The Art & Science of Asking Better Questions: Unlock Trust, Learning & Leadership with Jeff Wetzler.

“Your desire to know cultivates their willingness to tell.” – Jeff Wetzler

In this episode of It's an Inside Job, I sit down with Jeff Wetzler, author of Ask: Tap Into the Hidden Wisdom of People Around You, to explore the transformative power of asking the right questions. Jeff shares how curiosity, psychological safety, and deep listening are essential for meaningful conversations and effective leadership. 

Why You Should Listen: If you've ever left a conversation feeling like something was left unsaid, this episode will equip you with practical tools to ask better questions, listen more deeply, and build stronger relationships. Whether you're a leader, coach, or simply someone who wants to communicate more effectively, Jeff’s insights will transform the way you approach conversations.

Key Takeaways:

1. Curiosity is a Choice, Not a Trait – Jeff emphasizes that curiosity isn't something you either have or don’t. Instead, it’s a mindset shift that we can intentionally cultivate, especially in emotionally charged moments. By choosing to be curious, we invite deeper understanding and create a foundation for trust and learning.
2. The Art of Psychological Safety – People often hold back valuable insights due to fear or discomfort. Jeff breaks down practical ways to make it safer for others to share their true thoughts—whether it's through choosing the right setting, exposing our own agenda transparently, or demonstrating resilience in handling difficult truths.
3. The Quality of Our Questions Determines the Quality of Our Learning – Many of us unknowingly ask ‘clumsy,’ ‘sneaky,’ or ‘attack’ questions that shut down dialogue rather than open it up. Jeff walks us through his five-step Ask Approach, offering specific strategies for crafting open-ended, neutral questions that foster honest and insightful conversations.
4. Deep Listening is More Than Just Hearing – Too often, we listen to respond rather than to understand. Jeff introduces techniques like ‘pulling the thread’ and ‘echoing’ to actively engage in conversations, ensuring we fully grasp both the words and emotions behind what someone is saying.
5. Turning Insights into Action – Learning doesn’t stop at hearing—it requires reflection and follow-through. Jeff shares his ‘Sift It and Turn It’ method, a structured approach to processing information, extracting key insights, and translating them into meaningful change.

Bio

​Jeff Wetzler is a co-founder and co-CEO of Transcend, a nonprofit organization dedicated to supporting school communities in creating extraordinary, equitable learning environments.  Prior to co-founding Transcend, Jeff served as Executive Vice President of Teacher Preparation, Support, and Development, and Chief Learning Officer at Teach For America, where he focused on optimising the training and ongoing support of thousands of corps members nationally.

In 2024, Jeff authored the book "Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life," which explores the power of asking questions to uncover insights and foster breakthroughs in leadership and personal development.  

Contact

Website:  https://www.askapproach.com/

LinkedIn: 

Chapters

• 0:16 Introduction to Communication
• 2:32 The Art of Asking Questions
• 2:50 Meet Jeff Wetzler
• 4:29 The Power of Curiosity
• 8:41 Understanding Asking Beyond Questions
• 9:51 The ASK Approach Explained
• 18:15 Creating Psychological Safety
• 25:56 Recap of Key Insights
• 28:13 Transition to Quality Questions
• 31:34 Mistakes in Questioning
• 37:20 Listening to Learn
• 50:30 Reflection and Reconnection
• 56:27 Conclusion and Key Takeaways

Transcript

[0:00] Music.

[0:06] Welcome to It's an Inside Job, the podcast where we equip you with actual skills to build resilience, enhance communication, foster well-being,

[0:14] and lead and coach with impact. I'm your host, Jason Lim, and every Monday we bring you expert insights and real-world stories to help you thrive and succeed. And with that said, let's slip into the stream.

[0:27] Music.

[0:36] Hey, welcome back to the show. This week, we are going to dive into the art and science of communication. More specifically, the mindset and the ability to construct good questions. Now, a lot of us sometimes have heard that communication skills are soft skills. But from my experience, and I've spoken many times on this show, I think learning communication skills are the hardest skills to learn. Think about when you are in a moment of an argument or a conflict or some sort of emotional entanglement how hard it is to step back and to collect yourself and be grounded and to actually listen to the other person myself I talk about this all the time with clients and I find it very difficult I mean when we think about it I mean have you ever left a conversation feeling like something was missing, like there was more wisdom or insight or truth left unsaid. I mean, what if the key to unlocking that hidden knowledge isn't just about speaking well, but about asking better questions?

[1:39] So in today's episode, I sit down with Jeff Wetzler. He's the author of Ask, Tap into the Hidden Wisdom of People Around You, and a lifelong advocate for transforming how we learn and communicate. Jeff co-founded Transcend, an organization dedicated to reimagining education for the modern world, and has spent years studying how the right questions can unlock deeper understanding, stronger relationships, and smarter decisions. So in my conversation with Jeff today, we dive into a number of different topics, the art of asking questions, using curiosity as a superpower.

[2:15] Using emotions as learning cues, understanding psychological safety and communication, and the power of silence. So in this episode, we explore the skills and the knowledge behind asking the right questions, listening with intention, and uncovering the insights that might otherwise go unspoken.

[2:32] So let's now slip into the stream and meet you.

[2:35] Music.

[2:51] Thank you, Jason. It's really great to be with you. And we're connected between, I think it's New York City and Oslo at the moment, right? Yes, all the way around the world. Yeah. I was wondering, could we kick off our conversation today by you briefly introducing who you are and what you do?

[3:07] Sure. Happy to. So I'm Jeff Wetzler. As you mentioned, I'm based in New York. I am a father of two and a husband. And so family is probably the most important first hat that I wear of all the different hats. I'm also the author of a book that we'll talk about today called Ask, Tap into the Hidden Wisdom of People Around You. And over the course of my career, I have toggled back and forth between the business world and the world of education. And that's because my greatest passion in life is learning. And that's the common thread, I think, between business and education. And I truly believe that learning is our greatest superpower. In a world where the world is changing so quickly, where what we know today may not even be relevant tomorrow, our ability to learn, I think, is what is going to help us to survive and thrive. In a world where machines are taking over so much of what humans can do, our ability to learn is going to be ever more important. And I personally just find it so fulfilling. So I have pursued that love of learning in a variety of capacities, from being a management consultant to leaders around the world, to being an operating leader in organizations, to being an entrepreneur, and now most recently to being an author.

