Most Sales Conversations Fail Because the Salesperson Asks the Wrong Questions at the Wrong Time. Buyers Don’t Want to Be Sold; They Want to Be Understood. When You Match Your Questions to Their Stage in the Buying Journey, You Establish Trust, Reveal Urgency, and Guide the Sale Without Being Pushy. The post Why Your Sales Questions Need to Match the Buyer’s Journey first appeared on SteveBizBlog.
We’ve all had those conversations where a prospect nods, thanks you for your time, and disappears. No callback. No follow-up. Just a quiet fade.
Most of the time, that silence isn’t about your price, pitch, or product. It’s because your questions didn’t match where they were in their buying journey. You were talking about diagnosis when they didn’t even think they were sick yet. Or you jumped to ROI before they felt the pain.
Great salespeople don’t just pitch. They guide. They meet prospects where they are emotionally and mentally, then walk them forward step by step.
Pain Is the Starting Line
David Sandler, creator of the pain funnel, built his whole sales system around one idea: people buy to avoid pain, not to chase pleasure.
Behavioral economist Daniel Kahneman later proved the same concept in his Nobel-winning work on loss aversion: people will do roughly twice as much to avoid pain as to gain pleasure.
That’s why “painting the pain” for your prospect is more powerful and why leading with benefits rarely works. If the buyer doesn’t feel the cost of staying stuck, there’s no reason to change.
The buyer’s Journey
You can’t force pain. You have to meet buyers where they are and help them uncover it at their own pace. That’s where the five stages of the buyer’s journey come in:
- Latent pain
- Active pain
- Solution development
- Evaluation
- Decision
Each stage requires a different series of questions and tone.
How to Tell Where Your Buyer Stands
Before you can ask the right questions, you have to know which stage your buyer is actually in. When you first start talking with a prospect, either at a networking event or on a discovery call, it doesn’t take long to get a sense of where they are. Ask an open-ended question like, “How are things going in your business right now?” or “What’s been taking most of your attention lately?” or my favorite, “What’s keeping you up at night?” Then listen closely.
- If they describe mild annoyances or vague frustrations, they’re probably in latent pain.
- If they mention specific problems or measurable losses, you’re hearing active pain.
- When they start exploring ideas or comparing tools, you’ve entered solution development or evaluation.
The more emotional detail and urgency you hear, the further along the buyer is. Your job isn’t to push them forward; it’s to match your next set of questions to the point where they are in the buyer’s journey and guide them naturally from awareness to action.
Once you’ve asked those first few questions, you’ll know where to start. Don’t assume every buyer is at the top of the journey. If they’re already feeling real pain or exploring solutions, and you start back at square one, you’ll only frustrate them. The goal is to meet them where they are, neither ahead of nor behind, and guide the conversation from there. Let’s examine how each of the five stages typically unfolds and how the right questions naturally help move the buyer forward.
1. Latent Pain: “It’s Not a Problem Yet”
What’s happening:
Meet Mike, the owner of a small HVAC company with six techs and two trucks. He’s been in business for 10 years. Most of his work comes from word of mouth and repeat customers. Business is steady but flat.
Summer’s ending, and calls are slowing down. He figures it’s just the season. The website is dated, marketing efforts are minimal, and dispatching still occurs on a whiteboard. But it’s fine, until it’s not.
Your role:
You own a service company that helps contractors schedule jobs, track maintenance contracts, and automate billing. When you meet Mike at a chamber lunch, he’s polite but distracted.
This is the latent pain stage, also known as the “nagging toothache” stage. He senses minor frustrations but hasn’t defined them as problems.
Your goal:
Spark curiosity without pressure. Get him thinking about what could be better, not what’s broken.
Questions that work:
- “How are you keeping track of recurring maintenance customers?”
- “Do you ever get double-booked during the busy season?”
- “What’s your plan if one of your trucks goes down mid-week?”
- “If you could free up a few hours a week, where would you use that time?”
Each question nudges awareness. You’re connecting your solution to the world he already knows, not pitching something foreign.
Buyer mindset:
“I’m doing okay. Maybe I’ll look into that later.”
Your job is to plant the seed that “later” could cost him more than he realizes.
2. Active Pain: “Something’s Got to Change”
What’s happening:
A few months later, winter hits. Calls begin to pile up, schedules overlap, and two customers get missed entirely. One posts a negative review online. Mike is frustrated.
He’s no longer just annoyed; he’s feeling real pain. Jobs are slipping, and revenue is being lost.
Now he’s ready to talk.
Your role:
You reconnect and start asking diagnostic questions, not to sell, but to help him describe the pain in his own words.
Questions that work:
- “How many jobs fell through the cracks this month?”
- “What happens when a tech calls in sick? How do you adjust?”
- “How much time are you spending on scheduling every week?”
- “What does a missed job cost you in terms of reputation or repeat work?”
These questions make the invisible visible. The more Mike quantifies the pain, the more he owns it. Silence matters here. Ask, then pause. Let him think. Let him feel the frustration.
Buyer mindset:
“This is costing me real money. I need to fix it.”
Now you’re aligned emotionally. He’s in motion, and you’re the guide.
3. Solution Development: “What Should I Do About It?”
What’s happening:
Mike’s started Googling “HVAC scheduling software.” He’s talked to another contractor who uses one. He’s gathering information, trying to understand his options.
He’s no longer debating whether to change; he’s debating how to change.
Your role:
Become his thinking partner. Not a pitchman. Not the hero.
