[Author Series] Mastering Leadership Questions With Jeff Wetzler

Jeff Wetzler is the Founder of Ask Approach, a platform dedicated to breakthrough leadership and personal growth through a five-step methodology. Jeff is also the author of the book Ask, which provides practical tools and strategies for enhancing leadership and tapping into hidden wisdom. He has over 25 years of experience in leadership development, including his tenure as Chief Learning Officer at Teach For America and as Co-founder and Co-CEO of Transcend, a nationally recognized educational innovation organization.

Here’s a glimpse of what you’ll learn:

• [03:18] Why psychological safety is crucial for honest communication in organizations
• [09:30] Using “how” questions to enhance processes and drive innovation
• [11:18] How asking the right questions changed organizational performance at Teach For America
• [16:10] The life-changing realization that even assertive leaders can overlook their need for curiosity and questioning
• [20:16] How the ladder of understanding informs the way we interact with the world and approach certainty
• [25:28] How effective listening and the “doorknob moment” contribute to understanding others
• [35:12] How leaders can use reflection and reconnection to build trust and transparency across an organization
• [48:05] Jeff’s perspective on leadership vulnerability and team dynamics

In this episode…

Have you ever wondered how leaders can best create a psychologically safe environment, cultivating a workplace culture of curiosity and open communication? Once these concepts are understood, what’s the best way to implement them?

Jeff Wetzler emphasizes the importance of creating a culture where people feel safe to communicate openly without fear of judgment. He shares a personal story about a high-stakes event where his team failed to disclose issues because they didn’t feel safe, leading to a near disaster. This experience underscored the necessity for leaders to foster psychological safety by building genuine connections, being transparent about their intentions, and demonstrating resilience. Jeff also dives into the art of asking quality questions, listening effectively, and reflecting on feedback, which are all instrumental in tapping into the hidden wisdom within any team.

In this episode of Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Jeff Wetzler, Founder of Ask Approach, to explore how psychological safety and curiosity can transform organizational culture. Jeff emphasizes the importance of reflection and connection to enhance learning and build strong relationships, offering valuable insights for leaders looking to drive meaningful change in their organizations.

Resources mentioned in this episode:

• Jeff Wetzler on LinkedIn
• Ask Approach
• Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs In Leadership and Life by Jeff Wetzler
• Amy Edmondson on LinkedIn
• Right Kind of Wrong: The Science of Failing Well by Amy Edmondson

Special Mention(s):

• Chris Argyris
• Wendy Kopp on LinkedIn
• Kim Scott on LinkedIn
• Radical Candor
• Adam Grant
• Jim Collins
• Parker Palmer on LinkedIn

Related episode(s):

• Leading with Passion with Gino Wickman Founder of EOS Worldwide on Inspired Insider Podcast
• [One Question] Awakening the Entrepreneur Within featuring Michael Gerber Founder of Michael E. Gerber Companies on Inspired Insider Podcast
• [Sweet Process Series] How to Build a Business That Can Thrive Without You with John Warrillow of Built to Sell on Inspired Insider Podcast
• [One Question] Hostage Negotiator Loses The Hostage with Chris Voss of Black Swan Ltd on Inspired Insider Podcast
• [Sweet Process Series] How to Achieve Stress-free Productivity with David Allen of Getting Things Done on Inspired Insider Podcast

Quotable Moments:

• “If you actually want people to tell you the truth, they’ve got to feel safe.”
• “When people are not successful here, it’s because they think they have to put on an air of having it all figured out.”
• “The smartest, most successful people have been rewarded for having answers as opposed to asking questions.”
• “Quality questions help us learn something important from somebody else.”
• “I assume I have to earn their trust, which means I can’t wait for them to build our connection.”

Action Steps:

1. Encourage curiosity among your team: Cultivate an environment where asking probing questions is valued and rewarded, driving innovation and problem-solving.
2. Develop a psychologically safe workspace: Use strategies, such as actively listening and openly sharing struggles, to allow team members to express their truths without fear.
3. Regularly challenge existing processes: By questioning why things are done a certain way, leaders can uncover insights for improvement and adapt to changing conditions.
4. Engage in active listening: With techniques like the “doorknob moment,” leaders can catch crucial insights that team members might otherwise be hesitant to share.
5. Practice and advocate for reflection in leadership: This fosters a culture of continuous learning and adaptability, crucial for navigating a dynamic business environment.

