WHITEPAPER

Six Modern Prospecting

Mistakes – and How to
Avoid Them
Six Modern Prospecting
Mistakes – and How to
Avoid Them
Emily Yepes
Sandler Trainer And Practitioner

Full disclosure: I’m one of those weirdos who actually enjoys prospecting and loves talking about it
at length. That takes a lot of people by surprise. But it’s true.

When new clients approach us about the possibility of Sandler working with their sales teams,
one of the first things we notice is that, for most of those salespeople, prospecting is a major
headache. It’s this big, scary challenge. And you know what lies at the heart of that uneasiness with
prospecting? Fear. It’s the basic, human fear of rejection -- the fear that most of us have about
hearing people say no. We don’t have to take that personally, but we do. I’ve noticed something
else, though: it’s not just about the fear of being rejected. There’s also a fear of uncertainty, of not
being able to feel confident about what works and what doesn’t. That’s another big part of the fear
people have built up for themselves about prospecting. They want to know: What’s the right way
to do it?

It’s not just about the fear of being rejected.

2 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

What we often hear from sales leaders and business
owners is that they’ve passed down their tried-and-true
methods from ten or twenty years ago; they’ve taught
In our post-2020 world,
their teams what worked for them … but now, it’s just not the game has changed.
clicking. They tell us, “Our salespeople just don’t get it.” Buyers these days just
And I’m here to challenge that. aren’t responding to the
old-school approaches
I’m here to question whether this is really about the
like they used to …
salespeople not getting it. I’m here to ask you to consider
the possibility that, in a post-2020 world, the game has because many of the
changed. I’m here to get you to consider the possibility prospecting techniques
that buyers these days just aren’t responding to the old- that used to work
school approaches like they used to … because some of
don’t work all that well
the techniques that used to work don’t work all that well
anymore. anymore.

Specifically, there are six modern prospecting mistakes that we help sales teams learn to replace
with newer, proven techniques that work a whole lot better. But before I can tell you about those
mistakes, I have to share one of our Sandler Rules with you. Our organization is famous for its selling
rules, and this one, in my experience, is an important one for anyone prospecting for new business
at this point in history. The rule sounds like this: If your competition is doing something, stop doing
it right away.

What’s fascinating is that David Sandler came up with this rule back in the 1960s … but it is
still completely relevant today. In fact, if anything, it’s more relevant today than it was back
then, because standing out from the competition really is a do-or-die proposition in our time.
Anybody who is in any sort of a leadership position knows what I’m talking about here: you get a
deluge of prospecting attempts in your inbox, in your voicemail, in your LinkedIn feed … every single
day. And how do you respond to them? You delete them or ignore them, the minute you figure out
that it’s a salesperson – or a bot. Sometimes, let’s face it, it’s hard to tell the difference!

So, our single biggest challenge as sales professionals is simply being seen. It’s standing out from
the crowd and getting the attention of our prospects. What follows is my take on the six most
common mistakes keeping us from doing that … followed by some strategies for replacing those
mistakes with tactics that we’ve found work a lot better in the modern marketplace.

AI MEANS SALES IS EVOLVING – BUT IS YOUR SALES TEAM? 3

 1 The first mistake is a lack of real personalization

This is the big one. Think of all of the messages you

get that try to sound personalized but really aren’t.
These Don’t Work:
For instance: “It looks like we have some mutual
connections, I’d love to learn more about your business.” “Look like we have some
This may have worked ten years ago, but today, mutual connections. I’d love
it doesn’t belong in anyone’s repertoire. It’s no longer to learn more about your
enough to get the attention of a prospect. business.?

The same goes for using the person’s first name “Emily, “Emily, I’ve been hearing buzz
I’ve been hearing buzz about your company,” or “Emily, about your company, would
I noticed your skills as a coach.” Or “Emily, it seems love to connect.”
like you’re doing some great work at Sandler “I noticed your skills as a coach
Performance Partners.” We don’t want to make the and decided to connect. Our
mistake of imagining that any of that is personalized, networks and skills could be
because today, it isn’t. Using the person’s name or mutually beneficial.”
the organization’s name isn’t personalizing anything.
Computers do that now, and they do it millions and “Seems likes you’re doing
millions of times a day. Buyers today see right through it. some great work at Sandler
We see right through it when we get messages like that. Performance Partners. How are
If it looks like a sales message and smells like a sales you handling this wild market?”
message, guess what? We delete it.

