Best Practices for Asking Questions

Management isn't about having all the answers. It's often about using a perfectly timed question. Here are 7 questions for the hardest management moments (and tactics you can apply to any situation)... Why are questions superior to directives? - Engage: Your team wants to help & to be heard. - Empower: You're role-modeling vulnerability & respect. - Enlighten: You'll generate more data for better decisions. You'll notice I use a similar pattern: Label + Question - Label: It's a negotiation tactic. If you say "It seems like you're upset" they pause to question if that's true, diffusing the emotion. - Question: I make them open-ended. I want to get them talking and surface data, ideally their underlying 'Why.' ⬇️⬇️⬇️ 1. Moment: Your star employee just told you about a competing offer. Question: Jen, I appreciate that you feel comfortable discussing this with me. What role would you like me to play in reviewing this possibility with you? 2. Moment: You just gave critical feedback, and they’ve clearly shut down. Question: Bill, I sense I’ve upset you. What piece of feedback was most off of the mark? 3. Moment: You’ve found a great candidate you want to hire, and they’re about to leave for the day. Question: Sally, I know you are almost out the door, and it’s been a long day. If we made you the offer to come on board, what would stop you from saying 'Yes'? 4. Moment: Your idea has been called out as stupid by a subordinate in a large meeting. Question: One of the things I like most about working with Amanda is that we have agreed to always tell the truth. Amanda, let me have it. How did I mess this up? What did I overlook? 5. Moment: Your boss just asked you to take on work your team has no capacity for. Question: Gina, this sounds like a top priority. Given that the team is already overcapacity, which of our current initiatives do you think we should pause to make space for it? 6. Moment: You just finished delegating a critical piece of work. Question: Jim, it sounds like you're ready to give this a go. What is the best way for me to stay close enough to help ensure your success?" 7. Moment: You just gave a raise, and your employee is disappointed. Question: Sahil, I'm sensing you feel there's some distance between this raise and what you think you deserve. Help me understand how you thought about what was fair and what I may have missed. ⬇️⬇️⬇️ Play the game yourself: Think back to a sticky, awkward moment. Replay it, only this time: -> Don't react (with words or body language) -> Acknowledge & diffuse by labeling their reaction -> Offer a question that surfaces as much info as possible Better or worse outcome? If you found this helpful, you'll like my free newsletter even more. Subscribe: mgmt.beehiiv.com Get 70+ practical playbooks to help you manage more effectively. And please repost ♻️ and follow Dave Kline for daily leadership coaching.

“Just stop,” spat the COO 4 minutes into my sales call. “I don’t have time for this generic line of questioning.” I was two years into my first AE job. Thinking I was doing everything right. I asked open ended questions to uncover pain. Just like the sales books told me to do. Yet this COO kicked my teeth in. Leaving me and his ops manager twiddling our thumbs. “I’m as confused as you,” the ops manager said. “We teach our reps to ask the exact same questions.” Years later, I figured out what went wrong. According to data I’m sharing live tomorrow, there’s a negative correlation between asking questions to C-suite execs and closing the deal: After four questions, win rates drop. So is it a bad idea to ask c-suite execs questions? No. Here’s why win rates drop after four: 90% of reps ask sophomoric questions that make execs roll their eyes. “What are you struggling with?” “What are your biggest challenges?” “What keeps you up at night?” Those kill your chances. Asking lots of questions doesn’t close deals. Why? Because c-suite execs expect you to show up with homework. You can ask unlimited questions—if: • Your questions provide insight • Your questions spark thought • Your questions aren’t just for info-gathering Bad example: ❌ “What keeps you up at night?” Good example: ✅ “I talked to a few people in your org and discovered that you’re focused on increasing ASP and you seem to be stuck at around $50k despite selling to large enterprises. "When I hear that issue in other companies, they’re usually struggling with net retention rates – smaller deployments lead to less sticky customers. To what extent Is that being discussed at the exec level?” That shows them you get it. That show you have acumen. That gets them thinking and talking. • Start with an observation. • Lead into an insight. • Then ask a question. Save the generic stuff for the underlings. Starting tomorrow: I’m teaching everything I know about selling to the C-SUITE: • how to craft business cases that close • hard-hitting C-SUITE questions that sell • how to get access to power in every deal Join us: https://lnkd.in/gTYyPegS Sell to mid-levels? Expect mid-level commissions. Sell to the C-SUITE? Expect C-SUITE commissions.

