Your Sales Team Is Trading Curiosity for AI Shortcuts

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0:35Pick up that guide today at belaysolutions.com forward slash gravy or text gravy to 55123. This is the Sales Gravy Podcast. Hi, I'm Jeb Blunt, bestselling author, fanatical prospecting, objections, sales EQ, and inked. And I'm here to help you open more doors, close bigger deals, and rock your commission check. Welcome to the Sales Gravy podcast. I'm your host, Ashley Blunt. And today we're interviewing Jill Guardia. She is the Senior Vice President of Operations and Chief of Staff at Thought Industries. And Thought Industries is a core platform here at Sales Gravy. If you use Sales Gravy University at all, this is the platform that makes all of your learning happen.

1:13So Jill, thank you for joining us today on the podcast. There's a couple of different topics that I want to cover with you. And you have three levels of strategy that you like to discuss and your framework for keeping corporate, departmental and team strategies aligned. I know that's a challenge when you have a lot when you're trying to pull off, you know, quality learning content for learners that they'll consume, engage with and actually put into action. So can you tell me about some of those strategies and what that looks like? Yeah, absolutely. The strategy is really all about alignment. It starts with aligning with your executive, whoever that might be in your particular case.

1:50It could be the CEO, CRO, CCO. Someone at the executive level is the most important. And then I take it down one notch to a champion. The champion could be anyone in the organization, but someone who is not a lone wolf, really is a team player and wants to engage and give you feedback because they care about the end results. And then the next step is management. You start with management at the frontline level because the ability to align with your frontline leaders is what makes or breaks any sort of strategy. And then ultimately, while I said three levels, executive, champion, management, you really need the team engaged.

2:32So once you've set up those three from executive to champion to first line sales managers or first line managers, then the whole team engages and you're almost guaranteed success. Where in this process do you typically see the most challenges for teams? Because it is a top down approach and I'm sure communication is a very large part of this while you're getting everybody aligned and finding those champions. Yeah, I would say that communication is really critical in all of that. Depending on the size of your organization, you may have like, you know, a couple of people across different roles that really are your champions.

3:11So you broaden that from one to many, depending on what you're working through. because the obstacles typically come if you don't get that buy-in, right? If you try and force something as an enablement leader, which is really where my background is, are the one who is force feeding whatever the program is that you're trying to roll out. So having that level of champion or champions, depending on your organization, makes a difference because then when you go to your first line leaders, they know that some of their key people were engaged and helped you build through the final piece that you put together.

3:51So how are you identifying the champions? Because I feel like that's such an important piece of that to have those people, you know, even in the sales process, like you need your champions for you, even when you're speaking directly with the decision makers. Yeah, I think that's exactly right. It's very much like a sales process. So you may think that someone as your champion. And, you know, they might have been identified by someone else as your champion, but not actually buying into that. So I think you need to really work through with all of those levels. Start at the executive level, explain what a champion is, talk to them about what you're looking for, what type of commitment, and have the executive team nominate someone who maybe is already demonstrating the behavior or maybe is part of a pilot program internally, something that you could easily tap into them and extend that reach.

4:48And then the other way to look at that is sort of the first line managers, ask the first line managers who on your team could serve as a champion. So you're kind of creating this sandwich between the executive and the first line leaders of identifying who those champions are. And that goes a lot to ego because people want to be champions. They want to be recognized. And so if you say, you know, your CRO picked you or the first line leaders decided that you three people are the champions. And so you're going to work with the enablement team to build out this program. Usually they're very committed to that.

5:25Awesome. No, I love that. And, you know, we're always looking for champions So when we go to launch like learning paths and such for our clients, a lot of times what I'll recommend when we're working with whoever the buyer, the decision maker was, I'm always asking them like who can help implement this within your organization that's a more senior rep. So let me take you back to a prior employer where I had a much larger sales team than I have now. You were planning our annual kickoff. And in that game planning, we really wanted to identify more of a walk in their shoes concept. So rather than sort of traditional sales training, we were trying to do a little bit more of experiential training.

6:13And in order to do that, this particular company sold in vertical. So we had verticalized sales teams. And I went to each of the heads of each of the verticals, the VPs of each of the verticals. And I said, please identify a couple of people within your team, within the ranks, who can work with the enablement team to build out this walk in their shoes concept. These people really engaged with us. And at our kickoff, we actually turned rooms into what we called experience rooms. Let me even take the example a little bit deeper. So in the tech vertical, selling to tech companies, the team created basically startup funding model program where all of the salespeople broke up into teams.

