How To Ask Better Questions

Jim Frawley is the Founder of Bellwether, a community of people that get things done. He specializes in executive coaching, group coaching and organizational strategy. He has a unique ability to get people to accomplish what they didn’t think they could, and his clients are a diverse range of industries and styles, from Fortune 100 firms to startup entrepreneurs. 

He holds his Executive Coaching Designation from Columbia Business School and is certified to administer numerous neuroscience, behavioural and personality assessments.

His personal life is spread among three areas: he’s a big-time reader, a small-time triathlete and a full-time husband and father.

Episode Summary

  • What’s the laziest advice a coach can give?
  • Better questions will lead to better listening.
  • Understanding what a “question” is will lead to better communication
  • The intentional practice of asking better questions
  • ORID question framework



“When you ask a question with judgment, and not in a learning mindset or curiosity mindset, then you’re effectively making statements.”

“Let’s ask questions and learn something together.”

“Be vulnerable enough to recognize that you don’t know all of the answers. And that’s okay. That’s what questions are for.”


Change Your Questions, Change Your Life by Marilee Adams

The Art of Focused Conversation by Brian Stanfield

Guest Information

Website: www.bellwetherhub.com

Facebook Page: www.facebook.com/bellwetherhub

Twitter: https://twitter.com/bellwetherhub

Instagram: https://www.instagram.com/bellwetherhub/

LinkedIn: https://www.linkedin.com/in/jimfrawley/

Episode Transcript

Chris Ippolito 00:31 

Hi, Jim. 


Jim Frawley 00:33 

Hey there. 


Chris Ippolito 00:34 

How’s it going? 


Jim Frawley 00:35 

Fantastic, thank you. How are you? 


Chris Ippolito 00:36 

I’m doing great. Thanks for being a guest on the “Get Coached Podcast.” When we did our initial call, which I do with everybody, I asked you a question, which was, “What’s bad advice that you hear consistently in your industry?” And I was wondering if you could share what your answer was? 


Jim Frawley 00:57 

Yeah. In the coaching industry, and it was the first thing that came to my mind, I don’t know why it was, but the advice that people give on just working on your listening skills. When people tell you that you need to work on your listening skills, I feel like that’s just the laziest advice that anybody could possibly give you anywhere, any time. It’s just the laziest, easiest, 1990 sales coaching, horrible type of advice. Which, I mean, it’s not that bad, but you know what I mean. I tell people if a coach is telling you that you just need to work on your listening skills and they just leave it at that, I feel like you should just fire your coach. Because they’re not doing the work required that you’re going to need to get the real value out of it. 


Chris Ippolito 01:47 

Yeah. And it surprised me a little bit as far as it’s advice that normally on the surface level sounds like good advice, but I didn’t want to dig into it too much then because I was hoping that we could now. Do you mind digging into that a little bit as far as why do you feel that’s bad advice? And it sounds like because you feel like it’s very surface level and that it requires digging deeper, but can you share a little bit about why you feel that way? 


Jim Frawley 02:20 

Yeah. Coaching requires you to dig deeper, you pay a coach to dig deeper. And telling someone to work on listening skills, we all listen, we all have the capability to listen, and it’s not really that you need to understand what people are saying or anything like that. And I feel like when I see someone having listening skills problems, really the question you should be asking is, “What are the questions you are asking?” It’s not necessarily to focus on listening skills, but let’s go deeper and let’s say, “Do you understand how to ask a question? How are you presenting yourself in the question? How are you presenting this information that you need?” Because generally when you receive information from someone, the information you’re not listening to, it’s a response to whatever you put out. You need to explore what an individual is doing in order to elicit that response that they just don’t want to listen to. 


And I also feel it’s indicative of coaching in general, of you need to dig deeper. Right? Your goal isn’t to lose weight, you have to understand why a person wants to lose weight. Your goal is not just to want a promotion, “Why does this align with your value set of what you want to do for your career?” There are multiple layers that you have to go through in order to have a successful coaching engagement. 


Chris Ippolito 03:36 

Right. What would be some of the exercises or questions that you would take somebody through if on the surface it’s, maybe they even said it, “Oh, I just want to be a better listener”? I don’t know anybody who’s actually said that. But that’s perhaps the area in which they’re struggling, is in communication, we’ll say that’s what it is. What would be something that you would help them out with so that the end result is that they’re getting better responses to their questions, or maybe you’re helping them just develop better questions, what does that look like? 


