Ep. 176 The Art of the Ask: 10 Questions That Open Doors
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Josh Lupresto (00:01)
Welcome to the podcast designed to fuel your success selling technology solutions. I’m your host, Josh Lupresto SVP of sales engineering at Telarus and this is next level biz tech.
Everybody welcome back. We’ve got a totally different episode for you today. We’re trying out, see if you like it. Today we’re just talking about, it’s just me, it’s just you and I talking. And we’re talking about the art of the ask: 10 questions that open doors. So, you know, we get asked a lot, speaking of getting asked, hey, we learned this great technology. We saw this great thing from one of the Teleris vendors, but how do we then go and apply that? Or how do we open the door?
that gets us into that. And so today that’s what we want to talk about with this, the art of the ask and the 10 questions to open these doors, you know, across different swim lanes. Some of these are specific to a certain tech stack. Some of them are just very general. So we’ll go through these 10. We’ll talk a little bit about what each of them means and maybe how you apply it, a little bit of situation. And if you like it, give us some feedback, share, you know, reach out to us directly, put some comments in there.
Would you like to see more something specific, vertical, anything like that, any way we can help you. We want to keep bringing great content like this to you that makes sense. So question number one, how are you currently using AI or automation in your day to day operation? So let’s imagine you’ve teed this up, you’re at lunch with the customer, the prospect, you’ve sat down and we’re just trying to ease in to the AI.
And I think when you ask a question like this, it starts to establish their baseline and it just reveals whether they’re experimenting or not. Maybe they’re fully adopting, maybe they’re ignoring AI altogether. I think it lets you gauge some of this digital maturity and really see if there’s any low hanging fruit, right? Because of course we’ve got vendors that help with all different components of all the things that we’re going to talk about today, but it lets you understand where they are right now.
And so each of these questions, you can kind of imagine what your own step of pushing into the next layer and the next layer. But if we’re asking if they have, and it’s a yes, then it’s a, cool. Where are you using it? cool. How is that working? If it’s a no, well, have you thought about it? Have you thought about optimizing in any specific areas yet? Tell me about some of the pain points you have in some of the areas where you had.
you know, these repeated manual processes and things like that. So you can kind of start to see with each of these questions, we’ll do a little bit of, you know, the engineering nerd, right? Wants me to do it if then, so we’re going try to make it if then as cool as it can be and as conversational as possible. Question number two, what is the biggest bottleneck or manual process that your teams still struggle with? So we like this question because, you know, AI and automation themselves specifically, they’re about eliminating friction.
So this really starts to kind of surface up things that are ripe for workflow transformation and a great area for recommending new technology. I I think what you see out of lot of these businesses is they keep doing the same old things over and over again. nobody’s really questioning, are we doing this? Should we be doing this? And so understand the business a little bit, understand what some of their products are.
and maybe frame that question specifically towards one of their products or how they sell one of their products or how they support one of their own products. And what are some of the manual processes? I like an example about this is we used to talk about with mobility and IOT. And you think about, how do I go into a healthcare organization and how do I help them understand, right? We’ve got these box of Legos in the mobility and IOT space, but people can’t quite, they don’t know what’s possible. And I think that’s what a lot of this is about. We have to…
give them ideas specific to their world and their ecosystem as to what’s possible. think about healthcare. Maybe I’m walking in and I, know, what kind of things are you doing manually right now? ⁓ well, we walk into this area, we check something on a clipboard, we check and see how many beds we have in here, or we check and see, you know, what these patients are doing and where they’re going, and then we enter that in. Well, what if that could be done automatically? Or what if that could be done without you having to engage in it manually? Maybe it’s just
UQAing the automation and seeing if those things are working. here, they will be happy to talk about the things that they are frustrated with. And they’re not always correlating, you know, what could be done, how it could be better. And so I think that’s the beauty of where you all come in is helping understand where it could be better. Number three, what customer experience touch points?
Do you wish were smarter or more responsive? So this is imagine their customers, their clients reaching out to them. So what this does is it connects the idea of AI to revenue and to satisfaction and things like that. So if they start to say, you know, gosh, we’ve got slow response in some areas, we’ve got inconsistent service in some areas, that’s certainly, that’s an immediate wedge in for an AI powered.
CX conversation and not everything here is going to be about AI, right? But I want you to be thinking about what they’re probably thinking about, which is I’m being asked or told, that’s going to be one of the questions that we talk about in a little bit. How do I navigate that? just think specifically about, ⁓ do some homework on them. Again, like we used to talk about, if you’re door knocking and you’re working with these customers, look at the phone that’s on the other side of the desk.
