Women at Work - The Essentials: Asking Purposeful Questions

Episode Date: March 24, 2025

Purposeful questions do more than clarify details—they reveal how you think and demonstrate leadership potential. Amy Gallo talks with a program manager looking to strengthen her executive presence and question-asking skills. Harvard Business School professor Alison Wood Brooks joins them to offer research-backed guidance on eliciting useful responses, building credibility through questions, and adapting to different conversational settings.

Amy Burstein You're listening to Women at Work from Harvard Business Review. I'm Amy Burstein. Amy Gallo And I'm Amy Gallo. This is our Essentials series where we explore key career skills and make management advice practical and relatable. Amy Burstein We do that by bringing together experts on those skills and audience members who want to get better at them.

Amy Gallo Okay, Amy B, I have been in many meetings with you over the years, and you are particularly good at asking purposeful questions. What do you mean by that, Amy? Purposeful questions have a clear purpose. They're intentional. And they also are clear in that we know exactly what you're getting at. They have impact.

They should elucidate a point or they should move the conversation forward in some way. And they invite openness rather than defensiveness. I just want to note here that these are the same traits that you see in executive presence. They come from confidence and draw on your emotional intelligence, your ability to read the room. Yeah. That actually ties really well into why our audience member slash guest volunteered for this episode.

Her name is Megan. I'll let her introduce herself. I am a program manager in a biotech company, and I've been in a staff-level role for, oh gosh, it's probably been like four years. I ask questions that I'm super comfortable asking, and those can be questions that focus on the execution of a particular task or deliverable. Megan's looking to advance, maybe through a promotion, maybe by working in a different part of the business.

But the clear feedback she's gotten is that she needs to develop executive presence. And then a colleague recently pushed their team to think more strategically. And that's gotten me thinking, oh, well, how do I ask questions in a strategic way, as well as how do I ask questions in a way that helps me move forward in my career? Excellent questions. With no easy answers. Because her first concern, how do I ask questions in a strategic way, isn't only about taking the entire business into account, it's also about tone and delivery.

And that means negotiating tensions. You want to ask for the information you need without undermining your credibility. You want to get to the point but not leave that important context. You want to push for clarity without coming across as hostile. And in the moment, it's not always clear how to frame a question so that it lands the way you want it to. Right. And because of these stakes and tensions, our guest expert, Allison Wood Brooks, describes

conversation as one of the most complex and uncertain of all human tasks. We're all just sort of all the time trying to read ourselves, trying to read the person across from us, and read the room, the context all around us. And those are really high-level skills that we all need to continue to work on sort of forever. Allison's literally a scholar on the subject. At Harvard Business School. Yeah. And she's published a book called Talk, the Science of Conversation and the Art of Being Ourselves.

More from me after Amy G's interview with Allison and Megan. Megan, Allison, thank you both for joining me. And I have to note how meta this all feels because as I was prepping, I was thinking about the questions I wanted to ask the professor who studies questions and the person who wants to get better at questions and knowing you're both going to ask me questions. So this is going to be really fun. Very excited for the conversation today. Thank you so much for having us. I'm so excited to connect and I'm with you. It's very meta to talk about talking. So Megan, let's get a little more context of where you are skill wise in this and what your experience is like.

Tell us about a time you asked a question where you know you landed it. You got exactly the information or response or connection that you were looking for. Yes, there was actually, I was attending one of our department summit meetings we had a couple years back. And I had the opportunity to ask our GM of our region, as well as our, at the time, our chief commercial officer, some questions that I was very passionate about on a topic and I had about 10 seconds to jot down, what am I going to ask and be handed a microphone and be able to just ask it in a way that I really wanted to elicit a response. I felt really confident when I asked the question though, I will say I did blackout after I

asked it because it was a little nerve wracking, but I got really clear and detailed on the point. The response I got was actually people in the room applauded because the leaders, it took them a while to respond. They were like, do you want to take this one? Actually, it was such a good question that I got a lot of feedback after. I asked, I had actually my boss's boss come up to me and say, thank you for asking that question. It shows that our team is thinking critically

about this problem. But that was a time where I was very passionate about the topic. I was able to get the question down. Nervous though of asking it to these senior leaders, but I was able to get a good response afterwards. All right. So tell us about an opposite experience. Sometime where you either regretted not asking a question or you asked in a way that just sort of flopped.

