How to Ask the Right Questions

🤔 One of the skills I've worked hardest to improve is asking better questions. Here are 7 tips I've learned to ask powerful questions: 1️⃣ Ask one question at a time Don't spray questions like shotgun pellets. If you ask 3-4 questions in a row, people will forget them. Ask one -> Get an answer -> Ask the next. 2️⃣ Opt for shorter questions Asking long questions is often as bad as asking multiple questions. Long questions confuse people. It takes a surprising amount of confidence to ask short, simple questions. 3️⃣ Become comfortable with silence If you ask a good question, you should expect some silence. Silence is the noise thinking makes. Leave space for it. 4️⃣ Ask open-ended questions You'll get way better information if you avoid simple yes/no questions. They're often too limiting. For example, asking your boss “How do you think I’ve been performing lately?” is fundamentally different than “Do you think I’ve been performing well?” 5️⃣ Avoid “Why” questions Questions that begin with “why” tend to make presumptions or assume the worst (e.g., “Why did you…”). They put people on the defensive. You want to invite someone into a discussion with you — not shut down the conversation with a question that prompts defensiveness. 6️⃣ Ask “What” and “How” questions Questions that start with “What” or “How” invite the other person to share their ideas (without any presumptions). The biggest difference you can make in your questions is to substitute "What" and "How" questions for "Why" or yes/no questions. 7️⃣ Don’t hide answers in your questions Questions like “Why wouldn’t we just [take this course of action]?” are what author Michael Bungay Stanier calls “offering advice with a question mark attached,” and it’s a subtle form of manipulation. Ask legitimate questions — not contrived ones. Thanks to friends and mentors like James Pratt, Harry Gefre, Brittany Blumenthal, and Bobby Moran for teaching me how to ask better questions!

Why you should be more like Socrates 📚 Have you heard of Socrates? One of the most recognized names in modern thinking is famously quoted as saying, “An unexamined life is not worth living.” Today, as aspiring advisors to our customers, it’s important to understand that… Our unexamined questions are not worth asking. ❓ Why? It is not designed for what we want most - to get us closer to the TRUTH. As the good book says - the truth shall make you free. Free from: Assumption and poor judgment Low-converting customer conversations Unrealized and inconsistent results Lack of connection with customers 🔬 I believe the purpose of questions is to bridge the unknown to the known and the known to positively known for you and your customers… What does that mean? It’s about bringing what is true to the surface and validating that it is certainly true. This is critically important today as language changes, business focus shifts, and we interact globally. All people have a particular way in which they interpret the world. Even when we share the same language, we may still have differences in our definitions. 🏎 Example: If you were to ask someone to think about an expensive car, you might think of a Ferrari, but they might think of a Mercedes. This difference in thinking can be called a ‘model or framework of thinking.’ In order to truly understand what a person is thinking and what they mean from their words, you must first be able to determine how the other person defines those terms. You must be inquisitive and deductive at the same time. It wasn’t until a few years ago when I was coaching a group of high-performing reps, that I realized how important this was. I heard them have customer conversations, struggle to move them forward, get engagement a week later, or have a client disagree with their interpretation of a meeting. In view of this, I taught them a new framework of questioning inspired by Socratic thinking. J-cratic rules: Every conversation... Must have a purpose Carry a FRAME or multiple FRAMES Must be guided by the pursuit of truth 🤓 J-cratic questions 1. CLARIFY - Questions that help understand the meanings of certain phrases, terms, or facts. ex: Could you help me understand what you mean by X? 2. CHALLENGE - Questions that help customers think more critically about what they want on a deeper level (think about the why in the golden circle) ex: How did you come to a conclusion about doing Y? 3. EXAMINE - Questions that help customers focus on what matters most. Focus on implicative decisions. ex: What would be the impact of doing X vs Y on your business/department/result? 4. EXPLORE - Questions that help customers commit to looking at the best options to take action. ex: Considering all we’ve gone through today, what are your thoughts on ‘actions 1, 2, & 3? What struck you? Share in the comments.👇🏽 P.S. [cratic in Latin means source/authority - hence J-Cratic 🙂] #customeradvantage #customergrowth

Sellers, do you ask more than one question at a time? Rapid firing questions is one of the worst things you can do in discovery, why? 1. Your client can't answer multiple questions at once, so they pick the last thing they heard and skip the rest - you just lost valuable information 2. It makes their head explode and feel overwhelmed, so you are emotionally triggering them and causing anxiety 3. You appear nervous and disorganized because you aren't focused 4. It doesn't give you space to dive deep into anything because you are just getting answers and rapidly firing to the next thing, which is the biggest mistake in all of discovery. Deep answers are better than lots of answers. Now look, I get why you are doing it. You are excited, you have a lot to figure out. You want to know all the things. This is good. But you need to control this energy. Here's how: 1. Write down your questions BEFORE the meeting so they aren't in your head 2. Take notes during the call and write unanswered thoughts down to circle back to 3. See bullets one and two...do this :) If you have this issue and don't solve it, you are leaving a tremendous amount of money on the table and losing winnable opportunities to help people, because you are missing the valuable depth of information and trust that is built by thoughtful conversation. If you are struggling with this skill, next time, prep for the call, write your questions down, and just ask ONE. Dig into those answers, write more questions based on those answers on your sheet of paper, and slowly go through everything. I promise your discovery will be transformed overnight.