So, what do we do instead?

The simple answer is: We work really hard on the front end before we ever reach out to someone.
We create a hyper-personalized message.

That may not be what all of us are used to doing, but it’s what we need to do if we want to be
competitive. Before we ever reach out, we want to find some things that we can talk about that
will help us to make this case to each one of our prospects: Of all the people in the world, you are
the only person on the planet who could have received this particular message.

If we don’t make that case, then we don’t even make it onto the radar screen. I realize that’s a
paradigm shift. I realize it takes some effort on our side. But that’s the reality. And I promise you it
takes less time and effort than you may think.

Let me give you an example from real life. (And by the way, I have permission from my client to
share this.) Here’s Caitlyn’s initial message to Jerry, a decision maker who eventually ended up
working with her company:

“Hi, Jerry, thanks for connecting. The Mutant Sherlock Holmes activation at Comic Con was amazing.
I walked by as you were starting to let people through and wow, that was a big line.”

“Do you have your own team of brand ambassadors for those activations? Or do you use an agency?”

4 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

I want you to look closely at that. Did Caitlyn make the case? She did! The only way Jerry could have
possibly gotten that message was if Caitlyn had actually been there, noticed what was happening
at his booth, made a note of it, and then circled back to Jerry to reach out via email. Which she did!

Look how he responded:

“Great outbound message. It definitely has been the most impressive I’ve seen in quite some time.
So hats off. LOL”

“As far as sourcing, I have a network of about 20 BAs for Los Angeles and my colleagues do the
same thing for their event areas.”

“Hope this finds you well.”

Suddenly there’s a relationship – and a conversation. That’s what we want, of course.

Now, let me share some of the responses I hear from sales professionals when I share this example.
“That wouldn’t work for us.” “That’s too cutesy.” “People in our industry wouldn’t respond to that kind
of message.”

Here’s what I say in response: What you say to make your case is up to you – but you still have
to make your case. If you don’t make it crystal clear that the prospect is the only person in the
universe who could possibly have received your message, and lead with that, you will be ignored.
That’s just the reality of the world we live in now.

Am I saying you have to go to a trade show and watch what’s happening at someone’s booth
before you reach out to them? Of course not. We can use ChatGPT and Google and LinkedIn, to
name only three of the amazing tools at our disposal, to come up with some relevant observation
about the person we’re targeting. You can say anything you want, if what you say proves beyond a
shadow of a doubt that you’ve done your homework and you’re a) not a bot and b) not spamming
people with the same message, with minor tweaks, repeatedly. We’ve got to find something that
shows them clearly and immediately that we’ve done our research, that we care, that we know
something they care about, and that we’re reaching out with the intention to help.

SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM 5

 2 The second mistake is a weak or misaligned Call to Action

We’re all taught at some point that we need to ask for a Call to Action (CTA)– a request that the
person we’re talking to commit to do something. And usually, we do make that request. But the
landscape has changed. The calls to action that worked a decade ago with a brand-new contact
simply aren’t effective anymore. They don’t set us apart from the noise. In fact, they make us part of
that noise. I’m talking about calls to action like:

“Are you available this Tuesday or Thursday at 10 am?”

“Can we talk tomorrow morning?”
“What’s a good day for us to connect this week? Please let me know.”

In the situations where we have no prior relationship with the person, these are CTAs that,
statistically speaking, are highly unlikely to result in any action other than the person ignoring
us and our message. Is it possible these might have worked years ago, before decision makers
were so heavily bombarded with messaging from unknown sellers that a whole industry based on
blocking those messages emerged, and a whole new field of software designed to evade those
blocks took off? Absolutely. Years ago, this kind of CTA made statistical sense. Today, they are
premature. Buyers simply tune them out.
Look once again at Caitlyn’s CTA. It’s so subtle, you might have missed it – but it’s in there. She asks
Jerry, do you have your own team of brand ambassadors for those activations? Or do you use an
agency? In other words, she asks him a question that is relevant, easy for him to answer, and a
deepening of the conversation between peers. Make no mistake – that’s a CTA. She knew what
hers was. Make sure you know what yours is, too!
Those old-fashioned CTAs are a bit like going to a party, walking up to someone you’ve never met
and asking them if they’ll commit to a long-term relationship with you. You need a bit of back and
forth first!

