Episode 203 –Tap into Hidden Wisdom – How to Ask Better Questions

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39 Minutes
Home Manage This Podcast Episode 203 –Tap into Hidden Wisdom – How to Ask Better Questions

About This Episode

Jeff Wetzler

Is asking effective questions a natural talent, or can it be developed? Why do some questions succeed while others fail to elicit meaningful responses? In this episode, we explore the art of effective questioning with Jeff Wetzler, author of “Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life.” Jeff argues that asking effective questions is a skill that can be developed and offers practical advice for improvement.

Jeff explains how to examine the motivations behind why people withhold information and the barriers to sharing their thoughts and experiences. He emphasizes the significance of discerning between what we say and what we actually think. Join us as Jeff introduces his “Ask Approach,” a five-step method designed to enhance anyone’s questioning skills. As he walks us through each step, he provides practical examples and tips that anyone looking to improve their questioning techniques can apply in their daily interactions.

Jeff Wetzler is co-founder and co-CEO of Transcend; previously, he was Chief Learning Officer at Teach for America and a management consultant at Monitor Group. He holds a doctorate in Adult Learning and Leadership from Columbia University. Jeff has been on a quest to transform learning opportunities. By the end of this episode, you’ll gain a better understanding of how to ask questions that unlock deeper insights and foster more meaningful conversations.

Favorite Quotes from Episode

"…we don’t realize there’s something that we need to know.  We’re not curious.  We walk around the world thinking that we’ve got it figured out, thinking that we know how this person is and what motivates them and what the right answer is in this situation.  And so, we’re trapped in what I call a “certainty loop,” where the pre-existing beliefs and assumptions we have about the world lead us to walk into any situation and just size it up in ways that essentially reinforce what we already thought and believed.  And we get that sense of, “Here we go again.  This is how they always are.”  And so all of that keeps us stuck.  And we don’t even realize there’s something to ask about."

Jeff Wetzler

"I’m positing that curiosity is a choice.  It’s a decision that is always available to us at any point in time.  And when we make that decision to choose curiosity, we’re centering a question at the front of our minds anytime we’re interacting with a person or a team. And that question is what can I learn from this person?  And it starts with the premise there is always something we can learn from somebody."

Jeff Wetzler

The podcast by project managers for project managers. This episode explores the art of asking effective questions. Author Jeff Wetzler offers practical advice for improving our skill at asking effective questions. The “Ask Approach” is Jeff’s five-step method designed to enhance anyone’s questioning skills, and he walks us through each step and presents questioning techniques we can all apply.

Table of Contents

02:43 … Motivation for Ask
03:56 … Why People Withhold Information
05:17 … Barriers to Sharing
07:40 … What We Say vs. What We Think
09:53 … What People Withhold
12:00 … Asking Superpowers
14:17 … The Ask Approach
16:00 … 1. Choose Curiosity
18:58 … 2. The Safety Cycle
19:32 … 2.1 Creating Connection
20:43 … 2.2 Open up First
21:09 … 2.3 Radiate Resilience
22:37 … 3. Pose Quality Questions
24:41 … Using a “Why” Question
26:23 … Clear up Confusion
28:13 … 4. Listen to Learn
31:31… 5. Reflect and Reconnect
35:39 … How AI Can Help
36:53 … Connect with Jeff
38:25 … Closing

JEFF WETZLER:  …we don’t realize there’s something that we need to know.  We’re not curious.  We walk around the world thinking that we’ve got it figured out, thinking that we know how this person is and what motivates them and what the right answer is in this situation.  And so, we’re trapped in what I call a “certainty loop,” where the pre-existing beliefs and assumptions we have about the world lead us to walk into any situation and just size it up in ways that essentially reinforce what we already thought and believed.  And we get that sense of, “Here we go again.  This is how they always are.”  And so all of that keeps us stuck.  And we don’t even realize there’s something to ask about. 

WENDY GROUNDS:  Welcome to Manage This, the podcast by project managers for project managers.  I’m Wendy Grounds, and with me in the studio is Bill Yates.  We like to talk to you twice a month to talk about what matters to you as a professional in the field of project management.  And we like to bring top experts to speak to you.

And today we have someone.  His name is Jeff Wetzler.  He’s written a book called “Ask:  Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life.”  And when Jeff sent the book to us, Bill and I both read it and were completely impressed.  And we thought, now, this is something we can talk to project managers about.

Jeff has been on a quarter century quest to transform learning opportunities.  He blends a unique set of leadership experiences in the field of business and education.  And he’s been a management consultant to the world’s top corporations, and the Chief Learning Officer at Teach for America.  Most recently he’s a co-CEO of Transcend, an innovation organization.

BILL YATES:  We have so much to learn from this book and from Jeff’s input or description of it.  For project managers, we ask questions all the time.  And quite frankly, some of us are good at it, and some of us are not.  Some of us are growing in this area, and this is an opportunity to take a conversation with a guy who’s written a book and researched how to ask questions that are effective, that are not throwaway questions, that go deep, that remove some of the barriers that people have to actually sharing what they’re feeling, what they’re thinking, what their experiences have shown them. 

And what I love about it is he’s got a five-step approach.  I love a five-step approach, and he has that.  He lays that out for us.  And we’re going to walk through it with Jeff so we can understand how can we get better at asking questions that are effective.

