Speaker 2:I said I think I can. He said if you can't, I'll fire you. I said if I can't do it, you should fire me, right? And so I went into being a salesperson, thinking that it was just those intrinsic skills, like, oh, I'm a good salesperson, I think I can be a good salesperson because I have, I think, the intrinsic skills. And what I quickly realized is I knew nothing about selling, like mean again, we have these intrinsic skills, but like I had to become a student of the game and I had to learn and I had no idea what I was doing and and it really comes back to some of the core points which is, I think intrinsically someone has to want to learn and grow and from that there's so much you can pour into them and for me it was that right. It was that moment of having a lot of experience and thinking you know what you're doing and figuring it out and having those people teach me.
Speaker 1:Yeah, that's really funny. It reminds me just. A lot of people think you know the sales team is, like you know, higher compensation. It's easy. They just complain about product like different things, like I could do that, and when you're thrust in it it's a very different experience it's so hard.
Speaker 2:It's so hard like when I, when I first met with our cro, he showed me one of the organizations I was selling to and we put an order. He goes who do you know? And I had one name for this global bank and he's like okay, next time we meet you should know more of the people there. And we built out the org. But, like again, these are the skills that you just have to pour into people.
Speaker 1:So, as you entered a sort of sales career and again this is going to lead to how you coach today you got thrust in and saw from the deep end, so to speak, the challenges associated with success in you know, winning deals, hitting numbers, doing that type of thing, and your realization about how important you know coaching is going to be to the success here was in once you were thrust in. Was there a time, as you started to evolve and succeed, where you were able to get the type of coaching that impacted you or you know able to get the type of coaching that impacted you or, you know, enabled you to be?
Speaker 2:better equipped to succeed. Absolutely like everywhere I've been, I've looked for that ability for my leadership to be able to impart wisdom upon me, like when I went to squid. Squid was an interesting place for me because I had been again advanced in my career I'd been a seller but I hadn't gotten all the skills of being a sales leader and I found a CRO who was just a servant leader who would pour himself into me and into his team and would allow you to fail, would help you, coach you and help you coach other people, and I think it's finding those mentors in each of our lives, like for me it was those people, but also it's the peers that I have that I go to. Like I've called you at times for help. I've called other sales leaders that are my peers for help. I think it's all about finding those people around you that can help you understand and help you learn those skills that you need.
Speaker 1:So when you had great mentorship, as an example CRO at Squid, are there any stories of how that came to build up your ability to impact others?
Speaker 2:Yeah. So what he was really good at was this cadence of look always be open and communicate, but then also build in the technical skills with the team. So we would obviously all of us going to be working on discovery skills and negotiation everything else but one of the things he believed which is I believe deeply is that sellers need to be a have full command over their domain and in having command over your domain, the best sellers like in the jolt effect when you read Matt Dixon's book and Ted McKenna the seller that can carry the deal the furthest without relying on their team around them is the one that is viewed with credibility and the one that can sit shoulder to shoulder with the customer and help them solve a problem, as opposed to being across the table trying to do a commercial agreement. That's very clearly not in everyone's best interest, right? So I think that making sure and one of the things that Rob did well, the CRO was we had a monthly talking tech where we went deep into topics that the sales team needed to know, and because of my product background, my computer science background, that's how I always sold.
Speaker 2:I always sold from a place of credibility and it always helped me and in fact I've had a CTO of one of the large law firms. Stop me, he goes. You don't feel like any other salesperson. I'll say what do you mean? He goes you feel like you know a lot about the topic you're selling and I think that's what I value in my team, the team I've got here at Files. That's the skill that I value the most, and why it was a good fit for me is that my CEO and I both believe that you should be as close to an expert in your domain on the topic that you're selling, not just an expert in selling, and it makes a huge difference.
Speaker 1:Now, when you say domain, you're referring to the context. It's not just the product, it's not just the market, it's where those two elements meet. One of the things that is interesting to me, wade, is that the path for a successful seller isn't a one-size-fits-all, and so some can lean into their expertise. So, for example, in my current company we basically hire sales team members that come from industry the taxonomy, the my current company we basically hire sales team members that come from industry the taxonomy, the pain points. It's a vertical SaaS business that's so far in our growth, you know, provides higher confidence of their success. So they do tend to have much more subject matter expertise.
Speaker 1:But that's not the only option here. It sounds like in your career, what's given you the most comfort around your path to success is around building that level of like. I understand the customer, I understand the problem, I understand how we meet that problem along the way and I can engage successfully because I'm bringing real expertise to. You know any given sales situation. Did you find that? That you know like there were other paths where you had to coach a little bit differently on somebody that maybe their skill set isn't as strong in the technical sides, but they bring much more process. They bring much more structure and other elements of the deal, and how have you handled it?
