In the last decade, the explosion of sales technology has changed the way we conduct sales and marketing. Today, we can find an application to automate and analyze almost any part of the sales and marketing process making us far more productive and knowledgeable about our customers than ever before. Companies are responding by investing more; according to, the average annual spend on sales technology is up 22% costing a business about $4581 per rep a year. However, as our technology stacks mature and our data gets bigger, its causing us to shift our focus from what I would consider the most impactful part of a sale: the conversation.


No matter how sophisticated your tech stack may be, if you are selling a complex solution, sellers still need to engage and communicate with buyers.

As quotas increase and the need to do more with less becomes a focus, I often see sales leaders trying to template and automate their entire sales process. The customer becomes less of a focus and instead the sales stages drive rep activity. One of the most common mistakes a sales rep makes is to jump into a solution before the buyer has seen a clear need to solve the problem. For example, I often hear things from a sales rep like “the buyer had a demo, so my next step is to send a quote and offer a trial or close the business”. When we try to automate our interactions, it often translates from the buyer’s perspective into a conversation where the rep was focused on their agenda; they didn’t listen, asked questions to fill in their own knowledge gaps and then tried to force a decision by offering discounts and incentives.


Conversations directly impact the duration and success of your sale.

Think about your last sales conversation: what insight did the buyer learn that was not directly related to your solution? Our sales reps talk to hundreds of people a year and if they are even a tiny bit curious about a potential buyer’s motivation for talking to them, they can learn a lot about what’s causing change. By asking insightful questions, they can quickly develop a knowledge database on how your industry approaches problems and organize themselves. They learn key metrics, internal process and the various tools that a buyer uses. The seller begins to see patterns and this insightful industry knowledge is not only extremely valuable to a potential buyer; it can also be used to help uncover exceptional value by guiding them to better define the problem, think about something that’s often overlooked or to see a problem differently.

You might be asking how does this help us hit our numbers? Questioning skills are essential for positioning your solution. When your sales team can craft questions in such a way that the customer invites you to offer your advice and expertise, and extends the opportunity to discuss your solution, a strange thing happens: trust develops, stalled deals begin to disappear, you no longer need to rely on discounting to close business, forecasts become accurate and revenue increases.

The next time you are looking to solve a sales funnel challenge, before trying to add another technology solution, stop and consider if it’s time to change the conversation.

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