Ep 38. The Art of the Question: Why the Right Questions Matter More Than the Right Answers

[00:00:43] Hi Sean, welcome to the show.

[00:00:48] Very nice to be here, Kari. Thanks for the invitation.

[00:00:51] I have been looking forward to speaking with you for months. I got a hand on your book, I think before the holidays and started diving into it, and I’m just so excited to dive into the topic of asking good questions today. So before we dive in, I would love for you to just share a little bit more about you, where you’re from, what you do, just to give everybody a bit of context.

[00:01:18] Sure. Well, I’m Sean Grace and I’m a leadership consultant coach. I have two companies that I work within and under. One is Grace Media Works, which is more centered on multimedia production and the other one is called Peak Luma which is specifically about leadership, leadership development, professional development, and learning and development. So I’ve been doing this for many years now, but I come from the media industry in New York, where I worked in advertising and marketing, in magazines, and then eventually television and film. A lot of my background is on the media side. Also managing large teams, creative teams, as well as sales teams, business development teams. So over the many years, I developed a lot of different strategies, techniques and methodologies for managing high performance teams. It’s also sort of evaluating strategic challenges within different companies that I work for. Then I started doing more of this consulting work, which bloomed into a full time. And that’s when I started launching more professional workshops. One of the workshops I launched about five years ago is called The Art of the Question. I got tremendous feedback from that series. Excuse me. After a few hundred different participants flowed through the workshops over a couple of years I had developed enough content that I thought, Hey, there’s probably at least at least a book here. But of course, wrestling all that content into something that’s tangible and readable and accessible was a whole other challenge altogether because I’ve never written a book before. But it was quite quite fulfilling in the end. You know, it took about a year to actually write the book and it came out a few months ago. So I’m happy with the results and the feedback has been quite good and I continue with my consulting, working with professionals around the world, especially in the U. S, on helping them build a successful company, successful teams and especially high performance critically thinking teams as well as create a collaboration team. So that’s kind of what I do and where I come from. I’m also a musician and I do work semi professionally in live performance and recordings as well, so I have that as well. That’s I’ve always kept that as part of my life ever since I was young.

[00:03:41] So fun. What drew you to questions? I mean, you know, you’re, you’re going along, you’re in your consultancy business, and then what made you dive into the topic of questioning and asking good questions?

[00:03:59] Well, very early on in my business career, I learned that questions were a powerful tool to help solve problems and uncover issues as well as empower the teams that were working under me. Very early on as a young manager, I felt my job was to interject my experience and my supposed wisdom and solve problems for my various team members. That seemed to work just fine. But after a while, I realized, hey, maybe I’m not really building up the critical thinking skills of my teams and maybe me stepping in as the person that they’re constantly turning to for answers that’s not what I’m here for. I’m here to elevate them and, and have them build their own skills, when it comes to evaluating problems and analyzing potential solutions. I started using questions more strategically with my teams. And a lot of these teams are also sales oriented and you know, successful sales is very much built upon good questioning which is also about problem solving. It’s also about uncovering needs and that’s all through good questioning. So over the years, I began to really respect the power of questioning within business. This then poured over into my interpersonal communications, and I realized that questions also have a very powerful role in maintaining positive relationships, being able to be a good partner, being able to be a good friendship, all that kind of stuff was important to ask questions as opposed to just constantly doling out answers and prescriptions. When I started the workshop series, I had other communication style workshops, and within that I would incorporate an aspect of questioning. Those aspects were very interesting to my participants and they wanted to know more about this mysterious art form called questioning. So I started to thread more and more of the question aspect from a strategic standpoint and from a methodological standpoint into the various other workshops on communication until I realized that this really deserves. It’s own dedicated workshop. So that’s when it kind of coalesced into the art of the question. But it was really accumulation of decades of experience working with with teams also on the creative side, working with musicians and artists and other people in trying to come up with creative ideas, questioning, was also an important aspect of that. So all of that background experience, in addition to the more intentional effort on my part to put it within a curriculum and format really led to the book, led to the concepts and that’s sort of how it all came about. It’s really a lifetime of questioning and then, and then realizing that, wow, this is actually an important tool that a lot of people may not understand its power and may just take it for granted.

