#470 - How Top Sales Reps Handle Objections Before They Even Happen | Bryan Charlton
from 30 Minutes to President's Club | No-Nonsense Sales
37m 31s
This transcript emphasizes transformative sales strategies rooted in human-centered conversations and proactive deal risk management. Sam McKenna demonstrates how using network data and warm introductions can bypass cold outreach resistance, while Brian Charlton outlines a structured approach to de-risking deals through scenario planning, stakeholder alignment, and discovery-driven conversations. Key principles include preparing for best, alternative, and worst-case outcomes, controlling the call’s opening with client-aligned questions, and deeply understanding the business story through multi-layered stakeholder engagement. The discovery process is not just about identifying problems but uncovering the internal narrative—securing champions, gaining VP-level buy-in, and validating user adoption. A recurring theme is the importance of post-signature planning, where 30-60-90 day plans build trust and ensure successful onboarding. The episode also highlights a critical sales habit: treating inbound leads as opportunities to explore, ask questions, and uncover hidden organizational pain points. Ultimately, success comes not from pushing a pitch, but from building trust, understanding the business context, and involving the right people across departments to make the solution both credible and adoptable.
Sellers cold outbound socks for both you and your prospect.
It takes an insane amount of effort, repliates her in the tank, and you are fishing in the
same pond as everybody else.
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she built her business from scratch into a multi-million dollar business using exactly what
she teaches in her social-selling course that she built in partnership with 30MPC.
Go to 30MPC.com/Sam, and her new course teaches you how to use relationship data and
your network's network to get warm introductions into your dream accounts that would never
answer your cold call, respond to your cold email, or open the gift that you sent to
their office.
If you go to 30MPC.com/Sam, we are giving away all of Sam's favorite LinkedIn sales
net reports, alerts, and scripts that you can use to break into more accounts with less
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Objections happen.
Don't flinch at objections.
As you want to figure out, is this a brick wall or something we can get around?
Is it just a knowledge gap?
Or is there just perhaps something that the client hasn't shared yet?
Hey, my CRO hasn't actually been able to look at this particular stuff.
I might bring that up and say, you mentioned that these were kind of key things to the business.
This is what was flowing downstream by not having that.
What's changed?
Is this no longer a priority for that person?
We'd love to understand kind of what's going on.
If we haven't established value enough in a way that resonates, that's okay.
We can take a step back and figure out how to show that.
I'm not concerned about that.
I'd love to hear more from you.
When people share a concern, they're expecting to put the blast wall up.
They got their finger on that waiting fruit to go up.
And when you ask a question and speak to understand, they kind of take their finger off the blast wall.
They start sharing and then when you do respond, they're less likely to throw up the blast wall
and you can actually have a real positive human conversation and hopefully get somewhere.
Good morning, everybody and welcome to this episode of 30 Minutes to President's Club.
My name is Armon Froke and I'm here with my co-host Nick Skelsky and folks today we have
a man who's been leading sales organizations for over 12 years.
It's a Hollywood intro.
I believe just crossed a stupidly large error while stone over $100 million an hour.
And Brian is one of their top sales leaders.
And this is a badass episode on de-risking deals.
Nick, why should people listen?
Yeah, we actually covered a lot of ground in this episode.
We got everything to an approach to anchoring your customer in a headspace at the beginning
of your calls.
We talked about a bunch of different deal detractors or things that expose risk in your
deal and ways that Brian and his team specifically mitigate those and address them.
We talked about this concept around scenario game planning to help you show up to your
calls way more prepared.
We got into like some tactics he even uses to get CS to help him nudge his deals to close.
And so this was a we have we we literally covered pretty much every stage of a deal cycle
and ways that you can shore up your pipeline in three, two, one.
Let's roll.
All right, Brian.
Welcome to the show.
I'm going to call this game plan your outcome.
So let me share an example from a call I had this morning with one of my reps at 7 a.m.
We're meeting with a director of sales who's been evaluating our product.
And the first tip is to go into the conversation with an understanding, even write it down,
of what your best case outcome could be, the next best alternative, and potentially
the worst case that could come up.