Speaker 2:Yeah, and I should say, like with yours, yours is verticalized. I've tended in my career to go with horizontal platforms, ones that one of my sales reps said were more liquid than solids. We're not selling a solid thing, we're really being more consultative in the selling. So those are the sorts of environments I lean into and the sorts of environments that I like. Which then changes the selling skills, and I think to your point is that we do get people who have industry experience, but it's more around the horizontal.
Speaker 2:So for us here it's around network infrastructure, it's around the protocols on business-to-business integration, sftp, managed file transfer, these sorts of things, and so you need to understand that domain, you need to understand the architectures, because when you're talking with our customers and I've said this to one of my reps yesterday we see more of those than any of our customers who are buying. We know what it takes to migrate from one legacy environment to the cloud, and our customers are doing it for the first, maybe second time in their career, and so we need to be able to provide that sort of guidance. And so if you are deep into this domain, if you care and you're curious about what it takes to do that, then we can be that Sherpa that helps them on their journey to get to more success.
Speaker 1:So sure. So you, as an individual contributor, leaned into your technical skills and understanding the customer and the problem as a way to help solve issues for them, which is fantastic. You then become a leader and now you've got a whole team of people, and one of the things a new leader tends to run into is that the path that works for them isn't necessarily the same for all the individuals. How did you address that dynamic where everybody on your team wasn't just like you?
Speaker 2:Yeah, no, and thank goodness they're not. It would be a horrible team if it was. Yeah, no, and thank goodness they're not. It would be a horrible team if it was. Look, it's about a as me, but I do think there's some things that really matter in being able to sell and sell effectively, and those skills are things that we sit and diagnose. I work with my managers to sit and diagnose and then to invest in the individual. But again, I think for me it's one thing for us to diagnose that, but the individual seller has to know and recognize that and want that feedback and want to grow.
Speaker 2:I just had a one-on-one with one of my reps yesterday. He said can we make our one-on-ones longer? There's so many things I want to learn and so many ways I want to develop and I need more time with you to be able to do that. And that's the sort of person that I'm willing to pour all of my time into, because they're the ones that are listening to a thousand gong calls, like anyone who listens to more gong calls than I do is probably someone who's trying to get to the next level. Those are some of the indicators I look for and so, yeah, it is difficult, but again, it's about a plan, for what are the skills that you are lacking? Whether they're technical, whether they're selling, whether they're just interpersonal skills Like empathy for me, is one of the biggest skills that I think, as a seller, we need to have, and we need to understand what it means to buy and the risks that it takes to buy in this sort of environment.
Speaker 1:Do you have a list of skills that you've sort of developed that define how you coach?
Speaker 2:Yeah, so I mean, there's a set of skills that, as an individual, that I expect you to have. Number one is curiosity. I want you to be absolutely curious about your customer, their environment, and genuinely curious. Like we all know the difference between an interrogation and genuine curiosity. One of the best reps that ever did this was a rep you and I worked with in the past and he was childlike in his questioning. He was fearless, he would ask questions and it was so disarming that the customer would answer them, and there were questions that I'd be like, ooh, we shouldn't ask that. But he was just genuinely curious and he wanted to ask that question. He wanted to earnestly know, and that's so disarming and it's great. And so curiosity is number one. The second is coachability. I want someone some of the best individuals that I've ever worked with had played athletics on an athletic team at some level and they know what coaching feels like. They don't take it badly, they want it, they seek it and you can give it to them very directly and they, they take that on and they, they, they change right and they try it. The next call and I just had a rep come into me five minutes before we spoke hey, the thing you were telling me. I tried on this call and it did help and it worked. Thank you, um.
Speaker 2:The third one for me is a growth mindset. I want someone who again wants to grow, wants to intrinsically get better. I've worked with people in their career that are late in their career, and I've worked with people early in their career Like some of the folks on my team at one of my stops were in their 60s and that worked for this environment and this organization. Some of them had a growth mindset, others didn't right, and those again, when you're later in your career, it's easier to think you've got it all figured out, but I don't know about you, but I haven't got it figured out. I'm learning it every day.
Speaker 2:I'm a first-time CRO. There's things I learn every single day about how to do this job better, and for me it's about that growth mindset. And then the last one really is around self-awareness is that Are we self-aware of where we are good and where we're not? One of the things that struck me about you on your last podcast with the CRO from Gong was you said look, there are some things I need to get better at, your self-awareness about the things you need to get better at. Personally, stuck with me, it's easy for us to think that we've all got it figured out. We don't, and so I think that this self-awareness and ability to reflect and and own them so those are the more soft skills.
