The best approach for an executive sales conversation

executive sales

The conversation

During one of the member coaching hours of my professional development program, someone asked me how to improve the way to have conversations with executive customers.

I recalled a common situation that occurred when I was a technology executive and sales people would bring me into their clients as the “visiting dignitary”.

I would have a conversation, and the sales people would be frantically taking notes about everything the customer said.

We’d leave and they’d say “Wow, how do you DO that?” You got so much valuable information from the customer, and at the same time you make him feel so important. How did you DO that?”

So I thought I would put my magic (actually, not so magic) formula into a blog, as was requested by the member on the call. You’ll see this sort of approach in many sales training programs. But this simple conversation flow that I’ll share here works really well.

1. Stop selling

If you want to have a great sales conversation, stop selling. You should never be aggressively selling. Think of what it feels like when someone is trying to convince you of something.

It doesn’t feel good. So taking the role of convincer is not going to be very effective with your customer.

2. Start actually caring

I would always try to go in to one of these executive sales situations by actually caring about how the customer was doing.

That lead me to ask the following 4 questions.

1. What are you trying to accomplish?

They would tell me about their business and what they were doing.

2. How is it going?

Sometimes they would say a lot, but sometimes they would only say, it’s all going great.

No one, in any business, is in a situation where it’s ever ALL going great. If that was the case, their job wouldn’t be necessary. So next I would ask…

3. What is the biggest issue or struggle you face?

(Note the language is not, “What is YOUR biggest struggle?”, which is more ego challenging. “Struggles you face” subtly refers to something that is the fault of others.)

By asking this in an open ended way — and because I actually cared, vs. looking for an opportunity to pounce and pitch and explain and convince and sell something — the client would typically tell me struggles they were dealing with.

4. What happens if you don’t get there?

Here is the gold mine. At this point they will tell you how bad it is if they don’t get there. They will reveal what is most important to them, and what they are most worried about.

If you ever get to this point, you won’t need to to any convincing because they have already convinced themselves how important this problem is to solve. All you need to say is something like, I think I can help you solve this problem.

The maturity model

5. Where are you in this process compared to others?

This is a final question which I would sometimes use to push the discussion a little further.

At this point it’s handy to have a simple diagram which shows the evolution of how companies solve a particular problem. This is sometimes called a “maturity model”.

Basically it shows how organizations act in the beginning, middle, and end of learning how to do, and then doing something successfully.

If you have a version of a maturity model associated with what you are selling, it can be a powerful conversation tool in a sales situation.

I would show this model and say, “Here is how I have observed other organizations evolving over time to solve similar problems, where would you say you are now on this chart?”

They think about it and then point to something — and then the sales team would know exactly what to sell and how to sell it.

Sales could simply say, “We can help you get from point C to point D, and make sure you solve these two problems on the way. Would you be interested in learning more?”

Sold. No convincing.


I will re-iterate, that for this conversation to work well, it helps to actually care, and to have some natural curiosity. Both of those things create a posture of interest and respect and help the customer to share more.

I remember one instance when I had this conversation with the kind of executive who might be cast in a movie as a stereotypical, successful executive, but horrible person. His office space occupied the entire top floor of a building with lots of marble and glass, and he had at least 4 assistants guarding a series of gates between the him and anyone else.

He was a grey-haired and over weight, and as soon as we walked in, he put a huge cigar in his mouth and leaned way back in his chair with his feet up on his desk. There was no respect coming my way.

It was not easy to genuinely care about how he was doing, but I did my best to get into the right frame of mind. I thought — he is a business person with real struggles somewhere in his organization that are difficult for him — so I cared about the struggles.

I asked, “What are you trying to accomplish in your business?”, he gave me a dismissive answer. I asked, “Is everything going as smoothly as you would hope?”. He thought for a minute and took his feet off the desk. Then he started to talk.

When I asked, “What happens if you don’t solve these issues, and don’t meet this schedule?” By then the cigar was put away.

I showed him the maturity model and asked where he thought his organization was in developing this particular competitive capability. He got a little pale when he realized how close to the beginning of this model his organization was and how far there was to go. By this time he was leaning forward, looking me in the eye, asking for help.

It was really that easy.

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About Patty
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Patty Azzarello is an executive, best-selling author, speaker and CEO/Business Advisor. She became the youngest general manager at HP at the age of 33, ran a billion dollar software business at 35 and became a CEO for the first time at 38 (all without turning into a self-centered, miserable jerk)

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