‘Good Question.’ — Entrepreneur Addiction #41 with Dan and Nathan Rothstein

10+ min read • Jun 18, 2012 • Dan Bischoff

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I ran into the article, “Good Question” in the Boston Globe. It went into detail about how the best entrepreneurs knew how to ask the right questions, and did it often. I tracked down the authors of the article, and one of them also wrote a book, Make Just One Change: Teach Students to Ask Their Own Questions about teaching Harvard students to ask the right questions. The principles they discuss can help every business owner find the right answers — which is not as important as asking the right questions. We had a great interview about the process of asking questions, which in a way was ironic — we asked a lot of questions about asking questions. I think you’ll enjoy this interview:

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Transcript from the Podcast Interview

Patrick Wiscombe:  It’s the entrepreneur addiction podcast episode number 42. My name is Patrick Wiscombe. Dan Bischoff joins me for the podcast, the director of human communications. How are you sir?

Dan Bischoff:  Good.

Patrick Wiscombe:  You know, I’ve been busy transcribing the podcast. Can I just say how long it takes to transcribe a podcast?

Dan Bischoff:  It does take a long time.

Patrick Wiscombe:   I knew what I was getting myself into but I had forgotten just how long it takes. Coming up on today’s edition on the entrepreneur addiction podcast, we are going to be talking to two guys, Dan Rothstein who’s the author of the book make just one change teaching students how to ask their own questions, and we are going to be talking with the son of Dan Rothstein, Nathan Rothstein, and both of them are joining us via Skype this morning. How are you guys?

Dan Rothstein:  Very good.

Patrick Wiscombe:  Dan, you are in Massachusetts?

Dan Rothstein:   In Cambridge, Massachusetts.

Patrick Wiscombe:  Okay, and Nathan where are you?

Nathan Rothstein:  San Francisco

Patrick Wiscombe:  And of course we are in Salt Lake City. It sounds like you’re right in the studio with us. Guys, let’s get right into this. Let’s talk about your book, make just one change teaching students how to ask their own questions. I guess the first question is why did you even write the book?

Dan Rothstein:  Well, it’s interesting. It seems so obvious, doesn’t it? How can you not connect questions to learning? We expect questions to be connected to learning but its one skill that is simply not deliberately taught. Students actually come into school quite experienced in asking questions when they are very young, trying to make sense of the world is to ask lots of questions. But, something happens in school that seems to diminish their ability to ask questions and by the time they leave at the age of 18, they are asking very few questions and it’s a shame because the key to learning, the key to problem solving, the key to figuring out where you need to go, what needs to be done is being able to ask your own questions.

Patrick Wiscombe:  Now, we brought you on here because I originally found a Boston globe article related to this whole subject, to entrepreneurs and things. How does this asking questions and learning relate to small business owners and entrepreneurs?

Dan Rothstein:  Nathan, you want to address that?

Nathan Rothstein:  Sure. It’s funny because I was actually in a workshop yesterday in San Francisco done around the lean start up principles and they walked us through a process where we identify what the priorities are in our business and what assumptions we need to test what questions we need to ask to learn from the hypothesis we are setting up about our business. So, in the lean start up, Eric Reiss talks about so many times entrepreneurs ask the wrong questions. For example, they ask would you use a website like this that has not been built yet. So, the lean start up principles is about your MVP, about getting your product out as quick as possible and asking customers to use your product and ask questions about the product that’s in front of them. So, it’s expected that we are supposed to ask the right questions and we are supposed to prioritize our assumptions. In a startup, you don’t have the luxury of time. You need to really be deliberate about what questions you’re asking so you can adapt quickly but there’s no process for learning how to ask those right questions.

Patrick Wiscombe:  Why is that skill, why is that not taught to people as they grow up? You kind of address a little bit on the intro. What is that problem that we are seeing with that skill not being there and why it’s not being taught?