Old-fashioned prospecting CTAs are a bit like going to a party,

walking up to someone you’ve never met, and asking them if
they’ll commit to a long-term relationship with you. You need a bit
of back and forth first!

Notice, too, that when Caitlyn asks those questions in the way she asks them (with the subtext
“Is this even something that’s worth talking about – is there even a possible fit here?”) she’s
establishing equal business stature. That’s very important – just as important digitally as it is
face-to-face. She’s testing for fit, which is what professionals do. They don’t waste their time or
anyone else’s.

6 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

 3 The third mistake is the failure to pick up the phone

This one surprises a lot of people. You read right. I want you to call people. Here again, I get some
interesting responses from salespeople. They say things like, “Emily, every time I actually hear back
from a prospect, they always email me back – they never call me back. So doesn’t that mean
phone calls are a waste of time?” No – it doesn’t mean that. And yes – if you’re doing this right,
that’s exactly what happens. Now, if you’re having a hard time getting your head around that, let’s
talk for a moment about the whole purpose of making a phone call … because that purpose is not
the same today as it was just a few years ago.
For professional salespeople today, the purpose of the phone call is not to have a conversation with
someone in real time when they answer the phone; these days, that’s just not likely to happen. We
don’t imagine they’re going to answer the phone – sometimes they do, of course, which is great,
but it happens so rarely that we can’t count on that. And we don’t want to imagine they’re going to
call us back after we leave a strong, professional voicemail message. Neither of those outcomes
is the purpose of making that call. The purpose of us making the call is to show that we are using
everything within our power to get in touch with this individual. That’s a powerful signal, and we
need to send it – professionally and appropriately, of course.
This one overlaps with the first mistake – the lack of real personalization. The only difference is that
instead of personalizing what I type, I’m personalizing what I say. So, yes, I’m going to pick up the
phone, and dial the number, and I’m going to leave a voicemail that says:

“Hey, Jerry, it’s Emily from Sandler. Since I didn’t catch you, I’m going to send you an email, explain
why I’m reaching out. Talk to you soon. “

That’s it.
I’m not going to ask them to call me back, I’m not going to give them a sales pitch, I’m not even
going to leave my number. (Their phone system probably shows them that anyway.) All I’m doing
is connecting the dots. The unspoken message here is powerful: I am the same person who is
trying to reach you via email, who’s trying to reach you via LinkedIn, who’s trying to reach you by
means of whatever platform, and I’m using all the different tools at my disposal. I’m professional,
I’m polite, I’m persistent, and I’m investing time, energy and attention in this conversation I want to
have with you, which is important.
Here’s why this approach is non-negotiable, as I see it. I don’t necessarily know, when I’m talking
to a prospect or reaching out for them for the first time, what the best way to get in touch with
them is. Think about it. We all know people for whom email is practically useless if you’re trying to
get through to them. Unless it comes from within their organization, or from someone they know,
they consider every message to be junk. We also know people who never log into LinkedIn, or log
into it so rarely that it’s pointless to try to reach them on that platform. Are you with me so far? I
thought so. We also know people whose voicemailbox is always full – either they’re bad at deleting
messages or they never seem to listen to the messages in the first place.

SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM 7

The point is, we don’t know what kind of person we’re dealing with when we’re reaching out to a
prospect for the first time. So, we’ve got to use all of the tools, figure out where we can find them,
and figure what the best way to communicate with them is. That runs counter to what a lot of
salespeople have concluded about phone calls these days, but what we see from the data is that
making calls is common practice among top performers. Research conducted by McKinsey in
2021 tells us that top performers make 82% more calls than low performers do and send 26% fewer
unsolicited emails. The top performers obviously don’t believe that prospecting calls have gone the
way of the dinosaur; by the same token, they don’t pretend calls are the main tool in their toolbox.
They use phone calls as a pattern interrupt. They use phone calls to break through the noise. And
that’s what I’m suggesting you should do.
And by the way, once you start doing this, guess what’s going to happen? You’re going to catch
some of these people on the phone. Not all of them, I know. But a certain percentage. And you know
what you’re going to hear? Someone’s going to say, “Wow – I never even saw any of your emails.”
Congratulations. Now you know a little bit more about how this person prefers to communicate.