Jim Frawley 04:15 

Yeah, I would say there’s two aspects to it. One, there is a book that I give to almost all of my clients, it’s called Change Your Questions, Change Your Life, it’s by Marilee Adams. She’s a doctor, I think she’s a professor down at Princeton. She’s made a business out of questions. And ultimately the first question I ask someone is, “Do you know what a question is?” And people laugh when I ask that question, but most people can’t answer it, “Do you know what a question is?” 


Chris Ippolito 04:46 

I couldn’t. 


Jim Frawley 04:47 

Right. And this book is really all about how you can ask questions to get whatever it is that you want. And the true definition of a question is a request for information where you legitimately do not know the answer. And that’s a very important part for questioning, is you legitimately do not know the answer. When you say something like, “Why the hell did you do that?,” that’s not a question. That is a statement with a whole bunch of context and everything else put into it. And when you ask a question with judgment, not in a learning mindset, a curiosity mindset, then you are effectively making statements. And it doesn’t matter what you’re listening to because the person on the other side of it is already receiving a judgmental statement, they’re not receiving a question. To lay a platform of “let’s ask questions and learn something together” is a very different way to approach any kind of communications issue. 


And that’s one aspect that I’ll do, the other one is just explaining how communication works. A fundamental communication model of two people, one sends information, the other receives it, and the person responds and you receive it, and visualizing how that actually works, and then understanding how the communication of questions and learning and curiosity will elicit better responses. We just take it to a whole different level and we can explore countless questions on saying, “What does this mean for you and what does this mean for you? And let’s talk about your experiences with Alice in accounting and Joe in finance and this person in legal,” and whatever. And they can bring their experiences into those individual things. 


Chris Ippolito 06:22 

Right. What would be some common mistakes that people make when it comes to better communication? Because it almost feels like that’s what we’re starting, the path we’re going down, is it’s just more about better communication by asking higher quality questions, and then also understanding how that conversation should go. When you ask a question, there’s a response, and then you go back and forth. But what are some of the common mistakes that people are making if it’s not necessarily being a “bad listener,” what are the other mistakes that they’re making? 


Jim Frawley 07:01 

Well, you hit the nail on the head as you were talk about it, you said the conversation doesn’t go the way that people plan. And it never does. We always have the conversations in our head before we go up, whether we’re asking for a raise, whether we’re saying, “I want this promotion.” And we have the whole conversation in our head with the boss, and then the first thing comes out of my mouth and they don’t respond the way that we had imagined it and all of a sudden we’re defensive. Okay? And once we’re defensive and our stress mechanism comes up, we’re no longer in a learning mindset and curious mindset, now we’re protecting our ego. And then all of a sudden our judgmental comments come back in and the whole thing just devolves. 


And when we talk about communication, and this is a skill that takes practice, is taking the ego out of the equation. When you talk about Brené Brown talking about vulnerability or Simon Sinek talking about his stuff, all this stuff is really about a curiosity mindset, being vulnerable enough to recognize that you don’t know all of the answers. And that’s okay, and that’s what questions are for. And the really good leaders that we see in organizations are the ones that are able to ask really good questions. And they’re not protecting themselves, they don’t have to be the smartest person in the room, they recognize that most of the time they’re not, and they’re able to tap into them and talk to them in a way that elicits the information that’s best for everybody else in the room. 


Chris Ippolito 08:21 

Right. If somebody’s really struggling with that aspect of it, maybe what’s the first step in the journey to improve that skill set, what would you say is that first step they should focus on? 


Jim Frawley 08:39 

Well, one of the things we always like to do in coaching is test new behaviors. And it’s going to take practice. In order to make this a true skill set and a skill of yours, and I would encourage people, this is one of the top skills that you can pull into your quiver. As we look at the new economy and the way that the economy is changing and the workplace is changing, questions are one of the most important ways that you can do this. 


