AMY BERNSTEIN: You’re listening to Women at Work from Harvard Business Review. I’m Amy Bernstein.
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 BERNSTEIN: We do that by bringing together experts on those skills and audience members who want to get better at them.
AMY GALLO: OK, Amy B, I have been in many meetings with you over the years, and you are particularly good at asking purposeful questions.
AMY BERNSTEIN: What do you mean by that, Amy?
AMY GALLO: [Laughter]
AMY BERNSTEIN: Purposeful questions have a clear purpose. They’re intentional.
AMY GALLO: And they also are clear in that we know exactly what you’re getting at.
AMY BERNSTEIN: They have impact. They should elucidate a point, or they should move the conversation forward in some way.
AMY GALLO: And they invite openness rather than defensiveness.
AMY BERNSTEIN: 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.
AMY GALLO: Yeah. That actually ties really well into why our audience-member-slash-guest volunteered for this episode. Her name is Meagan. I’ll let her introduce herself.
MEAGAN: 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.
AMY GALLO: Meagan’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.
AMY BERNSTEIN: Aha.
MEAGAN: And that’s got 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?
AMY BERNSTEIN: Excellent questions.
AMY GALLO: 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.
AMY BERNSTEIN: 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 out 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.
AMY GALLO: Right.
AMY BERNSTEIN: And because of these stakes and tensions, our guest expert, Alison Wood Brooks, describes conversation as “one of the most complex and uncertain of all human tasks.”
ALISON WOOD BROOKS: 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.
AMY GALLO: Alison’s literally a scholar on the subject.
AMY BERNSTEIN: At Harvard Business School.
AMY GALLO: And she’s published a book called Talk: The Science of Conversation and the Art of Being Ourselves.
AMY BERNSTEIN: More from me after Amy G’s interview with Alison and Meagan.
AMY GALLO: Meagan, Alison, 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.
MEAGAN: Very excited for the conversation today.
ALISON WOOD BROOKS: 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.
MEAGAN: Yes.
AMY GALLO: So, Meagan, 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.
MEAGAN: Yes, there was actually… I was attending one of our department summit meetings we had a couple of years back, and I had the opportunity to ask our GM of our region as well as, 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. And 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? And 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.
AMY GALLO: 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.
MEAGAN: So, a recent scenario where 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? It is pretty obvious of what this is. And I realized that I wasn’t being as specific as I could have been.
AMY GALLO: 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.
ALISON WOOD BROOKS: 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 Meagan and Amy, or just Alison and Amy, or just Alison and Meagan. 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 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.
AMY GALLO: Is that true for you, Meagan? Do you feel more comfortable asking the questions one on one?
MEAGAN: 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.
ALISON WOOD BROOKS: 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, it’s sort of all tied together. But-
AMY GALLO: I would posit too, Alison, that’s also because our failures tend to be judged more harshly.
ALISON WOOD BROOKS: For sure, yes, it’s not wrong. These preferences have evolved from a place of reality—actually you are judged more harshly sometimes if you say something, and then we put pressure on ourselves if we’re not saying anything. So anyway, it just gets really complicated. So that’s the first thing when I was hearing about these stories, Meagan, 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 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 are 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.
AMY GALLO: I got to follow up on that, Alison, 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 want to wait. Meagan doesn’t want to wait until she gets the promotion to start asking the questions. So how do we psych ourselves into the courage we need regardless of our status?
ALISON WOOD BROOKS: Already we’ve talked about one thing, which is leverage intimate one-on-one conversation where you’re going to 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 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, will help you make better choices about the types of questions that you should be asking.
AMY GALLO: So, Meagan, 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 Alison about how to do that.
MEAGAN: Yeah. How do you keep credibility asking questions knowing that you’re not gonna 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?
ALISON WOOD BROOKS: 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 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, “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.
AMY GALLO: Would that work for the scenarios you’re thinking of, Meagan?
MEAGAN: It would, but how do I also though not trail off in those questions?
AMY GALLO: Yeah, and Alison, before you answer that question, can you, Meagan, give us a sense of, like, where are you asking these sorts of questions? Is this on one-on-ones, in meetings?
MEAGAN: I would say either in one-on-ones or in smaller groups. And actually, I lead an employee resource group, I’m leading the meetings, and I am 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 a decision about X, Y and Z?” 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 this 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.
AMY GALLO: Alison. Help us fix this.
ALISON WOOD BROOKS: Meagan, are you in this scenario… are you in a Zoom meeting or are you face to face?
MEAGAN: It’s always a virtual meeting.
ALISON WOOD BROOKS: Always virtual. So, I was going to say 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. Mm-hm. 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 cheering you on as you’re formulating this question to say, 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 just 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 getting to a place of acceptance of, I’m not going to get that verbal back-channel feedback that’s going to help me keep going. Just 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 of 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
