EMWNews Academy

Asking Better Questions in Messenger

Learn how to ask thoughtful, open-ended questions in Facebook Messenger that build trust, deepen conversations, uncover business needs, and strengthen long-term relationships.

📅 Last Updated: July 2026

Table of Contents

The quality of your questions often determines the quality of the conversation.

People enjoy talking with those who genuinely want to understand them. A thoughtful question creates space for sharing. A careless question closes that space. The questions you ask in Messenger determine whether conversations deepen or fade.

This lesson teaches you how to ask better questions in Messenger. You will learn to ask questions that build trust, encourage sharing, and reveal what matters most to business owners. Professional Partners ask questions to understand—not to steer conversations toward a sale.

Great conversations are driven by great questions. Professional Partners are remembered not because they have all the answers. They are remembered because they ask thoughtful questions, listen carefully, and genuinely care about understanding the businesses they serve.

Why Questions Matter

Questions are the foundation of meaningful conversation. Here is why they matter:

Questions Show Interest

When you ask a thoughtful question, you demonstrate that you care about the other person. You are saying, "I want to understand you." This builds connection.

Questions Build Trust

Asking questions before offering advice builds trust. You show that you respect their knowledge and experience. Trust grows when people feel understood.

Questions Encourage Sharing

Good questions invite people to share. They create space for dialogue. Conversations that flow from questions are more natural and more meaningful.

Questions Deepen Relationships

Thoughtful questions lead to deeper understanding. Deeper understanding builds stronger relationships. Questions are the tool that deepens connections over time.

Questions are not just tools. They are the language of respect.

Open vs. Closed Questions

Understanding the difference between open and closed questions is essential for better conversations.

Closed Questions

Closed questions can be answered with yes, no, or a single word. They limit conversation. They are useful for gathering specific information, but they do not invite meaningful dialogue.

Examples: "Do you like your customers?" "Is business good?" "Do you use Facebook?"

Why they are limited: They do not invite sharing. They end the conversation rather than extending it.

Open Questions

Open questions invite people to share their thoughts, feelings, and experiences. They begin with "what," "how," "why," "tell me about," or "describe." They create space for real conversation.

Examples: "What do you appreciate most about your customers?" "How has business been this year?" "What role does Messenger play in your communication with customers?"

Why they work: They invite people to share. They show genuine interest. They create deeper conversations.

Open questions are the foundation of meaningful conversation in Messenger.

Questions That Build Trust

Certain questions naturally build trust. Here are categories and examples:

Business Journey Questions

  • "What inspired you to start your business?"
  • "How did you get into this industry?"
  • "What has been the most rewarding part of your journey?"
  • "What was the biggest challenge you faced early on?"
  • "What keeps you motivated?"

Customer Questions

  • "What do your customers appreciate most about your business?"
  • "How do you help customers understand what makes you different?"
  • "What feedback do you hear most often from your customers?"
  • "What do you wish more customers knew about your business?"
  • "How do you build relationships with your customers?"

Goal Questions

  • "What are you most excited about for your business right now?"
  • "What would you like to achieve in the next few years?"
  • "What does success look like for you?"
  • "What would you want your business to be known for?"
  • "What is the most important goal you are working toward?"

Challenge Questions

  • "What is the biggest challenge you face right now?"
  • "What keeps you up at night about your business?"
  • "What would make your work easier?"
  • "What do you wish you had more time for?"
  • "What is the hardest part of what you do?"

Community Questions

  • "What do you love most about serving this community?"
  • "How has the community supported your business?"
  • "What changes have you seen in the community over the years?"
  • "What makes your community special for your business?"
  • "How do you give back to the community?"

Future Vision Questions

  • "What is your long-term vision for your business?"
  • "Where do you see your business in five years?"
  • "What impact do you hope your business will have?"
  • "What legacy do you want to leave through your business?"
  • "What inspires you to keep building?"

Questions that build trust are those that show genuine interest and create space for sharing.

Questions to Avoid

Some questions damage trust. Avoid these entirely in Messenger:

Leading Questions

Example: "Don't you think your business could benefit from more visibility?"

Why to avoid: Leading questions push a specific answer. They feel manipulative. They signal an agenda.

Interrogation-Style Questioning

Example: Asking five questions in a single message.

Why to avoid: Overwhelming. Feels like an interview. Does not invite conversation.

Highly Personal Questions

Example: "Why did you choose this career?" "Do you have a family?"

Why to avoid: Too personal for early conversations. Invades privacy. Damages trust.

Questions That Sound Like Sales Qualification

Example: "What is your marketing budget?" "How many employees do you have?"

Why to avoid: Sales qualification questions are transparent. They reveal your agenda. They damage trust.

Good questions invite conversation. Bad questions end it.

Messenger Tip

Ask one question at a time.

One thoughtful question allows the business owner to respond fully. Multiple questions at once are overwhelming and often result in partial answers. Ask one question, listen to the response, then ask the next.

This approach shows respect and keeps the conversation focused and comfortable.

Professional Insight

Listening begins with asking better questions.

The quality of your questions determines the quality of what you learn. When you ask thoughtful, open-ended questions, you invite meaningful responses. When you ask closed or leading questions, you limit what you learn.

Professional Partners ask better questions because they genuinely want to understand. Their questions reflect curiosity, respect, and a desire to serve.

Real World Example

Let us see how thoughtful questions build trust and reveal valuable insights in Messenger conversations.

Example 1: Family-Owned Restaurant

You: "I enjoyed learning about your restaurant and the generations of families you serve. What do you think has been the key to building that kind of connection with your customers?"

Owner: "I think it's consistency and genuine care. We treat everyone like family. We remember their names, their orders, their kids' names. It sounds simple, but it matters."