Episode Transcript

Intro 0:14

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Jeremy Weisz 0:22

Dr Jeremy Weisz here, Founder of InspiredInsider.com where I talk with inspirational entrepreneurs and leaders today, is no different. I have Jeff Wetzler, and you can check them out at AskApproach.com. The book Ask we’ll talk about and also has experience, long experience in education, and also Transcend Education as well. And Jeff, before I formally introduce you, I always like to mention other episodes. People should check out other podcasts. Since this is part of the Author series, you could check out some other ones. Did one with Gino Wickman of Traction. That was a good episode. Michael Gerber wrote the E-Myth that was also an interesting one. John Warrillow wrote Built to Sell, and Chris Voss Never Split The Difference, which is also a popular one, and David Allen of Getting Things Done. So those episodes are really good. It’s, you know, they’re 45 minutes an hour, and I don’t know, Jeff, I consider it kind of like a book summary. If people can get, like, a taste of the best story, so they can, you know, tackle the book itself. So check those episodes out.

This episode is brought to you by Rise25, at Rise25 we help businesses give to and connect to their dream relationships and partnerships. And how do we do that? We do that by helping you run your podcast. You know, we’re an easy button for a company to launch and run a podcast. We do the strategy, the accountability and the full execution. So Jeff, we call ourselves the magic elves that run in the background that make it look easy for the host and the company, so they can create amazing content, create amazing relationships, and, most importantly, run their business. You know, for me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships, and I found no better way, over the past decade to profile the people and companies I most admire and share with the world what they’re working on. So if you thought about podcasts, and you should, if you have questions, go to Rise25.com to learn more. Email us at [email protected]

I’m excited to introduce Jeff Wetzler. He’s been on this quest for a quarter century to transform learning opportunities. He is the author of Ask. Ask if you Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs In Leadership and Life. And the book blends a unique set of leadership experiences in the fields of business and education. He’s actually pursued this quest as a management consultant to the world’s top corporations, as a learning facilitator for leaders around the world, as the Chief Learning Officer at Teach for America, and also as Co-CEO of Transcend, which is a nationally recognized innovation organization. Jeff, thanks for joining me. 

Jeff Wetzler 2:58

It’s great to be with you, Jeremy.

Jeremy Weisz 3:00

Now for people listening, there is a video version, and I’m gonna pull it up. We’re gonna take a look here. We could see Ask right here, talk a little bit about Amy Edmondson and the forward of the book.

Jeff Wetzler 3:18

Absolutely. Amy Edmondson is a professor at Harvard Business School. She studies organizational behavior. She is probably best known for her work on psychological safety, and psychological safety plays a big role in the book, and some of her most important findings are that if you want people in organizations to feel free to share their truth, to admit mistakes, to communicate openly with one another, they’ve got to feel psychologically safe.

That means that they cannot fear consequences or punishment for being who they are and speaking their truth. The more that people feel safe, the more that you’re going to have truth telling, honesty, learning happening in organizations. She’s a true hero of mine. She actually just came out with her latest book called The Right Kind of Wrong, which is all about how we orient ourselves to mistakes and failure in productive ways, in ways that actually generate learning and optimism and better performance. So I encourage people to check out her book too.

Jeremy Weisz 4:24

And you could see here, um, there’s this question mark, and we can go through some of these things. Choose curiosity, make it safe. Pose quality questions, listen to learn, reflect and connect. Let’s, let’s stay on. Make it safe for a second. I’m sure you get called into organizations. And, you know, it kind of goes back to culture, right? So how do you go into organizations that maybe the culture isn’t making it safe for people and how they should navigate that?

