Psychological Safety for Quiet People — From Networking to Leading More Inclusive Teams

Have you ever walked into a networking event or even a fast-paced meeting and just felt the energy drain from your body before you even set a word? Welcome to the Introverted Leader. It’s a podcast helping introverted leaders embrace your underrated, quiet strengths so you can get promoted and start earning what you deserve. I’m Greg Winder. I have over 25 years of leadership experience and yes, I am an introvert. Today, I’m joined by Anna Grady. She’s an executive coach and a former tech CEO who now helps leaders, especially women in tech, build confidence, quiet their inner, critic, and foster cultures of psychological safety around them. This is a very practical conversation. Anna shares tools made just for introverts that you can start using immediately. This includes number one, how to network like an introvert using small goals, great starter questions, and a focus on quality over quantity. Number two, a really great definition of confidence. This blends action with self-compassion in a way that lets you grow. And number three, simple ways to create psychological safety in your workplace so quieter voices can be heard. If you’ve ever felt like leadership demands something of you other than your authentic self, this episode is like a permission slip to be just as you are. Here’s my conversation with Anna. Welcome to the show today, Anna. Thank you so much, Brink, for having me. It’s an absolute honor to be here with you today. We’re both in the dark as we record this where you’re in Vancouver. I’m in Portland or just on the Pacific Northwest just gearing up for winter. So thanks for joining in the dark this time of year. My pleasure. You know, this is powerful introvert podcasts. So I have to know, are you an introvert or an extrovert? I’m an extreme introvert. All right, let the record reflect this. And so please tell me about your origin story as an introvert. When did you realize it? How was it like for you growing up and going from there? Yeah, I’d be happy to. So I’ve always been extremely shy. I was an extremely shy, just a child at about age eight. And my very scary uncle introduced me to a new family member and he said, you won’t hear much out of this one. I remember my cheeks lighting up with embarrassment. And I always felt like there was something wrong with me. I had a lot of shame around being the quiet one in the room and needing to prepare for sharing my thoughts. I spent most of my life trying to overcome my introversion. So I had a family story. Sorry, the scary uncle. A lot of us have the scary uncle. Yeah, mine used to pick me up and put me on the shoulders. And you know, it was just too much. When did you start to catch on that you weren’t introvert? Yeah. So I’d always known there was something different. I was quieter than most. But what’s really until I read Susan Cain’s book Quiet in 2022 that I realized introversion wasn’t something to be ashamed of. And it could be in fact, a leadership strength. Looking back, I realized my introversion actually helped me in my career. It helped me build my tech company. It helped me manage my team. And now it helps me coach my clients. That’s awesome. I think like a lot of people here, I mean, I have this my copy of Susan Cain’s book right here by my desk just because it comes in handy. But yeah, that was a watershed moment for many people that I speak to just in the world that are in particularly on the podcast. To me was kind of like an owner’s manual of this is how you are and this is how the world is organized and just brought me to much more acceptance. You’re like, okay, I’d just different almost to the point of pride. This is a strength. Yeah. Yeah. Took me to that moment to realize it until leave the shame behind. So your co-founder is that right? And then what was your role or title in that organization? I was the COO and head of H.R. So you’re obviously displaying the strengths of an introvert, but at the same time you were kind of fighting that. Can you say more about that? Yeah. So I need more time to prepare for public speaking, for meetings. I have a lot of notes always and it was a challenge. I always had to kind of talk myself into doing things that were more extroverted and feeling like there was something wrong with me. It kind of carried with me in that journey as much as I tried to kind of fight against it. It was always there and it was always something that I had to handle on an ongoing basis. Right. So you had to do this work to prepare and do the types of things that we have to do as introverts to handle these situations. But there is this additional layer of feeling shame or just bad about that. There’s something wrong that I have to do these things. Yeah. And my co-founder was very extroverted. So I always kind of compared myself to him and felt kind of less than. It was a struggle. It was a joy to do all these things outside of my comfort zone. A lot is a person and as a leader. But I have myself back in a lot of ways. Yeah. And so it sounds like you gained confidence in the role that you’re doing it. You’re being the leader and you’re pushing yourself, pushing your boundaries and getting these new experiences. So you were successful. You were confident. You were this leader. I learned that confidence doesn’t have to be loud. Sometimes it is okay if it’s quiet. And being silent or more concise can actually be more effective. And if you don’t have the answer on the spot, it’s okay to say, let me check that out and get back to you. And I learned