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September 10, 2025 • 18 mins

In this revisited episode, Josh Lupresto discusses the art of asking the right questions to open doors in technology sales. He outlines ten key questions that can help sales professionals engage with clients, understand their needs, and identify opportunities for AI and automation. The conversation encompasses various themes, including the current application of AI, identifying bottlenecks, enhancing the customer experience, evaluating vendor technology, addressing data privacy concerns, and planning for future technology roadmaps. Josh emphasizes the importance of building relationships and being a trusted advisor to clients.

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Episode Transcript

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(00:01):
Welcome to the podcast designed to fuel your success selling
technology solutions. I'm your host, Josh Lopresto,
SVP of Sales Engineering at Telaris, and this is Next Level
Biz 10. Everybody, welcome back.
We've got a totally different episode for you today.
We're trying out see if you likeit.

(00:22):
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.
You know, we get asked a lot. Speaking of getting asked, hey,
we, we learned this great technology, we saw this great
thing from one of the Polaris vendors.
But how do we then go and, and, and apply that or how do we open

(00:43):
the door that that gets us into that?
And so today that's what we wantto 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 aren't 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

(01:05):
bit of situation. And if you like it, give us some
feedback here, 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 #1 how are you currently using AI or automation

(01:27):
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 you've sat down and we're just
trying to ease in to the AI. And I think when you, 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 all together.

(01:49):
I think it, it lets you gauge some of this, you know, digital
maturity and really see if there's any low hanging fruit,
right? Because of course, we've got
vendors that that help with all different components of all the
things that we're going to talk about today.
But it lets you understand wherethey 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

(02:10):
layer. But if we're asking if they have
and it's a yes, then it's a oh, cool, where are you using it?
Oh cool, how is that working if it's a no?
Well, have you thought about it?Have you thought about
optimizing in any specific areasyet?
Tell me about some of the pain points you have in some of the
areas where you had, you know, these repeated manual processes

(02:33):
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 to try to make an
if then as cool as it can be andit's conversational as possible.
Question #2 what is the biggest bottleneck or manual process
that your teams still struggle with?

(02:53):
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 mean, I think what you see outa lot of these businesses is
they keep doing the same old things over and over again and

(03:17):
they nobody's really questioningwhy are we doing this?
Should we be doing this? And so understand the business a
little bit, understand what someof their products are and maybe
frame that, 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, the, the manual processes?

(03:38):
I, I like an example about this as we used to talk about with
mobility and IoT and you, you think about, well, 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,
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

(03:58):
specific to their, their world and their ecosystem as to what's
possible. So think about healthcare.
Maybe I'm walking in and I, you know, what kind of things are
you doing manually right now? Oh, well, we walk into this
area, we, 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,

(04:20):
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 you QA ING the
automation and seeing if those things are working.
So here they will be happy to talk about the things that they
are frustrated with and they're not always correlating, you

(04:40):
know, what, what could be done, how it could be better.
And so I think that's the, that's the beauty of where you
all come in is helping understand where it could be
better #3 what customer experience touch points do you
wish were smarter or more responsive?
So this is imagine their customers, their clients

(05:03):
reaching out to them. So what this does is it, 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 someareas, that's certainly that's
an immediate wedge in for an AI powered CX conversation.

(05:25):
And not everything here is goingto be about AI, right.
But 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 talked about
in a little bit. How do I navigate that?
So just think specifically aboutdo some homework on them.
Again, like we used to talk about, look, if you're, if

(05:45):
you're door knocking and you're and you're working with these
customers, look at the phone that's on the other side of the
desk. You know, 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 placeand maybe somebody else put it
in place historically, but they don't know what that experience

(06:06):
is like. But if you've done that
diligence to say, hey, you know what, I actually actually went
through and, and noticed some inconsistencies.
Do you notice any inconsistencies or do you have
any customers complaining or what are your CSAT scores saying
or, or you know, what are some of these surveys saying?
Maybe that's an area that you can help in #4 do you feel that

(06:28):
current vendors or tech stacks that you have are keeping up
with the latest innovations? This, 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, if
they're not sure, the the question might be, I don't know,

(06:51):
then maybe it's an opportunity to help them benchmark to
understand what other people aredoing, what other industries are
doing. Because if they're, you know, if
they're being tasked to go modernize and go do some things,
well, 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

(07:13):
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 that, that, that, you know,
there is exposure to. So have an understanding of what
their tech stack is. And, and I think it's, it's
super helpful when you hear thattech stack and we'll listen for

(07:34):
keywords. We might hear, Oh yeah, you
know, we've got this great tech stack and we've got this AS 400
and you should hear, my gosh, AS400, right, that that
technology was out of date 15 years ago.
That's old IBM I series. We can help modernize that this
way, this way, this way, you know, those types of things.
And so get some exposure, collect some information,

(07:55):
understand what part of the techstack they have and what are
they locked into, and maybe whatare they not locked into?
What's expiring soon? You might learn some things like
that along the way as well #5 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

(08:16):
some of these thoughts around, you know, oh, we want to go down
the road on AI that maybe that raises some data, some trust,
some governance worries. That's great for the
opportunity. I think this surface is 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

(08:39):
looked at this, we've seen some Gartner studies on this.
If you've been to recent Telarisevents, you know 1015% 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.

