podcast ·Nov 14, 2024

Strategies for Asking Better Questions in Sales with Curt Tueffert

by Drewbie Wilson

Episode 48: Strategies for Asking Better Questions in Sales with Curt Tueffert

"They don’t care how much you know until they know how much you care." — Curt Tueffert

In this episode of Call The Damn Leads, I got the chance to chat with Curt Tueffert, a sales veteran who knows a thing or two about what makes a great salesperson. Curt shares his insights into what he considers the most powerful tool in any sales pro’s arsenal: the art of asking better questions. With decades of experience and a wealth of wisdom, Curt shows us how curiosity, follow-up, and the ability to pivot can make all the difference in today’s competitive sales environment.

From hilarious sales stories to hard-earned lessons, Curt breaks down why curiosity and persistence are essential for anyone looking to build long-term client relationships. Whether you're a seasoned pro or just starting, this episode will help you rethink how you approach your conversations with prospects and clients.

Key Takeaways

Sales Success Hinges on Curiosity and Questioning

Curt highlights that a successful sales approach is more about understanding the client than pitching products. By always being curious, you not only build rapport but uncover the real needs driving your client's decisions.

Follow-Up as a Relationship Builder

In Curt's experience, following up consistently, whether through birthday messages or handwritten notes, keeps your name top of mind for clients. He even shared a unique tactic—sending half-birthday cards to make a memorable impact and encourage calls back from clients.

The Importance of Continuous Learning

As Curt puts it, great salespeople are “students of the game.” By dedicating time to learning and adapting to industry shifts, especially when it comes to AI or changing tech, you stay relevant and prepared for what’s next.

Embrace Simplicity with Your Follow-Up System

You don’t need an advanced CRM to manage client relationships. Start with what you have—a simple spreadsheet or calendar works well if used consistently.

Mastering the Art of Personalized Communication

Drewbie and Curt both emphasize the importance of keeping client communication personal. Curt's tactic of collecting client birthdays and sending half-birthday cards is a standout example, reminding clients they’re valued without pushing for a sale.

Expanded Insights into Asking Better Questions

Building Strong Connections Through Curiosity

One of the standout messages Curt shared was the idea of always being curious. Instead of launching into a pitch, he recommends taking the time to get to know the prospect and uncover their true needs. This shift, from pitching to asking thoughtful questions, positions you as a trusted advisor rather than just another salesperson. Curt suggests asking questions that dig deeper into your prospect’s industry or their unique challenges.

Pro Tip: Next time you’re on a call, try opening with a question like, “What’s one challenge you’re facing in your business right now?” and really listen to their answer. You’ll likely gain insights you can use to tailor your approach to them.

Follow-Up with a Personal Touch: Birthday and Half-Birthday Cards

Curt shared his follow-up secret weapon—half-birthday cards. By celebrating milestones outside of typical holiday messages, Curt is able to make a genuine connection that stands out in a prospect’s mind. This is about more than sending cards; it’s about using creative, consistent touchpoints that keep you memorable without being salesy.

Try This: Implement a small ritual like a monthly review of your client list and schedule out unique follow-ups. Whether it’s a quick email, a birthday video, or a handwritten note, showing thoughtfulness in your follow-up demonstrates to clients that they’re more than a number.

Embracing AI Without Losing the Human Element

As Drewbie and Curt discussed, AI is changing the sales landscape, but it’s not a replacement for the empathy, curiosity, and adaptability that human salespeople bring. Instead, Curt suggests using AI to handle the repetitive tasks, leaving you free to focus on relationship-building. For example, AI can help you analyze client data, but it’s your job to use that data to ask thoughtful questions and guide the client toward solutions.

Practical Strategy: Use AI as a research tool to get a quick snapshot of your client’s industry and recent trends. Armed with this insight, you can ask more specific, value-adding questions during your sales conversations.

Consistency Is Key to Building Trust

Curt has found that consistency in follow-up is one of the most important habits any salesperson can develop. Often, it’s not the first or second touchpoint that closes the deal but the tenth or eleventh. Clients are busy, and building trust takes time, which is why Curt emphasizes the importance of creating a simple, sustainable system for follow-up.

Even if you don’t have a fancy CRM, a basic system like a spreadsheet or calendar reminder can be just as effective if used consistently. The key is to set a schedule that works for you and to follow it diligently.

Easy Routine: Schedule a weekly follow-up review every Friday. Go through your list of prospects and clients, check when you last reached out, and plan a next step for each one. Over time, this practice keeps your leads warm and your name top of mind.

Final Thoughts

Curt’s advice in this episode is a reminder that the heart of sales lies in relationships. By asking thoughtful questions, following up in memorable ways, and always staying curious, you’re able to build stronger client connections and create a lasting impact. These simple, consistent actions add up over time, driving both sales success and personal growth.

Connect with Curt Tueffert:

Curt’s experience and insights have transformed how sales pros approach conversations and build long-lasting relationships. Check out more of his work and connect with him below!

Website: Peak Sales Strategy

Follow Curt on LinkedIn: Curt Tueffert