1. What’s the Biggest Challenge Your Team is Facing Right Now?

Why Ask This? This question gets straight to the heart of their pain points. Understanding their top challenge helps you position your solution as the answer to their problem.

2. What Solutions Have You Tried Before?

Why Ask This? This reveals what hasn’t worked for them and why. It helps you avoid offering a similar approach and instead tailor your pitch to address their frustrations.

3. What Are Your Short-Term and Long-Term Goals?

Why Ask This? Aligning your solution with both immediate needs and future plans demonstrates that you’re thinking beyond a quick sale—you’re offering lasting value.

4. How Would Solving This Problem Impact Your Team or Business?

Why Ask This? This question uncovers the stakes and adds urgency to the conversation. It also helps you understand the emotional and financial drivers behind their decision-making.

5. Who Else is Involved in the Decision-Making Process?

Why Ask This? Identifying stakeholders early helps you avoid surprises later. You’ll know who to involve in future meetings and what concerns need addressing.

6. What’s Preventing You from Implementing a Solution Today?

Why Ask This? This helps identify potential roadblocks, whether it’s budget, internal buy-in, or competing priorities. You can then strategize on how to overcome these barriers.

7. What Does Success Look Like to You?

Why Ask This? Understanding their definition of success ensures you’re both on the same page. It also helps you craft a solution that aligns perfectly with their expectations.

Why These Questions Work

These questions focus on discovery, listening, and creating alignment. They help you gather actionable insights, qualify the lead, and build trust—all key components of a winning first meeting.

Ready to Transform Your SaaS First Meetings?

Start asking the right questions and watch your sales pipeline thrive. Book a discovery meeting today to see how we can help you master the art of SaaS first meetings.

Dive Deeper

For a complete guide to successful first meetings, check out The Perfect First Meeting by George Storm.