7:06They had to come up with a concept. They had to do research on that concept. They had to propose what kind of funding they would want for Series A funding. And then they had to present to a committee. And that was across the entire kickoff. So we really did a very different program, but we did it because we started at the top and engaged the concept with the vice presidents of each of the verticals. And then they identified the champions who were in it every single day to support the sales enablement team to build out something that was really, truly an experiential learning. So, you know, that's the way I would kind of think about that is if somebody was trying to put this together, maybe not experiential learning, but the concept of building any sort of program that you need that level of buy in is really you start with someone at the leadership level.

8:03You explain the vision, you get their input, you sit down and you talk about what is it going to achieve? What are you looking to have as outcomes? How much time do you have? You know, what are the priorities and sort of build that framework in a sit down with the leadership. Then ask them who from your team can be engaged to support. They're not going to have to do the heavy lifting. We're not trying to push the work off to someone else whose responsibility might be to sell or to do customer success, but to be an advisor, an advocate, a sounding board, and then work with those champions. And once you've got next level of draft ready, then you sit down both the executives and the first line leaders and you review it.

8:53You get their feedback. And once you've gotten their feedback in a positive way, you know, take the critical input, make changes, et cetera, then you're ready to create. Now, that sounds like a really long process, which it could be depending, you know, if you're doing a kickoff, this could be six months in advance of the kickoff. Yeah. But it doesn't have to be a long extended process. You can do it in a couple of days if you're doing something that's more kind of like a monthly or quarterly event. You don't have to spend months and months and months to go through this process. I love how y 'all set that up by vertical, too, because I imagine the level of engagement as everybody was going through it was phenomenal.

9:33And I'm curious to know, what's the feedback y 'all received after that event from the learners themselves that were involved? Off the charts. I mean, this was an amazing event and one that really did take a lot of work from everybody involved in building it. And kickoffs typically do. As you know, I'm sure you do your own. There's so much work, but there's so much reward. And in this particular one, I mean, even an hour into the very first day, we were already getting incredible feedback. I can't believe how exciting this is. I can't believe how much I'm learning. You know, I'm really creating an empathy for my customer that I didn't have before.

10:13I really understand better about what they're going through. We really just nailed it perfectly. Unfortunately, I haven't had a chance to do something like that again, but the concept sticks with me and I'm sure with my entire team in terms of making sure that we really create an experience in an event like that. I love that. Well, kudos. That was an awesome way to approach that. One of the things that we see challenges with with sales teams is, you know, tech stack fatigue. And there now with AI, there's so many more tools out there for everybody to use. So between CRMs and LMS, and then, you know, everything in between to help organize data and plan your day if you're a field rep.

11:01You know, the big question here is having a high volume of tools. Is that helping reps sell rather than creating more administrative work? What are your thoughts around this? Because that's one of the challenges that we see with a lot of the organizations we work with is, you know, especially trying to continue to upskill them and continue moving as the sales environment changes because it changes so rapidly now, especially with the AI tools. How do you approach that with your team? This is a really challenging topic nowadays, especially. I think about when I see some of those infographics that just have hundreds or thousands of names of tools that you should be using.

11:41This is sort of what I've called the hundred tool trap. And it's really strangling our sellers because it's more than enough. It's way more than enough. And I think the purchasing or continuing to purchase tools is really the loudest voice in the room is the vendor selling to you and not the rep asking for tools. So I think that what we'll see is that AI isn't really going to expand the stack. I think it's going to collapse the stack, maybe not in a week or a month. But I think as AI gets smarter and some of the core tools we use incorporate more AI into them, I think we'll find we need less, not more.

12:29I agree with that because there's a platform we use specifically for project management. And the way that they've expanded how they're utilizing AI in the platform has kind of done that. Some other tools that I was considering to pull in rendered that unnecessary, which is awesome. But, you know, for the sales teams, how have you helped your team identify what's best for them? Because I know this is going to be different industry by industry, but how have you helped weed that down even while AI is scaling to help reduce that? Well, I think you have to look at usage. You may have inherited a tech stack.

13:08You may have been the decision maker in deciding what tools are in your stack. I think there's some probably core tools that at the moment are non-negotiable. Maybe over time they will be negotiable, but obviously you need a CRM. You know, you need an email system. You need probably some sort of customer intelligence tool, which is pretty broad. And some tool that helps you with your, I'm thinking sales at the moment, but some tool that helps you with your outreach, your prospecting, your pipeline building. And, you know, is that three tools or is that six tools? I don't really know. And I think you're right.

