Jeff Wetzler: The ASK Approach to Better Questions

Guy Kawasaki:
Maybe we shouldn't do this because I may disappoint you in real life.

Jeff Wetzler:
I have a feeling you're going to surpass the bar.

Guy Kawasaki:
Oh, he writes a pretty good book, but man, he sucks at asking questions.

Jeff Wetzler:
You're a professional question asker.

Guy Kawasaki:
Yeah, I'm not exactly a lucrative question asker.
This is Guy Kawasaki, and this is another episode of the Remarkable People podcast. We're on a mission to make you remarkable. And after reading the next guest's book, I figured out that if you can ask good questions, it's a very important skill for being remarkable. So the guest is Jeff Wetzler. Now, he's really a visionary leader in learning really and asking questions, and he has written a book called Ask, which I love one word titles. It's like, "What's the book about? Duh, it's Ask."
He has spent decades, although he doesn't look that old, helping organizations. He even had a stint at Teach for America, which I think is just a great idea, that kids after they graduate serve one or two years teaching other younger students.
So I want you to get ready to rethink about how you listen and you ask and you lead and work with those around you. So welcome to the Remarkable People podcast, Jeff.

Jeff Wetzler:
Thank you, Guy. It's so great to be with you.

Guy Kawasaki:
So let's start with a very easy question. And the easy question is, do you believe in the concept of this great white male, purple cow, black swan visionary who can intuit what people need or think what they before they even know it? Which is to say that are there some people in the world, maybe people like Steve Jobs or Elon Musk, who don't need to ask questions because they're so gifted?

Jeff Wetzler:
I do believe that there are people who can take in signals and process those signals in very interesting, insightful kinds of ways. And across the spectrum, I think Steve Jobs, Elon Musk, and other people have a lot of talent at doing that. Even they don't always get it right. And I think the rest of us are mere mortals, and for us mere mortals trying to guess, trying go on our intuition, the research shows is quite often pretty unreliable. We end up with the wrong conclusion.
And sometimes we end up with the wrong conclusion even or especially in relation to guessing what the people who are closest to us in our lives actually know and think and feel. Whether our longtime spouse or our business partner or our colleague, we get overconfident because we think, "I've known them for years, of course I know what they think," but we don't get it right.

Guy Kawasaki:
And why don't we get it right? Because you would think with the amount of exposure and the duration of exposure, we should be able to get it right.

Jeff Wetzler:
I think that at the simplest level, we don't get it right because we're not them, we're us. We see the world through our lens. They have their own experience. They are not a static person, they're changing all the time. There's really interesting research that shows that even the best advice that we often get for how to do this doesn't work.
So for instance, one piece of advice we often get is try to read their body language, if you can just read their body language. It turns out that people are not reliable readers of body language. Even trained TSA agents in the airport are barely better than chance, which doesn't give you a lot of confidence flying but it's true.
Another piece of common advice we get is try to put yourself in their shoes, but that doesn't work either. Literally, the research shows there's only one way that reliably allows mere mortals to find out what other people think and feel and know. Of course, that's to ask them, but it's so much easier said than done.

Guy Kawasaki:
Wait, but Jeff, you just blew a hole into a lot of business writing about you have to develop your skills of empathy. Are you saying empathy is overrated?

Jeff Wetzler:
No, I'm not at all saying empathy is overrated, but I am saying that untested assumptions about what's going on for people can be dangerous for us. So the idea of trying to imagine what they might go through I think is super valuable. If we say to ourselves, "I'm imagining it, and then what I'm imagining I'm 100 percent sure is right," that's what's dangerous.
We can imagine it to the point where we can actually have a conversation and ask them to tell us more about what you're going through and what's that like, and then we can of course connect emotionally. I think that is the kind of empathy that is deep and powerful and valid. But if it's just, "I'm guessing what you're going through, I feel empathy for you," it's risky.

Guy Kawasaki:
Is there a continuum where you have superficial empathy where you're guessing, the next level would be you actually watch people as they drive their minivan or as they open up a bottle of pills and they can't figure out how to open the bottle, and then the third level is when you actually are the customer, you are actually in the minivan, you actually open the bottle. So is that a spectrum that we can travel?

Jeff Wetzler:
I love that spectrum, and I think what I take from that is that the more information you have, the better your empathy is going to be. If you're the actual user, you've got all the information. If you're watching the user, you've got some of the information. If you're sitting at a distance, you have less information.
And so the more you can get to actually getting the information that's right, the more accurately you're going to actually have a chance of knowing what's going on for the other person. So I might borrow that little framework.

Guy Kawasaki:
Feel free to rip me off, I'll be flattered.

Jeff Wetzler:
I will credit you.

Guy Kawasaki:
In a rare moment of openness and transparency, I came across this concept from a friend named Martin Lindstrom. He wrote the book Buyology, B-U-Y, and he tells this story that he was retained by a pharmaceutical company because they wanted to get closer to the customer, which that's like a signal to McKinsey to charge them five million dollars.
But anyway, so he had all the executives come in a room and they said, "We want to get closer to our customers." So he made them breathe through straws for a few minutes and at the end he said, "Your customers have asthma. That's what it's like to have asthma." And I thought that was such a brilliant story. Now I use that in my speeches. I pass out straws in my speeches.

Jeff Wetzler:
I think I read that story in your book as well, and I literally took a straw, and I tried it myself because I wanted to know. I thought it was so brilliant, and it's really hard to breathe. And so I love that example.

Guy Kawasaki:
So now there's going to be a run on straws.

