Insight Challenge eBook

1The Insight ChallengeThe First Installment of the Charlie Chronicles

2013 DSG Consulting. All Rights Reserved.

2The Charlie Chronicles: The Insight Challenge

Meet Charlie.

Charlie Cooper is a seasoned sales rep at Centrift Systems,

Inc. and is just arriving at his annual sales conference. Hes a

40-something whos been with the company for 10 years and

made his quota nearly every year. I wish I could skip the pep talk

this morning and get an early tee time with the guys, he thinks.

This mood reveals that, while Charlie has had success in the past,

hes been on auto-pilot for the last several years. Hes relied

on established relationships, conventional approaches, and his

power of persuasion to make his numbers each quarter. This has

been okay for Charlie but not ideal for Centrift, as Charlie targets

departmental levels in the existing base instead of pursuing new

and larger opportunities. And, if Charlie is honest, especially as

he looks at his pipeline for the next year, he would realize that its

been harder and harder to hit his numbers. In fact, hes waiting

for an e-mail from his biggest client to confirm he hit his numbers

for Q4 as everyone sits down for the keynote from the EVP of

Sales, Paul Stanton.

Living in a Virtual World(about to check phone for info on his big deal)

Top Performer(but on auto-pilot)

Charlie

Q4 Pipeline


Hey Charlie, his buddies say as he finds his

usual table of friends, did you get any word from

George about the contract renewal?

Thanks for asking, man. I was At that

moment his phone buzzes with a new e-mail. Dear

Charlie, etc., etcThanks for coming by recently, etc.,

etcI know weve been tight for many yearsbut Im

sorry to tell you, etc., etc.Please touch base with

me next year, etc., etc..

Holy #$%&! Charlie says. What? his

buddy asks.

I just lost my biggest client. Mansorry bro! Just as Charlie starts to

explain the e-mail, Charlies bosss boss begins to

speak so he does his best to keep his cool.


Im proud to be the Sales Leader of Centrift, Paul starts out, a company with one of the longest

histories in the industry. Weve enjoyed many years of steady growth. But, as many of you have sensed,

our competition has intensified, our margins are tighter, and our products are in jeopardy of becoming

commodities. So it is time to innovate and seize this opportunity. Charlie shifts in his chair a bit. This isnt

the kind of tone he is used to at these conferences.

Paul continues, The game has changed. If we want growth we must sell higher in our accounts; we

must sell earlier in buying cycles; we must lead with insight, not functions and features. Charlie is really

lost now. But, he notices Paul really has everyones attention. You can hear a pin drop in the meeting room.

Sell Higher

Engage Earlier

Lead with InsightHere we go again... I'm glad

I'm retiring

I wonder if my luggage arrived


So what do I mean by this? Paul says as he opens up a few slides. First, you must understand the

market better. There are drivers, trends, and pressures that present great pains and opportunities for top-

level executives. Second, you must understand your audience much better. We will be challenging each one

of you to reach much higher in the organization and know the buyer personas like the back of your hand.

Buying cycles typically end up in the hands of C-level executives, LOB leaders, and other stakeholders. So,

with those two components,

first, market knowledge and second, customer knowledge,

you will be well on your way to leading with Insight. There was that word again! Charlie leans over to his buddies now with a look like, What the heck is going

on here? They just shrug back and look as bewildered as Charlie.


What is Insight? Paul asks rhetorically. First of all, executives do not want to hear that your

product is groundbreaking or see 50 slides on the inner workings of what you are selling. They are looking

for engaging conversations that are relevant to their world, their business, their competitors, their markets,

etc. Executives don't want to be asked what's keeping them up at night. How should they look at those problems? Which opportunities should they pursue? Which risks should they avoid? I read a Harvard

Business Review article that put it

this way: Rather than

finding out how your

clients executives

currently view the

problem, determine

how they should view

it. Charlie was now

mentally going through

his roster of top customers.

They are too low-level to

even think about a

conversation like this,

he thinks to himself.

