Prioritizing Authenticity and Cultural Fit in the Workplace with Lesley Pinckney

Lesley:

When you sit in a meeting with Heinz, then you sit in a meeting with Oracle, and then you sit in a meeting with Budweiser, you start to see a pattern. We’re having similar conversations in all of these places. The products may be different, the challenges may vary, but ultimately, it’s about convincing people to do something.

That hit me at a very early age—it’s less about the industry and more about psychology and basic human nature. It’s about figuring out how to get people excited to buy a bottle of ketchup. That realization grounded me in a customer-first orientation. I thought, If I can always figure out what motivates people, I can be successful in what I do.

Gillian:

Welcome to Future Works, a podcast dedicated to conversations about innovation within the workforce space. We’re here to share research, inspiration, and a glimpse into what we’re building and learning at Aspect.

Today, we’re thrilled to be joined by Lesley, who we’ll introduce in just a moment. On Future Works, we dive into conversations with leaders, scrutinize case studies, nerd out on theories, dig into psychology, and explore what it takes to reinvent solutions within the workforce industry.

Michelle:

I’m Gillian.

Gillian:

And my name is Michelle. We are your hosts, leading you through candid conversations about what’s happening in the world of work and how things could be better.

Today, we’re talking about corporate authenticity—a combination that often feels forced. We’ve all been in those meetings where the two collide, and corporate “authenticity” boils down to the company delivering terrible news.

I won’t say they’re opposing forces, but they can feel like ice cream and cheese. It takes a skilled chef to bring them together with intentionality. That’s what Lesley excels at—this masterful blending of corporate goals and authenticity.

We want to create spaces where all folks can show up safely and as themselves. There’s no one better to dissect this topic with than Lesley.

Michelle:

Lesley, I honestly don’t even know where to start with your background. I could talk about your impressive resume, which includes MTV, Essence, and Intel. I could highlight your drive for successful outcomes, your creativity, or your ability to adapt and solve pain points with thoughtfulness.

But we’re not going to start there. Instead, I want to start with food. Since I’ve already brought up ice cream and cheese and since food is a universal human experience, I think nothing brings out authenticity more than a shared meal.

So, let’s start with this: what’s the best meal you’ve ever had?

Lesley:

Oh wow. Okay, the hard-hitting question!

I don’t know if you know this about me, but I’m obsessed with food. I love all things food—I live in Chicago, I love to cook, and I start thinking about my next meal the minute I finish the last one. It’s such a central part of my life.

I couldn’t agree more—it’s how you connect with people. There’s a sense of ritual, and it’s such a great way to explore other cultures.

You caught me off guard because I’ve had so many great meals, but I’ll share one that stands out.

Michelle:

It could even be your most recent amazing meal.

Lesley:

Okay, so last year—or maybe two years ago—we went to Mexico City. For those who haven’t been, it’s truly the food capital of the Western Hemisphere right now. The culinary scene there is incredible.

We happened to visit during ant season, and we went to this tasting menu restaurant where every single dish featured black ants, a delicacy there. I’m not skittish about trying exotic foods—my wife is, but she powered through.

The experience was incredible. Each course incorporated ant matter in creative ways, and it was surprisingly delicious. It was a completely multi-sensory dining experience, and it’s something I’ll never forget.

Michelle:

That sounds incredible.

Gillian:

It really does.

Lesley:

It was amazing.

Michelle:

For me, one of my favorite meals happened on a kid-free trip to Saint Lucia with my husband. We ended up at a local street fair that happens every Friday.

There was this local guide who took us to where all the locals go for food. I’m not a huge lobster fan—probably because I live in a landlocked state—but my husband got the lobster.

It was from this small, outdoor stand, and it was the freshest, most incredible lobster I’ve ever tasted. I was so mad at myself for not trusting the process and ordering it too.

Lesley:

Right, right.

Gillian:

It’s funny, Michelle, because mine involves lobster too. My answer to this question is the most amazing meal I’ve had—and also the one I want right now. It’s cold out, I need a warm soup, and I’m feeling a little under the weather.

