Questions > pitches. Every single time.
Here's why:
Pitching = talking at someone. You're telling them what you think they need. You're guessing.
Asking questions = understanding what they actually need. You're diagnosing before prescribing. You're building trust.
"What are you using now?"
Gets them talking about their current situation.
"What's working well? What's not?"
Helps you understand pain points without making them defensive.
"If you could change one thing, what would it be?"
This reveals their top priority.
"What happens if you don't solve this?"
Helps them realize the cost of inaction.
"What would success look like for you?"
Lets them paint the picture of what they actually want.
When your friend asks for advice, you don't just start giving solutions. You ask: "What's going on? What have you tried? What do you think you want to do?"
That's the same approach. You're diagnosing before prescribing.
The Truth:
Great salespeople don't have the best pitch. They ask the best questions. When you understand what someone actually needs, selling becomes easy.
Why Strong Questions Do More Than Gather Information:
They help you close the sale. When you ask the right questions, you uncover what the client actually needs—and your solution becomes the obvious answer, not a hard sell.
They demonstrate your expertise. When you ask things the client hasn't thought of yet—questions about timelines they hadn't considered, requirements they hadn't anticipated, scenarios they hadn't planned for—you position yourself as someone who truly understands their world.
They increase client confidence. A prospect who feels deeply understood is a prospect who trusts you. The right questions make them think, "This person actually gets what we're dealing with."
They reinforce that B2B sales is solving business problems. Every great question pulls the conversation away from features and price and toward impact. That's where real deals are made.
Action Step:
This week, practice asking more questions than you make statements. See how long you can go before offering your opinion. Watch what happens.
Not all questions are created equal. There's a natural progression that great salespeople follow—a hierarchy that takes you from surface-level small talk to deep, deal-defining conversations. Think of it like peeling an onion. Each layer gets you closer to the core of what the prospect truly needs.
Level 1: Surface Questions
These are your openers. They establish context and get the conversation flowing. They're easy to answer and don't require vulnerability. Most salespeople stop here—and that's why most salespeople struggle.
Examples: "What are you using right now?" "How did you hear about us?" "What's your role in this decision?" "How many people are on your team?"
Surface questions are necessary, but they're just the starting point. You need them to establish rapport and gather basic facts. But if you only ask surface questions, you'll only get surface answers—and surface answers don't close deals.
Level 2: Problem Questions
Now you're getting into the real conversation. Problem questions uncover pain points, frustrations, and gaps. They reveal what's not working and why the prospect is even talking to you in the first place.
Examples: "What's not working well with your current setup?" "Where do you feel like you're losing the most time?" "What's the biggest challenge your team is facing right now?" "What made you start looking for a new solution?"
Problem questions require the prospect to be a little vulnerable. They're admitting something isn't great. That's why trust matters—if they don't trust you yet, they'll give you surface-level answers to problem questions. Build rapport first, then dig.
Level 3: Impact Questions
This is where most salespeople never go—and it's where the real money is. Impact questions help the prospect understand the consequences of their problem. They make the pain real and urgent. They transform a "nice to fix" into a "need to fix."
Examples: "What happens if you don't solve this in the next six months?" "How is this affecting your team's morale?" "What does this cost you per quarter?" "How is this impacting your ability to hit your goals?"
Impact questions don't just help you sell—they help the prospect. Many people don't fully grasp how much a problem is costing them until someone asks them to quantify it. You're not creating urgency. You're revealing urgency that was already there.
Level 4: Vision Questions
The final level. Vision questions flip the conversation from problems to possibilities. They get the prospect to articulate what their ideal future looks like—and in doing so, they essentially describe the solution you're about to offer.
Examples: "If you could wave a magic wand, what would this process look like?" "What would it mean for your team if this problem were completely solved?" "What would success look like for you 12 months from now?" "If we could take this off your plate entirely, what would you do with that freed-up time?"
When a prospect answers a vision question, they're selling themselves. They're painting a picture of a better future—and your job is simply to say, "That's exactly what we do. Let me show you how."
Real Talk from Katherine:
I was on a call once with a hospital administrator. I started with surface questions—how many facilities, what's the current security setup. Then I moved to problem questions—what's not working, where are the gaps. When I got to impact questions and asked, "What happens when there's a security incident and a nurse doesn't feel safe walking to her car?"—there was a long pause. Then she said, "We lose nurses. We've lost four this year to hospitals that feel safer." That pause told me everything. The impact was huge, and she was realizing it in real time. I never had to "sell" her. The questions did the selling for me.
Just as important as knowing what to ask is knowing what NOT to ask. Certain types of questions kill conversations, break trust, and make you look like every other salesperson the prospect has ever tuned out. Here are the ones to avoid:
Yes/No Questions
"Are you happy with your current provider?" Answer: "Yes." Dead end. You learned nothing. Conversation over.