[00:07:07] Yeah, I love that this has just been years and years of organic, you know, putting the pieces together and forming the methodology, so I cannot wait to dive in with you. Let’s back up a little bit. In your book you talk about the history a little bit because it’s so helpful for us to get a context. So where have we as humans learned our core communication methods from and why does that matter?

[00:07:58] The philosophers of Socrates and Plato and Aristotle, especially Socrates in the beginning who said, Hey you know, questions are very powerful instruments, and let’s figure out ways to formalize their use, and from a standpoint of reasoning and logic. Socrates started to teach using a specific type of method, which we now call the Socratic method which had to do with not always necessarily looking for answers, but using questions as a catalyst for critical thinking. So he would have his students assembled and instead of saying, okay, here’s knowledge and here’s the knowledge I’m going to pass on to you, this is how we understand the world around us, this is how we understand truth and forcing his students to think first and not necessarily assume that there is necessarily one answer. Or that there’s just an answer to be memorized.

[00:08:57] So Socrates considered himself what he called a my eutic, which is Greek for midwife. And that concept has to do with recognizing that wisdom and understanding of the world to a large degree is accessible. And a lot of it is within us, but we have to give birth to our own understanding of things as opposed to being fed answers and fed reasons. Although there’s times for that and there’s purpose and value in that, what’s more important is fully understanding how something is, why something is, and that requires a critical thinking process which is really about coming to terms with understanding what something is. So Socrates wouldn’t stand there and say, okay, here’s abject reality. Here is abstract reality. He would question to have them come to understand the concepts. So he sort of birthed this concept of systems thinking and not just seeking. Because often there aren’t just a singular answer to things unless it’s, you know, solid truth in the melting temperature of lead or something. Besides that, you know, there’s a lot of different interpretations of what reality is, what reason is, what logic is, what truth is. So he felt that questioning was a very special tool that we were able to access and learn to use in order to become wiser.

[00:10:25] So Plato took that over and then eventually Aristotle took it over and he created the scientific method based on the same type of logical inference and sort of that type of logical reasoning both inductive and deductive reasoning through the process of questioning in order to come to some reasonable level of what is real, which eventually turned into the scientific method, which we all use today. So I think that those three main philosophers laid the foundation for how we continue to ask questions and continue to understand how questions play a role in how we understand the world. That’s at least my view on their role from a foundational standpoint, if that makes any sense.

[00:11:16] Yeah, I actually loved the summary because, you know, we as business coaches, we use questions all day long. One of the processes that I use with my clients is based off of the scientific method, right? I just think it’s so fun to look back and to see where some of these tools come from. They are ancient. And they work so well and we tap into them. One of the things that you say in the book is that, you know, the average toddler asks like hundreds and hundreds of questions per day. I forget how many it is.

[00:11:53] 350.

[00:11:57] And then as adults, we, you know, ask just a couple of questions a day, or we’re not even aware that, you know, a question might be the, the right avenue to go down. So how does that happen? Or why does that happen?

[00:12:10] Well, there’s a bunch of different theories around that. One of them has to do with the fact that as we come out of our young childhood, say, 4 year old period, where we are anxiously absorbing the world around us and are just naturally curious about the world. You know, we start to get answers to things. There’s a point where we kind of know enough, maybe by the time we’re 12 or 11 or 10, that our our incessant question asking that may have happened as a four year old asking several hundred questions a day is what is this? Why is this? How is this? Where is this? That just becomes less necessary. That’s one aspect of it. The second aspect of it is the socialization that happens in adolescence, where curiosity from an intellectual standpoint can become riskier as you begin to navigate your position within your peer group. So what happens is that you become much more self conscious about your knowledge level and how you appear to others. So, you know, raising your hand as a five year old or seven year old in elementary school is much less risky than raising your hand as a 14 or 15 year old in middle school or high school, where not knowing an answer may reflect poorly on your status within your peer group. Or maybe having too much knowledge can also appear as threatening to your peer group.

