The Art of Posing Quality Questions

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John (01:03): Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. My guest today is Jeff Wetzler. He has been on a quarter century quest to transform learning opportunities, blending unique set of leadership experiences in the fields of business and education. He’s pursued this quest as a management consultant to the world’s top corporations most recently as CO CEO of Transcend, a nationally recognized innovation organization. And we’re going to talk about his most recent book today. Ask Tap into the hidden wisdom of people around you for unexpected breakthroughs in leadership and life. So Jeff, welcome to the show.

Jeff (01:44): Thanks, John. Great to be with you.

John (01:45): So I have a personal question totally unrelated to the book. How does the CO CEO work?

Jeff (01:51): A lot of people don’t believe that it can work. My co CEO and I, Alan Samoa actually had a chance to lead together and work together in a prior organization before we founded Transcend Together. So I don’t necessarily recommend it if you haven’t tried it out in a different way at first, but because we had worked together and we knew each other’s strengths and weaknesses and we knew that we complimented each other, we said, let’s give it a shot. And it has really lasted. We founded Transcend in 2015. It’s lasted us since then. As we look ahead, we’re actually moving into a stage. We’re going to shift into a solo CEO model after almost a decade as the organization has grown so much. But we really feel like the model served us really well up until now.

John (02:36): I suppose clear responsibilities, expectations probably really key to that

Jeff (02:39): A hundred percent. And good communication.

John (02:42): So one of the things you mentioned early on in the book that your own childhood or your growing up as an out or feeling like an outsider as one of the few Jewish kids, I’m assuming in a neighborhood kind of shaped a little bit of your perspective on this. I’d love to hear a little bit about that component.

Jeff (03:00): As I grew up, I didn’t always feel safe just saying everything I thought and felt. I had some signals that both explicitly and implicitly said to me, you know what? You may not be as safe as you wish you were here. And it just different people handled that differently. What it did for me is that I just kind of kept my mouth shut. And so instead of announcing my opinion, I would ask questions and instead of blurting things out, I would keep a lot of thoughts and stories in my own mind and head. And at some point it occurred to me, if I’ve got all this rich set of ideas and experiences going on inside of me, I’m probably not the only one. Chances are other people are too. And how much more interesting could things be if I could talk about it and if they could talk about it as well. I was always wishing someone would say, Hey Jeff, what do you think about this? And it led me to realize there’s probably others who feel the same way.

John (03:48): So I’m tempted to ask you to unpack the ASK approach. So you have kind of a baseline of where we are, but I’ve got a hundred other questions. But maybe let’s do the high level. What are the components of the ASK approach?

Jeff (04:02): Yeah, so the ASK approach is five practices that when put together, give us the greatest possible chance of really learning what person in front of us or the people around us truly think, feel, and know. Because far too often people don’t often tell us what they actually think and feel, whether that might be feedback they have for us or ideas for where we could take the business or critiques of our direction, any number of things, they stay too silent. We can talk about that as well. So the ask approach basically helps to solve that problem. And you want me to just run through each of the five real quickly? Yeah. Okay. So number one is what I call choose curiosity. And choosing curiosity is basically centering one single question in our mind whenever we’re interacting with someone. And that question is, what can I learn from this person?

(04:51): So it’s breaking out of the certainty that we so often find ourselves in where we might think to ourselves, I know what’s going on, I’m right there wrong any number of things, and it says there’s something I can learn from anyone. And when I’m here in this interaction, what can I learn from this person? There’s more to it than that, but I’ll leave it at that as a starting point. Now, number two is called make it Safe. And what it reflects is that even if I am super curious to learn from you, if you don’t feel safe telling me your truth, I’m not going to learn from you. And this is particularly important and I’ve learned this the hard way across lines of power when there’s power differences, but also other kinds of differences as well, when other people may not feel like it’s safe to really speak their truth. And so if we want to learn from them,

John (05:31): I’m going to say what I think you want to hear, right?

Jeff (05:34): Yeah. Or I’m going to keep my mouth shut. And so making it safe, it’s really about how do we create connection with the other person in ways that build trust? How do we open up ourselves so that they don’t have to guess at what is our agenda for asking them questions and also open up about things that might feel vulnerable for us to share too. And then what I call radiate resilience. How do we demonstrate to them that we’re not going to crumble based on what they have to say? We’re not going to flip out based on what they have to say. We’re not going to hold them responsible for the reactions. And so if we can create connection, open up radiate resilience, we go so far in terms of making it safe for the other person. Do you want to say you want to jump in?