Jeff Wetzler:
That's right.

Guy Kawasaki:
But Jeff, why is it that people don't ask better questions?

Jeff Wetzler:
I think most of us just assume we know how to ask questions. We're born, we learn how to talk, most of us for a living talk. We make statements, we ask questions, we think we know it, so why would we even try to get better at it? I think that's a piece of it.
And I think the other piece of it is we often operate without the level of curiosity that we would truly need. We walk into situations, we size them up in split seconds, we don't even realize that we're sizing the situation up. We just think that's reality of the way it is.
And so if I think I know what's going on here, I know what your motive is, I know what the right answer is, I know what I'm trying to do here, why even bother asking a question? It would be illogical to even ask a question if I'm certain. And so we've got to figure out how to actually get ourselves more curious to open up the space for more questions.

Guy Kawasaki:
But couldn't you make a case that it's part of evolution that we had to make split-second questions?

Jeff Wetzler:
100 percent.

Guy Kawasaki:
If the saber-tooth is chasing you, you don't ask, "Are you trying to kill me or not?"

Jeff Wetzler:
I agree. Even today, let's say that you're in a room and you're starting to smell smoke, you don't think to yourself, "I wonder if someone's cooking, I wonder if whether," you just get the hell out of there or you just put out the fire.
And so this mechanism of walking into a situation that has a lot going on, zeroing in on what's the one thing, quickly making meaning of it, quickly drawing a conclusion, quickly saying, "What's the action I need to take," is a very adaptive thing for high urgency, emergency kinds of situations. I'm sure that's why it evolved in that way.
The problem is that much of the time we're in complex situations, we're in fast-moving situations, we're in ambiguous situations, where the first thing that we jump to may not be the right thing, but where somebody else might see something different. And if we still operate in that same, there's the tiger mode, that's when we get ourselves into trouble.

Guy Kawasaki:
So how can people learn to be curious then?

Jeff Wetzler:
Okay. So this is what I've been studying, and it's been just a fascinating journey. There's what I would call a few different gateways into curiosity. One of the most powerful gateways is to actually slow down our thinking so we can recognize the narrative that we've just drawn. So let's say that I'm walking into a situation, somebody says, "I really don't think we should make that change."
My saber-toothed tiger brain, my lizard brain might say, "They're being resistant. And the fact that they're being resistant is because they are trying to thwart me as a leader. And the fact that they're trying to thwart me as a leader means I need to get them off the team," just as an example. That process can happen in less than a second, outside of my own awareness.
But if I can begin to realize this is how our brains work, I'm starting to construct this story, I'm selecting a small bit of data, I'm making it mean something quickly, I can begin to inject what I call curiosity sparks into that story. I can say, "All right, what else might be going on here? What's another way to look at the situation? What might they be overlooking?" And that's essentially a way of loosening the grip that our story has on us. Not to say we're wrong, but to make room for more possibilities going on.

Guy Kawasaki:
But I would suspect that 99 percent of the people listening to this would say, "Yeah, that's true for most people, but not me. I am perceptive, I really know what to do."

Jeff Wetzler:
I would say if that's you, then you really need to learn, you really need to listen because every single one of us is human. We all have that evolution behind us, we all have to do that. And generally what I tend to say is, "If you're getting all the results you want in your life and in your work and in your relationships, maybe you don't change anything."
But chances are every single one of us has areas where we can actually be making better decisions, where we can prevent errors, where we can grow faster, we can deepen relationships, and that's the motivation to say, "What can I learn from this other person?"
I will say, it's not easy to do. Sometimes curiosity is a team sport. It can be helpful to say, and I say this to my own business partner a lot, "I'm really worked up about this person. I think this person's not being a team player. I think XYZ."
And he'll say to me, "Maybe take a little of your own curiosity, let's slow this down a little bit." And so sometimes we're so in our own story that we don't see it. So using colleagues, friends, mentors who are willing to challenge us a little can be a great way to make space for curiosity.
It also turns out I've discovered in writing the book, and increasingly so, that friend can be your favorite AI chatbot too. You can take your rant about your least favorite politician or your enemy or whatever, you just dump it in, and you say, "How could anyone like this person?" And then, you just right at the end, "What might I be missing?"
And in the privacy of your own desk, your office, your phone, whatever, you get back some very interesting considerations. Not to say that your story is 100 percent wrong, but to say, "Here's some other ways to understand what's going on." And those other ways of looking at it can give you some degrees of freedom to ask new questions to learn more things.

Guy Kawasaki:
Okay, I'm typing Elon Musk into ChatGPT right now.

Jeff Wetzler:
And add, "What might I be missing? What else? What's another way to look at this?"

Guy Kawasaki:
As soon as this recording is over, I'm going to do that.

Jeff Wetzler:
I want to know what it makes you think.

Guy Kawasaki:
All right, so now you built a case about slowing things down, using AI, getting your friends and colleagues to push back on you, but the next question is, who do we ask questions of, because there's a lot of people around me, how do I pick who to ask?

Jeff Wetzler:
Yeah. So first of all I'll say, a lot of people say to me, "It's great to ask questions but there's a lot of people that I have no interest in asking questions to. I have no need to ask them questions. I just completely disagree with what they have to say. I think that they're even dangerous."
And my contention is there is something important and interesting to learn from every single person. If you're talking to your enemy, someone that you actually think is quite dangerous, the thing you need to learn from them is what's their next move going to be so that you can figure out what to do about that move. If you're talking to someone that you deeply disagree with, the thing that you need to do is understand where did they get to their views, in case you want to influence them.
And it's a very well documented phenomenon in social science that you're actually more influential at influencing someone else if you know where they're coming from, if you demonstrate curiosity to them. They even perceive you as more reasonable, more likable, and more influential just by asking them questions.
So even if you don't care about learning from anything from anyone, just by asking them questions and learning, you're going to influence them better. But chances are there's going to be something in there that's also going to be interesting and important to you as well.

