Work Besties Who Podcast

The Power of Work Bestie Culture: 5 Leadership Practices That Build Trust & Joy at Work

• Work Besties Who Podcast • Season 2 • Episode 73

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Ruby Vesely is the kind of leader you wish you had—and the one you can start becoming today.
In this conversation with Jess and Claude, Ruby—executive coach, HR strategist, and co-author of You, Me, We—shares how to build workplaces where people feel seen, safe, and supported.

She walks us through:

  • The 10-second “What’s your number today?” check-in that transforms team culture
  • The 5 practices of being an ally at work (generosity, compassion, vulnerability, candor, accountability)
  • Why presence—not perfection—is the real leadership superpower
  • How to model boundaries and self-care so your team believes you
  • What it means to be your own work bestie

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Work Besties! Theme Song Written by Ralph Lentini @therallyband

Ruby Vesley:

Ask each other what's your number today. We don't have to explain it. It's a quick uh check-in so we know how to show up for each other differently.

Claude:

Hi, I'm Clun and I'm Jess. We are corporate employees by day, entrepreneurs by night, and work besties for life.

Jess:

Join us as we explore how work besties lift each other up, laugh through the chaos, and thrive together in every industry. Work besties! When we interviewed Marag Bear back in episode 46, we knew right away we had to talk to work besties. We are so excited to have Ruby, who's an executive coach, HR strategist, keynote speaker, and the co-author of You Me We, a book that puts words to something we've always believed. Work is better when you have a friend by your side.

Claude:

But she doesn't stop there. Ruby helps people lead with compassion, create cultures that feel good and show up fully, whether you're the CEO or a new hire.

Jess:

Stay with us to the end. Ruby shares one surprisingly simple shift that anyone can make to create more connection, joy, and trust at work, even if you're not in a leadership role. Ruby, welcome.

Ruby Vesley:

Thank you. I'm super psyched to be here with you.

Jess:

Let's start with something that's very close to our hearts. What does the phrase work bestie mean to you?

Ruby Vesley:

The word that comes just right out of my soul is joy. Someone who brings joy that would be on your joy list. And if you were to make a list of all the things that bring you joy, I would say work bestie is one of those things. I definitely think about it with Morag, with Eric, with Jose, who's also on our team. I wake up every morning and there's some days I don't want to go to work, but I actually get up not only because you know I need to get made and for my clients, but I get up for them. Right. And also in service of their families and our collective success. So it's it's thinking beyond ourselves and considering those that are our besties, right? And how do we make lives better for all of us?

Claude:

Yeah. It is so true because when that is really the real teamwork, right? You do for your team, even if you don't want to do it, but you will do it because you don't want your team or your work bestie to let them down.

Jess:

So I I know your ethos and and the element of how having meaningful relationships at work is so helpful. What shaped your career or got you to be in service of this focus?

Ruby Vesley:

You know, it's it's organic, right? I I took this um cerveyed in an early job, and the number one thing that came out in the survey was the gift of helps, H E L P S, which was really the gift of service. And that really landed for me. And the goal, even to this day, is how can I help make your life lighter in the work that we do, or how can I support your teens' lives to be lighter, that joyful, that work besties. But I kind of came up through the leadership development channel, and I had amazing people in my world. And and one of the practices, actually, of our book of being an ally to other people is about connection and compassion. It was my early teens, and my dad had cancer, and within six months of his diagnosis, he passed away. And it was early in my career. And my HR team showed up for me on this human level, and I was still held accountable for the things I needed to get done, but I was able to really take care of my family and be in service of my dad and spend time with him and still do the work. And it just taught me a lot about how we show up for each other at work, even in those difficult times. And it got in my bones a little bit in how people feel in our presence and how they feel. Do they feel loved on? Do they feel valued? Do they feel seen? It changes the nature of what it feels like at work. Um, that seed was planted even before that, but really cemented in my early 20s when all those people just showed up for me in such a brilliant way in that really difficult time. It taught me a lot about what kind of leader I wanted to be.

Claude:

For HR event to show up that way. And I think it's a great example of what should be.

Ruby Vesley:

And even in that story, I talk about how everyone showed up for the funeral, just showing up in life and giving people time to navigate those sacred moments that are occurring, the good stuff and the hard stuff. It just changes the way it feels and it changes relationships.

Jess:

And feeling feeling the valued and scene, as you commented about. You were part of the co-authorship of the You, Me, and We with Morag, who we love. And Eric, who we'll have to get next on this podcast. We gotta get the trifecta. For those that are viewing that um are listening. Ruby is showing the book You, Me, Weave, that she co-authored with Eric and Mrag. So, what inspired the three of you to write this book together?

Ruby Vesley:

Morag's first book, uh, Cultivate the Power of Winning Relationships at Work. The second edition actually just came out and she did the audio, and it's her beautiful British voice. It's amazing, so you should check that out.

Jess:

Um, her voice is so soothing too.

