How to Have Meaningful Conversations That Triple Your Sales

Tyler Gregerson

Reading time: about 4 min


  • Sales

One of the biggest problems I faced as a new inside sales rep was how to have a conversation that resonated with my buyer. Often during a follow-up call, the prospect wouldn’t even remember in the slightest what we spoke about previously!

After diving into the structure of my calls with my manager, we found that my calls were more of the interrogation approach, asking closed-ended questions. If there is one major piece of advice I can give, it is to learn from my failure. Do NOT ask simple questions that you can find on the internet! Doing so instantly makes your buyer less interested and wastes their time.

We work hard to prospect and get people on the phone, so do not miss this small window of opportunity to create something meaningful for both the customer and yourself.

There are three major steps to having this meaningful conversation:

  1. Ask “open plus” questions that get prospects talking and brainstorming with you about their challenges.
  2. Genuinely listen to and be curious about their responses.
  3. Dig into why they answered your questions the way they did and what their vision is to solve the challenges they brought up.

Open plus questions

Peter Chun's Open plus method, is a collection of principles used to form effective open ended questions. The importance of asking open plus questions is to get the prospect brainstorming with you. As many of you know, the people we are calling are also getting called by dozens of other sales professionals, usually a competitor selling a similar product. You NEED to establish a difference in how and what information you gather during the initial meeting. If you ask the same boring questions as the next guy, you will likely be pushed aside. Be straightforward and direct in the questions you ask. Here are some examples of effective open plus questions:

  • Help me understand your day-to-day as VP of Engineering.
  • Explain to me some of the challenges you and your team face working on projects.
  • Walk me through what is needed to purchase this device or software for the company.
  • Describe to me your team’s vision on where you’d like to be a year from now.

When we ask an open-ended question and just stop talking (Yes, STOP talking and wait, even past the point of awkwardness), we can elicit responses from our customers that truly get to the point of why they do what they do.

Listen genuinely

Listening is the most important element in all steps of the sales process! Your prospects are still people, and people like to feel important. People also like to talk about themselves, whether it’s how much they love a process that’s working for them or how frustrated they are with a situation at work. Listening will give them a feeling of comfort and give you the ammo you need moving forward.

Genuinely listening means we consistently engage with them to show we are active in the conversation. The best way I’ve found to do so is to restate what it is the prospect said. Doing so will get you both on the same page and allow them to add anything you may have missed.

Dig into the why

This is what separates the top performing reps from the low performers! As you dive into the conversation, digging into the “why” is a crucial step that cannot be skipped. Doing so looks something like this:

This method of conversing opens up the floor for the prospect to tell you the challenges they are facing and why these matter to them. After they’ve done so, do NOT begin to sell them your product or feature, no matter how tempting it is. Write the information down for later and keep digging into open plus questions.

The goal of the discovery call should be to ask questions in a way that leads your buyer into creating their own value proposition for using your tool with their team. If you create an atmosphere of brainstorming, they can usually see where your product will fit into their workflow. If you do this effectively, they will be ten times more likely to buy your solution and work with you on future deals. 

About the author

Upon graduating from the The Huntsman School of Business at Utah State, Tyler Gregerson knew exactly where to take his career. Tyler has always had a passion for the profession of sales and its influence on an individual's mindset and ability to communicate. He currently works as a Business Development Rep at Lucid Software which he describes as "an incredible company where our team is focused on making an impact in the world through creative thinking."


Lucidchart, a cloud-based intelligent diagramming application, is a core component of Lucid Software's Visual Collaboration Suite. This intuitive, cloud-based solution empowers teams to collaborate in real-time to build flowcharts, mockups, UML diagrams, customer journey maps, and more. Lucidchart propels teams forward to build the future faster. Lucid is proud to serve top businesses around the world, including customers such as Google, GE, and NBC Universal, and 99% of the Fortune 500. Lucid partners with industry leaders, including Google, Atlassian, and Microsoft. Since its founding, Lucid has received numerous awards for its products, business, and workplace culture. For more information, visit

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