4 The fourth mistake is not using combos

Using combos is a truly game-changing technique.

Most salespeople still haven’t heard of combos -- so let
me explain what I mean. When I use combos, that means
When I use combos, that
that, on a single day, I am reaching out to the same means that, on a single
prospect from more than one channel. So, on day one -- day, I am reaching out to
and by the way, what I’m about to share with you is my the same prospect from
own practice and the practice of most of our clients --
more than one channel.
I’m going to leave them a voicemail first, then I’m going
to send them a LinkedIn connection request, then I’m
going to send them a hyper-personalized email.

COMBO Day One

.Call; leave voicemail message

.LinkedIn connection request
Hyper-personalized email

Now, I realize that, for a lot of people, the first reaction to this kind of prospecting routine is going
to be to say, “That’s overkill. That sounds pushy.” You know what? It’s not. Listen to the technique.
We’ll assume I didn’t reach the person, since that’s by far the most likely outcome.

8 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

 “Hey -- This is Emily from Sandler. Listen, since I didn’t catch you, I’m going to send you an email
and explain why I’m reaching out. I’m also sending you a LinkedIn connection request to put a face
with the name. Talk to you soon.”

That’s it. If you do it authentically and with full confidence, as a peer, I promise it does not come off
as pushy at all. What’s next? I click through to LinkedIn, where I’m going to send them a connection
request. I may or may not put a little note in the request, but if I do, it’s not going to be a sales pitch.
It’s just going to point out that, as promised, I’m connecting a face with the name I left on their
voicemail, and briefly explaining that I’ll be sending them an email today as well. You’ve already
got an idea of the kind of email I’m going to send – I told you about it when we talked about the first
mistake, the lack of personalization.
As you can see, combos are really not overkill. The reason they’re not overkill is that I’m not giving
a sales pitch three times. I’m simply using every one of those channels as a way to clear away the
smoke. What I’m really doing is saying, “Of all the reach-outs you’re getting on a given day, there’s
this person named Emily from Sandler who is really trying to get in touch with you.” The combos
have a way of taking you closer to the place marketers call “top of mind awareness.” The whole
idea comes from the world of advertising. People have to hear your message multiple times in
order for you to even show up on their radar screen. That’s what this does.
So: what happens next? A couple of days later, I could move on to my second combo. It might look
like this:

COMBO Day Three

.Call; leave voicemail message

Email with personalized Vidyard message

And a couple of days after that, I might move on to the third combo:

COMBO Day Five

Call; leave voicemail message

LinkedIn Video Note

You get the idea. The whole time, the only thing I’m doing is making what the marketing people call
“touches” that create and deepening the recognition that a) I exist and b) I’m trying to get in touch
with them.

SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM 9

 5 The fifth mistake is a short or sporadic cadence

It’s impossible to overemphasize just how counterproductive this very common mistake is. What we
see often is that salespeople will make some kind of outreach attempt – let’s say it’s an email – and
then wait way too long before the next outreach.

Too often, salespeople will make some kind of outreach attempt

and then wait way too long before the next outreach.

Then they wait one or two weeks after sending that email… and leave a voicemail.
Then wait another one or two weeks … and send another email.
The problem is, if I’m a decision maker receiving these messages at such a spread-out cadence,
I can’t even begin to piece together that you exist, much less that you’re trying to reach out to me.
You’re just not on my radar screen.
The visual below, an example put together by our friends at Vidyard, shows a much better way to
go. This is what a planned cadence looks like. Obviously, you don’t have to follow this plan verbatim,
but we do strongly suggest you set up a cadence that works for you, one that sets up a clear
sequence without long gaps in it.