Traditional solution selling is

based on the premise

that salespeople should lead

with open-ended

questions designed to surfa

ce recognized customer

needs. Insight-based selling

rests on the belief that

salespeople must lead with d

isruptive ideas that will

make customers aware of un

known needs.

July - August

2012


I know we have a big agenda today. So let

me net it out for you with a practical checklist as

you generate new insights for top-level executives.

A good insight should: (1) be verifiable and factual

(executives appreciate specifics), (2) challenge

the current mindset or approach that executive is

employing or considering, (3) evoke certain emotions

from the executive (skepticism, curiosity, disbelief),

and (4) elicit a response like, isnt that a problem

that I should be addressing? Paul pauses and goes

over each one as the still-subdued crowd looks on

and calculates what it would mean for their book of

business. Our new CMO, Laura Oliver, has a very

detailed roadmap to take us forward. After the break,

she will go deeper into this topic. I trust our strategy

for next year will become a part of our new culture.

With her help, I know we will be hearing great stories

from the field.

Verifiable?

Challenging?

Emotional Connection?

Elicits a Response?

Insight Checklist


Charlie and his buddies sit frozen through the rest of Pauls segment. At the break, Charlie jumps out

of his chair and makes a beeline for Paul (VP of Sales). Charlie has known Paul for 10 years, so he feels like he

can be direct with him. Paul, whats going on here?! Charlie asks. I know my customers, and they buy a

relationship with me, not whatever-you-were talking-about up there.

Dont worry, Charlie! Paul responds. You are in good hands with Laura. Shes a true sales enabler

and wont just dump a bunch of marketing-speak on you. I specifically asked her to invite you to her

upcoming sales messaging workshop so you could be a part of her core team.

Paul waits as Charlie stands there tongue-tied.

Charlie is thinking about how he just missed

quota for the first time in 10 years and

his pipeline isnt that great either.

Maybe this is an opportunity?

Okay, Paul. Ill give you the benefit

of the doubt. But, if I dont

Good, Charlie! Paul interrupts. I knew

I could count on you. Ive got to run. As Paul walks

away, Charlie shouts out one final question.

Hey Paul, what the heck is a sales messaging workshop?

What have I agreed to?


Meet Laura.

Laura Oliver comes with a strong resume from multiple past roles,

including Centrifts competitors. The last CMO only lasted 11 months before

they fired him. She knows that comes with the territory. Yeah,

she has some things to prove here and shes used to a challenge.

Laura knows how to bring the right players to the table and

facilitate good alignment. Shes a change agent, a game

changer, aOh! The last of the attendees have arrived at her first

Sales Messaging Workshop, so its time to turn it on.

She starts her opening session by saying, Will

we keep relying on selling more and more products for

growth? As our margins decrease, I know many are

forced to sell more and more just to maintain the

earnings you had the previous year. We will not

sustain our business that way. The game has changed. We want

exponential growth. And if we want exponential growth, we must capture the

value of solving higher level problemsproblems faced by the top levels of a

customer organization.

Change Agent(ready to tackle challenges)

Laura

Engaging(initiates great dialogue)


Im sorry, Laura! Charlie interjects. Im confused. Im starting to get what you want, but

definitely not how. Laura doesnt appreciate being called out so early in the process, but decides to

use the objection to her advantage instead of getting defensive. Yes, Charlie. Tell me if this helps. She

searches quickly and presents a slide. Insight is like a meal you might make in your kitchen. And like all

good meals, you need a recipe book to knowhow to make it. So over the next few days we are going to make that recipe book. Thats why we have brought

together our best thinkers and leaders across sales, marketing, and products to capture their insights. We

have also brought in outside resources.


At this point Laura (CMO) introduces Ben, the sharp sales messaging consultant shed worked with

in several previous sales enablement programs. Ben and Laura have great synergy. Ben drives the process

and facilitates the collaboration. Laura maintains good sponsorship for the project and challenges the

team to create better than me-too messaging. With your help, Ben will be creating our recipe book or

playbook that will include conversation-ready content in 3 core areas:

What to Know (before the conversation), What to Say (during the conversation), What to Show (during the conversation).

