How to Use Asking Skills in Business Communication

“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.

Stop nodding along in meetings. Start having impact: Too often, meetings are filled with phrases like: ❌ “That sounds great” ❌ “Let’s table it for another time” ❌ “Let’s circle back when we have more info” From 10 years in high performing teams, here’s what I’ve learnt about meetings: Top performers aren’t afraid to ask the hard questions. Here are 13 questions you can ask to leave a mark: 1/ "What do we have to deprioritize to do this well?" ↳ Use to help create focus. ↳ Shows you understand we can't do everything at once. 2/ "What happens if we do nothing?" ↳ Use to overcome inertia. ↳ Helps identify true priorities. 3/ "Who's done this well that we could learn from?" ↳ Use when projects have been done before. ↳ Shows you want to use others’ learnings. 4/ "What's the simplest way to explain this?" ↳ Use to create clarity. ↳ Shows you understand the importance of simplicity. 5/ "What went wrong last time?" ↳ Use when repeating past initiatives. ↳ Shows you want to learn from experience. 6/ "How will we know if this is working?" ↳ Use when success isn't clearly defined. ↳ Shows you care about real results. 7/ "Who's going to own each workstream?" ↳ Use when responsibilities are unclear. ↳ Prevents the "someone else will do it" problem. 8/ "How does this affect our current priorities?" ↳ Use when new work might disrupt current priorities. ↳ Shows you're thinking about the whole picture. 9/ "Who might we upset by this choice?" ↳ Use when changes could impact others. ↳ Shows you consider how others might feel. 10/ "If we had half the budget, how would we do this?" ↳ Use to find creative solutions. ↳ Shows you can spark new ideas. 11/ "What aren't we seeing here?" ↳ Use when consensus comes too easily. ↳ Shows you look at problems from all angles. 12/ "How does this help us reach our primary goals?" ↳ Use when projects drift from objectives. ↳ Makes sure we're not getting sidetracked. 13/ "What's our plan for the worst-case scenario?" ↳ Use when planning risky initiatives. ↳ Shows you think ahead. Remember: Impact can from asking the right questions. You don't have to be the smartest one in the room. Just ask the questions that make others think differently. P.S. Which of these will you use in your next meeting? — ♻ Repost to inspire your network to have more impact at work. ➕ Follow me (Will McTighe) for more like this.

🔥 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.

This clarifying question has CONSISTENTLY gotten me more valuable information from prospects. It’s so basic I wish I’d started using it sooner… Whenever someone tells me something they want or need that is remotely up for interpretation, I ask: “What does *that* mean/look like, to you?” Examples: CEO: “My number one problem is discoverability.” Me: “What does discoverability mean, to you?” CEO: “I want more people to know about us. I want my company to be the first thing people think of when they’re evaluating our category.” VP of Sales: “We need more pipeline coverage.” Me: “What does more pipeline coverage look like, to you?” VP: “We’re at a 2.5X multiple right now. We need to be at 5X to hit our revenue targets.” This question is effectively “mirroring” my prospect, but (to me) feels less manipulative. It also helps me: 1) further quantify the business impact, and 2) build more trust through understanding Try it on your next disco call. #sales #discovery #salestips