Day #1 Day #3 Day #5 Day #6 Day #9

— LinkedIn — Call — LinkedIn — Call — Call

Connection — Email with Message — LinkedIn Voice
Request Personalized Note

— Personalized Vidyard
Email
— Call

Day #12 Day #17 Day #20 Day #24 Day #30

— Call — Call — LinkedIn — LinkedIn — Breakup Email

— Email Research e.g. Message
(Automated) Like/comment
on an article

— Call

10 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

What this means is that I might sit down on day one and block out a big chunk of time, where
I am making my day one attempts for a list of 20 people. But if I get busy, and day five comes
by and I don’t get to the touch I was supposed to make, I essentially need to start over. That’s
the only way it’s going to be effective. So, you have to be ready to make that commitment.
Also, know that it’s going to take a couple of weeks of consistent effort before you begin to
start getting responses back. The first week isn’t going to explode in terms of conversations
and opportunities, because that is just not the nature of this particular game. You have to
build awareness and you have to be consistent. If you execute consistently over time, you will
get the results.

6 The sixth mistake is ignoring your digital presence

Reality check: there is such a thing as a buyer journey, in both business-to-business and business-
to-consumer sales. And guess what? These days, a predictable component of that journey is
people Googling you – as an individual. Are they going to look up your company? Maybe. But in
deciding whether and how they’re going to have a conversation with you, I can promise you that
every single buyer that you reach out to is going to give you a higher level of scrutiny than they give
your organization. Assuming you’ve done a great job at the hyper-personalization, they’re going
to be curious about you, and they’re probably going to do an online search about you before they
decide whether to answer you. That has to be our assumption. And if even if one good prospect
does and they don’t like what they see because of that search, that’s a problem.
I have permission to share with you a remark I heard during a conversation with a procurement
person at a large publicly traded company. That person said to me, “The first thing I do when
somebody reaches out to me is I look them up.” That’s a direct quote from someone in a position
of authority at a very large procurement department. What that quote says to me is that we all
need to expect an online search! And the marketplace is telling us the same thing. The trend I see
in the real world is more buyers, not fewer buyers, doing this kind of search to figure out who this
person is who’s trying to have a conversation. So: expect to be Googled. And accept that, usually,
what people are going to see when they Google you is your LinkedIn profile.

“The first thing I do when somebody reaches

out to me is I look them up.”
– Procurement officer

SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM 11

This is Dillon. Dillon is one of our clients. As you can see, he’s with Eleos Technologies. Dillon has done
a fantastic job of going into his LinkedIn profile and making sure that any prospect who looks him
up understands instantly what Eleos does, who he is, what kind of work he is engaged in, what level
of industry knowledge he has, and what he’s personally committed to about serving customers
in that industry. I want you to take a good, long look at Dillon’s LinkedIn profile page, because
what you will see there is a perfect example of conscious, strategic personal branding online for a
professional salesperson.
Did Dillon need a professional photographer to do a headshot for him to pull this off? No. Did
he have to hire a consultant? No. Did he have to write a single blog post? No. He just updated
his LinkedIn profile in a way that makes it totally user-friendly for his target audience. And I am
here to tell you: in a post-2020 world, if we don’t do what Dylan did, we’re going to be at a major
competitive disadvantage.
This next part is not necessarily easy to hear, but I have to say it: Most of us are at a serious
disadvantage because of this single, simple, easily fixable mistake. Most LinkedIn profiles of
salespeople read as though the salesperson is unhappy where they are professionally and is job
hunting – exactly the opposite of the message the salesperson wants to send!

Most LinkedIn profiles of salespeople read as though the salesperson is

unhappy where they are professionally and is job hunting – exactly the
opposite of the message the salesperson wants to send!

12 SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM

Now, that’s not entirely our fault. It happens because the defaults LinkedIn sets up tend to lean
toward the priorities of job seekers. We need to understand, though, that those defaults end up
selling us as individuals for a hiring manager to recruit! They’re not selling our company, they’re not
selling our products, and they’re not selling our service. Until we go in and intentionally rewrite our
profile strategically, until we make a conscious effort to ensure that a customer who looks us up is
going to get the images and the information they need, our LinkedIn profiles will do more harm than
good! That’s a situation we have to take responsibility for and proactively fix.

In Summary
Fixing all six of these common prospecting mistakes are priorities for salespeople and teams who
are serious about competing in a post-2020 environment.

.Lack of real personalization Failure to pick up the phone

Not using combos Short or sporadic cadence

Ignoring your digital presence

SIX MODERN PROSPECTING MISTAKES – AND HOW TO AVOID THEM 13

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