WENDY GROUNDS:  Hey, Jeff.  Welcome to Manage This.  Thank you for joining us.

JEFF WETZLER:  Oh, it’s so great to be with you.

WENDY GROUNDS:  We are going to ask you a lot of questions.  We’re just going to pick up from the [crosstalk].

JEFF WETZLER:  I love it.  I love questions.

Motivation for Ask

WENDY GROUNDS:  We’re going to start straight away. Can you tell us what is your motivation for this book?  What drives you to be so interested in asking questions, and the right ones?

JEFF WETZLER:  Yeah, the biggest motivation that I have in life in general, and it has been the through-line throughout my entire career, is learning.  I love to learn; but I’m also, I’m a junkie for helping other people learn, as well, too.  I really care about building learning experiences that are powerful and deep and sticky and enduring.  And I’ve done that in the business world, in the education space.  I tend to toggle back and forth.  From my perspective, when somebody’s not telling us something, especially something important, that is a missed learning opportunity.  Given who I am and what motivates me, I think that missed learning opportunities are almost like micro tragedies, especially when we could have done something about it.

And so, my motivation is twofold.  One is I think that this problem is painful and pervasive, but also there’s something we can do about it.  And given that I have been fortunate enough to be able to learn a set of ideas and tools and concepts, I wanted to pay it forward so that more people can avoid this missed learning opportunity and, on the plus side, can actually benefit from tapping into the incredible wisdom all around them.

Why People Withhold Information

WENDY GROUNDS: What motivates people to withhold information?  Like we’re going to ask them questions, but sometimes they’re not giving us anything.  What keeps people from sharing?

JEFF WETZLER:  Yeah, so many different things.  And in fact, the withholding of information is so common in life and in organizations.  I found this and experienced it and suffered from it when I was a manager in my first operating role and, you know, continue to do at times right now.  And in my research for the book, I just read how prevalent, I mean, in some studies people are saying upwards of 80% of people have said, “There’s something important I’m not telling my manager that’s a concern.”  And by the way, three quarters of the people around me also are concerned about it, and they’re not saying anything, either.  I even found a study about – people withhold from their own doctors.  Somewhere between 60 and 80% of Americans surveyed said they don’t tell their doctor something important about their own health, as well.

And to your question, why?  Why don’t they do that?  Some of the reasons that they gave in this particular study were, one, I don’t want to burden the doctor.  I don’t want to waste their time.  I don’t want to be embarrassed.  And I don’t want to be judged by the doctor.  And, you know, think about this.  If we are not telling our own doctor information that could make us healthier, maybe could even save our lives, how much else are we not telling that might even be less consequential than that?

Barriers to Sharing

And so, in the research for the book, there were several big barriers that emerged to people sharing what they really think, feel, and know.  The biggest one was a fear of the impact, the impact of what would happen if I actually tell people.  So maybe they think we’re going to judge them if they tell us.  Maybe they think it’s going to expose themselves.  And maybe they think it’s going to hurt us.  Maybe they think it’s going to put tension in our relationship.  All of those are examples of the impact that people fear.  So that’s one of the big barriers.

Another big barrier is people feeling like they don’t have time to bring it up or to say it.  You know, if I tell you what I really think, then we’re going to have to have a conversation about it.  And I’m already overworked, and I’m already exhausted, and I’m already burdened.  And why do I want to take that on?  That’s another reason.  Another one, you know, is sometimes people just can’t find the words.  They don’t have the words to say it.  Maybe they’re thinking something that they know, if they say it the way they’re thinking it, is not going to go well.  And they don’t know how to say it more constructively.

Interestingly, sometimes not having the words is just a mathematical thing.  One of the pieces of research that was most fascinating I found is that the human mind can think at 900 words per minute, but the mouth can only get out 125 words a minute.  So that means when I’m talking to someone, I’m hearing less than 15% of what they’re actually thinking just because the math doesn’t work.

But the most important reason to me, the most interesting reason why people don’t tell us is that they don’t realize we care.  They don’t realize we’re interested.  And so, if they’re thinking, well, Jeff’s not interested, or they’re not sure if I’m interested, why bother trying?  Why bother telling him?

BILL YATES:  Mm-hmm.  Man, those are big barriers.  One of the ones that you mentioned I can really relate to, which is I’m afraid of how this is going to land.


BILL YATES:  If I share 100%, I’m not sure how it’s going to land on the person that’s going to hear this.  You know, am I going to hurt their feelings, or am I going to jeopardize the relationship somehow, or make them look bad in front of their manager or their team or whatever?  So sometimes that keeps me from being transparent.  And then later, inevitably, later I’ll regret it, say, “Oh, I should have brought that up two weeks ago.”  You know, now we’re having this conversation, and it’s not fresh.

JEFF WETZLER:  Right. Exactly.  They could have done something.  Maybe they could have helped you.  Maybe they could have changed course.  And maybe they could have avoided a problem.  This phenomenon of things staying unspoken is just, you know, it’s pervasive, and it’s painful for everyone involved.

What We Say vs. What We Think

BILL YATES:  Jeff, one of the things – and this is a bit of a teaser for your book.  I just thought it was so good.  Right near the beginning, it may have been the very first chapter, you had, I thought, a super practical exercise.  It was almost like storytelling, where you said, “Okay, there are things that we actually speak,” and you put those on the right-hand column.


