Your Guide to

Insight Selling
Success
by Mike Schultz & John Doerr
YOUR GUIDE TO INSIGHT SELLING SUCCESS
by Mike Schultz and John Doerr

TABLE OF CONTENTS
Why Insight Selling Matters .................................................................................... 1

What Is Insight Selling? ........................................................................................... 2

Attributes of Insight Sellers ..................................................................................... 4

The 3 Cs of Insight Selling ...................................................................................... 6

Insight Sellers Connect

Insight Sellers Convince

Insight Sellers Collaborate

11 Questions for Insight Selling ............................................................................ 16

19 Insight Selling Mistakes to Avoid ..................................................................... 18

Transform Your Sales Team .................................................................................... 20

WHY INSIGHT SELLING MATTERS

In the past several years there’s been a bit of a gold rush around the term “insight selling.” Research
from a variety of sources, including RAIN Group, has confirmed a simple fact: buyers buy from
sellers who are sources of ideas. So now everyone’s doing it.

This isn’t necessarily a new concept. The whole industry of management consulting has been in the
business of selling ideas for more than 100 years. The rest of the industries, however, have recently
jumped on the bandwagon.

The idea of insight selling goes like this: sellers provide insight into how a business can be
successful—they can give the ideas away for free—and they can bank on buyers buying their widget
in the process.

It turns out this works. It is, however, easier said than done.

The cold reality is that most sellers don’t bring new and valuable ideas to the table. Buyers see
through thinly veiled product pitches presented in a teaching wrapper. Sellers have to be better
than this if they want buyers to say something like:

I’m pitched ideas all day by sellers who think they were the first person who tried that on
me today. However, this one that just came by—they really got me thinking. I think they
have something worthwhile to offer.

What does the buyer and seller interaction look like—what does the seller need to be like—to be
able to produce this effect?

We cover this in great detail in our book, Insight Selling. You can learn more about the book and
purchase a copy by clicking here.

The rest of this guide covers the highlights and key takeaways from our book, so keep reading to
learn how to do insight selling right.

- Mike & John

Watch this video to learn more about how the shift in value
has moved from the product or service you’re selling to the
value you provide buyers.

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Your Guide to Insight Selling Success

WHAT IS INSIGHT SELLING?

Think about someone you seek out when you’re INSIGHT: WHAT SALES WINNERS
working through a challenge. DO DIFFERENTLY
They help you think things through and see The top three things sales winners do most
what’s important. They ask the right questions. differently from second-place finishers are:
They listen. They don’t just give you answers—
they help you come up with them. 1. Educate me with new ideas
and perspectives
And yet, they’re not afraid to tell you what they
think, share their ideas, and take a stand when
they feel strongly about something. 2. Collaborate with me

People like this make us better. They help us see 3. Persuade me we will achieve results
what’s possible. That’s why we get so much from
interacting with them. That’s why we seek them The common thread? They’re all about ideas.
out again and again.
Education is pretty straightforward in this
The sellers who are winning major sales these regard. When sellers educate with new ideas,
days are starting to look just like these people. they bring ideas to the table directly.

With the rise of the Internet, today’s buyers Great collaboration often inspires ideas. In fact,
have a lot of information and choices, but there’s plenty of research to suggest that great
they don’t necessarily have more wisdom or ideas come from collaboration because the
confidence. They need people to share ideas and ideas can mingle and swap.
help them think these ideas through.
Finally, “persuade me we will achieve results” is
Yet this is where so many sellers are struggling, about belief in the ideas and their merits.
falling short and losing, while a select few are
getting it right and winning. When sellers employ insight selling, which we
define as “the process of creating and winning
How do we know? sales opportunities, and driving change, with
ideas that matter,” they’re finding themselves in
We studied 700 business-to-business purchases the winner’s circle more often.
from buyers with $3.1 billion in purchasing
power. Our goal was to find out what the
winners of actual sales opportunities do
differently than those who come in second place.

We weren’t looking for any strategy or tactic in

particular. All we wanted to know was if there
were commonalities among sellers winning
sales, and the differences between the winner
group and the close-but-no-cigar group.

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Your Guide to Insight Selling Success

TWO CATEGORIES OF INSIGHT 2. Interaction Insight: Provides value in

SELLING the form of sparking ideas, inspiring “AHA!”
moments, and shaping strategies based on
There are two types of insight selling: interactions between the seller and buyer.
opportunity insight and interaction insight. You’re not just there to sell them something;
you’re there to shape ideas and inspire
1. Opportunity Insight: Focuses on changes that could benefit their business.
introducing a particular idea that is geared
to lead to a sale. To do this, sellers must Much as a trusted colleague might help
bring up the idea proactively. It’s the rare you come up with your own ideas, so does
BUYERS WERE 3X buyer that calls and says, “Hey, do you have the savvy seller who practices interaction
MORE LOYAL TO any new ideas for me?” It’s up to the seller insight. These sellers help buyers think
to create the opportunity and communicate outside the box by asking tough questions,
SELLERS WHO pushing them out of their comfort zones,
it so that the buyer says (or thinks), “Very
PROACTIVELY BROUGHT interesting. I didn’t know that was possible. and challenging their assumptions. When
OPPORTUNITIES TO If it works, it’ll be a huge win.” they do, buyers often come to insights on
their own. The net effect is that the buyer
THEIR ATTENTION. wants to keep that seller around. To do that,
Opportunity insight also creates customer
loyalty. While researching our book, Insight they buy from that provider more often.
Selling, we found that buyers were three
times more loyal to sellers who proactively Opportunity insight and interaction insight
brought opportunities to their attention. work together to build customer loyalty and
Educating buyers not only shares the seller’s earn repeat sales. Whether presenting the buyer
expertise, but also demonstrates the seller’s with a new opportunity, or simply collaborating
willingness to collaborate with the buyer. In with them, insight sellers drive change with
fact, that’s the second type of insight selling. ideas that matter.

Listen to my podcast, Buyers Want and Need Insight from Sellers, to

learn how I discovered the importance of providing insight to buyers in
my own sales efforts. - John

FROM NEIL RACKHAM'S FOREWORD TO INSIGHT SELLING

I ask you to forgive me a moment’s bitching if I pick out a particularly unhelpful trend in many of these about-to-become-best-
selling business books, especially those in sales, that use what I call the Armageddon selling formula.

