Once you have made a connection with a decision maker and you are finally in front of them, you want to have an engaging, interesting conversation. Your goal is to begin building a relationship.
In this third sales training article in our series based on The Multiplier Sale™ sales accelerator program, we identify ways to engage a prospect through asking questions that will open up the conversation in different ways. How to ask good questions is a key skill for anyone who works with people, whether it be in a sales role or in leadership, consulting, coaching or even parenting.
In this article, you will get tips for how to:
- Stay focused on value
- Formulate engaging questions
- Develop strategies for telling your story
Catch all the articles in The Multiplier Sale™ Series!
The Multiplier Sale Step 3: ENGAGE

Asking good questions is perhaps the greatest skill set you can develop as a salesperson selling your company’s services. Our human brains are problem-solving machines, and when we are asked a question, our minds immediately go into problem-solving mode, trying to answer the question.
When I ask you: “what color is your house?” – what happens in your brain?
You cannot NOT immediately start thinking of the answer. When you ask prospects insightful questions, they are more likely to want to respond in a way that opens up a more meaningful conversation with you. The art of asking takes great practice to perfect, and it is one of the most effective ways to engage someone in conversation.
Focus on Value
What is your value proposition?
If you don’t know what your customer values, you have no valid value proposition.
Engaging clients is all about value. However, presenting a strong value proposition requires that you understand what the other person values, what is important to them, and what they consider to be a successful professional engagement. Value is not about you.
Value is not about your product or your service. Not even a little bit. It’s about what the other person values, and whether the services you are selling match their value system. Value is in the eyes of the beholder, and recognizing what the other person values is key to presenting a strong value proposition. It’s always about the other person.
“Seek first to understand, then to be understood.”
– Stephen Covey
Have you ever been on a date when the other person just kept talking about themselves and how great they are?
How did that feel?
Considering your ideal customer or client:
- What is their business strategy?
- What are their objectives?
- What does your ideal customer care about?
- What unique challenges do they face?
- What is their personal agenda?
Find out how your customer defines value, and what is valuable to them. The best way to do that is to ask good, open-ended questions.
“Tellin’ ain’t sellin’. Askin’ is.”
– Unknown Texan
Master the Art of Asking Questions
What makes a good question?
The most powerful tool a salesperson has is the art of asking questions. Well-placed questions have the power to open up a conversation, shift the focus away from you, the salesperson, and invite the person in front of you to open up. This should not feel like an interrogation!
Asking good questions is an art, and a skill that takes practice to perfect. Open-ended questions – questions that cannot be answered by a simple “yes” or “no” – tend to open up the conversation more. These types of questions typically begin with “who,” “what,” “where,” “when,” “how,” and “why.”
After each question, don’t simply move on to the next. Drill down further. The best question of all, the “bacon” question that makes everything better according to Michael Bungay Stanier’s The Coaching Habit, is the “AWE” question: “And what else?”
Following up every answer with “and what else?” tends to reveal a whole new layer of information, and it can be used multiple times in a single thread of questioning.
Ask Qualifying Questions First
You may have heard the phrase “lose early” – in sales, this refers to the practice of stopping the pursuit of a prospect as soon as it becomes clear it is not a good fit from a product/solution standpoint, or there is little to no value alignment. If the deal is already a “loser,” don’t waste cycles on chasing down business that is unprofitable or otherwise misaligned.
Before spending a lot of time engaging with a prospect, it is important to qualify – to determine whether this is a viable business opportunity. A quick and simple way to approach qualifying a lead is to verify the budget, authority, need, and timeline (BANT) of the project.
Pain-Discovery Questions
Formulate your questions in a way that builds trust, is rooted in empathy, and wired for curiosity. Practice asking questions in order to open up the conversation to uncover pain. This should not feel like an interrogation, but rather like a bonding experience. Engagement and revenue growth come from the alignment that happens when your business offerings alleviate pain for prospects and existing customers.
Create a list of ten possible open-ended pain discovery questions you can use to lead a meaningful conversation with a prospect. Incorporate the elements of BANT; add additional drill-down questions or variations that you can pull from.
Tell Your Story
Storytelling absolutely has a place in business.
Telling your story is a powerful way to engage an audience. People buy from people, and they buy from people they like. Likability has a lot to do with relatability. As humans, we relate to one another most effectively through stories.
To formulate your story effectively, consider the following questions:
- WHY does your business exist? (In three to five sentences, what is the story behind your business?)
- HOW can you personalize your business story for your audience?
- WHAT pieces of your personal story are relevant to include?
Practice telling and presenting the story of why you exist, how you can help your audience become healthier, wealthier or wiser, and what the evidence is, based on stories of transformation from clients you have helped in the past.
“Your stories don’t define you. How you tell them will.”
Resources
Further Reading – if you would like to dig deeper, consider these books:
- The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier
- Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink
- Building a StoryBrand: Clarify Your Message So Customers Will Listen by Donald Miller
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