Jeff Wetzler 4:56

Yeah, so maybe I can answer that question first with a story of my own experience. I was a leader. This was one of my early experiences as an operating line leader, where I had hundreds of people on my team, and we were overseeing major events throughout the country. And on one of those teams, things were not going well, and it was a very high stakes event. And all year long, I was very curious. I thought I was asking all the right questions, and I discovered almost too late that it was about to blow up, that things were about to go off the rails. And what I realized later was that people didn’t feel safe actually telling me the challenges and struggles that they were having, which was a real problem, because I could have helped. I really could have you know, made a difference, etc. Instead, they were trying to solve it all themselves and make sure that I felt confident in them and their leadership, etc. And so I learned a really hard lesson, but an important lesson, that if you actually want people to make it to tell you the truth, they’ve got to they’ve got to feel safe, which means that they don’t, they’ve got to feel like you’re not going to judge them or punish them, or it’s not going to tank your relationship with them for them to tell the truth.

And I further learned that that is extra important when you’re crossing lines of difference, whether there’s power, differences involved, where people, in that case, I had more authority, but also differences in any other kinds of identity markers, whether gender, race, language, background, et cetera. And so making it safe is really about confronting that reality by creating a level of connection with people that helps them to feel much more comfortable. Often, that connection has to be on their terms and on their turf, and not on what’s gonna make me comfortable, but what’s gonna make them comfortable? It’s about myself opening up and letting them know. Here’s why I’m asking you those questions. Here’s my own agenda, so you don’t have to guess. Maybe even here’s a struggle I’ve had or something that makes me feel vulnerable so they can see it’s okay to go there.

And it’s also about what I call radiating resilience, which is to let them know, to demonstrate, to express, that I can handle what they have to say. I’m not going to crumble, I’m not going to freak out, it’s I’m not going to take it out on them. And so those strategies of creating connection on their terms, opening up myself, radiating resilience, are all part of what any individual can do in an organization. And I would say back to your question, even if an organization has a broader culture that is not as safe as individual people, whether they’re in leadership roles or really in any roles in the organization. And I truly believe that anybody in an organization can be in a leadership position and can exert leadership no matter where you sit in the organization. If you take those steps and follow those strategies, you’re going to increase the safety of people around you.

Jeremy Weisz 7:39

You know what you just said, Jeff is really concerning, because you seem like a really friendly, open person. So if they weren’t comfortable with you, you know,

Jeff Wetzler 7:47

That’s what I thought. I thought, you know, look at me. I mean, it’s just me. Why would you? Why would you be intimidated by me? Why would you feel that, you know, like I’m my own, you know, you know, insecure person, and I’ve got my own life, who would possibly intimidate me, but I had it all wrong. Even just being in a certain position creates a level of power dynamic, let alone all the other aspects of difference in identity that I was just learning about at the time. So some of the things you said, do you incorporate them now proactively, like you mentioned a couple things, like sharing a struggle. What are some of the things you do now differently? Because, you know, I would see you as, okay, I could go to this person and be open, but yeah, obviously the people, some people, didn’t, yeah, I mean, I would say the first thing is, I don’t assume that people are going to feel comfortable. I have, I assume I have to earn their trust, which means that if there’s, if there’s going to be a time that I’m going to need to learn from them or ask them important questions, et cetera, I can’t wait for them.

I can’t wait for that time to build our connection. I’ve got to build our connection way in advance. You know, one of my mentors used to use an expression at one point that said, dig your well before you’re thirsty. And so if I’m thirsty to learn from them. I gotta dig that relationship, you know, for weeks, months, years in advance, beforehand. So that’s one of the things that I do. And then I would say a second thing that I do is I really try to reveal why I’m asking questions. So many people will make up stories, and guess how he must be asking because he’s getting ready to fire me. He must be asking because he wants to cut them or whatever. Usually, I’m just asking because I want to learn from them, and I’m curious. And so stating that in advance, so that they don’t have to guess, is a second thing that I really try to do quite often. 

Jeremy Weisz 9:30

What would be one example of something that you ask that they may be suspect of?

Jeff Wetzler 9:38

Sure. I mean, I think one of the simplest things is a question of, how can we do it this way? You know, if, if I’m, if I’m working with a team of mine, and I’m saying, and I’m watching how we’re doing something, and I think to myself, huh, I don’t know that I would have thought to do it that way.

Jeremy Weisz 9:54

And they think you’re questioning your methods.

