Mastering Questioning Skills

Ever feel like your conversations hit a wall—fast? You’re asking questions. You’re showing up. But all you’re getting are surface-level answers... or polite head nods. Here’s the truth: It’s not just what you ask.  It’s how you ask it. Strong leaders don’t need to have all the answers. They need to ask the right questions—the kind that spark clarity, ownership, trust, and growth. Here’s a quick breakdown that’ll level up your communication game ⬇️ 🔓 Open-Ended Questions Use when you want reflection, dialogue, and real insight. They unlock honesty, creativity, and connection. 💼 Leadership & Team • “What’s your perspective on how this project is going?” • “What do you feel about the direction we're heading?” • “What do you need from me to be successful right now?” • “How do you think we can improve our team dynamic?” 🔄 Feedback & Growth • “What part of that feedback surprised you the most?” • “What’s been working well for you—and why?” • “What would make this feedback more useful?” 🔍 Problem Solving • “What options have you considered so far?” • “What's the root cause, as you see it?” • “What would success look like in this situation?” 🤝 Coaching & Mentoring • “What’s holding you back right now?” • “What do you want to be known for in this role?” • “How can I support you without overstepping?” 🔐 Closed-Ended Questions Use for structure, speed, and decision-making. They bring focus, clarity, and momentum. ✅ Quick Check-ins • “Did you send the proposal?” • “Is the deadline still realistic?” 📊 Data & Decisions • “Do you agree with this plan?” • “Is that within our budget?” ⏱ Operational • “Has the issue been resolved?” • “Did the system go live on time?” 🎯 Pro Tip: Open-ended questions build trust and unlock real conversations. Closed-ended ones move things forward fast. Smart leadership is knowing when to use which—and why. Here’s the bottom line: Your questions shape your culture. They either open doors—or close them. Ask better, and you lead better. 👇 What’s one question that’s helped you unlock deeper conversations at work? ♻️ Share this with your network if it resonates. ☝️ And follow Stuart Andrews for more insights like this.

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

I've analyzed thousands of sales calls. One pattern separates top performers from everyone else: They ask "why" without saying "why." Here's what I mean: Bad AEs ask: "Why is that important?" (Feels interrogative. Puts buyers on defense.) Great AEs ask: - "What's driving you to prioritize that?" - "What's going on in the business that's making this urgent?" - "Help me understand what's behind that." Same intent. Different response. The word "why" triggers something in people. It feels like you're questioning their judgment. Like a parent asking a teenager: "Why did you do that?" But when you rephrase it? Magic happens. Here are 5 ways to ask "why" without saying "why": Instead of: "Why does that matter?" Try: "What's driving your timeline?" Instead of: "Why now?" Try: "What's the urgency behind solving this now versus later?" Instead of: "Why is that a problem?" Try: "What made this resonate?" Instead of: "Why do you need that?" Try: "What's going on in your world that's making you need that?" Instead of: "Why are you looking at this?" Try: "What motivated you to start exploring this?" Same information. Zero resistance. Start asking "why" without saying "why." Your discovery calls will never be the same. P.S. These 7 strategies will help you CLOSE more deals in a GTM crisis: https://lnkd.in/d_DkYTSH

If you are still asking "what are your biggest challenges?" on discovery calls, you are asking prospects to lie to you. I cringed watching a rep ask this on a recorded call. The prospect's body language changed instantly. Shoulders tensed. Tone shifted. Classic defense mode. His response? Generic corporate speak about "optimizing processes" and "driving efficiency." Translation: I don't trust you enough to tell you our real problems. This rep spent the next 30 minutes trying to extract pain points while the prospect gave him absolutely nothing useful. Deal died two weeks later. Here's the brutal truth about discovery. Prospects don't want to admit their problems to strangers trying to sell them something. It makes them feel vulnerable. Incompetent. Like they're painting a target on their back. So they lie. Not maliciously. Defensively. They give you sanitized, politically correct answers that reveal nothing about their actual pain. Meanwhile, their real challenges are keeping them up at night. Budget constraints. Team turnover. Missed deadlines. Political landmines. Systems that break constantly. But you'll never hear about those if you ask direct problem questions. So what actually works? Ask about situations, not problems. Ask about initiatives, not challenges. Ask about their boss's priorities, not their own frustrations. Here's my favorite discovery question that opens everything up. "Walk me through how you currently handle [specific process]." They'll describe their workflow step by step. And naturally... they'll mention what's broken. What takes too long. Who gets frustrated. Where things fall apart. But now they're not admitting problems. They're just explaining their world. Completely different psychology. The follow up that seals it? "How does your team feel about that process?" Suddenly they're telling you everything. Who complains. What breaks. Why leadership is frustrated. Internal politics. Resource constraints. All the real pain that drives buying decisions. Because you didn't ask them to admit problems. You asked them to explain situations. The best AEs don't interrogate prospects about pain points. They guide prospects to discover their own pain through natural conversation. And natural conversation reveals everything interrogation never will. P.S. If your reps are struggling with discovery, there's usually a deeper system problem underneath it. The free Revenue Leak Diagnostic Playbook shows you exactly where deals are dying on your team, how much it's costing you, and what to fix in the next 90 days. Built for CROs and sales leaders with 5-25 person teams. Grab it here:https://lnkd.in/gDexefD5

