Episode 36 – Transformational Questioning: Continuing Conversation with Matt Bailey

Images of host Norah Jones and guest Matt Bailey, with additional text "Part 2 Available Now"
It's About Language, with Norah Jones
It's About Language, with Norah Jones
Episode 36 - Transformational Questioning: Continuing Conversation with Matt Bailey

Being safe and valued, questions, concepts, freedom to speak, are so evident at companies that have an amazing work culture. When there is a negative work culture, there are barely any questions. People are afraid to ask questions and you can see people start to ask something, but then stop, rephrase, and go safe. They’re not going to put themselves out there. They’re afraid of looking incompetent.”

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This week’s episode is a continuation of my terrific conversation with Matt Bailey (bio). You can find the first part of the conversation in Episode 35.

We know that questions are asked all the time. But so many questions that we ask are fact related. There’s nothing wrong with that. But facts only take us so far in the world. They continue our labeling and understanding of things, but not necessarily ourselves or others. Transformational questioning looks at active questioning and how it relates to releasing the power of individuals and communities.

They are elements of transformational questioning that we address in the podcast and then I address in my workshops on how to work with questions. It was a life and career game changer for me when I participated thirty years ago in a three-year research program on developing and applying the skill of questioning. Since then, in consulting for and training educational and business clients, I have continued to explore, clarify, and share questioning approaches that make for breakthrough growth in individual and team well-being and cooperation.

Matt and I touch on some question types and approaches in this second segment of the podcast. As you listen and consider your own circumstances-–the interactions you have with family, community, friends, work colleagues, etc.–reflect on how you form and use questions.

Which of the elements are those that play a part in how you have approached questioning in your life? Which are reminders or new insights for you?

Enjoy the podcast.

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It’s About Language – Episode 36 – Transformational Questioning: Continuing Conversation with Matt Bailey

Scroll down for full transcript.

Want to hear more? Access previous episodes, and get to know the wonderful people I talk with through the It’s About Language page, or by clicking on the Podcast tab above. You can also find this week’s episode on Apple Podcasts, Spotify, Google Podcasts, Facebook, LinkedIn, Instagram, and Twitter.

As a certified Gallup Strengths coach, I can provide you or your organization personalized coaching to discover and build on your strengths.

I provide workshops, presentations, and talks that inspire and engage through powerful language insights, and I pair those insights with practical applications for the lives of educators, learners, businesses, and faith-centered organizations. I’d love to share ideas with your organization or group, and develop an event tailored to your objectives.

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Thank you for always focusing on the possibilities, opportunities and the power of language and what it can do for us individually - and collectively!

Elizabeth Mack

If you've never done #cliftonstrengths, yourself or with your team, don't wait any longer.  Norah Jones of FLUENCY CONSULTING is the one and only to do it! It's all about your super powers: finding & using them to affect positive change in the world. What's not to love?!

Elizabeth Mack
Founder and CEO / Freestyle Languages


Yes, @NorahLulicJones definitely has the talent of "bringing out" the best in others or allowing them to showcase themselves in the best light! Thank you for directing the spotlight on others who have great stories and talents to share with others. 

Lisa Fore


Your podcasts are exceptionally relevant and applicable, thought-provoking and insightful, easy-to-follow and enjoyable!  

Paul Sandrock
Senior Advisor for Language Learning Initiatives / ACTFL


You have an immense talent to draw the best from your participants. 

Richard Brecht


Norah knows how to LISTEN - she really "hears" the message - and the interview is richer because of it.  New questions come from the hearing. 

Terri Marlow


[Introduction of guest (bio) and of podcast episode]

Norah Jones:                   I have in my workshops a modified Maslow scale. I am a bear of very little brain. I can only do three things at a time. Survival first, then belonging, and only then competence. And I believe curiosity comes at the level of competence because we can trust that our curiosity might be satisfied. Until we know we’re safe, until we feel a connection and feel that we can trust, I don’t think we get there. Why would we?

Matt Bailey:                    That answers a lot of questions and it reinforces a lot of what I’ve seen because one of the benefits of what I do is I’m able to go to so many different companies. I think throughout… In a non-COVID year, I’m probably in about 30 to 40 companies. During COVID, now and doing virtual training. And it’s very interesting because someone will ask me how a training went. My answer now has morphed because I can tell the culture of the company by how the training goes.