Yeah. So a recent scenario where a chief of staff of our R&D came and gave a presentation and I asked the question, it was a little open-ended. And I realized that after the fact because I could tell from her facial expression and her tone that she's like, why are you asking me this? Like, it's pretty obvious of like what this is. And I realized that I wasn't being as specific as I could have been. Right. I'm curious, Alison, what you're hearing in those two contrasting examples.

I'm sure you're hearing lots of things that are reflected in your research. So many things, you guys. First, both of the examples you gave were in groups. It was in front of a lot of people. Group conversation is remarkably different, categorically different than one-on-one private conversation. We tend to think of conversation as the same task everywhere,

no matter how many people are there. But as soon as a third person pulls up a chair, even this conversation with the three of us is remarkably different than if it were just Megan and Amy, just Allison and Amy or just Allison and Megan. It means that one person there can sit and not say anything and still be part of the conversation. When you're one-on-one, that's not the case. You have to keep the sort of tennis ball alive going back and forth across the net. And as group size grows, the coordination challenges of keeping a conversation alive and smooth

grow exponentially. The risks of shame and judgment also grow exponentially. A lot of people who are not high status in their organizations feel a lot more comfortable and more power when they are in smaller, one-on-one interactions. And so the more you can leverage that, the better things are going to go. If you can pull that boss aside after the big group meeting and say, oh, actually, I meant to ask that

question this way. Would you mind like chatting about that a little bit? That feels so much more approachable and that conversation might be a lot more productive than trying to ask even the same question in front of the group. Is that true for you, Megan? Do you feel more comfortable asking the questions one-on-one? Oh, definitely. In those higher-stakes situations where it's a larger group, I have to either prepare or if it's off the cuff,

shame is definitely something that comes up. It's waiting right there like a specter on the doorstep. You're not alone. So this is a feeling that most people feel, introverts for sure. And even in some of our research, we have found that women have a very strong preference for smaller intimate conversation compared to large groups,

likely because women tend to occupy positions of lower status a lot of the time. So that's sort of all tied together. And I would posit too, Alison, that's also because our failures tend to be judged more harshly, so. For sure, oh yes, it's not wrong. These preferences evolve from a place of reality

of like, actually you are judged more harshly sometimes if you say something, and then we put pressure on ourselves if we're not saying things. So anyway, it just gets really complicated. So that's the first thing when I was hearing about these stories, Megan, is the distinction between intimate and groups. What can be very empowering is to think,

well, how can I leverage the comfort I feel in one-on-one conversation? Often you do have power over structuring the size of your conversations. Who can you talk to before a big group meeting? Who can you talk to after? And how can you leverage that a little bit more? And then one other thing that I heard in your, the way you describe these stories is you tend to ask questions that feel comfortable. And then when you described your success question asking,

you described it as passionate. It was a question I was passionate about. And in that moment I was like, oh, I love it so much. Not only do you sound like you were dying to ask that question, but it took some courage to do it. And whether it's in a group, in a high-stakes situation, or one-on-one, every little micro decision we make when we shift to a new topic or ask a new question, it really is like a risk.

It takes courage to say, am I going to go here? And it sounds like sometimes when you feel like you're not finding that courage and not able to take those risks, that's when your questions are coming out as a little bit mundane or less articulate, or you're not really asking the question that you are actually dying to ask. I got to follow up on that, Allison, because if the research says we tend to be more fearful or hesitate to ask questions when we're lower status, obviously we don't wanna wait.

Meghan doesn't wanna wait till she gets the promotion to start asking the questions. So how do we psych ourselves into the courage we need, regardless of our status? Yeah, already we've talked about one thing, which is leverage intimate one-on-one conversation where you're gonna feel more brave anyway, and where it feels safer for the other person to answer, that you're not putting them on the spot and giving them the risk of shame. The other thing I think that can feel

really empowering is good conversationalists align their choices with the goals of the conversation. And so a little bit of reflection ahead of time of what are my goals in this interaction and what do I think other people's goals are, particularly at work. If you even think for like 30 seconds, oh, the goal of this meeting is we need to choose someone to hire. So my questions should be helping guide the group towards making a decision to hire someone. Or our goal here is to generate as many ideas about this new product as possible. So just keeping in mind, what are we doing here?