that asking questions is a great way to contribute in meetings and to kind of practice speaking up. So so far your journey has mirrored mine quite a lot. I didn’t go found a company but I’ve worked in tech 25 years. But very much that’s a thing I had to develop and display a different model of leadership. And I made it work and I figured out all these things and then just still felt like there’s something off about it. So then you realized, okay, well, I don’t have to feel this way about it. So how did things change for you after that? It probably didn’t really change when I was a leader in the tech company. It was after when I became a coach. That’s when I really understood the power of being an introvert and how I could connect with my clients. Really well one-on-one, how I could understand the introverted experience by working with introverted clients. So it really was after my role in my tech company that I was able to leverage my strengths as an introvert and really own it and see it as a gift and not as something to hold me back. How did you decide to do coaching after the tech company? Good question. So I was blindsided by a very painful divorce in 2019 and I hired a coach to help me pick up the pieces of my life. And that put me on this journey of self-discovery, personal growth and transformation. And in that journey, I made a decision to take an exit from the tech company I built and to pursue coaching full time. And that’s what I realized I wanted to help women leaders specifically in the tech industry because there is that persistent gender gap in tech. And my heart goes out to any women in tech. I work with women in tech and I try to be their biggest allies and I can because I know what they’re up against. Vastly outnumbered and there’s too much toxic masculinity still. Yeah, thank you, Greg. Well great. I’m so glad you’re doing this work out here. And then you developed your own method. This is something I don’t think I’ve adequately defined on my podcast because I too went to a coach and did personal transformation work. How would you define that? What is personal transformation work? What are we talking about? Yeah, so working with a coach, it’s somebody holds up an objective mirror and asks you those questions to access your inner wisdom. Coaching isn’t about giving advice. It’s about asking powerful questions to access the answers that are already inside you. So having that safe space to explore the different parts of yourself and have a deeper understanding of who you are and learn to love who you are puts you on this path of transformation and personal growth. It can be difficult, it can be emotional, but you take a hard look about your strengths, your weaknesses, what you want to change about yourself, how you want to show differently in the world for yourself, for your family and for your community. And that’s the transformation and it is ongoing as humans and if we work with coaches, it can really fast track that transformation. Absolutely. It’s a wonderful definition. So let’s dig into your method at the Phoenix transformation method. Of course, so the Phoenix transformation method focuses on developing emotional intelligence, reducing negative self-taught, allowing your life with your core values, setting healthy boundaries, learning to fail fast and get outside your comfort zone and take more risks, trying new things, leading with purpose. What is your why, why are you on this planet and what is your purpose and cultivating self-compassion, really strengthening your relationship with yourself and creating healthy habits like fitness, mindfulness and meditation. So these things, they all seem very important, checking the boxes off there. From me, it started with a lot of deeper understanding of myself and then acceptance of yourself and kind of going deeper into that. But then coming out of that, identifying purpose, and like as you said, what’s your why, is that the general progression, what is the progression for you? Yeah, so I did play with clients for about six months. I have a structure that we follow typically from each session to session, but it’s also very customizable to the goals of the specific leader in front of me. So my approach is customized to their goals when I have this kind of structure and it yeah, it starts out with a self-awareness piece, kind of core values work we do right at the beginning. Then we move into how we self-savotage and have reducing that negative self-talk and creating those healthy habits like fitness, mindfulness too, weekend those savagetroid voices we all have. And then focusing on how we can get outside of our comfort zones, get outside of our own way and tackle those goals and challenges head on. And then near the end of the six months, it’s about purpose and who you are and why you’re here and what your life purpose statement is and how you tweak it and leverage it to make those bold decisions for your next chapter. In your practice, you’re focused primarily on helping women in tech. And so being a man in tech, I’m curious about if the people you work with, a lot of introverts will especially people in tech sort of intellectualize everything. And so your thoughts are your guard, your armor that protect you from dealing with more painful emotions. And so I’m wondering if you see that as a pattern in women in tech and with your clients and if so, like how do you approach that? Yeah, a lot of my clients are very analytical. The left side of the brain is very developed, very focused on analysis and that can lead to paralysis as we know if we over analyze. So