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3 Prospecting Issues these should keep you up

Sleepless Salesperson

Many sales people – and some sales leaders – will admit they struggle to get access to senior decision makers within ‘Must Win Accounts’.

The Mindset and Skills to reach out effectively to these executives are often assumed to be in place, and sales reps often won’t bring it up as they don’t want their leaders to know they need help.

Sales organizations believe this skill is “magically” developed in-house by osmosis, or that they are already getting these skills by employing experienced sales people.

Based on 20+ years of field work and hundreds of client engagements, I have come to the conclusion that there are 3 Issues that sabotage your sales force’s new business prospecting efforts:

#1: Your messaging is 180 degrees backwards

You’ve hired some great sales people. Experienced sellers with proven track records, or energetic inside salespeople in their first or second job. And yet for some reason, they’re taking a long time to ramp. They aren’t able to get enough meetings with senior decision makers, so a lot of your opportunities and proposals don’t convert into wins.

Here’s why your sales people are wasting their time talking with people who aren’t Executive Decision Makers. Your messaging and value proposition is backwards, perhaps even broken.

Here’s how this plays out in most sales organizations.

What you do is put your salespeople through an on-boarding program – if they’re lucky.

The onboarding program is often headed up by product marketing who talk about ‘us’. Our products, our solutions, our target market, our value proposition. It sounds like this;

WE help companies to…

WE are the most effective/cost efficient/fast…

WE are the market leader…

STOP “weeweeing” on potential customers. They don’t like it!

Your company and salespeople are not the hero. The customer is. Your customer is looking for an expert, a guide. Rarely will true Decision Makers respond to this kind of message, it’s mostly the tire kickers with no authority to buy.

What you and your salespeople should be focused on is talking about THEM – your buyer, your customer, what trends and challenges impact them, how others like them have solved these challenges and achieved their goals. It’s not about your company, product, service or solution… it’s about them.

Most sales people have never done the job of the person they’re expected to sell to. They don’t know what a VP or a CEO’s job is, or what their buying motivations are.

And yet, you’re telling them to go prospect and sell to those people, armed with nothing more than internally focused product marketing information, an Ideal Customer Profile (ICP) and a value prop that’s all about you.

If they’re experienced sales people, you expect them to know how to write messages and prospect to senior executives. It’s kind of an unwritten rule that nobody asks about, isn’t it?

And if they’re new to sales? Well, you expect them to ‘figure it out’. Learn by osmosis.

Lack of a customer focused value proposition is one of the greatest inhibitors of prospecting success.

What you need to do is “be intentional” about this critical part of the sales cycle – teach them about your prospective customers first. Most sales organizations aren’t and don’t.

What concerns does a Senior Executive vs a Line of Business leader have? What’s a ‘day in their life’ look like? How are they measured, what are the trends impacting their market, what challenges do they face, how are they currently addressing those challenges? What opportunities could they be taking advantage of…but they’re not? They’re doing this, when they could or should be doing that.

When your salespeople really grasp and understand your customers, then tell them how your products, services or solution links back to your customers’ issues and helps them improve their business.

58% of sales opportunities end in

And then show and teach your salespeople “how” to communicate this in writing AND in conversation to decision making executives at your prospects.

Unfortunately, most companies never do this.
And that’s why time to ramp is so slow, sales cycles are long and why 58% of opportunities end in no decision or are lost.

Sales people are spending their precious prospecting and selling time, writing and talking about your company to mid-ranking managers who defend the status quo.

So, do your salespeople and yourself a favour.

Go beyond “drinking the kool aid” and only exposing your sellers to your product marketing information.

On board them with messaging created from your buyers’ perspective.

And arm them with the written and conversational mindset and skills to sell “beyond their pay grade.”

You’ll be glad you did. Transformational sales results will be achieved.

#2 Your salespeople are prospecting and selling too low

Your greatest threat to sales success isn’t your competition.

It’s the status quo.

Status quo is the internal inertia your sales people face with your potential clients. It’s the way potential customers are running and doing business today. Business as usual vs introducing a change (your offering).

