Introverts Can Be Leaders Too

HANNAH BATES: Welcome to HBR on Leadership, case studies and conversations with the world’s top business and management experts, hand-selected to help you unlock the best in those around you. We all have preconceived notions about which personality types are associated with good leadership — like confidence or emotional intelligence. But what about shyness? If you’re more reserved but truly competent — can you become a leader? Today we bring you a conversation about how being shy and being a leader aren’t always in conflict — with the help of Alice Boyes. She’s an author and former clinical psychologist. Boyes explains that there are professional advantages of some personality traits related to shyness — like sensitivity and thoughtfulness. And she shares strategies to work through some aspects of shyness that may hold you back as a leader. This episode originally aired on Women at Work in October 2020. Here it is.

AMY BERNSTEIN: Recently we got an email from a listener named Laura who talked to us about a problem that really resonated with me. She suffers from what I would describe as painful shyness. She is loaded with ideas. She is highly competent, but when the spotlight turns to her, she turns boiled lobster red. That’s how she describes it. And the part that really got me was when she started to describe how this kind of extreme sensitivity and her introversion is starting to get in the way of her career advancement. I mean it has become a real barrier. You can read her frustration in her email.

AMY GALLO: Yeah, we all read that email. We thought it would make such a good episode, but of course we wanted Laura to talk with us and wondered would she actually do it. So, our producer, Amanda got her on a video call to pitch the idea.

LAURA: Hi.

AMANDA KERSEY: Hi. We loved your email. That was so thoughtful and gave us so much to think about.

LAURA: It was so great to hear back from you guys.

AMANDA KERSEY: Oh yeah. So, when we were trying to figure out what we would do with this episode, what this episode could be, what we would want to talk about, try to figure out what advice we might give, who an expert might be, we thought that what would really bring these questions alive and humanize the subject is obviously for you to come on the show.

LAURA: OK. [LAUGHTER] Yeah, I’m totally, I’m totally willing to do that. As a shy person, the performance-related prospect of being on the show is a little nerve wracking and just like talking about something that’s like painful and personal. And I would want to do it for that very reason. I want to create a space where we can talk about it and not be afraid to talk about it and not be ashamed to talk about it, and to say like I’m in my 40s and I’m still grappling with this. Like I would very much love the opportunity to do that.

EMILY CAULFIELD: And I was so glad that Laura agreed to come on the show. I know how anxiety-inducing it can feel to put ourselves in such visible positions. I felt like I connected with what she revealed to us in her letter so much. I volunteered to interview her for what was one of my very first interviews. Something that I was really nervous to do, but her vulnerability made me feel comfortable to do that. So, Laura, thank you so much for coming on the show. I am so happy to have you here.

LAURA: Thank you so much. It’s such a pleasure to be here.

EMILY CAULFIELD: Yeah. I’m also very shy, so I’m really happy that you wrote into us. So, let me ask you, how does your shyness tend to manifest itself? In what scenarios? How are you feeling?

LAURA: Well it’s definitely changed over time. It’s still something that I grapple with a lot, but it’s like way better than it was when I was a kid, or when I was a teenager. When I just found it really difficult to maintain eye contact with people, to talk to people I didn’t know, certainly anything that was public speaking or having to present myself in front of people, especially people who felt important or in a position to judge me. I’ve gotten a little bit better at that over time, just I think by experience and sort of forcing myself to endure situations where I just have to do it. But it still doesn’t feel comfortable. And, for me it’s a combination of being a naturally introverted person, so it takes me more time to warm up to people, to warm up to a room, to warm up to a team. And then it’s compounded by the shyness which to me is more of a fear of criticism, a fear of judgment, a fear of exposure, and that’s just like been with me as long as I can remember. And, the most unpleasant part about that is that I’m a blusher. So, if I’m in a situation where I feel uncomfortable or I feel embarrassed or I feel like I’m being judged, I turn bright red. And that’s awful because it’s so public. You can in some ways disguise or manage certain aspects of shyness, but that one, you can’t. It is just so apparent to everyone. And in my teens and 20s, I think there was some aspect of that that was like kind of cute, or kind of sweet, or people found it a little bit endearing, but when you’re a professional in your 40s, absolutely not.