What are our needs and goals? We'll help you make better choices about the types of questions that you should be asking. So Megan, one of the things that was on your mind, you told us, was asking questions that for lack of a more nuanced way to say this, that didn't make you look stupid. And so I'm curious if you have any questions for Allison about how to do that. Yeah. How do you keep credibility? Asking questions knowing that you're not going to come across as knowledgeable about a particular subject, but showing that you are curious and want

to learn more and not necessarily distracting from the conversation. You can literally just say, can you say more? Can you keep going? Can we hear more about this? And I think often we put pressure on ourselves to come up with this like well-phrased question when in fact what you need from another person is for them to just say a little bit more because you're not actually understanding what they're saying. And can you say more is a wonderful question. That's enough.

That is a show of your competence that you see that there's value in what they're saying. In a way, it's the ultimate open-ended question. So when we studied open-ended questions, there are lots of ways to phrase open-ended questions. One is by starting it with a what, like, tell me what else is on your mind, or what did you do this morning? What were you thinking about when you prepared for this meeting?

That's a beautiful open-ended question. And you could frame all of those same questions by starting with why. Why questions are still technically open-ended, but they're more accusatory. It sort of pulls back on the lovely relational motives and things that we need in conversation to have it feel safe and productive.

So leaning more towards the what is on your mind, can you tell me more, tell me your perspective, those questions are really productive and it doesn't take much from you to formulate them. You just need to say, like, what did you mean? What were you thinking about? What are you feeling right now? And sort of put the ball back in their court.

Would that work for the scenarios you're thinking of, Megan? It would, but how do I also, though, like, not trail off in those questions? And actually, before you answer that, Aslan, can you, Megan, just give us a sense of, like not trail off in those questions. And actually, before you answer that, as in, can you Megan, just give us a sense of like, where are you asking these sorts of questions? Is this in one-on-ones and meetings? I would say either in one-on-ones or in smaller groups. Um, and actually I lead a employee resource group. And actually, I lead an employee resource group. I'm leading the meetings and I'm discovering as I'm asking questions to the group. For example, are there any other points of feedback that we want to capture before we

make the decision about X, Y, and Z? And I'll trail off at the end. And so it'll be like, what do you think about this? And then it's like, I know they know what I'm talking about, but it's like, I get stuck. It's like, how do I really complete the sentence or ask this question in a way that's going to sound intelligent, but then halfway through it's like, oh, this is just tapering off. And a lot of the times they ask me to repeat it. They ask, is this what you're asking? And I think where it's coming from is the fact that I don't feel confident when I'm

asking the question, but I know I need to keep the conversation going. Oh, Alison, Help us fix this. Megan, are you in this scenario, are you in like a Zoom meeting or are you face to face? It's always a virtual meeting. Yeah. Always virtual. Okay. So I was going to say, you know, any group conversation can be very demoralizing, but

especially virtual meetings where people are muted and you're not even getting the sort of back channel feedback, which is people going, yeah, uh-huh, uh-huh. In natural conversation face-to-face, that's like a version of cheerleading where your partners and the people in the group are like cheering you on as you're formulating this question to say like, yes, keep going. We also want to ask this question. In virtual meetings, you can't get that. It's not surprising to me that you're sort of trailing off midway because you need that cheerleading. You need that sort of co-narration in order to get the sense of, am I heading in a good direction or not? And the silent void that you get in a virtual meeting

is sort of soul crushing in that way. And so by the time you get to the end of your question, you have no idea whether you're asking it clearly or asking the right question. So I think just knowing that and sort of getting to a place of acceptance of like, okay, I'm not going to get that verbal back channel feedback that's going to help me keep going, just kind of get to a place where you're more comfortable with that. And it is actually soul crushing and it's not you, it's the modality that you're communicating

on. In my course, when I teach students about conversation, I have them record themselves and listen back. And without fail, one of the first things everyone notices is how inarticulate they are and how many filler words they have, and they're totally mortified. And so they'll say, oh, I'm going to work so hard this semester to stop saying um and uh and trailing off. And then we talk about like, no, don't do that.