And let me even example the call this morning.
We obviously sell it.
And we sell a conversation intelligence tool I'm working with a sales leader in this case.
We know that the CRO needs to green light the project.
They haven't been directly involved part of what we've been doing is trying to kind of convince
this level of folks to get them involved and get some information up.
So best case would be, hey, based on the results that we've generated, I actually talked
to my CRO yesterday.
They love it.
They're absolutely on board.
We have their support to move forward.
Let's start to talk details about how we get this thing launched and practically implement
it.
Fantastic.
What's another alternative?
Maybe it's, hey, we have evaluated things.
We've got some good data.
Haven't talked to that person yet.
There's a couple of things that we think are gaps we need to address.
I'm not sure how we'll tell them about this and this and this.
These are objections we're expecting that we haven't prepared for.
That's okay.
We can work through that together.
So that's an alternative I might prepare for.
Maybe worst case is either that something's come up and that's no longer a priority.
Or maybe they tell me that their CRO is maybe looking at an alternative solution or something
like that.
So I want to think about that scenario as well.
Well, let's take us to the next scenario, which is tip number two.
Tip number two is I think about controlling the start of the conversation, right?
So I like to take control of the call by opening by recapping a couple of things that the
client shared early on that are goals, objectives, and ways that we've proven so far, hopefully
in their own words or their teams words, that we're bringing some value or meeting a particular
need.
Let me share an example from the conversation this morning.
It's director of sales.
We knew that starting out, they really cared about helping their reps take and gather information
more efficiently from their calls and getting into CRM and moving it through their workflow.
Two, creating coachable moments for their leadership.
They're fast growing, they've got large sales teams.
They're trying to coach at scale, and they want it a way to provide high value coaching
to their teams.
And the third thing is to create that visibility layer for the executives to understand what's
happening on a macro scale in the business.
Where are we winning deals?
Where are we losing deals?
What are some trends that we're seeing out there in the market potentially before they
show up in the win-loss column?
And so I like to start the call up by saying, hey, thanks for meeting with us today.
When we met, kick this off initially, you would share that these were your kind of two or
three things you wanted to solve for.
And over the course of working with your team, we have heard A, B, and C that supports
where meeting those things.
I'd love to hear today from you about where you feel like you're seeing this solution
match up with those areas.
And then we can talk about what this potentially means and how we can work together.
If you are sick of non-actual takes about AI and sales, you might be interested in attending
my live session at Apollo next on September 30th in San Francisco.
Come and join if you want to join actionable sessions with teams like yours.
If you want first looks at Apollo's biggest launches and if you want to network with operators
who are talking action, not academia, I promise that you were going to walk away with stuff
that you can put into action right away and you can register for free.
If you use our 30MPC link or code in the show notes, I will see you there.
Today's show was brought to you by Pipetrives easy to use and customizable CRM with built-in
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My favorite discovery question is the multiple choice question, which sounds like typically
when I'm talking with folks like you, they're focused on A, B or C, which is it for you.
Now A, B and C have to be problems that you can solve because that's how you steer the
conversation in the direction of places you can help them.
Now Pipetrives built-in meeting intelligence helps you focus on your follow-up question,
not on scrambling to take live notes and we built a full discovery toolkit with them
free in the 30MPC Closers hub.
There's a link in the show notes.
All right, Brian, round us out with number three, the last thing objections happen.
When it comes up, the first thing I suggest people do is you want to figure out, is this
a brick wall or something we can get around?
So in this instance, maybe what they share with me is like, hey, my CRO hasn't actually
been able to look at this particular stuff.
I haven't been able to get their attention on this solution.
I might go back and use what I learned early on about why we're doing this in the first
place, because hopefully you tested and made sure that there were some real reasons for
going down this evaluation.
What's changed?
Have they found a different way to solve it?
Would love to understand kind of what's going on.
Then maybe there's ways we can help establish.
I'd love to hear more from you and get them to share a bit more.
I think asking a question as opposed to offering a solution is really, really important.
When people share a concern, they're expecting, I like to call it like the blast walls.
