• Jul 24, 2020 | Most Popular

    Ep. 5 - Asking Good Questions: Part 1

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    Episode Description

    Journalists and sales people both have to build trust quickly, uncover the root of an issue, ask good questions, and listen effectively. These are all critical leadership skills as well. On today’s episode we’re speaking with journalist and best-selling author, Amanda Ripley, and Chief Revenue Officer of People Data Labs, Andrew Elliott. Not only are they masters of these skills themselves, they both teach others how to ask better questions. This episode has been split into 2 parts so that you can benefit from all the tips and tricks they share!


    • Amanda Ripley, Journalist & best-selling author
    • Andrew Elliott, CRO, People Data Labs

    Resources Mentioned

    Episode Transcript

    Katarina Jones: When people step into a leadership role for the first time, it’s common that they feel the need to prove themselves by having all the answers, offering opinions about everything, or by being the loudest voice in the room. I see that a lot in the first time leaders that I work with. Yet, anyone that’s been a leader for a while and knows that it’s just as important, if not more so to ask good questions and to listen.

    Asking good questions can accomplish a lot of different things. As your team grows. As a leader, you can’t know about everything that’s happening, it’s just not possible. So asking good questions can help you understand what’s most important for you to focus on. That way, you can make the important decisions from an informed position.

    It can help you understand your team’s needs and motivations so that you can support them in the best way possible. It can build trust and rapport. When people see that you’re genuinely interested in what they have to say and that you recognize the value that they add.

    It can help you get buy in to important decisions when people feel heard, and like they had an opportunity to contribute to the conversation.

    And finally it can empower team members to think for themselves and to come to their own conclusions, which in turn means they don’t have to rely on you so much for every decision.

    So as a business leader, it’s a critical skill. Yet most people don’t get trained how to ask good questions. So in today’s episode, we have two people who ask questions for a living. We’ll be speaking with a journalist and bestselling author

    Amanda Ripley:  My name is Amanda Ripley, and I’m a journalist. I write mostly books and long form magazine articles for places like the Atlantic. And I write now mostly about political polarization and conflict.

    Katarina Jones:  As part of Amanda’s work on polarization, she discusses asking questions that get more nuanced answers and the impact that that can have on combating polarization in the media. So I knew she was just the woman for this topic. And on the business side, we’ll be comparing and contrasting her perspective with that of a sales leader who spent his whole career learning how to ask good questions. And now he teaches other people how to do the same.

    Andrew Elliott:  Andrew Elliott, Chief Revenue Officer with a company called People Data Labs. We build out data sets for product managers and data science teams. I help organizations build out the people, the processes, and the programs to help drive revenue and really do that across the entire go to market motion.

    Katarina Jones:  Amanda, Andrew and I had such a great conversation that I had a really tough time editing this episode. I try to keep each conversation to around 30 minutes, but I wanted you to hear all the interesting stories that they told as well as the tips and tricks that they shared. So I decided to do something a little different this week.

    This episode has been split into two parts. We’ll wrap up halfway and we’ll pick up again right where we left off. So thanks for listening. Let’s see what the two of them had to say.

    Katarina Jones: Getting started, I always love hearing. How do you imagine what you do is similar and how is it different?

    Amanda Ripley:  You know, to the degree, I understand what it means to drive revenue, which is not a high degree because I’m a journalist and we don’t drive a lot of revenue these days. but I think probably we both need to build trust with people, whether that’s colleagues or in my case, mostly people I’m interviewing, or people you’re interviewing and help other people build trust with people they’re selling to.

    And that is a delicate craft. You know, that is something that nobody taught me well, and I still work on and I wish I had been taught it sooner in my career.

    Andrew Elliott:  I love that you touched on kind of driving towards trust. I think that that’s definitely a real key factor. Again, I’m not a journalist , but I suspect a lot of that is trying to get to the bottom of things, in an effort to, to truly understand whatever it is that, you know, we’re focused on in that moment.

    And to do that, you have to be deeply curious and, That’s not an easy thing to do. So you mentioned that and I want to really reinforce that. It’s like a lifelong bar that you’re always kind of working at. I think some people are predisposed to it more so potentially than others, but  it’s hard and it’s hard for a variety reasons.

    Partly because you have to practice active listing. And that’s not an easy thing to do, to actually hear the things people say. To be truly present in the moment and then consider whatever it is that they’ve said  and use these things to ask more, deeper questions. That are really designed to unpack this topic.

    Amanda Ripley:  Yeah, so it’s, it’s building trust, but it’s also being curious, right.