Are your salespeople prospecting and talking to people who can say “yes”? The people who can mobilize internal resources and create or have access to budget?

According to The Chasm Group, 85% of budgets are already spoken for on existing initiatives

Too often sales people waste their time prospecting and trying to sell to mid-ranking executives who are “invested in the status quo, can’t say yes, but can say no.”

And, even if they are working with a mid-ranking exec who wants to drive change/improvements, the mid-ranking executive probably can’t push the deal up the chain of command.

This graphic summarizes the core motivations of functional and strategic executives and their ability to spend/buy.

Change & Growth

When I show this graphic to salespeople I get groans as they have an “aha” moment.

Many realize that they are wasting their lives – as they spend most of their time prospecting into and trying to sell to mid-ranking functional executives.

Quite simply, the motivations of the mid-ranking executive is to operationalize and execute – not to introduce change or buy (unless triggered/directed to by a senior executive).

95% of buyers are in status quo

If, as research shows, as much as 95% of buyers are in status quo and mid-ranking executives’ motivations are to execute/operationalize and not introduce new behaviour and process change (aka your offering) – then why do most sales leaders and their sellers focus their time and energy on such low probability activity? This shows up as lots of activity…but few opportunities in the pipeline.

What difference would it make to your business if your salespeople were prospecting and speaking to executives who are open to and interested in new ways of growing and running their business…and who create budgets?

In order to loosen the grip of the status quo, sales people need to prospect into people who are motivated to change, to impact top and bottom line – because that is what selling is – it’s changing from one state to another.

Who is motivated to make improvements to their business and open to change?

The executives of the company. The C-Suite’s role is to look for new ways of doing things that will give them a competitive edge.

This is where top sales performers start their engagements. The top down approach.

Here’s the proof of this approach.

If you’re a CEO or Sales Leader reading this, ask yourself this…

If you wanted to do business with another company, would you reach out to a mid-ranking executive with a Manager, Director or even a VP title?

The answer I get from most leaders is because they know that decisions to do ‘new’ and ‘different’ are made at the C-Suite level, and those decisions are made fast.

If that’s the case, then why are you letting your salespeople prospect into mid-ranking execs where they have low probability of success?

Research from SBI shows that as much as 58% of deals end in ‘no decision’. You’re wasting your salespeople’s lives and putting your company’s growth at risk if you allow them to prospect and sell too low.

#3 Your salespeople (and sales leader) have never been taught how to WRITE prospecting messages to C Level executives

How many of your salespeople can start a sales cycle with the CEO or another C Level executive? If you are an executive or sales leader reading this, think back in your own career.

Did anybody ever teach you how to WRITE a letter, email or LinkedIn Inmail to a CEO, President or C Level executive – that compelled them to begin a conversation with you?

I only ever get a few hands raised to that question…This is an ‘‘invisible elephant” in most companies I’ve ever spoken to or worked with.

Most sales people have never been taught how to write executive level prospecting emails, letters or LinkedIn Inmails…they are left to figure it out on their own.

Nor do they have the mindset or confidence to write and ‘go high.’ And yet, that’s where decisions to change are made – as executives are focused on new initiatives that drive growth or efficiencies.

The ability to write effective prospecting messages helps salespeople get appointments with the right people, at the right level at target accounts in minutes, hours and days…not weeks, months or never! Consistently.

And this delivers transformational increases in pipeline and sales results.

To learn more about Matt Conway’s methodology, visit his website at


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Eliot Burdett

CEO at Peak Sales Recruiting

Before Peak, Eliot spent more than 20 years building and leading companies, where he took the lead in recruiting and managing high performance sales teams. He co-founded Ventrada Systems (mobile applications) and GlobalX (e-commerce software). He was also Vice President of Sales for PointShot Wireless. Eliot received his B. Comm. from Carleton University and has been honored as a Top 40 Under 40 Award winner. He co-authored Sales Recruiting 2.0, How to Find Top Performing Sales People, Fast and provides regular insights on sales team management and hiring on the Peak Sales Recruiting Blog.