[00:13:48] So what happens is that I mean, just this is natural biology is that as we reach that adolescence and the pubescent period, our interests do shift to making sure that we maintain status within our social group, and that often has to do with calling back our curiosity, trying to fit in. Whereas four and five year olds aren’t trying to fit in, you know, they’re the center of their universe and their deep curiosity is incessant. You know, they, they can’t help themselves.

[00:14:23] Now the anxiety of adolescence does unfortunately carry into the business world where by the time you get out of college and now you’re working in a job, it’s often answers that are valued and not knowing an answer to a question or a problem you know, may look poorly upon you. So you carry that anxiety along with you because you become very self conscious of how it looks, if I ask. The wrong question or if I ask a question that’s a little off beat, you know, so that self consciousness really tamps down, continues to tamp down our curiosity or a willingness to be curious. I think those aspects have a big role and the diminution of our willingness or, or, or wanting to continue to ask questions.

[00:15:14] However, that’s not with everybody. Some people continue to maintain that what I consider sort of childlike curiosity. Constantly you know, being interested in things and being able to ask lots of questions and not be self conscious about that. So there are those, but they’re the exception. So I think that’s what probably happens with the decline in what I’ll consider our question asking, which reflects our curiosity. We also, to a large degree, become less curious because we become overwhelmed with living and just getting by and doing the things that we need to do that are the insatiable sense of curiosity that we have as a child, unfortunately, fades. Even though it’s still within us, though, I do believe and there are ways to bring it out. But I think there is a tendency for a lot of that stuff to just get completely compressed and suppressed as we get older. So that’s, that’s my view on why that seems to be the case.

[00:16:18] Yeah, as you were talking, I’m like nodding my head. I remember that teenage, you know, years and especially into my first job. I remember like really being self, not like self conscious, like not confident, but just really more aware of the approval of the room. And I think that follows you into your own business. I started my own business in my twenties, my first company in my twenties and I remember just a different relationship, you know, between me and problem solving because I was trying to like get that approval and it’s faded. It faded, you know, in my late twenties, faded in my early thirties. It’s just now that I’m like, I guess out of like adolescence, right, that I’m coming back into say more curiosity, more objectivity. It’s just easier to problem solve and explore. So I think it does, you know, happen in adolescence, and I’ve never actually thought of it that way. For entrepreneurs who are listening, going, yeah, like, I’m now curious about, you know, turning back on my curiosity and my decision making, can you talk a little bit about I’m going to talk a little bit about some of the specific benefits of asking good questions for growing a business from like a founder perspective.

[00:17:48] My communicating brain that I couldn’t imagine starting a business or trying to navigate a business without lots and lots and lots and lots of questions. But the questions we ask are also important. You can’t just ask any question, although, you know, I guess a question is better than no question often. But business is about problem solving and questions are at the root of the problem solving. Not just questioning others, but questioning ourselves and also questioning a particular problem we’re looking at. So even if we’re an engineer and we’re analyzing a particular problem within a system or a machine. The questions that we ask ourselves and the process of deduction and induction through reasoning is critical to how we get to an answer. A lot of times it’s not even answers that we’re looking for answers, but questions provide more than just answers. They’re catalysts of sort of the cognitive process. Without questioning our brain kind of just quiets down and just takes everything in and there’s times for that. But if you’re starting a business and you’re looking to be creative or if you’re looking to solve problems, questions are going to be a central part of how you go about doing that.

[00:19:11] I think it’s so fundamental, especially if you’re a founder and you’re looking to build something in order to address a unique problem and you may have a unique potential solution for it. All the questions from, you know, who is this useful for? Who might be interested in this idea? How can I use this idea differently? There’s a million questions to be asked that all help build out and build up whatever it is that you’re trying to create.