EMILY CAULFDIELD: And is it still happening now like during the pandemic and not being in the office?

LAURA: That’s an interesting question Emily. I am actually finding this way of working to be a little bit of a reprieve. I do better on the phone because I’m not seen and I’m not watching other people and monitoring their reactions and thinking, OK, what did they think about what I just said. I can’t see that on their faces. So, I’m happier in a situation where my communications are written or they’re Zoom calls where we’re not using video. I feel like that levels the playing field a lot. I’m also a master of the chat function. So whereas my shyness might hold me back from saying something, or interrupting, or jumping in with my ideas, putting something in a chat box allows me to get my ideas out there, but I can craft the way it’s presented and people can absorb it when they see it. And I’m not going to get talked over.

EMILY CAULFIELD: Definitely. So, I guess during this time it’s the good coping mechanism is one that you didn’t necessarily choose, which is you are able to write things out more often, or speak over the phone, or not be directly in person. In other situations, have you found that other coping mechanism have been helpful for sort of getting past your shyness?

LAURA: Yeah, a few things. The first is that I discovered in nursing school that beta blockers really help. Actually, like medication. So, that was a game changer because if I knew that I was going to be doing something where I was likely to blush, or was going to get really nervous, and I was super anxious about it going in, and of course being super anxious increases the likelihood that all those things are going to happen, I could take a beta blocker. I could feel confident that I wasn’t going to have that same physiological reaction. I wasn’t going to blush, I wasn’t going to sweat. I was less likely to trip over my words. That would help me to go into a situation feeling more confident. The problem is that it doesn’t always work. The other problem is that you can’t always predict when you’re going to be put on the spot, or when you’re going to be challenged, or anyone of those situations that might trigger a sort of shy reaction. Other things are strategically avoiding certain circumstances where I didn’t feel like it was going to have negative consequences for me personally or professionally. And then the last one is that I just really over prepare. So, when I know that I’m going to need to defend myself, or take a position on something, or have a tough conversation with somebody, or be very public or have to give a presentation in front of a particular stressful group of people, I am thinking through every eventuality. I am writing everything down. I am practicing it over and over and over again, so that I can be on autopilot a little bit when I go into it and so that I feel, I feel much more in control of the situation. But that’s really time consuming, and it’s pretty exhausting ,and you also can’t also anticipate every question or every direction that a conversation is going to take.

EMILY CAULFIELD: Right. So, did something at work happen that caused you to reassess where you are with leadership and where you are in the process of trying to deal with your shyness?

LAURA: Yes. There was a situation that kind of became a real soul-searching moment for me and sort of sent me down a pathway of really wanting to interrogate this whole thing and make some decisions around it. It was a situation where I really felt like I was watching someone in a leadership position, the kind of position that I am headed for and I didn’t know if I could do it, and I didn’t know if I wanted to do it – specifically because of my wiring. And like putting myself in her shoes, I could have seen myself completely freezing, completely a deer in the headlights, freaking out, retreating, withdrawing, and not rising to the occasion. It was a really powerful moment because it sort of brought everything together. This is something I’ve been dealing with forever. It’s sort of something that I found ways to manage on a day to day basis, but it was the first time that I realized, wow, this could really be such a significant handicap that it could totally keep me from being able to grow any further than where I am right now. It came down to the question of: Am I just not a good fit for leadership because I’m introverted and shy and sensitive, and like ultimately those are just not compatible with what’s required of a leadership role? Or, is it that it’s uncomfortable for me? I’m going to need to really push myself way outside of my comfort zone, and am I willing to do that?