Being an interrogenius starts with mastering the art of questioning. Great questions often matter more than great answers. Why focus on querying? 📈Sales Boost: Top salespeople ask 21% more questions, leading to better understanding and more sales (Gong.io). 📈Job Performance: Employees who regularly ask questions are rated 10% higher by their bosses for their engagement and problem-solving (Journal of Applied Psychology). 📈Innovation: 70% of breakthrough ideas come from curious employees who ask insightful questions (Harvard Business Review). How can you ask more insightful and engaging questions? 𝟭. 𝗠𝗮𝘀𝘁𝗲𝗿 𝗔𝗰𝘁𝗶𝘃𝗲 𝗟𝗶𝘀𝘁𝗲𝗻𝗶𝗻𝗴 Shut up and tune in. Really! Next meeting, try this: Listen to understand, not to reply. You'll be shocked at how much you've been missing. 𝟮. 𝗝𝗼𝗶𝗻 𝘁𝗵𝗲 𝗖𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝗖𝗹𝘂𝗯 Find a mastermind group or a Toastmasters club. Practice asking questions. Get feedback. Bonus: You'll build a network of smart colleagues. 𝟯. 𝗘𝗺𝗯𝗿𝗮𝗰𝗲 𝗬𝗼𝘂𝗿 𝗜𝗻𝗻𝗲𝗿 𝗦𝗼𝗰𝗿𝗮𝘁𝗲𝘀 That guy was onto something with his method. Ask questions that make people pause and think. It's like CrossFit for the brain. Everyone grows stronger. 𝟰. 𝗕𝗲𝗰𝗼𝗺𝗲 𝗮 𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝗼𝗻 𝗡𝗶𝗻𝗷𝗮 After conversations, ask yourself: "What could I have asked better?" It's like reviewing game tape, but for your mind. Small tweaks lead to big improvements. 𝟱. 𝗦𝗵𝗮𝗿𝗽𝗲𝗻 𝗬𝗼𝘂𝗿 𝗧𝗼𝗼𝗹𝘀 Take a course on communication. Focus on questioning techniques. Even old dogs can learn new tricks. (And yes, that includes you.) Your team will notice the difference. Trust me. 𝙒𝙝𝙮 𝙗𝙤𝙩𝙝𝙚𝙧 𝙬𝙞𝙩𝙝 𝙖𝙡𝙡 𝙩𝙝𝙞𝙨? ✅You'll uncover better solutions and ideas ✅Meetings will actually be interesting (imagine that!) ✅Develop stronger, authentic connections Great leaders aren't know-it-alls. They're learn-it-alls. So, aspiring Interrogenius, what's your first move? (See what I did there? Now it's your turn.) More resources in the comments 👇

The One Question That Will Change the Way You Connect with People Have you ever struggled to make real connections in conversations? You’re not alone. Most people stick to surface-level small talk, never unlocking the deeper, more meaningful discussions that create genuine relationships. But what if there was a simple shift that could change that? The Power of a Thoughtful Question I used to ask, “What do you do for a living?”—a question that usually led to a short, uninspiring answer. But then I tried something different: 👉 “What’s the most interesting thing you’ve been working on lately?” The response? Instant engagement. People light up, share their passions, and open up in ways I never expected. Why This Works ✅ It sparks curiosity – Instead of a routine question, you’re inviting a story. ✅ It shifts the focus – People love to talk about what excites them, not just their job title. ✅ It deepens connections – Meaningful conversations build trust and real relationships. The Science Behind It Studies show that people remember conversations where they felt heard and valued. When you ask questions that tap into someone’s enthusiasm, their brain releases dopamine—the same chemical that reinforces positive memories. Try This Today (and See What Happens in 30 Seconds!) Next time you meet someone, replace small talk with a question that invites them to share something meaningful. Here are a few to test out: • What’s one thing you’ve learned recently that really stuck with you? • What’s a challenge you’ve overcome that made you stronger? • If you could spend a day doing anything you love, what would it be? Your Challenge This week, ask one deeper question in a conversation. Then come back and comment below—what surprised you most? 🔗 Want to learn more about building authentic relationships? Check out my latest post on leadership and growth. #Leadership #Coaching #AuthenticConnections #BetterConversations #LeadershipDevelopment #PeopleFirst #CuriosityDriven #AskBetterQuestions #EffectiveCommunication