[00:19:44] Yeah, absolutely. There are just so many use cases for, you know, asking better questions, I mean, every single day in the business, right? Evaluating, like you said solving problems, making decisions.

[00:19:58] Do you have an example, maybe a story of a business person in one of your workshops who was kind of stuck in either indecision or stuck in a problem they felt like was really complicated and after putting, you know, good questions into the mix, they were able to get clear.

[00:20:20] Boy, there’s so many. One story I do mention in the book is around a design thinking workshop that I did and I continue to do. I had a bunch of medical device engineers I was working with. It was a design thinking workshop and if you’re familiar with design thinking, it’s essentially sort of trying to find you know, human-based solutions to complex problems, coming up with innovative ideas. So the scenario I had put in front of everybody was that okay, here’s the deal: we want to design a cosmetic sleeve for a prosthetic leg. But the prosthetic leg is for a very unique type of user. This is a child in Afghanistan, who is typically the the victim of landmines and there’s many of them but they can’t afford cosmetic sleeves. They could barely afford to have a prosthetic limb. So here’s the situation. We’re looking for solutions to this problem. But we have to keep it under, you know, 20 or something and we have to make sure that all the materials are locally sourced, et cetera, et cetera.

[00:21:29] So we broke up into teams and we used the design thinking framework and a big part of that is interviewing and questioning. We spent a lot of time on the types of questions one might ask in order to discover what might be the essence of the problem. So each of the teams had an opportunity to interview an NGO that works with these children and the each had 20 minutes to ask whatever questions. And I spent a lot of time designing the questions. Then they would go back and brainstorm ideas, and then they’d come up with an idea, they’d work on it, they’d put together a presentation, and there’d be a contest in the end to see what idea was best. But because I spent a lot of time talking about the essence of a problem, the problem is often not what it appears to be.

[00:22:18] Now, I didn’t say this explicitly, but I talked about it theoretically. If I present a challenge to you like a cosmetic sleeve you know, what is that solving? So, different teams thought differently and they all came back with really unique ideas. A couple of them came back with really brilliant cosmetic sleeve concepts, which were easily designed, easily produced, easily sourced and all that. But there was one team that went beyond that and decided that the cosmetic sleeve was a distraction. It was a distraction because the cosmetic sleeve was attempting to cover up the skin tone or the skin tone difference between the prosthetic limb and the skin tone of the boy’s body or the girl’s body.

[00:23:06] So they say, well, it seems to be after our interview that the cosmetic sleeve isn’t the problem. The problem is the stigma of having a prosthetic limb in this particular community in this part of the world. So how can we address that instead of answering the immediate question? They did a fair amount of research on the topic and then came up with an educational program that had nothing to do with cosmetic sleeve to educate. Because they found out that the problem, the children were having was that it was a real stigma to have this fake leg, this limb. And they were very self-conscious about it and other kids made fun of them. So that’s where this cosmetic sleeve came from this idea let’s cover it up, you know? So that particular team took a different road and through questioning, they were able to uncover maybe a deeper problem that really addressed the essence of why there was a problem to begin with now in the end that team didn’t win, and it wasn’t because of creativity. It had to do with practicality in some of the aspects. It also had to be feasible, viable, doable, and but the concept was great. The point was that through questioning and through that design thinking process of using questions, they were able to uncover that this thing that were presented as a problem statement may not necessarily be the problem statement.

[00:24:34] So we’re gonna ask better questions to get underneath the problem to see if there’s something else that’s hiding, which is often the case. You know, sometimes you see something, you say, here’s the problem. But I often say, is that the right question to ask? Are you sure that’s the problem you’re looking to solve? Now, maybe it is. But sometimes taking a few minutes to think it through to really understand the essence of what you’re trying to solve, could very well lead you down a different road.

[00:25:03] Example in a workshop where the teams using questions and using this process were able to actually see, see something differently than how it was presented, if that makes sense.