Jeff Wetzler 9:56

What, you know, I’m thinking like, they think Jeff must think that’s dumb, or Jeff must think. That’s a bad idea or whatever. But if I were to say to them, that’s really interesting, I never would have thought to do it that way. I’d love to learn more about that. Tell me more about what you’re thinking about that way. It has a completely different tone and impact.

Jeremy Weisz 10:13

Do you ever get the scenario of the flip side, where there’s this scenario where you make it it’s people don’t feel safe and they’re not telling things, or you do have that environment of making it safe, and then they’re coming to you too much, whereas you want them to figure out, just figure it out yourself. 

Jeff Wetzler 10:34

Yes, yeah, absolutely. I think, like anything in life, things can be taken to an extreme. If I had to choose between one or the other, I would choose to have them come to me too much versus not enough. But when they come to me, I can then say to them, that’s a great thing to think through, you know, let me, let me offer you a suggestion, which is that you can take some of these steps beforehand and then come to me, you know, at a different point in the process. And so there’s a way to say that with that, I think I can still preserve the psychological safety while not having it overswing so much.

Jeremy Weisz 11:05

Is there an example or story that sticks out when you evaluate and you ask that, you know, how can we do it this way that actually changed the process for the better?

Jeff Wetzler 11:18

Absolutely. And I’ll go back to a scenario where I had been managing a big organization nationally, and we were, we had instituted a set of processes to set goals and kind of monitor progress, and every person and every person, and then the person they were supervising had their goal and their trackers and all, you know, their metrics and all that kind of thing. And it was working well, in the sense that it was helping us grow and hold, keep a hold on quality. But it was starting to, it was starting to dampen morale. People were, people were like, going along with the process, technically, but it was, we were not unleashing their actual inner visions and their drive and their fulfillment, why they actually came to it. And so we called a time out, and we said, let’s, let’s, let’s name what we’re seeing here. Here’s what’s working, but here’s really what’s not working. And this is part of opening up and to say like that, you know, I think I’ve contributed to the problem by creating this. Let’s talk about why we do it this way, but also let’s talk about what might be some different ways to do it. And I actually think you all who are on the front lines are going to have better ideas for how to do this than any of us are going to do.

So in addition to talking about why we’re doing it this way and what we want to preserve and what we’re getting, I use this strategy that I write about in the book that’s simply called invite ideas. And by inviting ideas, you can actually tap into the collective intelligence of a team or an organization. And the ideas that we came up with were not to throw away all the goals and trackers and measures, but to anchor them in more of a qualitative vision that each person got to articulate, and that qualitative vision became the North Star that motivated them even while they were keeping an eye on the progress. That’s an idea I never would have personally thought of. But because we actually had that conversation, we asked, why are we doing it this way? And what can we be doing differently? We unleashed an amazing amount of energy in the organization and performance. 

Jeremy Weisz 13:13

Yeah, I feel like we need to do a lot more of that and a better job of just challenging. Why? Because at one point, we may have done something for a certain reason, and things may have changed, right? And reevaluating why we do it this way anymore, and is there a better way now?

Jeff Wetzler 13:30

Especially because the world is changing so fast, so even if it worked last year, there doesn’t mean there’s anything wrong with it, but the world’s changing, and so we got to reevaluate it, and that requires asking questions.

Jeremy Weisz 13:42

What made you decide to write this book in the first place? You’re super busy, you have a million things on your plate, and then you say, I’m gonna write a book. 

Jeff Wetzler 13:52

So the biggest reason that I wrote it is because the problem that the book is trying to solve, I think, is pervasive. I see it everywhere. And maybe just to back up and state what that problem is, all of us, as leaders, as individuals, as just human beings in life, are surrounded by people. Those could be our customers, clients, investors, bosses, people we manage, friends, family, et cetera. We’re surrounded by people who know things. They have ideas, they have feedback for us, they have perspectives, they have life experiences that are incredibly valuable, but far too often, we actually don’t hear what they have to say, or we don’t hear all of what they have to say, and the reason we don’t hear it is, very simply, they don’t tell us, and when we don’t then when they don’t tell us, and we don’t find out, we pay a cost. We don’t make good decisions, we don’t innovate as well. We waste time.