BILL YATES:  And then what’s actually going on in my head – I’m thinking of your math comments, too – on the left-hand side.


BILL YATES:  And it’s like, “Okay, here’s what I’m going to say to my project team, but here’s what I’m actually thinking.”  Or it could be more personal, “This is what I’m going to say to my close friend, but here’s what I’m actually thinking.”  And there’s so much more, and it’s so nuanced.


BILL YATES:  And just seeing that printed out the way it was really – it was both startling and made me laugh and think, you know, back to your point about the math, there’s so much going on in our head, there’s no way we can verbalize it all.  It’s a good thing I don’t verbalize it all for some things.

JEFF WETZLER:  Yeah, yeah.

BILL YATES:  But there are other things that would be so much more helpful if I would explain, you know, “Okay, Wendy, we’re having this conversation.  Here’s something that I should be sharing with you; but I’m not, you know, I’m hesitating to do It.  But here it is in my head, and you can see it printed out like a script.”  Ooph.  That was a great exercise.

JEFF WETZLER:  Yes.  It’s an amazing tool.  I learned it when I worked at a place called Monitor Group, which was a consulting firm where someone named Chris Argyris, who was one of the inventors of the entire field of organizational learning, introduced that exercise to us.  And because everyone at Monitor did it, we had that language of the left-hand column.  And we could even say to each other, you know, “There’s something in my left-hand column I want to expose to you,” or “What’s going on in your left-hand column right now?”  And so having that language of the left-hand column, meaning the unspoken thoughts and feelings as a common term in an organization itself was an intervention that allowed us to communicate better.

But because I had the opportunity to work with Chris and to read hundreds and hundreds of people’s left-hand columns, I started to realize that, you know, once you strip away some of the junk, there’s just such important information that people aren’t saying to one another that if we could invite that out of the left-hand column, we would all be better off.  We’d make better decisions.  We’d innovate better.  And we’d save time, we’d be closer.  And so, you know, to your point, that’s a lot of the motivation for wanting to pay this forward.

BILL YATES:  That’s such good stuff.

What People Withhold

WENDY GROUNDS:  So, there was a quote in your book, “People overestimate the harm they will cause you by sharing feedback, and they underestimate the benefits.”  So, people are holding stuff.  They’re withholding information.  And I know project managers probably find that happens a lot.  What are some of the most important things that you’ve seen that people tend to withhold?

JEFF WETZLER:  One of the biggest things that they withhold is feedback they have for us.  They have observations about how we could do things better, or they have observations about how we’re coming across, or unintended impacts that we’re having on them or other people.  And they often don’t tell us that.  Even though, if we knew it, we could do better.  And we probably – most of us would probably want to know that because we’d want to do better.  So that’s one category.

Another category is that people often withhold what they’re really struggling with, what they’re up against themselves.  I remember my first big operating roles where I had hundreds of people reporting to me, one of our major, very visible public projects almost completely imploded because people were struggling with things, and they didn’t tell me.  And I thought I was doing all the right things, and checking in.  And, you know, we had project plans and metrics and milestones, all that kind of stuff.  They were just paddling beneath the surface and dealing with all these struggles until the whole thing almost blew up because they didn’t tell me.  And of course, as a leader, upon reflection, it’s on me.  I didn’t create the conditions for them to tell me.  But they didn’t tell me.  So that’s another category.

Another big category is that people often don’t tell us what they really, really think about a controversial topic or issue.  They might tell us what they think we want to hear or what they think is the popular thing to say.  But what their true opinion is, and also where that opinion comes from, what’s the experience they have that animates, that informs that opinion. 

And then I think one of the other things that people often don’t say is kind of their biggest and wildest crazy ideas that might just be the breakthrough we need, that might just be the pivot we have to take, that might just be the innovation.  They might think, you know, this is too crazy.  They don’t want to hear this.  It’s not – we don’t have time for this.  And so, they keep it submerged.  Those are some of the most common things that I saw when I looked across these hundreds of left-hand columns of the important information that never got across to the other person.

Asking Superpowers

BILL YATES:  Why is it so hard for us to ask, you know, what is it about that that makes it tough?  To me, you know, you mention this is a superpower.  This is a superpower that we could learn how to ask more effective questions.


BILL YATES:  And how to listen better.  Is it truly a skill we can develop?  Do I have to be born as Superman, or can I become Superman in this ask area?

JEFF WETZLER:  You can become Superman.


JEFF WETZLER:  I think that the irony actually is that most kids are born with this superpower.  Think about how curious kids are.  Kids are so curious.  I mean, there’s really interesting studies that, you know, when kids are like four years old, they’re asking like 400 questions a day.  It drives you crazy, but look how curious they are.  I mean, they are, essentially, superheroes of this; that, you know, all they’re doing is learning.  Over time, we put them in schools that tend to shut down their curiosity, sadly.  But I think it’s really about relearning something that we were born with that we already knew.  And if we had it at one point in time, we can reclaim it.