And what you said about being safe and valued, questions, concepts, freedom to speak, are so evident at companies that have an amazing work culture. When there is a negative work culture, there are barely any questions. People are afraid to ask questions and you can see people start to ask something, but then stop, rephrase, and go safe. They’re not going to put themselves out there. They’re afraid of looking incompetent. And culture, the culture of the company can absolutely squash someone’s ability to ask questions, or it can enable them to flourish with that. I love how you said that if they feel safe and valued, then curiosity is there. Without that, there’s fear and almost in some cases, a fear of reprisal. It’s just so evident, especially when I’m there on site and I can watch what’s happening. It’s a little less in Zoom, but I can still pick it up.

Norah Jones:                  Yes. I’m sure you pick it up very well with your skillset, no question. And our vulnerabilities levels can be fairly easily crossed, if you will. We don’t have to embarrass ourselves tremendously or feel completely crushed in order to want to avoid that pain. We don’t have to touch a full speed electric wire. We just don’t want to be near something that stings. And that’s absolutely critical to making sure that people indeed feel that they have hope in their participation. You, with your background will almost certainly know who it is that said this quote if I’ve got it anywhere near to its original, but you should be very wary when your best people in your company fall silent.

Matt Bailey:                    That is, yeah. That’s powerful. Very, very powerful. And yeah, unfortunately it’s something that I have seen a lot of times. We used to call this the HIPPO, the highest income producing person’s opinion. That squashes-

Norah Jones:                  I like that.

Matt Bailey:                    … all conversation.

Norah Jones:                  Isn’t that true? Yes. I think many of the listeners will be able to imagine something right now. Yes, I think that’s a very nice image you just provided, Matt.

Matt Bailey:                    Yep. That’s what it comes down to. So that is so key. I would not have put curiosity in that organized response that you gave, but it makes so much sense because in order to be curious, you have to have that safety, that ability. I would say almost the permission to be curious.

Norah Jones:                  Absolutely.

Matt Bailey:                    So, the next step would be formulating a question. So, I have the curiosity. How do I formulate a good question?

Norah Jones:                  Oh my goodness. Boy, you have put such pressure on me. I love it. Well, I do think that we together have reiterated some of the things that we would avoid. For example, kind of a question where there can only be a factual answer. Those have their place, but formulating a good question provides an option for the why and the imagine start. I think a good question does not necessarily come out in the question format right away. Imagine that you are an indigenous person who is seeing a ship come over the waters, a ship like you’ve never seen before. And you can see that there look like there are figures on board the ship. When these figures land on your shore, how will you respond and why? What do you already know of responses that have happened in history? You can see I’m going to be a social studies teacher here for just a second.

In what ways do you find these to reflect what you can imagine happening in your life? What are some of the ways in which these actions, this landing on your shores has happened in your life? What were your reactions? How do they relate to others? It’s kind of an ongoing… And each one of these, of course, is done after separation of time and part of what that implies, what I just did with that list, by the way, Matt, as evocative or non-evocative, as you may have found it is that when the students, when adults begin to answer questions, I believe that the best thing that happens is that the person that asked the original question evokes a question next based on the response heard, rather than on something planned. That questioning, I believe, at its best is open-ended response that evokes the experience of the person asked, evokes their responses, as in their responses to the experience in their past, evokes their emotions, evokes their beliefs, evokes their opinions, yes.

But opinions based on experiences and that when they begin to answer, then I feel that the strongest questions come then not from an array preplanned, sort of like I just did, but from then that dialogue that happens. And this can happen in a classroom because some of the most effective questioners, especially when trained and they usually are trained this way more by their emotions than by us as instructors, the others that are in the classroom, the others that are in the meeting, when given permission to think of open-ended questions, will be the best questioners for follow-up, because they’ll be listening then not just with my response, but with their responses, with their histories. And they’ll continue to ask questions. And then frankly, whether you, Matt, as a leader or I, as a teacher, whatever our roles might be, that we are able to help to train those questions.

So, a person says, “Well, were you happy?” Perhaps we can open up that question to say, “What were some of the emotions that you had?” And train all the rest of the people in the room to be questioners, exponentially more effective than just guiding it ourselves. So those two aspects, well three aspects I suppose, open-endedness which we repeat, listening carefully so as to not necessarily have a [inaudible] from which we read and then inviting and training others to be our co-questioners. In the same approach, I think exponentially grows the ability to have excellent, insightful answers that have meaning for people.