That is how natural dialogue works. You cannot plan out whole sentences before you say them. So you are coming up with what you're saying as you're saying it. Trailing off is a sign of uncertainty. It gives a signal to the people around you that you're formulating a bigger, more articulate idea. And so I'm not sure that the problem here is with you trailing off. I think what you're formulating a bigger, more articulate idea. And so I'm not sure that the problem here

is with you trailing off. I think what you're like hungry for is you want fully formed thoughts that are really incisive. And so it's not about the ums and uhs and the trailing off. It's sort of like, how can I frame my question in a way that really gets to the heart of what we're trying to do here? And for that, there are different ways

that you can think about framing your question. You can ask people thinking questions versus feeling questions. What are you thinking about this? How are you feeling about it? You can ask people positive versus negative. What would be the positive outcome of us doing this? What would be the negative outcome of us doing this?

You can ask, let's consider this from a different perspective. So for whom, for whom would this decision be good? Which stakeholder in this situation? You can ask when questions. When was this a good thing? I know this was a good thing in the past and we're feeling a little uncertain about it now.

We're now gonna, what's gonna happen with us in the future? So past, present, future questions can be really incisive. And so for that, you could sort of practice getting good at it on the fly, or you can think about brainstorming those types of questions before a meeting begins. Like, what do we need to talk about? Do we need to talk about the past, the present, the future? Which stakeholders do we care about? Do we need to talk about what we're thinking or what we're feeling?

Or both. A little bit of brainstorming ahead of time can be quite helpful. Are those helpful, Manny? It actually is. And I think one thing that you mentioned, Alison, that's really resonating with me is the human element of asking a question. It's okay to say the ums and to trail off. And I think that's kind of where I've been a little self-conscious is how to sound as

crisp as say another coworker I have that I look up to. She's really good at asking questions and also just on the fly of being very articulate when the conversation is dynamic. And every conversation is a combination of forethought and flexibility in the moment We as humans have a tendency to see amazing talkers and feel like there's a sort of myth of naturalness like oh They're so amazing. This is so easy for them You have no idea how much work that that person did before the meeting how hard they are trying in the meeting How much follow-up they're doing afterwards? So when things look easy and skilled for other people,

you just never know. I'm sure that it's not just coming to her spontaneously in the moment. And she's probably spent her whole lifetime sort of practicing that skill too. And then the final thing that I will say is, when you start to look at like hundreds of thousands of transcripts of real conversations,

you realize conversations are a train wreck. And so we put all this, we put all, we interrupt each other constantly, we fade away in the middle, we have half finished ideas, we get excited about this, and then we move on to something else and we forget to talk about the thing we needed to talk about. We all put so much pressure on ourselves for it to feel perfect and polished and productive. But the bottom line is that it's a very complicated coordination game that is never going to be perfect. So finding a bit of grace for yourself and for other people is a really great place to start.

When you said you have a colleague who you admire in terms of how crisp she is in asking questions, I want to reach out and hug you because try being Amy B's co-host on this podcast. She can ask, I will ask the question in four messy sentences that trust me gets the point across and then she'll just ask it in four words with some beautiful vocab word I hadn't heard in five years. But yet I will tell you, I could allow it to hurt my confidence, but I really see it as a style thing. It's just a different style.

I'm sure editing me is really hard for our producer because I do ask those questions that go on and on sometimes, but I think I also bring some richness to it or some emotion or some connection with the guest. So yes, you want to, Amanda's telling me in the chat that I do, thank you. Yes, maybe emulating and even watching that colleague and studying what they do. And yet I also don't want you to try to do something that's not you.

Because part of what it sounds like is that the anxiety in that moment when you start trailing off is the problem, not the trailing off necessarily, right? You're like, oh, did I sound like I didn't know what I was doing? Am I not being leaderly enough? Am I leaving everyone confused? But maybe you just let it trail off and see what responses come back. And if people need clarity, then you can give clarity. I really like that. I think it's so helpful to hear that it's a different style. And I definitely have a trailing wandering style.

It's very warm, actually. It's very, you really pull people in. You can tell you're very thoughtful and that you really care. So you might be the perfect person to be on a team where everybody's moving too fast and not listening well and their questions are too quick and clipped. They need someone like you to sort of break the pace and slow it down and say, okay, well, let's think about this in another way. Thinking about group composition in that way could be really empowering, I hope.