And to your question about why people don’t ask more, I think it’s a few things.  I think that, to me, the biggest thing is we don’t realize there’s something that we need to know.  We’re not curious.  We walk around the world thinking that we’ve got it figured out, thinking that we know how this person is and what motivates them and what the right answer is in this situation. 

And so, we’re trapped in what I call a “certainty loop,” where the pre-existing beliefs and assumptions we have about the world lead us to walk into any situation and just size it up in ways that essentially reinforce what we already thought and believed.  And we get that sense of, “Here we go again.  This is how they always are.”  And so all of that keeps us stuck.  And we don’t even realize there’s something to ask about.  So that’s, I think, one of the biggest barriers.

I think a second barrier is that sometimes people overestimate how sensitive someone’s going to be about being asked a question.  And so sometimes we hold ourselves back from saying like, you know, “What is your experience with that?”  Or “What led you to go in that direction?”  Or because they think the other person’s going to feel accused or put on the spot or not want that question.  But the research shows actually we often overestimate how sensitive people are going to be.  And people tend to actually want to be asked questions.  They want to have interest.  So sometimes we hold ourselves back for that reason.

And then I also do think that it is a skill set.  And so a lot of times we don’t ask questions because we just haven’t been taught and trained on what are good questions to ask, as well.

The Ask Approach

WENDY GROUNDS:  What is The Ask Approach?  You write about The Ask Approach in your book.  Can you describe what it is to us?

JEFF WETZLER:  So, The Ask Approach is essentially, it’s the heart of the book.  It is the methodology that I propose how we can overcome the problem that we were just talking about.  It’s five practices, all of which are based in research, tested out in action, in life, that when put together really give us the greatest chance of truly finding out what the others around us are thinking, feeling, knowing, so that we can learn from them, so that we can be better off together, so that we can have closer relationships.  And I’m happy to walk through it, if you like.

WENDY GROUNDS:  Yeah, we’d like to dig into that a little more with you.  If you could just mention what each of them are, and then we’ll start with the first one and just go a bit deeper.

JEFF WETZLER:  Absolutely.  So Number 1 is Choose Curiosity.  It’s really about awakening ourselves to what we can learn from other people.  Number 2, it’s called Make It Safe.  This is about making it more comfortable, easy, and appealing for other people to tell us hard truths.  Number 3 is called Pose Quality Questions.  And this is really asking the kinds of questions that are really going to get at the essence, the heart of what someone else is thinking, feeling, knowing.

Number 4 is what happens after we ask the questions is how do we listen?  It’s called Listen to Learn.  It’s bringing attention to how do we take in really the most essential thing someone’s trying to tell us, and also even what they’re not saying, as well.  And then the fifth one is called Reflect and Reconnect.  And what that is, is it’s really about processing everything we’ve heard, making sense of it so that we can know what are the right takeaways for us?  What can we do about that?  And then closing the loop with the other person so they know here’s what I learned from you and how much I appreciate what you shared with me.  So, in a nutshell, those are the five practices of The Ask Approach.

1. Choose Curiosity

WENDY GROUNDS:  Yeah.  And those are practical things that people can do and can apply.  Let’s take a look at the first one.  You say “Choose curiosity.”  How do we choose curiosity?

JEFF WETZLER:  Yes.  So, I will say, you know, some people look at curiosity as a trait, like this person has it, this person doesn’t.  Some people look at it as a state of mind that we’re in – I’m feeling curious, I’m not.  I’m positing that curiosity is a choice.  It’s a decision that is always available to us at any point in time.  And when we make that decision to choose curiosity, we’re centering a question at the front of our minds anytime we’re interacting with a person or a team.

That question is what can I learn from this person?  And it starts with the premise there is always something we can learn from somebody.  So, if we say to ourselves, what can we learn from that person, then inside that question there comes all kinds of other things to be curious about, like what experiences do they have that might be relevant to this?  What are they seeing that I’m not seeing?  How are they watching me come across?  What impact am I having?  There’s, you know, a thousand questions that stem from that one question of what can I learn from this person?  Choosing curiosity is really about centering ourselves on that question and putting ourselves in a mindset of wanting to learn from someone else.

BILL YATES:  I like that.  You know, finding value in every person and their voice, their experience, and recognizing that they have something unique they can bring to the table, whether it’s a team member or an end customer that we’re building a solution for.  I want to hear from them.  I want to know.  It might be later after I’ve spoken to a hundred people or surveyed a hundred, I realize, okay, that’s an outlier.  That’s okay. 

But it’s good to be aware.  That takes humility, you know, on the part of me and on the part of my project team, to walk into it not thinking we have all the answers, not being open and going about it with an attitude of curiosity of, you know, these people bring value to this.  I need to treat them with respect and their opinions with respect.  What’s the best way for me to elicit it?  You know, what’s the best way for me to ask?

JEFF WETZLER:  Exactly, exactly.  And, you know, especially in the context, I think of project management, which often happens in teams.  I learned from one of my mentors, Phil MacArthur, that curiosity is a team sport.  Sometimes it can be tough to be curious when we’re trapped inside our own bubbles of our own assumptions.  But if we can surround ourselves with people and invite them to provoke our curiosity, to help us actually, when we’re getting emotional, when we’re really getting triggered to say, you know, there might be something else you’re missing.  There might be another way to look at the situation.  We can actually use the power of a team to make ourselves more curious and each other more curious.