I hired a sales coach last month. First session, he asked to observe my discovery call. I was confident: - I had my 27 discovery questions ready - My demo was perfectly polished - My objection-handling guide was open The call started well. But 10 minutes in, the coach passed me a note: "STOP TALKING." I was confused, but I paused. The prospect filled the silence: "Actually, what I'm really struggling with is getting various stakeholders aligned. We keep having the same conversations over and over." This wasn't on my script. After the call, the coach explained: "Your discovery process is all about YOU getting information. Not about helping THEM discover their own problems." This hit me hard. I had been: - Asking questions to fill MY knowledge gaps - Taking notes to build MY sales strategy - Following MY playbook regardless of their responses The next discovery call, I tried something different: Instead of firing questions, I created a collaborative digital space where the prospect could: - Map out their own buying committee - Prioritize their challenges visually - Document their questions in real-time - Outline what success would look like to each stakeholder The call took half the time. The prospect did most of the talking. And they left with clarity they didn't have before. They signed 3 weeks later. What changed? Old discovery: Interrogation disguised as conversation New discovery: Collaborative problem-solving Your prospects don't need your questions. They need clarity. And often, they'll sell themselves if you just create the right space. Agree?

My team has stopped asking questions. They now wait for instructions. A leader shared this observation at last Thursday’s Melbourne Business School - Retail & Consumer Goods panel. It perfectly captured the curiosity crisis facing our industry in an uncertain operating environment. In a brilliant conversation with Adam Murphy 🌻 , moderated by Lenny Chudri, GAICD, we explored how to reignite innovation when uncertainty is our new normal. Here is what resonated most: 1. The 5-Question Rule That Changed Everything At a global FMCG giant, we were stuck. Innovation had become theatre, all talk, no breakthrough. So we tried something radical: “Curiosity Time”. Rule: For one hour every Friday, you could ONLY ask questions. No answers. No solutions. Just questions. The first session was painful. By week six? We had identified three breakthrough opportunities worth $5M. 🎯Try this tomorrow: Start your next meeting with 5 minutes of questions only. No answers allowed. 2. When Budget Cuts Forced Our Best Innovation Leading innovation at a major CPG company, I faced a 30% budget cut. Instead of scaling back, we asked: “What would we do if we had 10% of the budget?” That constraint forced us to partner with suppliers in ways we never imagined. We reduced a 12-18month innovation cycles to 3 months. The result? Our most successful launches that decade. Key insight: Every constraint hides an opportunity. 🎯 List your top 3 constraints right now. Pick one. Ask “How might this force us to be brilliant?” 3. The $8M Mistake That Taught Me Everything Years ago, I led a “perfect” innovation project. Great consumer research. Flawless execution. It failed spectacularly. Why? We had curiosity at the top but killed it everywhere else. Only 24% of employees feel curious at work, yet curiosity increases creativity by 34%. That gap is your innovation problem. At my next role: We measured “learning velocity” alongside EBIT. We celebrated fast failures publicly. We made questioning as important as delivering. 🎯 Your move: Ask your teams: “What are we pretending not to know?” Then actually listen. After commercialising 1,200+ innovations globally, from establishing industry-first research hubs, I know this: Curiosity is not a nice to have. It is your sustainable competitive advantage. Sharing this handy question. ❓If your biggest competitor had your constraints but twice your curiosity, what would they do differently? Some 📸 from an inspiring evening of #learning and #unlearning. Lenny Chudri, GAICD Adam Murphy 🌻 Innovation Gamechangers University of Melbourne Melbourne Business School #curiosity #innovation

How do you help your team members handle challenges—without taking on their challenges for them? 

In working through a challenge and learning from it, your team is able to grow. Think about the last time a team member told you about a challenge they had…and then somehow it was turned over to you to manage, or you picked it up and solved it.

You might be so good at putting out fires you didn’t even realize it. 

I get it. I’m an action-oriented person. I love to solve problems. I love to support my team.

A leader’s job is to coach team members to solve their problems and handle difficult situations, not necessarily do it for them. 

I definitely learned this the hard way as a new leader.

First, I drowned in directly managing the team’s challenges plus my own. Then, I learned my efforts to help my team unintentionally showed them that only I can handle something, or to expect that I will.

I still take seriously my role as a leader to remove barriers and intervene, as appropriate—but I also remind my team members that I believe in their abilities.

Here are three steps to help your team members navigate their own challenges (with your support and guidance, of course). ASK QUESTIONS Ask your team member open-ended questions to help them think through the challenge. You might say, “What do you think the next step should be?” or “How should we handle this challenge?” You want to draw out their perspective and demonstrate that this is something you expect them to manage. DETERMINE YOUR ROLE When your team member starts talking about their challenge, try to determine if they need to vent or need you to do something. Because I have a tendency to jump into things, I have to catch myself to ask if the team member wants feedback, support, or action. If they want feedback or support,they’re showing they intend to manage through the challenge and would benefit from your guidance. If they request action, dig a little deeper before you take this on. Try to understand if they aren't confident in their choices and need reassurance, or if they're delegating the tough stuff to avoid managing it themselves. REINFORCE YOUR TEAM MEMBER’S STRENGTHS Acknowledge your team member’s challenge—and their ability to get through it. Reassure them that you believe they can handle it. You may remind them of how they successfully handled a difficult situation in the past. Most importantly, remember that the leader’s role is not to solve their team's problems—but to help their team become better problem solvers.