I had this lobster soup in Iceland, and any time someone tells me they’re going to Iceland, I’m like, If you don’t try this, I’ll be mad. You know that feeling when you’re like, Please just listen to me on this!

Lesley:

Right.

Gillian:

I had it at a high-end restaurant, and I also had it at a fish market. Both were equally incredible—the only difference was the presentation. It’s a tomato broth, almost like a bisque, with chunks of Icelandic lobster and who knows what else. The texture, the warmth—it’s exactly what I need right now.

Lesley:

I come from a long line of Black Southern female cooks in my family. My whole upbringing revolved around kitchens and tables—chopping, making, and sharing food.

For me, both personally and professionally, food is where I spend most of my happy thinking time. Whether it’s, What are we going to eat today? What am I going to cook tomorrow? What restaurants should we try? Where should we vacation to find great food?—it’s definitely a central force in my life.

Gillian:

I love it. Speaking of your life, we’d love for you to give an introduction, some background, and context about your professional experience. What are all the good reasons we’re here today, speaking with you?

Lesley:

Sure. I was born and raised in southeast Queens. Both my parents worked in public sector jobs—my mom was a school social worker, and my dad worked for the city of New York in various roles.

Early on, from the moment I could articulate words, I wanted to be a doctor. That was my dream until I got to Cornell University and realized, These aren’t really my people.

That realization kicked off what was sometimes a self-destructive but ultimately beneficial journey of figuring out what I’m actually here for and what I’m good at. Growing up with such a strong sense of, This is my plan, and then having that ripped away—even by choice—was disorienting.

I ended up leaving Cornell without a degree. I’d always been good with computers, and this was the early ’90s. When I got back to New York City, email was just starting to catch on in workplaces. I remember my last semester at Cornell was the first time we had to use email to check our grades.

Some friends of mine were party promoters, and I thought, Is there a way to send an email to everyone? It sounds simple now, but back then, people barely knew what email was, and tools for that didn’t exist.

I went to the library—that’s what I do when I’m struggling—and started teaching myself how to program. I had a Commodore 64 and had always been interested in computers. I even spent a summer at MIT in high school.

Around that time, the internet started taking off. In mid-’90s New York City, the internet industry was incredibly diverse, arts-based, and culturally driven—very different from what it is today.

That early exposure to the internet allowed me to rise quickly in my career. By my mid-20s, I was pitching CMOs and CEOs at companies like Oracle and Heinz about building websites.

Weirdly, I was never intimidated in those moments because I naively thought, I know something they don’t, otherwise they wouldn’t have brought me into this room. That mindset gave me confidence.

I worked hard—first one in the office, last one out. I outworked, outshined, and outperformed everyone. Eventually, I was promoted to manager, and that’s when I realized, Oh no, what got me here isn’t going to make me successful here. I didn’t know anything about being a manager and had to learn quickly.

I’ve always been good with people, and I leaned into that as my superpower. I made an effort to know my colleagues—where they went to school, their family stories, their context.

My technology skills got me into rooms I wouldn’t have entered otherwise, and I started to notice patterns. Sitting in meetings with Heinz, Oracle, or Budweiser, I realized we were having similar conversations. The products and challenges were different, but ultimately, it was about convincing people to take action.

That’s when I understood it’s less about the industry and more about psychology and human nature. If I could figure out what motivates people, I could succeed.

That worked well in the digital space, especially in the ’90s when everything was still new. I worked for a series of digital agencies in New York, but then 9/11 happened.

The digital industry took a pause, and I didn’t know what to do. I had recently left a job, and there were no new opportunities. A friend of mine asked me to help with a concert production. I thought, I love music, why not?

That concert turned out to be for Michael Jackson.

Michelle:

You just casually dropped that!

Lesley:

I mean, it’s Michael Jackson. Back then, he was the biggest star on the planet—like Taylor Swift and Beyoncé combined. Production work was revelatory in a whole new way because it wasn’t about what you know at all.

I mean, yes, there are technical aspects to the job, but it feels very different than being in an office. It feels much more social.

Working in production—and also in entertainment—tends to be, in my experience, less of a meritocracy than other fields. I’ll probably get angry comments about this, but it’s what I’ve observed.