WENDY GROUNDS:  And each person feels valued then.  If you’re curious about them, they really do feel that they’re important to you.

JEFF WETZLER:  That’s the thing about curiosity, yeah.  It’s a special kind of curiosity.  It’s not the kind of curiosity that’s like, I’m curious about the history of Russia, or I’m curious why do trees grow the way that – I call it “connective curiosity.”  Because when we’re curious about the experiences and the thoughts and the knowledge and the feelings of other people, to your point, it has this effect of connecting us with them.  And it almost gives off an energy that makes people want to share with us because they value how much we care about learning from them.

2. The Safety Cycle

WENDY GROUNDS:  But we have to keep it safe.  Your next step is Make it Safe.  Can you expand a little bit, talk about what you have as the concept of the safety cycle, and why that is significant.

JEFF WETZLER:  So even if I feel curious to learn from you, if you don’t feel that it’s safe to tell me your truth, you’re not going to share with me, and I’m not going to learn with you.  And so making it safe is really about reducing the barriers, some of those barriers that we talked about earlier, of people being afraid of our reactions or afraid of them being judged or different things like that, so that it is more comfortable, so it’s easier, so it’s more appealing to share with us.

2.1 Creating Connection

And one of the ways that we can do that is creating connection with people.  There’s a lot to creating connection, but one really actionable aspect of it is even thinking about the time and the place and the space of the connection.  And what matters is connecting on their terms and on their turf and on where they’re going to be most comfortable.

So, for the book I interviewed some iconic CEOs of corporations because CEOs are notorious for not getting the truth, for people insulating them from what’s really happening.  And when I spoke to these CEOs, I said to them, “How do you really get the truth?  How do you learn from people in your organization?”  And one of the patterns in what they said to me was, if I want to learn from someone, I’m never going to invite them into my office and make them sit across the big intimidating CEO desk from me and assume that they’re going to feel safe telling me the truth.  We cannot connect in that way.

I’m going to go to them.  We’re going to have lunch where they want to have lunch.  I’m going to go on a ride along with them on a sales call.  We’re going to sit on a sofa together.  We’re going to take a walk, whatever it is.  But there’s no single right answer about where and how to connect other than wherever the other person is going to feel most comfortable.  And so that’s a big part of creating connection in the safety cycle.

2.2 Open up First

Another part of it is if we want the other person to open up, we need to open up first.  And that could be simply opening up about why we’re asking the question in the first place, because people often are guessing what our agenda is.  And why make them guess?  We can say, look, here’s why I’m asking.  Here’s why I’m curious.  Here’s what I’m struggling with. And here’s what I need to know.  And the more that we can open up about things that might feel vulnerable to us, the more we also make it safe for them to do the same thing reciprocally.

2.3 Radiate Resilience

And then the last part of the safety cycle I call “radiating resilience.”  And this is really demonstrating to the other person that I can handle your truth.  I’m not going to shatter.  I’m not going to – I’m not so fragile that it’s going to make me crumble.  And I’m not going to take it out on you.  If I have an emotional reaction, which I might because I’m human, I’m going to assume responsibility for my own reaction.  I’m not going to blame you for the reaction that I’m having.  It could sound as simple as saying something like, listen, if I were in your shoes with everything going on, I might be really frustrated.  And if that’s what you’re feeling, I want to know that, and I want to understand.  And whatever you’re feeling, I’d really love to hear it.

Just putting that out there lets the other person know, okay, if they are feeling frustrated, it’s so much easier for them to tell me that at that point than if I just say, what are you thinking or feeling?  That’s part of radiating resilience.  So, create connection, open up, radiate resilience kind of functions as a cycle because the more that we do each one, the more it feeds the next one, and ultimately contributes to making it safer.

BILL YATES:  Jeff, this is so good.  It’s so practical.  To me, for the project manager just thinking, okay, based on what Jeff has said, this doesn’t take a huge investment.  I can do this.  You know, I just need to think ahead a little bit before I set up a meeting with someone.


BILL YATES:  I just need to put a little bit of thought into it.  Think about the context, think about, okay, are there barriers that I can remove in terms of where we meet and how we meet?  And to keep it simple, what’s the most comfortable place for the other person?  And thinking through and connecting with them, letting them know right up front, here’s why we’re meeting. 

3. Pose Quality Questions

WENDY GROUNDS:  So, let’s move on to Step 3, which is Pose Quality Questions.

BILL YATES:  This is the hard one.

WENDY GROUNDS:  Yeah.  This is kind of my thing, though.  How do you find a good question?

JEFF WETZLER:  Now I’m curious.  Why do you say this is the hard one, and why do you say this is your thing?

BILL YATES:  To me it’s like, okay, some of these things I can do.  But then when I – and honestly, I’m thinking of meetings that I have with clients where I feel like I’m really, I’m trying to maximize their time.  I don’t want to waste their time, and I’m very aware of that, very self-conscious of making the most of their time.  I don’t want to go in there with stupid questions, you know, or things that they’ve already answered that I’ve forgotten to look back through email or prior notes. 

So, I’m like, to me, formulating the right question.  Again, not to make me look clever, but to elicit the response that’s going to help the team the most, you know, give us the most information from that person.  So yeah, this is where I feel like I’m coming with my palms open going, help me, guru, help me.