[4:29] Yeah, before we dive in the book, which I'm really intrigued to explore with you, I was wondering what inspired you to explore the power of asking questions? I mean, was there a defining moment or experience that kind of shaped this sojourn for you?

[4:44] I think I have always loved asking questions. I've always been a very curious kid and person. And so it's been in me for a long, long time. But I did have my first professional experience was at a consulting firm called Monitor Group, which is now part of Deloitte. It's called Monitor Deloitte. And one of the things that drew me to Monitor was that they had a leader there named Chris Argyris, who was one of the pioneers of the field of organizational learning. And so I was drawn to Monitor to learn from Chris. And one of Chris's observations is that sometimes the, quote, smartest or most, quote, successful people are the worst at learning. And especially the worst at learning from other people because they haven't had to experience failure as much. They haven't had to ask for help as much. Their self-identity sometimes is more around being successful than around asking other people what do they know. And so it was an interesting phenomenon of how do you teach smart people how to learn. And one of the biggest things that Chris taught me is that it has to do with how they communicate. So he had this really interesting methodology for helping people learn how to better communicate, where he would say to people, I want you to bring to me your toughest interaction.

[6:09] Give me a case example of a conversation that you had that didn't go well, that is representative of the kinds of interactions that you want to learn how to handle better. And he said, but I want you to bring it to me in a very special format. But I want you to take out a sheet of paper, draw a line down the middle, and on the right-hand side of the paper, I want you to write down everything you said, and then the other person said, and what you said, and the other person said, almost like you're writing a script of a play.

[6:37] But on the left-hand side, I want you to write down all the things that you were thinking and feeling during that interaction, but you never said. All of your unspoken thoughts and feelings, your private sentiments during the conversation. And that was what he called a two-column case. And over the years, I got the chance to work with hundreds and hundreds of these cases from people across all different industries, all different levels, all around the world. And I started to realize something, which is that once you strip away the junk and the venting and whatever else goes on in our private thoughts, there's some really important things that people aren't saying to each other.

[7:16] Things like, you know, I can see why your plan is about to fail, even though you can't see it. I can see why you're demotivating the team in ways that you don't want to be doing that. I can see a small pivot that if you would just make, would make all the difference. But they're not telling that to the other person. And the other thing that was happening is the other person not asking them questions to learn those things as well. And so So in the course of doing this work, it became so apparent to me the power that questions could have in unlocking some of the most important wisdom, insights, or genius that other people think and feel but don't tell us as well. And I had the opportunity to work with leaders and teams on this over and over again. And when they started to see the power that asking questions could have in unlocking the very results that they were not getting but wanted, it was a massive lightbulb moment for me. So that's a long answer to your question, but that's a little bit of how it started for me. That's why we're here. I want people that are not here to listen to me.

[8:17] So thank you for those long answers. Because I'd like to sort of rewind and sort of pop that open a little, sort of elaborate. So your book is called Ask. And I was just wondering, what does asking mean to you beyond just the act of posing questions? I know you've kind of touched on it. I was wondering if we could sort of explore that more beyond than just asking the query.

[8:38] What does asking mean to you? Yeah. So we can get into this more, but asking is not just the question that you ask. But asking is the curiosity that you have that's behind that question. Asking is the ways in which you create safety for the other person to answer that question. Asking is how do you listen to the answer. Asking is how do you make sense of what you hear. So it's the totality of that. But if I zoom out even one level kind of bigger than that, to me, the act of asking a question is not a one-way extraction of information from you to me so that I'm better off. But it's a process of mutuality, of mutual benefit. It's a way of connecting with other people. It's a way of giving other people the gift of self-expression. Because when other people know things but aren't telling you, they're not self-expressed. And so it's also giving them a gift. It's showing them how much value, how valuable what they know is, what they think is as well. So I believe that asking is equally an act of learning as it is an act of bridging across humanity and human connection as well. One of the things you alluded to was your...

[9:52] Your story about monitor deloitte you you were talking about there's sort of a two column conversation and some of the questions that we didn't ask and so you know we can all ask questions but there is an art and science that your book explores in order to do that and it's not just about the question mark but it's about the ecosystem around that so i was wondering could you sort of outline the ask approach i know it's a five-step process but i was wondering if you could briefly walk us through the sort of the key principles and why they are key or essential for locking deeper insight into sort of leadership and life in itself absolutely so the problem that the ask approach is trying to tackle is what we've been talking about is how do you actually unlock the unspoken ideas insights thoughts feelings feedback from other people who may task approach is five practices. I put them in a sequence, so I call them five steps, that are all grounded in research, but all tested in practice, that when put together, give you the greatest possible chance of really tapping into what other people know and think and feel. So I'll just go through each one. And Jason, stop me anytime you want to pause or go back and forth on anything. But the first one is called Choose Curiosity.

[11:18] And I start with curiosity because I think everything rests on the question of are we genuinely curious to learn from someone else? If we are just trying to use the quote techniques of asking questions but we're not genuinely curious, people will see through that and it will not be authentic. On the other hand.

[11:40] If we are genuinely curious, if we truly want to learn from someone else, they can tell. I think we give off an energy that lets them know we really want to learn from you. I have a mentor, Diana Smith, who had this expression, which I love, which is your desire to know. That means your curiosity cultivates their willingness to tell. So the more they can tell that you want to know, the more they will share with you as well. And I look at curiosity not as a trait that some people have and other people lack, or not as a state of mind that we're stuck in, like I'm just not feeling curious today. But I really look at it as a choice, which means that it's a decision that is always available to us. We can always choose to be curious.