You have this dynamic in production where it’s not necessarily the smartest people in charge. It feels like the equivalent of a high school lunchroom—it’s highly social. And in that moment, I saw how workplace dynamics impact the final product.

There was this insatiable desire for people to cozy up to those considered the “cool” people in production.

Michelle:

What did that look like?

Lesley:

It looked exactly like it does in high school—people bullying others, wanting to be part of the in-crowd, and creating an “us versus them” mentality. I was new to this, but even as a lowly PA, I had come in through a leader of the production. That gave me a unique vantage point to see both sides of the dynamic.

What struck me the most was how many great ideas never even made it into the room because of this social hierarchy—this “high school lunchroom” structure that permeated production.

I’ll never forget being in a room discussing who should introduce someone at an event. I can’t recall who we were trying to find, but I suggested Graydon Carter from Vanity Fair. Back then, magazines were still big, and he was a cultural icon.

All these West Coast film and TV people were like, Who’s that? That’s when it all clicked for me.

If you only surround yourself with people who are just like you—or who are trying to be like you—you miss so much.

In today’s business economy, which feels like a bloodbath, these dynamics are critical. Everyone is facing challenges—attracting talent, retaining talent, managing resources. You can’t afford to have people on your team who don’t feel empowered to show up fully.

Michelle:

Absolutely.

Lesley:

If people don’t feel like they can be themselves, you’re leaving manpower, brainpower, and innovation on the table.

Coming from early tech, where it was all about, What do you know?, and then being dropped into this world of, Who do you know?, gave me the perspective to take a step back. Neither feels perfect, but the “who you know” culture can be toxic.

As a leader, you set the tone. If you’re not showing up authentically, your team won’t either. It’s hard because authenticity is often mistaken for over-familiarity, and it can blur boundaries with employees. But I’ve found that the risks are worth it.

If you’re modeling authenticity as a leader, people will mirror that. For me, that’s been one of my guiding principles as a manager.

Michelle:

I love that. Your diverse experiences bring such a valuable perspective. Everyone comes from a different place, but having someone like you, who has seen such a wide variety of dynamics, is incredible.

Michelle:

I think we sometimes get wrapped up in authenticity. I’ll share a story as an illustration.

When I was in college, I decided—for some reason—that when people asked me how I was, I’d answer honestly. Not just a casual good, but truly how I was feeling.

I distinctly remember passing an acquaintance on the steps of our student center. She said, Hey, how are you? and I just laid it all out.

Gillian:

Oh no.

Michelle:

She just said, Okay… see you, and walked away. Clearly, that’s not authenticity.

Gillian:

No, it’s not.

Michelle:

Can you give us a working definition of authenticity?

Lesley:

I was thinking about this in preparation for our conversation. Over the last 12 to 18 months, DEI and everything it represents has become somewhat taboo in corporate settings. We’re seeing a turn away from its importance.

I don’t want to define authenticity solely through that lens. People often assume that, as a Black gay woman, my authenticity is about carrying those identities as a flag and leading with that.

But I don’t think that’s the whole picture. I’m not naive—there are companies where you can’t fully show up authentically. Some companies don’t allow dreadlocks, require suits, or enforce rigid cultural norms.

For me, authenticity is about saying and doing the things that allow me to sleep well at night. It’s about not letting someone constantly talk over others in a meeting or avoiding last-minute criticism when I had earlier chances to weigh in.

Authenticity is broader than just my identity—it’s about how I show up and perform every aspect of my job to the best of my ability, with the tools and information I have.

While my culture, ethnicity, and sexuality inform how I define authenticity, they don’t solely define it.

Gillian:

I love that. Framing authenticity as how your actions affect others—and as something that helps you sleep at night—is such a thoughtful and empathetic perspective.

Lesley:

Yeah, and it's not easy. There are definitely nights where I think, I met that person with frustration and anger. Here's the thing—I'm doing this class right now called Positive Intelligence, and one of the lessons they teach is that everybody has a judge. You judge yourself, you judge others, and you judge the environment.

