How to Have a Great Sales Conversation

Create a blueprint to acheive repeatable success.

Great sales conversations don’t happen by accident and as a professional salesperson it’s your job to develop great communication skills to guide prospects through their buying decision. Creating a blueprint for your discovery process provides a systematic approach for uncovering challenges, and guiding prospects to meaningful solutions.

Situational Questions

A discovery blueprint starts with 3-5 situational questions. These are questions to orient the conversation and help define the current state.

When we approach prospects evaluating OverQuota we ask:

  • How many sales reps are on the team?
  • Are you hiring and growing the team?
  • What technology is in place to support reps in selling?
  • What’s your current sales process like?

Situational questions will vary based on your buyer persona and what information you need to gather during the call. Overall the general purpose of these questions guides the conversation in the direction you need it to go.

Pain Questions

Pain questions are designed to uncover problems the prospect is experiencing related to the solution you offer. Deliver pain questions in three levels to systematically uncover more impactful information.

In the context of selling OverQuota to VP of Sales we ask:

  • Using the current tools and processes, what percentage of the team is achieving quota?
  • Why do you think only X percent are achieving quota?
  • How do you foresee this level of quota attainment affecting {company}? 

By drilling down and uncovering the issues they’re currently experiencing you can better tailor the sales process and information you provide to best fit their exact situation.


After clarifying with situational questions and uncovering a few pain points with pain questions, providing a summary back to the prospect demonstrates active listening and clear understanding.

It sounds like you have 10 sales reps on the team today with plans to grow by 5 more by the end of the year and about half of the current team is achieving quota which puts {company} at risk of missing the annual revenue target - did I get that right?

Active listening and taking notes can be difficult to juggle. Let OverQuota automatically help you with the note taking so you can focus and be present on the call. Paying attention to a prospect and making them feel heard with summarizing is essential to a successful call.


Following the summary and gaining alignment confirmation from the prospect, most salespeople go into pitch mode and discuss their solution. This approach is called solution selling. Alternatively, top performers are consultative salespeople and before discussing solutions, demonstrate empathy. Sharing a customer story with the prospect which shows you’ve seen this challenge before and how you helped a similar customer overcome it is a great way to demonstrate empathy.

We understand the challenges of supporting a large and growing remote sales team, especially as quota continues to increase in order to hit aggressive revenue targets. We have helped hundreds, including ACME who is also in the FinTech space, put a standard sales process in place with technology that helps drive adoption across the whole team which improves sales execution of every rep. Specifically, within 6 months, ACME went from 30% to 90% of their sales team achieving quota. 

Empathy is a way to connect with the client while also providing credibility in you and your product. This is not a fix-all tactic though and should be used sparingly when it naturally flows into the conversations.


The final piece of the blueprint is establishing two levels of impact. Rational impact relates to the company and is measurable, it will likely be related to increasing revenue or decreasing costs over a period of time. Emotional impact relates to the person and will likely relate to eliminating manual process and wasted effort or time. Professional sellers help buyers define both rational and emotional impact because buyers make emotional decisions first that are then rationalized with facts and figures.

What would it mean for {company} if we can deliver a solution that results in 100% of reps hitting quota instead of just the 50% today?

How would this impact you personally as a VP of Sales?

Asking impact questions like this is the final part of the blueprint and helps the prospect start to visualize how your product can help benefit them personally as well as their company. However, this is not the final part of the sales motion, but it should tee you up to locking down next steps.

Defining your blueprint and following through with it will create repeatable success in sales. Top performers have figured this out and are using platforms like OverQuota to make execution of their blueprint possible. You no longer need to scramble through various word documents or note taking apps. Instead, create your discovery call blueprint in OverQuota, an easy to use and fully integrated sales execution platform.

Interested in a Discovery Call Blueprint Overview?