[12:27] And there's a lot of gateways into how do you choose to be curious, and we can get into that more. But at the end of the day, they all arrive at this essentially centering one question in our minds. And that question is, what can I learn from this person? What can I learn from the person in front of me? And when we center that question in our minds, I believe it pushes out lots of other questions like, why are they so stupid? Or why are they a jerk? Or how do I get out of here? Or how do I just get them to do what I want to do? Like that stuff starts to fade away. and instead it invites other questions in like what do they see that i don't see how are they interpreting the situation where did their experiences and worldviews come from how am i impacting them all kinds of other things start to come up and so that is you know the essence of choosing curiosity yeah so curiosity is the first one so let's let's go into that because i think what you're saying it's it's it's not something we are inherently born with but it is a state of mind. It is a mindset we need to adopt because in conflict situations, let's say constructive conflict within an organization or a team, sometimes we don't want to say things because we don't feel safe or we feel there's going to be blowback or someone's going to hold it against us. Or if you and I, Jeff, are in an argument of some sort of a professional nature, I might think initially, as many of us do, that he or she has negative or bad intent, right? Right.

[13:56] But if I choose to be curious, then, as you said, all those kind of questions, they kind of fall aside. You said there's gateways of how to be curious, because I think this first step is the most important. It's the curiosity, at least from my perspective. How can we be more curious, especially if we're sort of riled up or we're in an emotional entanglement over a professional or private issue? One of the things that makes it hardest to be curious is when we're emotionally activated or triggered. When we are angry, scared, frustrated, our brain is going into fight or flight or freeze, not find out more.

[14:45] This takes a little bit of time and practice, so it's not something that you can do instantly. instantly, but with a little bit of practice, you can actually start to turn your emotional reactions into cues for curiosity. So there's a phrase I learned, which is just simply, when you're furious, get curious. When you're, you know, when you notice that you are really worked up about something, if you can have just the smallest amount of distance to notice that emotional reaction and not be stuck inside it, you can say, that is a reminder to me, there's more going on here than I realize. That's a reminder to me that I need to step back and ask myself, what might I be missing? What can I learn here? That's a reminder that I need to get a friend or a coach or a mentor or a colleague to say to me, help me get a little curious about this. And incidentally, nowadays, you can also do that with AI. If you really worked up, you can take your entire event, you can just rant it right into AI. And then you can just say to AI, can you help me get more curious about the situation. What might I be missing here? And what comes back is fascinating. And it's in the privacy of your own phone or your own computer. So you don't even have to let anybody else know. But if you could notice your emotional reaction, that is almost always a sign that there's something more to be curious about. And so you can actually flip it on its head instead of emotions getting in the way of curiosity. Emotions can be a gateway into curiosity.

[16:11] I really like that the emotion can be the gateway, it can be the window into curiosity. But as you said, this is a habit that takes time. It's not a light switch and it just happens. It takes time and practice and through experience we can refine our approach. But that would also suggest we would need some level of self-awareness to catch ourselves in the present moment before we go down the rabbit hole of argumentation or of fight and flight. Right. Do you have certain recommendations if someone's practicing this and they want to be better at being curious, Jeff? I mean, what do you do or what did you initially do to kind of catch yourself in the moment to sort of pump the brakes? Yes. Yeah. So the deeper forms of practice can include things like meditation, where you can notice what's coming up for you and what's going on inside yourself. Therapy where you can have a trained professional help you notice your emotions. But the very simple thing that any of us can do, if we're not yet doing any of those things, is just to look at curiosity as a team sport and to say, let me ask my life partner, my friend, et cetera, to say, hey, you seem a little worked up right now. Is there anything that you might want to be more curious about?

[17:27] And so even if we don't have the self-awareness to catch ourselves at the moment and say, let me use this as a cue. If we can enlist the people in our lives to help us do this, they will see what we're worked up and they can help us do that as well. So I do that myself. I have a, you know, I have a friend and a partner who I started my last organization with. And when he sees me really worked up about something, he's like, Hmm, well, you know, I want to practice what you preach. Take a little, a little curiosity here. Yeah. Yeah, no, I really like that. I really like that because we can use the people around us who understand our patterns, who it becomes quite evident when we are worked up and then they can point it out. And every time they point it out, that kind of makes us self-aware. And over time, it sounds like this becomes habitual. Exactly. Yes, exactly. Well said.

[18:15] So a second step was making it safe, which is another crucial step in your asked book. So in sort of personal, professional relationships, when we often, often, and I find this for myself too, I hesitate to share what we truly think. I was wondering, what are some practical ways we can create more psychological safety, I guess, to encourage much more transparent and honest dialogue? And especially in the professional environment, this is where psychological safety is bantered around a lot as a term. Exactly. And so this step is really about trying to bring psychological safety to the interpersonal level and to the team level.

[18:59] And to your point, even if we're curious to learn from someone, if they don't feel safe to tell us their truth, what they really think or feel or know, we're not going to find it out. And so in this step, I talk about three strategies for how to make it safer, easier, more comfortable for other people to speak truth to us. So I'll just go through them. The first one is just really about creating connections. And part of creating connection is a recognition that the most important time to create connection with someone is not during a high stakes interaction. But is well before that high-stakes interaction. It's a little bit of like dig your well before you're thirsty. Invest in that relational trust well before you need it. Because I think that probably upwards of 90% of how an interaction goes is not about what happens in the moment of that interaction, but it's what's happened leading up to that interaction. And so that's part of creating connection. And then also part of creating connection is being mindful of the time and space and place when that connection is happening.