Our relationships are more distant. So I saw this problem was everywhere, and as you can probably tell from the stories I’ve already shared, I personally experienced this problem and paid those costs myself. But I also saw that it didn’t have to be this this way, and in the work you referenced that where I started my career for about a decade at a management consultant company called monitor group, had a number of amazing mentors, including Diana Smith, Jamie Higgins, Jim Cutler, a bunch of other people, all who were disciples of someone named Chris Argyris, who really created this body of work. He was an organizational psychologist and worked with monitors at Harvard Business School, and he developed a set of tools and resources that my mentors kind of refined and shared with me, and then gave me the opportunity to share with people all around the world.

And I saw over and over again how when people could embrace these tools, it would literally change everything. They would say, like, it was life changing to me, even now, as I’m promoting the book and going back to people, they would say things they’re saying I’m getting emails that say, like, I will never forget that day that we spent together, because everything changed after that. So this stuff was so powerful. And I thought, if this problem is pervasive and these tools and ideas are powerful, can I put them together and essentially pay it forward? And I wanted to basically help other people get access to what I found and what others have found to be some of the most important sets of ideas.

Jeremy Weisz 16:00

Jeff, what was one of those times where you look back and someone said everything changed because of that conversation?

Jeff Wetzler 16:10

Yeah. I mean, so to picture a workshop full of smart, successful management consultants who went to the best had the best, had the best training in schools and all that kind of stuff, which, incidentally, Chris Argyris, who was the originator of some of this stuff, often found that those kind of people were the worst at learning from other people. It’s the smartest, most successful people who have been rewarded for having answers, as opposed to for asking questions and things like that. And so picture, let’s just say one person in that room who is telling a story and bringing a what we called a case into the conversation about a really challenging interaction that they had with a client. And in those cases, we would have them literally recount the dialog, pick a five minute snippet and say, I said this, she said this.

I said this, she said this. And then on the left hand side of the paper. Jot down all the things that you were thinking and feeling, but not telling your client at that time, we called that the left hand column, and so that was like a window into the stories that they were telling themselves. And at the end they would say this client was just impossible. They would not at all listen to our recommendations. We kept telling them why that is, why they needed to close these three factories. We keep telling them all this, and they, all they would do is just play tile politics with us, etc. And so, you know, this person’s incredibly frustrated, but also failing in their job, because they’re not actually, you know, making change. And so we would take a look at their dialog. And the first thing that we would do in taking a look at the dialog is a very simple scoring. We would just say, count the ratio of statements that you make to questions that you ask. So they look down the dialog and all of a sudden, they would have this shock and say, oh my God, I never asked my client a single question.

All I did was tell them what I thought the right answer was, and when they started pushing back, I just repeated myself, or I gave them more data points or whatever. And what I never learned is, why do they disagree with my answer? What other ideas do they have? What’s the history then they’re in their organization that I never had, and it’s like a life. It’s like a life changing moment to realize I’m stuck, but I’m causing my own stuckness, because all I’m doing is asserting things and never inquiring. And so from there, we would often go to that’s interesting. What would happen if you ask questions? What might be some questions you would ask them, and the kinds of them? And the kinds of questions that they and the group would come up with were simple but incredibly powerful questions that they thought to them, as I could, they thought to themselves, I could totally ask this question. I could see how it made a huge difference. But then we would peel the layer back one more time and say, You know, chances are it’s not random that you didn’t ask any questions.

What was the story that you had going on about yourself and your client that prevented you from asking any questions? And the story was usually some form of, I’m right, they’re wrong. My job is to convince them that I’m right, they’re wrong. And so then we would ask the question, well, how come that was your story? What led you to have the story that trapped you inside the certainty so much that you couldn’t even ask a question authentically, and that’s where some of the deepest kind of ahas would be, which is, why would I? Why would I construct a reality that makes it that, you know, that is blind to the fact that I’m missing so much? Why would I not be curious about that? And then that starts to open up a level of curiosity.

And then what we would do is play out all right now with this more curious story, and with this more balanced set of assertions and questions, how can the conversation go? And usually it would go dramatically differently. And then people would come back and, you know, the next workshop and report, I had a complete breakthrough in my in my relationship with my client, and, by the way, also a complete, complete breakthrough in the relationship with my husband too, because I realized I was doing the same thing in my personal life as well. So that is helpful as a story.

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