it’s all about bringing that emotional side into the mix. We are all emotional creatures. I want to normalize. We all feel we all experience emotions. Some of us quite deeply met healthy to assess those emotions and often in coach email see there’s something happening emotionally with my client in front of me and I’ll ask what emotion are you experiencing right now to increase my clients emotional vocabulary to understand the different nuances of the different emotions we experience. So we can label them and have a deeper understanding of them so they can process more healthily through us. And so we have that awareness of our emotional world because we all have that experience. So you’re able to get in there and support their growing awareness of the side of them which we like to pretend that we’re not run by our emotions, but we actually completely are and so yeah, that’s very helpful information. Yeah, that regulation of those emotions, right? So what can you quite reactive to different triggers based on traumas we’ve experienced as children and affecting us throughout our lives. So being aware of those triggers. What are those triggers and that we can practice pausing and choosing more appropriate responses than reacting. Do you also appeal to the scientific inclinations of people so to help overcome skepticism. Is there information about practices like how do you get out of your head and overcome rumination or overthinking that kind of thing? Yeah, I love that question. There’s a simple science based practice I use and teach my clients. It’s labeling your thoughts. It comes from neuroscience, mindfulness research. When you name what’s happening, for example, saying to yourself, I’m noticing a replaying that conversation or this is my mind could test your fencing again. It activates the prefrontal cortex, the rational part of the brain and quiet the amygdala, which drives anxiety and rumination. It sounds small, but it can be a quite powerful shift. You go from being in the thought to observing it and over time, this helps you break that loop of overthink healing out of analysis paralysis. Excellent. Yeah, that’s definitely helpful. It’s amazing how much these things are well backed by scientific studies these days. Yeah, lots of tools like that. And do you do assessments, personality assessments for your clients as well? So I’m a certified in the EQI 2.0. That’s the emotional intelligence assessment. That’s an assessment. I do quite early on in the six month journey of working with clients. And this assessment helps with self awareness, understanding your strengths, your weaknesses and any blind spots. And once I get the scores on all 15 emotional intelligence competencies, we look at specific ways to increase some of the lower scores or many decrease some of the higher scores. The goal is to have a balance between the different EQ competencies without relying too heavily on your go to strengths. We created an action plan to help you stay accountable to the action plan. I check in with you between coaching sessions to make sure you run track. And it’s very customized to the specific scores and emotional intelligence of each leader in front of me. So you’re really starting from square one grounding and understanding helping to develop that awareness of their own emotional intelligence. It was really interesting. You said you actually focused on trying to decrease some of the higher areas. Do you have an example of something like that? Yeah. So sometimes we have very high areas that aren’t serving us. They can be blind spots actually. One of my clients, her optimism swore was through the roof. And a lot of time it wasn’t in. And so she has to kind of temper that optimism sometimes in some situations and really be a bit more objective. Yeah, it’s just philosophically. There’s the Marcus Buckingham go focus on your strengths and this whole idea is that you can’t be great at everything. And so really to have the maximum impact amplify where you’re strong and you might help some of the things where you weaker because you have to but understand you’re never going to be great at this thing. This sounds like it’s a slightly different framing and it makes sense, but it’s just different. Yeah. And sometimes our strengths when they’re overused, they can be abused and become sabotages as well. Or was to be mindful of that. Yeah. That was a great insight. So Apple bus for those of us who are maybe we’re highly empathetic, but also people, please, how do you help people who maybe shouldn’t do so much people pleasing? So many of my clients are natural empaths and people, pleasers who care so deeply about others, which is a superpower and the key to leadership. But it often comes at the expense of their own boundaries and energy. So my goal is to help these clients learn to advocate for themselves and care for others the same time because you can do both at the same time. And the science ties back to emotional intelligence, specifically the balance of empathy and assertiveness. Empathy helps you tune in to have others feel and assertiveness allows you to express your own needs respectfully and clearly. And when you combine the two and you create a win-win to an occasion, one of the ways to do this one practical way is to say, here’s what would work best for me. How does that land for you? So be mindful of your own needs and the needs of your audience who you’re talking to and try to have that balance where both needs take it into consideration and you don’t neglect yourself, walk my clients, prioritize everybody else over themselves. And