Originally published January 2022. Updated June 2026.
Asking the right questions during the discovery process is critical. It’s why we created the DRIVE information-gathering framework—to give sales professionals a blueprint for what they need to know. But you aren’t done asking questions once you have the information outlined in DRIVE. In truth, as a sales professional, you’re never done asking questions.
Are you asking bold questions? Those are the questions that likely make you a little uncomfortable. They’re the questions you know you should ask to get the best results, but that you’ll be tempted to skirt around or soften.
Not every question needs to be a bold question. In fact, it shouldn’t be. But if you’re avoiding the bold questions altogether, you’re doing yourself and your prospect a disservice.
WHY ASK BOLD QUESTIONS?
If bold questions are so uncomfortable, why bother? Like many things that are slightly uncomfortable (seatbelts, bike helmets, colonoscopies), you’ll end up in better shape when you embrace bold questions.
By facing potentially difficult situations head-on, whether that’s asking about a missed deadline or whether a specific person really needs to be involved in the decision-making process, you stand to gain advantages. Bold questions keep you from spending precious time on deals that won’t close. They help your prospect or client think differently about a challenge or opportunity.
Bold questions can open the door to more, deeper conversations about where your client is headed. Ultimately, having the discussions that result from bold questioning improves interpersonal bonding between you and your client.
WHAT KEEPS US FROM ASKING BOLD QUESTIONS?
What is it that makes us so uncomfortable about asking bold questions if they’ll help us and our prospects in the long run? Some of us aren’t used to being direct.
People may feel that, by asking bold questions, they’re being rude or aggressive. Keep in mind the teachings of Craig Wortmann from the Kellogg School of Business. To be effective at being bold, you need to balance it with humility. The stronger your question is, the more you’ll need to increase your warmth.
Another reason we fear being bold is that we don’t like rejection. Remember that it’s better to get a fast no than a long maybe. Keep perspective—don’t equate objections with rejections.
People often make objections because they’re seriously considering your product or service. It’s better to proactively uncover objections you suspect are lurking beneath the surface than get tripped up by them when you’re further along and they can really slow things down.
Bold questions are those that force our prospect to confront a pain point, and pain is something we as humans like to avoid, even when it’s someone else’s. Being bold, however, means not shying away from the pain.
It’s why we teach our clients to ask their prospects not only “why are you doing this?” but also “what happens if you don’t?” Our instinct is to quickly go from a pain point to how our product or service can keep that from happening, but it’s important to fully explore those challenges, and even sometimes revisit them when a deal gets off track.
Asking bold questions requires empathy, trust, and vulnerability. It’s important that we build trust between ourselves and our prospects—it’s what earns us the right to ask bold questions.
Remember to balance tough questions with warmth. You’re not asking bold questions just for yourself—saving time and delving deeper into challenges helps your prospect as much as it does you.
CONVERGENT VERSUS DIVERGENT QUESTIONS
Bold questions feel different than the kinds of questions we’re used to asking because they tend to be divergent questions instead of convergent questions.
Convergent questions are about narrowing down or homing in on a detail. They usually have a single answer. Who needs to be part of this discussion? What’s the biggest problem you’re facing?
Divergent questions, on the other hand, encourage broader thinking and often lead to more questions. How could the procurement process be approached in a different way? What are the potential outcomes of using this solution? These are bold questions, but they also result in some of the best discussions.
SOME BOLD QUESTIONS TO GET YOU STARTED
Are you ready to start asking some bold questions? Here are some to get you going. Think about how these differ from more typical questions and how you could apply the same approach to some of the other questions you commonly ask.
Bold Questions for Getting to Know Your Prospect and Their Organization
- My preferred communication is via text. What do you prefer?
- What was the last solution/product/tool you wanted but couldn’t get approved? What happened to derail the purchase?
Bold Questions for Addressing Objections and Obstacles
- “Does anything about the product concern you?”
- “Help me understand why we continue to miss deadlines and push things out?” (Technically, this isn’t a question, but it’s a way to prompt the conversation with more warmth.)
Bold Questions When Introducing Others to the Decision-Making Process
- When a prospect says they need approval from someone else, ask “What does this person care about? How does this product relate to their job or role?”
- “If this other decision-maker says ‘no’ and you say ‘yes,’ who wins? If it’s you, are you sure you want to have this person involved?”
Bold Questions for Clarification
- “You say you need this done ASAP. What do you mean by ASAP?”
- “I’m surprised to hear you say X. Typically people in your role say Y. What was the reason for your response?”
It’s okay if some of these make you squirm. Being bold isn’t something you do once and are done with. Like any skill, it takes practice. The more bold questions you ask, the more comfortable you’ll become in asking them.
Practice asking bold questions when doing roleplays with your team. Try some out on your kids. And let us know how it goes.
Being bold doesn’t mean going solo. Reach out to us at mastery@maestrogroup.co to learn how we can make it easy.