Oh yeah. I feel really good about the feedback around that because I don't think I hear it enough of your style of communicating works well within this group dynamic or at least appreciating where I'm coming from. Sometimes when I've asked for feedback and said, please give me feedback on this particular thing, sometimes the feedback is just, oh, you did great. I really want to improve or find specific examples of, you did great here and this is why. Recent research suggests that it's easier for people to give more constructive ideas to you

if you ask for their advice rather than feedback. So backward looking feedback feels harsh because it's already happened and it's sort of like saying you did a bad job. But if you say, if we're going to do that meeting again, what advice would you give to me about how to do this differently? Then it feels like you're brainstorming together and preparing for something that has yet to come. And so it feels less harsh to say, oh, yeah, I love how you put together. Your slide design is gorgeous.

I love how you explain this idea. Next time I wonder if you could be a little more piffy when you're explaining X, Y, and Z. That's also gonna be easier to hear than them saying, hey, you were super long-winded when you talked about this in your presentation. So just a slight reframe of forward-looking advice, seeking that rather than backward-looking feedback. We do have an essentials episode similar to this one

called Getting the feedback you need, which we cover some of that. Thinking about getting feedback about the questions might be helpful to listen, give another listen to that one. Yeah, definitely. I love the reframing. So let's talk about the questions where you need to dig into what's really going on in this situation because I know this was another area, Megan, that you were trying to work on, asking questions when the situation isn't clear or something's held up. Is there a scenario you're thinking of specifically, Megan, for this kind of question? Yeah, it's going back to maybe a one-on-one conversation that I have with a senior leader. And I know that they're a couple steps above and I'm really

trying to ask them the strategy questions and try to uncover why we are making particular decisions and understanding how the strategy is developed. And I want to be able to ask it in a way that also allows them to provide the reasons why things are happening and not come across as confrontational. It sounds like you're hungry for more information exchange. I think often we have an instinct to say, well, what's the right question to ask? And as a scholar of conversation, I feel like putting too much pressure on yourself to ask the right question may not be the right way to think about it.

Instead, what we see when we study transcripts is that it's more like the pattern of questioning that's good as the conversation unfolds, that is good at diving deeper and deeper and getting more information exchange rolling in the conversation. So instead of focusing on sort of like that first question or like what's the right way to formulate this question,

imagine if you just pushed yourself to ask more follow-up questions. So no matter what information they start with, you just keep pushing and saying like, well, what were you thinking about when you made that decision? Or if you went to 30,000 feet, what conceptually are you thinking about here?

And sort of don't stop asking until you get to a place where you feel like they're giving you that sort of valuable treasure that you're looking for. It almost has nothing to do with the initial question and more to do with, I'm going to listen as this unfolds and I'm going to keep asking until we get to a place where I feel like I'm getting the information that I need. And what's so funny is that sounds so simple, but most people forget to keep asking follow-up questions. As soon as somebody like you ask one question, they give an answer and then you're like,

oh, I guess we got to move on. No, you should keep going. In my class, we do an exercise called never-ending follow-ups where you're required to ask a follow-up question every time you speak, which sounds very extreme in theory, but in practice it's super fun. You'll very quickly get past small talk. You'll get very deep on a topic. Good conversationalists are good at changing topics frequently, but also getting really deep on them quickly, often through asking lots of follow-up questions. Yeah, I can count on one hand

the time to number of times I've been like, I did not like that person because they asked difficult questions. But dozens and dozens of times I've said, that person didn't ask me a single question. This is so important, Amy, that a very important point that I hope will be helpful to you, Megan, there really is no such thing as a sensitive question,

but there is very much sensitive contexts. A lot of people have fears that by asking something too intrusive or too sensitive, that people are going to get mad or hurt or sort of these high arousal negative emotions, but it's actually a lot less common than the quieter killer of conversation, which is boredom and disinterest. If we're too scared to ask interesting, pointed, sensitive things, then the risk is that the whole conversation is completely forgettable and mundane and feels meaningless. And that's actually a more common occurrence in conversation than the anger, hostile feelings. Okay, Megan, you had a question about asking questions

that demonstrate your leadership qualities that you're ready to take on more responsibility. Do you wanna ask Alison about that? Yes, I really have been thinking about how do I move away from always kind of the comfortable questions? Or even it's like, how do I move away from always kind of the comfortable questions or even it's like, how do I ask this to show that I'm thinking strategically or thinking like, you know, I want to move, move up or make a big career leap. And I want it to be known

to other people when I'm having these conversations, like, I'm interested in this. And so how do, I guess, how to move away from just the execution type questions and moving into a more leadership focused mindset when asking questions. Wow, I love this. I love hearing you sort of step into your power even saying this question out loud. It's really wonderful. A very simple idea is trying to say your goals out loud. And that's probably not necessarily about you, but maybe about the needs of everyone