[20:05] And in particular thinking about how can you do this in the space and place and time that's most comfortable for the other person as opposed to what's most comfortable for yourself and so when I when I researched the book and I spoke to a lot of CEOs and I said to them you know CEOs are notorious for not getting the truth from people people lie to CEOs because they want to look good to the CEO or they want to get their agenda through or whatever and I said to the CEOs how did you get the truth out of people? And one of the things that they said is I would never bring someone into my office and make them sit across the big intimidating CEO desk and assume they're going to feel comfortable. Like I'm going to go to them. We're going to take a ride along, have lunch, take a walk, eat in the cafeteria, whatever it is. And there was no single answer other than wherever is most comfortable for the other person. And this is true for me in my personal life as well. So like I have a teenage daughter and when she comes home from school, I want to know how her day was. I want to know what happened. What did you learn? How were the friends? All that kind of stuff. And when I ask her when she comes home from school, you can probably guess I get nothing. She doesn't want to talk to me about it. When I ask her at dinner, I get nothing.

[21:15] The only time I can get it out of her is when she is most comfortable, which is usually 11 p.m. When she's done with her homework and she's done talking to her friends and she's in her room. And at that point, it all spills out. And I'm, of course, like wishing I was asleep at that time. But if I want to learn from her, I've got to do it where she was most comfortable. So that's all about where and how to create connection. Another part of making it safe is when you're asking a question to someone, they are going to be guessing, what's your agenda? Why are you asking that question? And so the more that you can just expose your agenda, let them know, here's why I'm asking. Then they don't have to guess. They don't have to worry. Is this a gotcha? What's going on here? And when you expose your agenda, the more that you can do it in your own vulnerable way. So to say, like, here's what I'm stuck on. Here's why I'm asking. Here's why I need your help. The more vulnerable we are, the safer it is for them to feel vulnerable. And then the third piece of it, I'd call radiate resilience, because I think people are constantly measuring how resilient are we in terms of how much can we actually handle a hard truth.

[22:23] And if they think that we can't really handle their truth, they will sugarcoat it or they just will dance around it or they will protect us from it. But if they think that we're resilient, they're much more likely to actually give us the real thing. And so there's different ways to radiate resilience. One of the ways to radiate resilience is simply to name the elephant in the room to say, look, if I were you, I might be feeling really frustrated about this right now. And if that's what's going on for you, I'd love to hear that. Another way to radiate resilience is to explicitly invite critical input from them. So I have a colleague who used to say, Jeff, give me your most critical feedback on this document. Even just the way he asked that question sent a message to me about his resilience because he wanted to know what could make it better. He didn't just want me to praise it. Another way to radiate resilience is after someone tells you something hard, to praise the messenger instead of shoot the messenger. So I remember at one point, I gave somebody some really tough feedback. And he said to me, thank you. And I feel like I can trust you even more now because I can count on you that if you don't feel good about something, you're going to tell me. So thank you for that. I mean, that said to me, like, this person's resilient. They really can take it. And not only can they take it, they want the input. So create connection. Open up, radiate resilience. Those are all, um, I think three very actionable ways that we can begin to make it safer for other people.

[23:46] And I just want to sort of riff on the last point there, radiate resilience. I think that's such an astute point you're making because a lot of people go into a hard conversation, let's say in the professional environment, you know, there's kind of two moral imperatives. There's honesty and benevolence. And a lot of people will think, okay, in the short term, I don't want to hurt the person. I don't want to be seen the bad. I don't want to rock the boat. So they will sacrifice honesty for benevolence, right? Then they think, oh, I'm just going to be nice. And they never tell the hard truth. And the question is, what happens to the credibility of the person giving the feedback when that person finds out that he or she wasn't truly honest? You know, just tell it as it is so I can improve. And so that person giving the feedback can get lost in the short term of, okay, I don't want to rock the boat. I don't want to feel this emotional awkwardness or uneasiness. And so they sacrifice the long-term benefit of the relationship, but also the development, let's say, their direct reports.

[24:40] Totally. But that's why I think that really resonated with me, what you just said there, Jeff. Because when you radiate resilience, I think that means you also have the long-term perspective experience. In hand and that you see, there's not one or sacrifice. I can be honest. I can be diplomatic and civil about being honest, but at the same time I can be nice. But sometimes I have to have the hard conversation with a person in order for us to enrich and create more credibility in our relationship, but also to develop that other person. I just wanted to riff on that because I think that's such a relevant point. I totally, totally agree. And there's so many instances where somebody who has feedback to give doesn't really give the most important feedback, to your point, maybe because they're trying to be benevolent. And I think there's a lot of important training that goes on to encourage the feedback giver to be more direct. And yet still people are often not direct. And so I'm trying to come at it from the other end and say, what if the feedback receiver could do a better job making it safe for the giver to give it? How much more might come out from that end of it? And a big part of that is the feedback receiver to be radiating resilience so the giver knows they can handle it. It's not going to hurt them.

[25:57] In the first half of our conversation, Jeff and I explored the power of asking the right questions and how we can unlock deeper wisdom, insights, and human connection. Jeff shared his experiences from his time at Monitor Group, where he encountered the challenge of helping highly intelligent people continue learning effectively. This led them to the realization that learning isn't just about acquiring information. It's about mastering the art of asking questions.

[26:24] Jeff introduced the two-column case method, a tool where one writes down both their thoughts and feelings during conversations. Now, this practice helped him recognize that asking questions isn't just about eliciting answers. It's about creating psychological safety for the other person to share openly. He emphasized that ask approach is a structured, research-based, five-step process designed to surface unspoken thoughts, feelings, and insights that people may otherwise keep to themselves. We also discussed the importance of curiosity as a learning mindset. Jeff believes that curiosity isn't an innate trait, but a choice. One that fosters deeper understanding and invites new perspectives. Now, another key theme was the idea of turning emotional reactions into curiosity cues. Jeff explained that rather than suppressing emotional responses, we can use them as prompts to ask better questions and to seek deeper understanding. This, however, well, it takes practice and self-awareness.