How does that sit with you, Charlie? Would that

be of value to you as you prepare for meetings?

Well, Charlie says, considering the

fact that I wing it half the time, I think this

might help a bit! Everyone laughs as Charlie

lightens the mood with a little self-

deprecating humor.

Ben

Drives the Process(facilitating collaboration)

Know

Say

Show


Thanks, Charlie! Listen everyone; let me drive home a previous point about conversation ready.

Ben says. We are going to avoid the trap of building a playbook focused on one-way communication.

While playbooks should be thorough enough to provide adequate preparation, their purpose is not to

rehearse a monologue. Rather, reps can use them to review the content shortly before the meeting

to get ready for an engaging dialogue between a sales rep and an executive. Its not a monologue. Its

a dialogue. Its not a pitch. Its a process. Its not a presentation. Its a conversation. We will include an actual conversation plan template as one way to do this. (Ben shows an example.) Reps can

use the conversation plan to tailor messages, questions, and materials going into the customer meeting.

Conversation Plan Name:

Key Trends Why Change? Why Now? Why Centrift? Next Steps

Here's one of the practical tools you can use


So Ben leads the team over the next few days building, arguing, and collaborating. Sometimes the

group is as quiet as the public library. Other times it is like a WWF cage match with participants debating key issues. Its important for Laura to get a quick win early on in her new role at Centrift, so she wants to keep things positive. During breaks, she coaches Ben to facilitate in a way that allows good

debate without letting any particular person dominate or squelch new ideas. They get through the What

to Know section by identifying several key market trends and some key insights around them (thanks to

some key marketing leaders who attended). The customer-facing sales people give good case studies that

help provide the What to Say content that is tailored directly to the key audience profiles they identify.

Then they go to the What to Show section. Everyone quickly

grabs their favorite slide decks and start to

ask for the projector cable.

Hold on, everyone! Laura interjects.

I had something else in mind.

HI-YA


During the last few years, Ben has been developing an approach that uses a whiteboard vs.

Powerpoint to drive a conversation. It quickly establishes the meeting as a two-way dialogue as people

stand up, move around, and craft a meaningful dialogue. This puts an end to a conventional one-way

show and tell. The whiteboard is used to provide a framework or a model for the executive;

problems are shown and solved through a picture. The whiteboard makes Charlie think of a classroom, but he quickly sees how this tool brings an ingenuity and originality to executive conversations

that his conversations often lack. So Ben, Ill let you get everyone started.

Thanks, Laura! Everyone stand up and go to your assigned whiteboard as we start to brainstorm

about what kinds of models, pictures, etc., will capture common problems. Our models need to be

simple, compelling, and present enough flexibility for your customers to adapt them to their specific

environment. Here are some basic ideas Ive collected from over the years.

vs.Engaged Asleep

Slide 631

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Step 10 Step 11 Step 12 Step 13 Step 14

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blah blabity blahblah blah blah blabity blahblah blah blah blabity blah blahblah blah

Process from slide 645

blah blabity blahblah blah blah blabi-ty blahblah blah blah blabity blah


It is quite amusing to watch PowerPoint button-

pushers try to become the DaVincis of sales. There are

models, stick figures, and bullet points. People trade

markers and try to find a central visual framework. Laura

and Charlie grab 10 minutes in the back and study a

few kernels from the top 3 groups and start doodling

on Lauras pad. Okay, everyone, lets bring things back

together, Ben says. Laura and I have seen some good

things and have some ideas of our own. Laura then takes

center stage. She explains what she calls the customer

dilemma and how that should drive the whiteboard

model. She then does a quick role play, with Ben playing

the customer. The whole group, including Charlie, sits

there and nods several times as they reflect on real life

situations that seemed to relate.

This could really change the game. Everyone is impressed with Ben and Lauras ability to synthesize and

uplift the teams ideas.