I’m naturally a judgmental person because it was a tool I learned very early on to survive as an outsider in a lot of different situations. My superpower at that time was being able to quickly size up a situation and determine how safe it was—that's judgment, right?

Now, I’m learning that judgment comes with negative emotions, whereas being discerning means parsing out information without the negativity. For example, if someone on my team isn’t performing, judgment is getting angry about it. But there’s no reason to get angry. It’s not about me. Instead, discernment is asking, Why do I think this is happening? What steps are necessary to move forward?

I can be discerning and forceful without the layer of judgment. I’ll be honest—I fail at this more than I get it right. But one of the key lessons from this program is to catch your judge and celebrate when you do.

The idea is that you’re going to keep judging, but you can recognize it: That’s your judge talking, not your voice. You can then shift to being discerning while still achieving what needs to be done.

From an interpersonal perspective, this approach has been transformative for me. I focus on removing the negative emotional component and sticking to fact-based insights and observations. Nothing is inherently good or bad—it just is.

This mindset has been especially helpful for me as a Type A person. It’s hard to understand non-Type A people sometimes. Early in my managerial career, I would think, Why don’t they want to work as hard as I do? But I realized that my goals aren’t everyone else’s goals.

As a manager, my job is to find out what their goals are, figure out how this job helps them achieve those goals, and remind them of that synergy. If the synergy isn’t there, I need the courage and the relationship to say, Maybe this isn’t the right space for you—not because you’re underperforming, but because it’s not aligned with your goals.

Those are hard conversations to have, but if you’ve been actively managing your team with their personal and professional goals in mind, it becomes an easier conversation.

Michelle:

What I heard from your intro is that you naturally show up with a posture of asking, What can I learn from this? How can I apply it broadly across my life? For someone who doesn’t naturally have that mindset, how can they start doing that kind of active management? How do we create safe—or as you might prefer, brave—spaces in the workplace?

Lesley:

First, let me say I prefer the term brave space over safe space. Safe spaces imply there’s no chance for people to be hurt or pushed. I’m not sure meaningful change can happen in truly safe spaces. Brave spaces, to me, are where people can say hard things—things others might not want to hear—knowing the intent isn’t malicious.

In groups or organizations, it’s crucial to define, discuss, and document rules of engagement. These should outline how we behave in meetings and what’s acceptable to the group. Having this as a collaborative conversation allows everyone to voice their perspective.

This buy-in is especially important for younger workers under 35. Bringing people along ensures that everyone is with you when you reach your goals.

For example, I know managers who always have the most junior person in the room start with feedback. If I, as the senior person, go first, others might just parrot what I say or feel intimidated to speak. Starting with younger or more junior folks gives them a chance to share and helps me see how they think.

It also lets them observe how others respond—how someone above them might answer, and how I might build on that. It’s a form of experiential learning.

Now, I know introverts find this kind of environment horrible. I’m still working on ways to create the same dynamic for people who don’t like speaking up. But this approach shifts the dynamic. Too often, senior leadership dominates the conversation.

Other managers might create office hours or drop-in times for one-on-one conversations to build relationships.

On a personal level, I’ve found it helpful to always ask why or how. People love talking about themselves, so it’s an easy way to engage them. I also make sure to prepare for meetings. With so much information available, there’s no excuse not to know something about the person you’re meeting—whether through LinkedIn, social media, or company materials.

When you show interest—How did you get here? What are your goals?—people open up. It’s that mirroring effect: if I share, they’re more likely to share.

When you have that connection—whether it’s over sports, food, or shared experiences—it’s much easier to have hard conversations. They see you as a person, just like them. Sometimes, that understanding is what’s missing.

And I have a lot of theories about why that connection is sometimes lost. When you look at the differences between female leaders and male leaders, I think female leadership tends to be more inclusive in an emotional way. If you consider the landscape of American business, part of the challenges we see might stem from the over-indexing of males in leadership positions.

Men are starting to understand this, but historically, women have often been pushed into the nurturer or caregiver role. I believe that's one of the most underrated skills for a business leader. In some of my past roles, I often felt more like a den mom than a financial executive, analytics guru, or marketing lead.