The approach goes something like this: “Everything you’ve ever learned about sales is wrong and, unless you stop doing it instantly,
your sales efforts will shortly die in agony. There is, however, one simple cure that I have discovered. It is . . .” and here the author
puts in a pitch for the appropriate magic bullet, such as “my prospecting method,” “my selection system,” “our funnel management
process,” or “our trademarked social media analytics”—take your pick...

The Armageddon approach to sales doesn't help anyone. When, for example, a serious journal like the Harvard Business Review
publishes an article titled “The End of Solution Sales,” it damages the credibility of all involved. The sales field has been growing
up nicely in recent years: It can live without this kind of overstatement. As Schultz and Doerr point out, solution selling (or
consultative selling, as I prefer to call it) isn't dead or finished; it just needs to adapt to the new sales world.

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Your Guide to Insight Selling Success

ATTRIBUTES OF INSIGHT SELLERS

Insight sellers share new ideas and perspectives whole and tend to have the mental discipline
and collaborate with buyers to develop the best to think structurally and systematically.
solutions. They don’t just sell the value of their
products and services, they are the value. Without it—Ideas are poorly positioned.
Sellers tend not to create compelling
To succeed as an insight seller, we’ve identified solutions or inspire buyer confidence.
12 attributes (Figure 1), which we divide into
tendencies and qualities, that drive their success. 3. Curiosity: Insight sellers are interested in
people and situations. They have a thirst for
knowledge and strive to become experts.
THE 12 ATTRIBUTES OF AN
INSIGHT SELLER Without it—Sellers don’t seek knowledge.
They often don’t ask enough questions or
Insight sellers share seven tendencies—these listen. Insights they do share often aren’t
are the predispositions that drive how people new, interesting, or relevant.
choose to spend their time:
4. Sense of urgency: Insight sellers value
1. Passion for work and selling: Insight speed. They drive sales forward, are impatient
sellers have a desire for success in general with the status quo, and take action.
and for selling in particular.
Without it—Sellers let too much time slip by.
Without it—Sellers don’t do the work. They They don’t focus on actions that drive the
may be compliant, but they are not best results or push for decisions. They aren’t
committed to doing what it takes to succeed. change agents.

2. Conceptual thinking: Insight sellers 5. Assertiveness: Insight sellers take control

conceive innovative ideas and select the right and lead discussions. They defend their
strategies. They see how the parts affect the point of view and insert themselves into
important situations. They are not afraid to
create disruptions.
Figure 1. Attributes of an Insight Seller
Without it—Sellers don’t create the tension
or disruption required to create change.
They don’t practice interaction insight and
aren’t forceful enough to even get on the
buyer’s radar screen.

6. Money orientation: Insight sellers are

comfortable discussing money and
understand how businesses make money.
They are also motivated to maximize their
personal income.

Without it—Sellers tend not to qualify

prospects or establish return on investment
(ROI) cases necessary for driving new
initiatives forward. They don’t ask about

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Your Guide to Insight Selling Success

money and waste time chasing leads that Without it—Sellers are easily distracted.
don’t have a chance of closing. They don’t pursue the knowledge and skills
necessary for insight selling success.
7. Performance orientation: Insight sellers
manage their time ruthlessly and focus on 4. Integrity: Insight sellers have strong
results. They take advantage of moral values and they consistently meet
opportunities, manage their pipelines tightly, their commitments.
and are driven to win.
Without it—Sellers ruin their relationships
Without it—Sellers don’t manage their time when they’re uncovered for not being
or activities well. They make excuses and virtuous and success doesn’t last.
don’t make strong ROI cases.
5. Emotional intelligence: Insight sellers
These tendencies are the engines that drive an understand and manage their own and
insight seller’s actions. But tendencies are only others’ emotions. They can handle difficult
half of the story when it comes to what it takes personalities and adjust their style based on
to succeed as an insight seller. Insight sellers the buyer. They don’t panic, get distracted, or
also share 5 qualities that guide their success. react emotionally.

If tendencies are the engines of behaviors, Without it—Sellers don’t create or succeed
qualities are the platform and the rudder: in situations that require tension. They get
flustered and lose focus easily. They also
1. Gravitas: Insight sellers are substantive, have a difficult time creating and
confident, and credible—they are people to maintaining a peer dynamic.
be taken seriously.
Anyone can come to a training class and
Without it—The advice of the seller is not learn a skill, but not everyone will a) become
valued or taken. They tend not to succeed good at what they learn, or b) apply new skills
with executive buyers and they wilt under and behaviors when selling. Getting to top
pressure, such as in a negotiation. performance depends on whether the person is
the right fit for the role.
2. Business acumen: Insight sellers are quick
to understand situations. They give advice And the right fit, when it comes to becoming
and make good decisions. They understand an insight seller, is very much determined by
organizations, people, change, innovation, these 12 attributes.
finance, and accounting, along with the key
drivers of profit and success in business.

Without it—Sellers don’t establish credibility

or communicate insights and advice leading
to good outcomes. They don’t drive action
and change and don’t make strong ROI cases.

3. Perseverance: Insight sellers are willing to

do what it takes to succeed. They focus on
the task at hand, and stick with it for the
long haul.

Watch the webinar, What It Takes to Sell with Insight, to learn how
providing insight helps you close more deals and enables you to have
deeper, longer-lasting client relationships.

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Your Guide to Insight Selling Success

The 3 Cs OF WINNING SALES

You now know what insight selling is and the INSIGHT SELLERS CONNECT
attributes of the best insight sellers.
Insight sellers connect in 2 ways:
In the rest of this guide, we’ll outline what you
need to do to excel with insight selling. 1. They connect with buyers