Matt Bailey:                    Wow. Yeah, this was great. Very, very good. It causes me to think of the Socratic approach of… And that was one thing that I… So in college I took a number of courses on persuasion, marketing. And one thing I loved is my professor used Aristotle’s Rhetoric, and that I think is what started a lot of appreciation for the classical. But then when I started reading some of Aristotle or Socrates and some of the dialogues there, what fascinated me was his ability to come up with really good questions. When I first started reading, what hit me the hardest was, I don’t think I would have asked that. Rather than, this is supposed to be the wisest man ever. He’s not answering anything.

Norah Jones:                  He’s not answering anything.

Matt Bailey:                    He’s not giving any answers, but the ability to dissect the question that was given to him to properly understand the motivation of the question, the terms of the question, and it really gets down and a lot of times, and I get into this in the business realm. What do you mean by, fill in the blank?

That I have learned more and more is so critical. Give you a business example. One of my classes I taught the other day, we were talking and someone was saying that, “Well my job is to provide good leads for the business.” And I said, “Okay, let’s stop here,” because now all of a sudden my Socratic, it’s all kicking in and I’m like, “What do you mean by good?”

And now, “Is it good?” Are they defining good by you got a lot of leads, so by the amount of leads? Do you find good by the quality? Their high quality, meaning you don’t have to work them that hard. They’re going to turn into sales. Or are they defining good by the cost that it took for you to generate those? And immediately I was so happy because they got it. They understood immediately what I was going for. And all of a sudden now they realized, “This is why my reporting is being missed because I’m reporting on aspects that are not important to them. I’m filling up this report.” And she said, “He is most concerned about cost, and so my reports should focus on cost.” And I’m like, “Yes. Yes, she’s got it.”

Norah Jones:                  She’s got it.

Matt Bailey:                    But what it was, was, “Let’s pull this adjective apart. What do you mean by good?” And just by defining that, it transformed her understanding now of how I report, what I’m looking at, how to answer the right question.”

Norah Jones:                  I love that story. One of my podcast guests is a professional philosopher for whom Socrates was the game changer of her life. And perhaps I should be careful as I admit this in front of [inaudible]. But the reason that at least she spoke of why Socrates had to drink himself to death, if you will, was because unlike others, other philosophers, he believed in exactly that process that you just experienced, namely everyone is an expert or there is no expert per se. That each of us has an ability to contribute and that goes against the grain of hierarchical, societies of all kinds, not just ancient, but modern, not just philosophical, but financial. And I think that that’s an interesting thing to know that Socrates had those questions, that dialect going on in order to be able to demonstrate that and all the expertise really needed was right there in that wonderful question that you asked that evoked all of the answers that were needed to solve that problem. That’s great, Matt.

Matt Bailey:                    It wasn’t me. I’ve been in the same boat and I feel like now in… I don’t know… a good part of my career. I’m finally understanding why these misunderstandings happen, why people spend weeks putting together a presentation that nobody cares about.

Norah Jones:                  Nobody cares, yes.

Matt Bailey:                    And it’s always driven me up a wall that that has happened. And now I feel like I’m just starting to figure this out that because I didn’t ask the right question, I’m not delivering the right information. And because my stakeholder or my manager isn’t clearly defining what is it you’re looking for, what problem you’re trying to solve, but what I’ve seen just over the past decades, is just this lack of good questions or a lack of questions at all.

Norah Jones:                  And questions, again, we go back to the issue of vulnerability and of survival and of our sense of competence. And it will be interesting to see with the emotional, psychological effects of the pandemic, with some of the ways that people have both connected, but also been separated up over this time. Will our sense of vulnerability be expanded that we recognize that everybody has been in the midst of vulnerability, and so we’ll ask each other questions? We will listen to each other’s answers. We will follow each other down our paths and see where they head for a while and see if we want to walk down them and help each other along the way.

                                         Or will we find that we are more frightened, that we ask fewer why questions, fewer questions that evoke the curiosity, because we are recuperating emotionally ourselves? I’m not sure which direction we will find that we’re in. Probably a little bit of both, but we will need each other and we will need to ask each other questions and listen to each other’s answers and follow through more I think than ever.

Matt Bailey:                    That is beautiful. Well-stated and beautiful. I love that. Love that. That is a great, great summary. Norah, I’ve got one other question. I’m switching gears on you here because as a business educator, adult educator, why do I hate multiple choice questions so much?

Norah Jones:                  Well with your mind, that’s way too limiting. There are three choice answers, by golly, I don’t think. Seriously, you don’t like multiple choice questions, right?