who's involved in the conversation. It seems to me like you need this, or I'm going to say something because I care so much about you succeeding, or I think everybody's feeling a little anxious about this, so I'm gonna say something because I care so much about you succeeding or I think everybody's feeling a little anxious about this so I'm gonna say this. Literally saying like what is your strategic thinking? What is your perception of people's goals? What are we aiming for as a group? Literally saying that out loud more explicitly can be quite helpful because it allows people then to agree,

yes, that is our goal, yes, that is how we're feeling, or to say, oh, actually, no, I'm not feeling anxious about that, but I am feeling scared about this other thing, or I am excited about this other thing. So linguists call this grounding. It's like sort of always revising and weeding your shared reality,

your shared understanding of what's going on. Good strategic thinkers are good at providing a very clear platform of like, what are our goals and what are we doing here? That allows other people to pile on and say yes, or to disagree with it and sort of repair that understanding. Well, and I have a slightly different take on the sort of how I prove my capability of moving forward, which is to really ask an analytical question, something along the lines of, okay, I understand we're not going to move this

initiative forward. What would have to be true in the future for us to do that? And shows that I'm invested in the future of this team or this initiative or this organization. That doesn't conflict with what you're saying, Alison, but I think it's another tactic that I have found works for me. The more you can figure out what your colleagues want and need and what the organization wants and needs, and you show effort in pursuing those things, it just signals indirectly that I'm part of this

and I am aligned with the mission and I wanna be helpful at it because I see a future here, because I want to succeed in this place. Thank you both. I really enjoyed this and I'm taking away so much. Amy, you're such a fabulous facilitator of a three-person group. And Megan, I just wanna like gobble you up.

You're so wonderful. I really appreciate this opportunity and being able to speak with both of you. It's been really rewarding and I feel more confident in my style now that I've had this conversation. So, thank you. I really appreciate the confidence boost. Amy B, you're back.

I am back and I'm here with someone who helps us ask purposeful questions every episode of this show. That's right, our producer, Amanda Kersey. Hello. Yes, I decided to come out from behind the scenes and insert myself here. We're glad you did. You're always here with us. I'm usually just four feet back at that computer, but I have lots of thoughts about asking purposeful

questions. But I wanted to pick up on something that Amy G mentioned to Megan and Allison about you two having different styles and how she doesn't want to be self-conscious about that. It's just a style thing. That's all okay. But as you know, because I think I shared it with you a few months ago when I was getting really into my chat GBT assistant, the Women at Work AI, that I asked it to describe your interviewing styles just so I could like see that as a knowledge file. Based on our transcripts.

Based on, I uploaded all the transcripts from the show, every single one of them. And what came out was unbelievable and very kind. Okay. what came out was unbelievable and very kind. Okay, so the AI assistant said, Amy Gallo frequently seeks out advice that listeners can apply to their own lives. Her questions often dig into the how and why of specific behaviors or strategies, aiming to extract clear, actionable insights.

She's particularly skilled at asking follow-up questions to get more detailed, tangible answers from experts. I hear it's so kind. It is kind, but it's so funny. It's accurate. Well, and I feel, I have to say, I feel a little like Megan right now, where I'm like, okay, it's just my style. Because I hear that and I'm like, yeah, I ramble.

I get it, I ramble. Has anyone ever said you ramble or is that just your self-assessment? It's just my self-assessment. I sometimes, I feel a little like Megan sometimes where I'm halfway through the question. I'm like, where am I going with this? What am I saying? And I think in contrast to you, Amy B, and I can't wait for you to read what Amy B's style is, but in contrast to you, sometimes it's like these five words that just get to the point so quickly. And I understand that's like, you've been an editor for many, many years, you've been trained to do that,

but it's just such a skill. And if I were more insecure, I think I would really shrivel in comparison to you. But I loved Alison's take on this and reassurance to Megan of like, there's just a different style. And it doesn't make the question less purposeful. And even if your questions are a little windy,

our AI is still saying, like you extract clear actionable insights. So even if you're windy, you're getting the goods ultimately. And they're always entertaining and engaging. Thank you. We're on the journey with you. Thank you. We're on the journey with you, Amy. Thank you.

