Mastering Questioning Skills

I responded to a cold email: “This isn’t my priority. Best of luck with your outreach!” Got hit with an objection handle: “Just to confirm - closing more deals faster isn’t a priority?” I get the approach: The idea is to “trap” the prospect into a question they can’t say no to. “What sales leader wouldn’t want more deals, faster?” Here’s the problem: I’m not objecting to the proposed outcome. Closing more deals faster is ALWAYS a priority for me. I’m just already working on my top priorities to help my teams close more deals faster. We’ve identified tools supporting those priorities and are in execution mode. My objection wasn’t to the outcome. It was the approach this solution takes to drive that outcome. The problems they solve to drive that outcome are not painful for me. When you get a no, don’t fall back to the high-level outcome: - “Oh, you don’t want to save money on your HR solutions?” - “Really, you don’t want to reduce the risk of getting hacked?” - “Huh, you don’t want your developers to be happy and productive?” Of course your buyers want those outcomes. If they are objecting, they likely either: - Don’t believe you can drive that outcome - Believe a different approach will work better Find out which of those your objection falls under and address that for better success. Here’s what that follow-up might look like: “Makes perfect sense you’ve already got a handle on this. Usually this means you’ve got a similar solution in place and I didn’t do a good job sharing how we are different, or you are attacking this priority through a completely different approach. Can I ask where you fall?” Next time you hear “this isn’t a priority” to something that you know should be a priority, give this a shot!

The Art of Asking Questions - The most important skill in Corporates One of the most valuable skills in the corporate world is knowing how to ask the right questions. Over time, I’ve realized that good questions don’t just gather information—they shape discussions, uncover insights, and drive decisions. Here’s what I’ve learned: 1. Don’t ask for the sake of asking. Thoughtless questions add noise, not value. A well-placed question shows genuine curiosity and strategic thinking. 2. Always follow up if you’re not satisfied. If an answer feels incomplete or vague, don’t hesitate to probe deeper. The best insights often come from follow-up questions. 3. Frame your questions well. Instead of asking, “Is the company doing well?”, ask, “What key metrics indicate the company’s growth this quarter?” Precision matters. 4. Be an active listener. The best questions come from truly understanding the discussion. Don’t just wait for your turn to speak—engage with the responses. 5. Challenge assumptions. Don’t take things at face value. A simple “Why do we do it this way?” can lead to breakthrough ideas and efficiency improvements. 6. Ask open-ended questions. Avoid questions that lead to simple “yes” or “no” answers. Instead of “Did you like the project?”, ask, “What aspects of the project worked well, and what could be improved?” 7. Read the room. Timing and context are everything. The right question at the right moment can change the direction of a conversation entirely. Mastering the art of asking questions can set you apart in any professional setting. What’s a question that has helped you unlock valuable insights at work? Let’s discuss! #CareerGrowth #CorporateSkills #AskingTheRightQuestions #Communication