You: "That consistency and care clearly shows. It's rare to find that kind of personal connection. What do you think makes your restaurant special to the community?"

Owner: "We've always believed food brings people together. But it's really about the relationships. People come here not just for the food, but because they feel welcomed, remembered, and valued."

You: "That is beautiful. Thank you for sharing that. What are you most excited about for your restaurant this year?"

Owner: "We are planning to do more community events. We love bringing people together."

What Happened

  • Trust grew: Each question deepened the conversation
  • Understanding deepened: We learned about their values, their connection to the community, and their plans
  • No selling occurred: The conversation was genuine and respectful
  • A relationship was built: The door is open for future conversations

Example 2: Landscaping Company

You: "I came across your business and was impressed by your before-and-after photos. Your work really transforms properties. What has been your favorite project to work on in our area?"

Owner: "Thank you! We recently did a complete redesign for a family home that had been neglected for years. Seeing their reaction made it all worthwhile."

You: "That sounds incredibly rewarding. What do you think makes your approach different from other landscaping companies?"

Owner: "We focus on listening to what the client actually wants. We don't just show up and start working. We take time to understand their vision."

You: "Listening to the client's vision is a great approach. What do you enjoy most about working on residential projects?"

What Happened

  • Trust grew: Questions focused on their work and values
  • Understanding deepened: We learned about their approach and what they value
  • No selling occurred: The conversation was about their business
  • A relationship was built: Trust is growing

Great questions create great conversations.

Common Mistakes

Avoid these common errors when asking questions in Messenger:

  • Asking too many questions: One or two thoughtful questions are enough. More is overwhelming.
  • Asking closed questions: Yes/no questions do not invite conversation.
  • Asking leading questions: Pushing a specific answer signals an agenda.
  • Asking sales qualification questions: "What is your budget?" damages trust.
  • Asking personal questions: Invading privacy damages trust.
  • Asking negative questions: "What is wrong with your business?" creates defensiveness.
  • Not listening to the answer: If you do not respond to what they shared, they will notice.
  • Asking generic questions: Generic questions show no real interest.
  • Asking without context: Questions should flow naturally from the conversation.
  • Forgetting to acknowledge: Always acknowledge their answer before asking another question.

Messenger Field Assignment

This assignment helps you build a library of thoughtful questions.

  1. Write ten open-ended questions you could ask businesses in different industries.
  2. For each question, consider:
    • Is it open-ended?
    • Does it invite sharing?
    • Does it build trust?
    • Would I want to answer this question?
  3. Review and improve each question. Make it more thoughtful and open.
  4. Do NOT send them. This is practice.

This assignment helps you develop the skill of asking better questions.

Academy Field Notes

Record your questions and the responses they generate in your field notes. These notes help you refine your questioning skills.

Record for each conversation:

  • Business: Name and industry
  • Question asked: What you asked
  • Response: How they answered
  • Insights learned: What you discovered
  • Possible follow-up: What to ask next

Your field notes are a record of your growing ability to ask better questions.

Continue Your Academy Journey

Before moving to the next lesson, consider reviewing these foundational concepts:

When you're ready, continue to the next lesson:

Active Listening in Digital Conversations

Key Takeaways

  • The quality of your questions often determines the quality of the conversation.
  • Questions show interest, build trust, encourage sharing, and deepen relationships.
  • Open questions invite conversation. Closed questions limit it.
  • Questions that build trust ask about business journey, customers, goals, challenges, community, and future vision.
  • Avoid leading questions, interrogation, personal questions, and sales qualification questions.
  • Ask one question at a time. One thoughtful question is more effective than several at once.
  • Listening begins with asking better questions.
  • Avoid common mistakes: asking too many questions, closed questions, and not listening.
  • Practice asking better questions. Your skill improves with practice.
  • Professional Partners are remembered because they ask thoughtful questions, listen carefully, and genuinely care about understanding the businesses they serve.

Frequently Asked Questions

How many questions should I ask at a time?

One or two thoughtful questions per message. More than that becomes overwhelming. Ask one question, let them answer, then ask the next.

What if a business owner does not answer my question?

Respect their response. They may not want to share that information. Move on to another topic. Do not push.

Should I ask the same questions to every business?

No. Every business is unique. Adapt your questions to what you have observed and what you want to understand.

What if I ask a question and the answer is vague?

Follow up gently. "That's interesting. Could you tell me a little more about that?" This shows continued interest.

Can I ask questions about their marketing?

Yes, but carefully. "How do you stay visible to customers?" is better than "What marketing channels do you use?" Keep it natural.

What if a business owner asks me a question?

Answer honestly and simply. Then return to their story. "That's a good question. I'm curious to hear more about your approach."

Should I write down good questions I hear from others?

Yes. Building a library of questions is valuable. Observe how others ask questions and adapt what works.

What is the best type of question to ask?

Questions that begin with "what" or "how" are usually most effective. They invite people to share their experience.

What if I run out of questions?

That is a sign that you need to listen more carefully. There is always more to learn. Listen for what they share and follow up.

What is the next lesson?

The next lesson is Active Listening in Digital Conversations. It teaches you how to listen actively in Messenger conversations.

Great Questions Create Great Conversations

Professional Partners are remembered not because they have all the answers. They are remembered because they ask thoughtful questions, listen carefully, and genuinely care about understanding the businesses they serve.

You have learned why questions matter, how to ask open-ended questions, what topics build trust, and what questions to avoid. You have practiced asking better questions. You are ready.

Your next step is to learn how to listen actively:

Continue with Active Listening in Digital Conversations.

Reviewed By Our Editorial Team

Jordan Taylor - Senior Editor at EMWNews

Jordan Taylor

Senior Editor, EMWNews

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