13:49It's going to depend on the organization and how they work and who they're selling to and things like that. But I don't think it's 30 tools or 60 tools. We're actually rolling out a paid for AI license within the organization. And we're working very closely with the sales team and the customer success team to really understand the way they work and see where we can optimize or create efficiencies in those core tools with some AI overlay, I guess is what I would call it, or plugins or skills or, you know, whatever they might be called in the particular tool that you're using. but I think we'll find that we don't need to buy a whole lot of more tools.

14:38I think we need to use the tools we have in a more effective manner. I love that. And I'm always looking for how can we generate greater efficiency with what we have. So thank you so much for sharing that. Going into a follow-up call, I want every important note right at my fingertips, not buried somewhere in a scribbled stack of notes. And with Plod Notepin S, I always have them because it's a wearable, portable note taker that lets me stay present and focused on customers during every single meeting. Plod captures the conversation and turns it into organized summaries and action items so I can follow up faster.

15:13And if I need a specific detail, Plod's recall has that ready for me. And that's why Jeb Sr. and I and all of Sales Gravy trusts our Plod Notepin S. Try Plod and stay focused on the conversation while it handles all of your notes. Go to plod.ai forward slash Jeb. That's plod.ai forward slash jeb and use code JEB to get 10 % off your purchase. The next topic that I'd like to cover with you is around your experiencing managing enablement at a high growth company like Thought Industries. Tell us what that's like and some of the lessons you've learned along the way. The way to start that conversation is that in high growth companies, you do have a lot of change.

15:54And this sounds so sort of cliche, but that is the key is managing the change, managing the expectations as best you can. You know, are you going to feel a thousand percent successful every single day? Absolutely not. Because change is happening at all levels, especially when you bring in a new leadership team. And I think that that is one of the places to start. They say that leadership, CRO, CCO, their tenure on average is 18 months. I don't know who they is, but I've read that. And so if it is true that 18 months is the tenure, then inevitably you're going to go through shifts in your leadership.

16:44Yep. And high growth companies, they don't have the patience to give it another quarter, another quarter, another quarter to see if it's going to change. And sometimes people have to take the brunt of that, right? And particularly in tech, we see it all the time. You're not making your numbers. And so, you know, the leader is exchanged for a new leader and new ideas. I'm not saying that that's exactly what happened. I'm just saying that's the generalization. So if I take myself into the place of being in charge of enablement at Thought Industries, I've been here for four years and I have seen some leadership change.

17:23And that means that each time a leader comes in, you have to build your own reputation with the leader. You have to get to know that leader and build a relationship with them. You have to understand their point of view, what they're passionate about, what their pet peeves are. And then you have to get to know the tactical, like what methodology do they like? Is that the methodology you use? Are you going to change methodologies? How do they coach? How do they manage? So all of those things is really where enablement has to not hold the line, but to translate on behalf of the leaders to help ensure that their vision can be expanded into essentially the reps Monday morning activity.

18:19Mm-hmm. Change management is something that every sales organization experiences, and tech is just a different animal. I've never sold in tech, and it is so difficult for me to wrap my mind around it because I have a background in automotive and telecom sales, services sales, that sort of thing. I imagine with the strategies we were talking about earlier, that's probably where you're deploying some of them as well in that enablement position to help with the change management. And, you know, I know that can get difficult for the sales team because 18 months, that's an interesting statistic because I feel like at 18 months, like you've gotten over the learning curve of learning what methodology they accept, you know, how they coach, how they communicate.

19:03And you're starting to, hopefully at that point, see all of the changes taking effect and the trends going upward. So that's interesting. I just hadn't thought about it. That way, because that is a disruption when you think about it. And disruptions can, you know, be difficult. It's almost like handling objections in a way. Yeah, exactly. And, you know, reps, the folks in the rank and file, they're not really doing much. They're not embracing change. Like reps don't say, yay, we've got some change going on. They just try and survive it. Right. And so surviving it means like, okay, I have to interpret the macro levels and then the micro levels.

19:50Like what does this mean to the organization, the culture? And then what does this mean to me so that I can get my day-to-day job done? And for an enablement leader, it's balancing that out because you're trying to respect the change that's going on, whether it's a new product, a new leader, a new investor, a new stage of the company. and make sure that that doesn't disrupt the day-to-day activities of reps, whether they're CSMs or account managers or account execs or BDRs, so much that they can't get their job done. So you are a little bit of kind of the mesh screen, you know, not like a wall or a door, but like the mesh screen of helping to embrace the embraceable and to digest the digestible in the change.