John (06:11): All I’m thinking is I’m hearing you go through these. My first thought was a coworker. You want to learn something from that you think they could, which is great, but I’m also immediately jumping to somebody you think that you just are diametrically opposed opinion wise too. Totally. You think about the political divide right now that there are people that think, I can’t even talk to you because I don’t get you at all. And I’m kind of going through these going, well, maybe that would actually facilitate a good conversation.

Jeff (06:40): Yeah. I mean, the book ends by basically saying, I think the ask approach could be part of what we need to heal some of the polarization and divides that we have in our society. And I tell a story of how I got into an Uber with someone who I thought was basically diametrically opposed to me on a bunch of political issues. And by the end of the Uber ride, I realized we had so much more in common than I realized.

John (06:57): That’s amazing.

Jeff (06:58): Yeah. You

John (06:59): Want to go to number three? We’re on number three, right?

Jeff (07:01): Okay. Number three is pose quality questions. And so this is really the heart of the ask approach. Once we’re curious, once we’ve made it safe, how do we know what are the questions that are going to actually get to the heart of the matter? I kind of think of it this way that I imagine a surgeon would think about all their tools, their scalpels and all kinds of different things that they would have. I need this tool if I want to get to this. Well, questions are the same way, and most of us have one or two questions that we have as our go-to questions, but there’s a whole taxonomy of questions out there. There can be questions if you want to really understand what’s the root of someone’s perspective. You can ask questions if you want to understand where do they see the holes In my view, you can ask questions if you want to invite their ideas to make things better. And so this is all about choosing the right question based on the thing that you want to learn that’s posing quality questions.

John (07:46): So do we have a little index card box full of these questions that we need to tap into?

Jeff (07:51): Exactly. Exactly. And that’s basically what the chapter lays out. And then summarize it at the end is what are the most important questions, depending on what you’re trying to learn, but once you ask the question, it all comes down to how well you listened. It’s not enough just to put the question out there. And so the fourth one is listening to learned. And most of us think we’re good listeners. It turns out we’re missing so much. There’s a big difference between thinking we’re listening and actually hearing what someone has to say and also what they’re not selling us as well. For the book, I interviewed award-winning journalists who are professional listeners, and I remember one of them, Jenny Anderson saying to me after every interview, she records the interview and then she goes back and listens to it 2, 3, 4, 5 times. And every single time she listens to it, she hears something she hadn’t picked up the previous time.

(08:34): And I think to myself, if a professional listener misses things on the first time, second time, how much are we missing when we don’t record our stuff? And so this practice is all about broadening the range of information we’re listening for. And I talk about it’s not enough to listen just for the content of what someone’s saying, but also the emotion that they’re conveying and the actions that they’re taking in the conversation as well. So triple the channels that you’re listening through. And then the last one is called reflect and reconnect. And this is my favorite because I am a junkie for learning and reflecting is really how we take all the experiences that we have and we squeeze the learning out of it. That’s where we get the insight. And so reflecting is about what I call sifting it and turning it. Sifting it is first to say from everything that I heard, what’s valuable and what can I let go of?

(09:16): And then turning it is basically going through three processes where I turn it first to say, what did I learn from this person that would affect the story I have about them or about the situation or about myself? The second turn is what did I learn that would lead me to take certain steps? What can I do about it? And the third turn is, how can I grow more deeply? Does this speak to some of my deeper assumptions or values or ways of being in the world that either confirms them or challenges them or enriches them, et cetera? Those are the three reflective turns, but it’s not enough to just do those and walk away. This is why I call it reflect and reconnect. The reconnection part is so important. That’s going back to the person and saying, here’s what I learned from you. Here’s what I took away from our interaction, and here’s what I’m going to do about it and thank you. And that says to the other person, A, you didn’t waste your time. B, it gives them a chance to actually nuance what you took away. Maybe there’s something else they would want you to take away. And C, it really keeps the door open for future sharing as well. They know this is someone who really values what I have to say.

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Jeff (11:05): So those are the five practices of the ask approach in a nutshell.

John (11:09): Awesome outlines, let’s break some of this down. Great. First off, as I hear you talking about this, you even acknowledge this takes hard work, this takes brave, this takes being vulnerable. None of that sounds like a sales pitch. So how do you get people past that to say, Hey, I want to adopt this?

