You've likely asked your buyer at some point, "What's keeping you up at night?" While it’s a well-intentioned question designed to uncover pressing challenges, it’s become a bit of a cliché. Your buyers have heard it so often, it might not spark the genuine, reflective responses you need to create real value. If you want to understand their critical challenges, fears, and aspirations, it’s time to reframe the conversation.

In this article, you'll explore 10 fresh ways to get your buyer to open up about what truly matters to them. You’ll not only uncover their core needs and tough questions but position yourself as a trusted partner who understands their business on a deeper level. Ready to dive in? Let’s go.

1. "What obstacles are preventing you from achieving your top priorities?"

This shifts the conversation from abstract worries to tangible roadblocks. By asking about their top priorities, you gain insight into their key goals, and by focusing on obstacles, you create an opportunity to position your solution as the remedy.

Why it works: It feels proactive and constructive. Instead of dwelling on problems, you’re asking them to identify the gaps that are holding them back from success.

2. "What’s the most significant risk you're worried about right now?"

This question brings to the surface specific risks or threats your buyer sees looming, helping you understand where their anxiety lies. It’s targeted and direct, allowing you to delve into potential deal-stopping issues early.

Why it works: Buyers often have clear ideas about risks they want to mitigate, and this question demonstrates that you understand the unpredictable nature of business.

3. "Where do you see potential blind spots in your current strategy?"

Every business leader knows they have blind spots—they just might not be willing to admit it upfront. By prompting them to think critically about their strategy, you open the door to conversations about how your solutions might address those unknowns.

Why it works: Buyers appreciate when a sales conversation shifts from generic probing to a more insights-driven, strategic approach. This shows you’re thinking like a partner, not just a vendor.

4. "How are you planning to navigate the next 6-12 months in this volatile market?"

This question taps into their uncertainty about the future. You’re acknowledging the turbulence in their industry and helping them think about how to respond to it.

Why it works: It connects you directly to the shifting external environment, where nearly every industry is facing disruption. By focusing on the future, you signal that you're ready to help them stay ahead of changes.

5. "What challenges are keeping you from scaling or growing as fast as you’d like?"

This question zeroes in on growth and scalability, topics that are always top-of-mind for B2B leaders. You’re asking about aspirations and roadblocks at the same time, making it easy to tie your solution to their growth goals.

Why it works: Everyone wants to grow faster, and by positioning your question this way, you help them think not just about their problems but their aspirations.

6. "In what areas are you experiencing decision paralysis?"

Decision paralysis is a common struggle in complex B2B organizations. This question allows buyers to express their frustrations with internal bottlenecks, misaligned teams, or overwhelming choices.

Why it works: It shows empathy for their internal struggles. According to research by Gartner, 40 percent of B2B buyers cite internal misalignment as a key reason for decision delays. By asking this, you’re offering to help guide them through a tough decision-making landscape.

7. "What’s holding you back from taking action on opportunities you know are there?"

This shifts the focus from problems to unrealized opportunities. Buyers often know where opportunities exist but may feel constrained by resource gaps, risk aversion, or lack of direction. This question helps you dig into those issues.

Why it works: It’s an empowering question, putting a positive spin on their potential while also acknowledging the barriers they face in seizing opportunities.

8. "How are you addressing the tension between short-term needs and long-term strategy?"

Every B2B leader wrestles with balancing immediate demands with strategic goals. This question forces them to articulate the conflict between short-term firefighting and long-term planning, giving you insights into where they might need help.

Why it works: It’s thoughtful and nuanced. Buyers know that short-term wins can sometimes undermine long-term success, and this opens a conversation on how to align those needs.

9. "What buyer or market shifts are keeping you on your toes?"

This taps into the external pressures they’re feeling, whether it’s shifts in buyer behavior, industry trends, or competitive dynamics. It’s less about internal challenges and more about how external forces are reshaping their priorities.

Why it works: It positions you as someone who understands the broader market context, not just their company’s challenges. This resonates well with buyers focused on staying competitive in rapidly evolving environments.

10. "What metrics do you feel aren’t moving in the right direction right now?"

By focusing on metrics, you appeal to their analytical side. Every B2B leader has KPIs that they’re closely monitoring, and this question helps uncover pain points that are often tied to measurable outcomes.

Why it works: It’s a specific, numbers-driven approach that helps you focus on concrete areas where they need improvement. A McKinsey & Company study shows that 72 percent of B2B buyers are increasingly focused on data to guide their decision-making .

The next time you’re in a conversation with a buyer, go beyond the overused "What’s keeping you up at night?" and try these fresh approaches. Not only will you uncover deeper insights, but you’ll position yourself as a strategic partner who truly understands their unique needs. And in today’s crowded market, that kind of differentiation is priceless.

Ready to implement these questions in your next sales conversation? Keep testing and refining your approach, and watch how it transforms your buyer relationships.

Sources:

1. Gartner, "Why B2B Buyers Experience Decision Paralysis."
2. McKinsey & Company, "How Data is Shaping B2B Decision-Making."