Leveraging Paradoxes: Embracing the Unexpected in Sales Conversations

“Paradox is the source of a thinker’s passion and the thinker without a paradox is like a lover without feeling; A paltry mediocrity”- Soren Kierkegaard

Sales isn't just about presenting features and benefits—it's about creating moments that make your prospect sit up and think, "I didn't see that coming." The most effective sales conversations are the ones that surprise and the ones that challenge expectations. Embracing paradoxes is one of the most potent ways to do this: presenting two seemingly contradictory ideas that make perfect sense upon further reflection. Leveraging paradoxes isn't about confusing your prospect; it's about breaking through the noise and encouraging them to see things differently.

Every day, your prospects are inundated with pitch after pitch. Most of them look the same, sound the same, and feel the same. If you want to stand out, you need more than a clever opener or flashy slides—you need a perspective that makes them pause. This is where paradoxes come in: they create a mental "wedge," a moment where the prospect's expectations are disrupted, making them more open to the conversation you're guiding them through.

The Power of the Unexpected

Consider this paradox: "The more you push for a sale, the less likely you are to get it." The harder you push, the more resistance you build. By easing up, listening more, and asking open-ended questions, you'll find that prospects become more receptive. Highlighting this concept to a potential client can shift the entire dynamic of your interaction.

Think of it this way: when you push too hard, it's like trying to force open a door that only opens with a gentle touch. Prospects want to feel in control of the decision-making process. When you ease up, genuinely listen, and ask questions that invite them to share more, they feel heard and understood. This sense of control and understanding not only builds trust but also empowers them, making them more confident and secure in their decisions. This trust is the foundation of any successful sales relationship.

Another paradox to consider is: "To be more effective, you sometimes need to be less efficient." In sales, taking the time to deeply understand a prospect's needs may seem inefficient, but it's what leads to meaningful connections and, ultimately, the best partnerships. Prospects appreciate it when someone takes the time to slow down, actively listen, and offer tailored solutions rather than pushing for a quick close. It's about showing them that you're not just another salesperson trying to hit a quota—you're a partner invested in their success. This sense of partnership, where their needs are truly understood and respected, is what sets you apart in the sales process.

Think of it like hiking up a mountain. You could rush to the top, but if you do, you'll miss the views, the experience, and the journey. Slowing down lets you take in the surroundings, appreciate the details, and connect with the experience. In sales, slowing down allows you to connect with your prospects on a deeper level, understand their pain points, goals, and vision, and form true partnerships.

Slowing down doesn't mean being passive; it means being intentional. It means asking thoughtful questions, reflecting on the answers, and demonstrating genuine curiosity. This approach allows you to uncover the deeper motivations of your prospects—what really drives their decisions. When you take the time to understand these motivations, you can align your offering with their deeper needs and aspirations, creating a much stronger bond and a greater likelihood of a successful outcome. This alignment not only increases the chances of a successful deal but also makes your prospects feel more understood and cared for, strengthening your relationship with them.

Murakami and the Unexpected Twist

Haruki Murakami is one of my favorite fiction authors. I always recommend his books, especially Kafa by the Shore, 1Q84, and After Dark, a novel that takes place over one evening. Haruki Murakami's storytelling often involves paradoxical twists—those moments that seem surreal but resonate with a more profound truth. Imagine incorporating that approach into your sales narrative. Instead of presenting your product as a simple "solution," frame it as a "catalyst for change." This opens up a broader conversation where the prospect can envision not just fixing a problem but transforming how they operate entirely.

For example, you might say, "Our advertising solution isn't about fixing what's broken; it's about reimagining what's possible." This shifts the conversation from reactive problem-solving to proactive transformation, inviting a different kind of engagement. It's no longer about patching up issues—it's about envisioning a future where your product or service becomes a crucial part of their growth story.

When you position your offering as a catalyst for change, you invite the prospect to dream bigger. You're asking them to think beyond the immediate problem and consider the long-term impact. This kind of conversation is powerful because it moves away from transactional selling and toward building a vision together. It's about inspiring the prospect to see what's possible, not just what's practical.

Murakami's ability to blend the familiar with the surreal is what makes his stories so captivating. In sales, you can leverage a similar technique by blending the practical aspects of your product or service with the imaginative possibilities it enables. Invite your prospects to think of the "what ifs"—to visualize the transformative potential of what you're offering. This kind of thinking not only engages the logical side of their brain but also taps into their emotions, creating a connection that goes beyond the surface level.

“After nourishment, Shelter, and companionship, stories are the thing we need most in the world”- Phillip Pullman

Mike Rowe's Storytelling Approach

Another approach we could take is inspired by Mike Rowe's storytelling structure in his podcast, *The Way I Heard It*. Mike Rowe's podcast is much lighter and more easily consumed than Murakami's books but no less effective in their ability to engage their audience. Rowe has a unique way of presenting stories that seem familiar at first but are packed with unexpected twists that leave the listener intrigued and wanting more. Imagine using that approach in your sales conversations—starting with a scenario or problem the prospect is familiar with but then offering a surprising perspective or outcome that changes how they see the situation.

For instance, you could share a story about a client who initially struggled with the same issue the prospect is facing but found an unexpected path to success through your solution. This kind of storytelling, where the resolution is both surprising and insightful, helps prospects see beyond their current challenges and recognize new opportunities. It's about taking them on a journey that resonates emotionally and logically, making them think, "I didn't see that coming, but it makes perfect sense now."