And when we want to make a change there are two ways that we can do this. One is you have to be intentional with doing it. Understand what a question is and do your research on it, whether it’s reading the Change Your Questions book, or I’m sure there are YouTube videos out there on really good questions. Understand what a question is. The Art of Focused Conversation is another really good book, just understanding the different types of questions. There are books on the different types of questions. Which is amazing to me, that there are academic people who actually study questions, this is fascinating to me. There is information out there to teach you how to do this. Understand it and learn it, take the time to learn it. But then you have to be intentional and consistent in testing this out. 


One of the things I would do with my clients is tell them, “Pick your person.” Generally it’s a person you might have a good relationship with, I wouldn’t test it on someone new. But test out different types of questions. And then you go back into your cubicle or your office or whatever and you say, “How did this go? And what went well and what didn’t? And how did I feel?” Because when you’re making a change like this, whether it’s vulnerability and admitting that you don’t know the answer or you’re bringing this new aspect to the workplace, your emotions are going to drive a lot of this. You’re going to have to be in tune with who you are as an individual and you’re going to have to reflect on that. 


As you work through this and you test it out with this person or that person, immediately go back after the conversation and give yourself a little quiz. “What went well? What didn’t go well? Why didn’t it go well? How did I feel? Did I feel myself getting nervous at a certain point? Did the conversation change at a certain point? What could I have done differently?” Or, “What went really well?,” right? “And how can I try this again and again?” And through practice maybe you then evolve up to you take your team during a meeting and you’ve got the five people that report to you around a table and you start asking them questions and maybe test your questions there and see how that goes. And after the meeting you go back, “What went well, what didn’t?,” and do your recap. 


And that’s going to be the self-coaching that you can do, because this is something that you’re going to have to tap into. As your career evolves, your questions are going to evolve. The level of person you work with is going to evolve, your questions have to evolve. You’re sitting in the boardroom or the C-suite, the questions you’re asking are very different than when you’re managing a team of five people on the floor. This is something to work on on a regular basis, and constantly check in with your emotions, with your ability, and what you’re focused on in order to improve. 


Chris Ippolito 11:37 

Yeah, being intentional is obviously the number one thing if you’re going to develop any skill set. The more intentional you are, the more the results are going to start coming, especially if you’re going to be consistent with it. I’m just trying to think. I mean let’s use me as an example. I’ve worked in a lot of roles that required to ask quality questions, or else I just couldn’t solicit the responses that would help me actually help the other person. I’m referencing being a financial planner. And then now with something like this, being a podcast host and obviously just starting, if I don’t ask good questions, the content is probably going to stink a little bit. Right? What you’re suggesting, maybe for something like this, is I rewatch these episodes, I look at the questions, and then I dissect it a little bit, “Why was that a good question, or why was it not a good question? And what about it made it good or bad, or how could I tweak it or adjust it to make it a better question?” Is that what you’re suggesting? 


Jim Frawley 12:52 

Yeah. Remember, a question is ultimately about learning. And what you’re trying to do is you’re trying to learn about the other individual. When you think about the questions a financial planner is asking, it should be learning about a person’s situation. And when I talk to financial advisors and I’m working with financial advisors and I ask them what they do, they say, “Oh, we analyze the markets and we do this.” And I say, “That’s not what you do.” They say, “Oh, well, we do financial planning.” And I say, “That’s not what you do. What you do is you take away worry for other people. They’re giving you their money so that they don’t have to worry about it when the market tanks.” Their question for prospective clients is to understand what worries them and learn about the individual, and that’s being purely curious about another person. 


And this is true for promotions at work, it’s true about networking. This is how you network, you ask about other people, because then they will like you. That’s it, you don’t have to talk about yourself. You learn about other people and what they’re looking to do, and that curiosity, this love of curiosity, this love of learning will drive your questions wherever you go. No matter what you have to do, when you’re intentional, I tell this to people who want to start running or do whatever, the first thing you have to do is you have to learn to love it. That’s being intentional, you have to learn to love questions, you have to learn to love being curious about whatever it is. 


You can meet someone who works in a water tower, my wife is obsessed with water towers, she has so many questions for water towers. If you ever told her that you worked at a water tower, she would give you a laundry list of questions. She’s one of the most curious people on the planet. You have to translate that into whatever else it is that you’re doing, and being curious about another person’s job, what your boss is going through, what’s important to them, what’s important this week, and being curious. 


