Tips for Asking Insightful Questions in CEO Meetings

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.

During a high stress moment of frustration, a CEO harshly told one of my students: “I need you to be a thought partner, not another task manager!” She swallowed the lump in her throat as she exited the video call, but... she knew he had a point. 😕 She’d been burning herself out checking boxes, clearing tasks, reacting to requests. And, in doing so, she was unintentionally making herself smaller (and less effective). The difference between a support person (tactical/ a task manager) and a Chief of Staff (strategic/ a thought partner) is about 𝗵𝗼𝘄 𝘆𝗼𝘂 𝘁𝗵𝗶𝗻𝗸, 𝗻𝗼𝘁 𝘄𝗵𝗮𝘁 𝘆𝗼𝘂 𝗱𝗼. ➡️ So she made a shift, 𝘰𝘯𝘦 𝘵𝘩𝘢𝘵 𝘢𝘯𝘺 𝘤𝘶𝘳𝘳𝘦𝘯𝘵 𝘰𝘳 𝘢𝘴𝘱𝘪𝘳𝘪𝘯𝘨 𝘊𝘩𝘪𝘦𝘧 𝘰𝘧 𝘚𝘵𝘢𝘧𝘧 𝘤𝘢𝘯 𝘮𝘢𝘬𝘦, and started operating like  a true thought partner. Here’s how that’s done: 1️⃣ 𝗦𝗵𝗲 𝘀𝘁𝗼𝗽𝗽𝗲𝗱 𝘄𝗮𝗶𝘁𝗶𝗻𝗴 𝗳𝗼𝗿 𝗶𝗻𝘀𝘁𝗿𝘂𝗰𝘁𝗶𝗼𝗻𝘀. Instead of asking, “What do you need me to do?” she started showing up with recommendations (bringing solutions to the agenda, not just problems) 𝗛𝗢𝗪 𝗬𝗢𝗨 𝗖𝗔𝗡 𝗗𝗢 𝗧𝗛𝗜𝗦 𝗧𝗢𝗗𝗔𝗬:  when you become aware of or identify a problem or issue that needs a decision, 𝗱𝗼𝗻’𝘁 𝗷𝘂𝘀𝘁 𝗶𝗻𝗳𝗼𝗿𝗺 𝘆𝗼𝘂𝗿 𝗯𝗼𝘀𝘀 𝗼𝗳 𝘁𝗵𝗲 𝗶𝘀𝘀𝘂𝗲, 𝗶𝗻𝗳𝗼𝗿𝗺 𝘁𝗵𝗲𝗺 𝗼𝗳 𝟮-𝟯 𝘀𝗼𝗹𝘂𝘁𝗶𝗼𝗻𝘀 𝘆𝗼𝘂’𝘃𝗲 𝗮𝗹𝘀𝗼 𝗶𝗱𝗲𝗻𝘁𝗶𝗳𝗶𝗲𝗱 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿 𝗿𝗲𝗰𝗼𝗺𝗺𝗲𝗻𝗱𝗮𝘁𝗶𝗼𝗻𝘀 𝗳𝗼𝗿 𝘁𝗵𝗲 𝗯𝗲𝘀𝘁 𝗼𝗻𝗲 𝘁𝗼 𝗰𝗵𝗼𝗼𝘀𝗲. 2️⃣ 𝗦𝗵𝗲 𝘀𝘁𝗮𝗿𝘁𝗲𝗱 𝗳𝗿𝗮𝗺𝗶𝗻𝗴 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀 𝗮𝗿𝗼𝘂𝗻𝗱 𝗽𝗿𝗶𝗼𝗿𝗶𝘁𝗶𝗲𝘀, 𝗻𝗼𝘁 𝘁𝗮𝘀𝗸𝘀. When her CEO asked for updates, she didn’t just list what she’d done, she explained how it moved their org-wide goals forward. 𝗛𝗢𝗪 𝗬𝗢𝗨 𝗖𝗔𝗡 𝗗𝗢 𝗧𝗛𝗜𝗦 𝗧𝗢𝗗𝗔𝗬:  Before every task or project you work on, ask yourself, “How is what I’m doing helping us win long-term?” Then document that so you have proof of your impact. 3️⃣ She built the habit of challenging upward. This one felt scary at first, but she learned to respectfully push back and ask her CEO tough questions like: 🤔 “What tradeoff are we making if we choose this option?” 🤔 “How will this decision impact the team next quarter?” 🤔 “Is this the best use of your time right now?” Her boss…? He loved it!! 𝗧𝗛𝗜𝗦 𝗶𝘀 𝘁𝗵𝗲 𝘁𝘆𝗽𝗲 𝗼𝗳 𝘀𝘂𝗽𝗽𝗼𝗿𝘁 𝗹𝗲𝗮𝗱𝗲𝗿𝘀 𝗻𝗲𝗲𝗱 𝗳𝗿𝗼𝗺 𝘁𝗵𝗲𝗶𝗿 𝗖𝗵𝗶𝗲𝗳 𝗼𝗳 𝗦𝘁𝗮𝗳𝗳. It will work for you too. Start thinking like the person in the room who’s helping make the decisions, not just carry them out.

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