Dan Rothstein:  I think the reason the skill is not taught could be one of two reasons or maybe perhaps both. One is it might simply be assumed that everybody can could it. It seems too obvious. It’s part of our daily conversation. It’s part of our vernacular. We just don’t stop to think about how do we get better at asking questions? So, it may just seem too obvious. The second one is quite different from that. It may seem too difficult. How do you teach this skill? To this question you asked, how do you teach it? In a sense, what we have been working on is a very vigorous, open, but vigorous process that allows people in a very short period of time to climb a very sharp learning curve in their ability to ask their own questions. I can basically describe the core elements of that to you.

Patrick Wiscombe:  What are the core elements?

Dan Rothstein:  The core elements is that you first need to find a question focus. Very often, you see this a lot in education, you see this a lot in what consultants do with companies, is they will ask you a question to get you thinking. So, they are going to use a prompt, they are going to use a question to prompt you to think. So, what we’ve done, we’ve turned that around. We say what you actually need to do is design to name a problem, name a concern, name an issue, a topic and that becomes your question focus. It’s not a question to you but it’s going to be the focus for your questions and then the process begins by having people first look at a set of what we have come up with that we call four rules for producing your own questions. they include, asking as many questions as you can, not stopping to judge, analyze, or discuss any questions, to write down each and every question to make sure that you don’t skip one, even if it seems similar to the one that came right before it, and to change any statements into questions. it’s interesting because what we have is that you create 100 rules for asking questions or try to walk people through a process but what we are always after is what’s the minimum number, the simplest way to do that.so, what we have seen is these four rules seem to create the right structure and process and environment for people to begin to ask questions. So, that’s the first step, we present the question focus to them. The question focus might be identifying our market. It might be reducing costs. They might have a specific question focus there. But instead of my asking you questions about how you can reduce your costs, I’m going to present them to you and then you’re going to use those four rules for producing questions to generate a list of questions. Then we do something interesting, at that point we ask people to take a look, once they generated their list of questions, we ask them to look at whether they have both open and closed ended questions. Closed ended questions can be answered with a simple yes or no. you know, do we know how large this market is? An open ended question requires you to get more information. How can we get information on how large this market is? So, it changes the nature of the information you’re getting and the answer that you get. So, we ask people to take a look at that and these, again, seem fairly obvious. It seems like we kind of know that when it’s presented to us but then when we ask people to do something with those two questions, they find it very challenging. We ask them to change their closed ended questions into an open ended one and then their opened ended one to a closed one, just to get a feel for what its like to change modified question and to look at the different kinds of information that you could get.

Patrick Wiscombe:  Do people struggle with that, how to ask an open and closed ended question?

Dan Rothstein:  They sometimes noticed that they asked too many closed ended questions. Then they struggle from going to closed to open. When they actually practice changing one to the other, you can see their ability. It’s almost as if their question asking muscle in their brain is being to be developed as they manipulate the questions, they play with them, begin to look at them from different angles. So, once they have done that, we ask them to prioritize their questions and to think back to the question focus and for them to look at their list of questions and choose the top three questions from that based on what’s going to be most helpful for them in looking at their question focus. What very often happens is, it’s so interesting, is that they either go through their original list of questions and they say well, I actually would like to add an additional one now that we’ve done this thinking about it. Or, they choose one of the questions they changed from open to closed or closed to open as one of their priority questions. What that means is their priority questions, very often, at the end include a question that they did not have on their original list of questions. When we ask them, what did you learn, that’s one of the things they name as most significant. We never would have gotten to this priority question had we not used this process.

Patrick Wiscombe:  Yeah, and preparations we had for this, in our emails back and forth, you said without this process you might miss the obvious challenges, opportunities, and some hidden gems that you would have never gotten without it. I thought that was an interesting point you made too. What made you realize that there was a real problem with this? Was it something that you experience personally? Was it a business that you started? What prompted this whole book?

Dan Rothstein:  This is Dan, I probably should address that and then Nathan can talk about how he’s taking it to a new level and applying it to the startup world.

Patrick Wiscombe:  Okay, go ahead Dan.