EMILY CAULFIELD: So, Laura, what would you like for us explore in the rest of the episode? What do you think would be helpful for you to hear, for other women like you to hear as we finish this episode up?

LAURA: So, if we’re working with the assumption that I’m going to take the leap and try to position myself for more of a leadership role, that I’m going to like tread into some uncomfortable waters and try to find a way to do that, I wanted to know others who have done this before me and who are successfully doing it, who are leaders, who are shy people. What habits do they have? What tips and tricks do they use? What advice would they give for being able to do that successfully?

EMILY CAULFIELD: I want to learn the same thing so I’m looking forward to it. Laura, thank you so much for coming on the show. I’m so happy you could be here. Thank you for writing into us. This is awesome.

LAURA: Oh, it’s been such a, such a joy. Thank you so much Emily.

EMILY CAULFIELD: So, that’s how one woman has been grappling with shyness at work. Later in the show Amy B. and I will tell you how we’ve grappled with it ourselves. But first we’ll hear from an expert I interviewed who broadened and deepened my thinking around what shyness is. Alice Boyes used to be a clinical psychologist and researcher. Now she’s an author writing about psychology. Her two books are The Healthy Mind Toolkit and The Anxiety Toolkit. So, Alice, thank you so much for joining us today. I’m really looking forward to talking with you.

ALICE BOYES: Nice to be here.

EMILY CAULFIELD: Yes, so you heard Laura, one of our listeners who wrote into us, talking about her experience and her struggle with shyness. Can you just speak more broadly about what shyness is and how it shows up, particularly in a work setting?

ALICE BOYES: Yes, so shyness is, it tends to be something that has been a characteristic of people since childhood. So, it’s a manifestation of social anxiety generally. That as a kind of trite that people have, that shy children grow up into, to shy adults rather than a type of social anxiety that’s brought on by a trauma or by a later experience. There are some other things that can look like shyness that aren’t necessarily related to social anxiety like somebody who’s got some mild autistic spectrum stuff that can show up kind of looking like shyness, like looking like some social awkwardness. Introversion and high sensitivity can also end up looking like shyness. So, there’s a lot of overlapping concepts there, and some people who identify as shy don’t necessarily identify as socially anxious. Whereas, for some people with social anxiety and shyness, they use them as synonyms.

EMILY CAULFIELD: Mm hm. Yeah, so I was interested that Laura kind of came to understand her shyness as being this innate part of her temperament that she was always going to have. I expressed to her that I also feel pretty shy at times, and in my mind I’m kind of like, maybe I’m going to grow out of this one day. But you are of the belief that it might be part of our temperament that we have to sort of grapple with and deal with over the course of our lives, our working lives.

ALICE BOYES: Yeah, I wouldn’t, that’s not how I think about the fundamental dimensions of people. So, I would sort of break it down a little bit into the words that we use more to talk about temperament in the research literature. So, things that, the extent to which someone is bold or cautious. People vary in terms of how much they care about what other people think of them. So, some people think very little about what other people think of them, some people think a lot, and there are a bunch of people in the middle. And most people care something and that they’re highly adaptive then because it’s a survival thing. So, in an evolutionary sense they’re excluded from a tribe would be very dangerous, so it was a very good to have that skill of caring what other people think. We also have some people who are just more thoughtful than others. So, some people do a lot of reflecting and they just do a lot of thinking. Like if they’re going for a walk, or they’re in the shower, it’s called need for cognition. So, professionally I probably wouldn’t, call it shyness because there’s more specific things going on there, but I understand that shyness is the colloquial way to talk about it and how people self-identify.

EMILY CAULFIELD: So, it’s much more nuance than just the overarching, I’m shy.

ALICE BOYES: Yes. So, when you break it down you can see more how those are useful tendencies. So, when you just call it shyness, it doesn’t make it obvious why it’s an objective tendency or why we would want some people in the tribe that are more prone to being cautious and more prone to overthinking, and more prone to caring what other people think. But when you break it down in those ways, you can see more, what the adaptive vices of it is.

