Discovery is the most important part of the sales process. It is here that you build emotional connections with stakeholders and gather the information you need to build the case for doing business with you. 

Many sales professionals tend to make big mistakes in discovery conversations. These mistakes that can destroy both your credibility and relationships. It is crucial that you become aware of these common mistakes and avoid them.

Taking Short-Cuts

The majority of the mistakes with discovery happen because salespeople don’t understand the value of discovery. When you don’t value discovery you take shortcuts. You invest 10% of your time in discovery rather than 80%. You go through the motions, check the boxes, and fail to listen. This leads to shallow discovery, a weak business case, broken relationships, and a much lower closing ratio. 

Asking Stupid Questions 

When you ask your stakeholders stupid questions that you should already know the answers to, you are exhibiting your lack of preparation and commitment. For example, stupid question #1 is, “What do you do here?” 

If you can easily find the information on the internet or social media you should not be asking for that same information in a discovery meeting. The most effective questions position you as an expert consultant by demonstrating that you understand your prospect’s business, industry, challenges, and opportunities. 


Too many salespeople focus on their outcomes instead of those of their prospect. Stakeholders don’t meet with you to help you hit your quota. They are there to solve their own problems.  When discovery conversations are all about you – transactional rather than relational – it kills opportunities. Stakeholders don’t want to waste any additional time answering your self-serving, leading questions. There is no value for them, so they ghost you and move on.  

Focusing on Your Next Question Rather Than Listening

One of the biggest mistakes that salespeople make during discovery conversations is getting so wrapped up in the process of asking the next question that they stop listening to the answer to the one they just asked. 

When you are not listening, stakeholders know it – especially when they have to repeat themselves because you were not paying attention. The failure to listen destroys relationships fast.

When you disconnect from the conversation, because you are thinking about your next question, it causes the discovery conversation to feel disjointed and forced. So, rather than asking one question after another from a predetermined list, choose a conversational organic approach during which one question builds on the last, based on your stakeholder’s answers. 

Interrogation vs Conversation

Imagine the scene from a movie. The villain is strapped to a chair in the middle of an empty room. A bright light is pointed into his eyes while the interrogator peppers him with accusatory, leading, closed-ended questions. The interrogator intends to make the villain feel as uncomfortable as possible and push him off-balance, breaking him down so that in a moment of weakness he reveals his deepest secrets.

Many salespeople put their prospects in a similar uncomfortable position. These salespeople unload an avalanche of closed-ended, and often leading, questions that may come off as imposing, self-serving, and manipulative. In response, prospects deflect, obfuscate, and erect emotional barriers. 

On the contrary, artfully structured, open-ended questions asked in the context of a fluid conversation keep stakeholders engaged. When you treat discovery as a fluid conversation, rather than an interrogation, you disarm your stakeholders, draw them in, and lower emotional walls.

Asking Hard Questions First

Imagine that you see a stranger from a distance walking in your direction, a man you don’t know. He’s making a beeline right toward you. As he comes to a halt in front of you, your guard is up. Then, without hesitation, he begins peppering you with personal questions:

  • Where do you live?
  • What’s your mom’s maiden name?
  • How many kids do you have? What are their names? Where do they go to school?
  • What color car do you drive? Where is it parked?
  • How much money do you have in your bank account?

How does this line of questioning feel? What will you say? Will you give him the answers he’s looking for? Will you lie? How long will you stand there before screaming at him to get away from you or before running away?

This is how stakeholders feel when you begin your discovery conversations asking hard questions that go too far below the surface. It is human nature to put up an emotional wall when strangers start asking difficult, intrusive questions. 

In your role as a salesperson you are the stranger. When you ask questions that make your stakeholders uncomfortable before you have established an emotional connection and trust, their emotional wall goes up, and they shut down.

The key to breaking through emotional walls is beginning discovery conversations with questions that are easy for your stakeholders to answer and that they will enjoy answering. This is why it is crucial that you do your research on stakeholders and prepare easy questions that they will enjoy answering in advance. 

The more you become genuinely interested in stakeholders, the more valuable and important they feel. The better they feel, the more they will want to talk. The more they talk and you listen, the more connected they will feel to you. As you connect, you gain the right to ask the deeper questions that get below the surface.

The Pump and Pounce

The most destructive sales behavior during discovery conversations is the annoying tendency of pumping stakeholders for information with interrogating, closed-ended questions and then pouncing on the first opening to start pitching. Born from impatience and poor impulse control, this one habit will cause you to miss important clues, damage relationships, and lose out on sales.

Here’s how it works. During discovery, in response to a question, your stakeholder says, “We’ve been having a hard time with (fill in the blank).” Rather than asking deeper probing questions to gain clarity and understanding, you pounce and start pitching solutions. As soon as you start pitching, your ears turn off and so do your stakeholders.

The key to effective discovery conversations is patiently asking questions, encouraging stakeholders to talk, and getting all the information on the table before formulating any recommendations or offering solutions. In longer-cycle sales, discovery may span many meetings with multiple stakeholders before any presentation or recommended solutions are offered.

Failure to Prepare

Discovery is a language of questions. But effective discovery doesn’t just happen. To be effective, to be valuable, you must do your research and plan your approach, in advance, before you ever ask the first question. Trust us on this, when it comes to discovery, winging it is stupid.

The most egregious mistake with discovery is the failure to prepare for discovery meetings. Your lack of preparation will shine through in your weak, disjointed questions. Stakeholders will know that you didn’t care enough to do your research and develop your questions. You will come off as a hack rather than a professional consultant. You’ll waste time rather than creating value. 

This is a huge irritation to buyers. According to studies by Blender and SiriusDecisions, between 80% of B2B buyers complain that salespeople are unprepared for meetings – that these salespeople know nothing about them or their industry. Salespeople reveal this truth by asking questions that research could have answered.

Learn how to avoid bad questioning habits that damage relationships and your credibility in our new micro-course: 4 Discovery Questions You Need to Stop Asking Now

About the author

Jeb Blount

Jeb Blount is one of the most sought-after and transformative speakers in the world…

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