Dan Rothstein:  The origin is very interesting because the source for this idea comes from people who are generally not seen as people who are going to be the source of innovation and new ideas and new thinking about education or business. I was working in a city in Massachusetts on a dropout prevention program and it was an effort to involve parents in the children’s education. The parents were saying we don’t go to the school because we don’t even know what to ask. So, we thought, they named the problem, let’s solve it, let’s give them a list of questions. And in a sense, we were doing the same thing that dozens of very good business books do that they try to help entrepreneurs and business leaders by giving a list of questions. But it’s an entirely different matter altogether, to help people learn how to ask their own questions. So, then we said, how do we do that? And we realized, whoa, it’s not that easy, how do you teach this skill? You can’t teach writing in one day, in one session. You can’t teach the skill of reading in one day or one hour session. How do you teach this lifelong sophisticated thinking skill in a short period of time? And that’s basically the work of the right question to answer to and the work that we have been doing around the world is helping a wide range of organizations and programs and businesses in many different fields to improve their ability to ask their own questions. That’s the origins.

Patrick Wiscombe:  So, that’s the background, how interesting. Nathan, how have you implemented asking the right question? Your dad was talking about taking it to the next level, what have you done?

Nathan Rothstein:  I think it’s interesting in talking about assumptions and testing out assumptions as why this skill is maybe not taught because everyone assumes that people know this skill. in business, especially in the lean startup methodology, you can’t really assume anything in the marketplace that you have a hypothesis but you need to test it out and then through the date, you have to ask questions to understand, what are we learning from this and how do we scale something that’s working. So, my work right now is we’re taking excess t-shirts and other clothing material and turning it into more functional and fashionable clothing accessories. We are doing that by, in the US, by paying people a fair and living wage to make this. So, we are turning excess into jobs in the US. What we are doing constantly, every week, is we create a new product or we create a new feature on the website and we look at what can we learn from this? And I think with entrepreneurs is we don’t know everything but the best entrepreneurs are able to find the people who know more than we do and connect the dots and ask them the right questions to understand how to move forward in the business marketplace. So, this is such an important skill and I see it’s also really interesting when you bring all these business leaders together and young entrepreneurs together in these conferences that are supposed to be about leadership training. What we always do is in practices everyone just come to listen to other people speak. We have so much intellectual capital there and everyone knows that the real things happen in the networking sessions. So, we could really do something more with these question formulating techniques and these networking practices in these large conferences. So, I think there’s huge potential there to kind of shift how we do leadership training and entrepreneurship training.

Dan Rothstein:  Nathan has pointed out something really interesting. Traditional structure in engaging or introducing people to idea is to basically sit passively and listen to someone

Patrick Wiscombe:  Right.

Dan Rothstein:  And what we are talking about is, I gave, here in Massachusetts, I gave a TEDxSomerville talk and it was the opening talk for the whole day. Basically, I tried to do something that Ted talks don’t really do and that is I tried to actually make it less about me and more about the audience syncing with me. It was very interesting because it’s difficult to do a Ted talk in a participatory format but I designed it in a way that it gave people a question focus, gave them opportunity to do some thinking, and then for them to see what the questions that they asked and how they compared to questions that another group had asked. So, in a sense, there are many opportunities where you can actually use a keynote address not as an opportunity for an audience to see and listen passively but to actually engage them in thinking exercises built into keynote address. So, there’s ways to both share the wisdom of the speaker but also to begin to tap that wisdom that’s in the room.

Patrick Wiscombe:  How did you do that? if you don’t mind me asking.

Dan Rothstein:  How did I do that?

Patrick Wiscombe:  Yeah. I mean, how did you implement a keynote into kind of a thinking exercise?

Dan Rothstein:  Right, it is a different module, there’s no doubt about it.

Patrick Wiscombe:  That’s pretty intriguing.

Dan Rothstein:  Right, intriguing is a nice word for it.

Patrick Wiscombe:  I mean that in the kindest way.