Guy Kawasaki:
So that's why you can learn something from an Uber driver with a flag.

Jeff Wetzler:
Exactly. You watched the TED Talk, I take it.

Guy Kawasaki:
I read your book.

Jeff Wetzler:
Or maybe read the epilogue of the book. It's in both. Yeah.

Guy Kawasaki:
You think this is the kind of podcast where the producer hands the Wikipedia entry to the podcaster and says, "Okay, have at it, bro."

Jeff Wetzler:
You did your homework.

Guy Kawasaki:
I did my homework, absolutely. So now, as the Japanese say, we have a word for this. As a maven, as a maven in asking questions, what do you think of polling, because talk about asking, polling is asking?

Jeff Wetzler:
I would say that anything is better than not asking. And so if you're doing a survey, if you're doing polling, that's good, that's better than the alternative. But it's only going to get you the surface level. It's going to get you, "I like this person, I don't like this person, I would buy this product again, I wouldn't buy this product again." That's really good to know, and you could start to do that.
But I would say to me the poll is just the door that you have to open and then you have to walk through the door. And walking through the door then requires I think a level of dialogue of like, "How come? Tell me the story why. What would make it better? What would have to be true for you to actually change?" So there's all kinds of deeper things that I think surveys and polls are less good at getting to, but they can be the opening for you to go deeper with someone.

Guy Kawasaki:
All right. So why don't you just give me the methodology for optimal asking? You gave us optimal curiosity. Just go down the Jeff Wetzler checklist for optimal asking.

Jeff Wetzler:
I will just give you at the high level of what I call “The Ask Approach.” This is the five strategies or the five steps that essentially gives you the greatest possible chance of finding out the things that other people think and feel and know that they are likely to not tell you otherwise, but that you might otherwise need to know. And we can talk more about that.
But at the highest level, number one I call choose curiosity, and we've been talking a bit about this. But basically nothing else I would say matters if you're not genuinely curious to learn from the other person.
It will just seem like a gimmick or a technique. It will not be authentic. On the other hand, if you're genuinely curious, if you really want to understand someone, you'll radiate an energy that they can tell you're interested, that makes them more likely to want to actually share with you. And I don't look at curiosity as a trait that some people lack and other people have. I look at it as a choice, as a decision that's always available to us. So we can talk more about that but that's number one, choose curiosity.
Number two is a recognition that let's say even I am wanting to learn from you, I am curious, if you don't feel safe to tell me your truth, especially if it's a hard truth, and this is where a lot of Amy Edmondson's research comes in, I'm not going to learn from you. I learned this the hard way as an operating leader.
You mentioned I was an executive at Teach for America. I came in from the business world and I figured if I have a question for someone, they're going to tell me. If they're struggling, they're going to let me know. And I quickly learned, especially as I was working across many different lines of difference, people were intimidated, they didn't actually feel safe.
And I'm thinking, "It's just me and I'm here to help." And they're thinking, "This guy could fire me. Why would I tell him the truth?" And we had some near collisions because of the people not telling me the actual truth. So make it safe is all about lowering those barriers, making it more comfortable, easy, and appealing for people to share with you their real truth, and we can get into what that looks like.
Number three is called pose quality questions. This is the heart of “The Ask Approach.” This is basically to say not everything that has a question mark is a quality question. My definition of a quality question is simply a question that really lets you learn something from someone else. And I distinguish between crummy questions versus quality questions.
And in the book, and we can talk more, I share a set of strategies. And it's not like there's fifty or one hundred. If you can learn maybe ten or a dozen strategies, you'll radically expand your repertoire of what you can actually learn from someone else. So that's posing quality questions.

Guy Kawasaki:
Wait, before you go on to number four, give me an example of a crummy question.

Jeff Wetzler:
Isn't that right? That's one of my favorite crummy questions because people will say something and they'll be like, they may genuinely want to know, do you agree with them? But when you say it like that, it makes it much harder, especially if they don't feel safe, to tell you.
I'll give you another one that I talk a lot about with groups. I did this yesterday. Just the question this, does that make sense? So you give someone some instruction or some explanation. You say, "Does that make sense?" And most people in the room say, "I ask that question all the time."
But it's a crummy question for a couple reasons. One is it can make someone feel stupid if they don't understand it. Two is when someone says, "Does that make sense," are they asking do you agree with them or do you understand what they say?
So if you ask, "Does that make sense," and someone nods, you have no idea if they're just nodding because they understand but they disagree, or the other way around. You can very easily redesign that question to make it higher quality by saying something like, "So what's your reaction to that? How does that land with you? What does that make you think? How does that sit with you?"
Any of those are questions that are much more likely to help you understand the other person's thinking about your own thinking. So if they disagree, if they see gaps, you're far more likely to be able to do that because it makes room for what this fancy term is, disconfirming data. It lets disconfirming data come into you so that you can then have a conversation about it.

Guy Kawasaki:
Hey Madisun, do I ever ask you if something makes sense?

Madisun Nuismer:
Yeah, sometimes.

Guy Kawasaki:
Oh, that's a lesson there. Be careful what you ask on a podcast recording but anyway.