It was about managing my team—making sure this person who just broke up with their boyfriend is okay or helping someone struggling to learn a new analytics platform navigate their anxiety. There’s so much of that kind of emotional labor involved.

When I became a manager, I was surprised by how often I had to act as a therapist. People would come in and tell me things that had nothing to do with work. I quickly realized I needed to understand how to handle those conversations, too.

I’m a big believer in therapy. Just like going to the gym is essential for your body, therapy is critical for your mind and soul. With my therapist, half the time, we talk about my life, and the other half, we discuss work. After all, we spend the majority of our interpersonal time with people at work.

I spend eight hours a day with my colleagues. If I’m lucky, I get three hours with my daughter or maybe four and a half with my daughter and wife. There’s a significant psychological investment in the people we work with, so it’s crucial not to neglect that part of office culture.

If you do neglect it, you’ll see the consequences in turnover rates, unhappy employees, and people leaving. Studies show that happier employees consider that happiness a form of compensation. Today, more than ever, people are asking, Is this worth it? Many under-35s are saying no—they don’t want to spend their days with people they dislike.

Gillian:

I’m curious—when you’re interviewing for a role, how do you approach the decision? For instance, you have a highly qualified candidate who can get the job done versus someone you connect with personally but who might lack technical experience. What do you do? I’m actually in this situation right now.

Lesley:

If someone is smart and capable, I can probably teach them what they need to know to succeed in the job. What I can’t teach—or don’t have the time to teach—is how not to be an asshole, how to get along with others, or how to be additive to the team.

I prioritize hiring people who fit the culture and worry about the technical details later. For example, are they trained in Six Sigma? That can come later.

I’ve also been the beneficiary of people taking risks on me. When I switched from the dot-com world to production, which eventually led me to MTV Networks at Spike TV, I didn’t know the first thing about cable television. But leaders like Casey Patterson took a chance on me. They told me, You’re smart, you fit the culture, and we can teach you TV—it’s not that hard.

That kind of risk-taking made a difference in my career. Moving from New York to the Midwest in my forties, I noticed cultural differences. New York feels more like a culture-fit kind of place, where credentials matter less if you fit the vibe.

Chicago, on the other hand, feels more focused on what you know. Not having an MBA sometimes felt like a disadvantage here, whereas in New York, my track record and ability to fit into a team mattered more.

I think this difference might stem from the Midwest’s family-owned businesses, which often grow into corporations with their own cultures. Coastal areas, being innovation centers, tend to value diversity of thought more. But even there, it’s not perfect—VC funding for people of color or women is still below 2%.

Gillian:

I’d love to go back to the concept of a brave space. How can leaders contribute to creating a brave space, especially when it comes to empowering authenticity? And for those being led—the doers—what actionable insights can they take to foster these environments?

Lesley:

The first step is self-evaluation: How well do I really know my team? This goes beyond surface-level details like spouses’ names or whether they have kids or pets. It’s about understanding what makes them tick.

Many managers use tools like Myers-Briggs, which offer macro-level insights. But it’s essential to go deeper and ask yourself, Am I the kind of manager who thinks about these things? Or do I avoid them because they’re uncomfortable?

Gillian:

How does that work in your day-to-day? For instance, when you hire someone, you might learn a bit about them during the interview. Do you prioritize getting to know them right away, or does that happen over time? And during meetings, do you dedicate time for personal connection?

Lesley:

It’s a mix of both. Building that connection starts during onboarding but deepens over time. In meetings, I often spend the first few minutes connecting personally. It doesn’t have to be a formal thing—sometimes it’s just a quick chat before diving into the agenda.

Creating these moments of connection builds trust and helps establish the brave space where everyone feels empowered to be themselves and contribute fully.

Gillian:

And then additionally, when you're connecting with them in a meeting, are you spending 15 minutes? It's a 45-minute meeting. Are you spending 15 minutes kind of shooting the shit? I'm just curious.

Lesley:

Yeah, okay, so that granular. So, I always ask whenever I’m interviewing somebody—my last two questions are usually, "What are the best things and worst things that everyone you’ve worked with would say about you?" And then the final question I ask is, "How do you spend your time when you’re not at work?"