That experience is different now. Go to the website, go to a chat, buy a product, try to return it, see what that experience is like. Because sometimes they don’t even know. They put the technology in place and maybe somebody else put it in place historically, but they don’t know what that experience is like. But if you’ve done that diligence to say, hey, you know what, I actually went through and noticed some inconsistencies. Do you notice any inconsistencies or do you have any customers complaining or what are your CSAT scores?
saying or you know, what are some of these surveys saying? ⁓ Maybe that’s an area that you can help in. Number four, do you feel that current vendors or tech stacks that you have are keeping up with the latest innovations? ⁓ This one goes a lot of places. This one, I think it really prompts this idea of ⁓ reflecting on vendor lock-in or maybe just some legacy fatigue. And honestly, if they’re not sure,
the question might be, I don’t know. Then maybe it’s an opportunity to help them benchmark, to understand what other people are doing, what other industries are doing. Because if they’re being tasked to go modernize and go do some things, what kind of tech stack, what kind of tech debt do they have that they’re relegated to? And again, I think sometimes when people are stuck in that tech debt space, they don’t know what else is out there. They haven’t prototyped, they haven’t played around, they haven’t experimented.
Meanwhile, you all have, we have, we understand these landscape of the vendors that there is exposure to. So ⁓ have an understanding of what their tech stack is. And I think it’s super helpful when you hear that tech stack and we’ll listen for key words. We might hear, yeah, you know, we’ve got this great tech stack and we’ve got this AS400 and you should hear, my gosh, AS400, right? That technology was out of date 15 years ago. That’s old IBM iSeries.
we can help modernize that this way, this way, this way, you know, those types of things. so get some exposure, collect some information, understand what part of the tech stack they have and what are they locked into and maybe what are they not locked into? What’s expiring soon? You might learn some things like that along the way as well. Number five, what concerns do you have around data privacy, compliance or security as you’re trying to adopt these new tools? You know, you’ve certainly got
some of these thoughts around, know, oh, we want to go down the road on AI. And maybe that raises some data, some trust, some governance worries. That’s great for the opportunity. I think this surfaces the blockers that you can help them solve, or maybe some competitive advantages around vendors that are a little more security first. so AI governance, I mean, we looked at this, we’ve seen some Gartner studies on this. If you’ve been to recent Tillerus events, know, 10, 15 % of people
barely from a business perspective have any sort of AI governance policy at all. So we don’t want to get down the road of ⁓ thinking about governance too late. We’ve got to think about it early. We’ve got to think about it often ⁓ and ahead of time. ⁓ question number six. Are you experiencing any pressures from leadership to do more with less or become more efficient? This is a hot one right now. So you think about
⁓ economic pressure, things like that that are going on, you know, the broader macro economic trends, that drives transformation. So if you ask this, are you experiencing pressure? And that answer is a yes. I think that naturally leads to an ROI based AI automation, just a pure tech stack ⁓ replacement conversation. So flush that out. know, look, the channel, that’s what I love about the channel, it’s so resilient.
Sometimes we’re transforming, sometimes we’re doing cost savings, sometimes we’re doing automation, and sometimes it’s a combination of all three of those. And so let’s understand where they are and what their leadership is expecting them to do. Because there isn’t always a correlation, Leadership might have heard about this one great tool or this one great thing and expect that it’s easy, just go implement it, right? And you’re talking to, you know, Timmy or Susie in IT that’s a team of one, and they’re being expected to kind of roll out and implement the solution that they find out.
needs a lot more help of which you can help with. So I love, this is a hot topic right now. A lot of people having this conversation of how do I transform? How do I wedge in this new service without full rip and replace? So a lot of talk track around that. Number seven, how do you evaluate whether this AI feature is just hype or it’s truly valuable for your business? This is an honest question for you.
to kind of understand how they do evaluation and what the psyche of the person that you’re talking to is, right? It might be very eye-opening. You might realize, wow, they’re barely evaluating any of this. Or you might realize, whoa, they’re really being thoughtful in this. This person is deep down the road. There’s some buy-in here. With things like this, though, feels like there is a lot of kind AI washing out there. And so this helps you educate them.
Position yourself as this trusted advisor who just helps cut through the noise. Number eight, have you had any recent incidents, outages, security scares, compliance audits, things like that that just maybe exposed some gaps in your current setup? And what more motivating than change that we’ve seen historically in the past than pain? So look, if they mention any events, you could pivot to some of these more
⁓ concrete solutions, we can talk security, we can talk backup, we can talk ⁓ resilience. Because if you don’t, I think if you don’t ask this question about recent security incidents, recent concerns, recent things, they’re not always gonna volunteer that information. So don’t be afraid to ask that question, listen and understand, hey, you had a scare, what was it? Did you find out what the cause of it was? Have you remedied, are you sure that it won’t happen again?
unearth that a little bit. We’ve had some really great conversations with those again, where people thought they were on their own, they were afraid to talk about it. And we would rather them ⁓ figure out how to mitigate that for future and be prepared for future than just go, I hope it’s, I hope it’s good. Hope is not a strategy. Number nine, as we get here, ⁓ kind of towards the back half of this, what is on your roadmap, your technology roadmap for the next?
