Are Great Questions a Skill You Want?

“After every difficulty, ask yourself two questions: “What did I do right?” and “What would I do differently?” -Brian Tracy

Asking the wrong question over and over again will never result in a good answer. Over the years, I have witnessed ill-prepared salespeople ask the wrong question, ask a bad question, and get frustrated when the prospect shuts them down.

The Importance of Questions

Well thought out questions are a salesperson’s best friend. They help uncover problems the prospect is experiencing. It can help them discover ‘who.’

  • Who you need to meet with
  • Who gathers/collates information
  • Who signs off on the requirements
  • Who makes the purchasing decision
  • Who signs the purchase orders
  • Who oversees the implementation
  • Who signs off on ‘done.’

It can also help a salesperson get to the prospects’ what.’

  • What problems are they having
  • What is the problem costing them
  • What can you do to help
  • What is their schedule for solving the problem

Knowing the Prospect

I can’t emphasize enough the importance of basic research before trying to get an appointment with a new prospect, whether on a cold call or followup call.

You should know what the company does to make their money and how they fit into their market. With only this little information, you can offer a reasonable entry for a meeting. With no information, you are at a significant disadvantage.

Whey you get the meeting, a lot more information is needed. Always formulate the questions before the meeting, so you show yourself as knowledgeable. Good questions are the standard.

Don’t ask ‘bad’ questions.

So, tell me what you do here at XYZ Corp. I’m sure we can help save you money and increase your profits.


Or maybe;

That’s a nice looking bass on the wall. You a fisherman?

First of all, they are busy and don’t have a lot of time for your meandering.

Here are some items to know before a meeting:

  • What the company does
  • How do they deliver value to customer, employees, and stakeholders
  • Who are the officers which lead to who you need to meet
  • Who are their competitors
  • Where are they strong in their field
  • Where are they weakest
  • What segment/industries do they serve

Ask Relevant Questions

Think about relevant questions. Here is the definition.

Closely connected or appropriate to what is being done or considered; appropriate to the current time, period, or circumstances; of contemporary interest.


First, in the first meeting, they probably don’t care about your company’s history or how long you’ve been in business. There is a time for that, but it shouldn’t be the first thing out of your mouth.

Think about your research.

  • Are they the leader in their industry or number two?
  • How does this apply to what you do?
  • How can you be relevant to them?
  • Is there a way to relate your knowledge to their problem?

Ah, their problem. Do you have other customers in their space? Whether you are working verticals or horizontals, you probably know some of the issues they have. Ask appropriate questions to see if it is true. Even if they have different problems, they will be impressed with your knowledge of the field they represent.
Use that to segue into specific issues they have. Always be thinking about how you can help them.
If you can help, they will be open to a discussion about your results with other customers.

Be Smart about Questioning

There are a few rules asking questions in an exploratory meeting. Here are rules that will set you apart.

  • PAY ATTENTION
  • BE FLEXIBLE
  • Be mindful of their time.
  • Do not ‘grill’ the prospect.
  • Formulate good questions before the meeting
  • Listen to the answers
  • Listening allows for great followup question
  • Explore where they are going in their thoughts
  • It’s okay to go off-script when they open a door.
  • Explore from the point of helping


Every product I’ve ever sold had many different ways of helping prospects. It is your job as a salesperson to discover one or more of those ways.

Here is my last thought.

Asking the wrong (or bad) question over and over will never result in a good answer. It might even get you escorted out.

What are some of your favorite questions to get the prospect talking?

If your talking, I'm listening