As we analyzed the research on what sales 2. They connect the dots between buyer
winners do differently, we discovered that needs and their solutions
the way winners sell can be characterized by
specific behaviors at three different levels:
CONNECTING WITH BUYERS
+ Level 1: Connect There’s been a lot of noise the last several years
Winners connect in two ways. First, they declaring the death of relationship selling. “The
connect the dots between customer needs Internet has changed everything.” “Personal
and their company’s products and services connections don’t matter anymore.” “Selling is
as solutions more effectively than second- not about relationships.” “Throw out everything
place finishers. Second, winners connect you thought you knew about sales, Armageddon
with people. Buyers believe that winners is coming!”
both listened to them and connected with
them personally more often than the rest. We strongly disagree with the idea that selling is
not about relationships. Relationship building is
+ Level 2: Convince still critical to winning sales. But it has changed.
Winners convince buyers that they can
Our research found that sales winners make
achieve maximum return, that the risks
strong personal connections at more than
are acceptable, and that the seller is the
double the rate of second-place finishers.
best choice among all options. Many
Relationship building in sales is far from dead.
sellers are not good at convincing buyers,
So what’s changed?
and a large portion of sellers aren’t even
willing to convince. When they can and
do, they win more sales. HAND SHAKES, LUCKY STRIKES,
AND THREE-MARTINI LUNCHES
+ Level 3: Collaborate
Let’s first take a look back at how sales
Winners are collaborative in how they relationships were forged in the Mad Men era.
work and what they do. They are
perceived by buyers to be responsive, Classic relationship selling in the 1960s
proactive, and easy to buy from. And involved a lot of schmoozing. It was, “Let’s have
buyers believe winners actually collaborate lunch. Let’s have dinner. Let’s go to a show. Let’s
with them during the buying process by go to Sardi’s. Let’s meet the family. Let’s do it
working together to achieve mutual goals. again.” Then, “OK, I like you. Let’s do business.”
Buyers perceive collaborative sellers to
be integral to their success. The relationship came first in a world that was
very localized, where buyers and sellers could
If you want to apply insight selling, you must sit down face to face.
excel in these three levels.

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Your Guide to Insight Selling Success

So what happened in those three-martini mean the personal connection is any less
lunches? valuable (Figure 2).

When sellers build personal connections with As insight sellers establish themselves as
buyers, they lay the foundation for trust and trustworthy sources of value, buyers open up
establish their business value. In the Mad to an exchange of information and ideas. If the
Men days, personal connection often came buyer likes and trusts you, they’re more apt to
first, before the sale occurred. Relationship take your advice. This increases your business
building in sales occurs, however, in two value, along with the frequency and depth of
categories—personal connection (based on interactions with the buyer. That’s a solid buyer-
common affinity and liking one another) and seller relationship. It just happens in a different
business value (connection based on strength order than in the wine-and-dine-the-client-
of business impact). before-they-buy times (Figure 3).

Now, some so-called sales pundits say, “Don’t

bother with that. A personal connection is Figure 3. Buyer Openness to Insight Directly
unimportant. Relationship builders aren’t Correlates to Trust
top performers.” Or they define relationship
building in anachronistic terms, such as
“being generous with your time” or “making
everyone happy and harmonious.” We don’t see
relationship building that way. In any case, it’s
not dead. Not by a long shot.

HOW SALES RELATIONSHIPS HAVE

CHANGED
Relationship building, the personal side, is still
critical to earning trust and winning sales.
What has changed is the way customers form
relationships with sellers. Today’s sellers and
buyers often determine business value first.
They vet each other’s businesses and decide if
they want to work together—but they don’t go
out for extended cocktail-tipping lunches like in
Source: Schultz, Mike, and John E. Doerr. Insight Selling:
the Mad Men days.
Surprising Research on What Sales Winners Do Differently.
Hoboken, NJ: John Wiley & Sons, 2014.
Today, the business interaction comes first, with
the relationship being the reward customers
give sellers who work for it. But that doesn’t
Indeed, the world has changed. The rhythm
has changed. The order in which we do things
Figure 2. When Business Value Comes First
has changed. But what hasn’t changed is the
need to build strong personal connections
with buyers. Dismissing the value of personal
connections is ill-advised.

Relationship building in sales is alive and well.

We don’t see that changing any time soon.

Source: Schultz, Mike, and John E. Doerr. Insight Selling:

Surprising Research on What Sales Winners Do Differently.
Hoboken, NJ: John Wiley & Sons, 2014.

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Your Guide to Insight Selling Success

FROM NEIL RACKHAM'S FOREWORD TO INSIGHT SELLING

The traditional wisdom has long taught that relationship building is the foundation of all business-to-business selling and much of
consumer selling, too. However, particularly since the publication of The Challenger Sale in 2011, the Armageddon enthusiasts have
been widely putting it about that relationships have become unimportant and that relationship selling is in its death throes. Again,
nothing could be further from the truth.

What has changed is the way customers form relationships. In the past, the sequence was for salespeople to build the relationship
first and then to sell. Today few customers have the time or the inclination to build relationships before the sale. Instead, the
relationship is the reward that customers give to salespeople who have created value for them.

So, the sale comes first and the relationship building starts from there.

CONNECTING THE DOTS In our research we looked at what the

winners of actual sales opportunities do
Insight sellers don’t just connect with people,
differently than second-place finishers.
they connect the dots between buyer needs and
LOOKING AT THE seller solutions.
Of the 42 factors we studied, “deepened my
understanding of my needs” was 40th on the
DIFFERENCES BETWEEN list of what winners do. Winners barely did
WINNERS AND SECOND- Think of the classic solution sales concept:
it compared to the rest of the factors, yet
diagnosing and connecting the “pain” of the
PLACE FINISHERS, buyer with the products, services, and overall
they still won the sale.
“UNDERSTOOD MY NEEDS”
capabilities of the seller as “solutions.”
Second-place finishers actually focused
WAS THE FIFTH LARGEST more on diagnosis than the winners, yet they
In our research, we found that while this
GAP. IN FACT, WINNERS concept is still alive and necessary today, it has
still lost.
DEMONSTRATED THEY changed in three very important ways.
While sellers may not have to diagnose
UNDERSTOOD BUYERS’ NEEDS as often or as deeply anymore, they do have
2.5X MORE OFTEN THAN 1. Understanding vs. diagnosing needs: to demonstrate understanding of need. This
In solution sales, there’s typically a heavy is critical. The terms may seem similar, but
SECOND-PLACE FINISHERS. emphasis on the seller “diagnosing” the throwing the “understanding” baby out
needs of the buyer. The need for diagnosis with the “diagnosing” bath water is not a
implies that the buyer doesn’t have a good idea.
thorough understanding of why they find
themselves in their current, undesirable Looking at the differences between winners
situation or what to do differently. Through and second-place finishers, “understood
diagnosis, the seller figures this out like a my needs” was the fifth largest gap. In fact,
doctor might with a patient who feels winners demonstrated they understood
unwell, but who doesn’t know what they buyers’ needs 2.5 times more often than
have or what to do to get better. second-place finishers. On top of that, of the
42 factors, buyers said “understood my
needs” was the fifth most important factor
that second-place finishers should change in
order to win their business.