12 to 24 months, any big changes coming up. So this, I think what this does, and these roadmaps are dynamic right now, they’re very fluid with all the different tech, all the different AI, all the different productization coming out, but I think this helps align your recommendations with their strategy, the budget cycles, the change windows, but I think sometimes out of this, what you see is you find some immediate wins, maybe you find a quick win, but this is really about
positioning you as the long term partnership, right? Looking out much further, 12, 24 plus, because some of these transformations just take a significant amount of time, right? A lot of us have been in these roles, we’ve done these migrations, we’ve seen the pain that comes from it. look, I’m convinced, you know, we’re not defined by some of the things that we do quickly, we’re defined by how we help people handle
and deal with during the paint, during the migrations, how we’re down in the trenches with them. And so this really helps, I think, position you as the expert and the true advisor as you go through some of that.
Last but not least, number 10. Now know this sounds silly. Don’t laugh at me when you hear this, but I think people need to be asked these questions a weird way sometimes to get thought provoking ideas out. So number 10 is if you could just wave this magic wand and fix one thing about your customer experience, your tech stack, ⁓ your IT team, insert whatever makes the most sense there.
What would it be? This look, this is a fun one because it gets them to dream big, not talk emotionally, know, and sorry, and talk emotionally, not just rationally, right? Sometimes their wish points to solutions they didn’t even know existed. We’ve seen this time and time again. They have this requirements list and then they have these wish lists like, my gosh, if we could do these things, that would be crazy. Not thinking that they could even do those.
And here we are, you are, you come back into this equation and it’s, yeah, we can do that. And we’ve done that four times already this month. And they go, ⁓ my gosh. Okay. So you become this kind of heroic problem solver that they didn’t even know was a thing. So understand, I like that because maybe you’ve come in and you’ve sold them this one product or this other product, and they’re just not thinking that you can help with this crazy thing over here. Maybe they don’t want to put that on your radar. Maybe they, maybe they
thought that they had to figure that out themselves. And so I like that because just again, the things that we have, we’ve got hundreds of vendors, hundreds of OEMs with those respective vendors. There’s a lot of things that are possible, right? Love playing with Legos, but sometimes people don’t always know what to build and we’ve got to help them guide through that. So remember, you know, as the complexity prevails, you all add
tons and tons of more value. And again, the customers need you now more than ever, because that’s what we’re getting. We’re AI products on this feed, that feed, the next great thing, and we’ve got to help them all decide, is it vaporware? Is it real? Does it help drive ROI in their business? Get a product out to market faster? Does it help the bottom line? All those things. So again, ⁓ final thoughts here, I guess. Try your best to mix these into a natural conversation. I know I’m being very like,
bang, bang, matter of fact. But you want to mix these into natural conversation. You’re not trying to do this interrogation technique. You just really want to spark ⁓ curiosity. And you want to get customers thinking about gaps that they hadn’t considered. I think sometimes this is a seed planning exercise. Maybe you’re going to get some immediate, but if anything, you’re going to
have a reason to engage with them three months later, six months later, because maybe you’re going to find out, they’re going to be working on this other thing. So you’re going to help them, I think, with some things that they hadn’t considered yet. So with all these, don’t forget, you’re not alone. You’ve got a team of resources here at Tolaris that are here to help you on our sales engineering team. You’ve got our advanced solutions team. Look, there’s a lot of people that want to help you with these. And as you go down the road,
and you start to ask some of these questions. Remember, if you need to pull the rip cord, the question is, hey, you know what? That’s great. You’ve answered yes to one of these. You’ve got an initiative. You’ve got a thing. Are you open if I just bring in some additional technical resources to help flush out some of those requirements? Can we set that up? Can we get a conversation on the book, schedule a Zoom, whatever it might be? And often you’re going to find that the answer to that is a yes. And for every one thing that you think we might talk about, we end up talking about.
Three or four more. So, that wraps us up for today. Banging through, you know, 10 key questions, the art of the ask, questions that opened some of these doors. Hopefully that was helpful. Listen, I would love your feedback on these. Would you like to see more things like this? Again, more specifically, more generally, any different level. Leave us some comments, shoot me a note, reach out to me. Would love to hear what is the most helpful for you as an advisor.
to grow your business. until next time, that wraps us up for today. I’m your host, Josh Lupresto SVP of sales engineering at Telarus. This has been the art of the ask, 10 questions that open doors. Thanks everybody.