Many leaders have never been trained in the skill sets of humility, authenticity, and curiosity. These traits in a leader can promote cohesiveness and trust in your team’s culture. A key way of creating this kind of culture is asking questions. In Episode #53 of our Executive Leadership Podcast, we challenge you to “Dare to be Dumb” by asking more questions.

To cultivate leadership development on your team, consider bringing a 5 Levels of Leadership Workshop to your organization this year.

Read Transcript Below:

Perry: Welcome to the John Maxwell Executive Leadership Podcast, where our goal is to help you increase your reputation as a leader, increase your ability to influence others, and increase your ability to fully engage your team to deliver remarkable results. Hi, I’m Perry Holley, a John Maxwell facilitator and coach.

Chris: And I’m Chris Goede, vice president of the John Maxwell Company. Welcome and thank you for joining. As a reminder, if you would like to learn more about the 5 Levels of Leadership or perhaps even bring a 5 Levels workshop to your organization, please go to and, in addition, if you have a comment or question for Perry and me, we would love to hear from you. Well, you guys know I like this part. My favorite part of every podcast is when Perry reveals the titles. With this one, I’m not sure if he’s talking directly to me or not. Today’s topic is “Dare to be Dumb.” The power of questions. This is a big topic for our organization and for John himself–so much so that he wrote a book about it. Before we get into all of that though, what drove this title? Where did you come up with it?

Perry: This one was very personal to me. When I first was promoted from being a salesperson to being a first line manager, I was making a lot of sales calls. I made a sales call with who I thought was the smartest technical salesperson I’d ever met. I mean, if you’re a salesperson, you know, if you have a tech salesperson that can go on a call with you, it always makes you look better. I could keep my mouth shut. They do the talking. But this really smart technical salesperson, who knew our product inside and out, asked the customer a question that I almost did a double-take about. I thought, “Even I know the answer to this question! Surely this person knows the answer. He’s the smartest person I know.” I mean, his business card said PhD, and that’s where it started. Down from there, there were all these acronyms about how smart he was. So, I kept my mouth shut and listened, and the customer talked and talked all the way back to the office. We stopped and got a coffee, and I asked the salesperson, “Why did you ask that? Did you not know the answer to that question?” He goes, “No. I thought I knew the answer, and I’m pretty sure I did know the answer. But what I realized is that it pays every now and then to just dare to be dumb and ask a question. Because if the customer starts talking, I can almost always learn something new that I didn’t know.” It just really struck me that he didn’t play “I’m the smartest person in the room,” he played “I might could learn something from everybody I meet, and I’m going to dare to be dumb.” That was the phrasing he used. I go, “I love that.” Just take a risk. I might look dumb, but I might learn something. And by the way, what I’ve learned is if the customer is talking, I almost always sell more. 

Chris: Yeah, that’s exactly right. That’s a great story. I’m glad that you learned that at such a young age. Too many of us, as leaders, get away from the ability of understanding the power of asking questions in order to engage others and tap into their ideas. John teaches a lot about this. Man, he just models it for us, whether we’re at a dinner or a client story or a meeting. It’s interesting because it’s part of what we need to do as leaders, yet if you think about it, we’ve never been developed in the ability to ask questions. It’s a skillset. Think about different careers, like a journalist. I was listening to a talk show and someone said to the journalist, “that’s a great question.” And she said, “well, that’s what we’re trained to do.” And then it got me thinking: as leaders, do we do we spend enough time training other leaders or even training ourselves to be able to ask really good questions? Here’s something I wrote down: Questions are a powerful tool for unlocking the value in an organization. They spur a couple of important things. Obviously, it spurs learning; the exchange of ideas fuels innovation. They fuel performance, and they build rapport and trust. The other thing that’s interesting, something we’re always thinking about as leaders, is how do we mitigate mistakes and risks? I think that we have the ability to uncover pitfalls if we think about how to ask the right questions. John teaches a lot about this. Here’s a couple of his reasons behind why he teaches this: You only get answers to the question you ask, and questions unlock doors. I just mentioned that a little bit from a risk standpoint. Here’s another one: Questions cultivate humility. I love that word when you talk about leaders. You and I both do training, and we always ask, “What’s the characteristic of a leader that you think the highest of?” Most of the time, the room will come back with humility. I think questions are a great way to cultivate humility.

Perry: Yes. My personal experience with this is that my wife and I were at this reception some years ago, and I was greeting someone. I asked him a question about what he did and he started talking and… You know, my temptation is to talk about me and what I do because, let’s face it, that’s very important–but only to me! So, I asked him a second question and a third question, and of the nine or ten minutes we were talking, I probably talked for a minute. He talked for nine minutes. When my wife walked up, he said to her, “I just want to tell you that Perry’s such a great communicator.” She asks me, “Well, what did you do?” I said, “I ask good questions and then listen to the answer.” To what you said about John’s point about cultivating humility, I feel like if I ask good questions and listen to the answers, I make others feel important, make them feel relevant, and make them feel needed. They’re engaged and feel invited into a conversation. You build this connection with people by allowing them, through your questioning, to engage in the conversation. 