Fundamentally, sellers need to shift

from diagnosing needs to demonstrating an
understanding of needs.
These days, diagnosing needs isn’t nearly
as important as simply demonstrating
understanding of needs.

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Your Guide to Insight Selling Success

2. Focusing on pain: Another needed 3. Necessary, but not sufficient to win

change is a shift away from the prevalent use the sale: While a solution sales approach
of the words “problem” and “pain.” These are used to be enough to win the sale, it’s now
the two most common terms associated with only the price of entry (Figure 4).
discovering buyer needs. These words all too
often drive sellers to employ find-out-what’s- Imagine for a minute that someone is selling
wrong-and-fix-it thinking. to you and you perceive the seller doesn’t
understand your needs and doesn’t craft a
Let’s say the buyer doesn’t perceive compelling solution. Their chances of
anything—or anything important enough winning business from you are probably
to act on—to be wrong. Soothe-the-pain pretty slim.
sellers find themselves at a dead end. No
problems to fix. Nothing to sell. Now consider that the seller demonstrates a
strong understanding of your needs and
Insight sellers, however, don’t just focus crafts a compelling solution, but you
on the negative, they focus on the positive— perceive that they aren’t listening to you
goals, aspirations, and possibilities and you haven’t made any kind of personal
achievable by the buyer, even if the buyer connection with them. As long as any other
doesn’t know it yet. Along with having seller meets the minimum criteria, you’re
much richer sales conversations, focusing unlikely to buy from the unlikeable seller
on the positive opens the door to significant who isn’t listening.
opportunity to increase sales.
The point is: sellers who do a good job, even
Sellers who focus on aspirations as well with these changes to the traditional
as afflictions are able to directly influence solution sales approach, haven’t yet won the
the buyer’s agenda by inspiring them with game, but they’re in it.
possibilities they hadn’t been considering,
but should.

Figure 4. Changes to the Basic Premise of Consultative Selling

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Your Guide to Insight Selling Success

INSIGHT SELLERS CONVINCE the game, or an overview of any relevant

issue that gets the buyer saying, “This seller
gets it,” or, “They get us.”
CONVINCE
con·vince /kәn'vIns/ When we observe seller presentations, all
too often we see that sellers and their
1. Cause (someone) to believe firmly in the products are positioned as the hero. This is
truth of something. a mistake. The buyer is the hero. Everything
the seller does should serve the master of
2. Persuade (someone) to take action. being relevant to the buyers, presented in
their context, and focused on how to make
Building confidence in the validity of an idea. them successful. With the buyer as the hero,
Inspiring action. sellers do a much better job connecting
while they convince, ultimately persuading
While a few do insight selling naturally, the buyer to take action.
many struggle. Sellers might know with great
certainty that when buyers buy they’ll be better Once sellers connect with the buyer and
off as a result, but they just can’t get the buyers establish they know what they’re
to believe it too. talking about, they’ll get the buyer’s attention
and build curiosity in hearing the rest of
What’s interesting, though, is that the sellers what they have to say.
CLICK HERE FOR A PDF OF who are good at selling an idea and those who
aren’t often both understand the idea and its
THE CONVINCING STORY importance. It’s just that some communicate it
2. Dissatisfaction – Name the Adversary:
Next, establish the current state and why
FRAMEWORK. far better than others. it’s not good enough. The heart of every
action and change—and a key component
Those who do insight selling well—whether of opportunity insight—is the buyer’s
they know it or not—satisfy the same basic desire to be in a different, new place. When
criteria every time, following the same story you identify the current state and why it’s
format. And the great thing is this: the basic unacceptable, you give the adversary a
structure is simple and learnable. We call this name. You put a target on its back.
basic structure a Convincing Story (Figure 5).
The adversary can be almost any set of
Essentially, every Convincing Story should afflictions: lack of results, slipping market
answer three questions: share, wasted time on work-arounds, ideas
whose time has passed—anything. Insight
+ What do I want them to learn? selling masters don’t just tell people what to
run towards; they also give people
+ What do I want them to feel? something to run away from.

+ What do I want them to do? 3. Desire – Establish the Destination:

People have a natural tendency to drive
forward. But if they don’t know where
HOW TO TELL A CONVINCING they’re headed, as they say, any road will get
STORY them there.
The seven key components of the
Convincing Story are: Your ability to establish the destination—
to help the buyer imagine some specific
1. Connection – Establish Credibility: aspiration—is critical. Average sellers focus
Build rapport and establish credibility by on establishing the path. They talk about the
demonstrating keen insight into the buyer’s product: “This is what we do and the way we
world. You can do this with an overview of do it.” These are how messages. Nobody
industry trends influencing buyers, an cares about the how until they feel the
overview of technology issues that change depths of the why.

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Your Guide to Insight Selling Success

Figure 5. Convincing Story Framework

Source: Schultz, Mike, and John E. Doerr. Insight Selling: Surprising Research on What Sales Winners Do Differently. Hoboken, NJ: John Wiley & Sons, 2014.

The destination establishes—in RAIN How you establish dissatisfaction and desire
Selling terms—the possible New Reality. isn’t a linear process. To do it best, weave
What you get when you achieve the new back and forth between the undesirable
reality is the answer to the question, Why? current state and desirable future state.
Answer powerfully enough and you
establish the basic premise for any change, As you do this, describe stories of what
leaving behind a dissatisfactory current state companies (or the buyers themselves) have
in favor of a new, improved one. tried that failed. Describe (and later,
overcome) common objections to moving
4. Dissatisfaction Layering – Journey forward. The net effect is that the audience
to the Depths of Despair: Simply feels the undesirability of the current state
suggesting, “Here’s where we are and it isn’t more strongly; they have been reminded that
good enough,” isn’t, well, good enough. It’s others have been trapped here have tried to
too antiseptic. It doesn’t create the intense get out, and couldn’t. Because people relate
feeling of desire that’s so important for change, stories to themselves, they’ll feel trapped as
and so critical for insight selling success. well. They’ll feel the failure of others.