I believe that asking good questions is the most powerful tool in a lawyer's business development toolkit. And the most effective type of question is an open-ended one. The beauty of open-ended questions is that they unlock doors to deeper understanding. Unlike close-ended questions that often elicit mere facts, open-ended inquiries invite clients to share their challenges, aspirations, and concerns. By posing questions such as "What challenges are you currently facing?" or "What is your primary objective in this case?", you can unearth different layers of a prospective client's situation, allowing you to engage in meaningful dialogue. However, as this dialogue unfolds, it's essential not to remain a passive listener. Weaving in insights that reflect your expertise demonstrates curiosity, interest and creates a space where clients feel both heard and enlightened. Saying something along the lines of “That makes sense. I’ve dealt with clients in similar situations and here’s how we approached that problem…” can go a long way toward building confidence that you’re the right lawyer for the job. In my experience, too many lawyers spend an inordinate amount of time preparing answers to questions they expect to be asked during a business development conversation. A better use of time is to come armed with lots of thought-provoking, open-ended questions of your own.

I had this boss who would always tell me: ”Walker, you just gotta ask the right questions!” I would go on sales calls with him. I would pay attention. But I never picked up which were the “right” questions. I’d see him asking about the pictures on their desk, the fish on the wall or what they thought about the game last weekend – so I used to do that too, thinking these must be what he means by the “right” questions. After asking those “right” questions, I’d watch him jump into a pitch about why the prospect should move their relationship to us. Then he’d watch me on a sales call and after, he’d say, “No, you didn’t ask the right questions.” Finally, one day I asked him, “What in the hell are the right questions?” He looked at me and shook his head, said, “You’d know if you had been paying attention.” And then it hit me… I needed to get out of there! It took me 10 years to figure this out, but here’s the answer to “what are the right questions?”: That’s the wrong question! What we need to figure out is what are our prospect’s opinions about their current situation and what, if anything, they’d be committed to fix. That should be your focus. So if you want one “right” question then here it is: Would they be a good prospect for me? To know that, you’ll need answers to the following: Do they have a personal compelling reason to change? Do they have the resources (money, time, people) to make the change? Does their decision making process give you an advantage? Be genuinely curious about the person in front of you to see if they’re ready for a solution like yours. That’s when you’ll start asking the right questions.

Life and Leadership Lessons: Showing genuine interest I have always found the words “How are you?” fascinating. In our day-to-day lexicon, these words have become a form of greeting. And we are attuned to respond using just a few words: “Fine! And you?” That second question is usually not responded to, and a conversation ensues – or doesn’t. Now, if you are really interested in finding out how a person is, how do you ask the question so that you elicit that information? Do you say, “How are you doing?” or “Seriously, how are you?” I have discovered that the best way to do this is to escalate the questions gently. "How are you?" "I’m fine, thanks." "No, really, how are you? "Well, it’s been a tough day but it's all good, otherwise." “I sense something. How ARE you?” And then the true story comes out. This technique of asking the question three times with slight modifications is also really effective when interviewing candidates. The ability to persistently ask the same question should not be viewed as being prosecutorial, but simply as showing a genuine interest in the individual. If your intent is to be prosecutorial, the other party will sense it and immediately freeze. Therefore, if you ask this question in a manner where you are seeking to hurt this individual, there’s a high probability that you will be unsuccessful. If your intent is to genuinely understand and/or show your interest, the other party will respond accordingly. Go ahead and experiment; it’s a lot of fun. #lifeandleadershiplessons #theartofquestioning #interest

One of the best lessons I learned as a young attorney: ask questions, especially "stupid" ones. While working as an new associate attorney at a large firm, I was often pulled into client meetings with partners. I appreciated the opportunity to meet clients and see the practical application of the abstract legal concepts I was researching and writing about behind the scenes. One particular meeting with a partner and his client still stands out in my memory. He was a very successful corporate attorney at the firm; smart and experienced. As the client started talking through the facts of their situation, this attorney would often stop and ask what seemed to me as pretty basic questions, confirming what he was hearing. Or he would ask a question one way, then ask it in slightly a different way again. There were even times where it seemed like he was asking the exact same question that he had asked earlier in the conversation. By the end of this 90-minute meeting I started to see the point of his questioning. The apparent redundancy fleshed out information and absolutely confirmed that his understanding of the matter was consistent with his clients, and vice versa. Sometimes the client's response was also different than I expected based off their previous answers. What seemed like tedious and even elementary questions to a new attorney turned out to be disciplined, purposeful, and intelligent ones. This experience started to knock down the fear I felt of asking questions that seemed too simple or might show that I didn't understand. In any profession (especially law practice) effective communication is a key ingredient of success. Whether you're an attorney meeting with a potential client, an employer interviewing an employee (or vice versa), or a sales representative seeking to understand a client's business, questions are a powerful tool. Rather than fear asking a "stupid question," appreciate the opportunity to really have a meeting of the minds. Truly communicating with whomever you're meeting with is so much more important than looking smart. #idahome #leadership #askquestions