Chris: One of our executive facilitators, Greg Cagle, talks a lot about this topic. When a leader comes into a room, and then he or she leaves the room, do you feel like that individual was the smartest person in the room or do you feel like, my goodness, I added so much value, I might be the smartest person in the room. He says to really think about which leader has a greater impact. Really, that’s driven around the power to ask questions. But a lot of times we don’t do that, right? Because as leaders, we want to have all the answers. We don’t want to appear like we don’t know what’s going on. And, as I mentioned earlier, a lot of the time we haven’t even been taught this skill set of leading people in the EQ side of things, like journalists or litigators or doctors have. So, I wrote down four things that I was thinking about when it comes to reasons we would potentially not ask questions.

Perry: Yes. If all of this is so positive, why do we struggle with it?

Chris: Yes, exactly right. Well, here’s four reasons, and you can think about what you might struggle with if you don’t ask enough questions. The first one is just being candid. Maybe there’s an egocentric problem, meaning, “I’m going to impress you with what I know.” That’s when you’re the one talking, and you want to continue telling people what you know, so that when you leave the room, they’re like, “wow, that was the smartest guy I’ve ever met.” The second option is maybe you’re just apathetic. Maybe you don’t even care enough to hear the other person’s answers, so you don’t actually ask questions. You’re apathetic to learning something new, to hearing their answers. The third one I wrote down is that maybe you’re just overconfident as a leader. You already know everything. And then, finally, maybe you think you’re going to ask the wrong questions, that your question is not relevant, that you didn’t hear the proper context, and you don’t want to seem incompetent. You think, “I’m going to ask the wrong questions, so I’m not gonna ask anything at all.” Those are a couple of reasons why I think leaders at times have a tendency not to ask questions.

Perry: I love that. I’m reflecting on my own life as I’ve grown in this area. I went from being kind of me-focused to being others-focused. I realized, as a leader, I think my number one job is to connect with everybody in my circle of influence. John teaches a lot that everybody communicates, but are you connecting with people? If I’m just communicating, there’s usually a lot of one-way from me versus connecting both ways. This reminds me–we’ve talked here before, maybe once or twice, about Liz Wiseman’s work in Are You a Genius or a Genius Maker? I was thinking about that when you were talking about being the smartest person in the room. Am I trying to act like a genius because the people on my team expect me to be a genius and diminishing, as Liz says, the capabilities of others? Or am I actually engaging you, making you the genius, and drawing out the collective smarts of our team. Being the “genius maker”, she says, multiplies the capabilities of the team. I think we tend to want to look good, but that’s not going to help us have a team of highly engaged workers and teammates working together. That’s going to diminish them. 

Chris: Well, one of the things you’ve talked about in the past is “what are you doing as a leader to step back in order for your team to step up?” This is a great example. Questions allow you to hear the perspective of everybody that’s at the table, and when you’re open to their perspective, then you’re going to get their buy-in. Sometimes we talk about when you’re leading and connecting with people at Level 2, but I think the power of questions really falls into Level 2 and Level 3, right? At Level 2 we talk about the values (I’m going to use the word value a lot here, but just hang with me). When an individual knows that something they value is valued by the organization, they value the organization and their leader to a higher extent. So, I think it’s the same thing with perspective. Even if we talk a lot about alignment and agreement, even if we leave the room, we’re not completely in agreement, but we are all in alignment. That happens because you allow everybody to use their perspective in a meeting. So, I think that the ability to have everyone step up not only multiplies (to quote Liz Wiseman) the talent, but it gets their buy-in for whatever direction you’re moving, because everyone feels they had a voice. 

Perry: Right. I require everybody on my team to, when you come to a call, a meeting, or a face-to-face, you better have a point of view. I value that. I’m going to ask you questions about what you think. I want to get your feelings on this word curiosity. If you ask me how to develop great questions, I’d say to have a natural sense of curiosity. In the leadership world, leaders with curiosity have been spoken about quite a bit recently. I wonder how you see curiosity as a leadership competency. Where does curiosity fit into the leader’s journey?

