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July 2, 2025 • 18 mins

In this 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 altogether.

(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 rightfor 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 is 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 orwe 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

(04:21):
automatically? Or what if that could be done
without you having to engage in it manually?
And 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 know, what, what could be done,

(04:43):
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 we're smarter or more
responsive? So this is imagine their
customers, their clients reaching out to them.

(05:04):
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 some
areas, that's certainly that's an immediate wedge in for an AI
powered CX conversation. And not everything here is going

(05:26):
to 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 about
do some homework on them. Again, like we used to talk
about, look, if you're, if you're door knocking and you're

(05:46):
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 place
and maybe somebody else put it in place historically, but they
don't know what that experience is like.

(06:07):
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 sayingor, 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 current vendors or tech stacks

(06:30):
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,then maybe it's an opportunity

(06:53):
to help them benchmark to understand what other people are
doing, what other industries aredoing.
Because if they're, you know, ifthey're being tasked to go
modernizing, 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 knowwhat else is out there.

(07:14):
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, you know, there is exposure to.
So have an understanding of whattheir tech stack is.
And, and I think it's, it's super helpful when you hear that
tech stack. And we'll listen for keywords.

(07:35):
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, understand what part of the tech

(07:56):
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 likethat along the way as well #5
what concerns do you have arounddata privacy, compliance or
security as you're trying to adopt these new tools that, you
know, you've certainly got some of these thoughts around, you

(08:17):
know, oh, we want to go down theroad 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 looked at this, we've seen some

(08:40):
Gartner studies on this. If you've been to recent
tilarious events, 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 theroad 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. Now, question number six, are

(09:03):
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. So if you ask this, are you

(09:24):
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. You know, look the, the, the
channel. So I love about the channel.
It's so resilient. Sometimes we're transforming,

(09:44):
sometimes we're doing cost saving, sometimes we're doing
automation, and sometimes it's acombination 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 acorrelation, 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? And, and you're talking to, you

(10:06):
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

(10:26):
RIP and replace. 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

(10:46):
the, 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, theyare, 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 a
lot of kind of AI washing out there.

(11:07):
And so this, this helps you educate them, position yourself
as this trusted advisor who justhelps 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 than change that we've seen

(11:31):
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 if
you don't ask this question about recent security incidents,

(11:51):
recent concerns, recent things, 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,

(12:12):
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.
Then just go. I, I hope it's, I hope it's Good
Hope 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

(12:33):
technology road map for the next12 to, to 24 months?
Any big changes coming up? So this, I, I, I think what this
does 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, the

(12:56):
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,

(13:17):
right? 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 deal
with during the pain during the migrations, how we're down in
the trenches with them. And so this really helps, I

(13:39):
think position you as the expertand 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. So #10 is if you could just wave

(14:03):
this, you know, wave this magic wand and fix one thing about
your customer experience, your tax 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 big.
Not, not not talk emotionally, you know, and, and I'm sorry and

(14:26):
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, not thinking
that they could even do those. And here we are.
You are, you come back into thisequation and it's yeah, we can

(14:48):
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
product or this other product and they're just not thinking

(15:08):
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.
There's a lot of things that arepossible, right?

(15:28):
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
this feed that feed the next great thing.

(15:50):
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.
I know I'm being very like Bang Bang, bang, matter of fact, but

(16:12):
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
immediates, but you know, if if anything, you're going to have a

(16:34):
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 are help
you, that are here to help you on our, our, our sales

(16:55):
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.
Are you open if I just bring in some additional technical

(17:17):
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 it 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 at 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 Polaris Studio 19.Please visit telaris.com For
more information.
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