Dan Rothstein:  Right. By the looks of the faces by some of the people in the room, I’m not sure they thought it was intriguing. they might have been saying I’m ready for a good nap, put them to work.so, basically, it’s introducing them to the question formulation technique that  we have developed here and saying we are going to look at a problem that’s common to all of you that you have experienced either in your work or your life and we are going to use these rules for producing questions and I’m going to have you do some thinking and it might be thinking to the person next to you, it might be a cluster of people, it might be on your own but I’m going to be sharing something very precious with you, which is my time as the speaker. You don’t get many speakers that are going to give up some of their time acting at you and I’m going to turn it over to you because you’re going to see that you figure out some of these things on your own. so, it’s basically establishing the respect of the speaker for the amount of wisdom that’s in the room by challenging them, presenting them with a question focus, putting them to work, having them look at open and closed quickly, get some feedback from that, have them hear different perspectives, they are going to hear questions from other people that they had never thought about or would have never thought about on their own, and then weave that into the particular theme or topic of the keynote, on how does that inform our thinking about this.

Patrick Wiscombe:  I want to switch gears a little bit but what are some of the examples that people have done as well? In your article in the Boston globe you mentioned Zuckerberg a little bit. What are some of the examples that you know of?

Dan Rothstein:  There’s a book by Peter Simms called little bets how breakthrough ides emerge from small discoveries. He has a whole chapter on questions are the new answers. You can find in there examples of people in different fields. Muhammad Yunus who won the Nobel peace prize from micro enterprise. It’s an example of somebody that they point to who was asking questions about what he was observing around him that other people were missing. They talk about how Steve Jobs also was the veracious questioner and how entrepreneurs are most successful when they are veracious questioners. So, you can see people at the top of field, Zuckerberg, Jobs, Yunus, Nobel Prize winners, who are really adept at doing this. And I think a part of what we’re trying to argue here at the right question institute is you can actually democratize this skill. You can make it available to more people so you’re not dependent on one brilliant visionary leader to be asking the questions.

Patrick Wiscombe:  I would say Steve Jobs would definitely be that person but what about main street business?

Dan Bischoff:  Bob’s Pizza

Patrick Wiscombe:  Yeah, Bob’s Pizza.

Dan Rothstein:  That’s right.  In the sense, the work of the right question institute is to actually make this strategy available so all people can easily access it. People come to our website, rightquesion.org, and they can sign up and download, for free, the actual question formulation technique. If they want to go deeper into how businesses use it, how business could use it, then the book that we have is for educators but if business leaders begin to see themselves as part of their job is actually educational, how do they get their team members, their company, their business people to start thinking for themselves, then they could begin to see themselves as having an educational role and in the book, they can go in depth into how do you design a  question focus, how do you use this process well so that your making sure that all voices are being heard. So, it’s a book for educators but business leaders, who can begin to see themselves as oh, our work here includes education, developing people’s capacity to think for themselves, they can find it, use it as a resource as well.

Patrick Wiscombe:  What kind of people do you need to surround yourself with to get good answers? We talked about asking questions but is there an answer to making sure you get the right answers as well?

Dan Rothstein:  Well, I think, you know, I was thinking about that. You also asked me about what’s more important, the right questions or the right answers. It got me thinking about that in a new way and I realized that there are a number of right answers that people can tell you, which is find the new revenues stream or reduced cost; those are answers to certain problems. But, in order to get to the right answers, the skill that you really need is the right question. Peter Drucker, himself, said the problems in business are less about finding the right answers and more about knowing how to ask the right questions. So, what you need to do is, and this is part of what we have seen, is that you need to use some rigger in your process. I think we have all been in meetings where a question comes up and you spend two hours on question and at the end of that, what do you conclude? Oh, that wasn’t the right question.

Patrick Wiscombe:  But is that productive? To ask wrong questions.

Dan Rothstein:  Exactly, that’s not productive. so, what we argue is that if you use this rigorous process, what’s seems like a detour, which is spending time on finding questions, actually winds up being a short cut. That’s the real shift here in thinking about the value of questions.

Patrick Wiscombe:  You quote in your article too, Robert Steven Kaplan a Harvard Business professor about having the courage to ask the critical questions and I think about in that meeting, why does it take courage or some guts to ask some of those critical questions?