Speaker 1:What about the types of technical skills or other sales skills associated with your you know, coaching strategy or how you'll develop folks?
Speaker 2:yeah, look, I mean, like I said, the number one is that sort of domain skill. So the domain skill in what you're selling, you need to be as close to an expert as you can be in that area. Now it's going to be difficult because if you're selling into an expert field you're never going to be as expert as the expert. But you still need to have that ability and depth and knowledge and curiosity to learn and to grow in these, like when I know, when I was a new rep selling into banking, there's so much about these large international banks I know nothing about and you learn and you guide and you do that. And then there's all those the selling skills and again, I'm not going to go through all the selling skills, but there's there's a ton of selling skills around better discovery.
Speaker 2:One of the things we're struggling with here right now, frankly and again I'm not going to go through all the selling skills, but there's a ton of selling skills around better discovery. One of the things we're struggling with here right now, frankly, is we do a lot of technical discovery and in my diagnostics in the first 90 days here, I've realized we don't do a lot of business discovery Our people were so trained to do technical discovery that they know everything about the environment and they don't really know the why behind the problem. And so here we're focusing on digging into okay, be curious about the business domain, understand what matters, understand the impact of why a failure or something is impactful for the business, and so there's a lot of skills like that around negotiation. I know for me, I'm always reading because, like these things like negotiation, that we all only do infrequently in deals and we need got to get better at it. Like we do a lot of discovery, we don't do as many negotiations, and so we need to get better at those.
Speaker 1:Wade, in your career you've been at varied businesses at different sizes and in different levels of maturity different levels of maturity. Do you have you formulated a coaching framework Like is there a process that Wade uses that's independent of the business that you're in? That helps give you confidence that you can make the team better, because you know what I'm thinking of? It's really funny. It's like as somebody moves into leadership, and especially if they've been successful at sales, the sales team then goes to them from help and the easier thing for the leader to do is what? Do it for them right? It's the easiest thing, right. And so now they start to build a dependency.
Speaker 1:Now the leader is doing some of the things that the salesperson finds more difficult and the individual contributor isn't learning. In fact, they're learning a dependency. And so now the sales leader is doing so much. It didn't happen right away, it happened slowly. They started doing this for one person, then something else for another, and this dependency starts to build and all of a sudden the salesperson has got a pretty good life and the sales manager is like burning out completely. And so one of the challenges around coaching is this whole idea of like how do I get individuals on my team to perform at a high level but not take the easy road, which is that do it for them. That's all right there, especially if you're actually good at sales.
Speaker 2:Yeah, look, I've actually made that mistake. I, in one of my stops, became the person who could deliver the message the best and I would find myself taking over these sales calls and I realized that at one point I was like this is not helping anyone. I felt pretty good about myself because look at me, I'm really good at delivering this and customers are being attracted. But that's that super salesperson and that just does not work, and I think for me it's become a bias, for coaching is while I had this conversation in this last week with one of my reps is that he was talking about his progression in his career, whether he wanted to be a sales leader or not, and I said look. I said all of us like the deals you're working on I view as my deals. I just delegated them to you to execute on them and execute on a well, your deals. You should feel like you're bringing people around you to help you deliver them, but not be dependent upon them and no one's stepping in. And so when I'm looking for leaders and we're hiring a bunch of leaders right now, number one is a bias for coaching, not a bias for taking over, and I think for me that's one of the skills that it's. It's a hard one. You have to have learned it, you have to have those battle scars. We're saying, yeah, I've tried that it didn't work, and so that's one of them.
Speaker 2:But your question originally was do I have a framework that I bring in?
Speaker 2:And frankly, I don't have one yet. And it's one of those things that I know what I value and I know what I do and I'm situationally applying that. But it's not been one of those things that I have really looked at codifying a framework, because for me it's been each environment is environment slightly different. I've got a set of things I believe in and a set of things that I I look for and I really apply those in differently and independently. So, like the business of active VM was two-year sales cycles, large financial services organizations in the world, a category that didn't exist. So we're creating need in a category, very different things and we had to coach very differently than here, which is known categories, technology, modernization, technology replacement, different people in their sales journeys, and so for me I found that it's been very different. So I haven't been able to apply necessarily a framework yet, but I do have a set of things that I believe in and believe in deeply, and the things that I also know that I look out for and make sure that I don't do.
Speaker 1:What are the things that are consistent? Is it the frequency of one-on-ones? Is it the way you do call reviews? Is it the way pipeline management turns into forecasting? What are the tactics that you've learned that are helping you? Sometimes it's solving more than one thing. Coaching in and of itself is nice.