They're expecting to put the blast wall up.
When you ask a question and seek to understand, they take their finger off the blast wall.
They start sharing.
When you do respond, they're less likely to throw up the blast wall and you can actually
have a real positive human conversation and hopefully get somewhere.
In the prep, we talked about the seven deadly deal gaps.
We're going to go through the deal gaps, one, I don't know if it's seven, but we'll figure
out how many of this.
We're going to go through deal gap by deal gap because you talked about planning for the
best case, best alternative and worst case, and a lot of times we're ignoring the worst
case in our deal.
The first one that I want to go through is you talked about a really common risk where
you feel like reps can't tell the unique story to the business.
I'm curious if you could expand a little bit on what that means.
Here's an example of a scenario is that you meet with somebody and maybe during the discovery
call, they share a couple of things that you know are important that your solution can
solve.
What I want my reps to be able to do at that point is restrain their excitement.
It's natural to want to share your knowledge, the more you learn your product, the more you
kind of want to demonstrate that and show competency.
What I want my reps to do is actually ask one or two questions.
Take it a layer deeper.
Say, that's really interesting.
I know you could have picked three or four different things.
How did you pick that?
particular thing to share. And I want to know the story. Where is this coming up? How
did you notice that this was something going on the business? Another question I love
to ask is to affirm it. I'll say, oh, that's really interesting. Or yeah, I can understand
how that'd be important. Who else cares about that? Because getting to be able to expand
this to something that may be more departments, most people in our business is no different.
We want to use the inbound experience that we get or the initial lead that we get. We
want to expand it. And so often you try and expand it kind of like forcefully in like
you're pushing. But I love if I can get people to talk and share about who else cares
about this. Because then when we come back and we say, hey, do you think it would make
sense to educate those people, support them, loop them in. It's really hard for them
to say no, because they've already acknowledged that this is potentially a problem that other
people have in the business. Yeah, that's really good. It makes me think about gosh, back
to episode number one that we had with Joe Caprio, one of the things that he was talking
about was going into a call with a game plan of this specific name of the next person
that you wanted to involve in the sale. But what I really like you're doing there, Brian,
one other way I've heard it phrase before is when somebody shares a problem with you,
you say, oh dang, like I guess I'm curious, is that something just you're dealing with
or are other people being affected by this also? And what that starts to do is one, give
you a sense of like, is this a single person problem? Because you probably don't have
a deal to it there. Or who else might you need to involve deeper in the sale? One place
that I think trips reps up in this area, because I think most people know on the surface great,
somebody tells me something I should be asking one or three or five follow up questions
about it. But a lot of times we'll have buyers show up to the call and they're like, hey,
it's good to meet you. Like the reason that I wanted to meet was we're looking for a conversational
intelligence platform. And I'd love to hear what you all have to offer. And so when somebody
presents that want, how do you recommend that reps reframe things to get that unique story?
Because all they told you there is we want to see I platform what I love to do. I call
it like voice of the customer. So I don't give them my pitch. What I say is, hey, when
I've met with people who are, you know, maybe it's a it's HR recruiting and they're coming
in. They're looking for conversation intelligence around their volume of interviews and what
not. All typically say, hey, when I meet with someone who's in your role, these are three
or four things that they're hoping to solve with a conversation intelligence tool. Where
would you like us to anchor today? And that's where I can get them to start to tell their
story, right? It flips it back and it's sort of like select from the menu what's most important.
And they might say, you know, what all those are most important? I'd say, well, where would
you like to start? You know, pick one. Now we've got a priority. Interesting. Why did you
pick that one? So I think there's ways to do that. And look, to me, it just comes out
of like being human and asking human questions of what happens when, you know, X is going
on in the business, almost get them to like, just think about them telling their story.
Like day in the life, where do you encounter this? Brian, I want to go to the other thing
that you mentioned, which is they're not getting enough people involved in the deal. I'm curious,
could you give an example where this is blown up a deal at order and what people should
do? Like who is the person you were single threaded with? And how did that actually end up
blowing up in the deal? And what should they have done instead? I think there's two forms
of this and you have to be really, really mindful of both. And I think one is far more
tempting to fall into, into reps. And when, when it doesn't work out, they are sometimes
really caught off guard and shocked. The two ways that that works out, I think, is one
is that you have like a, like an IT or a procurement or sort of like a, a profession.