Matt Bailey:                    Well, it was one of the things. I finished my master’s degree last year in instructional design and at the end of every unit, I had to take a 50-question multiple choice test. And I rarely perform well on those. And it was explained to me, because I’m an adult with life experience, it makes it more difficult because I see everything as it’s not black and white. But at the same time, I feel like it didn’t really capture what I understood. And so I was working with another education company and their challenge to me was, “What do you think is a good assessment of making sure someone understood something?” And I said, “It would be a final essay with one word, why.”

Norah Jones:                  There you go. [crosstalk] Exactly, exactly.

Matt Bailey:                    I just felt like the multiple choice doesn’t really show evidence that I learned. It shows evidence that I memorized a fact, but I just absolutely… And I have businesses all the time that want evidence that people learned and what they default to is a multiple choice test. Everyone defaults to that. Is this-

Norah Jones:                  Learning as factoids. Not only that, but there’s a presumption that those multiple choice questions are well written, that they include the sentence structure and the information needed in order to choose. And I would say, well, I may—by golly, that’s why I’m over here I guess with a microphone is that those multiple choice questions, which are unambiguous are factoids that are probably best left to just experiential use, and if that is the way that one would end a very important course, that it is shortchanging itself, shall I say.

That longer sentences always run the risk of being written in such a way as to be ambiguous. Well, it could be A or B, depending on whether and then you, Matt, and others that have understood the material can run all sorts of rabbit trails. And I will say that the internationally known assessments, which are most applicable then to young people, getting into schools all over the world are open-ended why type of examinations. And those that are not designed for the broadest use make more use of multiple choice and we’ll let that just float in the air for a while.

And then I will mention what I consider to be the finest examination I ever had, which was for my master’s degree, which is in linguistics basically. And I loved my professor who was a jolly wonderful man. So lively. We all just enjoyed everything because he was very all about the class all around. And for the exam, he called me in separately. And when I came into his room, his office, he was sitting behind his desk, which was quite large, no papers, sitting, looking at me, “Please sit down.” I sat down and he said, “Why am I giving you an examination like this?”

Matt Bailey:                    Oh, wow.

Norah Jones:                  And he didn’t hand me anything. He asked me to sit down and I said, “Well, you have divided yourself from me and you are using…” And I went into the metalinguistic and linguistic aspects of what he was doing. And as I talked, he got happier and happier and happier. My exam was to apply the aspects of understanding what linguistic and metalinguistic behaviors look like. It was fascinating and, I’m sure, hardly ever repeated in education, but it was great. And certainly inspired me to provide examinations that were open-ended to my students, visually based, and experiential. And so I’m going to concur your multiple choice… not phobia because you handle it, but… your distaste for multiple choice is I think well-placed. There are times for everything, but over-use of multiple choice I think is perfectly possible. And certainly from the point of view of getting down to the kinds of things we love to do as adults, not as rich as it could be, shall we say.

Matt Bailey:                    Oh, that’s wonderful. Wonderful, because like you said, defending what you knew in front of your professor I think not only did it inspire and excite you, I mean, you remember that. That is a full-on demonstration of what you’ve learned and being able to do that one-on-one. I mean, to me that reinforced the power of personalization of small -roup instruction of that there needs to be that mentor, that teacher is a coach, not… It kind of reinforces what I have always thought about, especially online education, is there is a place for the MOOC. There is a place for at scale, but when you want to truly show or demonstrate expertise, you can’t do that at scale. I really don’t see how you can do that. So while there’s a lot of online opportunities in that realm, where are you going to get that feedback? Where are you going to get that not only the ability to demonstrate, but the feedback and the coaching that only someone who’s watched you develop can provide?

Norah Jones:                  Absolutely right. And I appreciate that you used the word “coach” because if we could in fact consider teaching to be mostly coaching, that would be healthier. Also come back to what you were expressing about the nature of curiosity and the nature of learning here in this. That professor was actually the third, if you will, in a line of professors because I had a religion professor that I respected tremendously. He had a type of an examination that was like fill in the blank. I don’t know if he actually used any multiple choice, mind you. He wasn’t that kind of professor, but still more, should we say, discrete points, informational.

And he called me to his office and invited me to not take that exam, but to take one that was based on an open-ended single question. As a person who grew up in an education system where I indeed wanted to perform and perform well, called a person that was always trying to get an A, I turned him down and the look in his eye I never forgot. I took his regular exam, but I probably learned more about myself that day by taking that regular exam and then going and thinking about what he had asked me to do that I turned him down about. There was a vocabulary word that he used that I felt a little weak on and it made me panic.