Speaker 2:Coaching within one thing, like coaching in and of itself is nice. Coaching within the context of your operating rhythm, as an example, is like even better. So one of the things that's been new for me, so call coaching has been awesome. I've done that for a while. We were talking about gom earlier, and call coaching transformed everything. What I find with with call reviews that way is it gives you some independent insights. But one of the things I just embarked on a project and just got the results back was using AI to do a longitudinal view across all my projects and all my sales calls, rather, and so we took 141 sales calls, ran through an engine and looked for those things that, across the board, were not doing well, and so for me, that gave me a lot of points of coaching where I didn't have to listen to 141 calls. Some of the things were things that I had experienced, but some of them I hadn't picked up on yet because it's difficult to do that. So I think that leveraging technology to do it has helped.
Speaker 2:Definitely, call reviews, definitely one-on-ones. I mean, I'm a big for one-on-ones. I was in an organization that said that maybe we shouldn't be doing one-on-ones, we should only be doing it in a team setting? I don't know for me I love a one-on-one because it's a chance for us to have a very specific conversation. I do like coaching individually, but I also like coaching in a team setting because everyone learns from it. But I'm a big one for that conversation, that structure.
Speaker 1:How's a one-on-one happen with Wade Like? Is it structured? Is it informal? I'm literally trying to figure out because I also agree that one on ones are important and you know, but I am also a bit of an extrovert. So, like I like to interact with people, I know other people want a one on one only if there's like a detailed agenda, because they like to be focused on work and don't want to be distracted. How do you approach it?
Speaker 2:So what I've done is what I found is each individual likes their one-on-ones to go a different way, and I've done it where I've done them structured and it didn't seem to fit all the cases. And so what I now do is I have a set of topics that I'd like to go through right. We typically talk about a deal, we typically talk about some of the issues that they're experiencing in their pipeline or whatever else, but it's really very specific in their development. But what I do is I put a list out and they can add topics to the list. Some of them come with a full list of topics that they've thought out ahead of time. Some of them show up and are winging it, and it tells me something whether they are sort of thinking about this and investing in that time as something in their development or not.
Speaker 2:If they sort of come in and wing it, that tells me one thing it's not necessarily bad, it just tells me something For those that have. All right, I've got 12 things on my list I need to talk to you today about, and they go through that right. So for me I'd leave it a little bit more open. Definitely try to focus on the similar sort of topics in there, but I let the rep also dictate what they need from me, because in a lot of cases I'm serving them in their ability to close business on my behalf, and so I want them to also pull from me, as opposed to me just always pushing into them.
Speaker 1:What does it say about some? Like you do see high variability in preparation for a one-on-one with somebody senior in the org, and I agree with you, it doesn't like the level of preparation doesn't necessarily matter. Like some people are just not focused on that. They have a list for the things they're focused on, like maybe their pipeline, but I don't know what to extrapolate from that huge variance in repetition. I think perhaps as a leader, one of the things I think about is am I setting a clear enough stage around, like what a good one-on-one should look like or what I consider to be, and creating a bit of a roadmap to how I think we make best use of the time? At the same time, it's not all about me, so it's a tough balance to kind of strike it might be.
Speaker 2:It might be all about you. Here's my thing is that whether you come in with a list or not is a data point. Whether you're prepared or not can be something separate. If you come in and you're unprepared, we're going to talk about you coming in unprepared. That's going to be the conversation. But if you come in prepared and you don't have a list, that's okay. Some people use lists For us. I tell you one of the things that we do on calls which is, I think, really valuable and it's different than what we're talking about. But we started this pre-call brief and it's like a pilot does before they take off, and our reps jump on a call five to 10 minutes before the prospect and they talk about that call, what they're preparing to do, what they're preparing to learn, and they do that. They do that out loud to the recording so that they've really prepared themselves for that. So I do think that prep is important.
Speaker 1:This sounds interesting. Let's talk about this pre-call brief.
Speaker 2:Yeah, I have not heard this before I know like it is something new here.
Speaker 2:So our ceo is a pilot, um, and one of the things he believes is that, as a pilot, the important part of flying the plane is doing that pre-flight brief, making sure that everything like the checklist manifesto.
Speaker 2:If you haven't read a tool gawande's checklist manifesto, love the book very simple, but it's really about we do the things that we have a checklist for and we get better at that repetition.