𝗡𝗲𝘄 𝘁𝗼 𝗖𝗼𝗿𝗽𝗼𝗿𝗮𝘁𝗲? 𝗬𝗼𝘂𝗿 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗖𝗮𝗻 𝗠𝗮𝗸𝗲 𝗼𝗿 𝗕𝗿𝗲𝗮𝗸 𝗬𝗼𝘂 When I started as a research analyst in my 20s, I thought my work would speak for itself. It didn’t. Turns out, being good at your job isn’t enough—how you communicate matters just as much. Here’s what I learned the hard way: 𝗜𝗳 𝗬𝗼𝘂’𝗿𝗲 𝗦𝗶𝗹𝗲𝗻𝘁, 𝗣𝗲𝗼𝗽𝗹𝗲 𝗔𝘀𝘀𝘂𝗺𝗲 𝗬𝗼𝘂 𝗛𝗮𝘃𝗲 𝗡𝗼𝘁𝗵𝗶𝗻𝗴 𝘁𝗼 𝗦𝗮𝘆 Early on, I stayed quiet in meetings, thinking I needed more experience before contributing. Big mistake. 📌 Fact: People who speak up in the first 10 minutes of a meeting are more likely to be remembered. 📌 My fix? I made it a rule to say at least one relevant thing per meeting—even if it was just a question. 𝗢𝘃𝗲𝗿𝗰𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗲, 𝗕𝘂𝘁 𝗞𝗲𝗲𝗽 𝗜𝘁 𝗦𝗺𝗮𝗿𝘁 At first, I either gave too little detail or way too much. Now, I structure my updates like this: 🔹 What I’m working on 🔹 What I need help with 🔹 What’s next This keeps things clear, saves time, and makes me look more in control. 𝗘𝗺𝗮𝗶𝗹𝘀 & 𝗠𝗲𝘀𝘀𝗮𝗴𝗲𝘀: 𝗠𝗮𝗸𝗲 𝗜𝘁 𝗘𝗮𝘀𝘆 𝘁𝗼 𝗥𝗲𝗮𝗱 No one has time to read long emails. My golden rule? One glance = instant clarity. ✔ Use bullet points ✔ Keep paragraphs short ✔ Highlight key takeaways Result? Faster replies, less back-and-forth. 𝗟𝗲𝗮𝗿𝗻 𝗛𝗼𝘄 𝗬𝗼𝘂𝗿 𝗠𝗮𝗻𝗮𝗴𝗲𝗿 𝗟𝗶𝗸𝗲𝘀 𝘁𝗼 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗲 Some prefer Slack, some prefer calls, and others like a quick email summary. Adjusting to their style = better alignment & fewer misunderstandings. 𝗧𝗵𝗲 𝗠𝗼𝘀𝘁 𝗨𝗻𝗱𝗲𝗿𝗿𝗮𝘁𝗲𝗱 𝗦𝗸𝗶𝗹𝗹? 𝗔𝘀𝗸𝗶𝗻𝗴 𝘁𝗵𝗲 𝗥𝗶𝗴𝗵𝘁 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 I used to be afraid of asking questions. Now, I realize good questions make you look sharp. Instead of: ❌ "I don’t understand this." Try: ✅ "Could you clarify X so I can align my approach?" Mastering communication isn’t about talking more—it’s about talking smarter. What’s one communication tip that helped you at work? Drop it in the comments! ⬇️ #CorporateLife #CommunicationSkills #CareerGrowth #LessonsFromExperience

Top reps ask 4x more implication questions than average ones. Here’s why SPIN Selling still works. Most reps jump straight into pitch mode. They ask a few surface questions, then start talking features. That’s not selling. That’s presenting. SPIN flips the script. It gets the buyer to sell themselves. Start with Situation questions. Learn their current state, but keep it short. Experienced reps ask fewer of these than you’d expect. Move to Problem questions. Uncover what’s not working. Where they’re stuck. What’s costing them time or money. This is where small deals get won. But for complex sales, you need more. That’s where Implication questions come in. Show the consequences of inaction. What does this problem cost them? How does it affect other areas? What’s the revenue impact? Top performers ask these 4x more than average reps. They build urgency without being pushy. Finally, Need-Payoff questions. Let the buyer articulate the value. How would solving this help? What would the impact be? Why is this important? When they say it, they believe it. Here’s the key insight: Buyers don’t just want you to solve their problems. They want to understand why solving them matters. SPIN gives you the framework to guide that conversation. Not through charm. Not through pitch decks. But through the right questions in the right order. Save this framework. Use it on your next discovery call. Watch how fast urgency builds.