[27:23] And as Jeff noted, he said that emotions often serve as a gateway to curiosity. So if we learn to lean into them rather than to avoid them, there is so much there to learn. Another key element we talked about was psychological safety and communication. And that's about creating environments where people feel safe to speak honestly. And this might be as simple as choosing the right setting. If you're going to have a difficult conversation, maybe it's to move away from the office space and maybe go on a walk and talk, where there may be a deeper and more open conversation. So in this first half of the conversation, it's centered around how the quality of our questions shapes the quality of our learning, our relationships, and leadership. And it's by approaching communication with curiosity, emotional awareness, and psychological safety that we can definitely unlock deeper insights and build

[28:11] stronger, more meaningful connections. So now let's slip back into the stream with the second part of my fascinating conversation with.

[28:18] Music.

[28:26] Also in the book, you emphasize the power of the quality of questions. I was wondering, you know, we can all ask questions, but what are some of the biggest mistakes or pitfalls we make when we're asking questions? I mean, how can we shift towards more effective and open-ended ones, I guess I'm asking. Yes. Yes. So this brings us to step three of the ask approach, which is called pose quality questions.

[28:52] And very few of us, I think, have actually been taught what makes for a quality question. And so we go around asking a bunch of questions that I think are not quality questions. And my definition, by the way, of a quality question is very simply a question that helps you learn something important. So I'll give you some pitfalls to your point. One pitfall is what I call clumsy questions. And clumsy questions are questions that are well intended, meaning that they actually do want to learn from the other person, but they are designed or formulated in such a way that makes it hard for the other person to answer them in a way that you're going to learn from them. So can you give an example? Yeah. So there's a, I'll give you a couple of examples. One is what I call layering of questions. So sometimes people will ask three or four questions at the same time, and then maybe they'll say something after that. And then they, you know, the person being asked the question gets lost. They're like, which question am I supposed to be answering here? And by that, I forgot your first question, you know? So that's just one, you know, that's, that's what I call clumsy. Another example of a clumsy question is a question that might be well intentioned, but can sound rhetorical. So for example, if I'm saying something to you and then I say like, isn't that right?

[30:00] I might be actually wanting to know, do you think that's right or whatever? But when I say it like that, it doesn't actually sound like I really mean that I want to know from you. So those are some clumsy questions in my mind. I'm asking Elsa as a podcaster who asks a lot of questions. So I might as well go to the guru here and help me masterclass your own asking questions. I'm enjoying your questions so far. So I'll give you two other examples of question pitfalls and then we'll go into quality questions. Um, another is what I call sneaky questions. Um, and sneaky questions are questions that are designed to maneuver or manipulate somebody to, to essentially give the answer that you want them to give. Um, so you see this, you see lawyers do this all the time when they've got somebody on the witness stand and they're trying to get the, you know, or, or the defendant and they're trying to get them to basically say, now, wouldn't you agree that this, and if this was true and you know what, you know, all, and it becomes very hard for the person to not just agree with what the lawyer is trying to get them to do. But we do it all the time in our life, too. You know, don't you think it'd be good to go out for Chinese food tonight? Or don't you think, you know, have you ever thought about seeing a therapist? Whatever it is, you know, we've got it. We've kind of got a goal in mind. And we're using the questions to try to get the other person to the goal. And generally speaking, I think other people see through that. And they feel manipulated. And no one likes to feel manipulated. But people use sneaky questions because it somehow seems like it's going to go over better than if I just say what I really think.

[31:29] And then the other question pitfall is when people use questions, what I call attack questions.

[31:35] How could you ever think that that would be a good idea? You're essentially weaponizing the question to attack the other person, but you're somehow putting it in the form of a question. All of those go in the bucket of what I call crummy questions. They're not quality questions. On the other hand, quality questions are clear, they're clean, they're direct, they invite honesty, they invite the totality of a person's experience.

[32:03] What I talk about in this chapter of the book is just the same way that any professional has tools that they use. So like a surgeon, for example, has their scalpel and their forceps and their suture and all the different things, and they know what tool to use depending on what they're trying to get done. The same is true for questions. There's a taxonomy of question strategies that we can use to learn different things that we're trying to learn. And it's not like there's 50 or 100 or different you know there's about a dozen or so quality question strategies that if you can learn to just master this set of question strategies, you will have a far broader repertoire of what you can ask and therefore what you can learn from other people and so i lay out these in the book and i'll give you one example here um which is a question strategy that i call request reactions um and request reactions is simply saying to the other person, hey, here's what I think. What's your reaction to that? How does that land with you? What does that make you think? How does that sit with you? What might I be missing? Any of those are questions that are designed to allow me to learn the other person's thinking about my thinking.

[33:17] So that if they disagree with my thinking, or if they see a hole in my thinking, I am more likely to find that out. And then we can talk about it. And I think many of us don't ask a question like this because we assume, well, they're going to tell me if they disagree or they're going to tell me. And some people might, but for all the reasons why we just discussed, people often don't feel safe. Chances are you're not going to actually hear the totality of their thinking unless you use some version of the strategy, request reactions. I remember one time when I was first taught this myself, I was a new manager and I had just given the person that I was managing a set of instructions on what I wanted him to do. And then I remembered, let me ask for his reactions. So I just simply said, hey, what are your reactions to that? And he was quiet for a minute. And then he said, if you really want to know my reactions, I'm completely demoralized by what you just asked me to do. And I was stunned because I thought it made a lot of sense what I was asking him to do, but he didn't. And so we unpacked it and we realized that we were each operating off of different information and assumptions about what the client needed. And from his information, what I asked him to do made no sense. From my information, it did. And so we were able to exchange information, get back on the same page. And I think, you know, and all of that took five or 10 minutes. And it took me 10 seconds just to ask the question. And had I not done that.

[34:42] I think he would have really walked away very demoralized. He probably would have done something that didn't actually make sense.