Tough conversations aren’t the problem—your questions are. 6 psychology-backed questions to build trust and influence others: 𝟭. 𝗧𝗵𝗲 𝗘𝗰𝗵𝗼 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 Just repeat their last few words as a question. 𝘛𝘩𝘦𝘮: “𝘐’𝘮 𝘯𝘰𝘵 𝘴𝘶𝘳𝘦 𝘵𝘩𝘪𝘴 𝘪𝘴 𝘵𝘩𝘦 𝘳𝘪𝘨𝘩𝘵 𝘥𝘪𝘳𝘦𝘤𝘵𝘪𝘰𝘯.” 𝘠𝘰𝘶: “𝘛𝘩𝘦 𝘳𝘪𝘨𝘩𝘵 𝘥𝘪𝘳𝘦𝘤𝘵𝘪𝘰𝘯?” People open up when they feel heard. I use this often when I sense hesitation. 𝟮. 𝗧𝗵𝗲 𝗖𝗼𝗻𝘁𝗿𝗮𝘀𝘁 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 Instead of pushing back, ask: “𝘞𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘯𝘦𝘦𝘥 𝘵𝘰 𝘤𝘩𝘢𝘯𝘨𝘦 𝘧𝘰𝘳 𝘺𝘰𝘶 𝘵𝘰 𝘴𝘦𝘦 𝘪𝘵 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵𝘭𝘺?” This shifts conflict into collaboration. I reach for this in cross-organizational conversations. 𝟯. 𝗧𝗵𝗲 𝗢𝘄𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 Rather than “𝘞𝘩𝘺 𝘥𝘰𝘯’𝘵 𝘺𝘰𝘶 𝘢𝘨𝘳𝘦𝘦?” Try: “𝘞𝘩𝘢𝘵’𝘴 𝘺𝘰𝘶𝘳 𝘱𝘦𝘳𝘴𝘱𝘦𝘤𝘵𝘪𝘷𝘦?” People drop defenses when they feel invited, not interrogated. 𝟰. 𝗧𝗵𝗲 𝗕𝗿𝗶𝗱𝗴𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 Ask: “𝘏𝘰𝘸 𝘮𝘪𝘨𝘩𝘵 𝘸𝘦 𝘴𝘰𝘭𝘷𝘦 𝘵𝘩𝘪𝘴 𝘵𝘰𝘨𝘦𝘵𝘩𝘦𝘳?” I’ve seen this melt tension in high-stakes reviews. 𝟱. 𝗧𝗵𝗲 𝗥𝗲𝗳𝗹𝗲𝗰𝘁𝗶𝗼𝗻 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 “𝘞𝘩𝘢𝘵 𝘮𝘢𝘬𝘦𝘴 𝘺𝘰𝘶 𝘴𝘢𝘺 𝘵𝘩𝘢𝘵?” A gentle prompt that gets people to examine their thinking—on their own. No judgment. Just clarity. 𝟲. 𝗧𝗵𝗲 𝗔𝗰𝘁𝗶𝗼𝗻 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 End with: “𝘞𝘩𝘢𝘵’𝘴 𝘵𝘩𝘦 𝘯𝘦𝘹𝘵 𝘴𝘵𝘦𝘱 𝘸𝘦 𝘴𝘩𝘰𝘶𝘭𝘥 𝘵𝘢𝘬𝘦?” It’s how I turn conversations into outcomes. What’s one question you rely on to spark connection? These insights are from "Doesn't Hurt to Ask: Using the Power of Questions to Communicate, Connect, and Persuade" by Trey Gowdy and brought to you by Omar's Desk. PS: The quality of your questions determines the quality of your conversations. --- Follow me, tap the (🔔) Omar Halabieh for daily Leadership and Career posts.