Want to be an effective leader? Ask more questions. Then, listen more than you talk.   This might seem counter-intuitive, especially coming from a person who works in the public speaking realm. But it’s actually the biggest mistake I see people make when working on an important piece of communication.   In my 30+ year career as a communication consultant, I’ve helped hundreds of executives get ready for their big moment in the spotlight.   They usually come into our first session full of ideas… “I was thinking I should talk about A and B, maybe a bit on M and N… Oh, and I also need to tell them about the new GHI thing. That’s really important!”   The exec is getting super fired-up about their content by this point. So, what I say next probably feels like getting hit with a bucket of ice-cold water.   “Great! I want to hear all about your ideas,” I’ll tell them. “But first, let’s talk about something equally important: your audience. What do they think about your topic? And how do they feel about you?”   Silence. Maybe a bit of hemming and hawing. “Well, hmm. I’m not sure,” many people say.   That’s because more often than not, speakers spend all their prep time (if they do any prep at all) thinking about their content, instead of thinking about their audience. And then they wonder why the message didn’t land well or didn’t get the results they wanted. If they’d only shown some curiosity about their audience, the speaker would have learned what to say to actually win them over.   So, here’s the secret to being a truly great leader: be a student of people.   Get out and talk to your constituents – whether that’s your employees, customers, partners, whomever. Ask questions about their daily struggles and their future goals, about the things that excite them and worry them, and what they’re hoping you’ll solve for them.   Then use those insights to re-craft your messages to speak directly to the hopes, fears, and needs of your audience. By approaching communication as a two-way street – putting equal energy into both listening and speaking – you’ll be more likely to influence others to support your ideas.   That’s what I think, anyway. What do you think makes for more effective communication? Drop it in the comments! #communicationstrategy #publicspeaking #influence #empathyinaction

❓Ask the question❓ As a neurodivergent legal professional, I always have questions. I have to be able to see and understand the full picture to wrap my head around something. I've been that way my entire life (just ask my parents). But I spent the first half of my legal career sitting silent in meetings. I had questions, of course. But I never asked them. In one job, this was absolutely the expectation - needless to say, it was a job I should have left sooner. But in my other early career roles, I let my own misconceptions keep me from speaking up: 1️⃣ Smart people don't ask questions. This one is patently false. Yes, I've worked with people who think this way. But the smartest people I've had the chance to work with are the ones asking the questions. Curious people are the smart ones - not those that simply pretend to know everything. 2️⃣ I had no place speaking up in a room full of senior leaders. I can be intimidating to speak up in a room where others are much more senior to you. But if you're in that room (in-person or virtually), you should be there for a reason. You were invited because you have value to add to the discussion, so do what you are there to do. ❓ So, ask the question.❓ ✨ Ask the question to clarify something you don't fully understand. Chances are someone else is in the same boat. ✨ Ask the question to identify gaps and possible pitfalls. If you don't, there is a chance no one else will. ✨ Ask as many questions as you need to ask to get the answers you need to do your work. That's what you're there for. #inhouselegal #legalprofessional #legalcommunity #tipstomyformerself

This Question transformed our Business….. In 2020, my team and I embarked on a journey to scale DVS, but we hit roadblocks. We really didn't know how to scale up a Professional Services enterprise as an Institution. Our peers from the industry were either partnerships or associations or networks which wasn't our vision. It wasn't until I traveled to the heart of capitalism, the U.S., to study the growth of service firms, that I had an epiphany. I had been fixated on finding direct answers to our scaling challenges. However, I realized I was asking the wrong questions. Instead of "How do I scale up?", I should have been asking, "Who can help me scale up?" This shift in focus was transformative. By seeking individuals with the right expertise and giving them the necessary resources, we altered our course. After learning the @scalingup philosophy of Verne Harnish , we implemented these insights DVS Advisory Group The impact? It was monumental. Our business was never the same again. This journey taught me a vital lesson: It's not always about the answers we seek, but the questions we ask. Asking the right questions can unlock potential and pathways we never thought possible. It's a strategy not just for business, but for life. From then on whenever we are faced with a situation we are either clueless or do not have the capability to solve - I spend a lot of time and energy to articulate the right questions- and identifying the right people to ask these questions either for validation or refinement. The journey to seek answers only begins post this exercise. Friends this approach has radically transformed our quality of existence and made our journey so much more purposeful and defined. Are you asking the right questions in your journey? Share your experiences or thoughts below.