How to Persuade by Questioning the Status Quo

"I have a bone to pick with you." That's how I opened a recent conversation with an executive. Spoiler: It didn't land well. 🫠 (𝘐’𝘮 𝘴𝘸𝘦𝘢𝘵𝘪𝘯𝘨 𝘴𝘩𝘢𝘳𝘪𝘯𝘨 𝘵𝘩𝘪𝘴 𝘰𝘯 𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯, 𝘣𝘶𝘵 𝘐 𝘣𝘦𝘭𝘪𝘦𝘷𝘦 𝘪𝘯 𝘯𝘰𝘳𝘮𝘢𝘭𝘪𝘻𝘪𝘯𝘨 𝘮𝘪𝘴𝘵𝘢𝘬𝘦𝘴, 𝘴𝘰 𝘩𝘦𝘳𝘦 𝘪𝘵 𝘨𝘰𝘦𝘴.) I came in with a strong point of view, ready to advocate for my position. It was in opposition to a decision she made but that could still be changed. "She'll appreciate that I have conviction!" I thought confidently. But instead of sparking a productive debate, I miscalculated. The executive gently stopped me. She offered advice I'll never forget and have been thinking about days since: "Consider the context around how I made this decision." In that moment, I realized I'd skipped a crucial step: curiosity before challenge. Here's what I learned about challenging up, why my approach was all wrong, and what you can learn from my mistake. This advice is great if you're a current or aspiring #chiefofstaff but also applicable to anyone working to improve their persuasion skills. 1️⃣ 𝗟𝗲𝗮𝗱 𝘄𝗶𝘁𝗵 𝗰𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝗯𝗲𝗳𝗼𝗿𝗲 𝗰𝗼𝗻𝘃𝗶𝗰𝘁𝗶𝗼𝗻. Instead of jumping in with a firm stance, start with, "I'm curious how you landed on this decision." This simple shift creates space for dialogue. It might even change your perspective before you voice your challenge. (In my case, as soon as I had more context, I changed my tune. If only I had led with curiosity...) 2️⃣ 𝗞𝗻𝗼𝘄 𝘄𝗵𝗲𝗻 𝘁𝗼 𝗯𝗿𝗶𝗻𝗴 𝗮𝗻 𝗶𝗻𝗳𝗼𝗿𝗺𝗲𝗱 𝗼𝗽𝗶𝗻𝗶𝗼𝗻 𝘃𝘀. 𝗮 𝘀𝘁𝗿𝗼𝗻𝗴 𝗣𝗢𝗩. Here's how I think about the difference: An informed opinion means you've thought critically but remain open to learning; a strong point of view (POV) usually means you've already decided the best course of action and are looking for buy-in. Generally, if the decision is in your domain/area of expertise, it's good to have your recommendation (POV) ready. For broader strategic decisions, almost always seek to understand first. 3️⃣ 𝗙𝗿𝗮𝗺𝗶𝗻𝗴 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 — 𝗮 𝗹𝗼𝘁. Compare "I disagree with this approach" to "Here's something I've been thinking about. Could I share my perspective?" Both convey your conviction, but one does it WAY more effectively. The former shuts down dialogue; the latter invites discussion. This experience taught me an important truth: The most effective persuaders aren't just those with strong convictions. They're the ones who master the dance between inquiry and advocacy. 💃 And even in an AI-driven world, persuading other humans will continue to be an in-demand skill. Whether you're early in your career or sitting at the executive table, understanding this balance can transform how your points are received. It might even change some strong opinions you thought you had. It did for me. (𝘛𝘩𝘪𝘴 𝘱𝘰𝘴𝘵 𝘸𝘢𝘴 𝘸𝘳𝘪𝘵𝘵𝘦𝘯 𝘣𝘺 𝘢𝘯 𝘰𝘷𝘦𝘳𝘵𝘩𝘪𝘯𝘬𝘪𝘯𝘨 𝘩𝘶𝘮𝘢𝘯, 𝘯𝘰𝘵 𝘈𝘐.)