I'm going to call them like a professional buyer. They may not be the end customer, but
they're there as representative on behalf of the company, wanting to buy. And, and, you
know, that's great. We actually want those people involved there. So important to every
single, you know, business partnership to get set up, but you want to make sure that
as you work with those people that you are identifying, I think a couple of things with
that particular persona, I like to give respect of what they need on the call, like to understand
what they're hoping to get out of the call. And I don't try to play coy and resist it.
I want to make sure that I'm going to get them what they need. What I like to do off
front is I like to say, here's how we typically work with clients.
If you are sick of non actionable takes about AI and sales, you might be interested in
attending my live session at Apollo next on September 30th in San Francisco. If you want first looks
at Apollo's biggest launches, and if you want to network with operators who are talking
action, not academia, I promise that you were going to walk away with stuff that you can
put into action right away. And you can register for free. If you use our 30 MPC link or code
in the show notes, I will see you there today. So it was brought to you by pipe drives
easy to use and customizable CRM with built in meeting intelligence. Now, A, B and
C have to be problems that you can solve, because that's how you steer the conversation
in the direction of places you can help them. Now, pipe drives built in meeting intelligence
helps you focus on your follow up question, not on scrambling to take live notes. And
we will take full discovery toolkit with them free in the 30 MPC closures hub. And I will outline if it's somebody like this. I'll say typically
we will meet with someone like you will will make sure we get your initial questions answered.
They might be around these categories of compliance or compatibility or security or
just general control functions. And I'll say, and then what's important is identifying
who's going to be using this, where the values come. And the way that that takes place
is we'll usually set up a follow up demo where we will present to the business users that
you know are looking for this. And we'll educate them and we'll answer their questions
directly. You know, does that sound agreeable? Sometimes they'll say yes, sometimes they'll
say no. If they say no, I think a great thing you can say is I get the, you know, you've
got to make sure that this is the right solution first at the right point. Would you be willing
to introduce us to those people? If you hear yes, now you're thinking great, let me work
with you to understand what is the right point. So I can ask when that trust has been accrued.
If you tell me no, I might pause and challenge and say, I'm going to work with you today,
but this is really concerning because I just in the hundreds of clients I work with, I haven't
had very many situations where, where we haven't gotten these people involved. Could you
tell me more about the hesitation? So there's a lot of ways to handle this that I think again,
you're not trying to be difficult. You're not trying to hold back. You want this person
to walk away feeling a success because they have a job to do too. But you want to establish
that you have a job to do and that you know how this works in your business. And hopefully
you can come together and mutually agree on a way that that makes it a good experience
for both parties.
Yeah, I mean, what you're doing there is really, really smart. It reminds me of we had
Joe McNeil, who is the CRO at InfluToo on and he was talking about like the first step
is you ask to get the other people involved. And then if they say no, you're not going
to be a jerk, especially early on and push, push, push, you're going to say no problem.
What conditions need to be true or where do we need to be for you to feel comfortable
involving those people? And then what you're doing is you're almost yes, anding them.
It's sort of like an improv thing. Arm on, I know you've been doing some improv recently,
but it's they're saying no, we're not going to get them involved yet. And you're saying
great, no problem. Yes, that's how we're going to do things. And when would we involve
them? And that's how you actually go it from being this antagonistic fight to multi thread
to you're just getting the conditions that they need to be true. And if the conditions
that they share are egregious, we need to do 57 demos with you and me. We need pricing
aligned. We need this, this, and this. You're going to come on site and meet with just me
four times. You might decide to opt out and say that seems a little bit extreme. So Brian,
let's go to another deal, wrist that you've talked about. You talked about they never
really talk to the business. Could you unpack that one a little bit more before we dive
into it? Actually, I'll share an example of a project we've got going on right now.