that leads to burnout that leads to mental illness. That is no way to model what it is to be a human in this world to your family, to your community. And it can really take its toll on you. So be mindful of that and learning to prioritize yourself while still being mindful of the needs of others. Sounds like having that balance is so key. Is assertiveness one of the emotional intelligences? Yeah, that’s a well-balanced competency. Yeah, it makes perfect sense. And with a lot of people I talk to and often introverts naturally are lower in this sort ofness, not a hard and fast rule. But that’s a common pattern of high empathy, maybe a little bit lower on their assertiveness, especially earlier on. And that’s what I see on the emotional intelligence assessment every time when somebody is very high in empathy, the assertiveness score is low and vice versa. It’s a, and the hence balancing them out if it is the key. But the effective communication is when you’re able to balance empathy and a serve. Yeah, and it strikes me this is great for relationships too. You have a dynamic of two people. What do you want to do? I don’t know. What do you want to see? They’re trying to anticipate what the other person wants to make everything right. And the formula you shared earlier is just so perfect. It’s like this is what works for me. But what do you want? It’s just being genuinely concerned and wanting to know, but also putting what you want out there. Yeah, and it’s so important, especially if a woman in tech to be assertive, to have a voice, to advocate for themselves, and to be able to advance in their careers and ask for what they need. And how do you counsel people to build confidence? What’s a good way to approach that? Yeah, so confidence, the definition that I’ve come up with after five years of doing this work, it’s confidence is your willingness to try, to take action and then to treat yourself with compassion when you fail. So it’s all about taking those bold actions, getting outside your comfort zone, being willing to try even if you don’t feel confident and that builds confidence when you see yourself doing new things. And then the key piece is when you fail, when you make a mistake, to treat yourself with compassion. And that gives you the confidence to keep going and to try again. So it’s just loop. And it’s based on taking action steps that are outside your comfort zone and then being kind to yourself if it doesn’t go as planned. And know that perfectionism is another pitfall. One is just not even trying things because your perfectionism can lead to procrastination and then it’s not being kind to yourself when you fail. I’m a recovering perfectionist, 100%. And the first step is self-awareness. It’s understanding the downsides of trying to be perfect all the time. What is it costing you? And what do you not pursue them because you want to be perfect? Is that analysis paralysis again? And then a strategy that I recommend is dividing up your tasks. So it’s starting to be excellent in 20% of the areas in your life and being okay with being good enough in 80% of the areas. So for example, striving to be excellent in high stakes conversations by preparing, by rehearsing possible scenarios, but then being good enough in your administrative tasks and forgiving yourself for a few minor mistakes. You can’t be perfect in every area. There’s not enough cars in the day. No, don’t know that raw. Yeah, and it’s just exhausting to try to hold yourself to that standard. I think it gets addictive. Dopamine thing like I’m the best at checking things off my list and the best dog walker there is and the best parent. Yeah, it’s never ending. So networking as an introvert tell us how you learn to tackle networking. Yeah, I really love this question. It has been a struggle and kind of a success in my life. I always believe I couldn’t network. I was too introverted to shy. Introverted people are good at networking. Those were the beliefs that I had. But I learned early on. The number of way to build a business is to get out there and network. So I was determined to be glad it to be a perfectionist at it. And so I went out there and I went to events and I learned so many things along the way. It was terrifying, but I’ve learned to really enjoy networking to have fun with it. And to use my introversion as a real strength in creating those deep quality connections. It’s really about quality connections that you make not collecting like 100 business cards and having superficial connections. I find this is led to opportunities, collaborations, friendships, clients by creating those deep relationships through networking. And you point out a common strength of introverts is once you do make a connection, we like to go deep. And so you can make really deep quality connections. It’s the preamble to that, which is, I think, is a little bit more terrifying. Could you walk us through how you approach an event, do you do anything to prepare and what happens when you walk in the door? Yeah, so I do have some strategies that I’ve developed over doing this for, I guess, about five years now, being active in the networking world. So I always like to set a small goal in advance, like talk to 3 new people, something achievable, something small. And I’d pair a list of questions to ask and have knowing the audience, knowing the event, have some questions in my back pocket can be really, really helpful when I first go up to people and start talking. And network compares, form networking buddies, where you need networking events often two people are more approachable