Sales Discussions that Work

Posted on April 23, 2024 Updated on August 18, 2026

Selling is challenging work, and often, “we” (sales and marketing teams) make it even harder than it needs to be. How many times have you seen a selling script, elevator pitch, or initial presentation that is long, boring, and undifferentiated? People have short attention spans, and nobody wants to interact with someone who doesn’t listen or is pushy.

Your initial discussion is crucial to your success. Instead of going over a list of features, reading a slide deck, and telling why you and your product are so great, let’s try something different.

1. Understand why people buy. Any change can be difficult, risky, and painful. So, the pain they are facing has to be even greater than the potential pain of change, or they won’t bother changing.

Your main job early on is to listen and work to understand their concerns. You may have a perfect solution, but if it doesn’t solve their pain, it holds little value to your prospect. This initial meeting is all about them.

2. At the start of the meeting, ask, “What would make this time well spent for you? What would you like to walk away from this meeting with?” Get them thinking about their problems and the value you may be able to provide, even if they don’t fully articulate them to you.

3. Ask questions and follow-up questions. People don’t lead with their significant issues, and someone unwilling to divulge anything likely isn’t a buyer. The more the prospect talks, the more you learn. So many sellers do not understand this simple concept. They want to dazzle you with features and demos – even if those things are not what the prospect needs.

4. Once you think that you have identified a pain, restate it, qualify and quantify it. For example, “You mentioned that your product release cycles are too long and complex. What is the business impact of that, and what would the impact be if you could reduce that time and effort by 50%?” Write their response down, in their own words, because it could be vital later.

If you identify several pain points, review them and ask the prospect to identify the top three issues from the list, and then ask why those three. Once you have their answer, ask if other stakeholders in their organization would agree with that list, and why or why not. Again, get them to expand their thinking and work through this, as it will help you identify other stakeholders who may have other priorities.

5. If you are giving a presentation, pull up the most relevant slide (customer problem/benefit slides work well here) and ask if this sounds similar to the problem they are facing. It can be a good starting point for getting the discussion moving in the right direction. By providing relevant information, especially about how you solved a similar problem for another customer, they will see the value of providing you with more data and information.

6. Don’t worry if you are not able to cover everything you intended, as long as the meeting is productive. I’ve also seen salespeople cut someone off and move on to a new slide rather than discussing something of substance. I was actually told once by a sales leader that five minutes of discussion is all that is required in an initial 30-minute meeting, because our goal is to pique their interest. That approach just doesn’t work. You may impress them, but if you don’t start building confidence that you can help them, there probably won’t be a second call.

7. Next steps. Keep in mind that your time is valuable, and qualifying out a prospect who is not a good fit is essential – it helps you avoid false hopes and lets you focus on people who might genuinely need your help. The next meeting could go many ways, but it’s best to ask the prospect. Would they like to expand the audience? Is there a specific issue they would like to address? Would they like a product demo or a technical discussion? Is something like a non-disclosure agreement (NDA) keeping them from opening up? Lack of engagement on their part is a huge clue. Be direct and ask the tough questions now to avoid wasting valuable time and effort later.

Here is a mini success story. In 2010, my team and I began selling the first commercial vector high-performance analytics database. Several products were already out that claimed to be 70x-100x faster than others. Our pitch was that we were 70 times faster than other products. That was self-limiting from the start and likely prevented people from contacting us.

After two months of minimal success (I closed a deal with a small hedge fund, which was the only sale in all regions), we started a weekly webinar called “Why Fast Matters.” The focus was on positive business outcomes rather than specific technology and features (“speeds and feeds”). We opened with some “What if?” statements, such as: What if you get answers from complex queries faster than your competitors? What if you could do that without the cost, complexity, delays, and limitations of a Star Schema or pre-aggregated data? What if you could do this on commodity x86 hardware? We would then briefly cover the breakthrough technology (a precursor to Snowflake) and offer a free half-day meeting with a consultant.

Within the first two weeks, we met with a company that was later acquired by PayPal shortly before eBay acquired PayPal. This company was about to spend $500K on a proprietary hardware expansion that would have only provided additional capacity for the following year. Their customers bought advertising based on queries against the last six months of their data. I asked the question, “What if they could query against five years of data and get answers faster than they do today? Do you think that would help them buy more advertising? Do your customers ever ask for this?” They said their customers frequently ask for 12 months of data and would be willing to pay more for these capabilities. Still, they did not have a way to do this cost-effectively.

I closed a $360K ARR subscription deal in two weeks, and they purchased $100K of commodity Dell hardware for our software to run on. They saved 8% over their planned purchase, and more importantly, they rolled out advanced querying capabilities (against six years of data) in less than a month. There was incredible value to them and their customers, and it generated more business for them. We wouldn’t have identified this need if we’d focused primarily on features and technology.

As an aside, I was initially chastised for going off message, but after the Australian team adopted our approach and began closing deals, it became the new corporate standard. If something isn’t working, focus on finding ways to improve it. Even incremental change can be meaningful.

In the words of Tony Robbins, “If you do what you’ve always done, you’ll get what you’ve always gotten.”