Dilemma


Things are really coming together now. By the last day, they have a good timeline in place to refine

the content and push it out in the field. After all this hard work, Charlie pushes back his chair and thinks

back over the last few months. At the beginning, he was beyond skeptical of this new approach. But now,

by utilizing the playbook to prepare for the conversation, Charlie has confidence in his ability to communicate the story and ask the right questions. He feels prepared to offer a few compelling insights

and navigate the conversation. But he has one lingering concern: Will he be able to turn his pipeline

around? Only time will tell.

I got this.

Then Now


Just as he is packing up to head out, his phone

buzzes again. Oh no! He thought. I cant handle

another lost deal by e-mail! It is an e-mail from

an executive assistant from a new prospect. He

nervously opens the e-mail and starts reading. Dear

Charlieweve received your many e-mails and voice

mailsJim has 30 minutes next Tuesday if you are

still interestedplease let me know Wow! He cant

believe he won that meeting. Now it is time to pull out that conversation plan and get ready!


Meet Jim.

Meet Jim Minkens, the SVP at Data Goldmine Inc,

a data integration company in Charlies territory. Jim

is overwhelmed. Hes new to this job, but a veteran at

the company. The CEO has charged him with ambitious

objectives to innovate, develop, and commercialize new

sources of revenue for the company. But, he is finding

the companys technology consistently presents road

blocks to accomplishing the task. When Jims assistant

notifies him that Charlie Cooper from Centrift has

arrived, he is less than enthusiastic.

Seriously?! Did I agree to that appointment?

Yes, you did, his assistant reminds him.

Jim fires back, I dont have time for a meeting

with some sales guy wanting to lock me into an annual

contract. Send him in... but call me in five minutes so I

can get out of it.

Is it Friday yet?

Jim

Overwhelmed(needs constant stream of caffeine)


Now, the rubber meets the road. Charlie has his first meeting since the creation of the playbook.

Hes equipped, but nervous. As he waits, he reviews the last of his notes and research about Jims company

and their key challenges. Jim comes out and greets Charlie. They walk briskly into Jims office, and Jim goes

to what he affectionately refers to as his PowerPoint chaira chair positioned just right for him to read

emails while a sales person shows endless PowerPoint slides.

But then Jim notices that Charlie doesnt appear to even have a laptop with him? He doesnt pull

out product specs? He doesnt carry a stack of promotional brochures? Instead, he walks over to the

whiteboard and asks Jim if he can draw on it. I find its helpful if we can both visualize what were talking

about. Jim sits, a bit stunned at first, as Charlie shows a genuine understanding of his situation. This isnt a

pitchits a conversation. What a pleasant surprise! An image starts to take shape on the whiteboard that summarizes Jims predicament in a manner clearer than Jim has ever been able to articulate it. As

Charlie and Jim begin to discuss solutions, the assistant rings Jim to bring the meeting to an end.

Interesting!


No, Im fine. . . Charlie and I have more to talk about. Jim stands up and takes the marker and

adapts the model to take it to the next level. Charlie listens and makes a few suggestions based on Jims

additions. Hes very careful not to let the conversation descend to pricing, features, and functions (things

that would be a sales pitch more than a provocation). Time runs out, and Jims next appointment arrives.

Jim cant believe how much they have accomplished in 30 minutes-- he would have actually paid for the insight Charlie gave him. So, Charlie, where do we go from here? What are our next steps? Normally this is when Charlie would talk dollars. But, Charlie doesnt try to make a speedy sale to Jim

thats not the objective. His objective is for Jim to become his sponsor.

Here's how I see it

I've got him hooked


Sponsorship is the purpose of a meeting like this one

between Charlie and Jim. And gaining sponsorship was one

of the key components of the sales playbook. An executives

sponsorship gives Charlie access and opportunity to focus on

building a business case, developing a solution recommendation,

and gaining internal support for the approach. If marketing leaders

like Laura are successful, reps like Charlie increase their confidence

in (1) delivering the right messages, (2) effectively leading

executive conversations, and (3) leveraging those conversations

into executive sponsorship. Sure, Charlie says. Let me paint

a picture for you. Then Charlie lays out a series of action items

for what sponsorship will mean for Jim for the next 90 days. Jim

asks some questions, offers details about his team, and sets some

milestones for the next meeting.