[00:25:17] I love that example. One the things that I talk to founders a lot about is the fact that, you know, every thought that pops into your brain is not necessarily the highest quality one. Every single thing that your brain wants to, you know, call your attention to is the most effective one in that moment. Oftentimes founders just want to problem solve anything that just comes to their mind and to do it very urgently. So I love that example because a lot of what we probably do as coaches is to with curiosity to ask some of these questions to make sure we’re actually solving for the right thing. Founders oftentimes will start a session, you know, thinking they need to solve one thing, in the session solving a completely different thing. I love that you brought that up. Let’s go beyond problem solving and decision making. What about in marketing and selling scenarios when a founder, let’s say, is selling B to B and they walk into a sales meeting and they need to have a conversation with that prospect. How can how can good questions help them?

[00:26:26] Yeah, well, as I was saying before, in the world of sales and marketing, certainly in the world of sales, questioning is really the coin of the realm. I mean, to ask good questions because the job of the salesperson is to discover and to uncover problems that may be apparent and may not be apparent to the prospect. Your expertise number one needs to come from a discovery standpoint and that is, I need to spend a lot of time understanding what the essence of the problem is before I can even consider if my solution is a fit. So I would always train my salespeople to say, listen, our product isn’t for everybody. Our solution isn’t for everybody, as much as we like to think it is. Most importantly you need to build trust with a prospect and through that building of trust, you want to be transparent and honest. You want to ask questions that help uncover what the true nature of what it is that they’re trying to solve.

[00:27:27] And if it turns out that, you know, our solution isn’t the solution, great, then move on. Don’t try to fit a square pig into a round hole. However, that questioning process is part of that discovery, part of that trust building, part of that bonding that needs to happen between a salesperson and a prospect where great questions will enlighten. Will build connection. Will show not just your expertise, but your ability to see and ask questions that really smoke out and uncover things that are maybe behind the curtain with that particular prospect. So I learned this process and I started teaching this process, many years ago in selling advertising through, you know, the teams for magazines.

[00:28:22] That discovery process where I actually created a framework for it, that I actually talk about in the book, I call it a three phase model and it can break down into three phases or five phases. It’s sort of a pyramid and it begins with this idea of discovery where it’s all about open ended questions. It’s about tell me it’s about observing. The second stage is what we call challenge which is after we’ve observed and asked good discovery questions. We’re now equipped to be able to challenge some of those questions and challenge the person’s thinking about how they’re seeing the problem. After you move through the challenge phase, there’s lots of techniques within the challenge phase using questions and hypotheticals and tag ons. All kinds of things that you can do as a salesperson to help move that process along. Until finally you get into your inference stage, which is where you use questions to come up with solutions. That’s a matter of making sure that you’re asking questions to have them provide either an answer or an idea that you’ve already led them to, you know, so it’s a little bit of a leading going on there. We’re using questions to help lead down a certain path and then you hopefully come to a conclusion and you walk away with some type of next step or agreement, you know.

[00:29:48] So that’s a very simple, simplistic way of breaking down questions in sales and marketing when it comes to not just persuading, persuasion obviously is a big part of that, but more importantly, it is about smart questioning to uncover, to connect, to build trust. To show that you’re a good critical thinker and you’re not there to force a solution that you have, on a problem that they may not be convinced that there’s a fit.

[00:30:21] What a relief. I feel like one of the things that, especially founders who are, just forming their sales and marketing skill set and learning how to do this, they think that their job is to persuade and it ramps up your nervous system. You get in, you know, you get this really anxious, nervous energy, and then you kind of repel the prospect. It’s just so wonderful that we can come into any sales and marketing scenario, and drop into that curiosity and all we have to do is ask questions. We can have a toolkit, a toolbox, I mean, of questions that we use to get the conversation started, and then our nervous system relaxes, theirs relaxes, and you’re right, that emotional connection happens. I’m so glad you talked about it because just too often founders are trying to go in there and get that approval to persuade instead of dropping into that curiosity. For founders who want to get started with improving their questioning skills, how do you suggest they get started?