It's with like a midsize tech company that's evaluating us. And we were fortunately able
to get a bunch of different people on to the kind of early demos. And we had someone
from sales, we had someone from product, we had a people from IT, we had people from
their like engineering team. And we started to get like the feedback sessions and the feedback
sessions were kind of lukewarm. I'd say they were like positive, but it didn't give me
the sense that like they want to actually step in and make a change. And we were having
people from engineering give us feedback. We were having people from IT give us feedback.
And then we had the VP of sales join a third session. And that VP of sales came back and
said, Hey, I've been talking to my team behind the scenes. Here's why everybody's a little
bit lukewarm. Here's why I am red hot to make this happen. By the way, this is a priority
for our CEO. This is coming up all over the business. And then they were able to prescribe
like what needs to happen to actually get those people turned around. And so here's here's
where I think that's so important is that the end of the day, you have to have someone
who cares about this particular deal. A way that I asked my reps this in our deal reviews
is if they're working with like a one person and it's a procurement or IT, I like to say
this. I say, Hey, if Jamie got her dream job next week and she left the company, who
would care about honor and pick up this project? And if my rep can't say this business person
and here's why they know instinctively like, Uh oh, I don't know if I have enough people
fighting for this. I don't know if I have enough people.
finding for this. Let's be real about this, right? Priorities come up, budgets are limited,
things shift all the time. We all want our deals to be sticking. The only way that they are is
if you have multiple people who are in it fighting for you. And the people who care the most about
this are the people that your tool serves or your solution serves. So you've got to get the business
involved. You've got to, I want my reps to feel uncomfortable if they're getting further along
and they haven't gotten like the end customer involved. Brian, I actually want to go back to that
conversation that you had with that VP because that's a really interesting scenario where you've
got multiple departments involved. You've got a lot of people who are lukewarm, but you've got someone
who's a really important stakeholder who's like, I'm red hot. This is important to our CEO.
Here's how we win over those other departments. If you use our 30 MPC
link or code in the show notes, I will see you there. Today's show is brought to you by Pipe Drives
easy to use and customizable CRM with built in meeting intelligence. Now, A, B and C have to be problems that you
can solve because that's how you steer the conversation in the direction of places you can help them.
Now, Pipe Drives built in meeting intelligence helps you focus on your follow-up question,
not on scrambling to take live notes, and we will take full discovery toolkit with them free in
the 30 MPC Closers hub. I'm wondering if you can share some of the
questions you asked that VP around how to win over the other departments because this is a common
scenario I see where we've got a coach on the other side and folks don't necessarily know how to
use that coach to help win over other people. I'll share a practical example. I think somebody in
engineering had said to us and to my coach, hey, it feels like this tool is really good for sales,
but I'm not sure if it's as good for engineering. A lot of reps, again, this goes to layering questions.
A lot of reps will want to say, well, no, it is because of A, B, C. What I asked him, as I said,
okay, I said this fair point. Maybe we didn't do our best foot forward in terms of what we
showed them. I said, do they tell you what they would need to see in the solution for it to feel
like it was a good fit for them? What are they wanting? We kind of anchor it on the positive
there as opposed to maybe what's missing. What is it that they want for it to feel like it's for
them? The VP of sales just smiled and he said, you know what? He goes, I asked that exact question.
He wasn't volunteering that information. I think salespeople love to actually sell with other
salespeople to see how they run their deal cycle. I think it's salespeople we want to be led
through a process as well. But, you know, that actually took us into exactly what we needed to
solve for to get this person turned around. Brian, we've talked about risk number one,
which is not being able to tell the story of the business. Risk number two, which is not talking
to enough of the business. I'm curious if we just take a zoom out. I know you've probably coach
hundreds of deals. You also advise companies on coaching and de-risking their deals.
I remember in another episode, KD, Kevin Dorsey, talked about the concept of a strike zone,
which is the area where most deals are won and lost. Yeah. And I'm curious for you,
where do you see as the strike zone of most of your deals? In other words, where's the hot spot in
your deals where the most wins or mistakes are made? And how do I really nail it in the strike zone?