Madisun Nuismer:
I do the same, though.

Jeff Wetzler:
I think it's so common, we all do. When I first learned to redesign that question to say, "What's your reaction," I was a new manager and I had just given somebody a set of instructions for what I was hoping that he would do. And I remembered to myself, "Just ask him." And so I said, "What are your reactions to that?"
And he got quiet for a minute and then he said, "If you really want to know my true reaction, I'm completely demoralized by what you just asked me today." And I was just like that, I was flabbergasted because I thought we were good. But what I discovered is he had a whole different set of information about what our clients needed and were asking for than I did.
And so what I asked him made no sense to him to do based on the information he had. Within the span of about five to seven minutes, we cleared it all up, we got back on the same page. But had I not taken literally the three seconds to ask the question, "What's your reaction to this," he would've either done the wrong thing or just not done it. He would've resented me. Our relationship would've suffered. We wouldn't have served the client well.

Guy Kawasaki:
Wow.

Jeff Wetzler:
And so people say, "I don't have time to ask questions." And I say, "It doesn't take long, just three seconds to ask a question, and you can save yourself weeks. And I think a lot of heartache and money too."

Guy Kawasaki:
I think that I will add to my Macintosh a keyboard macro, so I just type something like Z reaction, and it'll spit out the whole sentence, "What's your reaction?"

Jeff Wetzler:
I love that.

Guy Kawasaki:
I can ask that all the time. Okay, Madisun, get ready to always tell me your reaction.

Madisun Nuismer:
I'm ready.

Jeff Wetzler:
Sorry, Madisun.

Guy Kawasaki:
Okay, so I think we're on number four, though.

Jeff Wetzler:
Yeah. Number four is called listen to learn. And basically once you ask a question, it all comes down to do you hear the answer? How well do you actually listen to what someone has to say? And a lot of times we're listening to look smart, listening to prove a point, listening to get someone to do something, listening to look like we're listening.
None of that is listening to learn. Listening to learn is truly taking a vigorous interest in what someone else has to say so that you can actually get to the essence of what they're talking about. It's listening not just for the information, but also for the emotions and also for the actions.
And when I talk to groups, I say to them, I say to people, "Give me on average what percent of people that you talk to you think is a good listener." On average, people say it's about 10 percent or 15 percent of people, but many polls think that the vast majority of us think we're good listeners.
So there's a massive gap between how good we think we are as a listener versus how we're actually experienced as a listener. But there's some very simple things that we can do to increase our listening. Should I give you an example or two?

Guy Kawasaki:
That's why I have you on the podcast.

Jeff Wetzler:
All right, I'll go there.

Guy Kawasaki:
That makes sense to me.

Jeff Wetzler:
So for the book, I interviewed professional listeners, including journalists and also including psychotherapists. Psychotherapists sit there and they listen all day long. And one of the things I discovered is that psychotherapists universally experience this phenomenon called the doorknob moment. Have you heard of this?

Guy Kawasaki:
No.

Jeff Wetzler:
So if there's a session that is fifty minutes long, what happens quite often is that someone will sit there and have the therapy, have the conversation, and then at the very last second, at minute forty-nine and fifty-nine seconds, right when they're standing up, their hand is on the door, they're about to leave the room, only then is when they actually say the real thing that's going on. That's when they say, "I'm thinking about leaving my spouse," or whatever the thing is that's going on.
And these therapists, they're like, "Why didn't they tell me this during the whole session? We could have talked about it." And they have all kinds of theories. Sometimes they think, well, maybe they were working up the courage or maybe they were waiting to see how I reacted. Or maybe they were just getting their thoughts straight. One of them recently said to me, "I think they do it because they want me to think about them all week. So they just say it as the last thing, hoping that I'll think about it."
But the takeaway is that you can't assume that when you ask a question and someone answers it, you're getting the most important thing they have to say. Often the most important thing they have to say is two or three layers back. And it's not the thing that comes out when you ask them. And yet many of us will ask a question and then we'll say, "Okay, I got my answer. Now, next question." Or, "I'm moving on." And we miss the actual real thing.
So there's a listening technique that I just call pull the thread, which is if you just pull it a little bit more and say, "That's interesting, can you elaborate on that? Can you say a little bit more about that? Tell me more. What else?" Any of those things are just ways to increase the likelihood that the real thing is going to come out when you ask someone the question.
Sometimes I will even say to my own team, if we're having a conversation or I'm asking them for ideas, I'll say, "What else? And what else?" And then I'll even say to them, "I'm going to keep asking you what else until you tell me that's it. Because the ideas keep getting better and better each time I say, what else?" That's one of the strategies, pull the thread.

Guy Kawasaki:
And what happens if you pull the thread at the fiftieth minute or the fifty-ninth minute?