(09:00):
Now, 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 macroeconomic trends that drives transformation.

(09:22):
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, justa pure tech stack replacement
conversation. So flush that out.
You know, look the, the, the channel.
So I love about the channel. It's so resilient.

(09:43):
Sometimes we're transforming, sometimes we're doing cost
saving, 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, right? The 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?

(10:05):
And, and you're talking to, you know, Timmy or Susie in IT.
That's a team of 1. 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, you know, full RIP and replace.

(10:27):
So a lot of talk track around that #7 how do you evaluate
whether this AI feature is just hype or it's truly valuable for
your business? This is a, this is an honest
question for you to kind of understand how they do
evaluation and, and what, what the, what the psyche of the

(10:48):
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
are, they're really being thoughtful in this.
This person is deep down the road.
There's some buy in here, you know, with things like this
though, it feels like there is alot of kind of AI washing out
there. And so this, this helps you

(11:08):
educate them, position yourself as this trusted advisor who just
helps cut through the noise #8 have you had any recent
incidents, outages, security scares, compliance audits,
things like that, that just maybe expose some gaps in your
current setup? And what, what more motivating

(11:29):
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, you know,
concrete solutions. We can talk security, we can
talk backup, we can talk resilience.
Because if you don't, I think ifyou don't ask this question
about recent security incidents,recent concerns, recent things,

(11:53):
they're not always going to volunteer that information.
So don't be afraid to ask that question.
Listen and understand. Hey, you, you had a scare.
What was it? Did you find out what the cause
of it was? Have you remedied?
Are you 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

(12:15):
it. And we would rather them figure
out how to mitigate that for future and be prepared for
future. Then just go.
I, I hope it's, I hope it's GoodHope is not a strategy #9 as we
get here kind of towards the, the back half of this, what is
on your road map, your technology road map for the next

(12:35):
12 to, to 24 months? Any big changes coming up?
So this, I, I, I think what thisdoes and, and you know, these
Rd. maps are, 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, thechange windows.

(12:57):
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 positioningyou 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?

(13:18):
A lot of us have been in these roles.
We've done these migrations, we've seen the pain that comes
from it. And look, I'm, I'm convinced,
you know, we're, we're not defined by some of the things
that we do quickly. We're defined of how we help
people handle and, and, and dealwith during the pain during the
migrations, how we're down in the trenches with them.

(13:38):
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 #10 now I know this sounds silly.
Don't, don't laugh at me when when you hear this.
But I think people need to be asked these questions a weird
way sometimes to get thought provoking ideas out.

(14:01):
So #10 is if you could just wavethis, you know, wave this magic
wand and fix one thing about your customer experience, your
tech stack, your IT team, how you know insert whatever makes
the most sense there. What would it be?
This look, this is a fun one because it gets them to dream

(14:21):
big, not not not talk emotionally, you know, and and
I'm 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 they have this requirements list and then they
have these wish lists like, Oh my gosh, if we could do these
things, that would be crazy, notthinking that they could even do

(14:43):
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, oh, oh, my gosh.
OK, so you become this kind of heroic problem solver that they
didn't even know was a thing. So understand, I, I like that
because maybe you've come in andyou've sold them this one

(15:05):
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, I, I like that because
we just, again, the things that we have, we've got hundreds of
vendors, hundreds of OEMs with those respective vendors.

(15:26):
There's a lot of things that arepossible, 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, as
the complexity prevails, you alladd 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 getting AI products on

(15:48):
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, the bottom line, all those things.
So again, final thoughts here. I guess, you know, try your best
to, to mix these into a natural conversation.

(16:09):
I know I'm being very like Bang Bang, bang, matter of fact, but
but you know, you're, you want to mix these in a natural
conversation. You're not trying to do this,
you know, interrogation technique.
You just really want, you want to spark curiosity and you want
to get customers thinking about gaps that they hadn't
considered. And I think sometimes this is a
seed planning exercise. Maybe you're going to get some

(16:31):
immediates, but you know, if if anything, you're going to have a
reason to engage with them threemonths later, six months later,
because maybe you're going to find out, oh, they're going to
be working on this other thing. So you're going to help them, I
think with some things that theyhadn't considered yet.
So with all these, don't forget you're not alone.
You've got a team of resources here at Telaris that'll help

(16:53):
you, that are here to help you on our, our, our sales
engineering team. You've got our advanced
solutions team. Look, there's a lot of people
that, that want to help you withthese.
And as you go down the road and you start to ask some of these
questions, remember, if you needto 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'vegot a thing.

(17:14):
Are you open if I just bring in some additional technical
resources to help flush out someof those requirements?
Can we set that up? Can we, you know, get a
conversation on the books, the schedule, a Zoom, whatever it
might be? 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.

(17:37):
Banging through, you know, 10 key questions, the art of the
ask questions that opened some of these doors.
So 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 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

(18:01):
advisor to grow your business. So until next time, that wraps
us up for today. I'm your host, Josh Lopresto,
SVP of Sales Engineering and Solaris.
This has been the art of the Ask10 questions that open Doors.
Thanks everybody. Next Level Biztech has been a

(18:22):
production of Telaris Studio 19.Please visit telaris.com For
more information.
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