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Your Guide to Insight Selling Success

At the same time, you will remind them of 6. Results – Communicate Results, Create
the possible new reality that seems out of the Feelings: The better you can build a
reach. By moving back and forth between custom ROI case and show previous similar
the current state and the possible New results, the more confidence you’ll build that
Reality, you not only establish a very the buyer can achieve them, too. When you
important rational gap (you’re here, but show what others have achieved, you
you could be there), but you also maximize strengthen the emotional journey because
the negative feelings associated with being in buyers will imagine themselves having
the bad place and stoke the desire to get to achieved those same things. They’ll envy the
the good place. results, and he again, envy is potent.

5. Breakthrough! – Introduce a New As much as some will argue to the contrary,

Hope: Just when buyers feel resigned business buyers, like consumers, buy with
to continue on with life in the undesirable their hearts and justify with their heads.
current state—where many (like them) are Selling an idea isn’t only about selling the
stuck—you show them a different path. A numbers. Use the Convincing Story
path they do not know about that others structure and you’ll give buyers the financial
have taken to successfully climb out of the justification case they need for themselves
hole. A new hope! and others with ROI. Also you’ll cause them
to want the results and everything else your
When they see what others have achieved solution delivers all the more.
when they made a change, they’ll want to
achieve the same. The concept is envy, and 7. Action – Invite Collaboration: Every
envy is a powerful emotion. Still, making the seller has been told to recommend action,
change a reality is not necessarily a slam specifically a next step, at each stage of the
dunk. If it were easy, everyone would do it. sales process. Scarce is the advice, however,
However, this is what you help people do— to build in collaboration as an explicit step.
and what you have a track record of doing. When buyers feel that sellers collaborate
You can guide them around the many pitfalls with them, they are much more likely to
that can get in the way. buy, and to buy from that particular seller.

This establishes you not only as Many sellers try to move too quickly to
differentiated (the best choice—the only make a sale. Jumping from here to closing
choice!), but also as a straight shooter who’s is a big leap. By asking only for a
on the buyer’s side. Do so and buyers will commitment to collaborate, you shorten
start to believe you and trust in you and the that leap with a stepping stone that
solution that much more. moves you closer to the sale, and increases
its likelihood of happening.
Some sellers get this far but then don’t
confront the harsh realities of what might Collaboration is a core component of insight
go wrong. When this happens, buyers see selling and the Convincing Story framework.
the solution and understand that the ROI Collaboration involves the buyer in the story
case is compelling, but they still doubt they itself. When people are involved in
can achieve it or doubt the seller’s motives something, they become invested in its
if they feel like the seller is holding back. success. The more they become invested in
Sellers who are forthright convince buyers something, the more they take ownership of
that their knowledge, collaboration, and seeing it through.
trusted partnership in the journey is
essential to their success.

Watch the webinar, Become a Source of Insight for Buyers:

How to Sell Ideas and Drive Demand, for an example of the
Convincing Story framework in action.

© RAIN Group | [Link] | 12

Your Guide to Insight Selling Success

Perhaps most importantly, collaboration There you have it: the elements of a
creates shared experience. Shared experience Convincing Story, an essential component to
leads to intimacy in the “I know you really persuading prospects.
well” sense. Intimacy is a pillar of trust. And
trust is essential for buyers to take a leap Use the Convincing Story structure and you’ll
of faith with you and buy whatever it is achieve the three outcomes you need to sell:
you’re selling. learn, feel, do.

LEARN FEEL DO
+ Current state is not good enough. It + The depth of how undesirable their + Collaborate with you to bring the New
needs to change. current state is. Its frustrations, Reality to life.
problems, and difficulties.
+ You “get it” and “get them” because,
without even talking with them much + The full desirability of the possible New
and like reading their minds, you’ve Reality and everything that comes with
described what their world is like. it (e.g., money, success, attention, relief,
happiness), even envy of those who
+ Possible New Reality is much more have what they don’t.
desirable. The stakes are high if you can
win this game. + Confidence that you, your offering,
and your company can help them get USE THE CONVINCING
+ The rational impact (the ROI) is clear. the results. STORY STRUCTURE AND
+ There’s a path to get there, but it requires + Confidence that the result is achievable YOU’LL ACHIEVE THE THREE
different thinking and action. and, at the same time, worth the risk. OUTCOMES YOU NEED TO SELL
AN IDEA: LEARN, FEEL, DO.
+ Do it right and results are achievable.

INSIGHT SELLERS COLLABORATE priority of making a sale happen, and make it

the buyer’s priority to make a purchase happen.
When buyers buy something, one of two things
must be true: It’s not that easy, though, because you’re nowhere
near the buyer’s priority list when you start.
1. They are required to buy.
The keys to moving up on a buyer’s priority list
2. They want to buy. are desire and ownership:

In the former, they have no choice. Get sued, + Desire: They really need to want what
hire a lawyer. Buying = required. The lawyer you can do for them.
doesn’t need to convince the buyer why to buy
legal services in general, only why to buy them + Ownership: You need to take something
from them. that wasn’t even on their radar screen and
get them to believe deeply, “I need to do
In the latter, the buyer has a choice. Buying something about this!”
= desired. They don’t need to buy, but if they
want it badly enough, and have the money and Perhaps the most overlooked strategy for
authority to buy, they buy. creating buyer desire and ownership is getting
them involved in the selling process by inviting
Since the buyer isn’t required to buy when sellers their collaboration.
drive demand, sellers must be able to take their

© RAIN Group | [Link] | 13

Your Guide to Insight Selling Success

Sellers who win the most sales collaborate with problems. What effects do you think you
buyers almost three times as often as the sellers might see? What would the impact be?
who come in second place. In almost every sales
situation, collaboration helps.

5 STEPS TO COLLABORATE WITH

“


This is why we think it’s possible that you
could increase revenue 20% by getting
your marketing engine firing on all
thrusters. We realize, however, that as
BUYERS IN THE SALES PROCESS much as most company leaders would
Here are five steps to engage buyers through want this kind of revenue increase, they’d
collaboration: be skeptical that it would actually happen.
Listen to the Why wouldn’t this work here? What
podcast, 5 Steps for 1. Prepare buyers to collaborate: Set a would the roadblocks be?
Collaborating with meeting that opens the door for
Buyers and Increasing collaboration. For example, you can set the 3. Ask incisive questions: If you created
Sales, to learn how meeting with the stated premise of sharing the opportunity and asked for the meeting,
some ideas you think may be worthwhile to it’s up to you to set the table, set the tone,
to work with buyers a buyer, but the ideas aren’t finished and and define the platform and agenda for the
to create ownership you need their help to think them through. discussion with advocacy.
and investment in the This opens the door for their involvement
buying process. in the process. But that doesn’t mean you don’t ask
meaningful questions early in the selling
Then kick off the meeting with the right process that force the buyer to think, make
introduction and expectations, including the buyer uncomfortable, and get to the
asking them to dive in with thoughts and heart of issues. Examples:
questions at any time.