Jeff Wetzler:
If you're in a psychotherapy session, you can't because it's over. And so that's the thing, is by not doing that, they've missed the chance. But we don't have that constraint usually. Usually we're still in the conversation. We can continue to do that in a conversation. So that's one.
The other one I would just share with you that I would say is if there's nothing else that anybody who listens to this episode remembers, this entire episode, it would be this thing. It's just called tell back and test. And so when you're talking to someone and they answer your questions, before you give your response or before you ask the next question, just simply say, "I think this is what I heard you say. Let me just check, did I get that?"
Or "Here's what I think I'm getting from you. How close is that?" Whatever it is. It's very rare that we do it, but research shows that it is actually one of the biggest distinguishers of high performing teams versus low performing teams, the degree to which they just check if they understood what each other said.
It's sort of the magic move. It has many benefits. The first and most important, of course, is simply you get better information. So when I do this, half the time when I say to someone, "Let me just check, I think this is what you're saying, is that right," they will say, "Kind of, but that's not exactly what I meant." Or, "That is what I said, but now that you tell me, this is what I really think." I just get better information. It saves a lot of time.
It also just changes up the tempo of the conversation. So let's say we're having some kind of an argument or whatever, it's like a ping pong match or a point/counterpoint. If I just stop and say, "Before I react to you, Guy, I just want to check if I understood where you're coming from. Is this what you mean? Is this what you're saying?" It just slows it down. It gives us a chance both to breathe.
But I think the most important benefit is that it also sends you the message, I care about you. I care about you enough to take my own time, my own words, my own breath to check if I understand where you're coming from, what's important to you. And that changes everything as well. So the magic move, the power move. Just check your understanding, tell back and test.

Guy Kawasaki:
Man. I don't know if I can get to number five.

Jeff Wetzler:
Number five, I'll tell you, is my favorite of them all. And the reason why it's my favorite is because it's called reflect and reconnect. And as you said at the beginning in your kind introduction, my passion in life is learning. And I believe that reflection is how we learn.
Reflection is how we convert our experiences into takeaways or insights and our insights into actions. I think reflection is the difference between somebody having twenty years of experience doing something versus having one year of experience twenty times over. It's how well they reflect.
And I think that reflection often gets a bad rap. People think, "I don't know how to reflect. I don't have time to go on a meditation retreat. I would have to start, whatever, going into the hills." But reflection can be very simple. So I have a method I suggest that I just call sift it and turn it.
Sift it is just to say, let's say someone told you thirty things in the course of a conversation. Just sift it and take a second. What were the three or four most important things I took away from that person? And I can release some of the other stuff.
In fact, some of the stuff that people tell us, we don't need to take it, maybe it's not even healthy for us to take it. So sift it. And often it can be helpful to sift it with a friend or a colleague so you're not sifting out the wrong stuff, and then just turn it over in your mind three times.
The first time I would say is turning it over to see how does this affect my story about the situation? Maybe it gives me a new piece of information, maybe it shows me a wrong assumption I was making or whatever it is. How does it affect my story? The second time you turn it is to say, based on that, what steps should I take? Maybe I want to apologize, maybe I want to double down. Maybe I want to make a right turn with it.
But just ask yourself. And then the third is the deepest turn, which is there that I learned here that affects my own stuff? Maybe it revealed to me that I have a bias or a way of being or some deeper held assumption that this just kind of questioned a little bit. So sift it and turn it for your story, your steps, and your stuff.
And then the reconnect part is the closing the loop. It's basically to say this whole “The Ask Approach” is not just about me taking things away from myself, it's about connecting back to the other person and saying, "Thank you for taking the time. Thank you for taking the risk if it felt risky, and by the way, here's what I learned from you and here's what I'm going to go do with what I learned from you. And is there something different than you were hoping or additional you were hoping I would learn from you?"
And that act of closing the loop, I was just literally with a group of executives yesterday and they said, "Our whole organization is cynical because we ask them for so many suggestions and then they have no idea what we do with these suggestions. And so they say, what's the point?" But closing the loop lets people know they didn't waste their time, they're powerful because they've influenced you, and I think it just deepens the connections so that they're going to want to share and you're going to want to share more together over time.

Guy Kawasaki:
I'm exhausted already. You're changing my entire conversational style. My God.

Jeff Wetzler:
Well there, you know what, you just reflected, you reconnected back to me. You told me something, some impact that it had on you.

Guy Kawasaki:
Can I ask you, do you value, even if it's performative, people taking notes?

Jeff Wetzler:
I think that whatever people need to do to make sure they get the right takeaways is valuable. Nowadays, more often I am using an AI note taker, whether it's on my phone, if it's in person or online. If it's on Zoom, I can use any number of them. And for me, that's a way that I can actually just fully stay present with the person but know that I'm going to still have the takeaways.
But if someone doesn't have that or if that's their style, I think that's great, as long as they're not so buried in their notes that they're not able to make some eye contact and look across sometimes. But if it helps you to make sure you're getting the right takeaways, I think that can be valuable.

Guy Kawasaki:
So are you saying that I could take a transcript of a conversation, put it into an LLM, and ask it, "What are the takeaways? How should I reconnect?" I can use it as a coach.

Jeff Wetzler:
You can do that. In fact, there's some really fun things you can do. For example, you can take that transcript, you can say to AI, "What are some questions I didn't ask in this conversation that I might've asked?" Or, "What are a few follow-up questions that I can ask in my follow-up email or in the next question?" So it can actually help you generate questions.
But the other really fun thing that you can do with the transcripts to help you practice listening, I mentioned very briefly earlier that you can listen for content, emotion, and action. So content is the information that someone's saying. Emotion is what are the feelings that they were expressing or displaying? And actions are what are the behaviors that they were doing in the conversation? You can literally take a transcript and ask it to help you listen for those three things.
So you can say at a content level, what were the most important facts and arguments that were being made? At an emotion level, what were they expressing and displaying? At an action level, what behaviors were they doing in that conversation? And you can check it against your own listening to that.
And in a way, it can really help you to train your brain to not just listen. Because most of us just listen through one of those three channels. For me, I default to content and I can sometimes miss the emotion or the action. But if I can do that, I can start to train my brain to be listening for those other two things too.