𝐖𝐡𝐲 𝐛𝐞𝐢𝐧𝐠 𝐠𝐨𝐨𝐝 𝐚𝐭 𝐟𝐨𝐥𝐥𝐨𝐰-𝐮𝐩 𝐪𝐮𝐞𝐬𝐭𝐢𝐨𝐧𝐬 𝐦𝐚𝐤𝐞𝐬 𝐲𝐨𝐮 𝐚 𝐛𝐞𝐭𝐭𝐞𝐫 𝐚𝐧𝐚𝐥𝐲𝐬𝐭 𝐭𝐡𝐚𝐧 𝐰𝐫𝐢𝐭𝐢𝐧𝐠 𝐥𝐨𝐧𝐠𝐞𝐫 𝐪𝐮𝐞𝐫𝐢𝐞𝐬 In real analytics work, most mistakes don’t happen because someone doesn’t know SQL. They happen because the analysis starts without fully understanding the problem. You can write a long, technically correct query and still deliver the wrong insight if the question itself wasn’t clear. Over time, I’ve noticed that strong analysts don’t rush into querying. They slow down at the beginning and ask better follow-up questions. These questions shape the analysis before any code is written, and that’s what saves time and improves impact. 𝐇𝐞𝐫𝐞’𝐬 𝐰𝐡𝐲 𝐟𝐨𝐥𝐥𝐨𝐰-𝐮𝐩 𝐪𝐮𝐞𝐬𝐭𝐢𝐨𝐧𝐬 𝐦𝐚𝐤𝐞 𝐬𝐮𝐜𝐡 𝐚 𝐛𝐢𝐠 𝐝𝐢𝐟𝐟𝐞𝐫𝐞𝐧𝐜𝐞 - They help you understand the real intent behind the request, not just the surface wording They expose hidden assumptions about metrics, time windows, or user segments They reduce rework, because you don’t have to redo the analysis later They improve decision quality, since the analysis stays aligned with the actual problem They build trust, because stakeholders feel heard and understood A good analyst often starts with questions like: What decision will this analysis support? Which definition of the metric are we using? What time period actually matters here? Only after these are clear does SQL come into play. Long queries are easy to learn with practice. Asking the right follow-up questions is what makes your analysis useful.

You know that sinking feeling… Someone interrupts your carefully prepared presentation with “But what about...?” and raises a point you never considered. Everyone is looking at you, and you feel the weight of the world on your shoulders. In that moment, the idea or solution you’ve been presenting weighs in the balance. Address the resistance well, and your idea will likely be adopted with even more optimism than before. Address it poorly, and your idea is as good as gone. Here’s a quick overview of my “RAP” formula that you can use in these moments to turn blindside objections into “aha” moments. 1. R: Recognize the type of resistance you’re facing: - Logical resistance (conflicting data or reasoning) - Emotional resistance (values or identity challenges) - Practical resistance (implementation concerns) 2. A: Address it proactively in your presentation: - For logical resistance: Acknowledge competing viewpoints before they’re raised. "Some might point to last quarter’s numbers as evidence against this approach. Here’s why that perspective is incomplete..." - For emotional resistance: Connect your idea to their existing values. "This initiative actually strengthens our commitment to customer-first thinking by..." - For practical resistance: Demonstrate you’ve considered the real-world constraints. "I know this requires significant change. Here’s our phased implementation plan that accounts for..." 3. P: Provide a path forward that transforms resistance into alignment: - Give them space to voice concerns (but in a structured way) - Incorporate their perspective into the solution - Show how addressing their resistance actually strengthens the outcome The most powerful thing you can say in a presentation isn’t "trust me", it’s "I understand your concerns." When you genuinely see resistance as valuable feedback rather than an obstacle, you’ll find your ideas gaining traction where they previously stalled. #CommunicationSkills #BusinessCommunication #PresentationSkills

Last Friday, 175 professional women in Singapore each handed me one ASK. 104 of them were the same ASK 👉 An introduction to a specific person they could not reach on their own. The ones who walked away with a real outcome were not the most senior. They were the ones who had three skills, in sequence, that almost no woman is taught. 𝗦𝗸𝗶𝗹𝗹 𝟭. 𝗧𝗵𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻. A sharp ask shrinks the senior person's network, on their behalf, to one specific person they can already see in their head. A stalled ask widens the room. "I am open to opportunities." They have to imagine your industry and their network. So they do nothing. A sharp ask narrows it to one person. "I am moving from Regional Marketing Director into a CMO seat in the next twelve months. Who in your last six months of meetings is the Board Chair who could tell me what the first year of that transition actually cost her." It names a destination. It dates it. It tells them which corner of their network to scan. And what the meeting is for. If you cannot ask in two sentences and have them nodding by the second, it is not ready. This skill does ninety percent of the work. 𝗦𝗸𝗶𝗹𝗹 𝟮. 𝗧𝗵𝗲 𝗛𝗼𝘄. Senior people do not say no to senior women. They say "let me think about who" and forget by the next meeting. The how is what you write for them before they need it. Bring the introduction email already drafted. Three sentences about you, two about why this person, one on what you want the meeting to do. Say: "I have written what you could forward. Edit anything, take my name off if you prefer." You are not putting words in their mouth. You are removing the cognitive load that stops busy people from helping. The how is good when they make one edit and forward the draft the same day. 𝗦𝗸𝗶𝗹𝗹 𝟯. 𝗧𝗵𝗲 𝗙𝗼𝗹𝗹𝗼𝘄-𝘂𝗽. This decides whether the same person will spend capital on you a second time, or never. Within 48 hours, write back. Not "thank you so much." A specific sentence. "Introduction landed yesterday. Meeting Thursday at 4pm. Will tell you what I learn." After the meeting, close the loop. "Met her Thursday. The first year of that transition cost her two things she had not anticipated. I am rethinking the timing of my move. Thank you. It changed the question I am asking." A senior person who sees their action produced a result will spend capital again. One who never hears back will not. Most senior women lose the relationship here. In the silence after the ask. The three compound. ✔️ A question without a how puts the burden back. ✔️ A how without a question is a forwarded email to nowhere. ✔️ Both without a follow-up is a one-time favour. If you have been waiting to be discovered for two years, the gap is the three sentences you have not yet learned to write. We built a course for that. It is called From Mentored to Championed. The full sponsorship playbook, Link in comment