Most discovery calls feel like an interrogations. Question. After question. After question. “What are you measuring?” “What is it today?” “Where do you want it to be?” “What happens if you do nothing?” “What’s the value of the difference?” Prospects leave lighter, but none the wiser. Want to disrupt the status quo? Bring a point of view that rattles the tray. Look at Enzo Avigo, CEO at June.so. He doesn’t just ask founders about churn. He says, “Your activation metric is lying to you.” Then drops a new lens that reframes the whole dashboard. Suddenly SaaS leaders see a problem they didn’t even have a name for. And June is the only company talking about the cure. You can do the same in discovery calls. Step one: expose an assumption. “Most teams treat last touch attribution like gospel.” Step two: swap in a sharper frame. “The problem is data shows that first‑encounter moments predict revenue far better.” Step three: invite them into the story. “Would you be open to hearing a different perspective on how teams capturing those moments and CAC by up to 30%?” Now you’re not probing; you’re teaching. You’re the guide who names the monster hiding under their bed and flips on the light so they can finally see it. Questions still matter. But when they ride shotgun with a clear point of view, you stop sounding like every other rep and start sounding like the partner who rewrote the playbook. That’s how you win. Not by gathering answers, but by giving people a new question they can’t stop asking themselves

😬 Your organization isn't afraid of questions. It's afraid of what questions reveal... I was talking with a CEO last month. He realized the same fear existed at every company level, from the C-suite to frontline employees. When he questioned his executives, they felt "nitpicked." When managers questioned junior staff, they feared for their jobs. Different symptoms, same disease: a question-averse culture. Here's the paradox: In a world demanding agility and innovation, the companies that can't question themselves won't survive. Yet, most organizations subconsciously punish curiosity. It's command and control, production-like behavior. The highest-performing teams I've coached don't avoid questions – they run toward them. They've built cultures where questions signal interest, not inspection. Three actions to transform your question-averse culture: 🧐 Make the invisible visible  Most leaders have never explicitly discussed how questions should be received. Have the conversation. Name the fear. Acknowledge that defensiveness is natural but unproductive. Make it clear: "In this organization, questions mean investment, not judgment." ❓Question your questioning Ask yourself: "How am I framing my questions?" Questions that begin with "why" often trigger defensiveness. Questions that start with "what" or "how" invite collaboration. Slight shift, profound impact. Instead of "Why did you do it that way?" try "What factors influenced your approach?" 📢 Reward those who challenge you  Nothing speaks louder than who gets rewarded. Publicly acknowledge team members who question your thinking or approach (especially when they were right). When someone changes direction after being questioned, celebrate their adaptability, not their "mistake." The companies winning today aren't the ones with all the answers. They're brave enough to question everything, especially their assumptions. Get curious. Ask questions. Don't hold back.

Forget "fake it till you make it." It's time to embrace "ask it till you grasp it." The most powerful tool in your leadership toolkit? Asking seemingly simple questions. Throughout my career, I've noticed a paradox: The most effective leaders often ask great questions that guide the team, rather than solely giving direction. They're not afraid to ask questions that might make them appear less knowledgeable. What these leaders understand is that asking questions is the key to effective communication. It opens dialogues, clarifies understanding, and builds stronger connections. ---5 Simple Questions to Start Using--- 🔸"Can you explain that as if I'm new to this topic?" (Ensures clear communication, reveals assumptions) 🔸"What if our current approach is incorrect?" (Challenges assumptions, prevents groupthink) 🔸"Why do we do it this way?" (Questions status quo, sparks innovation) 🔸"What am I missing here?" (Acknowledges blind spots, invites diverse viewpoints) 🔸"How can I be less of a bottleneck?" (Demonstrates self-awareness, empowers team) The catch? It can feel uncomfortable at first.   ----The beauty of this simple action---- 🔹Simple questions get everyone on the same page quickly 🔹Simple approaches are easier to communicate and replicate 🔹Simplicity cuts through complexity, leading to clearer insights 🔹Simple questions (like these) are more likely to be tried and tested   Your job is to create an environment where smart ideas can emerge from anyone. Your challenge: This week, ask the simplest, most fundamental question you can think of in your next team meeting. What's the most basic question you've asked that led to a breakthrough?  