As you look back on this podcast, there is going to be a time where you sit there and you say, “I really wished I asked Jim that question because I was just thinking about that, I wish I asked that question.” That’s part of your learning, and that’s good. And through practice you just learn to ask the really curious questions. There really is no such thing as a bad question when you’re a curious person. 


Chris Ippolito 14:55 

Right. I’m somebody who likes systems and processes. Do you have a system or a process that you would teach somebody around asking questions or just becoming a better communicator? And I’ll give an example of something I’ve heard before, the acronym of FORM, family, occupation, recreation, and motivation. When you’re engaging somebody, you just try and find the answer, basically, to those four areas and that just helps with the dialogue. Do you have something like that that you suggest your clients do? 


Jim Frawley 15:35 

There is, and I’m looking back at one of my books. And I can’t remember the acronym off of the top of my head, but it’s sitting in The Art of Focused Conversation. And I take my clients through this. We’re at the end of the day, I don’t know why I can’t think of it right now. But there are different types of questions. You’ve got your objective questions, right? Purely on what is actually happening and what’s going on with the day, right? Purely matter of fact types of questions. There are reflective questions saying, “All right, well, what happened and why did it happen?,” and we can look back and do that. Then there are your interpretive questions. ORID framework, there it is, I’m going through it. ORID. Your objective questions, your reflective questions, your interpretive questions. “What did that mean for me and what did that mean for the team?” And then you’ve got your decisional questions which are, “All right, what’s next?” 


You start objectively, which nobody can get offended with, and you just say, “What is actually happening? Let’s talk about the facts,” and we’ll do that. Then we’ll get reflective and say, “All right, well, what happened to get us to this point?” Interpretive, “What does it mean?” And then decisional, “What are the decisions that we can make based on this?” And it’s how you can have a conversation with people on your team, but it’s also working through your listening skills in your head you can bring someone through these four steps, which takes emotion completely really out of the equation. It’s really a matter of fact curiosity pattern that you can go through, this ORID framework in The Art of Focused Conversation. You can do that just to bring people through, that is your system and process to bring someone through a conversation. 


Chris Ippolito 17:15 

That’s awesome, I like that. Because for me, it just helps me remember, something like FORM or ORID. And then when I’m in that moment, it’s a little bit easier to relay back to that, and then take me through the steps of what I need to do. Versus having this laundry list of questions that you’re trying to remember like, “I’ve got to ask this, I’ve got to ask that.” It’s more just what’s the subject that you’re wanting to learn about, and extract that information. And then the question itself, obviously it’s not that it doesn’t matter, but it’s not as important as long as you’re trying to get the information, extracting the information. 


Jim Frawley 17:58 

That’s right. You take the system, it’s your compass pointing north, to just saying, “These are the four areas I need to cover, this is the arc I need to go on.” And you don’t have to go in with 50 questions. At the beginning you may have to think through, “Well, what is an objective question? What is a reflective question? What is an interpretive question?” But eventually it just becomes a habit to say every conversation, “All right, objectively I get what happened. Now let’s think back. All right, what does this mean for us? And then what’s next?” 


Chris Ippolito 18:26 

Right. I like that. I was super surprised when you answered about listening better, and I’m glad. The conversation obviously went very different from where it was listening to just really improve communication and how do you do that. Right? 


At the end of every episode I want to try and find what’s that one thing that we can suggest the audience who’s listening do to improve, in this case it would be their communication. Would you suggest maybe the book or something? I almost want to keep it as small as possible. Like what’s that one tiny little action step that they can do that’s going to help them take the next logical step as far as improving their communication skills? 


Jim Frawley 19:17 

I give Change Your Questions, Change Your Life to almost all my clients. Read the book. It’s a very simple book, a lot of my clients hate it. They read it and they just say, “This is the cheesiest book I’ve ever read.” And I’ll say, “Well, did you change anything?” And they say, “No.” And I say, “Read it again.” And they come back and say, “All right, I get it.” 