20:47I love that. And you know, something else you mentioned talking about changes that you manage are like the new product rollouts. So what does that look like for y 'all? Because I think it's just about once a quarter, there's a new update, there's a new feature, which our team is loving. We love it. We sign up for every single time as the end user, every single time we all are at the point of rolling out to your customers, we're signing up for the webinars because we want to stay on top of it and learn as well. But what does that look like internally for your sales team? How are y 'all educating them on what it does so they can relay that to the clients?

21:25Yeah, I would say that that's a bit of evolving and every company who sells a product or service has to kind of figure this one out. Let me tell you what we do do. Every month we have a hangout where our R &D team gives us the lay of the land. And of course, you know, that's recorded so we can listen to it after. You can listen to it multiple times. You can start to think about, you know, did I hear everything? Do I have further questions? All of that. And that's really important because you get to see what's coming down the path and start to think about how that will impact your conversations.

22:03Now, of course, there's a balancing act on that one, too, because you can't start talking about some things until you can start talking about some things. And so that happens every single month, like clockwork. And it's been happening for years and years. And it's really a very well-attended event. And we learn a lot. And we get to ask questions. We get to see demos. It's a great forum for whetting your appetite internally about what's coming. And then we have a Monday morning go-to-market team meeting. And probably once a month, we bring the representation from the product team to that. And that also just allows us to ask deeper questions from a selling and servicing point of view, which is super helpful.

22:52On top of that, we have kind of across the company stakeholder enablement function. We have what we've called a channel activation person that sits in the product team. Then we have product marketing, and then we have sales enablement, and then we have our own customer education team. And those are really the four key stakeholders that build the components that would include internal enablement, would include messaging, as well as customer facing materials, and then customer education pieces. is it's kind of a never stop learning about what's coming, especially because we have some new folks running our product and engineering team and they are just so amazing and so innovative.

23:43And we're doing some really great things that I think you'll be really pleased with. And we're really looking to ensure that you as customer get value out of the product that you purchased from us. So it sounds like y 'all have really woven it into the culture. So when you're bringing new hires into the fold, like from day one, this is the routine, this is the expectation. And I'm sure that helps with the adoption of the updates, especially since y 'all have a high volume of it. So I love that. I love the structure. And, you know, at least what I've noticed in leading change, even within our own organization, being able to have the expectation set and almost like a framework that you consistently follow.

24:25It doesn't make it feel as scary. Yeah, consistency is really critical. And, you know, I think the internal hangout call that we have with our product and R &D team, it's always a second Wednesday of every month. So it's like clockwork, right, which is really important. And I think you can extend that if you're an enablement team or you're part of this readiness group who's really working on ensuring that. Also think about standardizing communications, right? So, you know, it should never be a one and done. And so if you do an event and you have people come and learn and then there's a follow up communications and just making sure that you're consistent with all the pieces and not just one off things, because that doesn't help the situation, especially when, again, back to the rate of change is so fast these days that you have to be consistent.

25:18Otherwise, people don't get all the pieces. it. My next question is, so within these forums, and as much as your sales team and customer service reps talk to your client base, how often in the forums do y 'all actively hear feedback? Because you're bringing all the teams together. So you're bringing all the parts of the house together. How often do y 'all actively get feedback in those sessions from people saying, hey, my client experienced this, anything along those lines? Yeah, I mean, feedback comes in a lot of different ways, right? So I would say it's always on and there are different channels to get feedback.

25:56So anyone who's talking to a customer and gets feedback that way, we have some Slack channels that they can use to raise that. Of course, you can roll it up to your executive leader if you need to, and the executive leader will bring it across to the executive team. And then I think there are plenty of other ways when you have team meetings to share feedback that you're hearing in the community. You know, we have a community piece to our customer relationship so we can hear feedback directly from the community. And that's a great way to hear what's going on. In addition to that, you know, we do customer calls.

26:38Executives reach out and they make time with executives. We're hosting a dinner with one of our partners. And so, you know, we'll have some customers and some prospects there. And that's a great way. We have a roundtable coming up. So we're doing all sorts of forums that encourage feedback directly to the executive level as well to the folks who interact with them day to day. And then we have internal Slack channels and other forums where we can share that across the company and take action where action is needed. I love the accessibility of it and that it's flowing through the whole organization.

27:10So it's not just stopping at one level. So awesome. So the last thing that I want to cover with you is like the modern skills gap. What's the number one skill you see modern sellers missing in today's landscape? I might be a little controversial about the skill that I think is missing, but I think the big skill that's missing is curiosity. I like that. I don't disagree with you. because I have felt in some conversations that I've had recently that sellers have been operating off of a checklist of questions and they are lacking the natural curiosity. So I'd like to hear more. How did you come to that conclusion?

