How to Challenge Ideas Without Criticizing Colleagues

"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.)

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?

🔥 Stop asking these 5 questions. They’re silently killing your team’s trust. I’ve seen it happen more times than I can count. One leader walks into a meeting. Asks one question. And the whole room shuts down. People stop breathing. They look down. They give the “safe” answer. And just like that: → Trust? Gone. → Momentum? Dead. → Innovation? Don’t even bother. It wasn’t the tone. It wasn’t the setting. It was the 𝘲𝘶𝘦𝘴𝘵𝘪𝘰𝘯. Some questions don’t build insight. They build fear. And fear kills progress. Here are 5 questions smart leaders stop asking (and what they ask instead): 𝟭/ “𝗪𝗵𝘆 𝗱𝗶𝗱𝗻’𝘁 𝘆𝗼𝘂…?” 👎 Signals blame   ↳ People shut down to protect themselves ✅ Ask instead: “What got in our way here?” 💡 Shifts focus from fault to feedback 𝟮/ “𝗪𝗵𝗼’𝘀 𝗿𝗲𝘀𝗽𝗼𝗻𝘀𝗶𝗯𝗹𝗲 𝗳𝗼𝗿 𝘁𝗵𝗶𝘀 𝗺𝗶𝘀𝘁𝗮𝗸𝗲?” 👎 Sounds like: “Who’s getting fired?”   ↳ No one learns, everyone hides ✅ Ask instead: “What can we learn from this?” 💡 Creates safety and makes mistakes useful 𝟯/ “𝗗𝗼𝗻’𝘁 𝘆𝗼𝘂 𝘁𝗵𝗶𝗻𝗸 𝘄𝗲 𝘀𝗵𝗼𝘂𝗹𝗱…?” 👎 This is just your opinion in disguise ↳ Blocks real dialogue from the start ✅ Ask instead: “What’s your take on this?” 💡 Invites ownership and builds trust 𝟰/ “𝗪𝗵𝘆 𝗰𝗮𝗻’𝘁 𝘆𝗼𝘂 𝗯𝗲 𝗺𝗼𝗿𝗲 𝗹𝗶𝗸𝗲 [𝗽𝗲𝗿𝘀𝗼𝗻]?” 👎 Comparison kills motivation   ↳ It never inspires, it only isolates ✅ Ask instead: “What support do you need?” 💡 Shifts from judgment to growth 𝟱/ “𝗛𝗮𝘃𝗲𝗻’𝘁 𝘆𝗼𝘂 𝗳𝗶𝗻𝗶𝘀𝗵𝗲𝗱 𝘁𝗵𝗮𝘁 𝘆𝗲𝘁?” 👎 Signals impatience and disconnect   ↳ Implies laziness before understanding reality ✅ Ask instead: “What obstacles are you facing?” 💡 Be a partner, not a critic 🧨 The Hard Truth: You don’t lose trust with big betrayals. You lose it with small questions that feel like traps. If your people aren’t speaking up… It’s not because they don’t have ideas. It’s because they don’t feel safe. Great leaders ask questions that pull people in. Not push them away. So check your questions. Because your words aren’t just words. They shape the culture your team lives in. ❓Which of these questions do you catch yourself using? — ♻️ Repost to help others ask better questions. ➕ Follow Nadeem for more leadership truth.

After working with 353 companies in the last ten years, we've found that it’s not too much conflict that kills teams. It’s the fear of having any at all. Disagreeing well is one of the most important—and most overlooked—skills we now teach for today’s workplace. We put so much emphasis on teams "connecting well" and feeling "safe and seen". But what about disagreeing well, challenging each other in a safe way. Time after time, we hear our clients say that their people stay silent in meetings, avoid giving feedback, or default to just saying “thank you” when what they really mean is “I disagree but don’t know how to say it.” Last week alone, we were on a discovery call with a client and I asked what the team lead wanted out of our potential workshop: “I really want them to learn how to disagree professionally.” That’s it. Not how to avoid conflict. Not how to sugarcoat it. Just how to do it well (as a mature adult), and challenge someone’s idea without actually making them feel like they’re being challenged. We invented a method three years ago called Inquisitive Empathy to help teams do just that. At the core of it is this idea: when in doubt, ask better questions. Not accusatory questions. Not questions loaded with hidden judgments. But curious, calibrated questions that start with What or How. Not Why. Questions like: “What outcome were you hoping for?” or “How do you see this working across teams?” These questions help people feel seen, not attacked. They create space for reflection instead of reaction. And they open the door for mutual understanding—even in moments of tension. When people learn how to disagree well, everything changes. Conversations go deeper. Ideas improve. Respect grows. And most importantly, people stop avoiding the hard stuff—and start leaning into it, together.