The power of storytelling lies in its ability to make complex ideas more relatable and memorable. By using narratives that are both familiar and filled with unexpected twists, you can create an emotional connection with your prospect. This connection is what makes your message stick. When prospects can see themselves in the story, they're more likely to visualize the positive outcomes you're presenting and feel motivated to take action.

Using Paradoxes to Address Objections

Paradoxes are also powerful for handling objections. Picture this: a prospect says, "We don't have the budget for this right now." Instead of pushing back or walking away, you could respond, "I understand—sometimes the best investments are made when the timing feels imperfect." This response opens the discussion of future gains versus current constraints, encouraging the prospect to reassess their priorities.

Or, "I get it—it feels counterintuitive to spend more when you're trying to save, but sometimes the best way to increase your marketing effectiveness is through the right strategic investments." This helps the prospect rethink their resistance, turning what seems illogical into something that suddenly makes sense. By reframing the objection as a paradox, you invite the prospect to see the situation from a different perspective that might align with their long-term goals.

Consider another example: "I understand that it feels risky to invest now, but sometimes the biggest risk is doing nothing." This kind of statement challenges the prospect's current mindset and encourages them to think about the cost of inaction. It's not about forcing them to see your point of view—it's about gently guiding them to consider perspectives they may not have thought of before.

Using paradoxes to address objections isn't about tricking your prospect into agreement; it's about helping them see things differently. It's about shifting their mindset from focusing on the immediate cost or risk to considering the broader value and potential rewards. This approach fosters a collaborative atmosphere where you and the prospect work together to explore the best possible outcome.

“Judge a man by his questions rather than by his answers”- Voltaire

Creating Curiosity and Engagement

Using paradoxes effectively is about striking the right balance between intrigue and clarity. You want to provoke thought without causing confusion, and nudge the prospect to see things differently without making them defensive. When used well, paradoxes invite prospects to lean in, ask questions, and be part of the conversation. They're not just listening to your pitch but engaging with it.

Curiosity is one of the most powerful emotions you can evoke in a sales conversation. When a prospect is curious, they're open—they want to know more and actively participate. Paradoxes are a great way to spark that curiosity. They present something unexpected that doesn't quite add up at first glance, which invites the prospect to explore further.

Try crafting a few paradoxes for your next sales conversation. For example: "The less you try to close the sale, the more likely it is to happen," or "By stepping back, we can actually move forward faster." Use these paradoxes to start conversations or handle objections, and watch as curiosity takes hold. These moments of surprise create lasting impressions and open new doors to partnership.

Think about the power of a well-placed question. Instead of saying, "Our product will solve your problem," try something like, "What if the solution isn't about fixing what's broken, but about creating something entirely new?" This kind of question invites the prospect to think beyond their current situation and imagine possibilities they hadn't considered. It's not just about solving a problem—it's about expanding their vision.

This is where the anecdote about Henry Ford comes in. The story goes that Ford once said, "If I had asked people what they wanted, they would have said a faster horse." Though likely apocryphal, the quote captures a key insight about innovation: customers often have difficulty envisioning transformative change beyond the limitations of what they already know. When Ford was developing the Model T, people primarily used horses for transportation, and their desires revolved around improving the limitations of horse-drawn travel—speed, endurance, and care requirements. Ford, however, understood that simply making a "faster horse" wouldn’t solve the problem of transportation efficiency. Instead, he sought a disruptive innovation that would redefine personal mobility. This story highlights the importance of visionary thinking—sometimes, true innovation requires looking beyond what people think they need and imagining something entirely new that they haven’t even realized was possible.

Engaging a prospect's curiosity is about inviting them into a process of discovery. When they feel like they're part of the exploration, rather than just being told what to do, they're more likely to become emotionally invested in the outcome. Use paradoxes to invite them into this journey—to create an environment where questions are valued, and new possibilities are continuously being uncovered.

Applying Paradoxes in Practice

Next time you're in a meeting or on a call, try weaving in an unexpected statement that seems contradictory at first glance. Observe how the conversation shifts. Notice if the prospect leans in, asks a question, or pauses to think—these are signs they're genuinely engaged, considering what you're saying rather than just passively listening.

It's also important to be prepared for how prospects might react to paradoxes. Some may be intrigued right away, while others might need more context. The key is to be ready to explain and explore further. Paradoxes work because they disrupt the usual pattern of thinking, but they also require you to be adaptable—to follow the prospect's lead and dive deeper where needed.

Sales is about something other than fitting into the formula everyone else is using. It's about connection, creativity, and sometimes, a little bit of paradoxical magic. The unexpected is your ally—embrace it, and use it to your advantage. By leveraging paradoxes, you're not just making a pitch—you're opening up a dialogue, creating a space where real connections can happen. And in that space, anything is possible.

Paradoxes create moments of genuine engagement that can be transformative for you and your prospect. They allow you to stand out from the crowd, to be memorable, and to foster deeper connections. So, the next time you find yourself in a sales conversation, don't be afraid to lean into the unexpected. Use paradoxes to craft a narrative that is as engaging as it is insightful, and watch as your prospects become partners in the journey you're inviting them to take.