The way people choose to answer that question tells me so much about who they are and what motivates them. If someone says, "Oh, I don’t really do anything," I’ll be completely transparent—that’s a hard no for me. Like, if you can’t even express some curiosity or energy during an interview, you’re probably not going to thrive on my team.

I also make it a point to get to know people from day one. In one-on-ones with my team, I usually spend 15–20% of the time talking about personal stuff. It’s simple things like, "What did you do over the weekend?" or, "Have you planned your vacation?" I’m the vacation person, so I’ll ask, "Where do you want to go?" and share my own recommendations if I’ve been there.

I also love Reddit, and one of the women on my team is an avid cyclist. If I see something interesting, like a road trek in the Pyrenees, I’ll send her a link. It shows that I’m thinking about her interests, even outside of work. Those small moments build a connection.

Managers often forget what it was like to be a non-manager and how much it meant to feel recognized. Over time, these little gestures add up. They help create a sense of belonging and show your team you genuinely care.

On Fridays, I’ll start meetings by asking, "What plans do you have for the weekend?" I’m also an oversharer—I’ll tell them about my own weekend plans, like going to Las Vegas to see live music at The Sphere. It’s important for them to see that I’m a whole person, just like they are.

Sometimes, I’ll have to deliver hard feedback or make tough calls, but these personal touches make those moments easier to navigate. It’s about reciprocity—sharing, being curious, and setting the tone for authenticity.

Not everyone is comfortable with this level of openness, and that’s okay. If someone doesn’t want to engage on certain topics, like their identity or personal life, you respect that boundary. But there’s always something to connect on—food, music, sports, travel.

As a manager, it’s your responsibility to create this culture. For employees, you can replicate this approach with your peers. Be curious, build connections, and foster collaboration.

If you’re an employee and want to connect with your manager or even their boss, consider asking for a 30-minute meeting to learn about their career path. It’s scary at first, but most people love talking about themselves. You’d be surprised at how these conversations can spark change or build rapport.

Michelle:

What’s something someone could walk away from this conversation and take action on in the next five minutes? What’s a step they can take right now?

Gillian:

And then additionally, like, when you're connecting with them in a meeting, are you spending 15 minutes? It’s a 45-minute meeting. Are you spending 15 minutes kind of shooting the shit? I’m just curious.

Lesley:

Yeah, okay, so that granular. So, I always ask whenever I’m interviewing somebody—my last two questions are usually, "What are the best things and worst things that everyone you’ve worked with would say about you?" And then the final question I ask is, "How do you spend your time when you’re not at work?"

The way people choose to answer that question tells me so much about who they are and what motivates them. If someone says, "Oh, I don’t really do anything," I’ll be completely transparent—that’s a hard no for me. Like, if you can’t even express some curiosity or energy during an interview, you’re probably not going to thrive on my team.

I also make it a point to get to know people from day one. In one-on-ones with my team, I usually spend 15–20% of the time talking about personal stuff. It’s simple things like, "What did you do over the weekend?" or, "Have you planned your vacation?" I’m the vacation person, so I’ll ask, "Where do you want to go?" and share my own recommendations if I’ve been there.

I also love Reddit, and one of the women on my team is an avid cyclist. If I see something interesting, like a road trek in the Pyrenees, I’ll send her a link. It shows that I’m thinking about her interests, even outside of work. Those small moments build a connection.

Managers often forget what it was like to be a non-manager and how much it meant to feel recognized. Over time, these little gestures add up. They help create a sense of belonging and show your team you genuinely care.

On Fridays, I’ll start meetings by asking, "What plans do you have for the weekend?" I’m also an oversharer—I’ll tell them about my own weekend plans, like going to Las Vegas to see live music at The Sphere. It’s important for them to see that I’m a whole person, just like they are.

Sometimes, I’ll have to deliver hard feedback or make tough calls, but these personal touches make those moments easier to navigate. It’s about reciprocity—sharing, being curious, and setting the tone for authenticity.

Not everyone is comfortable with this level of openness, and that’s okay. If someone doesn’t want to engage on certain topics, like their identity or personal life, you respect that boundary. But there’s always something to connect on—food, music, sports, travel.