EMILY CAULFIELD: Yeah. That’s very interesting. So, have you seen different ways that these tendencies will show up in the workplace for people?

ALICE BOYES: Yes, so all the things that you would expect. So, the time when people are expected to speak up, especially in unfamiliar situations. So, some people become much more comfortable once they know people. Because some people, their quiet tendencies or their shy tendencies, or whatever is, possess even when they know a group of people well. And with any of these sorts of traits or issues, their issues tend to come up more when the person is going through some sort of transition, or under extra pressure. So, people develop coping mechanism and then something about their situation changes. Like the person might become a parent, and all of a sudden, they can’t over prepare as much as they usually did. And so, if something sort of disrupts peoples coping, it can show up more or something about the nature of their role changes. Like their switch changes or they get a whole bunch more responsibilities. It can first seem dormant for a while for some people, but then just crop up as a stressor when something different is required of them.

EMILY CAULFIELD: You hit on two really interesting things about the transition and also the coping mechanisms. So, maybe I’ll ask you about the coping mechanism first that Laura brought up. Do they work? Not work?

ALICE BOYES: They can work. And that’s also the problem. So, there’re a real double edge sword. And treatment of social anxiety, those are all called safety behaviors. And the way safety behaviors work is people will take a friend. Like they won’t go to a party without taking a group of friends, so they’ve got someone to talk to, so they don’t actually have to talk to anyone new. And what happens is the brain jumps to the inclusion that the only reason it wasn’t a huge disaster was that the person used their safety behavior. So, they think the only reason I was able to do well in this situation is because I really over prepared. Or, the only reason I did well in this situation was because it was one on one, all of these kinds of things. And the person never learns that they could have coped if their fears occurred, so if they did appear anxious that it would have been OK. And they never learned that maybe that they could be OK without doing all the safety behaviors. And then they never learn that they could be OK without over preparing. And then that becomes a huge problem over time where people think that the only way that they can succeed is through being like highly perfectionistic, and then when more responsibilities come in, or in situations which they can’t be super perfectionistic and super over prepared, then their wheels start to come off. Or they start avoiding situations in which they can’t do those things. They take on this, like they just keep their life low of stress and then that sort of reinforces the idea that the person isn’t robust, that they’re a bit fragile, or whatever. So, the person’s sort of creating a self-fulfilling prophecy there and that can sort of further fade into a negative self-image that they’re just not as robust and not as resilient as other people.

I mean it sounded like Laura has done an amazing, amazing job of developing strategies and coping it across her life. And she said that it was working. She said that over time it had all gotten a lot better, and she had gained some confidence. But there was still some underlying shame and stuff there. So, the most potent aspect of treatment for social anxiety is exposure. And an example in this case would be, for example with over preparing, you would make a hierarchy to practice not over preparing. You’d put some behaviors on that hierarchy, and you’d write how anxiety provoking they would be from one to 10. So, like giving a presentation, not preparing at all might be a 10. And, doing a little bit less over preparing than you usually would be sort of things lower down on the list, or not preparing for a meeting with people you know, those things might be like a three or four out of anxiety. And what you do is you have the person practice not over preparing, starting near the bottom. Starting with things that are like a three and then practice things that are a three, then a four, then a five, and then they’ll work their way up. You know, decades of literature showing that type of exposure is an extremely potent way to lower anxiety.

There are certainly some things that you can do to have a different relationship with things like rumination and over preparing, and perfectionism that’s aimed at preventing disasters or hiding say flaws and all of those kinds of things.

EMILY CAULFIELD: Yeah, I re-listened to the episode from Season Two, “Perfect is the Enemy,” where the team spoke to you and you had a lot of great strategies. I would encourage our listeners to definitely check that out if they haven’t already. So, was there an aspect that you heard Laura mention that seems to be especially common amongst women?