Nathan Rothstein:  Well, one thing that I saw yesterday through this exercise that we did, they asked us to write down two questions related to our business that if these things don’t work, would our business go out of business. For us it was, do people want up cycled products and if people don’t want those, then we don’t have a business. It takes some courage to ask those questions because you have to be really honest with yourself but they are the right questions to be asking because you don’t want to be wasting resources, you don’t want to be taking an investment for a business that may not be able to fail but if those are answered correctly and the marketplace accepts them, then you have a thriving business.

Patrick Wiscombe:  Do business owners sometimes have their business goggles on, in a sense where they are in love with their idea or their business that stops them from asking those right critical questions?

Nathan Rothstein:  So many people talk about the founder, failure of the people who start this business who can’t see beyond their idea. In business, it’s really not about an idea, it’s about execution, and it’s about going through this process of testing out assumptions and finding something that really sticks and there is no overnight success. Its five years of how long you can extend the runway but you also don’t have a lot of time to be going down a path that may not be accepted by the market. So, you have to be really deliberate about what test you’re having and not having an allegiance to an idea that doesn’t work.

Patrick Wiscombe:  Not building something that nobody wants.

Nathan Rothstein:  Exactly.

Patrick Wiscombe:  You mentioned something about asking the tough questions or the, what was the phrasing Dan? Was it painful, not painful questions but the critical questions.

Dan Rothstein:  Yeah.

Patrick Wiscombe:  So, if you’re asking the critical questions or, Nathan, to use your words, being truthful with yourself, if you’re not answering those critical questions, that means you’re not on the right path?

Nathan Rothstein:  Well, I think you can go down a path but what Eric Reiss talks about is well, we created this platform that nobody wants and everybody talks about how we learn from failure but what we really learn is we learn that people don’t want our product.

Patrick Wiscombe:  So, whatever questions you ask it’s going to send you down a path, one way or the other, right?

Nathan Rothstein:  Right.

Patrick Wiscombe:  So, it’s important to ask the right questions to send you down the right path. That seems critical to everything an entrepreneur might do.

Dan Rothstein:  This is Dan here. I just want to jump in on this because in the __ spoke on switch, how to change things when change is hard. They talk about the value of scripting some critical moves when you’re trying to give some direction and what Nathan presented there is the problem is that if you’re not asking the right questions, you’re not asking the critical questions, you’re going to be missing something. The reason why we created the question formulation technique is that it provides a script that people can easily use. But, what’s really interesting is that within this script, it’s not telling you what to think, its creating a process for you to do that thinking.so, you’re going to get better at accessing what are the right questions for you and this is about the dependency on paying for consultants to comes in to ask you questions that you could learn to ask yourself.

Patrick Wiscombe:  Okay. Now, can you ask too many questions?

Dan Rothstein:  I think so.

Patrick Wiscombe:  And where do you draw the line? I know that’s kind of a vague question but is there such a thing as asking too many questions and can you over analyze?

Dan Rothstein:  Well, it’s interesting. I’m not sure about the over analyze part but I actually think that one of the problems with traditional brainstorming is that it can just take you off in lots of different directions but it doesn’t really leave you with any clear sense of where you need to go or what you need to do. So, part of what we’ve built into this process is a time limit that we encourage people to use, and it could be flexible, but to basically put a time on the first step of producing questions because that’s when you’re doing thinking in a certain kind of way, it’s called divergent thinking, you’re thinking in many different directions, but, you then need to cut that off. you need to stop the divergent thinking and begin to do convergent thinking to begin to converge, to begin to kind of narrow down, to shift, to look at the different kinds of questions, to prioritize your questions, and when you’re doing that, you actually, without being fully aware of it, your becoming more sophisticated in your understanding of the problem and the issue because your beginning to access which question do I need to answer first, which question is going to help me get information or an answer to another question that comes later? If I ask this question before I have the information that I’m going to get from another question, I’m not going to be able to use it. So, you develop a real sophistication very quickly about how to prioritize, how to sequence your questions. So, I think that you concern about if you can ask too many questions is right on target.in fact, Joan Acocella, a writer for the New Yorker and just wrote a book recently, talked about the problems in brainstorming and sometimes there’s a lot of efforts to promote brainstorming in business but it doesn’t necessarily leave you in a better place.