than one. This is one of my favorite pieces of advice is be more interested than interesting. So it’s not about talking about yourself. It’s about asking questions about getting to know somebody. I have to complement someone’s outfit. That’s a great way. Oh, I love your scarf. I love your suit, whatever it may be. Go into someone just complimenting them as opens the door to a positive interaction. And like I said before, focusing on the quality connections over quantity and don’t be afraid to get personal and talk about things that you haven’t common being a mother, things you like to do for fun, for example, don’t have to all be work focus and then always be of service. I like to always end with a question. What can I do to support you? How can I support you and who can I connect you with to help you in and your business? That’s a great one there. I heard that before and it seems like that’s a cornerstone of networking where if you are genuinely trying to help other people, if you’re curious, like you really care and are interested in then genuinely want to help then that seems like a recipe for forming strong connections. Yeah, and there’s some things as an introvert that I’ve learned to do as well. Scheduled downtime after the events, celebrates that you put yourself out there and don’t schedule three back to back networking events in one might like I did. The bleach report app is your destination for sports right now. The NBA is heating up. March, Manus is here and MLB is almost back. Every day there’s a new headline a new highlight a new moment you’ve got to see for yourself. That’s why I stay locked in with the bleach report app. For me, it’s about staying connected to my sports. I could follow the teams I care about, get real time scores, breaking news and highlights all in one place. I know I learned a hard way that that’s not a good idea. Yeah, it sounds rough, but you survived. So, you know, and not all networking is in person. So what about online networking? Yeah, I do a lot of it is pretty much the same kind of always be enough service asking questions scheduling one on one virtual meetings after the event to know somebody. I was like to kind of remember the details of our conversations in a follow up after the session to kind of show up that I was listening in that I care about what we were talking about. Yeah, do you take notes? Some people just have really good memories or have develops ways to remember things, but do you have any suggestions for that? Yeah, I’ve always been in an attention to detail person. I always remember little details. Sometimes we can really random detail about conversations that helps me and in person, I don’t have ability to take notes, but online for sure. So moving on to various things that seem scary to introverts, especially moving to the leadership space, public speaking, and you know, representing your work. If someone comes to you when your coach has said, well, yeah, actually have a lot of stage fright. How do you help them? Yeah, I suffer from this even to this day. This has been a major hurdle to overcome and what really worked for me and what I always recommend for my clients is to join toast masters. Joining toast masters gives you weekly exposure to speaking. It helps you see where you can grow in speaking, you have kind of blind spots and you have that community of people supporting you, giving you on demand, like evaluations of your speeches right away, tracking your arms in your eyes that can be really helpful in it. It’s really about practice saying yes to speaking opportunities at work, taking improv class. That’s a great way to learn public speaking and to be less fearful of mistakes and to take more risks. And what’s your approach to persuading people to take action by always being of service by listening by showing the cost of not taking action like the cost of not pursuing coaching. Where could you be in your life if this was something that you did pursue. It’s opening them up to the future. How things might be different. Yeah, I just love the advice where someone’s mind is made up. You’re like, okay, well, I understand the answer is no. But let’s say the answer is yes, how could that work? If you’re almost like tricking someone into using their imagination and then before you know it, they’re solving your problem for you. Yeah, and no right now could be a guess in the future. I learned really early on in my coaching career to celebrate all the nose and to track all the nose because it could be a no right now, but it could always be a guess enough. You shouldn’t have means you’re putting yourself out there. Yeah, it might be a no, but if you’ve given something of value to them, then you may be helping them. You’re kind of putting that out there. So as a leader, how do you create environments, work cultures that are more supportive of everybody? And so that’s about fostering psychological safety. What advice do you have for promoting a safer environment in the workplace? Yeah, so there’s a few practical strategies to help bring out those plighted voices in the room and to lead for all personality types. And what I would say is start off with reflection time at the meeting. So instead of jumping right into discussion, give people a chance to reflect, take some notes for down their thoughts. And in reverse, we think before we speak so that can help us organize our thoughts and be able to put our best foot forward in that meeting, use round robins, if one around the room and asking each person for their input on something before open debate begins. Prevent