    Is what I hear you’re saying. And also  understanding things. So I think, yeah, that’s those three things are very, very similar. And I would agree that the questions are important, and I know we’ll get to some good ones, what I’ve started to realize is that the listening is more important. Even if I ask bad questions, which I try not to do, but sometimes I do!  If I’m genuinely curious and really listening, people are incredibly

    forgiving and grateful for that simple act of really listening, which again is something that I was not trained to do. And that I, I have learned only, I think I’ve gotten much better at it recently for various reasons, but it’s  I’m glad you brought listening up right away, because I think it’s a word that sounds really kind of small, but it’s a really, really complex thing.

    Andrew Elliott:  It’s the cornerstone to everything else. I love that you brought up curiosity already. you know, without listening, we can’t even understand and comprehend what the right questions to ask might be. You know, a funny thing that I’ll do, like when I’m interviewing a candidate for a role, especially within sales is kind of just ask the question, you know, when you think about sales, what does sales mean to you? What do you think of? And I’ll hear things like influence or persuade or manipulate or used car sales and all these different things. And, and for me, the way I think about sales and what it is for me, it’s, it’s just problem solving.

    And in order to understand the root cause of the problem, if you peel back all the layers one by one, and the only way to do that is with the right question. So you have to have a lot of curiosity. you have to listen and by doing that, some interesting things start to happen. You really engage with the people you’re interfacing with.

    You start to demonstrate competence, you establish credibility, and ultimately, what you talked about, Amanda,  this builds trust. And that’s literally where the term,  trusted advisor comes from. So, when you’re able to build  a practice around this, you can create a very consultative framework that starts to separate you from, kind of the fray, of all the other conversations that this person’s having with everyone else, which means you start to stand out,

    they might start to perceive you as someone who actually cares or at least is trying to make some effort to understand, and I think that goes a long way.

    Amanda Ripley:  Yeah, it’s interesting that you say that sales is about solving problems because,  as an outsider, sometimes I think, well, sales means trying to convince me that I have a problem that you can solve.

    Right. But what I hear you saying is that actually, ideally you want to have the freedom and autonomy to only solve actual problems. And I think that there’s an interesting parallel in journalism. Ideally in my work, if I call up somebody and I’m interviewing them and they’re not actually saying the things that I thought they would say, I need to switch what I’m doing, right? And that requires a level of, autonomy and trust from my editors, that most journalists struggle to have, right. So you’re assigned a story and you got to go out and like fill some holes and figure out a narrative arc and whatever, whatever. And so you end up not really listening or not quoting someone necessarily,  if they don’t do the things you thought they would do, which is the opposite of curiosity, right?  So, I don’t know if you see an overlap there, but I feel like there are probably some salespeople who either don’t feel like, or literally don’t have that kind of autonomy. And the same with, with journalists.

    Andrew Elliott:  It’s all about having an agenda. Right? So if you have an agenda, especially if you’re attached to that agenda, it’s probably going to be a lot more artificial and framed up than it is going to be, you know, kind of genuine and authentic. And, think it’s just that basic concept of engagement versus attachment.  You know, if you’re attached to the outcome, your process is gonna probably be a little bit skewed and will likely suffer as a result of that.

    Whereas if you’re just engaged in the process itself, but not attached necessarily to the outcomes. Ironically, and sort of, interestingly, you’ll likely yield better results in the process. It’s a simple concept, but not easy, right? And I think there’s probably like a life lesson in there somewhere.

    Amanda Ripley:  Yeah, no, there’s like a Buddhist Zen thing ,about not getting attached to the outcome. And when I talk to reporters about this, I don’t know if you have this experience, when you talk to salespeople about this. When, when I talk to reporters about this, they say, Oh yeah, that’s really nice for you when you write a book or a long magazine article, but like, I got to write three stories a day, you know what I mean?

    And I’m attached to the outcome. Like, I don’t, you know.  I think my challenge is to communicate the idea that you just said, which is you got to have faith that if you’re “engaged,” to use your word, rather than “attached,” you will get somewhere. It may be somewhere else, but like, you’ll end up in a more interesting place.

    It may not be the place you intended, but there’s like a leap of faith there. Right?

    Andrew Elliott:  A hundred percent. And I think there’s a really interesting parallel with, you know, I watch, like 60 minutes or some other sort of,  journalist elements out there and, and sometimes it’s so amazing and  it seems like it’s just so artfully  done so well.

    And then other times you can just kind of see, there’s these leading questions coming through and they’re driving for a, yes to these different things. You kind of sit back and you’re actually kind of relying on this subject now do a really good job with a sort of not so great question that was asked a lot of times sales is the same way.

    If you’re attached to that outcome, you’re trying to lead the subject towards that outcome, versus just having an organic, authentic, genuine, sincere conversation and seeing where that takes you.

    Amanda Ripley:  Yeah,

    Katarina Jones:  I would also just add in, you know, Andrew, one of the reasons I was excited to have you on is because you have, you wear a couple different hats, right?

