Ep. 15
How to sell to CEOs and Senior Executives with Chris Orlob

The Sales Conversation

Episode Overview

In this episode, Chris Orlob, Senior Director of Product Marketing Gong.io and I talk about what’s working and not working and CEO level sales conversations. Chris shares some surprising insights about how things change based on how high up in the organization you are having selling conversations – and how things should change to be more in-tune with senior business decision makers.

The Study Says … for Executives … No More than 4 Questions!

In the summer of 2017, Gong.io created a discovery call benchmark report. They analyzed a bunch of discovery calls to figure out what was working. They found that 11 to 14 questions was the “sweet spot” for a discovery call. Then in 2018, they released a new study that was pretty contradictory to original benchmark report. It showed that there was a very sharp decline in the likelihood to win a deal if you ask more than 4 questions. The difference between these two research studies was the first one, the one with the suggestion of 11 to 14 questions, didn’t differentiate who the buyer was or what level they were in the organization. And the data for the second study was exclusively C suite executives. Bottomline, there was a sharp decrease in success rates after asking just a few questions at this senior executive level.

What’s Different About Asking Executives Questions?

Sellers often go into discovery meetings asking information-gathering questions that enable the seller. If you’re going to ask questions to a senior buyer, they should be questions that benefit the buyer, not you. These are questions that maybe make them think differently about an opportunity that’s sitting under their nose, or it’s reframing a problem that they’ve been dealing with. Instead of going through this, like generic line of discovery call questions where you’re trying to qualify them, they don’t really have patience for that. They don’t like taking sales calls anyway, and when they do, they’re doing it on a whim and a hope that the seller is going to provide value during that customer conversation. Most of the time, the seller does not.

There are a few interpretations of this data. The takeaway is to not ask four questions and that’s going to solve all your problems. The first suggestion to get across is the questions you ask have to change – they have to be thought provoking. They can’t be self serving. And then the second part is the bulk of your meeting with a senior executive has to be built around delivering insights to them, not just asking a bunch of questions.

Provoking Senior Executives

Back in 2009, when we were in a downturn, Philip Lay, Todd Hewlin, and Geoffrey Moore wrote an HBR article entitled, “In a Downturn, Provoke Your Customers.” This was seminal work that probably started the wave thinking around what we call “insight selling” today. I was working with Infosys on their cloud strategy go to market strategy and messaging, and their cloud leader, Vishnu, would mention to executives, “I’ve looked at IDC, Forrester, Gartner and others, and pretty much everybody is talking about the cloud and workloads in the cloud. And there’s a prediction that in three years, about 70% of enterprise workloads will be cloud-based. So, Mr. or Mrs. CIO, where do you think you’re going to be in three years? Do you think you will be on benchmark, below benchmark or even ahead of the pack?” And then he would watch a look of consternation form on their face. Then they would discuss their cloud strategy and how Infosys could be helpful. The best practice in asking provocative questions is to tee the question up with an interesting industry insight or fact or stat, and then move into the question. Then you are leading with insight. You’re asking an open-ended questions. You will know you were successful when the executives cancel their meetings for the rest of the day so that they can think about this and maybe go for a walk around the block.

Elevating Sales Messaging – from Tactical to Strategic

It comes down to messaging in an educational way. It’s elevating your message to be more strategic rather than tactical. A lot of sales messaging is very tactical. Either it’s product-driven, or it’s just talking about maybe a valid problem or opportunity – but not something a C level executive would deem as strategic. For example, Gong.io used to talk about sales coaching quite a bit and still do in some contexts. But when you tell a story about sales coaching, without doing the right things to make it sound more strategic, you get punted down lower in the organization – you get punted down and delegated to the person you sound like. And for us, that’s typically like mid-level sales enablement person. If we tell that story and don’t get me wrong, we love selling to sales enablement and helping them buy from us. But we would rather stick with the C suite executive.

Ways to Make Your Sales Messaging more Strategic

There are two ways that come to mind that you can make your messaging more strategic. The first way is tying your solution to a more strategic problem that the executive care about. That’s the obvious one. It’s very straightforward. For example, at Gong.io we talk about a major industry shift – product differentiation is dead. The way to beat your competitors has more to do with your sales conversations now and now that’s tying it to a more strategic issue. If you can find an obvious bigger, more strategic problem to tie your value proposition to, that’s your first obvious way to elevate the strategic importance of your messaging. But not everybody has that luxury.

The second way to make your sales messaging more strategic is to take whatever your messaging against today that is labeled as a tactical problem and wrap it in a larger story. So for Gong.io that would be coaching and tell a story that elevates the strategic importance of that problem. This is called agenda setting. Here’s the example storyline we’ve used for setting the agenda. We have found that there is a shift in the industry. The sales environment today is completely different than it was 10 years ago. 10 years ago, you could hire a sales guy or a sales gal. And their expectations were to just show up and sell and make money. But we have this shift in the last 10 years called the millennial workforce. And these types of sales reps have much bigger expectations from their employers. They don’t just want to show up and sell. They want to be the best sales guy or gal, they expect their employer to invest in their training and their development and to help them along the way. And if you don’t do something to do that, all they have to do is respond to the latest LinkedIn InMail they’ve received from a recruiter that week and they will go elsewhere. And then we introduce the concept of coaching and how it fits into that. And now coaching is not framed in this tactical sense of, we can increase your win rates by one or 2%. It’s framed in the sense of, hey, you’re dealing with millennials. Now you’re going to have to provide good coaching, just to build your organization, prevent attrition, and maintain like a world class company.

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