Want Stronger Relationships? Ask Better Questions

Key to Building Meaningful Relationships: Ask Great Questions

Great relationships—whether personal or professional—begin with great conversations. Great conversations, in turn, are often a byproduct of great questions. The ability to ask thoughtful, intentional, and meaningful questions is more than an important skill; it’s a superpower. It allows you to move beyond superficial conversations and into meaningful exchanges that build and nurture trust, foster more profound understanding, and open doors to new opportunities. Asking better questions isn’t about interrogation or filling silences; it’s about creating meaningful dialogue that adds value to the lives of those you engage with.

Mastering the art of asking great questions transforms your relationships and sets the stage for unparalleled personal and professional growth.

Why Asking Great Questions Matters More Than Ever

Asking great questions is one of the simplest yet most impactful ways to demonstrate genuine care, amplified curiosity, and professional respect for others. It signals that you value the person standing or online right before you, whether a friend, a colleague, or a client. At its essence, a well-crafted question serves as a bridge—it creates an opportunity for connection, encourages open communication, and helps uncover more profound insights that might otherwise remain hidden.

In a professional context, great questions can unlock better collaboration and authentic trust. Imagine a client meeting where, instead of jumping into the solutions you can provide, you ask, “What’s one strategic priority you are struggling with the most at the moment, and how can we brainstorm it together?” That question shows an interest in their most pressing need and a desire to help them think through it thoughtfully. Similarly, the right question can help you understand someone much deeper in personal settings. Asking, “What motivates you to keep pursuing your goals, even on the tough days?” invites vulnerability and reflection in ways typical small talk cannot. Who cares about the weather (I have an app for that!) or the garbage on much of our TV?

This practice isn’t just about the words themselves; it’s about what they enable. Great questions open doors to ideas, solutions, and emotions that would remain unexplored. And great questions matter more than ever when creating authentic and mutually value-based questions.

Get Beyond Just Good to Great Questions

While good questions keep the conversation moving forward, great questions create meaningful connections – they often excite or disturb others to shift the focus from mere information exchange to exploration, insight, and growth.

Great questions are open-ended, relevant, and thought-provoking. They encourage people to pause, reflect, and share their thoughts or feelings. They are contextual—tailored to the moment and the person you’re engaging—and show that you’re actively involved in the conversation. For example, in a one-on-one meeting, asking, “What concerns you most about the direction of this project?” is far more impactful than simply asking, “Is the project on track?”

On the flip side, poorly framed questions can derail conversations. Leading questions often feel manipulative, while overly simplistic yes-or-no questions shut down dialogue rather than inviting it. For instance, asking, “Did you like this strategy?” limits the discussion. Instead, you could ask, “What aspects of this strategy didn’t work for you, and where do you see room for dramatically enhancing it?” This subtle shift creates a space for feedforward, deeper exploration, and collaboration to make the end result stronger.

Mastering the difference between good and great questions begins with the intention behind your inquiry. Are you genuinely seeking to learn or simply filling the silence? Your intent shapes the impact.

Great Questions Begin With You Listening Louder!

The art of asking great questions combines curiosity, empathy, and active listening. It’s not about coming to the conversation with a pre-determined list of queries; it’s about tuning into what’s being said—and what isn’t—and responding with genuine curiosity.

One of the foundational elements of asking great questions is listening louder! This means entirely focusing on the other person, understanding their perspective, and responding thoughtfully. When you listen intently, your follow-up questions feel natural and personal, allowing the conversation to flow. For instance, if someone shares a recent challenge, instead of moving on, ask, “What was the biggest lesson you took away from that experience?” or “Why is that so important to you?”

Context is equally critical. Getting beyond the generic, scripted, and candidly dull questions and tailoring your questions to the specific situation and the needs of the individual demonstrates amplified care and a higher level of respect. In a professional setting, this might look like asking, “What does success look like for you in this role, and how can I help you get there?” In a personal context, it might be as simple as, “What’s a recent win you’re most proud of?” During year-end reviews, one of my favorite questions is, “What relationships did you neglect this past year?”

Finally, balance your inquiry with empathy. Asking questions that show emotional intelligence and courage—like acknowledging someone’s feelings or experiences—strengthens your connections. For example, instead of asking, “How’s the workload on your team?” you might ask, “I’ve noticed your team has had a heavy workload recently—how are you managing that, and what one thing can I do to help you or your team not get overwhelmed?” This approach opens the door for honest feedback and builds trust.

Building Great Relationships Through Great Questions

The best questions are those that foster relationships by creating space for openness, trust, and meaningful connection. In business relationships, this might involve asking questions that help you truly get to know someone, like, “What’s a personal value that drives the decisions you make?” These inquiries show that you’re interested in who they are, not just what they do. After all, you’re asking others to trust you daily. What are you doing to get to know them? Or give them a chance to get to know the real you?

Great questions can break down barriers and accelerate rapport. For example, asking a colleague, “What inspires you most about your role?” or a client, “What are your long-term goals in this effort, and how can we help you derisk the journey?” demonstrates that you’re invested in their success. Leveraging tools like Avnir’s Relationship Bank™ can further elevate your approach. By uncovering meaningful details about your network, you can craft personalized, relevant questions that resonate with your audience.

The more intentional you are about your questions, the more opportunities you create for authentic relationships.

Practical Tips and Resources for Mastering Great Questions

Like any skill, mastery of asking great questions requires patience, practice, persistence, and pivots (based on reflections). Start by incorporating these strategies into your daily interactions:

• Be patient with yourself. Great questions demand a strong command of the English language, active listening, and control to stop offering solutions and conveying your credibility through the questions you ask. Be patient.

• Practice listening louder. Before responding, paraphrase what you’ve heard to ensure you understand and demonstrate that you’re paying attention. Pay particular attention to what is NOT said.

• Be persistent, but don’t outwear your welcome. Be genuinely curious about why something happens, not just observe what’s happening. This will allow you to ask great follow-on questions and dig deeper. Be cautious not to make others uncomfortable to the point of “Enough!”

• Start with “how” and “why.” These words naturally open conversations and encourage deeper exploration.

• Pause after asking. Give others the time to think and respond fully rather than rushing to fill silences.

• Pivot with each learning moment. Great questions can be fantastic learning and growth opportunities. Learn to pivot the types of questions you ask, your style in how you ask them, and timing on when they’re most appropriate.

To take your skills further, leverage tools and resources designed for relationship-building. Avnir’s Relationship Bank™ provides insights into your network, helping you ask more personalized and thoughtful questions. Books like A More Beautiful Question by Warren Berger, and Power Questions by Andrew Sobel offer practical advice and inspiration to enhance your questioning techniques.

The Power of Great Questions

Great questions are more than conversation starters—they’re fantastic relationship builders. They create a space for trust, understanding, and collaboration. Whether you’re asking a client about their vision, a friend about their dreams, or a colleague about their challenges and opportunities, the right question can transform your relationship.

So, what’s the next great question you’ll ask? Make every conversation an opportunity to connect more deeply. And when you’re ready to take your professional relationships to the next level, let Avnir empower you with the tools and insights to make every interaction count.

Visit Avnir today and start building connections that matter.