[34:48] We would have wasted weeks of time. But in the 10 seconds it took to ask the question and then the 10 minutes it took to discuss it, we save weeks and weeks of time and a lot of heartache in our relationship too. I think that's a very good example that illustrates that all of us at some point hit that kind of crossroads. But we're we're functioning on two different narratives two different understandings and then we go down the rabbit hole of conflict or arguments or whatever it is but you actually stopped at the crossroad by shifting the quality of the question which allowed for, going from whatever position down to the needs and that's where you found sort of the connective tissue to move forward that's right that's right exactly yeah and by the way had i asked about a lower quality question like for example if i had said hey does that make sense he might i don't know that he would have given me that same reaction because he might have been like well it makes sense i understand what you're trying to do so he would give me a nod um but it's you know so it's to me it's fascinating how very subtle shifts in the design of a question can have dramatic implications for for what we do or don't learn yeah and again there was there was one question you posed is like how does this land with you jason yeah whoever yeah i think that's really good because it's a neutral uh that's right you've asked a neutral way of questions it's not leading it's not trying to push them on the one side of the fence or other it's just like.

[36:13] Well, how does this land with you? Right. But again, I think that comes back to your your second point in the book, you know, about creating psychological safety, because if I don't trust Jason, if I he's a new leader or whatever it is, I'm going to give him the normal respect. But there has to be a track record in which that question is going to land. That's right. That's right. So I think that's why the way you've sequenced the second step of making it safe or psychological safety is so key to creating that fertile soil in which you can ask quality questions. That's very well said. I totally agree. I totally agree. For me, questions are one side of the coin. On the other side of the coin is listening. Now, a lot of us tend to listen to respond instead of listening to learn that sort of that curiosity you speak to.

[37:08] I was wondering if you could share an example maybe of how deep listening has really has led for a breakthrough for you in some way or one of your clients.

[37:18] If you have a story. Happy to. Yeah. And just to sort of underscore what you're saying, listening to learn is step four of the ask approach. Sorry, sorry. Yes, yes, absolutely. And so it's a good, you know, you're taking us to the exact right place. And to your point, listening to learn is different than listening to respond or listening to prove a point or listening to look right or listening to get someone to do something or even listening to look like you're listening. That's all different than listening to learn.

[37:46] Listening to learn is really trying to understand the essence of what someone's telling you. And we can talk about how to do that. But to your point, for example, I mean, I think that as a leader in an organization, one of the things that I'm constantly trying to do is make sure that staff, especially some of the most talented and high performing staff, are feeling satisfied and engaged and want to stay in the organization. And so I'm, you know, quite often in a position of asking them about their experience. What are you liking? What's not what could be better? Where do you see yourself in a few years? Well, you know, what's important to all that kind of thing.

[38:34] And then I am really charging myself with listening to learn from them. And so when I'm listening to learn, I'm listening not just for the the words that they're saying, the information that they're conveying, but I'm trying to listen also for the emotions. Beneath that, the needs, the desires, the interests, and I'm not assuming that what I heard is correct. So I'm saying to them. Let me check. This is what I think I'm hearing you say. Is that right? What more did I not hear? Or how would you correct what I would say? And so this active listening is constantly, there's a strategy I'm listening I call tell back and test. I'm telling them back. Here's what I think I heard you say. Let me test that. Did I get that right? And, you know, whenever I do that, you know, people will say to me, yeah, you said that, but there's, you know, there is this other thing that matters to me, too. I also care about, you know, this dimension of my career, or I care about this thing that's going on with my family that I want to also be balancing. And so I'm hearing that. And then I'm also doing something that I call pull the thread.

[39:40] And it came actually from my research in the book where I interviewed professional listeners, you know, people like journalists, but also psychotherapists. And you have experience, is that right, in the world of therapy? Clinical therapy. I don't know if this has been your experience, but when I talk to therapists, they constantly refer to this thing called the doorknob moment. I don't know if you have this as well, but it's basically that when, you know, if it's a 50-minute therapy session, at minute like 49 and 59 seconds, when their client is about to leave the room, they've got their hand on the doorknob, that's when the most important thing that they have to say comes out. That's when they say, you know what? This is really what I care about. Or I'm thinking about leaving my spouse or whatever it is. And the therapists are thinking to themselves, why did they not say this to me during the session? Like, why did they wait until their hand's on the doorknob to tell me the most important thing? And sometimes the therapists are thinking, well, maybe it's because they were working up the courage to say it. Or maybe they were waiting to see how I responded to say it. One therapist said to me, I think it's because they want me to be thinking about them all week. So they say it at the very last minute. So I'm thinking about that until I see the next time. But whatever it is, you know, the point is that, you know, the therapist had been asking them questions all along and this thing didn't come out. And so the takeaway for, I think, for us, for listening, is that when you ask someone a question...

[40:59] Their first response might not be the thing that is actually the most important thing they have to say to you. In fact, maybe not even their second response. And so pulling the thread is just simply saying them, you know, thank you. And what else? What more? Is there something more? Is there something else in addition to that? And quite often, some of the most important stuff comes out only after the second or third follow-up question. And so back to my example, when someone says to me, like, this is what's going on in my experience, I won't just assume that that's the thing. I'll say, got it. Thank you. What else is going on in your experience? And what more? And just continuing to pull that. And time and time again, over the course of my career, this kind of listening has enabled me to retain some of the most talented, most high performing, high contributing people.

[41:51] Not because I'm getting to do what I want them to do, but because I've deeply understood their experience, their hopes, their desires. And from that, we can then get a creative path forward for them and say, what if your next six months look like this? What if we work towards this as a goal? What if we, you know, that kind of thing, to the point where they're like, this would be a no brainer for me to want to stay and go after this because it totally aligns with what I personally care about.

[42:15] I think one of the most, I think what you've just said is such a salient point because when I see therapists or psychologists or coaches out there, I think the most successful, of any of those professions, well, why they have such great client lows and people keep coming back to them, it's because of the questioning from curiosity, as you've articulated. It's because of the deep listening to truly listen and not to respond. And I think it's also the use of silence. And back to what you said about the sort of the doorknob moment, what I've found in both when I used to work in sort of the clinical setting, but now in the corporate setting, is that a lot of the times when people come and sit down and you've asked them an open-ended, curious type of questions to learn and understand their perspective, is that a lot of the times they're explaining it to you, of course, so they're trying to articulate their abstract thoughts and emotions into concrete, tangible words. But a lot of times, although they are explaining it to me, they may be explaining it to themselves out loud for the first time. And that's why people kind of get lost.