Patrick Wiscombe:  I’ve always been taught that brainstorming is good. Well, I shouldn’t say that I’ve been taught that. So, you’re saying that brainstorming is not necessarily effective?

Dan Rothstein:  That brainstorming as part of a process, as a step, can be useful. It’s basically what follows that. when Harvard education press came and asked us to write the book, I think that what they recognized was that what we have managed to put together in a very structured short limited time process, a way to get people to do divergent thinking, convergent thinking, and then there’s one other level of thinking that happens in the process, its metacognition, which is really thinking about your thinking. When your able name how you learn something, how you can use it, what you understand differently, you are deepening your understanding of where you need to go. So, brainstorming is not a bad thing but maybe brainstorming by itself is not that productive.

Patrick Wiscombe:  We’ve only got a couple more minutes with you because I know both of you have to go and thank you again to both of you for coming on this show. We are talking with Dan Rothstein and Nathan Rothstein, who is Dan’s son. Dan is an author of a book called make just one change teaching students how to ask their own questions. As we close it out, Dan you wanted to ask them a question.

Dan Bischoff:  There are a couple of things that I wanted to hit on before we’re done. I want to get some specific questions that CEO’s can ask their executive team and also managers can ask their employees to help their business move along. Maybe it’s a longer conversion that we don’t have time for.

Patrick Wiscombe:  You have 60 seconds.

Dan Rothstein:  I’m going to just give you a quick answer on that. There are lots of books that you can pick up that will have lots of good questions that you could be asking. There’s a book John Bradberry on six secrets to startup success that has some questions, a list of questions that you can be asking. But, the argument that we’re making in make just one change is that you want to develop the ability for people to ask their own questions. So, the question that I would ask, that I would encourage entrepreneurs to ask is how are creating a question-asking culture in our business. That’s going to take you further than any other list of questions.

Patrick Wiscombe:  So, when in finding employees, as part of the screening process before you bring someone on, do you want employees that ask questions during the interview that are genuinely interested in your business? Is that a good indicator?

Dan Rothstein:  It’s a great indicator

Nathan Rothstein:  if people aren’t asking when I’m interviewing people, whether its interns or bringing on people to come work for us, if they are not asking us questions about the business, then I assume that A, they are not prepared for the interview, B, they are not really interested in our business, and C, they are not the first hirers for a startup because you want people to think for their own and to go out and find things that you couldn’t find by yourself.

Patrick Wiscombe:  I think we will go ahead and wrap it up there. Where do you pick up the book?

Dan Rothstein:  I would like to invite people to, if they want to, there’s a code for 20% off, a discount, on the book that if they like to, they could send an email to [email protected] and we will send them that code so they can order it.

Dan Bischoff:  And the title is kind of towards students but it applies very well for business owners as well.

Dan Rothstein:  That’s right, and if a business owner begins to see that there’s an educational role for them in the business that we need to help out business do better thinking, then you can take the work of the teachers and you can immediately apply it to the problems and challenges that your facing.

Patrick Wiscombe:  Send your email to [email protected], did I get that right?

Dan Rothstein:  Yeah, one word, rightquestion.org

Patrick Wiscombe:  Alright, we have been speaking with the author of make just one change teaching students how to ask their own questions. Be sure to check out their website rightquestion.org. Our guest today, Dan Rothstein, who is the author of the book, and his son Nathan Rothstein, who is out in California at the seminar. Dan Rothstein, Nathan Rothstein, Dan Bischoff, the director of communications at lendio.com. My name is Patrick Wiscombe, be sure to pick up the podcast on lendio.com/blog. You can also pick it up at my website pw.com and you can also pick it up in a couple other locations, knrs.com on the Patrick Wiscombe page, and also in the text section, kind of a strange place for the podcast, abc4.com. So, for Dan, Nathan, Dan Bischoff, I’m Patrick Wiscombe. thank you for listening. We will talk to you next week.


Dan Bischoff