It’s basically a story of a person going through coaching who’s having a difficult time at work. And it’s basically the conversation on how he discovers that questions will help a lot of his personal and work situations. It’s a little hokey, but it talks about learner and judger mindset. And the way that she frames that, I think, is one of the most impactful ways that you can recognize in the moment when you are moving to a judger and not being a curious individual. And she gives pivot points to come back to say, “I need to get back into learner, I need to get back into learner.” And that allows you to ask better questions. When I look back, I had one client read it, go through it, try it out with his team, and he’s very senior. He looked at me and he said, “This made me realize that I love learning,” and he wanted to learn more. 


It’s really, really impactful, the ability to ask questions. Because then the other nice thing is once you do it, all the pressure is off of you, all you have to do is ask questions. You don’t have to come up with the answers, everybody else has to do it. When you’re really good at asking questions, you’re good. The one thing I would say is Change Your Questions, Change Your Life, go read the book. 


Chris Ippolito 20:48 

Awesome, I’ll include that in the link for the show notes and description of the video. I’m assuming it’s probably a bit of a shorter book, because it sounds like it’s a bit of a parable. Right? 


Jim Frawley 21:01 

Well, you know what? It’s, I don’t know, maybe 150, 200 pages. 


Chris Ippolito 21:04 

Yeah. I’ll put the Amazon link. 


Jim Frawley 21:08 

And I think it’s double-spaced. 


Chris Ippolito 21:11 

It sounds a little bit like another book that I read where they’re trying to teach principles through a story, The Go-Giver. But yeah, I’ll check it out. I’m going to go and read it, I suggest everybody else do the same thing. 


Jim Frawley 21:26 

Beautiful, I love it. And I’d love to hear about it. And I’ll tell Marilee Adams that she owes me a cut when all of her books go skyrocketing. 


Chris Ippolito 21:34 

Awesome. Before we wrap up, Jim, was there any other questions that I didn’t ask you that maybe I should have asked and you want to add? 


Jim Frawley 21:44 

No. Look, the beautiful thing about coaching is that it’s about learning. And when you are able to learn, that changes your perspective on everything, whether it’s work, whether it’s home, whether it’s community. And being curious, this curiosity mindset, I’ve really embraced it. I wish that I had gotten more of this information earlier in my career, it would have changed the whole career trajectory that I’ve had. Although now it’s nice that I’m a coach and I really love what I’m doing. But learning and curiosity is really the name of the game and it allows you to be flexible in difficult times. When recessions happen or whatever, that learning mindset is what’s going to get you through and that’s what’s really helpful. 


Chris Ippolito 22:31 

Right. Yeah, I think that’s great advice. Maintain a curious mindset, maintain a student mindset, and you’ll be good for life. 


Jim Frawley 22:41 

I have a theory. It’s why kids are so happy, because they’re still learning. 


Chris Ippolito 22:44 



Jim Frawley 22:44 

Adults stop learning. That’s it. Kids are happy because they have this awe and wonder going around. Once you get over the age of 18, you know everything. And that’s why people aren’t happy. Get them to learn something, ask a question. 


Chris Ippolito 22:56 

Very true. If people wanted to reach out and connect with you or learn more about you, where can they go? 


Jim Frawley 23:03 

The best place is bellwetherhub.com, B-E-L-L-W-E-T-H-E-R Hub. It’s my blog posts. I’ve got events, mostly in New York City, I’ve got some up in Canada actually this year. Wherever I am, this is where I like to get people going. And that’s my outside-of-the-office, fun, coaching podcast, posts, everything. That’s where you’re going to find me most of my time, look for me on Bellwether Hub. 


Chris Ippolito 23:31 

Awesome. And that will be in the description and show notes, as well. Cool, awesome. Thanks, Jim, really appreciated it, it was a great conversation. I’m adding another book to my book list, I’ve just got a lot to read. 


Jim Frawley 23:45 

I’ve got a whole stack upstairs. 


Chris Ippolito 23:46 

It’s because I enjoy learning, that’s why I do it. 


Jim Frawley 23:48 

Well, that’s it. I’ve got three boxes upstairs. My wife was saying, “What the hell are all these books doing here?” I said, “I’m going to read them, I’m going to read them.” 


Chris Ippolito 23:54 

Nice, nice. Awesome. Thanks, Jim, take care. 


Jim Frawley 23:57 

Thank you, Chris, appreciate it. 


Chris Ippolito 23:58 



Jim Frawley 23:59