We are. Thank you. Okay, let me flip this page and Amy Bernstein's style. Okay. Amy Bernstein is not afraid to challenge ideas or ask harder thought-provoking questions. Her questions often encourage guests to think more critically or consider alternate perspectives. This can result in a deeper, more nuanced exploration of the topic. That resonates so much for me.

I can notice no mention of warmth. Well, below is professional yet personal. Your warmth comes through in your curiosity. So Amy B, we haven't talked on the show yet. Y'all haven't talked about the fact that you got a promotion recently. You are now HBR's editor in chief. Thinking about how Megan wants to impress executives, the senior leader, she wants to get up there in her own industry one day. What are the types of questions that you're listening for as an executive when you're in the room

with people who are more junior, who are maybe you pick up on the fact that they're trying to impress you or they just happen to impress you. What are you listening for? Well, let me tell you what I pick up on. I pick up on genuine curiosity, questions that bespeak a person's understanding of the idea and commitment to embracing it by understanding it better. I really do appreciate questions that smoke test an idea, unless they're smarty pants questions. The questions I like are the ones that open my mind

to new thinking, make me consider things I ought to have considered but may have missed. Mm-hmm. And what you're saying that you look for is not someone who just pokes holes, but someone who in the interest of the larger pursuit, the goal we're trying to, may poke holes or may ask hard questions. You know, one of the questions I like to ask when I'm trying to understand a decision someone in a senior leadership position has made more clearly is, what

other options did you consider and why did we go with this one? That is such a great, great question. And when you have asked me that, you make me stop and think. When you ask a question like that, Amy, like asking someone to explain their reasoning behind that decision, like what alternatives they consider, that can be a sensitive question. That could put somebody on the defense.

So how do you work up to that kind of question? Like, what are you doing before you ask that? No, she doesn't. Yeah, you don't go right into that. I mean, I think that's where tone comes in. I might say, help me understand this further. Or I might even set it up with, I'm thinking about how I'm going to explain this to stakeholder, customer, client, whatever. Help me understand what other options did we get. I mean, because the tone of that question could be very challenging. You mentioned sensitive questions, Amanda, and we didn't talk too much in the conversation with Allison and Megan, but Allison, in her book, she is pretty bold about saying there

are no sensitive questions. There's only sensitive context. Context, yeah. Exactly. I do have one thing to say about that. When people are asking the really sort of sensitive questions, I think that is the moment to be really straightforward. Yes.

In the response or in the question? Well, always in the response. Yeah. But in the question as well. Mm-hmm. Because I've been on the receiving end of the sensitive question. And sometimes I struggle to understand the question itself.

What are you really asking me? And I'll ask him. You know. Say more. Or I'll say, I don't quite understand what you're trying to find out, which isn't pushing back. It's a request for clarification. Yeah.

I have found that leading with the reason you're asking Yes. will make clear your motive and also offer clarity. Mm-hmm. Because when you're nervous, maybe your question is coming out not so clear. So if you start by saying, you know, I'm really trying to understand this,

or our teammates and I, we've had this concern I'm really trying to understand this, or our teammates and I, we've had this concern and we're trying to understand that, can show the benevolence with which you're coming to the conversation. Stating the intention of, I need this clarity, I need the answer to this question in order to do my job or to help guide my team or whatever it is, gives them the context in which you're going to use the answer to. So I think it takes down the heat. I think one of the sort of preambles to a question also could be, this is something

I take from, you know, difficult conversations, researches, stating a shared goal. You know, I know we're both trying to do X. We're trying to work through this incredibly uncertain time for our organization. So, you're putting you and the other person in a collaborative mindset as opposed to a combative mindset. I think that's right. And when you're talking about strategy, a new product,

something like that, chances are, as the asker of the question, you want to be able to sell this idea further out, right? And you can say that, I just, I wanna make sure I understand this so I can do a better job persuading others about it. You know? Who wouldn't?

Who wouldn't wanna help, right? Yes. Okay, no further questions. Thanks for having me. Oh yeah, thank you, Amanda. Can you come over to the table more times? I might just roll on over here and there. Roll the three feet over.

I'll roll the three feet over. for watching. Network's editorial and production team is Amanda Kersey, Maureen Hoke, Tina Toby Mack, Hannah Bates, Rob Eckhart, and Ian Fox. Get in touch with us by emailing womenatworkathbr.org.