Speaker 2:And so his point of view on this was if you go into a call and haven't really thought about and articulated what your goals are for the call, then you likely are going to miss something. And so the fact of preparing for that pre-call brief, saying it out loud okay, this is the call I'm going into with this person in this title, this is what I need to learn, this is what I need to understand, this is my goals for the meeting. Then that allows me, as a leader as well, when I do a call review, to see what they said they were going to accomplish and where they were going and how they actually executed against that and it's much, it's really helpful. My team started to get out of doing it a couple of weeks ago and I was like, guys, this matters, get back to doing it again. And now they've raised the bar again and they're doing it every call. So it's huge.
Speaker 1:Just the mechanism with which this happens. How do they?
Speaker 2:they do it they jump on their zoom call. So we use zoom with our customers. It's the same.
Speaker 1:Okay, so they jump into the zoom link for the meeting that's coming up.
Speaker 2:They just jump in five minutes before the the scheduled time and we use a waiting room, we use the waiting room feature in zoom, so we don't let the customer, we don't let the prospect in yet, and so, like sometimes, a prospect will join three minutes early and you're like you don't want to be caught in the middle of your preflag yeah, yeah, 100 weird, but yes, we jump in five minutes early, we record that and then we let them into the call and so, um, I think it's, I think it helps us make sure we're prepared again back to a culture of being prepared.
Speaker 2:That's the way, one of the ways, we're being prepared for those calls you mentioned what I need to learn, goals for the meeting, what else so it is.
Speaker 2:Who am I meeting with? What do I know about the business? This is john from this organization. They do this sort of thing from the lead. I understand that they have this type of problem. I need to dig into that problem some more to find out this, that and the other, and they'll talk about that. And then my goal for the meeting is to learn this and to get this type of problem. I need to dig into that problem some more to find out this, that and the other, and they'll talk about that. And then my goal for the meeting is to learn this and to get this sort of outcome so we can have a next step. And so that'll be the way we lay it out when you get into subsequent calls. So that's for a sort of first discovery For subsequent calls.
Speaker 2:We in our CRM are using the winning by design spiced as our framework, with medic as a layer in it, and what I've asked them to do is for each one of those within situation and pain have the discovery questions written that they want to ask in the next subsequent calls. So in their pre-flight or their pre-call brief, they're going back through those to make sure they know hey, I've got these six questions. I'm going to try to ask these three today to make sure that I can move the deal forward and do that as well. So it's sort of bringing in their own deal analysis, their own assessment of where they are in their deal lifecycle into that to make sure that they thought about. You can't ask 20 questions in a call. It becomes an interrogation. So what are the three or four that really matter to move your deal to the next stage.
Speaker 1:Really interesting how long on average is this pre-call brief? Is it a minute? Is it a few minutes? It's like two to three minutes.
Speaker 2:When you do it, you sort of feel like there's only so much Now.
Speaker 1:some of them may last a little longer, but two to three minutes, yeah, sure, it depends on the situation. But as somebody then that is, reviewing a call or reviewing a deal with someone I'm guessing that you are finding just that early setup helpful in how you'll process and digest what you observe in the meeting itself.
Speaker 2:Yeah, yeah, and it helps the rep do that, because they've already thought about where they're going. They've thought about the mile markers in this call that they're going to try to hit. It helps me and my managers also review it, because you know you go into a call you don't know what you're going to get. You say I'm going to listen to this call and it's like five minutes of them just talking about the weekend and then you're like, okay, where do we get to the meet? And at least if I know where they're going, I can then listen for those sort of things and I can use the AI to ask those questions as well.
Speaker 1:Yeah, have you helped equip the team with like I don't know how to most efficiently prepare a pre-gall brief, or is it's like let them figure out the way that works for them?
Speaker 2:we've been. We've been working on standardizing that, reviewing those and standardizing, and I think that to this it's there's a certain individual style to it, but again, you need to have it laid out and we need to understand what your goals are for the call. What do you know? What are your goals are for the call, what do you know, what are your goals are and how do you know when you've accomplished what you set out to do in that call.
Speaker 1:I keep asking questions because I observe the same thing. And, look, there's a human element to being in sales, especially when you are getting inbound inquiries, which obviously not everybody is fortunate to receive. But you get into a groove, you're comfortable, you know your domain as an example, and it's fun to learn from the individuals that you're about to engage with. And a thing that can fall down by the wayside is that preparation. And so, on the one hand, how should I prepare? You're looking to standardize that but, more importantly than the how is just the effort. It's just the effort, and I think my hypothesis here is just by simply doing that, to all the points you made, the sales rep now has a bit of discipline, can enter the conversation, having done some work, and you have a verification element around that. And then, as it relates to coaching, you now know what the because.
Speaker 1:Think about a coaching call in the absence of this. Now I'm kind of playing with this concept. Is you start? The first half of the coaching call is like what were you trying to achieve? What was the goal of the meeting? What was, what were you hoping to learn? Which is like meeting.