ALICE BOYES: I think the aspect of not feeling like you fit with the traditional stereotype of a leader. We have the stereotype of a leader as being somebody that’s bold, that talks really clearly, that those skills have become very associated with leadership. A lot of that is a sexism thing, right? It’s these stereotypical masculine qualities have been associated with leadership. This podcast has talked a lot before about the double standards and how women are judged more harshly from mistakes than men are, and their mistakes are remembered longer, and all of that kind of thing. So, women tend to be driven towards perfectionism in part because of what they pick up on. For example, that you’re going to be judged on how eloquently you speak rather than the quality of your ideas, or all of those kinds of things

EMILY CAULFIELD: Yep. So, if you’re in a work scenario and you do find yourself having a visceral reaction to something that makes you anxious or feel shy, do you have any recommendations for what would be a good thing to do, or what would be a helpful thing for that person to do?

ALICE BOYES: Yeah. So, in terms of blushing, there is not going to solve the problem of leadership being associated with bold, loud people, right, and not being associated with those qualities of quietness and shyness and things like that. She can only solve the problem for her. And it will be like creativity that comes in here, and it might be that she’s sort of radically up front about it.

EMILY CAULFIELD: Calling attention to it or something.

ALICE BOYES: Yeah. It just becomes something that she does. Again, it comes back to the shame thing. It’s not the blushing that you need to overcome, you need to overcome the shame over the blushing.

EMILY CAULFIELD: Right.

ALICE BOYES: And so, I think looking at it like that, ask yourself, if I was having this happen, and I wasn’t ashamed of it, what would I be saying? Because it’s useful for other people to understand a little bit more because others will get equally awkward. They don’t know what to do, or how to react, and they’re trying to read the situation. The more that you can help the other people feel comfortable with it, the better.

EMILY CAULFIELD: Acknowledging it, yeah.

ALICE BOYES: I think that’s even OK to say, “Hey look. I’m having this reaction now, and I’m so consumed by this reaction, I’m finding it hard to listen to what you’re saying. So, can we just go really slow with this? Or, can we like figure out what the bullet points here, or can we figure out what the plan is? Because my brain is like a little bit knocked off. Some of my processing capacity is going toward thinking about this and kind of monitoring myself and not going toward listening to what you’re saying.” And that’s what happens to a huge proportion of people in some ways. Like I’m really sensitive about my accent, right? So, if I’m highly monitoring, like are people understanding what I’m saying then it’s hard to also think about what I’m saying.

EMILY CAULFIELD: Yeah. So, I’m wondering if you’re a person who’s on the other side of this and you have a shy colleague, what would be a good way for supporting them in a moment where you notice that they’re shy or if they’ve come out and told you that they have difficulty in certain situations? Is there a good way to support a shy colleague?

ALICE BOYES: Yeah. I think one thing that’s really important is not to encourage them to be bolder. Not to encourage them to use a loud voice, or not to encourage them to mimic somebody that’s not shy. Because that’s not the idea. The idea isn’t to just conform better to the stereotype. So, helping them understand their strengths and helping them see that those strengths are valued. Helping them understand that you enjoy some aspects of them that maybe they’re ashamed of. Like you enjoy their thoughtfulness. You enjoy their sensitivity. All of those kinds of things.

EMILY CAULFIELD: Yeah.

ALICE BOYES: It’s really important that anybody has mentors and colleagues that they have a close enough relationship with that they can be honest about what the things that they struggle with are. Like I know I should be doing this, but I’m actually avoiding doing it. And looking through that kind of thing. It’s not like about the shyness or about the blushing or whatever. It’s about the shame and the avoidance. Like is there anything that the person’s avoiding and helping them figure out a way to not avoid those things.

EMILY CAULFIELD: Right.

ALICE BOYES: But there is an extent to which people don’t have to do everything. Like if public speaking is just not something that is meaningful to you, or value, then maybe it’s not something that you really want to move towards. Then on the other hand, there might be, now or in the future, a time where there’s a reason that becomes meaningful to you, and you do want to, it is something that you want to tackle. And so a lot of that will just be stage to stage, really.