When you engage buyers, the idea is to
invite them to be an active participant in “ Is inaction on the issue hurting your
productivity and morale?

“
a process, not someone who listens to a pitch If you know that you need to do something
and then decides “up or down” on buying about it, why haven’t you taken action yet?
what you’re selling.

“
You took action and it failed in the past,
2. Wonder with the buyer: When sellers but it seems like you’re considering doing
create their own opportunities, they often something similar again. Why is it going to
err on the side of over-pitching. The seller turn out differently this time?
pitches, hoping to inspire the buyer. The

“
buyer sits there disengaged, even when the When I’ve seen similar issues like yours,
ROI seems huge. such as A, B, and C, it’s usually a recipe for
big problems like X, Y, and Z to eventually
The problem is not in the impact the crop up. But you don’t seem terribly
product or service can have on the buyer, it’s concerned. Could you make the case for me
the psychological effect of not being that X, Y, and Z won’t happen here?
involved enough in the discussion. Early
on, ask the buyer to wonder with you about
possibilities. For example, you might say: These questions are not puffball variety.
They’re edgy. They’ll probably make the

“
buyer uncomfortable. Good.
So it’s happened like this at our other two
client sites. Given what we discussed so
far, imagine for a minute you implemented Read this article, Generate
something similar, and it’s six months from More Leads with Existing
now. What effects do you think you might Accounts through Value
see? What would the impact be?
and Collaboration, for

“ You mentioned that A and B are not an email example of exactly how to
issues for you, but C and D are. Imagine for set meetings with current clients that
a minute that C and D disappeared as open the door for collaboration.
© RAIN Group | [Link] | 14
Your Guide to Insight Selling Success

If the buyer has great answers to your tough Note: don’t just ask the buyer how to move
questions—answers that make you think, forward without defining parameters. “What
“Okay, you don’t need any help,” then good. do you think we should do from here?” is
Now you can move on to other opportunities. too open-ended. They might not have a
And good for them, as you’ve helped them concept of what to do, and they might pick
see why they’re in great shape already. something that isn’t the best choice for them.
It’s usually best if you give them a vision of
If they can’t knock your tough questions what you think is the best path, and then
out of the park, you help the buyer see that allow them to shape it with you.
the status quo isn’t good enough. This means
action is necessary. (See page 16 for 11 5. Give the buyer ownership of the idea:
specific insight questions to ask.) Take, for example, the last point. The buyer
might say, “The best thing to do is this…”
4. Shape the path forward together: You might already know that, but don’t say,
Most of us don’t only sell one offering. Many “Yes, I’ve been thinking that for much of the
sellers have flexibility in the service or meeting.” Do this, and you snatch the idea
product package, delivery, and overall away from them and claim it as your own.
solution they eventually craft.
Instead say, “I think that’s a good idea. In
When the buyer has a hand in shaping the fact, I bet it will work.” This way you allow
solution, they feel a sense of pride in them to keep ownership of the idea. When
ownership, and their commitment to seeing they own the concept, it increases their
it come alive grows. desire to see it through.

You might say, “Given what we talked about, Collaborate with your buyers throughout the
I think it would work well to do A, B, and C selling process. Not only will you get on their
here, but I think we have open questions priority lists and shape their agendas for action,
about some of the details. You mentioned the likelihood they’ll take that action with you
before that X might get in the way of will skyrocket.
implementation. How do you think we could
get A, B, and C done so that X doesn’t get in
the way?”

The buyer might respond with, “Well, it’s a

sticky one. In my experience, the best thing
to do is…”

Watch the webinar, The Missing Link to Winning More

Sales, for more ideas on how to collaborate with buyers.

© RAIN Group | [Link] | 15

Your Guide to Insight Selling Success

11 QUESTIONS FOR INSIGHT SELLING

Too many people think insight selling is about 3. What have you tried that hasn’t
educating buyers through presentations. worked? This question will help you
They’re about half right, but without the other understand their thinking, and will help you
half, they’re missing out on the full impact of see the gaps between what they know won’t
insight selling. work, and what you know will.

The missing link is asking questions. Or, as we 4. Have you considered A…B…C…
call it, inquiry. etc.? You may find out they did, but didn’t
approach it right or didn’t know about a new
Insight selling in any form hinges on the advancement in the area. Maybe they didn’t
concept of cognitive reframing. Cognitive know better options existed, and you can
reframing refers to creating alternative ways of bring them to the table.
viewing ideas, events, situations, possibilities for
action, or anything. Influence buyers’ thinking 5. If I said I believe you might have
with your insightful inquiry and you can then under-invested to achieve this
influence their agenda for action. outcome in the past what would you
say? When many buyers try to do something
This is what insight selling is all about. Here are the first time, they look to cheaper options.
11 questions that can help you do just that: Then those cheaper options fail.
1. Why? “Why is that your strategy?” “Why do This kind of question can push buyers out
you say that?” “Why do A versus B?” By of their comfort zones. You challenge them,
asking why, you are asking buyers to justify but not in a standoffish way. They might say,
something. If they can do so convincingly, “Well, what should I have done?” Or, “The
then bully for them! But oftentimes they ROI wasn’t worth putting in more.” Most
can’t. Sometimes, when buyers respond to answers give you opportunity to bring
the “why” question, they give the insight insight to the table.
to themselves. But even if they don’t, that’s
an opportunity for you to help. 6. What will the impact be if you did this?
Answers here can show:
When you ask why questions, be careful not
to put the buyer on the defensive. Deliver + They see the impact and why it’s
with a tone of inquiry and collaborative important (good!)
thinking, not of questioning their judgment.
+ Their perception of the impact grows as
2. How? “How do you see this all panning they think it out (great!)
out?” “How do you think you need to
proceed so this becomes a part of the
+ They see the impact as too small for
culture?” “How might you avoid the
action (you can show them it’s bigger!)
common challenges like X, or Y, or Z that
commonly crop up?”
+ They don’t know (you can help them
figure it out!)
“How” questions get people thinking about
reality. Sometimes they have strong reasoning
for why to do something, but they don’t have 7. What will happen if you don’t act?
a strong plan for how to get things done. Ask Asking this question gets buyers thinking
how and you can spark insight. of the negative consequences of inaction.