If you’re in sales, chances are you’ve had to start a conversation with strangers. We open conversations so frequently that we take the art of opening for granted. That’s a tragedy because a good opening can inspire people to care and motivate them to want to learn more. But you lose that ability if you don’t realize opening is a skill that can be learned and mastered. How do you become a better opener? Shift from pitching to asking. Pitching sounds like this: “We discovered a breakthrough in email deliverability that enables you to avoid spam folders. The reason for my call is to share this breakthrough with you.” Asking sounds like this: “When managing cold email deliverability, are you handling it manually—removing invalid emails, monitoring blacklists, setting up SPF, DKIM, and DMARC—or is it automated?” Here’s why asking works: 1. Builds Curiosity: Asking about their process makes the prospect reflect on their own approach. This illuminates gaps they might not have considered. This curiosity can lead them to naturally want to know more about your solution. 2. Doesn’t Feel Pushy: Solutions have no value with a problem. Instead of pitching a solution, asking puts the focus on understanding if there’s a problem. When you let go of assumptions you lower resistance. 3. Establishes Relevance: When you ask about the specific steps they’re taking (e.g., managing blacklists, setting up SPF, DKIM), you’re showing that you understand the technical aspects of their world. This demonstrates credibility and positions you as someone who “gets it.” The takeaway? It’s not your job to fill people’s heads with information. Your job is to draw it out. Buyers have the answers. Sellers have the questions. To be a better closer, be a better opener.