EMILY CAULFIELD: So, Laura right now is at a crossroads in her career. She’s worried whether or not she’s fit for a leadership position. I wonder if there’s a way where she could sort of highlight the qualities of her that she knows are positive. Being a little bit more introverted and being very thoughtful, and if there’s a way to highlight that in her transition, or think about ways to think about herself differently as a leader, going forward.

ALICE BOYES: So, anxious people are really, really good at getting things done when they find something that’s more important to them than avoiding anxiety. So, she has to think about why she is attracted to being a leader. Like she was saying she was worried that her growth was going to be limited by her shyness. What sort of growth is she wanting? What power will she have to do things that are really important to her when she’s a leader that she doesn’t currently have? So, it really is leaning into all of those other things. You have to find something that’s more important to you than avoiding feeling anxious or looking anxious. And the other way to sort of re-conceptualize things is to recognize that the goal is not to become less anxious or to hide your anxiety better. The goal is to be less ashamed of being anxious. So, keeping really like a bullseye on that. The actual problem is shame about anxiety or shyness, and not anxiety itself. So, I got like an undercurrent, and if I could talk to her I would ask her if it was true or not, but like an undercurrent that she thought her success as a leader was going to be determined by how good she was at hiding her anxiety, or hiding her shyness, or how good she was at getting herself to do things that were out of her comfort zone. And I would re-conceptualize that and have her think about how her success is a later will be determined by how well she uses her strengths. Like she knows she’s got those strengths. She knows she’s creative. She came across as incredibly charismatic.

EMILY CAULFIELD: Yes, totally.

ALICE BOYES: Yeah, an amazing resilient, amazing problem-solver, like all of that came through and stayed. And so, her success is a little bit determined by those things and by her using those strengths, not by how well she can hide her anxiety.

EMILY CAUFIELD: Yeah. Well, Alice this was a really interesting conversation. I feel like I learned so much. Thank you so much for being on the show today.

ALICE BOYES: Sure, yeah and thank you so much to Laura. Like it was such a delight hearing her story and her struggles and I just felt so proud of her, like hearing all the amazing ways that she has worked through this and how fast she’s got in with it herself. Like there was just that sense with her that she was just so close to sort of breaking living with it, and I think that is the level of recognizing the shame is the problem.

AMY BERNSTEIN: So, Amy G., Emily and I have already hinted that we both suffer from shyness, but you don’t seem as if you suffer from shyness. What’s up with that?

AMY GALLO: Yeah, I really don’t. That phrase being shy is not something I’ve ever felt like rang true for me. And I mean I do identify as an introvert, so if I have my choice, I’d prefer a quiet night at home to a cocktail party, any day of the week. But I don’t think of myself as someone who has social anxiety or hesitates to speak up. I’m not afraid of talking in front of a group. So, it was really helpful for me to hear more about what the experience was like for both of you. And actually, it was also really interesting for me to hear Amy B., that you identify as shy because that’s not something I would have pegged you as. And I’m curious for you, how does that shyness actually manifest?

AMY BERNSTEIN: Well, now it’s more internal than anything else. Or, here’s how it feels: If I’m on a WebEx meeting, I still get that kind of like should I or shouldn’t I moment before I leap into a conversation. But I almost always decide yes, I should. I should say what I need to say. But that is, that’s a 180 from the way I was 10 years ago. You know, Alice Boyes talked about, for some people shyness arises out of a real fear of, or a real concern for what people think of you. And I think I definitely had that and more to the point, I didn’t want to come off as an idiot. I was always highly aware of what I didn’t know and what expertise I didn’t have, and I’m sure that that’s sort of a perfectionist tendency, or something. But it definitely, definitely wrapped its fingers around my throat every time I thought about contributing. I just figured it wouldn’t be smart enough. It wouldn’t add enough value, so I might as well as just shut up.