© RAIN Group | [Link] | 16

Your Guide to Insight Selling Success

They may work it out themselves (“We’ll 11. The follow-up question(s). Ask a
bleed cash!” “Turnover will be unsustainably question, and you may get a somewhat
high!”) and their perception changes. solid, somewhat thorough, and somewhat
Perhaps they need your guidance to see the convincing answer. Keep pressing, though,
negative consequences of inaction. Either and somewhat solid answers and
way…insight. arguments break down.

8. What’s possible? “What’s possible for These types of questions lead buyers to say (or, at
results?” “What’s possible for action?” least, think) things like, "Well, I wasn’t thinking
“What’s possible for solution choices?” Like of it like that." When they do, you’ve helped
impact, whatever you find here gives you the them achieve cognitive reframing: influencing
chance to then alter their perception. the way they think and what they believe.

9. How do you know that? Buyers often Influence buyers’ thinking with your thoughtful
give “facts” without foundation. Or, they inquiry and you can then influence their
may give facts with foundation that once agendas for action. The trend in selling has been
was true, but isn’t anymore. By asking for to do this only through advocacy. Now you
the reasoning behind a statement, you can know how to do it with inquiry as well.
help the buyer question the fundamental
basis for their assumptions.

10. What do you think is missing? This

is the question that often gets a response of,
“Good question!” Or, people get up on
their soap boxes decrying what “should be”
but isn’t. Openings for insight all around.

© RAIN Group | [Link] | 17

Your Guide to Insight Selling Success

19 INSIGHT SELLING MISTAKES TO AVOID

Like anything, insight selling comes with its CONNECT

own potential pitfalls. To help you avoid them,
we have outlined the most common insight + Equating insight selling with
selling mistakes. Some points are tactical, and pitching: Embracing insight selling does
others strategic. Each is listed under a general not lead to an altogether rejection of
area key to insight selling success. solution selling concepts. When sellers
make this assumption, they forgo
questioning, listening, and understanding
OVERALL in favor of taking up the mantle of an idea
and pitching it forcefully. Solution selling
+ Treating insight selling as a tactic
is necessary, it’s just no longer sufficient
rather than a pursuit: Some sellers for sales success (see page 8 for more
think that if you share content and on this).
antagonize buyers you are employing
insight selling. Insight selling is not about
+ Lacking customization and customer
doing one thing or another, it is about you
focus: With a little effort, sellers can
providing value throughout the
create much deeper engagement with
entire sales process.
buyers. Take the time to demonstrate
understanding and tailor interactions
+ Not embracing the mindset of seller
uniquely for them.
as a change agent: If sellers are just
part of the status quo and are not
pushing buyers to step outside of the box, CONVINCE
they’re probably not selling anywhere near
their potential. Insight sellers must + Not convincing at all: Insight sellers
embrace their role of change agent and must be able to take a point of view,
push buyers out of their comfort zone. defend it convincingly, and persuade
others to believe.
+ Being arrogant or meek: Many buyers
report that sellers are pushing too far, + Conducting ill-timed needs discovery
too hard, and too fast. On the other end of versus presenting: Know when it is
the spectrum, a success killer is the quiet time to share a point of view and when to
seller who isn’t willing to challenge the listen. For example, if the buyer requested
thinking of buyers. You must find the and arranged the meeting, let them own
right balance. the floor first.

+ Sending information via email and + Making presentation gaffes: The list of
believing that’s insight selling: possible mistakes is long: bad story, bad
Buyers see this for what it is—a non- slides, too many slides, improper humor,
customized strategy that communicates etc. Most importantly, design your
the seller is not making an effort. All presentation to be interactive, and master
messages should be relevant, personalized, the material.
and focused on a strategic imperative
important to the individual buyer.

© RAIN Group | [Link] | 18

Your Guide to Insight Selling Success

+ Dismissing trust: The buyer’s trust CREATING THE INSIGHT

in the seller is essential. Without it, the ORGANIZATION
buyer perceives the risk of buying from
you as too high. + Expecting that everyone can be an
insight seller and not hiring for
COLLABORATE insight: Not everyone is destined to be
an insight seller. Assessing and hiring
+ Equating collaboration with candidates who have the necessary
consensus: Collaboration does not mean skills and attributes (see page 4 for the
getting absolutely everyone on the same 12 attributes of an insight seller) is critical
page, and it does not mean including for organizations that want it to become a
people who are tangential to the decision- part of the sales culture.
making process. Instead, engage the
primary buyers in needs discovery and + Lacking the tools and resources to
solution crafting. execute insight: It is not always possible
for every seller in a team to generate his
+ Being unwilling to involve the or her own ideas to expand buyer thinking
buyer: Working closely with senior, and success for the business. Circulate
highly-knowledgeable buyers can be good ideas among the team to ensure that
intimidating. Put in the effort and time every seller is armed with the best tools.
to increase your expertise and craft a
peer dynamic with the most senior + Not coaching for insight: Sales
decision makers. coaching too often focuses on the process
of a deal. Rarely do coaches give
+ Creating psychological ownership, encouragement, offer ideas, and provide
resources to make the seller more effective
then stealing it away: Sellers commonly
with insight selling.
don’t allow the buyer to take the credit for
ideas and thus don’t create ownership.
Instead of pointing out that you had the + Providing training that fails: If
same idea, simply say, “I agree.” insight selling is simply this quarter’s
training program, don’t expect traction.
To build effective insight sellers, company
+ Not taking control and guiding the
leaders should think of training less as
collaboration: Collaboration does not
an event and more as an ongoing priority
mean relinquishing control. It is
and initiative.
important to have the skill and gravitas to
prevent a buyer from strong-arming his or
Common mistakes and misconceptions hinder
her way out of a collaborative setting.
the ability of many to master insight selling. To
be successful, follow the lead of the winners—
+ Not being proactive: Buyers are
connect, convince, and collaborate—and avoid
disengaged when sellers don’t establish
these common pitfalls.
themselves as sources of insight in
collaboration-driven meetings.
Proactively invite collaboration—don’t
leave it to chance.

