A Story Of Empathy — The Lost Art Of Selling?

Posted by Scott Santucci


In 1992, with my Marketing Management degree in hand, I went out in the market to find a sales job. At the time, I believed (and I still do) that you can’t really be the best B2B marketer unless you know how to sell first. One of the jobs I interviewed for was with a local dealer to sell fax machines (yes, it’s true . . . FAX machines). The VP of Sales interviewing me asked a simple question — what are the most important things to being a sales person?




Well, right out of school, I had no way of knowing. My only experience up until that point had been selling my neighbors on me mowing their lawn, and Cutco (that’s right, I sold that cutlery and still remember a lot of the rap). That guy told me something that has stuck with me my whole career. He said the single, most important thing to selling is “empathy” and he actually gave me Tom Peter’s book On selling. (For full disclosure, my first job — I sold industrial supplies, fasters, and chemicals to building maintenance shops).


Being a closet intellectual, I developed a passion for the art of selling. I’ve read and re-read practically every book published on the subject by authors like: Neil Rackham (SPIN Selling),  Zig Ziglar, Michael Bosworth (Solution Selling), Robert Miller and Stephan Hieman (Strategic Selling), and Rick Page (The Complex Sale).


I’ve also gone through several formal sales training courses: Power-base selling, Learning Tree’s Professional Selling Seminar, Solution Selling, and Customer Centric Selling and have applied all of those lessons with varying degrees of success in both individual contributor and executive leadership roles. What have I learned through my journey?


The single most important thing is, in fact, what I learned on my very first sales interview. What truly separates top sales people is in fact that innate ability to connect the dots with a buyer. Michael Bosworth talks about “eagle” sales people — basically the 20% of the sales force that performs no matter what. Over the past seven years (six with my own consulting company and one here at Forrester), I’ve spent a lot of time talking with those 20% to find out what can be done to unlock their performance. At any sales training event, you can easily pick out the top performers, and those are the people I speak with.


When I ask them how they sell, I get more or less the same answer; “Well, I just sell a vision — you know what I am talking about.” I do, but it’s a hard thing to describe to the rest of the organization.

They are talking about empathy.


Other words people use to describe in include: insight, knowledge, expertise. Whatever word you use, what we are talking about is the ability to:


  • REALLY understand the customer’s business pressures and organizational realities
  • Determine the root cause problem, not just treat symptoms
  • Help problem solve, not present
  • Frame out a concept in the language of that company and help communicate it to others
  • Organize complex realties (without overly simplifying them to where you lose credibility) into an actionable plan that customers feel is achievable
  • Navigate all of the impacted stakeholders involved in the purchase

There are few verticals as complex as the information technology industry and that complexity is only increasing.


  • Technology has reached the tipping point to where it’s something that business people understand and want — putting tremendous pressure on traditional IT organizations.
  • Funding models are changing creating “pass the hat” type of budgeting and allocation patterns — making buying much more of a collaborative process.
  • Systems are becoming much more intertwined with other systems — putting pressure on classical siloed operational modes and driving new management ecosystems
  • Business objectives are changing to the point where systems must be configured holistically, not just optimized to drive one goal (like reduce costs) — this creates a level of business and technology planning that outpaces most current program management models.

Perhaps the first step in providing buyer insight and empathy to our customers is to help highlight how big the gaps are. We recently interviewed 168 executives (55% from business, 45% in IT).

Here are some very interesting results, when we asked, “When you meet with a vendor sales person, in general how often are they prepared for the meeting in the following ways?" (% are for respondents who answered "usually"):


  • Knowledgeable about their company and products         88%
  • Knowledgeable about my industry        55%
  • Can relate to my role and responsibility in the organization    34%
  • Knowledgeable about my specific business      29%

This is what that copier and fax sales person was talking when he shared his point of view about “empathy.” Obviously, the big difference between selling a fax machine and a complex offering like an outsourcing service or an enterprise application is that number of people involved and all of the nuances that a sales person must be able to relate with.


This ability — to connect the dots — between an organizational issue, the points of view of all the impacted stakeholders, and the capabilities you bring to the table is what your top sales people are doing.

To help more of your sales people perform, good sales enablement programs concentrate on reducing the burden on sales by confronting the complexity their customers face head on. Many sales organizations are in the process right now of reinventing themselves to co-create value with their buyers. Market and support services can catalyze this transformation by shifting their focus to enabling the valuable conversations required in the trenches.


re: A Story Of Empathy — The Lost Art Of Selling?

Spot on, I have been involved with very good sales people and very poor sales people and the thing is they all beleive they are the best, however the poor ones are all about themselves and the good ones areall about the customer. Great wrighting thanks.

re: A Story Of Empathy — The Lost Art Of Selling?

Thanks again Alan - I definately agree with the sentiment that top performing sales people are completely focused on the customer.I want to be careful abit in my comments though. Our research mission at Forrester is not to make value judgements on sales people (they get enough of that already), but rather - turn the lens on the support infrastructure operating behind the sales force.I think the issue isn't about good or bad sales people - its about what those sales people are trained, prepared, managed, and measured to do.This is my way of agreeing with you without violating one of my primary directives: don't judge sales people.

re: A Story Of Empathy — The Lost Art Of Selling?

Sorry Writing !!!!

re: A Story Of Empathy — The Lost Art Of Selling?

WOW, this is a very refreshing view of sales, I agree that many critism's are levied at sales people when they are actually sent out ill prepared. ie. expectations are High however standards of preparation are Low. Come on employers its time to waken up to inward investment after all you have employed a huge overhead and without the correct preparation you have an under utilised resource in the field.....PS. Im available at a small fee! lol.

re: A Story Of Empathy — The Lost Art Of Selling?

Knowing and understanding the business you are selling to must surely be one of the most important part of any sales process. With this in mind it surprises me that less than a third of executives you questioned felt that the people selling to them really knew their business.

re: A Story Of Empathy — The Lost Art Of Selling?

Hi Rich, I agree with you - understanding a clients business and their problems is very important.Personally, I think the lower hanging fruit is with understanding roles. All things being equal - the trait most sales people understand is relationship building. While a sales person is generally very good about aligning to a given executives personal goals - its a lot harder to understand tehir professional motivations. Having not been a CIO for example - its hard to really comprehend how those executives are measured (formally and informally) so a sales person can align with their motivations.Understanding a business as complex as J&J is signifcantly more difficult than helping sales get comfortable about the roles they sell into.Thus, I think the sequence of events here is: 1) determine the set or roles involved in making purchase decisions 2) understanding each of their own motivations 3) how they relate to each other and 4) how you help them. This will provide the required base to eventaully tackle the business problem part.