EMILY CAULFIELD: Yeah, Amy B., I feel a similar way where I, I think of myself as an extrovert, but in the workplace I definitely have this sense of nervousness or this sense of anxiety around speaking up because I’m maybe questioning the value of what I have to say, or questioning my competence. Even if I’m pretty competent at something, I’ll still doubt myself and that will come out as this type of anxiety. So, I’m wondering what you did to work through that?

AMY BERNSTEIN: What happened is I turned 50 and that was, you know, that’s just a milestone birthday. And I started to take stock and I realized that I could, I really needed to sort of take control of my life, and that any frustrations I was feeling particularly at work were mine to deal with. Like I really couldn’t continue to wait for people to recognize my value. I was being too passive, and I just had to own that.

And then at the same time, there’s something about making it to 50 that makes you stop caring what people think. Now, maybe it was just me and my circumstances and you two don’t even know what this is like because neither of you have turned 50 yet. But it was such a liberating birthday for me. And that changed everything. So, of course I want people to think well of me, but that’s sort of a free-floating thing. It’s not that kind of micro-observation in every nanosecond of every day. I don’t really care. All I know is I know I’m doing the best I can.

AMY GALLO: But Amy you had, even prior to being 50, you had a lot of career success. How did you overcome that concern? How did you force yourself to do things when you were consumed with that concern of should I or should I not speak up?

AMY BERNSTEIN: Oh, you know what’s interesting? So that question made me realize something, that a lot of it is just the discomfort of being in groups of people I don’t know very well. But if it’s people I do know well, I’m totally comfortable, and that has always been the case. The other thing is as an editor, that’s heads-down work and that’s one-on-one relationships. So, that came very naturally.

EMILY CAULFIELD: Well that was one of the things Laura was concerned about – was like, could I be a manager? Could I rise to a leadership level in my organization if I’m shy? And I feel like Amy you were the answer, the clear answer that yes you can. And I’m curious, has any of this shyness felt like it’s held you back from leading or managing in the way you want to?

AMY BERNSTEIN: Not now. Absolutely not now. In the past, definitely. The other thing is that when it came to public speaking which I found – I mean like everyone – I found it frightening, but I’d get physically ill. I realized that this is the part of Laura’s letter that really resonated with me, it’s like if she couldn’t step up and do this thing that terrified her, she realized she’d never be able to take a step forward in her career. So, what I did was I realized that I just had to make myself comfortable with public speaking. Getting up in front of a large group of people whom I don’t know. And so, I said yes to every single opportunity because I knew that to move forward, I needed to be able to put myself out there. And that eventually worked. And now I actually, instead of losing sleep for two weeks ahead of an engagement, I actually wake up in the morning and look at my calendar and think, huh? Look at this. I’m supposed to lead a Webinar today. [LAUGHTER]

AMY GALLO: Emily, can you imagine getting to that point?

EMILY CAULFIELD: I can’t, but I am kind of, of the same philosophy where I’m trying to push myself to do things that are uncomfortable. So, now if I’m in a meeting I’m trying to speak up because I know that for years, I haven’t done that. I’m trying to take on opportunities that will be uncomfortable for me because I know that growth will come from them. So, even being on the podcast, as you all know, I tell you this frequently, how scared I am to do this. But I know that this is good for me. And I probably will always be a shy person, but I’m hoping that I get to the point where Amy is, where I’ve encountered these experiences enough where I can handle them and I can be OK with doing them and not be ashamed of my nervousness that might be apparent to other people.

AMY GALLO: Yeah.

AMY BERNSTEIN: I mean even in a meeting, when you say something, and the room responds positively, how does that make you feel?