© RAIN Group | [Link] | 19

Your Guide to Insight Selling Success

TRANSFORM YOUR SALES TEAM

Sellers who harness the power of ideas don’t just sell the value of their offerings, they become
the value.

Following the tips outlined in this guide is a great start to becoming an insight seller.
Implementing insight selling, however, is fraught with challenges. Getting it done right is tricky.
But those who do reap the rewards.

Go forth and share your insights with buyers. Connect, convince, and collaborate during the
sales process and not only will you find yourself in the winner’s circle more often, you will also
maximize client loyalty and generate the most referrals.

TRANSFORM YOUR SALES TEAM INTO INSIGHT SELLERS

Insight Selling by RAIN Group, a highly customized two-day training program for sellers and sales
leaders, will teach your team exactly what they need to do to succeed with an insight-based approach.
They’ll learn how to create conversations with buyers on the premise of ideas and insights, maximize
relationship strength based on value, and more. See the next page for more information.

RESOURCES IN THIS GUIDE

WEBINARS
What It Takes to Sell with Insight
Become a Source of Insight for Buyers: How to Sell Ideas and Drive Demand
The Missing Link to Winning More Sales

PODCASTS
Buyers Want and Need Insight from Sellers
5 Steps for Collaborating with Buyers and Increasing Sales

ARTICLE
Generate More Leads with Existing Accounts through Value and Collaboration

TOOL
Convincing Story Framework

VIDEO
The Person As Distinct

© RAIN Group | [Link] | 20

Insight Selling by RAIN Group
How to Change the Conversation, Drive Demand, and Differentiate through Selling

PROGRAM OVERVIEW Buyers Want Your Insight

The landscape of buying and selling has changed more in recent years than it has in In our groundbreaking book, Insight
preceding decades. Buyers are more sophisticated and, thanks to the Internet, are awash Selling: Surprising Research on What Sales
in information and research. At the same time, executives are searching—often in vain— Winners Do Differently, we found that
for new ways to innovate, compete, and improve their success. the number one factor separating sellers
who win the sale from those who come
When sellers bring valuable insights and ideas to buyers, they strengthen relationships, in second-place is: Seller educated me
differentiate from competition, and win more sales. with new ideas or perspectives. In fact,
sales winners educate buyers with new
Insight Selling by RAIN Group teaches sellers how to create conversations based on ideas and perspectives 3x more often than
ideas, inspire with insights, and set themselves and their companies apart from the pack. second-place finishers.

LEARNING OBJECTIVES
In Insight Selling by RAIN Group, participants will learn how to:
+ Create conversations with buyers on the premise of ideas and insights
+ Tell a Convincing Story that intrigues buyers and shapes their thinking
+ Create insights by asking incisive, powerful questions
+ Identify buyers most likely to be receptive to new ideas, and position
ideas based on buyer preferences
+ Use the concept of cognitive reframing to open executives minds to
new ideas By RAIN Group Presidents and bestselling
authors Mike Schultz & John Doerr
+ Maximize relationship strength based on value

TOP 10 BENEFITS OF INSIGHT SELLING BY RAIN GROUP

Insight Selling by RAIN Group
1. Differentiate and set your company apart from the pack Online Training Program
2. Create new business opportunities that fill the pipeline Are you an individual looking to become
3. Tell a Convincing Story that intrigues and inspires buyers to act an insight seller or is your team spread
across a broad geography? Insight Selling
4. Understand personal strengths and challenges for applying insight selling
by RAIN Group online training will walk
5. Get to, and succeed with, senior executives you step-by-step through exactly what
6. Challenge buyers without being standoffish you need to do to make the transition
to an insight seller and achieve greater
7. Bring client-centric selling to a whole new level
sales success. Learn more at [Link]
8. Become an indispensable source of insight to buyers [Link]/insightsonline.
9. Sell on value and realize higher margins
10. Win more sales and grow existing accounts Contact Us
Phone: 508-405-0438
DELIVERY OPTIONS Website: [Link]
+ Tailored on-site, instructor-led programs Email: info@[Link]
+ Train-the-Trainer, Licensing
+ Blended learning: Online and on-site, instructor-led curriculum Locations
+ Online learning program Americas • EMEA • Asia-Pacific

© RAIN Group | [Link]

About RAIN Group

UNLEASH THE SALES POTENTIAL OF YOUR TEAM WITH RAIN GROUP

RAIN Group is a sales training, assessment, and performance improvement company that helps leading organizations improve sales
results. We’ve helped hundreds of thousands of salespeople, managers, and professionals in more than 34 countries increase their sales
significantly with our RAIN SellingSM methodology.

We can help you:

IMPLEMENT SALES TRAINING THAT DELIVERS IDENTIFY WHO CAN AND WILL SELL WITH
REAL RESULTS GREAT SUCCESS
RAIN Group’s sales training system inspires real change and Our assessments measure sales attributes and skills,
delivers real results that last. Our rigorous approach includes identifying the factors that really make a difference in sales
sales team evaluation, customized training programs, robust performance. Whether you’re looking to hire someone who
reinforcement, and coaching to help you and your team can and will sell, or looking to improve sales performance,
develop sales and negotiation skills, and maximize your results. we’ll help you build the most successful sales team.

GROW YOUR KEY ACCOUNTS IMPLEMENT WORLD-CLASS SALES

At most companies, there’s a huge, untapped opportunity to COACHING
add more value—and thus sell more—to existing accounts. We coach sellers, professionals, and leaders individually
We help our clients capitalize on these revenue growth and in groups to achieve the greatest and fastest increase in
opportunities. Whether it’s simply increasing cross-selling sales results. And we train and certify leaders and managers
and up-selling or implementing a major strategic account in our RAIN Sales Coaching system. Often, it’s RAIN Sales
management program, we can help. Coaching that truly unlocks the team’s potential, and keeps
them motivated to produce the best results consistently.

Find out more about how RAIN Group can help you unleash the sales potential of your team by visiting
[Link] or calling (508) 405-0438.

RAIN GROUP’S CLIENTS

LOCATIONS
AMERICAS • EMEA • ASIA-PACIFIC

CONNECT WITH US

© RAIN Group | [Link] | 22