    You have the sales perspective, but you also are a manager, a people manager, and you also have the executive perspective. From more of a management perspective, it’s a very similar thing. Right?  If we’re trying to lead someone somewhere, the outcome, isn’t nearly as good as if approach people with genuine curiosity as well.

    Andrew Elliott: Well, and that’s where it becomes so cool, right? Is that like this art form, this  top of mind committed thing that you have to really work at. It’s not just in sales and it’s probably not just in journalism and it’s not just in people management, but it’s probably going to be kind of pervasive throughout every aspect of your life in a certain way. 

    Katarina Jones:  Amanda, I was interested in what you said earlier, and I had read this in one of your articles in Complicating The Narratives around you weren’t trained  about your process of how you ask questions necessarily you weren’t given feedback on that process.

    and that actually was really surprising to me. I didn’t realize that journalists aren’t trained in that process. and so I was interested to hear about that. Cause I think at some companies in sales, there is some training, but in some places there’s also not.

    Amanda Ripley:  Yeah, no. I mean, I think there are probably people who went to journalism school and got some training  in interviewing. Most people I’ve met for whom that is true, the training wasn’t necessarily that great. But most journalists didn’t go to journalism school, is part of, part of the answer. But I remember noticing this, really pausing, I never even questioned it. I mean, I get a lot of feedback on my work, right. Because editors, multiple editors edit the work. And then I hear from readers. So it’s not like I get zero feedback, but there are very few people listening to the process, right. To the interviews. No one actually other than myself.

    So I was doing a piece for the Atlantic about Starbucks had started this big program to help it’s its baristas finished college. And the big challenge with college in the United States is completing. Like finishing is the big challenge, not starting. And so the whole piece was about like, what do we know, what works? And Starbucks was also, to its credit, trying to figure out with Arizona State University, what works to help their employees finish.

    Cause most of them had some college credits. But hadn’t completed their degree. So, I was interviewing, some coaches. So one of the things that seems to be really, really helpful dollar per dollar is coaching, good coaching. So, you know, there are these people out there who coach, college students, particularly first generation students and check in with them by text or phone on a regular basis.

    They might have hundreds of people on their caseload, but this is what they do for a living. And I was interviewing one of them and she’d been at the company like 10 years and she said, yeah, you know, every phone call I have with a student is recorded and then scored on these different metrics.

    And then I get feedback and, I’ve learned a lot about questions to ask and questions not to ask and things to listen for and all these cool tips she had. And I’m like, All of a sudden, my brain switched from writing down what she was saying for the story to writing it down for myself, right?

    Because I was like, Oh my God, nobody, nobody listens to my interviews. You know? And here’s this woman is, five people are listening to her interviews and, and giving her feedback on all these different angles. And it was like, wow, that is  a huge failure of my profession, right? It is possible to help people get better at this, but like anything it’s hard to do in isolation.

    I mean, you can try, but you’re, you’re going to hit a ceiling. Right. So, just as a quick example, one of the things that she taught me was to listen for what she called gap words. So these are things that when she talked to the student, how’s it going? Like, how’s the business class going and dah, dah, dah.

    She listened for things they don’t say. Not just what they do. So, that was really interesting to think about. You know, if you ask someone about their last history test and they answer about, their last biology test, then that’s interesting. And then you, you need to go back. Right? Another thing they said is that they ask people the same question multiple times over the course of many weeks, which I never would have done because it felt like I’d be wasting the person’s time.

    Right. But what you find is that people say different things, particularly if it’s something emotionally loaded, or complicated, they say different things each time, and all of them may be true. But like, there’s not one answer to most questions. And so you have to ask it again and again, because people are not you know robots.

    And so, so there was a lot I learned just in that one encounter and I subsequently went on to interview more of those coaches for future stories, because, it just seemed like such a valuable exercise to learn these little tricks for how to listen better, essentially.

    Andrew Elliott:  Yeah. I’m now learning and writing things down that you’re talking about like gap words.

    That’s brilliant. And it makes total sense. Right? I don’t know, perhaps I’ve kind of thought about that at a certain point in time, but if I have, it was long time ago and I know what tomorrow’s sales team training is going to be focused on, is what customers are not telling us that we need to ask some better questions around. I also, I love the part about asking three times, well, in my world, I always tell my teams, you got to ask the same question three times to the same person.

    Or three times at three different people, if you really want to factor in on the truth, because the reality is whatever the answers are, they maybe true at that time, or maybe true to that person. But when you, when you’re in sales, you gotta get that full story, really understand the problem. And how likely are you not only to be able to solve it, but the customer be able to essentially fund, what that solution is going to involve. And so, there are harder questions that,  in the course of the sale have to be asked and asking one time and getting one answer, never works well.