WENDY GROUNDS:  I mean, even from a podcast point of view, you know, I’m always thinking, if one of our listeners was here, what do they want to know?


WENDY GROUNDS:  What would they ask?  Not what I want to know.  So, finding what is a good question and a quality question, you know, comparable to a bad question.  Can you help us?

JEFF WETZLER:  I love it.  I love it.

BILL YATES:  Please?

JEFF WETZLER:  So, I don’t like to think about any bad questions because I think the idea of a bad question can discourage people from asking questions, and I would much rather people ask the question than not ask the question.  But I do distinguish between quality questions and crummy questions.  And the definition of a quality question is simply a question that helps us learn something important from someone else.  And a crummy question doesn’t.

There’s a lot of what passes for questions that I think are crummy questions.  Questions like, you know, “Here’s what I think; isn’t that right?”  You know, that’s a question.  It’s got a question mark at the end.  But it’s crummy because it’s very difficult for someone to disagree with us when we say that.  Or crummy questions that are, you know, that are more questions that are kind of manipulating someone or, you know, don’t you think it would be better if we did this?  Like a lawyer might do it with a witness.  Or attack question, like why would you ever think that?

Using a “Why” Question

BILL YATES:  Jeff, that was such good advice.  That was one of the things that I read and I’m like, okay, whoa, that’s good.  I need to be careful when I use the word “why” in a question.

JEFF WETZLER: “Why” can sound like an attack question.  If you use the word “why,” you just have to work extra hard to explain your intention behind the question so that they don’t feel accused by what you’re saying.  But quality questions, I kind of think about almost the way that I imagine a surgeon might think about all of their tools, their scalpels and all the different things they’ve got laid out because there is a whole set of things that we could ask, if only we know the taxonomy of different kinds of quality questions.  And so, in this chapter of the book, I lay out that taxonomy, and I talk about different question strategies that we can use to get at different kinds of things that people think and feel and know.

To give you one example, one of the most overlooked and I think really powerful question strategies is what I call “request reactions.”  And that is simply to say to the other person, how did that land with you?  What’s your reaction to what I just said?  How does that sit with you?  What does that make you think?  What would be missing?  And I think it’s underused because so often when we make a statement or we give someone an input or feedback or guidance or direction, we just assume, well, if they disagree with us, they’re going to tell us.  But for all the reasons that we were talking about before, quite often they’re not going to tell us.

But if we request reactions, then we say to the other person, I really want to know what you think.  And we’re far more likely to know, do they agree?  Do they disagree?  Do they have a gut feeling that something might be off about that?  Might we be missing something?  And so, requesting reactions can open up all of that kind of learning that so often we just glide right by.  So that’s one example of a quality question strategy.  And there’s obviously many more, as well.  And all of them are learnable.  None of this is rocket science.  It’s just knowing what they are and then even knowing what are some of the specific words and phrases that we can use to implement these strategies.

Clear up Confusion

BILL YATES:  One quick example that I loved was clearing up confusion.  It was one of the points that you had.


BILL YATES:  And I thought back to, again, I’m thinking of early on in projects when we’re trying to nail the scope and the requirements.  And we’d meet with a customer.  And of course, I’m going in there with all my biases from past projects, maybe even projects with these customers that we’ve done.  I bring all this baggage in.  And we go through our questions.  We’re asking these things, and we’re making notes.  And there are times when I think there was a part of me that I was either making an assumption that I knew, okay, they responded to my question this way.  So, then I had a whole, you know, string of assumptions that I had attached to it.  I didn’t stop to validate; right?  Months later we’re building the thing slightly wrong because if I had just thought, you know…


BILL YATES:  …whoa, you’ve got some assumptions here.  Let’s unpack those.  When you describe this requirement this way, I’m thinking like this; right?  So probably you want to see a solution that gives this, this, and this.  You know, I didn’t take the time to pause.  And I don’t know if it was pride on my part, or just the need for speed to get on out of there.  Why don’t I slow down and just ask for clarification to remove any confusion way back then? 

JEFF WETZLER:  Those are perfect illustrations of how you would implement the strategy called “clear up confusion.”  And, you know, one of my mentors, Diana Smith, says it’s kind of like pay now or pay later.  It’s going to take a few extra minutes right now, but it might take weeks or months if we go off course the other way.  So why not just pay now so you don’t have to pay later? 

And even just definitionally, someone says like, you know, it’s important to me that we grow.  Well, that could mean a lot of different things.  But because we have our own assumptions about what does it mean to grow, we just keep moving as opposed to slowing down, looking, and, say, like, just can you define that?  Like, you know, all the things that you just said, like, what does that mean to you?  Here’s what that means to me.  Are we meaning the same thing or not?  Let’s – let’s get on the same page about this.

4. Listen to Learn

WENDY GROUNDS:  All right, let’s jump on to Listen to Learn, Step 4.  How can we do that effectively?  How can we listen in a way that we are going to learn?  Most of us, I’m not going to say all of us, but many of us are pretty bad at listening and actually learning what we’re hearing.

JEFF WETZLER:  Yes.  Most of us think we’re better listeners than we are, myself included.  And there’s a big difference between thinking we’re listening versus actually hearing what the other person is saying.  You know, for the book I interviewed professional listeners, including psychotherapists and journalists.  You know, journalists listen to people for a living.  They interview people.  You know, before they write about them, they listen to them.