Guy Kawasaki:
Let's get a little more granular here. So are there differences when you're talking to women versus men? Are there differences when you're talking to old versus young? The five things are generic across all human beings, but do you have to change things up for old, young, gender, stuff like that?

Jeff Wetzler:
I will say I do believe that they are generalizably applicable, but there is some interesting research about the ways in which lines of difference can exacerbate some of the challenges that “The Ask Approach” is trying to solve. So the biggest problem that “The Ask Approach” is trying to deal with is people not telling us the real truth, is people actually knowing and feeling and thinking things. They don't have to be any bad things, they could be ideas too, but just not telling us.
There is a phenomenon called “protective hesitation” that someone named David Thomas, who was a researcher at Harvard Business School, is now the president of Morehouse College, he coined the term, and it basically refers to the idea that women and people of color are less likely to get honest direct developmental feedback than other people because their colleagues, their bosses, and mentors are engaging in this “protective hesitation,” which means that they are both trying to protect the women and people of color from getting feedback or input that might be biased or that might perpetuate some kind of oppression, but they're also protecting themselves from getting accused of that as well.
And so for both of those reasons, they're not learning as much. And so that can be especially important situation in which to be using some of these ask methods.
And then the other thing that is well documented is that psychological safety can go down across any lines of difference, whether that's a cultural difference, power difference, gender difference, race difference, et cetera. And so those are the ways in which I would say that dynamics of difference play into this.

Guy Kawasaki:
Are there telltale signs? I'm listening to this, I'm using I generally, people are listening to this and they're saying, "Can you just give me some tells that obviously I should figure out that I am a lousy question asker. How can I self-diagnose?"

Jeff Wetzler:
Definitely, there's a few. I would say if you look at any conversation, you could take a transcript from AI or you could just listen to a conversation, and you could literally plot out the ratio between two things, statements and questions. You can divide everything into statements and questions, and you can look at the ratio of statements to questions in a conversation.
If your ratio is a lot of statements and very few questions, overall you are a lousy asker because you're just not asking many people that question. Now, of course, if you're being interviewed or if you're giving a lecture, then that's one thing. But generally speaking in conversations, if your ratio is very heavily tilted towards statements and very low towards questions, you're off.

Guy Kawasaki:
I will tell you that at least mentally I try to achieve a ratio of my talk to the guest talk at ninety to ten, ninety to ten being 90 percent Jeff, 10 percent me in my podcast.

Jeff Wetzler:
I've seen that in your episodes, yeah. And I think the way that you get that done is by asking questions. And so if your ratio is flipped the other way or if your ratio of statements to questions is the other, you've got some improvement to do. I would say that's one. I'll just give you two others.
If you're a leader and you're not getting critical feedback from the people around you, chances are you're not asking the right questions or you're not asking the right questions in the right ways because the people around you undoubtedly have observations and feedback and ideas of what you could be doing better. So if you're not hearing that, that's something that you should take notice of.
And then the third thing I'll just say is if your questions generally start with words like do or don't, would or wouldn't, is or isn't, chances are you're going to be getting surface level answers because you're getting yes/no answers, versus if your questions are starting with, how come, those are going to be open, they're going to give you richer information.

Guy Kawasaki:
So if I'm a manager, can I paraphrase what you just said, which is to say that no news is bad news.

Jeff Wetzler:
I love this. Yeah, you're a fast learner. No news is bad news. And by the way, that's not just true if you're a manager, that's also true, let's say if you have any kind of professional service. If you've got clients and your client is not giving you critical feedback, if you're a startup founder and your investors are not giving you critical feedback, it really goes 360 degrees around. If you're only getting affirming feedback, chances are you're not asking the right questions in the right ways.

Guy Kawasaki:
You heard Madisun say it, that I often ask her if something made sense.

Jeff Wetzler:
But I also heard that you have a relationship with Madisun because I observed it, where she's also willing to tell you a little bit more, and I think that's probably healthy.

Guy Kawasaki:
There is no question that Madisun is willing to tell me negative things. Yes.

Jeff Wetzler:
That's the real deal. So you're doing something right.

Guy Kawasaki:
Much of our discussion has been focusing on asking the right question. So now we also have to answer the question. So how do I optimize my answers?

Jeff Wetzler:
I would say to optimize your answers, you want to be speaking directly to the question as opposed to speaking around the question. If you receive what I call a crummy question, so let's say someone just asks you a surface level, "Do you believe X or Y," or whatever, sometimes you can go further than just giving the surface answer. And sometimes you can also say to them, "This is my simple answer, but is there a deeper part of your question?" Or, "Is there a question behind the question?"
Sometimes people will ask you questions that are really them trying to get you to agree with them, and then you can say, "I'll share my thoughts, but I'm curious. It sounds like you might have a view on this. What are your views on these questions?" And so I often say to people from the perspective of answering, even if someone doesn't come at you with a quality question, you can help make their question better in those kinds of ways. And that will get a better answer out of you too.

Guy Kawasaki:
Is there a Jeff Wetzler Hall of Fame that you say, this person really knows how to ask questions? It could be a journalist, it could be a broadcaster, it could be a CEO, it could be, I don't know, Oprah Winfrey. Do you have a Hall of Fame?