Jim doesnt need anything more to see the value in what

Centrift provides and offers to sponsor Charlie for meetings with

executives throughout the organization. Jim instructs his assistant

to find another time to meet and Charlie says hed be happy to

continue the conversation. Charlie leaves more encouraged than ever before.

This is going to be great!


Later, Jim continues to ponder the meeting. Fortunately, his whiteboard is still full of the insights

they discussed. He calls in colleagues, including some Senior VPs, to take a look at the whiteboard. It starts to clarify some strategic issues within the division and beyond. Meanwhile, Charlie reaches out to

the various stakeholders that Jim identified and begins to build the right solution approach. At each point,

Charlie goes back to Laura and her team for resources, tools, etc., to help him stay sales ready. Then, after

many milestones have been reached, Jim signs a multi-year deal with Charliehis biggest deal ever!

Now I get it!

I never throught about it that way


With each conversation, Charlie prepares with

his playbook and continues to improve. Hes learned

that preparation is the crux of the executive meeting.

Most salespeople cannot improvise an entire sales

conversation that delivers valuable insight and expect

stellar results.

He reflects back on the realities of his past 10

years with Centrift. Its taken a while, but hes learned

a critical lesson: while staff and mid-level management

audiences are not to be neglected, buying cycles typically end up in the hands of top-level executives. When salespeople like Charlie seek an audience with the right executives early in the buying

process, the trajectory of the opportunity can quickly

shift in the right direction. And those executives need

Insight. Leading with insight means bringing in fresh

ideas and supplying new approvals to change the way

the customer thinks about their business.

CXO


Fast Forward To Next Years Sales Conference

Paul Stanton, the EVP of Sales, is gleaming in the front row as his CEO gives the keynote speech.

Centrift is on a new trajectory with a record-breaking 15% growth to back it up. To get there, they needed the

decisive, strategic moves he made. One of those key decisions was to partner with Laura. Its easy for sales

leaders to trivialize the value of their marketing peers. Paul embraced it and made a powerful ally in Laura.

Laura looks down at her phone to see a text message from Paul saying, Congratulations! You are

the sales enabler I knew you could be. Laura smiles back and checks her calendar for next week. Laura is

currently in high demand as a speaker on how to enable sales teams. Shes now outlasted the last CMO and is

a vital part of the executive team.

Great year, everyone!

Paul

Laura

Charlie


Charlies phone buzzes too, and he looks

down. Hes finally gotten over his anxiety every time

an e-mail comes in. He then looks over at Laura to

give her a nod as well. Laura and Charlie have more

training sessions planned with new hires to get

them acquainted with the updated playbook. As he

glances down at next years pipeline, one thing is

for sure: he doesnt miss the days of relationship-

focused, low-level sales meetings.

Accounts Opportunities

SearchPipeline

LeadsContacts

Your Pipeline App

23


And what about Jim? Hes in his office conducting a reference call for Centrift. It really all started

with a meeting I had with Charlie, Jim says, Charlie didnt sell me products. Charlie didnt interrogate me

with questions. Charlie brought insight. By the way, Jim is now quite a hero internally, and he is talked up quite a bit in meetings across

his organization. Jims efforts resulted in a major initiative, helping Data Goldmine speed innovation and

increase revenue. Jim was recently promoted to a higher executive position within his company and is

respected as a change agent who is vital to the organizations future. He knows he has Charlie to thank.

The End.

Thanks, Charlie!


Are you like Charlie?Titles: Senior Sales Rep, Enterprise Sales Rep, Account

Executive, Account Manager

Objectives:

Expand his book of business, reach higher into existing

accounts, create relationships with C-Level executives

who can sponsor larger, enterprise deals

Challenges: Relies too heavily on a relationship sell, tougher

expectations from his Sales Leader, skepticism that his

new approaches will work

Living in a Virtual World(about to check phone for info on his big deal)

Top Performer(but on auto-pilot)

Charlie

Q4 Pipeline


Insight: Sales reps face a difficult reality. Business as usual is now not so predictablehaving a good product and

moving it out the door is no longer a given. Buying decisions are being made based on perceived value. If

competing on price, the sales reps product becomes just a commoditythat wont sustain business for long.