said two people from dominating the conversation, which is often the case. And then normalizing a synchronous input. So sometimes our ideas don’t come right on the spot as introvert me some time to reflect in process. So having Google Doc or a Slack channel, something where we could add information after the meeting, it can capture some insights that weren’t really there on the spot. That’s a way to help different personality types. And then the idea of leaders going last when managers speak first, it can unintentionally shut down others, so going last models curiosity and contribution. Yeah, good suggestions. So this is about getting feedback and fostering these discussions. What about what it comes to decision making? Sometimes leaders have to make a call, but if it is a situation where you want more distributed decision making, how do you foster that, especially with quieter people involved? Yeah, just kind of slowing down the process. So more voices can be heard and not just the loudest ones. The structure matters. So this using phrases like let’s explore that perspective to show that all perspectives how value and seeing curious and not defensive. Invite that be a dialogue and that open mindedness. Right. You’re really setting the tone as the leader about how this discussion is going to unfold. And it’s also a bit about what you tolerate behavior in the room and do tolerate people talking over each other or interrupting each other. What’s something an introvert can do to build confidence? So confidence isn’t something you’re necessarily born with is something that you can build. And for introverts, I recommend daily stretch actions doing something outside your comfort zone. Something that align to the poor values, but it’s a bit of a stretch for you can be a great way to build confidence. And as you do more things outside your comfort zone, you get more practice in that kind of built competence, which then builds confidence in this loop. So for example, speaking up like three times in a meeting, for example, or reach enough as somebody you admire or simply sharing your opinion before it’s polished to show your brain. I can handle this and I can do something that’s not polished and perfect. And ending the day with self compassion is so key not getting yourself off, not ruminating for what you didn’t say or what you should have said or what you should have said differently. It really comes down to the release that you have with yourself and owning who you are and not trying to overcome who you are. I like that. That’s reminding me of the suggestion of having a gratitude journal or something you do at the end of the day. It’s almost like a self compassion journal. Kind of take it easier at myself that today. Yeah. And my coaching calls we always open with introduction and sharing three wins from the past week. So tracking your wins that our brains are hard barred to focus on the negative for survival reasons. So it can be really powerful to track those wins big and small. Like what went well today and that reflection at the end of the day. And how could I be more self compassionate? Great. Great question. And if you had one personal message that you could give to quieter leaders who maybe feel like they’re not enough, what would it be? Introversion is something to be celebrated, not overcome. Your ability to reflect, connect deeply one on one, listen to others, observe, collaborate, our leadership superpowers. The world needs leadership strengths that you have. Be proud of who you are and don’t spend your life trying to overcome your introversion like I did. This has been a lot of fun and thanks so much for being here. If people want to learn more about your work, where can they go? Yeah. My website is anagradi.com. It was a great place. I’m also very active on LinkedIn. And I offer a free clarity call to anyone who’s interested in one-on-one coaching, my group coaching community or confidence building workshops. Awesome. Thanks so much for being here. Thank you so much, Greg. Take care. Okay, let’s take a moment to recap what Anna shared because there are really great ideas here that you can start applying immediately. First, remember networking doesn’t have to mean working the room and collecting dozens of business cards. Start small. Talk to a few people. Prepare a couple questions just to get yourself going and focus on quality connections. Those one-on-one conversations that you are so good at as an introvert. Next, start noticing how you think about confidence. According to Anna, confidence is your willingness to take action and be willing to treat yourself with compassion when you make mistakes and we’re all going to make mistakes. So it’s really about gradually building that confidence over time. And third, practice creating safer spaces for yourself and for the quieter people around you. Whether you’re running the company, leading a meeting or just being a participant in one, there’s always opportunities for you to speak up and advocate for yourself and quieter people. Add or suggest reflection time. Invite round robin input. Normalize asynchronous idea creation. Letting people build things offline and then bring them to meetings. And if you’re a leader, try speaking last. These are small choices that make quieter voices far more likely to contribute. If this episode helped you, here’s one simple next step. Subscribe. So you don’t miss out on a single episode, especially if you’re working on visibility, confidence and leading without burning out. I’m Greg Weinger. Keep leading quietly and I’ll see you next time.