I remember one journalist, Jenny Anderson, who’s an award-winning journalist.  She said to me that when she interviews someone, she’ll record the interview, and then she’ll play it again for herself two, three, four, five times.  And every time she listens to it, she hears something really important that she had failed to hear the previous time, you know, even on the third time or the fourth time.  And I thought to myself, you know, if she’s a professional listener, and she’s missing things, you know, the second time, the third time, imagine the rest of us mere mortals who are just having that conversation the first time, thinking that we heard it, but how much are we actually, you know, missing?  So, it is much harder to do, but there’s ways that we can get better at it.

You know, in the book I talk about listening through three channels.  So many of us listen through the channel of content, and that’s where I go naturally.  You know, that’s like, what’s the information?  What are the facts?  What are the claims?  And what are the arguments that people are making?  But that’s only one type of information that’s present when we’re listening to someone.  There’s also listening through the channel of emotion.  What are the hesitations?  What are the fears?  And what are the doubts?  What are the excitements, you know, that the people are either expressing or displaying?

And then there’s also the channel of actions.  What are the actions that they’re taking in interaction?  Is somebody delaying?  Is somebody pushing back?  And is somebody repeating themselves?  Is somebody asking me more questions?  Is somebody being very, you know, agreeing to things very quickly?  Those are all different examples of actions that people are taking.  And if we can train ourselves to listen for the content and the emotions and the actions, we literally can triple the amount of information we take in in an interaction compared to just listening to one of those channels.

I almost think of it the way that I think a music aficionado would be able to listen to the vocals and the percussion and the harmony.  And, you know, maybe first by listening to one at a time.  But then when you put it together, how much richer is the music that you hear compared to if you’re just kind of listening to your default channel?  So part of it is training ourselves to listen through a broader range of channels.

And then there’s a set of strategies that we can use that literally starts with very simple things.  The first one I talk about is ditch the distractions.  We have internal distractions and external distractions.  I am very guilty of this myself, even on video calls.  I’ve got emails coming at me, and texts, and Slacks.  When I’m trying to listen well, my latest hack is I just literally sit on my hands because, when I’m sitting on my hands, I can’t go check the email coming in.

BILL YATES:  Move your mouse.

JEFF WETZLER:  I can’t, you know, right, I can’t move my mouse.  I can’t type anything.  I just, I’m sitting on my hands right now. So, I just, I get to be very present to the conversation.

BILL YATES:  That’s good.

JEFF WETZLER:  So, there’s a whole set of strategies that starts with ditching the distractions.

BILL YATES:  So, my wife is now going to see me sitting on my hands and facing her eye to eye when I ask her something like, “Hey, how did your day go?”  I’m going to sit on my hands.  That’s good advice.

JEFF WETZLER:  Right.  Right.

BILL YATES:  That’ll keep me off my phone.

JEFF WETZLER:  Yeah, yeah.

5. Reflect and Reconnect

WENDY GROUNDS:  All right.  So, Number 5, Step Number 5, we have Reflect and Reconnect. That’s evaluating and thinking about what we’ve listened, what we’ve learned.  How can we do that?  Are there some strategies that we could learn to be able to take action on the information that we’ve learned?

JEFF WETZLER:  This is the difference between just having the experience versus getting the right takeaways from it.  It is my favorite step because, as I mentioned, I love learning.  This is how we squeeze the learning out of something is reflecting.  And I think reflecting sometimes gets a bad rap because people think, I don’t have time to reflect.  Do I have to go on some meditation retreat or, you know, be a monk on a mountain to reflect?

But reflecting can be very straightforward.  I talk about a technique that I call “sift it and turn it.”  So, the sifting it is just to simply say, let me sift through everything I heard.  You know, what’s important, and what can I let go of?  Because if we’re in a conversation and somebody told us a hundred things, we’re not going to be able to focus on a hundred things.  What are the three to five most important things that were said in the conversation, and what else can I put in the background?  So that’s the first step of sifting it.

And then once we have those, you know, the most important nuggets, I talk about three turns that we can make, three reflective turns.  And by “turns,” I mean we just turn it over in our minds.  So the first turn is to say, how does what I heard impact or evolve the story I’ve got about what’s going on here?  Does it change anything about my story, about the other person or the issue or the decision or the situation?  Myself, that’s the story level reflection.

Then we turn it again.  And we say, all right, based on how my story has changed, what steps can I take?  What decisions should I make?  What moves should I make?  Should I apologize?  Should I double down?  Or, should I, you know, go to this other person?  That’s the steps level reflection.

And then the third one is the deeper one, which is what I call our stuff, our stuff level reflection.  Is there anything I heard here that might have bearing on the deeper stuff I’m bringing to the situation?  Maybe my assumptions or biases or worldviews or ways of being because that’s what we carry into every situation.  And so if there’s something that I heard that can help me be like, you know, maybe there’s a different way to look at the world than I was before, that helps me grow in my stuff.

