Closing More Sales by Asking Better Questions
Selling is all about connecting with people. As a salesperson, your job is to understand what motivates your prospects and identify how your product or service can help them achieve their goals. The best way to do that? Asking the right questions.
Questions open doors. They build rapport, uncover needs, and drive conversations forward. As sales expert Jeb Blount puts it: “Questions are the GPS system for sales professionals.” But simply asking any old question won’t cut it. To close more deals, you need to get strategic with your questioning.
In this post, we’ll explore why questions are so critical for sales success. We’ll also cover how to craft and sequence questions that uncover true buyer needs. Read on to learn techniques that will help you have more meaningful sales conversations.
Why Questions Are Key for Closing Deals
Let’s start with the basics – why are questions so important anyway? Here are a few key reasons:
Questions Allow You to Qualify Prospects
Not every lead is a good fit for your solution. Asking the right questions upfront helps you determine if it’s worth your time pursuing a deal.
For example, you can use questions to assess:
- Need. Does the prospect have a clearly defined problem or goal? How much of a priority is it for them to solve it?
- Authority. Does this person have decision-making power or influence?
- Budget. Does the prospect have a sufficient budget allocated to purchase your offering?
- Timeline. What is their timeframe for getting a solution in place?
If the answers reveal they aren’t a good fit, you can simply move on to better opportunities.
Questions Help You Discover True Needs
Prospects aren’t always transparent about why they might be interested in your product. They may mention one issue when the real problem is something entirely different.
Asking thorough, probing questions reveals the actual pain points and motivations driving their interest. This helps you tailor your solution pitch accordingly.
Questions Build Trust
Asking questions shows prospects you care about understanding their situation versus just making a sale. This builds trust in the relationship and makes them more receptive to your suggestions.
According to a CSO Insights study, buyers rate “trust in salesperson’s knowledge” as one of their top selection criteria. Questioning demonstrates your desire to listen versus just pitch.
Questions Set You Apart
Most salespeople charge ahead with a product-focused pitch before asking meaningful questions. By asking the right questions upfront, you show the buyer you’re willing to have a real conversation versus following a script.
This levels the playing field and makes you stand out from your competitors.
How to Ask Strategic Sales Questions
Now that we’ve covered why questions matter, let’s explore what types of questions you should be asking.
Here are five categories of questions that can help you close more deals:
1. High-Level Qualification Questions
As mentioned earlier, you want to start conversations by assessing if a prospect is truly a good fit.
Here are some examples of high-level qualification questions:
- What challenges is your team currently facing when it comes to [area your product addresses]?
- How much of a priority is it for you to solve these challenges in the next few months?
- Who from your organization is involved in these decisions?
- Do you have a budget allocated for a solution?
- What is your timeframe for getting this implemented?
If the answers indicate they aren’t ready to buy, politely decline to pursue the opportunity for now. You don’t want to waste your limited sales time on leads that won’t convert anytime soon.
2. Problem Questions
Next, drill deeper into the prospect’s specific problems. As sales expert John Barrows recommends, ask “why” questions to peel back the layers of what’s causing their pain points.
Here are some examples:
- You mentioned [problem]. Why is this an issue – what negative impacts does it have on your business?
- What is currently blocking you from solving this problem?
- Why do you think this is happening?
- Why does solving this matter to you now?
Keep probing until you get to the root causes driving their interest in your solution. The more details you gather, the better you can position your product as the ideal remedy.
3. Impact Questions
Understanding the impacts of their problem paints a vivid picture of what life could be like with your solution in place.
Drive that contrast home by asking questions like:
- How does this problem impact your team’s productivity?
- How does this issue affect your customers?
- What costs or wasted time does it incur?
- How does this hinder your ability to hit targets or scale?
Quantifying the negative effects makes the buyer more eager for change. They can clearly envision the positives your product will bring.
4. Vision Questions
Now flip the script by asking what an ideal future looks like. How would their world improve if the problem was solved?
- In a perfect world, what would you want to see happen regarding [problem]?
- How do you envision your team functioning if this issue went away?
- What objectives could you accomplish if you had [product’s capabilities]?
- What new opportunities could you capitalize on?
Painting this positive vision solidifies why it’s worth it for them to invest in your solution.
5. Evaluation Questions
Finally, you want to assess which solutions they’ve already tried and how well those attempts worked.
This helps overcome any hesitations they have about making a change:
- What approaches have you tried to solve this issue so far?
- What limitations did you run into with that solution?
- What results were you hoping to achieve that didn’t happen?
- If you could wave a magic wand, what capabilities and benefits would your ideal solution have?
You can then directly address those unmet needs and desires with your offering.
Best Practices for Questioning
Keep these tips in mind as you craft your questioning strategy:
Ask Open-Ended Questions
Steer clear of closed questions that can be answered with a quick “yes” or “no.” For example, “Are you looking to increase sales this quarter?” is less likely to elicit details than, “What sales targets are you focused on hitting this quarter?”
Ask One Question at a Time
Don’t overwhelm them with compound questions. Keep it simple so they can give thoughtful answers.
Use Follow-Up Questions
Ask, “What makes you say that?” or, “Could you expand on that?” to extract more details after their initial response.
Go Broad to Specific
Start with big-picture questions and gradually drill down into specifics. This creates a natural flow to the conversation.
Listen 80% of the Time
Focus on truly listening versus just waiting your turn to talk. This builds rapport and gives you insights for crafting relevant follow-up questions.
Take Notes
Jot down keywords and themes from their responses you can reference later and expand upon.
Sequencing Your Questions
The flow of your questions is just as crucial as the questions themselves. Here are some best practices for sequencing a productive conversation:
Start with rapport building. Ask an icebreaker question about them, their role, or their company before diving into business. This establishes comfort and trust.
Begin broad. Ask about their overall organization, goals, and challenges. Gradually drill down into specifics.
Funnel through qualifying questions first. This ensures they’re a fit before spending more time.
Uncover their “why.” Explore what’s driving their interest before pitching solutions.
Speak to their pain points. Confirm you understand where they’re coming from.
Transition to future vision. Shift the tone from negatives to the positive possibilities your solution provides.
Rephrase and summarize. Repeat what you’ve learned to confirm you understand and keep the dialogue focused.
Wrap up by previewing the next steps. Gain agreement on appropriate follow-up actions.
Questioning Dos and Don’ts
Here are a few final dos and don’ts to keep in mind:
DO:
- Keep questions conversational and casual in tone
- Show curiosity by asking, “How so?” or “In what way?”
- Allow silence after questions to give them space to think
DON’T:
- Ask confrontational questions that put them on the defense
- Interrupt or cut them off while speaking
- Only pay attention to answers that support your goals
DO:
- Admit when you don’t know something
- Ask for clarification if you’re unsure of the meaning
DON’T:
- Fake knowledge of unfamiliar topics
- Make assumptions or jump to conclusions
DO:
- Provide transitions between questions
- Summarize periodically to keep on track
DON’T:
- Rapid-fire questions without context
- Let the conversation drift off course
Transform Your Sales Conversations
Asking insightful, strategic questions is a game changer when it comes to closing more sales. Instead of scripted pitches, have genuine conversations focused on the buyer. Keep these question types, sequencing techniques, and best practices in mind as you craft your discovery strategy.
When you focus on their needs first, prospects feel understood. They see you’re there to add value, not just make a quota. Thoughtful questioning builds the trust and rapport you need to turn prospects into long-term customers.