EMILY CAULFIELD: It feels great. It feels great. It feels good to know that your idea resonates with other people and to kind of be proud that you spoke up. And I have sort of been more mindful in meetings about watching how the response has happened, and on WebEx or Zoom, it’s difficult for people to sort of chime in, in that natural way. But there have been times lately where I’ve spoken up in meetings and then I’ve had somebody chat, like send me a message and a chat, and it’s felt so great. It really reinforces the fact that it’s usually good to speak up when you have something to say. It’s always good to speak up when you have something to say.

AMY GALLO: Yeah.

AMY BERNSTEIN: All right, I’m going to ask Emily a question directly. Then I’m going to put you on the spot. So, I have led meetings with quite a few people attending, including you, and I have purposefully called on you. I have a feeling you have something interesting in your head, and I want to hear it, and I want to encourage you. How does that feel? Should I stop doing that?

EMILY CAULFIELD: Not, necessarily. It feels good to know that you value my opinion and you value my input. So, I think that’s positive.

AMY GALLO: But I do wonder if thinking about helping someone who is shy, whether it’s someone you manage or someone you’re mentoring, is putting them on the spot like Amy B. is doing for you in those meetings, is that helpful?

EMILY CAULFIELD: I think for me at times it is because I know that the way that I want to approach my shyness is I want to like approach it head on. And I want to do the things that make me uncomfortable. So, it might not be the right option for some other people who would prefer to kind of be off in the background and maybe share their thoughts or opinions through email, or however they’d like to do that. But for me, I know that this is something I want to push past, and I want to push past it by practicing those uncomfortable moments more.

AMY GALLO: Yeah, I mean my instinct when I think about the socially anxious, or shy people I work with, my instinct is to keep giving them opportunities and to do what Alice says of the sort of exposure to the event or to the thing that makes you uncomfortable. But I do worry that that’s not always the most useful. I mean, I also think about building someone’s confidence, so when they do speak up and say something that’s really helpful or valuable, of making sure to comment on that.

AMY BERNSTEIN: Yeah and acknowledge that.

AMY GALLO: Yeah and call it out in front of other people so that they know they’re going to be rewarded for taking those risks even though they’re uncomfortable.

AMY BERNSTEIN: But you know, something that you guys have been talking about really is making me think that we have to be more nuanced as managers, and that is to sort of figure out the best way to give each person the opportunity to contribute. If the best way for someone to contribute is to write an email, I mean one of the things that hit me about Laura’s email is how beautifully written it was. I mean, first word to last, absolutely beautifully written. And clearly this is the mode of expression she’s most comfortable with. Nonetheless, for Laura to move ahead she’s going to need to standup in front of a group and speak. So, you know, even as I’m thinking about this out loud, I think that tailoring the communication to the needs of the individual team members is good on the one hand. It also may not serve their longer-term interests on the other. I think it needs to be handled carefully.

AMY GALLO: Yeah. Like actually figuring out what they feel comfortable with, what’s the right way to push them?

AMY BERNSTEIN: Yeah, but also understanding how they want to develop and where they want to go.

AMY GALLO: Yeah, right.

HANNAH BATES: That was former clinical psychologist Alice Boyes – in conversation with Amy Bernstein, Amy Gallo, and Emily Caulfield on Women at Work. If you liked this episode and you want to hear more about how gender shapes our careers, check out Women at Work wherever you get your podcasts. We’ll be back next Wednesday with another hand-picked conversation about leadership from the Harvard Business Review. If you found this episode helpful, share it with your friends and colleagues, and follow our show on Apple Podcasts, Spotify, or wherever you get your podcasts. And while you’re there, be sure to leave us a review. We’re a production of the Harvard Business Review – if you want more articles, case studies, books, and videos like this, be sure to subscribe to HBR at HBR.org. This episode was produced by Amanda Kersey, Anne Saini, Ian Fox, and me, Hannah Bates. Music by Coma Media. Tina Tobey Mack edited the original episode. Special thanks to Rob Eckhardt, Maureen Hoch, Adi Ignatius, Karen Player, Ramsey Khabbaz, Nicole Smith, Anne Bartholomew, and you – our listener. See you next week.