How I get genuine feedback from my clients (5 game-changing questions you haven’t asked yet) In business, the feedback you receive feels like a well-rehearsed script hastily delivered. It's a phenomenon I call the Echo Chamber Effect - where the feedback we receive is just an echo of what we want to hear, not what we need. Here’s what happens: You think you're ticking all the boxes: - client satisfaction, - exceptional service, - open communication… And then, out of nowhere, you're out of a job. Or - your services are abruptly canceled. You’re blindsided. But were you? Or did you just ask the wrong questions all along? Here are 5 powerful, open-ended questions that you should ask: 1.) “𝘞𝘩𝘢𝘵'𝘴 𝘵𝘩𝘦 𝘰𝘯𝘦 𝘵𝘩𝘪𝘯𝘨 𝘺𝘰𝘶 𝘸𝘪𝘴𝘩 𝘸𝘦 𝘸𝘰𝘶𝘭𝘥 𝘴𝘵𝘰𝘱 𝘥𝘰𝘪𝘯𝘨?" This invites honest critique, not just polite nods. 2.) “𝘐𝘧 𝘺𝘰𝘶 𝘸𝘦𝘳𝘦 𝘪𝘯 𝘮𝘺 𝘴𝘩𝘰𝘦𝘴, 𝘸𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘺𝘰𝘶 𝘤𝘩𝘢𝘯𝘨𝘦 𝘢𝘣𝘰𝘶𝘵 𝘰𝘶𝘳 𝘴𝘦𝘳𝘷𝘪𝘤𝘦/𝘱𝘳𝘰𝘥𝘶𝘤𝘵?" This encourages the respondent to offer insights you might have overlooked. 3.) “𝘊𝘢𝘯 𝘺𝘰𝘶 𝘩𝘦𝘭𝘱 𝘮𝘦 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘸𝘩𝘢𝘵'𝘴 𝘮𝘪𝘴𝘴𝘪𝘯𝘨 𝘪𝘯 𝘰𝘶𝘳 𝘤𝘶𝘳𝘳𝘦𝘯𝘵 𝘢𝘱𝘱𝘳𝘰𝘢𝘤𝘩?" This is a collaborative invitation, making the respondent a partner in problem-solving. 4.) “𝘐𝘮𝘢𝘨𝘪𝘯𝘦 𝘸𝘦'𝘳𝘦 𝘮𝘦𝘦𝘵𝘪𝘯𝘨 𝘢 𝘺𝘦𝘢𝘳 𝘧𝘳𝘰𝘮 𝘯𝘰𝘸 𝘤𝘦𝘭𝘦𝘣𝘳𝘢𝘵𝘪𝘯𝘨 𝘰𝘶𝘳 𝘴𝘶𝘤𝘤𝘦𝘴𝘴; 𝘸𝘩𝘢𝘵 𝘥𝘪𝘥 𝘸𝘦 𝘥𝘰 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵𝘭𝘺?" This question not only seeks feedback but also fosters a vision of shared success. 5.) “𝘐𝘧 𝘺𝘰𝘶 𝘸𝘦𝘳𝘦 𝘵𝘰 𝘳𝘦𝘤𝘰𝘮𝘮𝘦𝘯𝘥 𝘶𝘴 𝘵𝘰 𝘢 𝘧𝘳𝘪𝘦𝘯𝘥, 𝘸𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘺𝘰𝘶 𝘴𝘢𝘺?" This helps gauge the perceived value and authenticity of your service or product. Remember, it's not about interrogating. It’s about engaging in a meaningful dialogue. P.S. What other questions would you add to this list?

IN THE AGE OF AI, THE COMPETITIVE ADVANTAGE HAS SHIFTED FROM KNOWING MORE TO ASKING BETTER QUESTIONS For centuries, the person with the answers had the advantage. Knowledge was indeed power. Teachers, doctors, lawyers, consultants, executives, and experts built their value on what they knew. Information was scarce. Experience gave you access to answers that others didn't have. Success depended on accumulating knowledge. In today’s world, AI has democratized knowledge. Anyone can generate explanations, strategies, code, research or ideas in seconds. When everyone has access to answers, answers themselves stop being the advantage. The real differentiator is the quality of the questions we ask. Technology amplifies thinking—but only if we give it something worth thinking about. A mediocre question produces a mediocre answer, no matter how powerful the technology. A brilliant question unlocks insights that others never even think to explore. AI has commoditized information. It hasn't commoditized judgment. And judgment begins with asking the right question. Hence the quality of your future will increasingly depend on your ability to ask the right questions. And here is where the difference between average and exceptional has shifted from "What do you know?" to "What are you curious enough to ask?", making “INTELLECTUAL CURIOSITY” one of the most valuable leadership traits of our time. In our business of Executive search, the best consultants don't impress clients with what they know but by asking questions that make the client pause and think. The best CEO/CXOs don't claim to have all the answers either. Their greatest strength lies in asking the one question that changes everyone else's thinking. When I started my entrepreneurial journey, I wasn't carrying a bag full of answers. I was carrying a notebook full of questions. I wasn't an industry insider and had no blueprint to follow. What I did have was relentless curiosity. By questioning assumptions others accepted, I discovered opportunities others overlooked. Looking back, every meaningful breakthrough in my career began with a question—not an answer. The best leaders today are the ones who create environments where people ask difficult questions. “What are we ignoring?” “What would our customer disagree with?” “If we started this company today, would we build it this way?” “What problem are we solving that AI can't?” Every innovation begins as a question. Every disruption starts with someone asking, "Why does it have to be this way?" In an AI-driven world, what will matter most is framing problems. Knowledge will remain important, but curiosity will become the multiplier. The professionals who will thrive over the next decade won't necessarily be those who know the most but those who can think the deepest & consistently ask questions others wont think of asking.      #ArtificialIntelligence #Leadership #IntellectualCuriosity #FutureOfWork