Chris: I think curiosity shows that you’re interested in hearing what others have to say more than what you have to say. You achieve curiosity through observation. You also achieve it through questions. I threw the word observation in because, while we talk about how leadership is a visual sport, you need to be watching as much as you’re listening. I think people have curiosity today, but you know how they answer it? They answer it by talking to Siri or going to Google, and they just ask one question. I was watching a sporting event last night, and I was curious about something, so I Googled it and there’s my answer. I thought, how many times do I do that in a work environment, lean towards having technology answer a question for me versus having my team answer it for me? I was like, wow. I probably ought to make sure that I’m being curious, not only for my own self-development, but for my team’s. 

Perry: Right. Sometimes I’m just not comfortable not having the answer. I think I’m like a lawyer. I never ask a question if I don’t know the answer already. Well, I’m not like a lawyer. I’m a leader, and sometimes it’s okay not to have the answer. There might be a different answer than the one I have. I heard Brené Brown say once that she’s in it for however long it takes to get to the heart of the problem. I don’t have to know the answers to say the right thing. I just have to keep listening and keep questioning. When I heard that I thought, yes, yes. Sometimes leaders just need to get comfortable with the discomfort of not having all the answers, and be willing to work with others to find the answers. I do have an answer. I almost always have an answer. But is it the right answer? I don’t know. Curiosity is about asking great questions. Drawing on the collective intelligence of the team might make for a better answer, but if I can get out the question. 

Chris: This brings me back to your title. What you learned at a young age, which is: hey, dare to be dumb! I dare you to be comfortable with being dumb, which will change your mindset around the power of asking questions of your team. There’s two words that come to mind: vulnerability and authenticity. And let’s just be honest: your team knows what their leader doesn’t know. They already know! I want to challenge you to think in terms of authenticity and think in terms of being vulnerable with your team. When you do that, the culture, the cohesiveness, and the transparency will allow your team to go to the next level. 

Perry: I know that we often say that the number one retention tool for most folks is feeling valued. “I feel valued by you, the leader, I feel valued by the organization. I’m not gonna go anywhere. I’ll probably work for less money. If I feel valued, I’m in.” I’ve found that questions are a great way for me to increase my ability to connect. I already said, it increases, in a person’s eyes, the knowledge that I value you. I’m asking you something. If you’ve ever given a speech in front of a group and you say, “are there any questions?” and there’s no hands, no questions, just silence, how does that make you feel? More valued or less valued? I sometimes I speak to nonprofits or school groups, and I went to a nonprofit run by my friend, and he said, “Come speak to these teenagers, about 50-60 teenagers. Could you do a little leadership lesson?” I said I’d be glad to. So, I get there. Nice audience, good-looking kids. At the end, I say, “Well, that’s all I have today. Are there any questions?” and 55 hands went up at the exact same time. I almost fell off the stage. It blew me away. They had taught them that any time you’re listening to someone, one-on-one or in a group, you should be formulating a question in your mind. Now, did every one of those 55 kids have a question, or did they just throw their hands up? I don’t know. I called on several. My friend had told every person to be prepared with a question. I took away the message that every time I’m listening to someone on a conference call, in the boardroom, or in a meeting, and somebody else is talking, I should be thinking: what could I ask this person to, one, help solidify what they’re saying in my mind, two, make them feel that I was listening, and three, make them feel important? Plus, it increases my active listening skills.

Chris: That’s a great story and the exact opposite of what I experienced this week, by the way. I was with a large organization. I got done in about an hour and a half of interaction. I said, “are there any questions?” and there’s the pregnant pause. I was like, “I’m so sorry. I think I just wasted your time.” They all started laughing, and then I finally got one question. It was “When’s lunch?” I’m just kidding. So, wrapping up, here’s a couple of things I wrote down from our conversation. I want to give you some call to actions, some thoughts. By asking questions, we naturally improve our emotional intelligence, which in turn will make us better questioners. It’s a cycle. We talk so much about how 85% of the time, as a leader, we need to be focused on the EQ side of leading people. Questions will take you there. Even if you don’t like people and you don’t want to build relationships, still ask questions. As leaders, let’s start ending fewer sentences with a period and more with question marks. We talked briefly about how this is kind of a Level 2 and Level 3 skill set. Developing that competency to in order to set that foundation and asking a lot of questions unlocks learning and improves the interpersonal bonding with those that you’re leading. Finally, getting back to your title, it is great. I’m going to go home and tell my wife “I’m going to be dumb. I’m going to dare to be dumb.” So, I challenge you as a leader. Just dare to be dumb. Your team already knows that you’re probably a little dumb. 

Perry: Fantastic. Well, thank you all for joining us. It’s always a pleasure to bring a message. If you’d like to learn more about our work with the 5 Levels of Leadership, or even potentially have a 5 Levels workshop at your location, you can always find us at As Chris said earlier, if you have a question or a comment or want more information, you get that from us there. Have a great day. Thanks. It’s been the John Maxwell Executive Leadership Podcast.

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