    Not when you’re trying to build repeatability and some predictability into what it is that you’re doing. So I think that that was, That was really insightful that you talk about asking the same question multiple times.

    Amanda Ripley: Yeah. It reminds me of, one of my first large stories for Time Magazine, many years ago, was I followed, this gentleman, Gene Sanders, who had just come out of prison.  I met him, I was in the Bronx. Bill Clinton was looking for office space at the time, and there was a mob of reporters and we were all like, just like the TV guys were trampling, the print guys.

    And Gene happened to be there applying for benefits at the same office.  We were joking and he was helping me like block, you know, so I could get through and not get trampled. And, and we struck up a conversation. He told me he’d gotten out of prison that day. And so I ended up following him for a year off and on,  and sort of writing about what that was like.

    Cause there was an unprecedented number of people coming out of American prisons at the time and that re-entry, into their neighborhoods is very difficult and there are lots of reasons why, but Gene was a great and generous source. And then, we did this big story and you know, we got to know each other really well and he was incredible leap of trust for him.

     And then we went to a college to talk about the piece,  way after it came out and he stood up and gave a little speech. And I remember him saying things that he had never told me, like really good details, that I don’t know, I guess I had assumed I had the full story, which is ridiculous, right?

    Like why would I assume that there is a full story, first of all, but that like, just because we had a good rapport and relationship, he had told me everything or I had asked everything, right? And again, it gets to the point, I like this idea of ask it three times. Like I’d never actually given it a number, but that seems like a good number.

    And it’s like, you know, I had asked him what happened the day you got home. I’d asked him that. Right. And we’d gone point by point by point. And I had fact checked it with him at the end. So this is what happened at nine thirty, this is what happened at ten . But the thing he said to the audience of students was , he said he remembered watching his mother hide her purse. And how it just, you know, killed him.

    And it was such a, it’s such a powerful detail, but he hadn’t said that to me. You know, maybe he hadn’t trusted me enough at the time. Maybe I hadn’t asked the question, but that’s the kind of thing where, you know, so much of it comes down to ego. Like I had assumed I had the full story. You know? But there’s always more. There’s always more.

    Andrew Elliott:  Yeah. I think that’s  really worth underscore the assumptions part and the way that I remember, it was kind of framed for me and there was a lesson around it, that, you know, we just don’t know what we don’t know. And then, because that did make an impression on me. And there was a lesson that there was a whole thing that I went through to really have that come through.

    It’s now something that my team gets tired of hearing me say, because it’s so fundamental. We don’t know what we don’t know. And back to, you know, Katarina, you asked the question earlier, of like, training and sales, you know, we are fortunate, there is, there are some great training programs and I’ve been fortunate to have benefited from some of that also, but it is, it’s so hard not making any assumptions, acknowledging, setting the ego aside, that we don’t know what we don’t know. And the only way to do that is to acknowledge it first, and then start to figure out what questions we can ask to learn a few things and then learn a few things more from there. I do think everyone’s different. I think some people are probably more naturally adept at this than others for myself, I always have to work really hard.

    And, I have to prepare until the point comes where I just don’t anymore. And I think it’s kind of like, like anything, you know, people will see someone on stage, give a lecture, or a comedian go through their routine, or watch a band perform. And just seems so like flawless and natural and amazing.

    And what, you know, what we don’t realize is that for that person on stage, for every five minutes they’re up there, they spent an hour preparing for whatever that lecture is. And for the comedian, they’ve spent countless hours writing their routines, scripting these jokes practicing on peers, testing from, from one show to the next, until it’s literally a routine.

    That’s what it’s called. But they’re so good at it, and it’s been internalized so much that they’re just, it seems very, very natural.

    I’ve seen a band play, this is kind of embarrassing, I’ve seen a band play three times in the same week. And, it was extraordinary. It was the exact same performance every night. They told the exact same jokes.

    They riffed off each other in the same way. And if I’ve only seen it one time, I would have never known any of that. But you start to see, wow, there’s actually a lot of work that goes into all this. So, until you really internalize it, you have to put that work in and, you know, being a subject matter expert also helps.

    So that, that kind of can bring you to,  being in a position to get to aha moments as well.

    Katarina Jones:  So that’s where we’re going to leave Andrew and Amanda for now, we talked about the importance of listening and getting feedback on the questions you ask, and we discussed why it’s not helpful to make assumptions, or to get too attached to your agenda in a conversation. We’ve already covered a lot of ground.

    Things get even more interesting in part two, as Amanda and Andrew, get more into specifics. They share techniques with each other, and they start to recognize further parallels in their approaches. Thanks for listening. I’m Katarina Jones and this has been OtherWise Insights, part one.


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