On Thursday, 13 March, The Win Academy hosted Deeper Insights, Stronger Stories, a high-energy and thought-provoking session designed to equip sales professionals with the skills to elevate their client conversations. Led by Martin Coburn, Managing Director of The Win Academy, and Ian Mackenzie, Executive Pitch Coach, this session explored the two most powerful levers in sales success: asking deeper, more insightful questions and crafting compelling, memorable stories.
Elevating Sales Conversations: The Power of Insightful Questions
Martin kicked off the session by framing the challenge facing sales professionals today. Buyers are more informed, more discerning, and have easier access to research than ever before. As a result, sales people must bring more to the table than just product knowledge, they must offer real insight, challenge assumptions, and help clients make better decisions.
Key themes included:
- Sales as a value exchange: The best sales conversations are built on trust, which is developed through meaningful, value-adding interactions rather than simply ‘convincing’ the client to buy. The more value a salesperson can provide through genuine insights, the more trust is built, creating long-term relationships rather than one-time transactions.
- Asking better questions: Most salespeople focus on fact-finding, but the real power lies in asking questions that challenge the client’s thinking and uncover opportunities they may not have considered. Thought-provoking questions can help clients reframe their challenges, leading to deeper conversations and stronger engagement.
- Navigating client mindset: Understanding what a client loves about sales conversations, and what they fear, helps sales professionals approach meetings with confidence rather than anxiety. The biggest fear? Wasting time on a conversation that doesn’t add value. Sales people must ensure that every interaction is meaningful, positioning themselves as problem-solvers rather than just vendors.
- Moving beyond transactional selling: Instead of focusing solely on pitching a product, sales professionals should position themselves as trusted advisors. This means being willing to challenge the client’s assumptions and explore new possibilities together. The most successful salespeople don’t just sell a solution, they help clients envision a better future.
- The 80/20 rule of sales conversations: 80% of a conversation might feel straightforward, but it’s the 20%, the unexpected challenges, concerns, and underlying motivations, that determines success. Exceptional salespeople focus on uncovering and addressing that 20%, whether it’s an unspoken fear, an unexpected barrier, or a deeper business objective.
One of the most impactful exercises during the session highlighted the importance of having a sharp, refined elevator pitch. Martin challenged attendees to describe their business in 30 seconds in a way that was both clear and compelling, a skill that, when mastered, makes a significant difference in sales success. He emphasised that a strong pitch should be concise yet impactful, making it easy for clients to understand why they should engage.
The Power of Storytelling in Sales
Ian took the stage to explore why storytelling is such a critical yet underutilised tool in sales. While data and logic are essential, they are rarely what wins deals. Instead, clients remember stories, particularly those that evoke emotion, build trust, and demonstrate real-world impact.
Key insights from Ian’s session:
- Why stories work: Facts are forgotten, but stories are 20 times more likely to be remembered. A compelling story provides context, helps the client see themselves in the scenario, and makes your message more engaging.
- Breaking the ‘generic pitch’ mold: Too many sales presentations begin with the same predictable formula: listing company size, client logos, and industry expertise. But these elements don’t differentiate a business. Instead, storytelling creates an emotional connection and makes a pitch stand out.
- Understanding the 20% that matters: Just like in conversations, sales professionals should focus their stories on the most critical 20%, the unique pain points, risks, and barriers that matter most to the client. A compelling story reassures the client that they are making the right choice.
Ian’s approach to storytelling left attendees with a clear challenge: Stop leading with data, and start leading with stories. The goal of every pitch should be to leave clients not just with facts, but with a feeling, one that builds trust and makes it easy for them to say yes.
Turning Insights into Action
Sales success doesn’t just come from knowing what to do, it comes from consistently applying the right strategies in real conversations. The insights from Deeper Insights, Stronger Stories provide a roadmap, but the real impact happens when they are put into practice. Whether it’s refining your questioning technique, sharpening your pitch, or embracing the power of storytelling, here are the key actions to take forward:
- Ask better questions: Challenge your client’s thinking and uncover opportunities they haven’t considered.
- Master your 30-second pitch: If you can’t clearly articulate your value in 30 seconds, your prospects won’t remember it.
- Don’t just present, tell a story: Use stories to make your message resonate and be remembered.
- Understand the 20% that matters: Focus on the deeper concerns, risks, and motivators driving your client’s decisions.
- Shift your mindset: Approach sales as a value-adding service rather than a competition to prove why you’re the best.
- The Hero’s Journey applied to sales: Borrowing from classic storytelling structures, Martin and Ian outlined a simple but powerful approach:
- The Starting Point: The client’s current reality and the challenge they face.
- The Conflict: The problem that’s standing in their way (their ‘villain’).
- The Resolution: How your service provides the transformation they need.
This framework helps sales professionals position their offering as the pivotal tool that enables the client’s success.
Continue the Conversation
As part of Deeper Insights, Stronger Stories, attendees had exclusive access to a complimentary 1-hour sales workshop, designed to help teams refine their approach to sales conversations and storytelling. Due to the overwhelmingly positive response, we’re extending this opportunity to a wider audience, so if you’re looking to sharpen your sales approach, now is the time to take advantage.
To learn more, reach out to martin@thewinacademy.co.uk
Looking ahead, our next event Culture Shift: A strategic event for senior leaders to rethink how to lead change that lasts will take place on 8th May. We’ll also be running a deep dive session on Winning the Pitch on 4th June, stay tuned for more details!