“Why don’t you agree with me?” Ever been asked that in a meeting? It’s a trap. 👉🏼 Let's not silence voices with bad questions. I’ve seen brilliant minds shut down in rooms where they felt cornered. > A junior engineer who had the answer, but held it in. > A nurse who saw the risk, but said nothing. > A woman who knew the solution but had learned not to challenge. All because someone asked the wrong question. Let’s break that pattern, one better question at a time. Here’s how: 💬 Silencing Question: “Why don’t you agree with me?” ✅ Dialogue Question: “How do you see it differently?” It shifts from defensiveness to curiosity. From ego to exploration. 💬 Silencing Question: “What’s your problem with this?” ✅ Dialogue Question: “What concerns or hesitations do you have about this?” It replaces judgment with psychological safety. 💬 Silencing Question: “Do you agree with what was said?” ✅ Dialogue Question: “What’s your take? What would you add, challenge, or change?” It invites contribution, not compliance. 💬 Silencing Question: “Why are you so quiet?” ✅ Dialogue Question: “What’s on your mind that we haven’t heard yet?” It opens the door instead of putting someone on the spot. 💬 Silencing Question: “Is that really important right now?” ✅ Dialogue Question: “Tell me more about why this matters to you.” It validates values instead of dismissing them. 💬 Silencing Question: “Does this make sense?” ✅ Dialogue Question: “What questions does this bring up for you?” It assumes confusion is normal and welcome. 👉🏼 Leadership isn’t about having the answers. It’s about asking better questions: the kind that pulls people in, not shuts them down. When people feel safe to speak, innovation flows. Problems get solved. Teams thrive. So let’s help others stop shutting people down and start unlocking their voices. 👉 Follow me for more tips on how to empower voices at work. #leadershipdevelopment #employeelistening #communicationtips #speakupculture #psychologicalsafety #inclusiveleadership #employeevoice #teameffectiveness #leadershipskills #hrleaders #learninganddevelopment #ergleaders #corporateculture #peopleleaders #assertivecommunication

I am a naturally curious person. That shows up constantly in how I collaborate within, lead, and manage teams—I ask A LOT of questions. But I’ve learned that sometimes questions can make people uncomfortable. I've always wondered if it's because "curiosity killed the cat" was drilled into many kids in my generation as a way to shut them up or get them to comply without questioning authority. 😬 I've seen questions frequently misinterpreted as active criticism or, a lack of confidence in someone’s abilities. Other times, they’re seen as veiled subtext—like there’s a hidden meaning or agenda. I wish more people felt that questions are not threats. I believe deeply that they’re a way to make ideas stronger, to create deeper understanding of problems, and to get everyone rowing in the same direction. And when a team or culture views questions as inherently good, the outcomes are always better. How do we make curiosity feel safe, not threatening? Here’s what I’ve learned: -Detach Questions from Personal Performance: Questions should be about the idea. Period. If you’re probing a decision or digging into a plan, make it clear that you’re focused on the what, not the who. This keeps conversations productive and collaborative. - Be Clear About Why You’re Asking: If you’re a leader—or just someone who asks a lot of questions—share your intent. Say things like, “I’m just trying to understand this better” or “Can you help me connect the dots here?” This kind of framing goes a long way in diffusing any defensiveness. -Model and Create Space for Curiosity Openly: When you’re curious, be curious out loud. Ask questions in meetings. Admit when you don’t know something. Show your team that it’s not only okay to ask—it’s expected. Build a culture where there’s always room for people to say, “Wait, can you say more on that?' -Use Verbal Disclaimers: I have picked up the habit of saying things I used to assume was understood, out loud. Things like "this is not criticism" or "this question is to help me understand you perspective to be a better collaborator." This helps set up a shared goal between parties to work toward. -Celebrate Good Questions: When someone asks a question that shifts perspective or sparks a better solution, call it out. Let people know that curiosity is valued and rewarded. Other naturally curious folks—I'd love to hear your thoughts. Have you encountered this at work?

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!)