So, I'm going to say this. I think it's two areas. I think you've got two spots where you
have a significant impression on the client. One is that first discovery call. I think the thoughtfulness
of the questions you ask and the kind of steps you prescribe really establish a sense for
whether you as a sales professional are bringing something unique and valuable. I have had people
buy from us who've told me, I've tried a variety of tools. Candidly, I think of writing them
are good. The difference here has been your sales rep because what they did was x with me from
the start. They asked these particular questions. They really sought to understand what I was doing.
They took the time to understand my reasons why they could tell me my story back to me. When I put
them in front of my boss, they were articulate about our business and made me look good. So that
discovery piece, I think, is where I'm going to say that's where you win a lot of trust. And trust
is really critical. And hopefully when you get later in the deal and you need to ask something
from that trust, you have the ability to do it. That would be one key zone. I think the second
zone that comes up and sorry to answer this in a two-parter. But that's just how I'm thinking about
this is I think the second piece is leaving like a key role out of a deal. And here's what I mean.
We've talked about power and a decision maker. We've talked about having IT involved in it.
Having end users is also critical and involved. You have to ask what is the company one out of our
solution? And are they going to get it? And most executives these days, they want to know are my
people going to use it? So to me, the strike zone for us is when we have an IT person who feels like
their needs are being met, a business person who feels like it's needs are being met for the
department. And we have some users who are giving that business person in the IT people a level of
comfort that this is not going to become shelf-wear. I think that's critical. And a lot of reps
lean towards having just one or two of those things and then feeling good. I have reps who will
just get the end users and I always have to coach them to get to power. And some reps who get to
power and then they forget to get the end users involved. And I think you've got to realize that
this is holistic and you need all those voices to really make your deal as airtight as possible.
Yeah, if I zoom out, you made me think about when I was selling deals over at PAVE, it was compensation
software. For us, it was very simple, similar. It was first discovery call. That's what gets you
the champion. Because usually in that first discovery call, you can figure out if there's the
transfer of enthusiasm there. In other words, did you find a problem that's worth solving? And nine
times out of 10, if you did, they were interested in hearing how you could solve it. And that was like
the first linchpin in the deal as you needed to find a champion who was like I'm willing to bang the
table. But then the second piece is getting them to believe you can actually solve it. And that
changes for every company. For you, it's like getting the trifecta of power champion and end
user in place because they want to make sure that adoption is going to work. For us at PAVE,
it was getting the VP of people or the CHRO to realize that this isn't going to solve an
operational problem. It's a cultural problem. So I knew that I could de-risk 90% of deals if my reps
were really good at discovery. And if they could tell the above the line vision story of how compensation
planning was going to impact retention in their org. But if they couldn't do those two things,
then nine times out of 10, it wouldn't matter what happened on the deep dive demo. Because at that
point, like you either nailed the discovery car you didn't, or the champion just sort of wanted to
see that it was going to work. And the real magic was going to happen on the next call with power.
I think everybody's business has to figure that out is like who's consuming your solution?
What benefits are they getting? And who does it touch day to day in the business? And you want to
understand that story. And then find the people that are affected by that story. Make sure that
every role is filled. So Brian, we've got time for probably like one more. We talked about a lot
of the early things where you're like building the story. Then mid stage we talked about like getting
multiple people involved. Let's talk about biggest risks when it comes to like deals going to close
in a matter of weeks kind of thing. So like late stage deal drops. What is the number one reason
that you find a late stage deal will drop and how do you be risked? What I'm going to actually say is
that I think that one thing you can do and that just about every sales rep can do to figure out
if there is a risk to get a constant pulse check on that and to also potentially solidify it
is talk about what happens next. Does your team have an implementation? Do you have a customer
success team? We have a CS team, okay? And I've made it a practice for my team. We have a great
partnership with them. They do wonderful work. In the client's mind, the contract is not the
finish line. The sales rep, I've heard sales reps say it, you know, let's get this across the
finish line. No, we're getting it to the starting line. So what can you talk about? What happens
after signature? And so I like to lay out if we have time and if it's the right deal, I like to lay
out like the way I do it is I talk about a 30, 60, 90 day plan, okay? This is really relevant to
audit because it's fast and easy to use. But I will say here's what happens day zero to day 30.