Jeff Wetzler:
I have different people in different categories. So for the book, one category was CEOs, and I tried to interview iconic CEOs. And the reason I did is because CEOs are notorious for getting lied to. People tend to tell CEOs what they think the CEO wants to hear, what they think is going to make themselves look good, what they think is going to get their agenda through.
And so I said to CEOs, and this included people like Bill George of Medtronic or Irene Rosenfeld, who ran Kraft for a while, I said to them, "How did you get the truth out of people, especially several layers away from you?" And I'll never forget, there was one common theme. They basically said, "If I want to get the truth out of someone, especially someone junior, I'm never going to bring them to my office and make them sit across the intimidating CEO desk from me and assume that they're going to tell me the truth."
Irene Rosenfeld from Kraft basically said, "I'm going to go to the cafeteria. We're going to have lunch together." Bill George said, "I'm going to do a ride along and we're going to take a walk," whatever it is.
And there was no single answer other than what makes them feel safest, what makes them feel the most comfortable? And so it was so interesting to me, and this is why I would name both of them as heroes. For example, it's not even about the questions yet. It's about the setting that they create, the safety that they create for people to then open up.
And when you have that right tone and that right setting for connection, it takes a little pressure off of, do you have the perfectly worded question? Because you've got the level of safety there. And I know you have kids. I have a teenage daughter, and I find that this applies to my relationship with my daughter as well.
When she comes home from school and I say to her, "How was school?" I get stonewalled. I get absolutely nothing. When I say to her at dinner, "What did you learn today?" Nothing. If I want to actually get the truth out of my daughter, I have to stay up until eleven in the evening when she's done with her homework and she's done talking to her friends and she wants to hang out with me in her room, and at that hour my body wishes that I was asleep, but if I want something from her, that's the setting.
And so that's what I learned, actually, from these question heroes is that it's about the other person and you've got to go to where they feel most comfortable and then you're going to learn what you want to learn.

Guy Kawasaki:
Okay, so that's the category of CEO, but how about the category of journalist or TV personality?

Jeff Wetzler:
Yeah, so in the category of journalists, I'll name two heroes here. One is Jenny Anderson. She's an award-winning business journalist. She actually also just wrote a great book that came out. And what she said to me is that when she does an interview, she usually asks the person that she's interviewing for permission to record the interview, and then she will go back and listen to the recording and she'll listen to it two or three or four times, literally the same recording.
And she said, "Every single time I listen to it, I hear something completely different than I heard the first time." And I think to myself, she is a professional listener and she's not getting the most important stuff the first time? It takes her two or three or four times. The rest of us barely ever do that. We just have our conversation and we move on. But to me, she's a hero for just recognizing the limits of her listening and all of our listening, and to go back.
And then the other journalist I'll just mention is Amanda Ripley. She recently came out with a book called High Conflict, which is a great book.
And what I learned from her, the way that she creates safety when she does journalism stories with people who have different backgrounds than her, she'll basically say, "Look, I know I'm from the East Coast. I know my life is different than yours in many different things. I'm truly ignorant, and I would love for you to help me to understand what I might be missing." And so she just confesses that in a way that's completely disarming to people and also creates that safety as well.

Guy Kawasaki:
Okay, so now the last category I'm going to ask you is about politicians. Is there any politician you respect for asking questions?

Jeff Wetzler:
I don't know if you know who Deval Patrick is. He was the governor of Massachusetts a couple of terms ago, and one of the things that he truly did well is that he would just spend a ton of time going all around the state, having conversations with people, listening to people, asking them, "What's on your mind?" And I think it really informed his policies in a much more grounded kind of way.

Guy Kawasaki:
That's a short list of politicians.

Jeff Wetzler:
It doesn't get a lot longer on that category, although I'm sure that there are many that I'm not aware of too.

Guy Kawasaki:
Yeah, I'm sure.

Jeff Wetzler:
Do you have any favorites on your end that you think are role models of great questions or listening, whether politicians or any other categories?

Guy Kawasaki:
Jeff, I'm from Silicon Valley. In Silicon Valley, we don't have to ask questions because we're omniscient and omnipotent. Have you not learned that?

Jeff Wetzler:
Oh, that's true. I completely forgot.

Guy Kawasaki:
Think of my history. I worked for Apple.

Jeff Wetzler:
Okay, enough said.

Guy Kawasaki:
End of discussion. Did that make sense?

Jeff Wetzler:
Perfect sense.

Guy Kawasaki:
All right, so three more questions. First of all, because I know in your book, the whole book is about asking questions, but at the end you drove it home by asking about mastery. So question number one is how do you master asking questions?

Jeff Wetzler:
Yeah, I would say that the way that you master it is really no different than how you would master any other important skill. And it starts with recognizing the limits of where you are right now, recognizing where you might not be as good at it. So for example, paying attention to what is my ratio of questions to statements. And if I start to see that ratio is off, then I get a little insight.
Or starting to actually look at or audit the kinds of questions that I'm asking. And in the book that we see high quality questions versus crummy questions, I start to see that I'm asking crummier questions. So some of it just starts with awareness, and the fancy term for that is conscious incompetence. It's recognizing, is becoming more conscious of the ways that I'm incompetent in this.
And then the thing to do is just to start to pick it off little by little. So maybe you want to start by learning how to better ask for people's reactions, instead of saying, "Does that make sense?" You just start to force yourself to say that. You might even write it down on a card and have that card in front of you. You might even tell other people, "Hey, I'm trying a new kind of question." And then you practice that enough times that you start to see how to make it your own, and then it starts to become fluid.
Then maybe you want to go to the next cycle and you say, "All right, now I'm going to try to become a little better listener. Let me start by practicing pulling the thread." And you just do that over and over again for each of the different chunks that you want to do, and that's how you start to build your repertoire.
And then what I say is you've got to level up. It's one thing to do that in low stakes situations. Then you say, "What's the next higher stakes situation I can do that in?" And you don't start in the high stakes situations, but once you've gotten better, you try that again and again and again. And that's how it starts to become more of a superpower.