27:52What brought you there? Well, a couple of years, actually many years now going back, we actually did roll out a program of selling with curiosity, which is a program you might know. And ever since then, I've been sort of uber aware of the curiosity effect. And I think to your point about, you know, people have a list of questions that they ask and AI is making that worse, right? Because you literally could just go into your favorite AI tool and say, I'm meeting with sales gravy later today. I want to sell them my tool and I'll be talking to Ashley, what should I ask her? And it will give me 10, 15, 100 questions.

28:39And then I can just blow through them. Where are we creating a relationship if I do that? Where am I getting to know you? How am I really understanding the environment that you're in and how I might personalize what I'm trying to do with you, whether it's sell you something or just, you know, be an advocate for what you do. And so for me, I think that ever since that program, it's just occurred to me that people don't ask curiosity questions. They aren't curious. They just want to tick a box. Absolutely. I agree. And with the program that you put together, how do you feel the adoption went in the organization?

29:29Because I'm thinking about the personality of sellers and like even myself when I've been in that role, because you're so focused on trying to hit a number, it does get really easy to just go down the checklist, especially if you're trying to hit a high volume of appointments during the week. And, you know, All of that plays into it with the pressure that it adds. How would you coach an individual on not doing that? For me, that is thinking that discovery is a potentially never-ending process. There's a lot of tug and pull on this because, you know, a lot of organizations would look at, oh, we need to reduce our number of days in stage.

30:12We need to reduce our sales cycle by 20%. And what I would advocate for is expand your discovery days and stage, because the more you get to know, the faster things will move later on, including disqualifying when it's not a right fit. You know sooner that it's not going to fit. So for me, the way I would coach on that is don't try and go faster. The advantage is depth in discovery in particular. So slow down and do discovery until there's no more questions to answer. And it's crystal clear what the next step should be. And that will be hard to swallow. So I don't think we'll ever get to that point where there's never any more questions to answer.

31:08But I think it's something to strive for because a hypothesis is you'll find that the rest of the sales cycles speeds up. No, I love that. And honestly, the how to increase the sales cycle efficiency is actually a question that I got from somebody I was speaking to at ATD in LA. And so that's perfect. I love that you pulled on that. So my final question for you, and it's actually one of my favorites to ask, is what is your favorite sales win for yourself or your team that you've had in your career thus far? My favorite sales win in my career. Can I give you two? Yes. Okay, so one is going in the way back machine.

31:52Dare I date myself? This was in the early mid 90s. I was still pretty young in my career, but I built a program with others, but I built a program. I was working for Lotus Development Corporation at the time, now owned by IBM, doesn't exist in most people's memories. That was in a channel training program, an authorized training partner program. And in these old days, in our first year, we had$100 million in revenue, which is a long time ago and is a really big number. Yeah, no, that's awesome. And we, the team, there were five of us, but I was the manager of the team. We won a company-wide award.

32:36It was probably the first company-wide award that I won. And it was across, you know, company recognition and it just felt good. And I think I still have the Crystal Award somewhere in my house going way back then. At the time, Lotus was a relatively small company, about 2 ,000 employees. And people knew you and they knew your story and it just felt really, really good and really accomplished. So that's a big win that unfortunately is in the Wayback Machine. And something more current is last year we did a company narrative reboot and we did it at starting at the executive level. So working with our marketing and product team, we built the story over, we kind of worked through what that needed to sound like.

33:27And starting with the CEO, we did a one-on-one recording of each executive giving the pitch. And we did it on kind of our first level executives and then our second, all the VPs. So at the time, there was maybe 12 or 15 people that went through it. And I put together a whole training program for them, a couple of recordings of what could look like. And then we scheduled them. I was participated in every single one with the CEO. We gave live feedback. We gave everyone their recording and asked them to give feedback themselves. So it was a really great win of alignment across the whole company to make sure that everyone, whether you were in finance, product, marketing, you know, sales across the whole organization, you kind of knew who we were and what we did.

34:18That's awesome. Congratulations. And I love that you and the CEO both put yourselves into it. And that's, again, another example of that top down leadership and setting the example to help generate the buy in and start finding those champions. And that's great. Well, congratulations on both of those wins. Thank you so much for joining us on the Sales Gravy podcast. And we really, truly appreciate the partnership with Thought Industries. You help us deliver the highest quality sales education on the market. and we love doing what we do every day and we appreciate that you guys help us get it done.

34:52Thank you again for joining me. Thank you, what a pleasure.