Speaker 2:What were you hoping to learn? Which in?
Speaker 1:hindsight is a very different answer.
Speaker 2:Yeah right, exactly. It's easy to re-engineer where you got to right.
Speaker 1:I love those fun little things that we can do to a small change that can have a big ripple effect on how our team goes to market.
Speaker 2:I think the third one is you mentioned two aspects that it provided, but also it provides a different mindset for the rep going in, their mindset is slightly different than if they just come in cold. They come in, yes, they're prepared, yes, they have a plan, but they're also then with a mindset of okay, I'm settled. I can now get into this and I know where I'm going Because, to your point, we get all inbound leads. We're blessed with an all inbound motion today. I've never been anywhere with that. It's awesome, love it. Now I get to build an outbound, but the inbound is such high variability and again, getting that lead and trying to figure out what is this person trying to accomplish today and what. Where do I want to take them and how do I take them from where they are to where it points to our differentiation. And that's part of that conversation and you need to be prepared for it.
Speaker 1:Wade, I imagine in a high inbound environment, that one of the challenges associated is with qualification and there's probably a chance that there's a high volume of opportunities that will get disqualified after a call. Is it your view that that preparation or that pre-call brief is still just as relevant in a world where there might be a decent size disqualification rate, or is there some type of factoring into that?
Speaker 2:No, in fact, part of the pre-call brief is hey look, I don't think this is going to be a good fit for us. I'm going to try to figure this out and disqualify this as soon as possible. Some of them that come to us will be a 10-person company with, like, they've just started and they've got a small budget and you know what? They're a good customer for us, but they're a good customer through our self-service channel, not through the direct channel. And what I'm trying to train the reps on is every deal is not a great deal for you. Just because they're a good customer for filescom doesn't mean they're a good one for you as a seller. So let's try to get them to the self-service channel and do that. We try to catch that as the SDRs, but some of them go through. But yeah, it is very useful for those that you want to disqualify out early.
Speaker 1:Yeah, so what I'm hearing you say is relevancy to all, even if just doing that preparation will lead to getting clarity that this should be disqualified or not. Yeah, yeah exactly Super interesting. What other tools are you using, what other ways are you seeing to be able to prepare the team to win more?
Speaker 2:So I go back to the conversation. One of the things that I'm working on right now is win rate. So our win rate, again against industry metrics, is probably about six, seven points off of where it should be, and part of that AI project was finding those places where we are not doing. We're not executing the way we need to, and, for now, what we're working on right now is a set of sales plays to be able to put the rep in the best position. I've got this strong belief and I don't know if you've thought about this. So when an NFL team gets their game plan for a game, they script the first 10 plays of the game, no matter down and distance. I'm going to run these plays in this order and then after that they've learned what the defense is giving them, how they align, like all the things you need to learn in those first 10 plays, and then you run down in distance, and I think that for us, what we're working on is getting those first two to three calls really well understood and then running a set of situational plays after that. And so what we're working on now is how do you sell value before price?
Speaker 2:We get a lot of people in the first call hey, can you give me your price? And our reps were like give them price out. And all that happens when you give price out in the first call is they disqualify you because they're like oh, you're too expensive, you've done a bunch of discovery and you've given them a price. There's no reason for them to think you're worth that. And so we're working on some things in those first two to three calls that are more scripted again, not fully scripted, but like we know where we want you to go, we know how you want to handle each of these scenarios, and then from that we're putting in a set of plays that are then more situational so it's just like a discovery guide.
Speaker 1:Is that essentially what you're trying to do? More than that?
Speaker 2:it's more than that, because discovery so. So there's a big component of this discovery. So for us again, I said earlier we do a lot of technical discovery, not much business discovery. So then the question is how do you do better business discovery? How are you not just thrashing around in the pool and like asking a bunch of random questions? How are you really getting to the right questions in the right way? But the second is is that? How do you then start to articulate value early and differentiation early? What is the way to do that? We're working on our shifting, our positioning and our messaging to help that. But also, how do you arm the rep in that moment to start to shift the conversation from the discovery into the value conversation?
Speaker 2:One of the things we've got a bad habit of doing I'm sure a lot of people do is you can hear it in sales calls is how many users do you have, how many of this, how many of that? And they're really asking pricing questions, right, and they're veiling them as discovery. And it's not really discovery, it's just really pricing. Like I'm trying to figure out how to price. And I think that one of the things I've observed is that customers realize what you're doing. Therefore, they're like okay, now can you give me a price, because you've conditioned them.
