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I Asked 74 Sales Leaders For Their Best Sales Advice. Here’s What I Learned.

Chris Orlob

February 1st, 2017

Sales Advice From Top Sales Leaders

My brain was spinning.

I had to take a walk around my neighborhood just to organize my thoughts.

Having read most of the recommended sales books out there, I thought I had learned just about all there was to learn about B2B sales.

How wrong can one guy be?

I had been tasked with getting in touch with the world’s most prominent B2B sales practitioners to ask each one of them a simple question:

“What’s your most valuable secret of conducting effective sales conversations?”

The goal was to carefully document all of their answers and turn the whole thing into a free online guide as a way of giving back to the profession we at Gong love so much.

I expected to hear some of the same advice I’d heard so many times in reading all of the sales books I could get my hands on.

But as I flipped through these world-class sales leader’s responses as they came in like a flood through the Google Form I had setup, my paradigm continually shifted.

I had no idea there was so much I still didn’t know about sales.

Here are the most surprising ideas, themes, and concepts I was exposed to in organizing this project.

95% of Sales Demos are Done Ineffectively (Plus, The Right Way to Do Them)

During the first two years of my sales career, my “demo strategy” was to

  1. present my demos in the most logical functional order, and
  2. show the prospect each of the most valuable aspects of my solution to build value and justify price.

I wanted to give some background functionality so that the buyer had context when we got to the most valuable parts of the demo.

And I’m not alone in this approach.

Now that I’ve spent the last 18 months of my career on the purchasing end of sales interactions, I can confirm 9/10 software demos are conducted in this manner.

Peter Cohan – author of the book Great Demo! and founder of The Second Derivative explains why this is an approach that seems intuitive, but actively pushes your buyers aways from saying “Yes.”

Peter suggests “turning your demo upside down,” or presenting the “last thing first” (the most valuable part that you were previously “building up” to).

It’s similar to reading through a direct response ad, or a news article.

You start by skimming headlines, and when something catches your interest, you’re compelled to dive into the article to fill in the details.

Demos work the same way.

If you start with showing the most valuable screen first to your buyer, it will wrack their brain–in a good way.

They’ll start to go… “Whoa…  back up for a second. How did we get here? How does it do this??”

And now when you explain the context and backstory, they are incredibly attentive.

When you go the traditional demo pathway and start with the leading-up-to-context and end with the valuable features, they are mentally checked out by the time you get to what you were “building up to.”

You’ve lost them.

Sales Methodologies are Being Reorganized

I’m sure it’s not news to you that everyone in sales these days recommends “aligning your sales methodology with the buyer’s journey.”

Most everyone knows that by now.

But most of us have only paid lip-service to that idea.

We haven’t actually rearranged our processes, methodologies, and even vocabulary to lead the buyer through a complex purchase (as opposed to leading ourselves through a complex sale, which is what we’ve all been doing).

Garin Hess, CEO of Consensus said it best in his submission:

“We don’t need anymore sales acceleration technology. What we need is buying acceleration technology. There’s no such thing as a complex sale; only a complex purchase.”

That piece solidified a change in my thinking.

While I had long-advocated aligning sales with the buyer’s journey, I had still been focusing my own skills on increasing my ability to sell and persuade, rather than skills that enable my buyers to purchase more easily and intelligently.

What’s the difference at a tactical level?

When you’re focused on making something easy to sell, you load up your sales and marketing communication with benefits and your strongest selling arguments.

While these seem to address your buyers needs and values on the surface, buyers actually recoil from this type of communication.

By contrast, when you’ve focused your skills on making your product easy to buy, your communication becomes “There are a thousand-and-one solutions in our category that you have to sift through. Here’s the exact problem, situation, and type of person who our solution is tailored to, and here’s the results those people can expect.

In a word: Positioning.

When you modify your approach from easy-to-sell to easy-to-buy (helping buyers sort which technologies are best for certain situations, and how yours fits into that landscape), buyers reward you with their purchase.

Ironically, easy to buy translates into easier selling.

An Element of Science Is Being Introduced to the Sales Conversation


That’s how Mark Kosoglow, VP of Sales at Outreach.io started our first call together.

And it turns out the reason he did that is less because he’s an outgoing, charismatic sales leader and more due to the fact that he’s a methodical sales scientist.

In Mark’s contribution to the project, he discusses brain science, and how to conduct your sales conversations in ways that take advantage of how the human brain is naturally wired.

The amygdala (the most primitive part of our brain) is wired to help us 1) survive and 2) replicate.

When it identifies predictable patterns in our environment, your amygdala tunes the rest of your brain out. It concludes that things are both safe, and that there are no opportunities to remain alert to.

So when every single sales rep begins their conference call with “Hi, this is Chris from Gong,” buyers begin the call with a “passive brain” which eventually tunes out.

Starting calls in an unpredictable (but non-threatening) manner like Mark did commands attention and creates the impression that this is a call worthy of full engagement.

Having Coffee with 74 of the World’s Greatest B2B Sales Practitioners

What if you could sit down for coffee with each of the world’s top 74 B2B sales practitioners and ask…

“What’s the best advice you have when it comes to crafting winning sales conversations?”

I don’t have a crystal ball, but I imagine your win-rates would “hockey stick.”

It’s too bad these sales leaders can be so difficult to get in touch with — let alone have the time to sit down with you one-on-one.

But, I can give you the next-best thing.

The Ultimate Guide to Winning Sales Conversations has just been published for free, without having to fill out a registration form.

This is the project I was telling you about.

74 of the world’s top B2B sales leaders, practitioners, and thought leaders each gave their own angle on how to conduct highly effective B2B sales conversations.

From making better prospecting calls, to asking paradigm-shifting questions, to presenting earth-shattering demos…

It’s finally been made free, and at your fingertips.

If you want to hear what the other 71 sales gurus have to say about winning sales conversations, download the free e-book here, and let me know what you think on Twitter @Gong_io

This is a sponsored guest post from a Sales Hacker partner.

About the author

Chris Orlob

Chris Orlob is Senior Director of Product Marketing at Gong.io. - the #1 conversation intelligence platform for B2B sales teams. Gong helps you convert more of your pipeline into revenue by shining the light on your sales conversations. It records, transcribes, and analyzes every sales call so you can drive sales effectiveness, figure out what’s working and what’s not, and ramp new hires faster.

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