Here's what we're going to do. And these are the results you can start to expect. This is the
change you can start to expect. Days 31 through 60. These are some additional resources or things we
can do. And this is some of the additional things we typically see happen in your business.
And then 61 to 90. And when I talk about this, they get a sense you are partnering with me.
They will bring other people in. I've had deals that were at the finish line. We're trying to
figure out where we are with legal. We're wondering what's going on and we've reached out to the client.
said, we're planning our onboarding schedule for the next half of the month. I would love to introduce
you to your anticipated customer success resource. Let them talk to you about what happens and maybe
even figure out if we can pencil you in the schedule if you feel like we're close enough to getting
the contract signed. And we've had that meeting. We coach our team on it beforehand. Our team does
a great job of talking about value, talking about success and what's going to happen. They deliver
on those things. You know, in this one instance, I'm thinking of like, we got the contract signed
that afternoon. So talking about what happens next, I think, is so crucial. And I think so many people,
I don't know, they, they, they skip it or they don't do it. And so to all the sales reps out there,
figure out what resources you have in your bag, build strong connections with your CS team or your
onboarding team, find someone that you trust and can put in front of the clients and partner with
them to tell that story because it will make them look good. It makes their job easier at level sets
expectations and clients to light in that kind of an experience. We've talked about a lot of good
habits that sales people should be adopting to de-risk their deals. Last question is going to be
what's one bad habit you see from a lot of sales people that you think is leaving risk unchecked
in their deals that they need to stop doing so that they don't have all of these issues.
I'm going to speak to my team. I think this is relevant to everyone who gets leads. I coach my team
to be detectives. I want them to see a lead and I want them to think that they have one day
permission to go explore and gather information. I see so many reps who get a lead and they're a bit
passive with it. They might have a great discovery conversation and they might try and take it
and run from there. But they don't necessarily go on the outbound. So I think of leads almost
as like warm outbound and I think if you can take that same approach, you might find something that
your competitors don't have that the person who brought the deal to you doesn't have. It could be
something that further validates that this is a real need within the business. It could be an
area of the business that also is struggling with this that should get involved that doesn't know
maybe the left and right hand aren't talking with each other. There's so many things you can find.
But just by taking the effort to treat an inbound lead as permission to go explore and ask questions
within the company to do it in a professional and respectful way, I think that's a missed opportunity.
Oh, really good. Brian, thank you for joining us. Everybody stick around for a 60-second recap.
Coming up soon. Alrighty, next time for a two by two recap from this episode, Brian Charlton.
What do you have for your two? My first is do not tell your prospect that signing the contract is
the finish line. It's not it's the starting line. One of the ways that you can encourage your
deals to close is to start speaking to as Brian calls it the 30, 60, 90 of what to expect once the
contract is signed in the project starts. The framework he talks through for 30, 60, 90 is for each
of those periods he talks through what we will be doing in that period and then what results to
expect for each stage in that period. My second is oftentimes this is a discovery question that Brian
shared with us. A lot of times, prospects will come to us and they will tell you what they are
looking for. They'll show up and they'll say, yeah, we're looking for a conversational intelligence
tool. And the way that Brian flips their want into a real discovery conversation is he will
lay out the three to four things that he believes is making them look the pain points, the problems,
the priorities that might cause an HR team to be looking for a conversational intelligence platform.
And that's how he goes from product to actually having a discovery conversation in the first call.
Number three. Today's show was brought to you by Pipedrives easy to use and customizable CRM with built-in
meeting intelligence. Now, Pipedrives built
in meeting intelligence helps you focus on your follow-up question, not on scrambling to take
live notes. And we built a full discovery toolkit with them free in the 30 MPC Closers hub.
You need to be able to tell the internal story of the organization
too. So Brian talked about the three layers of the organization that he needs to get on board
for the story to be complete and for it to be believable that people will actually adopt it.
