Benefits of Using Open-Ended Questions

7 Words That Changed How I Lead Forever It started in a conversation I almost rushed through. A team member had shared an idea I wasn’t fully sold on. I nodded, ready to move on—but something stopped me. Instead, I asked: “And what else?” What happened next surprised me. They paused, thought, then added something deeper, something better. That second idea was the one we moved forward with. And it worked. If you’re a coach, manager, or team leader, this one simple question could be the most powerful tool you’re not using. Why it works: • It communicates trust. • It invites deeper thinking. • It keeps you from making premature judgments. What the research says: Studies in executive coaching show that open-ended follow-ups like “And what else?” increase solution-based thinking by up to 42%. That’s not fluff, that’s strategy. Here’s how to use it this week: • In your next 1:1, let silence linger. • When your team member shares an idea, respond with: “That’s interesting, and what else?” • Repeat it once or twice. You’ll be amazed at what surfaces. And if you lead a team or coach others, make this part of your regular rhythm. 📌 Bookmark this if you ever struggle with shallow conversations or stalled ideas. Because real leadership doesn’t rush, it listens better. ♻️ I hope you found this valuable, please share with your network. 📌 Click "Follow" and 🔔 #LeadershipDevelopment #CoachingSkills #AskBetterQuestions

Some of my favorite customer moments come from a simple shift: asking open-ended questions and letting the conversation breathe. I do come to meetings with a checklist and goals to “accomplish” during the discussion. But over time, I realized I was missing something important: the customer’s story, in their own words. Closed-ended questions brought a lot of polite “yes” answers and head nods, but rarely led to a breakthrough. Sebastien Waltzing left a comment on one of my recent posts and got me thinking about the real magic that happens when we invite customers to share their view of value. Questions that cannot be answered in a single word often trigger a pause, and then a deeper look at what matters most on their side of the table. Here’s what I try now: Instead of, “Are you satisfied with the feature?” I’ll ask, “How does this feature change the way your team hits its goals?” Or, “What results would make this an absolute win in your book?” Conversations like these do more than just fill out a quarterly or strategic review. They turn customers into collaborators. We hear about unexpected wins, real struggles, and big ambitions. We learn where to invest next. So, my challenge to every customer success leader: pause your agenda, and let the customer lead for a moment. You will not just confirm value. You will co-create it. What is one open question you have seen spark a real, eye-opening answer from your customers? I am always looking to add new ones to my toolkit.

There is only one behavior at work that you can truly fake, until you become it… People can sense insincerity from a mile away. Even if you manage to fool them once, you’ll eventually show your true self. Here are some things you cannot easily fake: - Patience - Presence - Expertise - Excitement - Empathetic - Confidence - Compassion The real you almost always shows up in an emotionally charged conversation where you’re - Angry - Afraid - Anxious - Impatient - Resentful But there's one behavior you can get away with faking: Curiosity Once you ask a great question in a non-judgmental tone, their brain switches attention from you to them. 
They begin scanning the brain to make connections and ultimately, find an answer. They’re often surprised by what comes out their mouth. But when you ask a direct or closed-ended question like “Did you try x?” the brain stays dark. 

 - No Insights - No Surprises - No Breaking Through Bias - No Deepened Connections - No Change in Your Reputation But if you ask an open-question in a curious tone (even if you lack curiosity) A question like... - What’s most important to you about that? - What does ‘good’ look like to you? - What have you tried? Or follow-up questions like: - How can you tell? - What else? You can even make a statement that acts like an open question: - Say more about that… - Tell me more… - Go on… When you ask a great question in a curious tone (whether you actually feel curious or not ) the listener has epiphanies . You don’t need an fMRI machine to prove it. Just watch someone’s reaction the next time you ask a great question. They find information that they never would’ve found if you'd asked: - Do you have time to ___? - Do you want to___? - Do you think__? - Did you try __? We live in a fast-paced culture... We rarely pause to ask an open question... We often make our assumptions true, whether we know it or not... That’s why #RadicalCuriosity is rare. Once you start, your reputation gets an upgrade because: - People like being around people who ask questions that make them feel safe. - People like being around people who can help them solve problems. - People are more happy & productive when they feel safe. This is the fastest way to upgrade your reputation because.... Executives (including the B.o.D) DO NOT want you to come with all the answers. - They don’t want a presentation... - They want a conversation that helps them make sound decisions. When you do this, you stand out in the best way. They'll ask you back. But this time, you won’t work all weekend trying to have all the facts. You’ll prepare using a principle I call #MinimumEffectiveDoing, and show up with gravitas and a smile, as you help them find solutions. You'll take your reputation from Worker-Bee to Queen Bee in one conversation. What questions will you ask in your conversations at work and home?