The rep is the one who can actually provide the added value. By moving from product and features selling to

insight selling, its possible to grow a sales pipeline even in difficult times.

Just as Charlie learned, the conversation that goes with insight selling usually occurs at high levels in a

company. Even if a sales rep lacks a sales enabler like Laura, it is possible to use the concepts Charlie learned

to prepare for higher level sales meetings.

Heres to the guy who can always get me tickets to the

game!

Jack, Charlies golf buddy and fellow salesman

I wish I could work so little and make as much as you!

Julie, 2nd year sales rep

Hey Charlie! If you beat my numbers next year again, Im going to kick your #$@!

Bob, Senior Sales Rep for 15 years with Centrift


Are you like Laura?Titles: CMO, VP of Marketing, VP of Products/Solutions, VP of

Field Marketing, VP of Product Marketing

Objectives:

Provide sales ready tools and resources to the field,

create solutions suites that can integrate both new and

existing offerings

Challenges: Tension between sales and marketing organizations,

existing documentation and insight is scattered across

too many organizational silos, limited bandwidth to get

it all done

Change Agent(ready to tackle challenges)

Laura

Engaging(initiates great dialogue)


Insight: The end game for marketing executives like Laura is to shift the entire organization from their existing comfort

zones to the types of conversations that align with the marketing strategy, connect to current marketing

campaigns, and create sales results. Charlie is proof that its worth the effort.

Keeping the focus on the outcome of different types of selling conversations will help marketing focus on

building the right content and tools that will enable the field and partners with practical support. Laura made

sure Charlie and the rest of the team understood that gaining executive sponsorship is critical in the sales

process.

To the first Female President of the United States!

Teresa, Brand Manager

I dont know how you keep all those sticky notes on your desk... But, Im sure one of them has our

next breakthrough!

Phyllis, Product Marketing

You inspired me to read my Kindle more than I play Call of Duty.

Craig, Communications Manager


Are you like Paul?Titles: EVP of Sales, Enterprise Sales Leader, Divisional Leader

Objectives:

Set overall vision and direction, design and deploy teams, create

alignment between sales and marketing organizations, bring in

the revenue

Challenges: 20% of team producing 80% of results, new acquisitions are

difficult to integrate into legacy teams, faster time to results for

new products and solutions

How can I inspire my

team?

Paul

aka EVP of Sales, Enterprise Sales Leader,

or Divisional Leader


Insight: Top executives feel pressure from both inside and outside the organization to make changes with solid ROI.

Unfortunately, those pressures are often not aligned toward the same objectives. Strategies are set that

promise growth, but the very people charged with implementing them may not be equipped to deliver. The

board room is filled with What to do, but the sales team increasingly needs new tools to carry out

the How.

Encouraging sales and marketing executives to become sales enablers is a great step toward getting the

sales team to implement the companys growth strategies. Thats not to say the process is easy. It requires

support from all levels of the organization. But, Paul provides a great example of how vital executive support

is in executing change in the field.

Hey Paul thanks for not firing me this year... No. Seriously. [gulp]

Thanks for not firing me

Jack, Northeast Sales Manager

To Paul! He could sell a moon rock to Neil Armstrong. He could sell ice

to an Eskimo. He could sell Shut up Phil! You suck up.

Phil (with help from the rest of the Sales Managers)

Ive been Pauls admin for 7 years, and one of these days Ill get him

to slow down.

Paula, Executive Assistant


Coming Soon to the Charlie Chronicles...

The Virtual Watercooler

Watch Charlie learn about mobile tools and the virtual sales community.

The Whiteboard Experience

Follow Charlie as he perfects the use of whiteboarding in his conversations.

The Challenger Sale

See Charlie realize that the Challenger Sale is great, but still not enough.