Jeff (11:28): Well, one of the things we didn’t spend as much time on before we got into the ask approach is, what’s the problem it’s trying to solve? Because the problem it’s trying to solve is also very costly. The problem it’s trying to solve is that when we have a customer who walks away but doesn’t tell us the real reason why, how painful is that? When we have a strategy that fails in ways that could have been predicted by the people around us, by our employees, by our colleagues, when we have an investor who passes on investing us because we didn’t actually understand what their true concern is when we have a friend who goes more distant from us because we didn’t realize the ways that we were impacting them, all of those things are really big costs that we pay. And it’s so prevalent that people around us aren’t really telling us the totality of what they’re thinking and feeling. And on the flip side, if we can tap into that, we can make better decisions together with other people, we can get far better ideas to innovate. We save a ton of time. Our relationships are so much more satisfying and fulfilling. That’s the payoff of doing this work. And it’s not like this work has to take hours and hours. It doesn’t take that long to say, here’s my idea. What might I be missing? That’s a very quick little thing that you can do. So anyways, how does that land with you in terms of

John (12:34): Yeah, I’m finding myself thinking particularly like in a sales environment, the objective may actually ultimately be, the end goal may actually be the same, but using this approach rather than me trying to sell to you, I’m actually trying to learn from you. And that probably feels a lot better to the person being sold to, even if the end result is we’re trying to get to this sale.

Jeff (12:59): Totally. It feels better. And it also, I think, reveals information that will make you make it easier to know what’s the objection I need to overcome that they have or what do they really value that I can speak to? And by the way, I might also learn that my product is not the right product for them, in which case, maybe today’s not the day to make the sale, but the trust that we have together over time is that much better.

John (13:20): Over many years of selling, as all entrepreneurs do, I’ve discovered that a lot of times I’m selling ’em on the benefit that doesn’t address what they want. I’m telling them, this is going to make you more money, and really what they want is more time. Exactly my fault for not addressing that. And so then they walk away.

Jeff (13:37): And incidentally, they also, when you ask them questions, and there’s really interesting research in the realm of dating when someone is dating someone else and asks the other person questions on the date, the person who’s doing the question asking is literally rated as more attractive. And so when you’re having a sales conversation or any other kind of conversation, if you’re asking questions, it draws people closer to you too.

John (13:56): Well, and you actually, I think in the intro of the book, you talk about how this approach actually benefits both people. That’s right. You’re maybe getting some information, but that person either feels a lot better or feels a lot more heard, right?

Jeff (14:09): A hundred percent. This is not just a one way extractive, I’m just going to kind of get what I need from you. This is truly a mutual benefit. And when somebody else has something that they’re thinking and feeling but are not saying to you and you can help them get it out, you’re enabling them to be more, enabling them to actually come closer to you. And chances are that it’s going to feel good for them, but also it’s going to get you to a better place together.

John (14:31): I’m guessing that this takes practice because you can make it feel like you’re being interviewed, and that’s probably not what we’re talking about. Or I don’t want to go, okay, Jeff, now I’m going to make you feel safe. Right? I mean, so how do we go about practicing this? How do we consistently apply these without them feeling kind of clunky?

Jeff (14:52): Yeah. There’s a chapter on this in the book called Make It Your Superpower, and it talks about a few things. One is you got to go from what I call conscious competence, which is like I’m unconsciously trying to practice this to unconscious competence, which means it just comes natural. It’s fluid. And the way to do that is just this very simple cycle of practice and feedback. Try it out in safe environments, try it out in small scale ways and tell people that you’re trying it out, especially if you can start with people that you feel safe to and say, Hey, I’m going to just try asking some different kind of questions. How did that land with you? As you do that, you’ll start to get the benefits of this. It’ll start to feel more natural, just whether that just like a golf swing or a tennis swing or any other kind of thing that you’re learning, but that practice and feedback cycle, then you start to take it out in slightly more high stakes context, slightly more risky kinds of things. And over time, you level up to be able to do it in more and more places.

John (15:40): Yeah, I mean, a lot of things in life, if we just took one of these and maybe ask some better questions. I mean, we’d be ahead, right? We wouldn’t have to master all of this, right?

Jeff (15:49): Yeah, exactly.

John (15:50): So you mentioned high leverage or high, can’t remember what you said. High something stakes, but higher stakes. Stakes, yeah. Is there a different way to address this when you know it’s going to be an uncomfortable conversation?

