• Jeff Day

Sales Presentation Tip: Why Tech Teams Struggle to Land the First Sales Conversation



CROs need to gut-check these questions. Out of the last one hundred team sales presentations, how many do you believe to hit the intended presentation outcome? Why did they hit or miss?


Too many sales and marketing people believe that their products and offerings are so good that they need little to no explanation. The truth is, some are really that good. But in a world where differentiation is everything, most teams and brands will struggle not only to differentiate but to nail the essence of their story.


Companies that sell technology and technology services wrestle mightily with this. And herein lies your challenge. First, you may present to a highly business-focused leader needing a specific set of justifications. Now juxtapose that against a more technical implementer with another set of concerns. In some cases, this may be the same person. More often, the former leads the latter. The fact is that both personas matter. And considering that tech leaders in the business (CIO/CTO) are managing massive budgets, getting this right is critical.


One way to move the needle quickly is to embed the skill of starting with provocative questions into your daily interactive dialog. Provocative questions force thought, even when an idea is not readily accepted by your customer. The question is meant to be challenging and will ignite an opportunity for dialog. Starting the conversation with a well-planned question will earn another 15-seconds in the conversation. Stay away from yes and no questions. Rather, lead with the 5 Ws in your questions – who, what, when, where, and why. Here are some ideas:


  1. Would you share who some of the other decision-makers are in this process?

  2. What acceptance criteria would the average person not know about this program?

  3. When the program is fulfilled, how will the organization look back on the decision performance?

  4. Where are the other dependencies that are crucial to this program's succeess?

  5. Why did the organization not included consideration of X, Y, or Z?


Be creative and stay relevant. Your mission is to add value.


Leaders need to teach the skill and culture of good starter questions and advance planning. The most important part of a buyer’s journey is when the emotional connection becomes tied to the overall decision. Strong buyer and seller relationships take root in healthy exchanges led by provocative questions.

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