[43:24] Maybe it is, I want him to think about me all week till the next time we meet or the next two weeks. Or it could also be that they've got this ball of string, this ball of wet string, and they're trying to untie everything, Jeff. And it's through their articulation of what's concerning, their worries, what's on their mind to another person is that listening to their thoughts at the same time is... It's kind of all over the place, but through the 50 minutes, it becomes untangled. And sometimes, yes, it's the 49th minute and they're about to reach for the doorknob, but everything then kind of falls into place. Yes. I love that. Yeah, yeah, yeah. I appreciate that. And just to follow up on one thing that you said, because I also think about this and talk about this, the use of silence and how important it is to give the question some breathing room. And to give it some space and to not just rush in and fill the silence. I'm curious, how do you use silence in your work?

[44:28] I use silence because it took training. So this wasn't a light switch. It just went on. What I do is I sit and what feels like two minutes for me, I know it's only two seconds for the other person. A lot of the times i'm very cognizant of sort of the body language of the other person because you can if you train yourself if you are observant you can see when someone's truly sort of internally reflecting and kind of working through some thoughts or emotions right and then there's a switch there's a flick and then they start speaking but generally i'll sit silent by my silence and just let them process. Because sometimes the question may be very simple for me, but it's actually hit something deep and profound in that person. And it kind of percolates, it bubbles up and you can see them processing and processing. And so I've learned, and this is a habitual way I communicate now in my professional settings, is that I just sit there quietly. And sometimes I look down and like I'm taking notes. So it gives the person a little sort of space if they're looking at me that I'm occupied with someone else, but allows them to process.

[45:50] But then there's a click, there's a switch, there's a pivot there. And then the person starts, well, you know, slowly, but then it comes out. But that's how I tend to use it.

[46:02] Because I know for me, it's a lot of dead space, dead airspace. But for them, it's literally, it's like seconds. It's nothing, right? I've asked the question. They're sitting there processing for a minute, maybe two minutes, maybe a little longer. But then they hop in. For them, there's been no time gap. Yeah because in their mind they're actually talking to themselves and working and thinking and doing and so yeah yeah the processing exactly exactly well said yeah yeah oh i love that i appreciate that i've also heard somebody say uh someone parker palmer who i interviewed for the book said you know there's there's you and there's them and there's silence and silence needs to get their turn as well just the same way you get your turn and they get their turn gotta give silence their turn to be able to do that too i really like that i really like that it is sort of the ghosts in the room silence is there and he or it needs its space too i really like that i really like that just to riff on the listening before i move on to the questions i was also taught something called echoing and what this does this this teaches us to not listen to respond but listen to truly listen and what that is is because our brain is sometimes automatically looking for or the next response, or an answer, or the next interjection we want to put in. But if I echo what you're saying, Jeff, in my head, I actually hear it twice. And since the brain can only focus on one thing at a time.

[47:29] Then I'm listening to your words twice, because you might say the traffic was crazy on the way to the work today, and I'll be repeating the same words in my head. And this way, I'm not coming up with a rebuttal. I'm not thinking about the next questions. I'm truly listening, and it resonates to me at a deeper level. Now, I've been doing this for 30 years, and so this is just automated in me. But I think echoing, maybe it's called something else now. Back in the day, that's what the skill we've learned. it really helps me listen at a really deep level and my brain automatically kind of works at that level to see if there's any sort of um weakness in the foundation of their argumentation or whatever they're saying right but again i i ask questions based on a lot of what you've you've from your experience that you've talked about and it's really helped me to truly learn because.

[48:23] One thing, Jeff, why people do things, if I sit in my head trying to sometimes understand the reasoning why someone would do something like that, I would go insane after a while. I've just given up trying to figure it out. I just, as you said, I just ask the questions, but I ask the questions in neutral ways. And I just, then I learned, ah, that is why in a million years, I could have thought it over and over and over. I would have never come to the same conclusion that they've come to, right? So I just wanted to say that. So echoing is something that I've found that has really helped me truly listen at a deeper level without responding right away.

[49:04] So just to check, every time someone says something, you essentially repeat it to yourself inside your own head? Pretty much. Or I paraphrase it to some extent. Oh, you paraphrase it to some extent. Okay. Yeah. Fascinating. I appreciate you sharing that. Yeah, yeah. It's just something I was learning. But that's become automated. At first, it was really awkward. That's why we had a lot of role playing, right? I can imagine that one of the things that that does is that it kind of replaces whatever other noise might be going on in your head when they're speaking. To your point, you can focus on one thing. And so it's like if I'm going to be echoing what you're saying, I can't be thinking, you know, what's for lunch today? Or I can't be thinking, you know, why is Jason doing that or whatever else?

[49:47] It increases the degree to which I can be present to you because I've got to be taking it in inside my own head exactly what you're saying. Exactly. And I'm not constantly coming up with a rebuttal and such. Anyways, I just wanted to share that. Yeah, no, I really appreciate that. I was wondering, so when we are curious and we're gathering insights to help someone and sometimes translating insights into action is a whole other challenge. I was wondering, what are some key ways our listeners can, or people in general can reflect on what they've learned and to actually turn that into meaningful change? Do you have any advice along those lines?

[50:28] Yes, perfect. So this is the fifth and final step of the Ask approach. It's called reflect and reconnect. It's my favorite of the five steps because, as I mentioned at the beginning, my passion is learning.

[50:39] And reflection is how we learn. Reflection is how we convert our experiences into insights and our insights into action. It doesn't happen without some kind of processing going on. And I think that in general, reflection gets a bad rap. People think to themselves, I don't have time to reflect. I don't know how to reflect. Maybe I have to go on some meditation retreat to reflect. But in reality, reflection can be straightforward and simple. And so I offer a structured process that anyone can use to reflect on what you heard someone say to you. And the method is called sift it and turn it. So the sift it part is very simply, if someone tells you 30 things, they might not all be equally important. They might not all be equally even healthy for you to take in.