Jeff (16:03): I would say when it’s going to be an uncomfortable conversation, step one called choose curiosity. You got to invest even more in that because for me, in an uncomfortable conversation, my blood pressure can go up, my shoulders can go up, and I can be thinking to myself, how do I get out of here? Or how do I get this done? Or how do I convince them? Those are the places where I’m most likely to overlook the curiosity that I need, which is how does this other person see the situation? How might I be impacting the other person? How might I be contributing to the issue that we’re trying to solve together here? And so using that curiosity, I talk in the book about curiosity as a team sport, you don’t have to do this alone. You can actually say to a friend or a colleague, I’m about to go into a pretty high stakes conversation here, help me get more curious. Can you help me put myself in the other person’s shoes and just think, what might I be missing in this conversation? I can’t know it for sure because I’m not in their shoes, but I can be more curious about that. So that would be the one thing. And then the second thing that I would say to lean in heavily on is make it safe. Because if you’re feeling its high stakes, the other person might also be feeling its high stakes as well. And so I would go heavier on those two strategies.

John (17:09): Obviously this is a practice self-development, a great tool to master. Do you believe this is a practice that could actually be brought into the culture of an organization?

Jeff (17:19): I do. And there’s a chapter in the book called Make It Your Organization Superpower as well, and there’s a few important things there. One is leaders set the tone of cultures. And so one of the most powerful ways to get this infused in an organization is for people at the top to model this and practice this and say it out loud. I talk about in the chapter how valuable it is for the CEO of the organization to think about themselves as the learner in chief. And that doesn’t just have to be the formal CEO, that could be the president, that could even be the team leader, but to really be modeling this, but there’s other things to do, including even what we hire for in our organizations. In my first job out of college, after I went through this very rigorous hiring process, at the very end, they sat me down and they gave me a whole boatload of critical feedback, and I thought to myself, clearly, I’m not going to get the job.

(18:10): Why are they bothering to tell me all this critical feedback? It turned out they told me the critical feedback. They wanted to see if I was curious about it. They wanted to see is Jeff going to get defensive or is he going to say, huh, that’s interesting. Tell me more. And so it’s a way that you can screen for curiosity as well. In our own organization, we also have this practice that we call the two by two, where every quarter everybody sits down with whoever they work closely with and says, here’s two things I think I’m doing well, here’s two things I think I could do better. Here’s two things you are doing well, you could do better. And then we exchange it. And that’s just a practice that gets each other asking questions, it normalizes it, it clears out the closet, nothing fester. So there’s that kind of thing as well.

John (18:45): One last question before I let you go. Today, I’m all over curiosity. I’ve made the person feel safe. I’m radiating resiliency, but they just don’t like to talk. I mean, there are human beings that don’t want to be asked their opinion. How do you word deal with that? I don’t know. We call ’em introvert, whatever you want to call ’em. How do you deal with that person that just really isn’t comfortable in sharing?

Jeff (19:07): So you can’t force it on anyone, and you got to respect the limits. And sometimes it’s actually honestly in respecting the limits that they get more comfortable to open up. You’ve

John (19:16): Made it safer

Jeff (19:17): In making it say, if I’m constantly saying, come on real, I know you got something else, they’re going to shut down. But if I say to them, look, I’d love to hear anything you have to say and wherever you want to stop, that’s okay. Too often that comes more, but I’d go back to the create connection part of Make it Safe. And what’s interesting, when I interviewed some iconic CEOs for the book, they talked a lot about the time and place of connection. And so Bill George, the former CEO of Medtronic said, if I want to really talk to someone who I think is going to be hesitant, I’m never going to have them come to my office and sit across the CEO desk from me. We’re going to be taking a walk, we’re going to be sitting on a couch, et cetera. I see it with my own kids too. If I want to hear from my daughter how her day was at school, it’s never going to happen right after school. When she gets home, it’s going to happen 11:00 PM at night when she’s done talking to her friends and done with her homework and wants to stay up a little later, and then it all comes out. And so I would encourage you to just be thinking about the time and place of connection as well.

John (20:12): Yeah, my kids, it was always when I’d have to take ’em somewhere. Right,

Jeff (20:16): Exactly.

John (20:16): We’d get in the car and start driving, and all of a sudden it’s like, okay, this is a safe space. It’s

Jeff (20:21): Amazing how many people have said that. And there’s something about not sitting face to face with them, but sitting side by side that’s a little less intense, a little less confronting, and all of a sudden the guard comes down.

John (20:30): Yeah. Awesome. Well, Jeff, I appreciate you taking a moment to stop by The Duct Tape Marketing Podcast is there’s some place you’d invite people to find out about your work and certainly find more about Ask.

Jeff (20:41): Yes. So the book Ask is available anywhere books are sold. The website is www dot Ask dot, and people can also follow me on LinkedIn, Jeff Wetzler, or Ask Approach at Instagram.

John (20:52): Awesome. Well, again, I appreciate you taking a moment and hopefully we’ll run into you one of these days out there on the road.