⁉ Open-Ended Questions are your Super Power! Use them to build rapport, gather information, build your credibility and overall connection, in every conversation. Here are four main types of open ended questions: ❓ Clarifying Questions: Questions that share deeper insights and help the speaker in summarizing their thoughts. For example, if I was talking to an HR professional about company values, I would ask: “Tell me more about this new core value”, or “Where do you see it come to life in your organization?” or “How would you describe it to a new hire?” ❓ Connecting Questions: Questions that require some context and help you understand the bigger picture. In the same HR meeting I might ask: “Help me understand how this core value links with the overall mission of the company.” ❓ Focus Questions: Questions that dig into concepts and clarify expectations. For instance, if I was discussing a presentation a team asked me to make, I could ask:  “If the keynote I delivered was a smashing success, what would be three learning objectives we would have covered?” ❓ Big Picture Questions: Questions that provide broad perspectives and historical context. They help you understand the general philosophy behind decisions. In the same discussion about the keynote, I might ask: “Tell me more of how you decided on this theme? What other themes have worked in the past?” Be strategic and think ahead of your conversation so you can ask solid open ended questions. Are there any questions make the difference for you? #askingquestions #openendedquestions #highimpactlistening #listening #alwaysbelearning

Ask a question. A real one. Beyond “how are you” and “what do you do” … ask someone how they got to where they are. Why this moment matters to them. Ask them to tell you a story. To detail their pathway from there to here. Charles Duhigg hits it spot on in this CNBC interview when he says that questions are a differentiator between #SuperCommunicators and the everyday conversationalist. Questions = the bridge / open door between you and another person. That’s not to say you should show up to your next conference and exclusively ask questions. But it does mean embodying CURIOSITY in your approach. Meeting someone for the first time? Ask them about how they got to this place in their career. Pitching a potential customer? Ask them what MATTERS most to them today and why. Receiving feedback in your 1:1? Ask your boss to share an example of what success looks like to them. Keep in mind that the foundational goal of any communication is deeper connection. Action, answers, and any other outcomes layer atop relationship and trust. By staying curious and asking open ended (what Duhigg calls 'deep') questions, you invite the conversation to go farther, the connection to get stronger, and the opportunity for mutual buy-in to strengthen. What I particularly like about Duhigg’s approach is that he’s come to communication from a journalist background. Which means his book, Supercommunicators, takes a gentle approach to bringing the reader into the story — and into practical best practices. If you’re new to working on your communications skills, this is a great place to start. I'll link his book in the comments.

I believe that asking good questions is the most powerful tool in a lawyer's business development toolkit. And the most effective type of question is an open-ended one. The beauty of open-ended questions is that they unlock doors to deeper understanding. Unlike close-ended questions that often elicit mere facts, open-ended inquiries invite clients to share their challenges, aspirations, and concerns. By posing questions such as "What challenges are you currently facing?" or "What is your primary objective in this case?", you can unearth different layers of a prospective client's situation, allowing you to engage in meaningful dialogue. However, as this dialogue unfolds, it's essential not to remain a passive listener. Weaving in insights that reflect your expertise demonstrates curiosity, interest and creates a space where clients feel both heard and enlightened. Saying something along the lines of “That makes sense. I’ve dealt with clients in similar situations and here’s how we approached that problem…” can go a long way toward building confidence that you’re the right lawyer for the job. In my experience, too many lawyers spend an inordinate amount of time preparing answers to questions they expect to be asked during a business development conversation. A better use of time is to come armed with lots of thought-provoking, open-ended questions of your own.