Speaker 2:But wait, so you're spot on Help me understand what you're doing to change that. So what I'm doing is actually so a couple things One, stop asking price questions in the first call. That's what I'm saying scripting. The second call will be about pricing questions. So make the first call about technical and business discovery.
Speaker 2:We are then putting in a small vignette type demo. Again, it's not a full demo, but it's a little bit of. We compete against really clunky old SFTP managed file transfer servers that are just horrible to use. So I want them to show a little bit of our product, because if we say it's easy to use, there's no baseline or metric for you are much easier to use and I can see why that's valuable. So I want them to show a little bit of the product and then I want them to be able to get into some some value conversation to the next step. So differentiation a little bit of demo and get out of that in the first call and the second call will set up okay, we'll do a proper demo for you and then do some pricing discovery and then we can then get to a price either by the end of the second call or the third call.
Speaker 2:But at least we've been able to go through our version of the story and how do you handle those questions which is, hey, can you give me your price? How do you handle that in that moment? Do you give them a price? Do you dance around? I want them to be very consistent in how to handle that question and so that they don't feel slimy, they have empathy and it's honest, it's like, look, we don't lose on price, but I don't know enough yet about your environment. I'd like to get into a little bit more before we, before we go into that, is that okay with you? And then it's, then it's something that is is in the customers best interest, as opposed to something where you're being being, we are withholding information from them.
Speaker 1:Level of like change that you're observing as you work this through? Like. Is it a hard change or is it, like, not that complicated? Like? How would you rate that?
Speaker 2:Look for me. My sales team are incredible and they're taking it on and they're learning and they're applying it immediately. So, again, depending on your environment, I'm blessed with a team that is just the right type of people who are learning it, and they are thirsty for this sort of change because they want their win rates Again.
Speaker 2:This whole project is for us, win rates. We're focused on win rates, and that focuses on putting money in their pockets, and so they all know why we're doing it. We're not doing it for any other reason other than we want them to earn more, and so they're taking it on and they're trying it, and they're coming back and saying, okay, this worked, this didn't. Can you listen to my call and tell me what I did wrong or what I could have done differently? And, frankly, we're adjusting our scripts and what we think our hypotheses don't always survive right, we think we know what it is, but the six foot conversation that we have is really where it plays out, and if we're good at that and we learn from that, we can help them get it better and better. So it's on me and my leadership team to adapt and change the battle plan with them to be able to do that better.
Speaker 1:But if I paraphrase what you've been talking about, it's like hey, we have an objective which is to improve our win rates by six to seven points. One of the reasons that we think our win rates are lower than they could be the six to seven points is because we aren't having the value-based conversation early on. We're sort of going right into, like, offering price and answering their questions, and there's a belief that if we can just push off that aspect of the process until later and just focus on, like, maybe, some business discovery and some technical discovery for fit and get permission from the customer to do that, that that will set us up for the customer to better understand the value that they would get, which would provide a different lens when they get to the actual price point. And if we just do that, we think that will have the biggest impact in terms of improving win rates. Is that a right way to think about it?
Speaker 2:It is. The only thing I would add to that is that we've also identified champion. Enablement is an area where we fall down as well. So, yes, we can do all that, but when the person that you're talking with goes and takes it back to the economic buyer, are they prepared to have that conversation? And we're getting much better at doing that. That's something that's difficult for someone in an organization to go sell that internally and we want to be again shoulder to shoulder with them, helping them get this project funded and going, because it's good for their career and it's good for them personally to be able to get this going, so we want to be the one to go alongside of them.
Speaker 2:I don't know, you and I were talking about being a buyer. As sales leaders, we don't often get to be buyers. I was a buyer once for an account-based marketing software and I have to tell you, every sales pitch sounded the same, every product and every one. I wanted to say get me to the product demo. And every time I got to the product demo I was like I don't care about your product, I can't tell the difference. I wanted someone to tell me account-based marketing initiatives fail for these three reasons, and we'll help you make sure that it doesn't fail, because, as a as a revenue leader, if I had gone after an account based marketing um software package and program and it's gone belly up, it would have looked bad on me and that's really all I cared about. And I don't think we do enough of that is making sure that people understand what it feels like to buy and what and the risks that we have.
Speaker 1:And that part of champion enablement is making sure that person's confident that this will be successful, and I don't think we would spend enough time on that yeah, and that plays into some of the things you mentioned around the jolt effect and customer indecision laid in a deal and how you got to have bring confidence that, like I got you, it's no longer about it's about?