[51:26] And so sifting it is to say, of all the things that I heard, what matters most? You know, if I heard 20 things, what four or five things should I really be sitting with and taking away? And you can sift it on your own. You can sift it with a friend so that you don't sift out the wrong things or a coach or a colleague or a mentor, thought partner, but first sift it so that you get, you know, you've boiled it down to what's most important and then turn it just means turn it over in your head three times. The first turn is what I call turning it over for your story. So what did I hear from this person that might shift or enhance or elaborate the story that I have about them or about the issue or about what's going on in the situation? So now I have a more complete story from that first turn. The second turn is steps. Based on my revised story, what steps should I take? Maybe I should apologize. Maybe I should double down. Maybe I should go in this direction, whatever it is. But really isolate. What steps do you want to take? And then the third turn is this is the deepest turn, which is the turn for your stuff.

[52:30] The deeper stuff that you bring into every situation. So is there something I learned that sheds a light on some deeper assumption I've been holding or some bias I might have, or some way of being, or some story that I've got that I'm always bringing every situation. And that third turn of, of, of turning it for your stuff can be a little bit, you know, scary or emotional. Um, but when you do it, it's often where the biggest breakthroughs come through. Um, and, and then that will help you in many other situations because we bring our stuff to every situation. So just to recap it, sift it and then turn it. Turn it for your story, your steps, your stuff. And that's the reflect part. But I call it reflect and reconnect because this is not a process that's just about you taking things away for yourself. Reconnecting is closing the loop. It's going back to the other person and saying to them, first of all, thank you for what you shared with me. Thank you for taking the time to share that. And by the way, if it was scary, thank you for taking the risk to share it as well if it felt uncomfortable.

[53:28] And here's what I learned. This is what makes me think. And here's what I'm planning to do with what I learned. And by the way, is there anything more or different you think I should be learning from our conversation as well? In case I might have missed something in my reflection. And the act of that reconnection, I think, is a profound act. And I don't think it happens often, but it says to the other person, you didn't waste your time. You're powerful to me because you have influenced me. And I think it brings us closer to the other person and it significantly increases the chances that they're going to continue to share important things with us over time. We are coming close to the top of the hour, Jeff. I like to ask all authors, what did you learn about yourself through the research, through the interviews and putting pens to paper? Yeah, so much. What's the top thing? Yeah, I would say the top thing is I learned how important it is for me to be asked questions by other people. Because, you know, when you're writing a book, no one's asking you a question. You're just putting it out there.

[54:35] And I often found my own stuff coming up, which was, why would anybody want to hear this from me? Why would anybody want to hear my stories? They're not that interesting or whatever else. And so I realized that I sometimes struggle with sharing what I really have and know and think and feel. And it's so much easier for me when someone else asks me a question because it signals to me that they actually want to know. But there's also work for me to do in just feeling more safe and comfortable on my own sharing of myself. So you've written this brilliant book, Ask.

[55:10] Listeners are thinking, okay, where can I pick this up? Is it available in all formats? It's available in all formats, hardcover, Kindle, e-book, audio. You can get it at Amazon or independent bookshop, anywhere you want. And there are there's a lot more on the website as well so there's a website www.askapproach.com where you can find some articles and podcasts and resources and videos and different things like that to go deeper on this as well and you can sign up for a newsletter if you want to continue to learn more as things come out about ask and if someone wanted to directly contact you would going to askapproach.com be the best place yeah you can get you can get to me on askapproach.com you can also connect with me on LinkedIn as well. I love to connect with people on LinkedIn. So either of those two places, people can get to me. Jeff, thank you very much for such an enlightening and eye-opening conversation. I learned a lot. I thought I knew a lot, but you've added so much more that complements my skill sets. So thank you very much for that. Well, I really appreciate that. And I also learned from you as well. I had not encountered echoing before, just as one example. And so I really appreciate that it was a two-way learning process.

[56:20] Music. Well, folks, if there was a key theme that stands out in this great conversation, it's that the quality of our questions determines the depth of our learning, our relationships, and our leadership. You know, Jeff highlighted how many of us unknowingly fall into the trap of clumsy, sneaky, or attack questions. And that can obviously shut down dialogue instead of opening it up. Instead, he encouraged us to ask clear, direct, and honest questions. Ones that invite the full depth of another person's experience. By using quality question strategies like simply requesting reactions, we can avoid misinterpretations, defuse conflicts, and create richer conversations. Beyond just the questions we ask, we also explored the art of listening. Jeff emphasized that deep listening isn't passive, it's active engagement both with words and emotions. He shared the importance of follow-up questions and the skill of pulling threads to gain a deeper understanding. We also touched on the power of silence, giving people the space to fully express themselves, rather than rushing to fill the gaps. Now, one of my favorite takeaways was Jeff's concept of sifting and turning, processing information and emotions by identifying what truly matters and mentally turning it over to extract meaning.

[56:21] Thank you very much, Jeff.

[57:48] Reflection isn't just about the individual act, though. It's strengthened when we reconnect with the original source of our insights, closing the loop and deepening the relationships in the process. As Jeff so eloquently said, communication isn't just about speaking. It's about asking, listening, and reflecting with intention. Whether you're leading a team, strengthening personal relationships, or simply looking to grow, embracing curiosity, presence, and connections, well, that will set you apart from the competition. Well, folks, that was Jeff Wetzler. And again, he's the author of the brilliant book, Ask, Tap Into the Hidden Wisdom of People Around You. I highly recommend this book. It's filled with knowledge and experience and practical skills. And from someone who works with this all the time, I learned a lot. You'll find all the links in the show notes. Jeff, thank you very much for sharing your thoughts and your experience today. I had a brilliant conversation and I learned a lot. Well, folks, until Friday for Byte Size Fridays, well, a little homework, practice asking those questions with curiosity. And until we meet again, keep well, keep strong.

[59:01] Music.