This is where you help him define the right problem before chasing the wrong fix. You co-create clarity.
Questions that work:
- “What would success look like for you in 90 days?”
- “If nothing changed, how would that affect your spring season?”
- “What’s most important to you? Reducing chaos, freeing up time, or improving customer experience?”
- “Who on your team would benefit most from having this kind of system?”
These questions shift the focus from pain to possibility. He’s now imagining relief: fewer scheduling headaches, faster payments, happier customers.
You can now outline a solution together. Perhaps a two-phase rollout: dispatch automation first, followed by billing integration later. You’re shaping the plan with him, not at him.
Buyer mindset:
“I know I need something. I just want to make sure it fits.”
You’re helping him visualize what that fit looks like.
4. Evaluation: “Who Can I Trust to Get This Right?”
What’s happening:
Mike has narrowed his choices to you and one competitor. He’s comparing pricing, support, and reviews. His office manager, Sara, is now part of the discussion, as she handles invoicing and scheduling.
At this point, logic meets emotion. He wants a fix, but he also wants confidence that he won’t regret his decision.
Your role:
Understand what truly matters to him. Don’t assume it’s just the price. It might be reliability, responsiveness, or peace of mind.
Questions that work:
- “What’s most important to you about who you work with?”
- “What would make this transition easy for your team?”
- “What worries you most about making a change like this?”
- “What would you need to see to feel confident moving forward?”
These questions reduce uncertainty. You’re giving him a space to voice doubts instead of hiding them.
You might share a short success story: “A contractor your size told me his weekly scheduling time dropped from three hours to thirty minutes within two weeks.” That’s not a pitch, it’s reassurance.
Buyer mindset:
“I like this solution. I just need to be sure it’s the right move.”
Trust closes this stage. Once he feels heard, price becomes secondary.
5. Decision: “Let’s Do It”
What’s happening:
Mike is almost there. He’s done the math, talked to his team, and mentally said yes, but some level of hesitation still lingers.
“What if we can’t get the guys to use it?” “What if setup is too hard?”
Normal doubts. They’re not objections to overcome. They’re fears to calm.
Your role:
Simplify the path forward. Reduce risk. Reinforce partnership.
Questions that work:
- “Would it help if we started with just the dispatch automation process first?”
- “Who should we include in the kickoff so everyone’s on board?”
- “When would you like to start seeing results?”
- “What’s the best way to make the first week go smoothly?”
Each question builds momentum while keeping him in control. You’re not closing. You’re confirming.
He says, “Yeah, let’s start with the dispatch automation process first and go from there.” That’s a win.
Buyer mindset:
“I feel good about this. Let’s make it happen.”
You’ve guided him from vague discomfort to confident action without ever “selling.”
Why Matching the Journey Matters
Most small businesses selling to other small businesses don’t have the luxury of large sales teams or lengthy sales pipelines. The owner is usually the salesperson, the technician, and the bookkeeper all at once.
That means every conversation counts. When your questions match where the buyer actually is:
- You stop wasting energy explaining solutions to people who aren’t ready.
- You build trust faster because your tone fits where they are in the buyer’s journey.
- You shorten the cycle without adding pressure.
Instead of pushing, you’re guiding. Instead of convincing, you’re helping them discover what’s true for them.
The Bigger Truth: Stop Selling, Start Guiding
When you align your questions with the buyer’s stage, you shift from being a “product pusher” to a “trusted advisor.”
You’re not trying to be the hero. The customer needs to always be the hero. You are their Yoda, and your customer is Luke Skywalker. You’re the guide who helps them recognize the Empire they’re fighting and hands them the lightsaber.
A few reminders:
- Pain drives action. People buy to relieve discomfort, not to chase pleasure.
- Emotion precedes logic. They must feel the gap before they can analyze it.
- Questions reveal truth. The right ones invite reflection instead of resistance.
- Patience builds urgency. The longer you stay in their story, the deeper the commitment to change.
Once you learn to ask questions that fit the moment, you will see your closing rate rise. Not because you’re better at selling, but because your buyers are better at deciding.
Putting It All Together
Here’s a quick map you can keep handy:
| Stage | Buyer Behavior | Your Focus | Question Style |
| Latent Pain | Mild frustration, no urgency | Create awareness | “What’s working well right now, and what’s not?” |
| Active Pain | Recognized problem, seeking answers | Diagnose & quantify | “How much is this issue costing you?” |
| Solution Development | Researching & comparing options | Advise & clarify | “What would success look like if we fixed this?” |
| Evaluation | Comparing vendors | Differentiate with trust | “What would make this easy for your team?” |
| Decision | Ready but cautious | Simplify & reassure | “What’s the best next step to move forward?” |
It’s not about memorizing scripts. It’s about listening and adapting. The buyer’s words reveal exactly where they stand. You just have to hear it.
Conclusion
Before your next sales conversation, take a moment to ask yourself: Where is this buyer in their purchasing journey?
- If they are unaware, spark curiosity.
- If they are hurting, help them explore it.
- If they are comparing, guide them through the noise.
When you do that, you stop chasing deals and start attracting decisions. Because the truth is, when buyers see both the pain of staying put and the relief of moving forward, they don’t need to be sold. They’ll sell themselves.
When you think about your last few sales calls, were your questions aligned with where the buyer actually was or where you hoped they were?
The post Why Your Sales Questions Need to Match the Buyer’s Journey first appeared on SteveBizBlog.