You need to get your champion on board. You need to get the VPs or the leaders on board with the
vision. But then in order for people to believe it's going to work, they have to have some
prove points from the end users. So figure out what that is for your sales cycle and go build a sales
motion around it. And then lastly, number four, if you ask to get in front of power and they say
no upfront, that's totally okay. First, you can focus on building more trust with that champion.
But then ask before you send another meeting, ask them what conditions need to be true for you to
be comfortable making that introduction. And you can call out the fact that if you've already gotten
as far as you should be, that hey, normally at this point, like we would have this level of trust
and use it as an opportunity to open the door and see if there's a truth in the deal that they
haven't spoken yet or haven't been comfortable sharing. Yeah, with you so far already, Nick.
How could we help us out? Yeah, you can help us out by sending a nice note to Brian and letting
him know if you enjoyed this episode. Go find him on LinkedIn. We'll link his LinkedIn in the show
notes. But send him a nice note. If you're learning to even one thing from this episode,
thanks for listening. We'll see you next week on the show.
Today's show is brought to you by Pipetrives easy to use and customizable CRM with built-in
meeting intelligence. Now Pipetrives built-in meeting
intelligence helps you focus on your follow-up question, not on scrambling to take live notes,
and we will take full discovery toolkit with them free in the 30 MPC Closers Hub. There's a link
in the show notes.
Podcast Summary
Key Points:
Sam McKenna revolutionized cold outreach and social-selling by leveraging network data and warm introductions to access accounts that ignore cold calls or emails.
Successful sales require anticipating best, alternative, and worst-case scenarios to de-risk deals and manage objections proactively.
Sales reps should control the call start by recapping client goals and early insights to build trust and alignment before introducing solutions.
When objections arise, ask open-ended questions to uncover underlying concerns—this reduces defensiveness and enables deeper, more human conversations.
A key deal risk is failing to involve multiple stakeholders, especially end users and decision-makers, which undermines adoption and long-term success.
The "strike zone" of most deals lies in the discovery call and in securing champions and end-user buy-in to ensure adoption and trust.
Sales teams should establish a 30-60-90 day plan post-signing to build client expectations and strengthen partnership with customer success.
A critical habit to avoid is treating inbound leads passively—instead, reps should actively explore the organization to uncover hidden needs and gaps.
Summary:
This transcript emphasizes transformative sales strategies rooted in human-centered conversations and proactive deal risk management. Sam McKenna demonstrates how using network data and warm introductions can bypass cold outreach resistance, while Brian Charlton outlines a structured approach to de-risking deals through scenario planning, stakeholder alignment, and discovery-driven conversations. Key principles include preparing for best, alternative, and worst-case outcomes, controlling the call’s opening with client-aligned questions, and deeply understanding the business story through multi-layered stakeholder engagement.
The discovery process is not just about identifying problems but uncovering the internal narrative—securing champions, gaining VP-level buy-in, and validating user adoption. A recurring theme is the importance of post-signature planning, where 30-60-90 day plans build trust and ensure successful onboarding. The episode also highlights a critical sales habit: treating inbound leads as opportunities to explore, ask questions, and uncover hidden organizational pain points.
Ultimately, success comes not from pushing a pitch, but from building trust, understanding the business context, and involving the right people across departments to make the solution both credible and adoptable.
FAQs
Sam McKenna emphasizes using relationship data and your network’s network to get warm introductions, which is more effective than cold calls or cold emails.
Instead of reacting, ask probing questions to understand the root cause—whether it’s a knowledge gap, shifting priorities, or lack of support—so you can address it constructively.
The strike zone is where most deals win or lose—first in discovery and second in involving key stakeholders like power users and end customers who will adopt the solution.
Involving multiple stakeholders ensures buy-in, builds trust, and increases the likelihood of adoption, as different teams can validate the need and value of the solution.
By conducting a 'pulse check' and discussing what happens post-signature—like onboarding, implementation, and customer success—before closing.
They treat leads passively instead of actively exploring the business to uncover hidden pain points or unmet needs that validate the opportunity.
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