I wasted years thinking small talk about weather made me good at sales. My process was embarrassingly simple: Pull up their LinkedIn, scan their last email, then wing it with some chitchat about their location or the weather. I assumed "natural rapport" meant improvising my way through calls. And I was wrong. Truth is, I was resisting structure. I believed scripting meant being robotic and proper preparation would kill authentic conversation. So I kept it casual, kept it flowing, and… kept missing opportunities. Then I started working with a sales coach. Every Wednesday at 10am, I'd get on a call to hear exactly why my approach was wrong. It was expensive, uncomfortable, and exactly what I needed. One day, he caught me using my favorite line (among others) while I talked through a sales call: "Any thoughts on that?" His feedback was brutal: "You're swinging between closed-ended questions that shut people down and questions that leave them hanging. What if, instead, you guided the conversation?" Ouch. Mind blown. He was right. In trying to keep things casual and unstructured, I'd been failing to guide meaningful conversations. My resistance to "scripted" questions wasn't just making my calls superficial—it was leaving both me and my prospects without direction. So we changed… direction: Create and rehearse a flow and replace every closed question with an open one. Instead of "Should I walk you through our services?"   → "What’s the goal?" then… “What’s behind that?” Instead of "Any thoughts?"   → "How would this fit into your current process?" Instead of "Does that pricing work for you?"   → "How does this compare to what you were thinking?" The difference was immediate. Prospects started sharing their actual concerns. Their real budgets. Their true decision-making process. All the things they used to hold back when I gave them an easy "no thoughts" escape hatch. Last quarter alone, we added a record in new MRR—twice our typical close rate. Sales cycles that used to drag on for 8 months now wrap up in 4. But the biggest change is that I finally see sales calls for what they *should* be: guided conversations with clear direction and open ended questions, *not* let-me-wing-this-trust-me-I-got-this improv sessions. The beauty of this approach is that it's not in any way manipulative or calculating. When you introduce structure and direction, you're also helping prospects quickly decide if what you have to offer is what they actually need. Everyone wins. P.S.   Try this today: Take your most common closed question and flip it into an open one, directing one. You'll be amazed at what people tell you when you stop giving them permission to say nothing.