Speaker 2:it's about like, hey, we're gonna go do some great things here and we're gonna make it a win yeah, and look, I mean, that book for me is one of the best books that in in selling, that I've read in many years, and I think that one of the things that I try to model and this goes back to coaching with my team is I've got a stack of books on my desk. I always, always am recommending one. You and I work for a leader who would always talk about the book he's reading, and I asked him about why he did it. He said because I want everyone to know that I am an avid learner and I don't care whether you read my book or not, but I want you to have a point of view on. You're an avid learner too, and we share books that are great for us great for us and so like that's.
Speaker 1:That's the sort of culture that I want to encourage. Well, we've actually referred to a couple of books here Checklist Manifesto. We've got Jolt Effect. What's one more that maybe you'd recommend for aspiring leaders that you've recently read that had an impact on you?
Speaker 2:You know the one is. Let me get the right title of it, it was Super Communicators, I think. Have you read Super Communicators?
Speaker 1:I'm not.
Speaker 2:You know, this was one that, as I came here, the leadership here had read, and it's about those people who, in the way they talk, open up information in people that other people don't. And these super communicators, you can spot them and they're the ones who ask the insightful question, the question behind the question, and they're the one who don't start with, hey, so like, what do you do for work? Right, that's like one of those most the trite ones.
Speaker 1:They're the ones where you're based Exactly. I'm weathering Milwaukee today.
Speaker 2:Yeah, there's a guy actually from our past that would said the best open ended discovery questions. Hey, tell me your life story, because in that way yeah that's yeah. Yeah, I mean it's. Yeah, I mean, when Brian says that, you think yeah, because what he's doing is he's getting you to stop and think where do I start and how do I learn? And I think that finding those sort of super communicators and those skills as being a super communicator has been huge. So yeah, that's another one, awesome, all right.
Speaker 1:Well, now I have homework coming out of this Wade. Where can people find you if they have any questions? They want to follow up on anything we discussed.
Speaker 2:Yeah, so obviously on LinkedIn, happy to connect with anyone. I love having a big community on LinkedIn and I'm happy to be a resource to people there, and then obviously, we can connect over email. Also, I'm a member of Pavilion, so if anyone's in Pavilion you can hit me up through Pavilion as well. But happy to be a resource and if you've got something I can learn from you, I'd love to do that as well.
Speaker 1:Well, wade, I want to thank you for being on Pillar Talk. It was great catching up with you. I can't wait to read a new book and to get into this pre-call brief aspects and some of the other areas we covered. We'll talk to you soon Awesome Thanks.
Speaker 1:Reflecting on the conversation with Wade Callison, you know Wade's been in sales and sales leadership now for so many years. I think I had forgotten about the fact that before sales, wade came from a product background and I loved how he described his transition into sales and it reminded me that sales as a job often looks so easy to those on the outside, but it's a totally different ballgame once you're on the inside, and it makes sense to me that what led to Wade's success and what he continues to lean on today is his technical and domain skills in order to succeed, and it's what he looks for in new team members as well. We got into coaching, which I love. An aspect of the interview that stood out in that area was that tactic that they enabled called the pre-call brief. As Wade had mentioned, the CEO of Files is a pilot, and I love this connection between a pre-flight plan that a pilot sets up in order to succeed on the flight and the quote-unquote flight that a seller is going to go through in the journey with a buyer and that simple tactic of spending the time to define what the rep is hoping to learn and the goals for the meeting, that simple change. It's not a big ask it creates. To me it creates two things More consistency in the prep of a seller, meaning sellers are more consistently preparing for the meeting, which is just an important discipline that we foster. That translates to better sales conversations. But it also accelerates the leader or the manager's ability to coach, because now the manager knows, going in, what to actually be coaching for.
Speaker 1:And lastly, I enjoyed the focus Wade described for looking to enact change in the organization based on like a single metric In this case he talked about win rate and that Wade has found just two areas of coaching opportunities in order to improve win rate. The two areas that Wade described are getting to value early instead of those interrogative pricing related questions, and then champion enablement to help towards the end of the deal. I kind of think about like if you were trying to coach somebody on a golf swing and you tried to tell them to work on six different things. Of course that's not going to work. You got to start with like one or two things and that's sort of what wade is doing here in his coaching in order to affect a single metric. So, you know, wade now puts himself in a position to actually help his team improve and that result actually helping the team get better.
Speaker 1:Well, that's what this podcast is all about. So I want to thank wade callison for joining in this episode of pillar talk. Thanks to ari smolin for producing. I want to thank eiler young and sons of summerolin for producing. I want to thank Isler Young and Sons of Summer for the tunes and I want to thank you for joining. We will see you next time, on the next episode of Pillar Talk hurts in me like the joke I can't shake, I can't quit.
Speaker 2:It's never really what you said it was. All you're doing is break the trust.