So story, steps, stuff, those are the three reflective turns.  I often talk about, it’s important to not just do this yourself and walk away because The Ask Approach is not about extracting information from someone else for our own gain and then just going off.  It’s a mutual thing.  And so that’s why it’s called Reflect and Reconnect.  The reconnect part is closing the loop.  It’s going back to the other person and saying, I thought about our conversation, and this is what it made me think.  This is what it makes me want to do.  And thank you for taking the time and maybe the risk to share that with me.  Also, did I get it right?  And is there anything that you would modify, that you would hope I would have learned from the conversation, as well?

I think it’s very rare that people get that loop closed, that someone would actually come back to them and really thank them and really play back what they learned and say what they’re going to do about it.  And it has so many benefits.  It signals value to the other person.  It gives you a chance to make sure you got the right takeaways.  But I also think it radically increases the chances that the other person is going to be willing to share again because they know they didn’t waste their time.  They’d know, you know, it was a good use of time because it actually led to something changing.  So that’s the reconnect part of Reflect and Reconnect.

BILL YATES:  That’s huge.  For a project manager, they really need to listen to that.  I encourage them to hit the Rewind 15-Second button on that because, I mean, that is just so important to build cohesive teams, healthy teams.  And then those customers that we’re reaching out to and asking all these questions, asking for their input.  Many times, we meet with them, maybe it’s an email or a survey that we send out, and we never follow up.

JEFF WETZLER:  That’s right, that’s right.

BILL YATES:  And if we just take a few seconds, it really doesn’t take long at all just to say thank you.  And if there’s something specific that we can put in there, hey, this new feature, or we push this date out or whatever, thanks to your input, here’s this piece.  Man, that is so rewarding.

JEFF WETZLER:  It makes a huge difference.

BILL YATES:  Oh, yeah.


BILL YATES:  You’ve got an ally then.

JEFF WETZLER:  It shows them that they have power.


JEFF WETZLER:  And the opposite of doing that, when we don’t do that, that’s when people get cynical.

BILL YATES:  Yup.  Yup.

JEFF WETZLER:  They’re like, why bother?  Yeah, he was just doing it because he’s supposed to do it.  And so by closing that loop, it really changes that dynamic and motivates people to be part of that team and to keep contributing.

How AI Can Help

BILL YATES:  Jeff, one thing I do want to mention real quickly, in the book, you get into AI.  Not that you’re writing a thesis on it or anything, but you give good advice on, hey, there are many, many emerging tools in AI that can really help us in this area.  And you gave some examples that I thought were great.  You know, very – like a quick example that you shared was, okay, share a situation that you were just in, and then literally you can type in the scenario into AI and then say, what else should I be asking, or what am I missing?  And you never know what AI is going to spit out.  It might be something you’ve already thought of, or it could be something, oh my gosh, I didn’t even think about that.  I need to have a follow-up conversation with this person.

JEFF WETZLER:  Exactly.  Exactly.

BILL YATES:  So, you know, again, that costs you nothing other than the time to open up the bot and type it in.  So, it’s a great tool right at our fingertips.  Why not make use of it?  I’m glad that you put that in those chapters.

JEFF WETZLER:  Thank you.  I totally agree.  And, you know, AI is replacing so many skills that we have, sometimes doing it better.  But I don’t think AI will ever replace the ability to really learn from other people and connect with other people.  But it can help us get better at it.


JEFF WETZLER:  And so, some of the examples that you just shared are things I discovered just along the way, writing the book, about how AI can make us better at this uniquely human thing.

Connect with Jeff

WENDY GROUNDS:  If our audience wants to get in touch with you, if they want to find out more about the work you do, where should they go?

JEFF WETZLER:  So they can find the book anywhere books are sold.  It’s called “Ask:  Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs in Leadership and Life.”  The book has a website.  It’s www.askapproach.com.  You can get all kinds of information.  There’s actually, at the beginning of the website there’s a free assessment so you can figure out how good are you at learning from other people, and which of the steps of The Ask Approach are you strongest at, and which ones might you need to grow in.  So, there’s that plus many other goodies there.  And then I love to connect with people on LinkedIn:  Jeff Wetzler.

BILL YATES:  This has been a super conversation.  The benefits here are just so obvious to me as a project manager, as somebody who’s worked with teams, who’s tried to get really valuable information from customers before.  Those people are going to end up inheriting the output of whatever project we’re working on, you know.  This is great information.  This is an area that I’ve seen some practitioners do naturally really well.  And I’ve seen people who weren’t very good at it naturally grow.  So, it does give me hope, and I totally agree with you.  This is an area that we can all get better in and that we, you know, we’re not born as Superman.  We can become super in these areas.  Thank you for your contribution this way, and thank you for the help it’s going to bring to people in my industry.

JEFF WETZLER:  Well, that means a lot.  Thank you for the conversation, and also thank you for the close read of the book, as well, that you did because I felt like it let us have a really rich conversation.


WENDY GROUNDS:  That’s it for us here on Manage This.  Thank you for joining us today.  You can visit us at Velociteach.com, where you can subscribe to this podcast and see a complete transcript of the show.  You’ve also earned your free PDUs by listening to this podcast.  To claim them, go to Velociteach.com, choose Manage This Podcast from the top of the page.  There you’ll find a button that says “Claim PDUs,” and you just click through those steps.  Until next time, stay curious, stay inspired, and keep tuning in to Manage This.


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