“Pain-full” Discussions For Customer Executives


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An Executive Encounter

Sales Professional (SP): Thanks for agreeing to meet with me. I understand you spoke to Robert, a mutual friend.

Executive (Exec): Nice to meet you. Yes, Robert spoke highly of you and suggested I accept your invitation to meet.

SP: Well, I want to respect your time so I’ll get right to it. What I like to do when I meet with a C-level executive is to ask some questions to clarify your needs. As you know, we have many end-to-end solutions that solve numerous problems, but we like to diagnose before we prescribe.

Exec: Sounds painful. Are you a doctor?

SP: (Laughing) This won’t hurt, I promise. In your position as Chief Operating Officer, what are your biggest pain points?

Exec: Excuse me?

SP: You know, issues that keep you up at night: needs, problems, challenges — PAIN. I have a list of generic pain points that align with a Chief Operating Officer if you want me to list …

Exec: No, that’s not necessary. Why are you asking about my pain?

SP: Because we’ve been trained to probe for ‘needs’. It’s part of our sales methodology. You know – our motto is ‘no pain, no change’. Our company is expert at solving problems and we need to know what challenges and problems you will acknowledge. This is step one in our sales methodology, you know. Of course, latent pain is even better if I have a solution, but I’m getting ahead of myself.

Exec: You are a doctor, Dr. Doom N. Gloom. Just kidding. Yes, I had another sales person in here last week who asked me what my ‘wants’ were. When I asked him to clarify, he said ‘wants’ were more important to talk about than ‘needs’. I didn’t really understand what he meant.

SP: Oh yes, ‘wants’ are even better than ‘needs’ because they are greatly influenced by FUD factors.

Exec: What’s a FUD factor? Is that a new virus strain?

SP: You know, fear, uncertainty, and doubt.

Exec: Interesting. Will you excuse me? I’ve got to take this phone call.

Pain Doesn’t Get Executive Lips Flapping

Ouch! From a buy-side executive perspective, this conversation is painful. Unfortunately, many sales professionals have inextricably linked pain with solution selling — even selling at the executive level. While this approach might be effective at lower levels in the organization, it rarely works as you move up the executive ranks in your customer organization.

Put yourself in the shoes of the executive. What’s in it for them? Why would they want to answer probing questions about pain from a sales professional who knows little about their business? Nothing personal, but these kinds of conversations are reserved for business colleagues or business partners who have earned trusted advisor status.

I understand your dilemma as a sales professional. I even feel your pain. You want to get executive lips flapping about an issue that is important to them that happens to be solved by a solution that you offer. The problem is getting the executive lips flapping. They don’t tend to be talkative, especially with a sales person not adequately informed about their company. Asking a bunch of questions doesn’t work. Executives don’t like to be interviewed. Throwing a bunch of solutions against the wall to see if anything sticks is a low probability game. Whipping out a generic listing of pain points and assuming they apply is a certain death sentence.

You may have only one chance (and a few minutes) to make a favorable impression. Hope is not a strategy, and neither is pain.

Straight From The Horse’s Mouth

Recently, in order to validate my views on executive-level pain probes, I surveyed a network of fellow buy-side executives. I asked them two questions. The first question: How often do sales professionals probe for pain when meeting with you? Their answers included:

  • A lot. They almost seem robotic, brain-washed.
  • All the time, they all do it.
  • Over half the time. Very unconstructive and a complete waste of my time.
  • Many times. They even talk about a so-called ‘pain chain’!

The second question I asked my network of buy-side executives: Would you advise the sales professionals reading this blog to continue “selling pain” at the executive level?

  • Perhaps, but amp it up. They have to know A LOT about me to pull it off.
  • No, it doesn’t add value to me. I don’t do interviews and I don’t like negative people.
  • No, they need to come up with a different approach — something that sets them apart from the herd.
  • Never. Just focus on my company’s business priorities. Seems pretty simple to me.

Business PRIORITIES Instead of PAIN

There’s a better way for sales people to engage at the executive level. It’s a more positive, constructive way to gain credibility and obtain sponsorship for your solution. It’s not rocket science, but it does require research and preparation.

Keep positive and focus on the business priorities of executives, NOT PAIN! Business priorities, especially those recently announced, are a favorite subject for most executives. They are the strategies, initiatives, goals, and objectives that promote change which represents opportunities for your solutions. Business priorities move the needle for executives. By definition, they are the funded action plans appearing on the radar screen. Business priorities are unique to each company. And the best news is that they are frequently disclosed in public sources. You just need to know where to look and how to read between the lines.

Start a dialogue by demonstrating your knowledge of the executive’s business priorities. You have a limited time to converse with a customer executive. An executive engagement is a high-risk, high-return moment. Every word counts. You will either sustain a two-way conversation or send it into a deadly monologue spiral. Do you really think an executive is going to ‘open up’ and willingly talk about what keeps them up at night? As a former Fortune500 CFO, I rarely answered that question which was posed to me numerous times.

Oh sure, some business priorities implicitly address pain. But many business priorities directly support competitive market opportunities and advances in technology. Steer the focus to business priorities to set a positive, constructive tone.

Examples of Business Priorities

Let me give you a few examples of publicly-disclosed business priorities. Reliance Industries, India’s largest private sector company plans to invest $10 billion to $12 billion to expand in the U.S. market. Their “business priority” is to find local partners who could best help them support this growth.

NIKE, Inc. is planning to make significant capital expenditure investments ($500 million to $600 million) in the global Direct-to-Consumer business which consists primarily of the NIKE-branded retail store format. Their “business priority” is to accelerate time-to-market for this channel expansion.

And Walgreens is ramping direct sourcing resources and capabilities in the Far East. A new office was recently opened in Hong Kong. Their “business priority” is to build the private label business which carries a higher front-end gross margin.

The executives of these companies don’t dwell on pain, problems, and challenges. They are driven by business priorities which represent the best opportunities for your solutions.

Of course, if your target customer publicly acknowledges ‘pain’, go for it. This doesn’t happen often, but occasionally the ‘pain’ is too much to hide. Sprint represents a good example. As the 4G race tightens in the smartphone market, Sprint has struggled to accelerate the rollout of its Evo 4G phone. In a conference call in mid-2010 Sprint’s CEO, speaking to a shortage of phones to sell, publicly acknowledged, “The supply issue is a big deal for us.” Now there is a pain point to pursue with vigor!

Remember: Priorities, Not Pain

The next time you instinctively reach for the P-word when engaging an executive, pull out ‘Priorities’ instead of ‘Pain’ and see what happens. Got pain? No thanks. Got priorities? Let’s talk.

Republished with author's permission from original post.

Jack Dean
As co-founder of FASTpartners LLC, Jack brings extensive technology buying experience as a Fortune500 Chief Financial Officer to the B2B technology sales training industry.He has facilitated client-sponsored business acumen training for 15,000 B2B technology sellers representing 150 global technology companies.Participants in Jack’s business acumen training have produced directly-attributed revenue of over $1 billion (in the 3 months after training) and training engagement ROIs averaging 500%.


  1. I did a short video about these type of questions. Conversation vs. Interrogation.

    Buyers can feel manipulated and salespeople can get lost in their questions.

    I agree, better to start of with the Executive’s KPI’s. Then I like to run the Executives by a few mini User Stories to get them talking and see if they see themselves in these stories. If so, let them tell their story.

    Have a conversation vs. an interrogation.


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