I spent time studying that word, not because I was going to see him again, not because he was going to ask me that question ever again, but because I was mortified that there was an opportunity for me to have reached out and tried something with a coach and I turned him down. So when I think about, in our classrooms, in your work, that if a person is not yet ready, that we nevertheless through our coaching, through the opportunities that we provide, may not be in front of us, the next person down the road might inherit this person that has been in front of us and has recognized that there was a freedom that was offered there through an open-ended question, through an engagement with curiosity, through a real entry into what you’re talking about, Matt, what you’re solving, what the businesses need, [inaudible] my education need.

That there may be somebody in that room that failed to act in front of you, but by watching you and learning from you and seeing your coaching and your patience and your ongoing vulnerability yourself, is ready for the next time that it comes up. The seed is planted. I believe in that 100%.

Matt Bailey:                    Wow. It reminds me that that was actually I think a major point in… I’m trying to think. It was a book called Reclaiming Conversations. And I am trying to think. She is a professor at MIT. Oh, it’s escaping me right now, but she did an analysis of online learning and MOOCs and showing the completion rates being very, very low and then analyzing what made it different to the classroom experience. And the biggest point that she made, and it was surprising, but you just nailed it. And the biggest difference was watching the professor of the course take questions and how they handled, responded, thought, and wrestled with them and then answered. So it wasn’t so much the answer itself, but it was the student witnessing how the professor, because in a text or a video format, there’s…

                                         You brought this up earlier. One of the first things you brought up, the time. They witnessed the professor formulating the response and in doing so, it motivated them that, “I can do this.”

Norah Jones:                  I can do that.

Matt Bailey:                    She points to this as an issue with technology, that the technology forces an immediate answer. Even on a discussion board, if you read a discussion board, you’re seeing things as they exist now, not in the time it took for people to formulate, post, respond, and even… That’s the discussion board. That’s 10 years ago. Now we’re pushing into immediate conversations, responses, emails. That’s one of the big things I tell people is, “Just because you receive an email does not mean you have to respond [crosstalk].”

Norah Jones:                  Amen, brother. Amen.

Matt Bailey:                    Email means you have time to formulate a response. Business communication needs to slow down. But that was fascinating to me because I would never have guessed that as a major factor affecting education, and yet you just brought that right out. Is watching the coach, the instructor, the professor as they consider and formulate the answer as being such a key part of the learning experience and the question asking experience.

Norah Jones:                  You’ve reiterated the importance of the relationship. There can be no communication without relationship. If we go back to that storytelling aspect, the part that everybody has a story to contribute, that they learn how to tell their story and learn how to contribute stories and questions by observing. And so that coaching is ongoing. I really appreciate your sharing that book, that concept with me right back. I love that because it is that… Human language, whether it’s the culture of the classroom, the culture of business, the cultures of communities, of different ethnicities, of different nationalities, different experiences, all of our languages and cultures are a matter of listening to be able to ask questions, to be able to receive first responses, and then follow up because of the listening and the opening.

That’s also how we get to folks that by the time that they’re interested in becoming employed, have a skillset in speaking and writing, because they’ve been practicing this as human beings purposefully. Not just for academic, but because they’re human for years.

Matt Bailey:                    Wonderful. Absolutely. I think it would make a lot of hiring managers very happy to see students like that.

Matt, let’s follow up. Let’s make sure that those who’ve been, I know, fascinated by this wonderful conversation and I’m just so excited to share your insights that broaden the conversation about conversation and questioning. How can people learn more about you, Matt, what you do and how they can contact you?

Matt Bailey:                    All right. Thank you so much, Norah. I can be found at sitelogic.com. That’s S-I-T-E, sitelogic.com. Again, a hearkening back to Aristotle. So that’s where that name came from. But at SiteLogic, I have links to my podcast. My podcast is called the Endless Coffee Cup. It’s all about conversation. And also my training site is there as well, where I offer online training, but also you can contact me for organizational or business training as well.

Norah Jones:                  Matt, it’s been a great pleasure. Thank you so much for sharing these insights and endless coffee cups appeal to everyone. So thank you.

Matt Bailey:                    Absolutely, Norah. Thank you. It has been a pleasure and a joy to talk with you today.

[End of conversation]

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