As a manager, it’s your responsibility to create this culture. For employees, you can replicate this approach with your peers. Be curious, build connections, and foster collaboration.

If you’re an employee and want to connect with your manager or even their boss, consider asking for a 30-minute meeting to learn about their career path. It’s scary at first, but most people love talking about themselves. You’d be surprised at how these conversations can spark change or build rapport.

Michelle:

What’s something someone could walk away from this conversation and take action on in the next five minutes? What’s a step they can take right now?

Lesley:

I would say, find someone in your office that you’ve never spoken to and start a conversation with them, or make the intention to do it. Reach out, put time on their calendar, because a lot of people aren’t in offices. But I think that would be where I would start.

There are a lot of people in marketing who wish they were in strategy, or in strategy wishing they were in HR, or in HR wishing they were in legal. Just that curiosity alone—find someone in the legal department and say, "I’m in HR. I have no idea what you guys do. What does your day look like? I’m curious." It’s a really easy conversation.

If you’re not comfortable speaking up all the time, the observation piece is still important. Maybe it’s an email after a meeting or reaching out to someone who’s your extrovert buddy. You could say, "I didn’t want to say anything in the meeting, but did you notice so-and-so was talking over so-and-so? How did you feel about that?"

Then let that extrovert be your amplifier. That’s why we’re here—to support our introverted friends. There are ways to navigate that, but observation and small conversations are great places to start.

Gillian:

It’s almost made me miss the physical side of being in an office, more than I realized. I didn’t think I longed for it. I’m curious—do you have any off-the-cuff tips on how to truly get to know people? How have you changed how you approach this in a remote world?

Lesley:

I got hired at Intel remotely during the pandemic. I think it was seven months before I met my boss in person, and maybe 18 months before I met anyone on my team in person. It is definitely harder. While I love working remotely, it’s made that aspect of the job more challenging.

I haven’t quite figured out how to replicate the watercooler conversations or hallway passing, but I try to treat virtual meetings as I would in-person ones. For example, Zoom gives us a window into people’s homes, which is such a gift for understanding who they are.

I’ll comment on something in their background, like, "Is that a Tiny Coach book on your shelf?" It’s a simple way to connect.

If you’re geographically close, and you have the budget, try to get people together in real life. While Zoom happy hours and trivia games can bridge the gap, nothing replaces in-person interactions.

Many magical moments in my career happened in a conference room with a whiteboard and real-time collaboration. It’s hard to replicate that. I understand the return-to-office discussions because it’s difficult to recreate that dynamic remotely.

Hopefully, tools will improve to better replicate those experiences. I’m curious to see if this remote phase has impacted innovation. My bet is that it has, but we’ll need data to confirm it.

Gillian:

I started my career at an old-school ad agency, and so many great ideas came from casual interactions—someone kicking back at their desk, tossing around thoughts, and suddenly landing on the big idea. It’s hard to replicate that now.

Lesley:

Exactly. Or someone walking by your screen and saying, "Why don’t you try it this way?" So many of those organic moments are hard to recreate remotely.

Gillian:

For my team, Figma has been a game-changer. You can work together in real-time, have a dialog while building creative or product screens, and it feels collaborative.

Michelle:

We’re not sponsored, but we could be.

Lesley:

Exactly. Tool adoption is key, but it can be infuriating. Even if a tool like Figma is great, getting everyone to use it effectively is another challenge altogether.

Gillian:

We’ve been trying to transition our sales team off PowerPoint. It’s been a slow process, but we’re making progress with Figma slides. PowerPoint just doesn’t cut it visually.

Lesley:

I can imagine. It’s hard, but it’s worth it.

Gillian:

This has been amazing, Lesley. Your insights into management and creating authentic connections are so actionable and inspiring. It’s not a skill we’re all born with, but it’s part of growth.

Lesley:

Absolutely. You don’t always have to lead; sometimes you just need to be the catalyst. It all starts with asking the right questions.

Gillian:

Lesley, thank you so much for your time. And to everyone listening, thank you for tuning in to Future Works. Please subscribe and follow along as we continue these conversations.

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