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Remember the movie The Wolf of Wall Street? There’s a famous scene where Jordan Belfort challenges a group of salesmen to “sell me this pen.” The task may seem trivial, but it’s a powerful moment that underscores a critical sales technique. Instead of diving into the pen’s features, a skilled salesperson would start by asking, “Why do you need a pen?” This simple question sets the stage to understand the customer’s needs, motivations, and urgency—transforming a mundane task into a meaningful sales opportunity.
It was the summer of 2006. I was on a short vacation. I worked for an enterprise telecom company as the country head. I got a call from the CIO of one of the largest IT services company requesting us to participate in their RFP process. The opportunity was worth a few million dollars. It required significant time and resources to participate. I was in half a mind to say No. They already had one round of presentations from the other telecom players. This call seemed like they wanted yet another bidder to expand the bidders pool. I used ‘Why’ as my sculpting tool to shape the opportunity.
‘Why do you think we should bid, Mr CIO?’ I could ask this question so bluntly only because I had leverage. It’s the CIO who reached out to us, not the other way round.
‘What have you heard about us that made you reach out to me?’ The most likely response to this question could be for him to say something positive about us.
‘Why do you feel that the others don’t have a significant headstart over us?’ This ‘Why’ question could be disguised as a What question. For example, What will you do to ensure others don’t have an unfair advantage over us?
I coached my team to ask deep and purposeful ‘Why’ questions throughout the deal – not just to get more clarity, but to improve our chances of winning. During final closing, when we were one of the final two suppliers remaining, the buyer got into a sticky discussion on go-live dates. Our proposed go-live dates were a few weeks later than the competitor’s. When the buyer acted stubborn about that, a good ‘Why’ question came to our rescue. ‘(Why) is the delay of a couple of weeks in going live so important?’ However, it was a delicate stage. We asked the question with a ‘why’ disguised as ‘what’: What is the business impact of this delay? We asked this from a context of curiosity and problem-solving. And we did solve the problem. The customer acknowledged that, at most locations, it will have a marginal impact. There were only two locations out of 18 where the impact would be significant. We then solved for those locations and won the deal!
“Why” operates like a Swiss knife—versatile, adaptable, and essential. It’s not just a question; it’s a tool, a frame of reference, and a lens for discovery. Let’s explore how “why” can be wielded effectively in various facets of the sales process.
1. Discovery: Unveiling the Truth
In sales, the initial phase of discovery sets the stage for all subsequent actions. Here, “why” serves as a compass, pointing to the heart of the matter. Some essential “why” questions include:
• Why change? – Why should the customer consider a different solution than what they are using?
• Why now? – Is there a pressing need or opportunity that makes this the right time?
• Why this approach? – Why does this particular solution resonate with the customer?
• Why us? – What makes your offering stand out in the customer’s mind?
These questions help sales professionals qualify leads, uncover motivations, and determine whether the opportunity is worth pursuing. But asking “why” too bluntly can sometimes feel like an interrogation. That’s where reframing comes into play.
2. Reframing “Why” as “What”: A Softer Approach
Although powerful, “why” can sometimes put the other person on the defensive. Reframing it as a “what” can achieve the same result with a lighter touch. For instance, instead of asking, “Why do you want to include us in the buying process?” you might say, “What aspects of our solution do you find particularly appealing?”
This approach helps uncover the underlying reasons without being demanding or sounding confrontational. It provides a more comfortable pathway for the prospect to reveal their motivations, helping to deepen your understanding and shape your approach.
3. Disguising “Why”: The Art of the Stealth Inquiry
If used too frequently, “why” can indeed sound like an interrogation. A savvy salesperson knows when to disguise it. Techniques such as labeling or mirroring, popularized by negotiation expert Chris Voss, can be used to extract information without directly posing a “why” question.
For example, if a customer says, “Your pricing is higher than your competitors,” you might respond with, “Higher than the other options you’re considering?” The repetition, coupled with the right tone, serves as a disguised “why,” prompting the customer to explain their perspective further.
Another technique that I use often involves non-verbal cues like a subtle expression of curiosity—a smile combined with a slight frown—as if saying, “Oh, really?” This non-verbal disguised “why” can nudge the customer to share more without you uttering a word.
4. Turning the Mirror: Asking “Why” to Yourself
“Why” isn’t just a question for customers; it’s a self-reflective tool. As a sales professional, regularly asking yourself “why” helps keep you accountable. For example, Why pursue this deal? Why should I agree to disclose commercials at this stage? Why should the customer consider me over the incumbent?…and so on.
Using “why” as a lens to assess your actions ensures that you remain focused, deliberate, and aligned with your goals. It becomes a guide, prompting you to question the rationale behind your choices and refining your strategy.
5. Answering with a Question: The Ultimate “Why” Hack
Always answer a question with a question. This helps you take a deeper cut, broaden your understanding of the customer’s context, and gives you time to think. It also makes you look like someone who is curious about the customer!
When a customer asks, “Why is your price higher than the competition?” the instinct may be to launch into a detailed explanation. However, answering with a question, such as “Why do you feel our price is higher?” or “What makes you think that way?” can often reveal valuable insights. It shifts the focus back to the customer, prompting them to disclose information that can be crucial for negotiating or reframing the value proposition.
Yet again, Why “Why”?
Think of “why” as the Swiss knife in a salesperson’s toolkit. It’s more than a question—it’s a multi-functional tool for discovery, a way to shift perspectives, and a lens for self-assessment. By refining how and when you wield “why,” you can avoid coming off as an interrogator while still uncovering deep insights.
So, the next time you find yourself reaching for a pat answer or simple explanation, remember to pause and ask, “Why not dig deeper?” Because in sales, as in life, those who dare to ask “why” often uncover the real answers—the kind that close deals, build relationships, and, occasionally, sell a pen to the Wolf of Wall Street.