[00:31:33] Well, you can start with reading my book, The Art of the Question.Yeah. There’s lots of techniques around the mechanics of questioning and scenarios and case studies on how to use questioning. Although it’s not all about sales, you know, you could say the big part of it applies to the world of sales. But you know, it is a matter of thinking about the questions you’re asking, making sure that your questions again aren’t necessarily about persuasion. It’s about understanding and it’s about discovery. So there’s other aspects to that I didn’t bring up sort of like the past, present, future questioning. Where when I was first starting off in sales, I would often sort of start with, you know, how’s business now, you know, what are you doing now? What’s going on? What’s reality for you now? What did it used to look like? What was, what was the past like, you know. You thread these questions, you know, very smoothly. So it’s not an interrogation, it’s a conversation which is very important. It’s a conversation. So this will then create a frame for what’s changed. Well, this is how it used to work. This is what we used to do. This is what didn’t work, blah, blah, blah. This is how the industry has changed. This is all about understanding your business, your industry, your pain points. Where are you now? Where did you used to be? And then once you gather that, then you fast forward and say: Okay, well what does the future look like? Where would you like to be? What would you like to see changed? What would you like to be different? So then you start to paint a picture of what the ideal future is.

[00:33:11] So you have these three time points. What’s happening now, what’s happened in the past, and what’s changed and now how do you see a future that’s better than the present? Through that conversation, which can be very deep and very lively and also very bonding because you get to understand their business and their experience. You’re then able to take all of that and go through the the three phase process, you know, so that first stage is all about discovery. Then you can then challenge. Say, okay, you talked about a year ago. This is what was going on with the company. This is what was going on with your vendors, blah, blah, blah. Then you can start to challenge some of those things. Also the future. I see you’re, you’re looking to, to increase market share. You’re looking to increase your market position in, in other areas of the world. What does that look like? How do you get there? You know, and then you start to challenge all of those things.

[00:34:11] So that conversation becomes very rich where both of you are problem solving together and you’re walking down the road together, right? Even though you can say you could be leading It doesn’t feel that way. It feels like you’re walking lockstep together as you try to solve this person’s problem or at least present an option to solve the problem. So, as far as, where to start, it’s a good question, but again there’s not, there are definitely books on sales and the techniques of different types of ways to sell but not too many of them really focus a lot on questioning from my experience. Some of them do, you know. But I would say yeah, my book, and then from there it’s a matter of just using common sense to a large degree and learning more about the questioning process.

[00:35:04] Mm hmm. Mm hmm. Yeah, I love what you just said which is that most of the books out there are about sales and I think that that can kind of be the wrong angle to learn sales from. Because you are, you know, asking the question, how do I persuade? How do I sell? So it can be really a better angle to take it from if you look at, well, what questions do I need to be asking? Because it shouldn’t feel like you’re pushing the sale when you’re doing it, or if you’re doing it right. So I love that you’ve taken this angle, I think everybody should grab the book. Where can they go to learn more and connect with you?

[00:35:44] Yeah, well, you can connect with me through a couple of websites, but the main website I’m concentrating on these days is Peak Luma, P E A K. L. U. M. A. Peak luma came out of the idea that luma is brightness and peak is about ascension. So I call peak luma sort of ascending leadership. It’s the idea of bringing the brightest to the top, type of thing, you know. So peak luma, you can connect there or grace media works is the other website. And of course the book itself is available through amazon. com. It’s just the art of the question and it has a red cover. There is another book that came out a while ago that called the art of the question. It’s very different. It’s a totally different approach to, to the concept. So it’s the red book by Sean Grace.

[00:36:40] That’s that’s great. We will make sure to link it up in the show notes, but thank you so much, Sean, for diving into questioning with me today. I’m sure that everybody listening is now curious to ask better questions. So thanks so much.

[00:36:56] Thank you, Kari. I appreciate it.

[00:36:57] Thanks for listening to this episode of Business Brain Rewire. If you want to learn more about my work, come visit me at DoBusinessBetterSchool. com. See you next week!

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