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

⁉ 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

"You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions." - Naguib Mahfouz Asking good questions is a powerful skill that few people master. This ability develops with practice and just being mindful about how our words affect others. Here are some reminders on crafting better questions. = Create clarity, not confusion = Instead of: "Did you follow the instructions?" Ask: "Did I provide clear enough instructions?" This keeps responsibility for clarity with you, not the listener. = Focus on solutions, not blame = Instead of: "Who forgot to order the supplies?" Ask: "How can we ensure we have the supplies we need?" This moves attention toward solving the problem rather than assigning fault. = Invite honest dialogue = Instead of: "Why are you resistant to this change?" Ask: "What concerns do you have about this new approach?" This opens space for reflection instead of triggering defensiveness. = Remove implicit authority = Instead of: "This is the best option, right?" Ask: "How do you evaluate the different options available?" This seeks genuine input rather than just requesting agreement with your position. = Encourage reflection, not defense = Instead of: "Why did the customer complaint numbers increase?" Ask: "What factors might be contributing to the recent customer feedback?" This creates room for honest assessment without forcing justification. Good questions build trust. They show respect. They lead to better answers and stronger relationships. A well-crafted question can transform a conversation. Learn this art. Your wisdom will show.

Most people talk.  Few truly connect.  Be the exception. Asking smarter questions is key. Open-ended questions drive deeper dialogue. Here are 6 Techniques to master this skill: 1️⃣ Start with "How," "What," or "Why": ↳ These words invite detailed responses. ↳ They shift conversations from surface level to meaningful. 2️⃣ Clarify Assumptions: ↳ Ensure everyone understands the topic clearly. ↳ This prevents miscommunications and builds trust. 3️⃣ Use Follow-Up Questions: ↳ Dig deeper into initial responses. ↳ Uncover the rationale behind decisions. 4️⃣ Embrace Silence: ↳ Pauses give people time to think. ↳ Thoughtful answers lead to massive contributions. 5️⃣ Avoid Leading Questions: ↳ Stay neutral to encourage honest sharing. ↳ Authentic responses are more valuable. 6️⃣ Cultivate Curiosity: ↳ Show genuine interest in others' perspectives. ↳ Create a safe space for open discussion. These strategies enrich interactions. They foster collaboration and innovation. Mastering the art of asking smarter questions leads to better outcomes. Stay curious. Stay engaged. And stay open-minded. ♻️ Share this to enhance your conversations and professional growth. 🚀 Join 66,000+ leaders reading my daily science-backed tips on leading high-performing teams using mindset, habits and systems. No vague recommendations. All backed by science and experience. ➡️ Follow me here Harry Karydes

If your discovery questions start with “What’s wrong with…” You’re already losing. Old school discovery says: dig into their emotion. Modern discovery says: inspire until they believe. Most reps default to problem probing: “What’s broken?” “What’s hard?” “What’s blocking progress?” The intent is right. The framing is wrong. Buyers don’t want a therapy session. They want momentum. Here’s how to flip your discovery questions, and flip the outcome: 🔁 Instead of: “What’s your biggest challenge?” ✅ Ask: “What would a breakthrough look like this quarter?” 🔁 Instead of: “Why haven’t you solved this yet?” ✅ Ask: “What’s been missing from past attempts?” 🔁 Instead of: “What keeps you up at night?” ✅ Ask: “What gets you excited to win this year?” 🔁 Instead of: “Why now?” ✅ Ask: “What shifts if you nail this in the next 90 days?” 🔁 Instead of: “What’s the risk of inaction?” ✅ Ask: “What’s the upside of acting fast?” Language changes emotion. Emotion changes urgency. Urgency changes deals. Reps who master this don’t just ask better questions. They create better conversations. #sales #salesstrategy