Most sales managers ask the wrong question after a lost deal. They ask "What happened?" Great leaders ask "What would you do differently?" See the difference, ya'll? One creates defensiveness. The other creates learning. THE INTERROGATION TRAP "What happened?" sounds innocent. But here's what your rep hears: "Justify your failure." "Defend your choices." "Explain why you screwed up." So they get defensive. They blame the prospect. They blame marketing. They blame timing. Meanwhile, you're trying to coach but you're accidentally putting them on trial. THE DEVELOPMENT QUESTION "What would you do differently?" Same conversation. Completely different energy. This question assumes they learned something. It focuses on the future, not the past. It makes them the expert on their own improvement. Watch what happens: "I'd ask about budget earlier." "I'd multi-thread from the start." "I'd slow down in discovery instead of rushing to demo." Now you're coaching forward, not backward. WHY IT WORKS When you ask "What would you do differently?" three things happen: They own the lesson instead of defending the loss. They design their own development plan. They feel trusted, not interrogated. And here's the kicker - they're way harder on themselves than you'd ever be. THE CULTURE SHIFT Teams that ask "What would you do differently?" build learning cultures. Teams that ask "What happened?" build blame cultures. In learning cultures, reps bring you losses to discuss. In blame cultures, they hide problems until they explode. Which would you rather manage? FRAMEWORK FOR LEADERS After any loss, try this sequence: "What would you do differently?" (Let them talk) "What do you think caused that?" (Help them dig deeper) "How can we practice that?" (Make it actionable) "When will you try it?" (Create accountability) THE COMPOUND EFFECT Do this consistently and something magical happens. Your reps start asking themselves "What would I do differently?" before you even get to the debrief. They become self-coaching machines. That's when you stop being a manager and start being a multiplier. It's not complicated. It's just different. One question. Completely different culture.

🎯 Master the Art of Internal Audit Interviews: A Guide for New Auditors After years in internal audit, I've learned that the key to uncovering meaningful insights isn't just the numbers - it's how you conduct interviews. Here's my survival guide to conducting effective audit interviews: 1. The Power of Preparation: - Research the department's processes before the interview - Review prior audit reports and known issues - Prepare a structured question list but stay flexible - Understand the interviewee's role and responsibilities - Pro tip: Keep a water bottle handy - it's amazing how often "taking a sip" saves you from awkward silences 2. Interview Psychology 101: - Start with easy, factual questions to build rapport - Use the "funnel technique": broad questions first, then drill down - Pay attention to non-verbal cues - they often tell the real story 3. Question Techniques That Get Results: - "Walk me through..." - Gets detailed process explanations - "What happens when..." - Reveals exception handling - "How do you ensure..." - Uncovers control mechanisms - "Can you show me..." - Verifies actual vs. described procedures 4. Active Listening Tips: - Take brief notes but maintain eye contact - Pause after responses (silence often prompts additional details) - Summarize key points to confirm understanding - Listen for inconsistencies with documented procedures 5. Common Pitfalls to Avoid: - Don't interrupt or rush responses - Never make assumptions or judgmental comments - Avoid leading questions that suggest answers - Don't fill silent moments with unnecessary talk Remember: The best auditors aren't just good at finding issues - they're excellent at getting people to share information willingly. What interview techniques have worked well in your audit experience? Let's share knowledge! #InternalAudit #AuditTips #IA #Auditing #RiskManagement #Leadership

Given my role as an Organisational Psychologist, I've spent a LOT of time over the past decade thinking about #PsychologicalSafety – perhaps not surprising given the "psychological" part of being a psychologist! 🤣 In my view, one of the simplest ways for leaders to encourage open dialogue – both a signal of and a contributor to psychological safety – is to… ASK BETTER QUESTIONS. Let's take the example of a leader sharing a plan, strategy, idea, or proposed approach with the team / organisation. Instead of asking... 👉 “Any questions?” (cue awkward silence) Try something like... 💡"What could I be missing or not seeing?" 💡"What’s something you’d do differently if you were in my shoes?" 💡"Right now, what feels most unclear or uncertain?" 💡"Where could we be oversimplifying or overcomplicating things?" 💡"What other angles need to be considered?" Why does this work? Because these questions make it easier – and more comfortable – for people to speak up. They actively invite contributions, and show that, as a leader, you know you might be missing something. They show that you value others' input. In psychological safety terms: they "invite participation" and "demonstrate situational humility". Of course, how you respond to those contributions also matters – but that's a post for another day. 📑 Save or share this post if you think these questions might come in handy! 👇 And please share – what's one question you'd add to this list?