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Sales Development

Top 4 Brutal Discovery Call Mistakes – Part 1

Jacco van der Kooij

Written by Jacco van der Kooij

Founder, Winning by Design


The most important skill to help with closing deals and negotiation comes down to your first conversation.

A great discovery call, which is typically the first 30-45 minutes scheduled sales call, will do more for your quota than any other part of the sales cycle.

You need to find out the real issues your customer is trying to solve.

If you lose deals due to price, delays, competition or the frustrating black-hole of “gone dark” – it’s most likely because of a poor discovery call.

Ask Great Questions AND Actively Listen

It’s not rocket science. Sales is a profession. There are fundamental skills that can be mastered, and others that will always need refining. Like a doctor learning to diagnose, or a blacksmith forging a blade – the best-in-class make it look easy.

It’s not.

Top 4 Discovery Call Problems

The top mistakes salespeople make:

  1. Ask bad questions
  2. Say “Awesome” or “Got it” after a customer’s answer, then ask an unrelated follow up question
  3. Pitching the same features to everyone
  4. Aligning the next-steps with the salesperson’s timeline (quota), not the customer’s desired outcome (value)

1. Questions

There are 2 fundamental types of questions: Open vs. Close-ended questions – the latter wrongly getting a bad rap in sales.


Answers to these questions are typically “yes” or “no” or fact-based that help you understand the circumstance of the customer. But too many of these in a row make your conversation turn into an interrogation.

Close-ended questions are powerful when used at the right time.  “Are you ready to move forward?”

Show-not-tell that you’ve done your research. This is okay: “How many offices do you have?”

This is better:

“I noticed you opened up an office in Dublin, does that mean you have 5 offices worldwide?”

Do not do this: “I’ve done a lot of research about you and your company, but could you just tell me a little bit about yourself and what you’re looking to solve this year?”.

UGH.  Don’t waste their time. This question SUCKS.

Instead, help set the framework of the conversation by asking simple but important questions to qualify while setting the stage about where you’ll take the conversation.

Open-Ended Questions

require longer answers.  These questions are about your customer; both for their business, and to establish personal priorities. If they tell you they just raised a round of funding and are planning to build out the sales team, find out how they will share best practices with the new reps to ramp quickly.

Here’s some great ways to make sure you ask these types of questions

  • What effect does that have on… 
  • How often does that cause…
  • Does that ever lead to…
  • What is the result when…


2. Active Listening

After you’ve asked a great question, make sure listen and try to understand what they said before asking another question.



Show the customer you are listening through clarifying what they said, andmirror uncommon words or phrases.

3. Pitching

Stop the urge to sell your product.

No one cares about you or your product early in the sales cycle – they care about the impact of solving their problems.

What’s in it for me?

Remember: customers don’t trust sales professionals at first – or any stranger for that matter.

Except for one type of stranger. A peer with a similar challenge that was solved.

pitchingEstablish expertise and credibility early on in the sales cycle. Let your existing customer’s help you sell through sharing a use case.

Instead of telling them “We can do that with XYZ feature” – share how someone like them solved a similar problem, and the results they achieved.

4. Customer’s Timeline

The key to every deal is to understanding what is in it for the customer.

You do this by identifying a critical event. This is defined as an important solution that must be in place by a certain time or there will be significant consequences.


When you think you’ve identified a timeline that is relevant to the customer, ask:

“What would happen if you miss that date?”

Typically, when you’re ready to define next steps, salespeople will lead with the salesperson’s timeline:  “You need to sign by end of the month”.  Instead, start with the customer’s timeline, and work backwards with all the steps laid out for them to get their solution in place.

Your email or call could go something like this: “In order to help you meet your goals by October 1st, we’ll need to set up a training that takes about 1 week, review the contract with legal which takes about 2 weeks. That means we’ll need the PO signed by September 8th.”


Most new sales professionals offer feature-based solutions way too early into the conversation. Focus on what your customer is looking to solve, understanding their pain, what makes their situation unique and see if you can help guide them to the best solution.

Interested in learning more?

Part 2: Here are some best practices in mastering the perfect discovery call.