Weak questions bore brains. Let’s crank the voltage. Afraid to dig deep? Let sharper queries unravel. By the end of this post, you’ll have a toolkit to ask questions that spark curiosity, reveal hidden opportunities, and guide conversations like a master negotiator. After years in negotiation, I’ve learned that asking the right questions isn’t just an art—they’re a game-changer. Here are 5 types of questions to elevate any conversation: 𝟭. 𝗘𝘅𝗽𝗹𝗼𝗿𝗮𝘁𝗼𝗿𝘆 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Dig deep. Understand the big picture. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Use open-ended “what,” “how,” or “why” questions to encourage free sharing. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘧𝘢𝘤𝘵𝘰𝘳𝘴 𝘢𝘳𝘦 𝘮𝘰𝘴𝘵 𝘪𝘮𝘱𝘰𝘳𝘵𝘢𝘯𝘵 𝘵𝘰 𝘺𝘰𝘶𝘳 𝘵𝘦𝘢𝘮 𝘸𝘩𝘦𝘯 𝘤𝘰𝘯𝘴𝘪𝘥𝘦𝘳𝘪𝘯𝘨 𝘢 𝘱𝘢𝘳𝘵𝘯𝘦𝘳𝘴𝘩𝘪𝘱?” 𝟮. 𝗖𝗶𝗿𝗰𝘂𝗹𝗮𝗿 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Reveal patterns and relationships. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Ask how people, ideas, or events influence each other. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘏𝘰𝘸 𝘥𝘰 𝘺𝘰𝘶 𝘵𝘩𝘪𝘯𝘬 𝘺𝘰𝘶𝘳 𝘴𝘪𝘴𝘵𝘦𝘳 𝘷𝘪𝘦𝘸𝘴 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯-𝘮𝘢𝘬𝘪𝘯𝘨 𝘪𝘯 𝘵𝘩𝘦 𝘤𝘰𝘮𝘱𝘢𝘯𝘺?” 𝟯. 𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝘃𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Inspire self-awareness and critical thinking. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Gently challenge assumptions and help connect actions to outcomes. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘸𝘰𝘳𝘬𝘦𝘥 𝘸𝘦𝘭𝘭 𝘪𝘯 𝘵𝘩𝘢𝘵 𝘱𝘳𝘰𝘫𝘦𝘤𝘵, 𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘺𝘰𝘶 𝘤𝘩𝘢𝘯𝘨𝘦?” 𝟰. 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗶𝘃𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Unlock creativity and spark innovation. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Ask forward-looking or “what if” questions to inspire out-of-the-box thinking. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘞𝘩𝘢𝘵 𝘪𝘧 𝘸𝘦 𝘳𝘦𝘪𝘯𝘷𝘦𝘯𝘵𝘦𝘥 𝘰𝘶𝘳 𝘱𝘳𝘰𝘤𝘦𝘴𝘴 𝘦𝘯𝘵𝘪𝘳𝘦𝘭𝘺 𝘵𝘰 𝘵𝘢𝘤𝘬𝘭𝘦 𝘵𝘩𝘪𝘴 𝘤𝘩𝘢𝘭𝘭𝘦𝘯𝘨𝘦?” 𝟱. 𝗦𝘁𝗿𝗮𝘁𝗲𝗴𝗶𝗰 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 📌 𝗣𝘂𝗿𝗽𝗼𝘀𝗲: Align actions with long-term goals. 🛠️ 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵: Focus on weighing options and balancing risks and rewards. 💡 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: “𝘏𝘰𝘸 𝘥𝘰𝘦𝘴 𝘵𝘩𝘪𝘴 𝘢𝘭𝘪𝘨𝘯 𝘸𝘪𝘵𝘩 𝘰𝘶𝘳 𝘭𝘰𝘯𝘨-𝘵𝘦𝘳𝘮 𝘨𝘰𝘢𝘭𝘴, 𝘢𝘯𝘥 𝘸𝘩𝘢𝘵 𝘳𝘪𝘴𝘬𝘴 𝘴𝘩𝘰𝘶𝘭𝘥 𝘸𝘦 𝘱𝘳𝘦𝘱𝘢𝘳𝘦 𝘧𝘰𝘳?” Great questions aren’t random—they’re your most powerful tools for influence, innovation, and clarity. Master them, and you’ll master the room. What’s one question you’ve asked that completely changed a conversation? Drop it below—I’d love to learn from you. (𝘗.𝘚. 𝘐’𝘷𝘦 𝘢𝘴𝘬𝘦𝘥 𝘮𝘺 𝘧𝘢𝘪𝘳 𝘴𝘩𝘢𝘳𝘦 𝘰𝘧 𝘢𝘸𝘬𝘸𝘢𝘳𝘥 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯𝘴 𝘵𝘰𝘰. 𝘉𝘶𝘵 𝘩𝘦𝘺, 𝘵𝘩𝘢𝘵’𝘴 𝘩𝘰𝘸 𝘺𝘰𝘶 𝘨𝘦𝘵 𝘣𝘦𝘵𝘵𝘦𝘳!)

Have you ever noticed how asking "Why did you do that?" can make others feel judged or defensive? It's a common issue in both personal and professional settings. Instead, try asking "What" and "How" questions to foster a more open and constructive dialogue. Instead of "Why did you miss the deadline?" Ask: "What challenges did you encounter?" or "How can we adjust the plan to meet deadlines in the future?" Instead of "Why are you doing it this way?" Ask: "What led you to this approach?" or "How do you think this method will benefit the project?" By focusing on "What" and "How," you encourage problem-solving and learning, creating a more supportive and effective environment.

What you learn depends on what you are willing to learn. When in a discussion, negotiation, or team project, the way you ask a question shapes the answers you receive. Your framing doesn’t just influence the response—it determines what possibilities open up (or shut down). Consider these two scenarios: (1) Team decision-making: Asking "Who is responsible if this fails?" creates defensiveness. Asking "What can we do to set ourselves up for success?" shifts the focus to proactive problem-solving. (2) Negotiation: Asking "Can you lower the price?" leads to a yes/no answer. Asking "What flexibility do we have on pricing and value?" invites creative solutions—maybe a better package, a longer-term deal, or additional perks. Here are three simple shifts to unlock better insights: (1) Ask open-ended questions. Instead of "Is this possible?" try "How might we make this work?" (2) Frame questions toward learning, not blame. Instead of "Why did this go wrong?" ask "What can we learn from this?" (3) Expand the lens. Instead of "Should we do A or B?" ask "What other options haven’t we considered?" Curiosity isn’t just about what you ask—it’s about how you ask it. #Curiosity #Learning #Leadership #Asking #Growth #Reflection