Guy Kawasaki:
And that's when I'm consciously competent.

Jeff Wetzler:
That's right. And you want to get to the place where you're unconsciously competent, to the point where you don't even have to think about it anymore. It just comes naturally to you because it's built into your repertoire.

Guy Kawasaki:
And are we getting Malcolm Gladwell? It's like 10,000 hours of this.

Jeff Wetzler:
Yes, but it has to be 10,000 hours of actually the right practice. It's not just 10,000 hours of practice, it's 10,000 hours of practice, watching how it went, feedback, tweaking it, adjusting it, leveling up, and those kinds of things.

Guy Kawasaki:
I have surfed for about 10,000 hours and I'm not getting any better.

Jeff Wetzler:
I have a feeling you're probably a lot better than when you started, though.

Guy Kawasaki:
That's not hard to say, but yeah. Okay, so how do I teach other people to become masters of asking questions?

Jeff Wetzler:
Yeah. So the easy answer is the best way to teach it is to role model it yourself. So the more that, if you're a leader, the more that the people on your team are seeing you admit that you don't know something, ask a follow-up question, shut up and listen, instead of just taking over the meeting and telling them what to do, any number of those things, that sends a super powerful message to people about what you value. They will imitate your behavior.
You can also, of course, actually put people in situations where they're being taught this kind of stuff as well. You can call people out to reward that. So not just rewarding, hey, you hit your sales goals, but also, hey, you asked the best question that we haven't thought about yet. That pushed our thinking. And so what you actually elevate, you can even hire for it.
I remember in my first job out of college, I worked for a company called Monitor Group that literally was hiring for a proclivity to do this stuff. And after they made me do a whole performance task and presentation in front of a group of people, somebody sat me down and they gave me a bunch of critical feedback, and I thought they were giving me this feedback to tell me why they were about to not give me the job. And I said, "So does that mean I don't get the job?"
But really what they were trying to do is they were trying to see was I going to be defensive or curious about the feedback? Was I going to try to push back on it or was I going to say, "That's interesting, how come? And tell me more." And so you can literally build this into your hiring practices too.

Guy Kawasaki:
All right. And the final and most important question about master is how do I help my kids become master question askers?

Jeff Wetzler:
Yes.

Guy Kawasaki:
Maybe we should interview your daughter.

Jeff Wetzler:
You could interview my daughter or my son who is actually now working out at Silicon Valley as well. But well, first of all, the thing to say is that kids are born curious and by age four they're asking between twenty-five and fifty questions per hour. And parents of young kids nod, and they say, "Absolutely, that's what they're doing." What's fascinating is that those same exact kids in school ask two questions per hour.
And so there's something very different going on when they're not constrained. I think it's because schools basically have a model where we tell kids, sit down and shut up and give me the right answer. Stop asking so many questions. And I was talking to a group two weeks ago and somebody said to me, "When I was a kid, my parents were so sick of my questions, they offered to buy me an ice cream cone if I would stop asking so many questions."
So the thing I would say to parents if you want curious kids is don't beat the curiosity out of them. When they ask the questions, take the questions, give them honest answers to those questions, admit to them when you don't know the answer to the question and say, "That's really interesting. Let's go find out together. What could that be?"
The way in which you respond to their questions will send a lot of messages. One of the exercises I do with groups is I say to people, "Stand up if as a kid someone discouraged you from asking a question." Yesterday 80 percent of the people in the room stood up. Usually it's about half the room. But just the amount of things that we do to tell kids, "Stop asking questions," to me is tragic. And so if you're a parent and you want your kids to be curious, encourage those questions, fuel that fire.

Guy Kawasaki:
I have to say, Jeff, that we have interviewed about 260 people and probably this episode, I feel the most convicted in doing things wrong.

Jeff Wetzler:
I feel like I owe you an apology.

Guy Kawasaki:
I look at this as a turning point opportunity.

Jeff Wetzler:
Well, I appreciate your learning spirit for the whole thing as well, and especially because I've learned so much from you and your book and your episodes over time.

Guy Kawasaki:
I hope I didn't shatter any delusions you had about my competence by coming on my podcast.

Jeff Wetzler:
Not at all.

Guy Kawasaki:
All right, Jeff, thank you so much for being on Remarkable People. I'm serious. I've got a lot of thinking to do after this episode. From now on when I meet people, Jeff, I'm going to say, "Hi, my name is Guy Kawasaki. What's your name?" And they're going to say, and then my next question is going to be, "What's your reaction?"

Jeff Wetzler:
What's your reaction to that? Thank you for having me on for such a great conversation and also for listening so seriously and taking it all in as well. It means a lot.

Guy Kawasaki:
And everybody out there, if you want to be a better manager, leader, or parent, you definitely need to pick up this book. It's called Ask by Jeff Wetzler. So thank you for being on this podcast, Jeff, obviously.

Jeff Wetzler:
Thank you.

Guy Kawasaki:
Thank you, Madisun, for dealing with my incompetence as a question asker, and thank you Tessa Nuismer for the research you did on Jeff, and also to the sound design team, which is going to turn this into just a great sounding podcast. That's Jeff Sieh and Shannon Hernandez. So that's it. That's today's episode of Remarkable People, and until next time, ask better questions.