How a Great Discovery Call Earned Me the Biggest Deal in My Startup's History

About the author: Dan Smith is a Growth Specialist at Winning By Design, consulting for high-growth B2B technology sales teams. 

The new era of sales comes down to a great discovery call. You need to find out the real issues your customer is trying to solve. If you lose deals due to price, competition or the frustrating black-hole of “gone dark” - it’s most likely because of a poor discovery call.

If I had to choose one thing that helped me win the biggest deal - it would come down to this: I asked one unusual, but simple question at the beginning of our discovery call.

After that, we had a great conversation without distraction on either side. I was able to pick up more things from her answers and quickly adjust the pace of the conversation when I realized something resonated or was not important.


Get to Know the Customer on the Discovery Call

6 months into being a the 4th AE at a fast growing startup in the midst of raising our Series B, I landed a call with the Director of Sales at a $2B valued public company.  Jill (not her real name) was leading a team a team of about 30. After a short previous qualification with her direct manager the week before, this call was scheduled for 30 minutes on a Thursday afternoon late October. Everything about this call was normal until I asked:

“May we turn this phone call into a video call?”

Instead of doing an audio only with a presentation, I asked Jill to speak with me face to face, business person to business person.

Jill and I had a valuable first conversation. We built a relationship around sharing best practices in sales, and she shared with me the strategic initiatives for the company, and the impact it could have for her personally.

We randomly met 1.5 years later on the streets of San Francisco during Dreamforce, she still remembered our first meeting.


A Qualification Problem is a Big Problem

The top 3 mistakes salespeople make on first calls are 1) not listening to the customer and being curious about their business, 2) pitching the same features to everyone - regardless of what the customer is actually interested in and 3) not setting appropriate next steps.

Most new sales professionals offer feature based solutions way too early into the convo. This was especially bad for me - I loved getting into the in’s and out’s of the product so I could answer any customer question.

When I was speaking with Jill - I could see if I started going down the wrong path based on her level of engagement.  I immediately got out of the weeds by asking a question, and ultimately learned about what was most important to the potential solution we could provide.

Don’t worry if you make this mistake at first - it’s easy to understand why: you work for a company you are excited about, with paying customers who love you.  Every prospect is a potential customer, right? As soon as you become aware of this common selling mistake, change your approach in favor of being curious about your customer by asking a question, or clarifying your understanding of their desired solution.

Too many sales people don’t realize that customers want to be qualified. I learned later, Jill usually checks emails, or texts during “vendor” sales calls - but because we were on video, not only were we both fully engaged, we were able to end the call early.


Learn the Anatomy of a Discovery Call

Preparation: Do some research about who you’ll be speaking with. If your company has already had conversations with the person you’ll be meeting with, find out what the customer mentioned they care about.  Check LinkedIn for uncommon-commonalities (Did they attend the same school? Marathon runner? Volunteer experience?).  Show that you care.

Strong opener to set the tone of all successful meetings.

The best start accomplishes three things - the expectations of what will be discussed, the time and the format.  Discovery calls need to be conversations, and not 1-way sales pitches. The customer needs to know they have control, and their concerns will be addressed.

Try this on your next call and let me know how it works: AxNOT

  • Appreciate you taking the time for today’s call.
  • x = time →  “We have 30 minutes scheduled to speak today - does that still work for you? {Remember to listen to their response, and adjust your call if necessary)
  • Naturally, you will have questions for me about my company….
  • Obviously, I have questions for you about your team, goals to understand if we could help.
  • Typically, this call will end with us determining next steps in evaluation, or if at any point you realize this is not going to be a good fit - will you please interupt me to let me know?  I have thick skin…. :)

Once you complete this opener (about 45 seconds) - confirm the agenda you sent over before the meeting - is there anything else your customer wants to cover? Then ask everyone on the call what they are looking to get out of the call. Write down their names, and make sure you address their top priorities before the end.


Diagnose After Discovery

Ask them close ended questions first - then lead into open-ended.  Question Based Selling and SPIN are the two best frameworks to have a customer centric conversation.

Start off with situational questions that show you have done some research, but also help you qualify the customer on basic minimal requirements.  If you’re selling a collaboration tool, instead of asking “How many offices do you have?” Ask “I noticed you are hiring in at least 3 of your global offices in Boston, Dublin and Shanghai, how many people are you looking to expand to?

When you begin asking problem questions - don’t just ask the generic and over-used “what keeps you up at night?” Instead ask more thoughtful “When speaking to other Directors of Sales, they mention challenge 1, 2 and 3 are on their top priorities to solve. To what extent is [customer challenge #1] important to you?”

Outline of a Discovery Call

Once I properly diagnosed Jill, we customized her “prescription” of how to evaluate our solution that was based on her timeline that would solve her challenges.  

Jill mentioned their Fiscal Year ends in December - so we agreed to a mutual plan for a pilot to line up with their holiday schedule, procurement process, training requirements to ultimately make sure her team would hit the ground running in Q1.



Because of the trust we had built starting with our first call, Jill went to bat for our mutually agreed upon solution even when the pilot didn’t go perfectly. We were able to address her team’s concerns, and expand the opportunity throughout the entire company and found the price that was fair for both parties.

What are the most important questions you ask on your discovery calls?