Instead ask: "What's working well with your current provider, and what would you change if you could?" Now they're talking. Now you're learning.
Leading Questions
"Don't you think it would be great to save 40% on your costs?" This isn't a question. It's a pitch disguised as a question. Prospects see through it immediately, and it erodes trust.
Instead ask: "How would a 40% cost reduction impact your department's goals this year?" Same topic, but now you're inviting them to explore the value on their own terms.
Assumptive Questions
"So when would you like us to start implementation?" Whoa. Nobody said yes yet. Jumping ahead like this makes prospects feel pressured, and pressure kills deals.
Instead ask: "Based on what we've discussed, does this feel like it could be a fit for your team?" Let them arrive at the conclusion. Guide, don't push.
Rapid-Fire Questions
"What's your budget? What's your timeline? Who else is involved? When do you need to decide?" Asking questions one after another without pausing makes the conversation feel like an interrogation, not a dialogue.
Instead: Ask one question. Listen fully. Respond to what they said. Then ask the next one. Great questioning is a conversation, not a questionnaire.
I want you to leave this module with a tangible tool you can use starting tomorrow: your personal question bank. These are 10 powerful questions organized by the stage of the sales conversation. Write them down. Practice them. Make them yours.
Discovery Stage (3 questions)
1. "What's driving the need for this right now? Is there a specific event, or are you planning ahead?"
2. "Walk me through your current process. What does a typical day look like when you deal with [the problem]?"
3. "What's already been tried? What worked and what didn't?"
Qualifying Stage (3 questions)
4. "Who else is involved in this decision, and what do they care about most?"
5. "What does the timeline look like? Is there an event or deadline driving this?"
6. "What would need to be true for you to feel confident moving forward?"
Presenting Stage (2 questions)
7. "Based on what you've told me, here's what I'd recommend. What stands out to you, and what raises questions?"
8. "On a scale of 1 to 10, how well does this match what you're looking for? What would make it a 10?"
Closing Stage (2 questions)
9. "Is there anything we haven't covered that would help you feel 100% confident in this decision?"
10. "What would you need from me to take the next step?"
Real Talk from Katherine:
When I first started in B2B sales, I thought the goal was to have the best answers. I'd prepare for calls by memorizing product specs, competitive advantages, and pricing tiers. But the calls that went the best were the ones where I barely talked about the product at all. Instead, I asked questions. I let the prospect talk. And by the end of the call, they'd say something like, "I feel like you really understand what we're dealing with." I hadn't even pitched yet! The questions did all the work. Now I spend 80% of my call prep writing questions, not practicing pitches. That shift alone doubled my close rate.
Build your question bank this week:
Write 5 questions you could use in a discovery conversation—or everyday conversations. Use the framework:
2 Discovery Questions
“What’s driving the need for this right now?” “What does success look like on your end?”
2 Clarifying Questions
“Help me understand what you mean by that.” “Can you tell me more about what happened?”
1 Commitment Question
“What would need to be true for this to make sense for you?”
The person who asks great questions runs the conversation—without it feeling like an interrogation. Practice these five. They’ll serve you in interviews, in discovery calls, and in life.
What you just learned shows up differently depending on which sales path you're exploring. Click your path to see how this applies to you specifically.
B2B questions focus on business impact, stakeholders, timelines, and budgets. Your discovery calls are more structured in B2B because you're dealing with longer sales cycles and multiple decision-makers. Every question should serve a purpose: either qualifying the opportunity, uncovering the real problem, identifying who else needs to be involved, or understanding the decision-making process.
Great B2B discovery questions sound like this: "Who else will be involved in evaluating this, and what does each person care about most?" "What does your approval process look like once you decide to move forward?" "How does this investment compare to the cost of the problem you're dealing with today?" "If we can demonstrate a clear ROI in the first 90 days, does that change how you think about the budget?"
In B2B, your questions also demonstrate your expertise. When you ask about regulatory compliance, seasonal demand fluctuations, or integration with their existing tech stack, you're showing that you understand their world. You're not just a salesperson—you're a consultant. The questions you ask tell the prospect whether you're going to waste their time or actually help them solve something.
One B2B-specific tip: always end your discovery calls with a "mutual action plan" question. "Based on what we've discussed, here's what I think the next steps should be. Does that match what you're thinking?" This keeps the deal moving and shows you're organized—something B2B buyers value enormously.
Before you move on, let's make sure the key concepts really clicked. Answer all questions correctly to unlock the next lesson.
1. What are the four levels of the Question Hierarchy, in order?
2. Why are yes/no questions a problem in sales conversations?
3. What do Impact questions accomplish that Surface and Problem questions don't?
4. According to Katherine, what should you spend 80% of your call prep time on?
5. Why is asking questions better than pitching in sales?
Complete the Knowledge Check above to unlock the next lesson.
Week 2 Wrap-Up →