Ruby Vesley:

That book is really about what are your critical goals, the things you're trying to accomplish in your personal life at work, um, and who are the critical stakeholders and what is the quality and depth of those relationships. And then it's getting to think about what actions do I want to take or how do I want to show up to shift this relationship. We may not become allies, but how do I move them more towards an ally relationship based on my actions? So the second book is it's more our collective thinking now, too. Morag wrote that book, the first book, right when I joined her years ago, I was one of the readers of that early book. Um, and then I started working for her. And we've been teaching these models, right? The cultivate models, the relationship ecosystem, and starting to bring in our own stories and our own experiences of friends at work based and also just working with our clients. And so this book um is more on how do you show up? What are the there's five practices in there? How do I show up as a friend to others at work? What are those baby steps that I can take and to start building stronger relationships? And we actually wrote it during COVID. So we had a little bit of that lens too, when we were more disconnected and we were we were mostly remote initially, and then moving into this hybrid lane, which a lot of companies are still fully remote now and hybrid. So it has some of that nuance in it as well. And what are the five and there's five practices, and they're both kind of double barreled. The first one is abundance and generosity. To show up as a friend at work to others, it's about sharing resources, sharing time, creating space so you can actually learn about the other person. And it's it's all about that generosity and abundance. And that's one of the things I always tell Maura, that's like her strongest quality. She's always been super abundant in generosity. And even in writing this book, she wanted Eric and I to bring our voices forward as well. That's just like what's written in her. Um, and then connection and compassion is the second one. This is knowing the people around you, knowing their story beyond the work, operating in a way that people do see, seen, valued, her, and then just compassion, which is pure empathy, just being present with people, some of those things we're already talked about. The third one's courage and vulnerability. This is being um trusting someone enough or being courageous enough to ask for help. My edge is actually receiving help, trusting someone to say, I have no idea what the hell I'm doing. Will you please help me? Or I've backed myself in a corner. I'm screwed. Will you please support me in this? So there's a little bit of vulnerability of showing what's inside. So you have abundance and generosity, connection, compassion, courage and vulnerability. The fourth one is candor and debate. This is the having the hard conversations, being willing to say the thing that you're thinking, feeling safe enough to do that. You can see how they start to build, right? We have to spend time with people, feel safe and connected so that we can start to be vulnerable. And then now we can really do the work and dig in and really create, if if you're thinking about in the business environment, creating a product that is beyond everyone's imaginations, right? If you had done the work on your own. But we've got to be able to talk about the hard things and have the hard conversations. And the last one's action and accountability. So that's keeping your word, that's doing what you say you're going to do. Um then when we think of the way we sort of define accountability is sort of looking up from your own life and your own work and proactively thinking about what others might need. This one reminds me of service-based leadership a little bit. Um, so those are the five practices.

Claude:

I just love those because it's really good relationship. Any relationship. Yeah, it's just as it's a work, it's really, you know, I I just love it. It goes from very big and then it goes, and then you have this unit of this friendship because you put all together. I think it's great.

Ruby Vesley:

Well, I love that you said that too, because you can also look at it, and we have the ally mindset profiles. I'll share the link with that for you, and it's free for anybody. And it asks you a series of questions, and you'll get a report that shows what are your strongest scoring areas? What are those things that come more naturally? What are those things that take more energy and intentionality? Like for me, connection and compassion. I don't even have to think about it. Candor and debate. I have to really think about it. I have to build up my courage and I have to feel safe and I have to, it's more risky for me. So it's it's a it's a beautiful model, like you said, right? Thinking about just each of the pieces and how am I showing up in this relationship and which one might I really lean into in this particular frame to make it different.

Jess:

Knowing the group of individuals you're working with, where you think they're at, too, right? Because to your point, you might have the concern about getting to the candor and debate, but they might not even be ready for the connection.

Ruby Vesley:

Right. Yeah, such a good point.

Jess:

So I I know you guys have worked with so many different leaders and different types of companies and organization. From your perspective, what really separates out those good leaders from the great ones?

Ruby Vesley:

There are two things that I really care deeply about that if I'm leading a team or working with someone that you'll hear me talk about it, it just comes out of my mouth. So, one deep presence, it's a it's a phrase I think about a lot, is really being in this moment with the human in front of you. Especially if you are on camera. I mean, we we do it in person, I think we're better about it, but I still have been an in-person, I've led in-tech teams recently, high levels where everyone is doing something else on their retreat. And it makes me like burn inside.

Jess:

I'm like, if this was the one thing on the retreat, not just like I'm thinking of routine meetings, and there's so many people are like, Can you answer that question? You're like, Yeah, because you're not paying attention. I know.

Ruby Vesley:

Yes, yeah, and I feel like it's actually micro cuts in relationships. We are not witnessing someone when they're speaking, our human nature, like we can't handle it. I think there's something we get into fight or flight, actually. We're actively making that relationship worse if we are not present. Period. And so that's one. That's you can see I get really passionate about it. That's my first one.

Claude:

But before you go to the other one, you actually make them present. Do you just call them out?

Ruby Vesley:

We do. I actually can think of one team that we were working with a few months ago. Um, my colleague Eric, he got in this coaching mindset where you can practice courage, right, and speak truth. And then they get without attachment, right? And they get to decide what they want to do with it. But they got it, and they shut everything down. And that leader reached out to us like a few weeks later, and he's like, It was actually longer than that. He's like, everything has changed. And they're keeping their commitments and they're being it's changed the way that they talk to one another. It's it's so important.

Jess:

I'm sure because it's known when you attend this particular meeting now, you do not come in with the mindset of you're multitasking. Maybe use your computer to look up something, but not uh yeah, and be explicit about what you're doing.

Ruby Vesley:

And as they were very high leaders in the organization, and one of them committed to, hey, I'm going to show up in this one very public meeting, I'm committing to you that I will do nothing else. And so now they're thinking about, well, how does my presence ripple out into the rest of the organization? So if I'm showing up present with my team, they know that that's expected.

Jess:

Right. Exactly.

Ruby Vesley:

Because there are people are always watching us as leaders, they're always watching us, every little thing that we do.

Jess:

Totally. And why would they do something you say to do if you're not doing? Of course. It sounds simple, but it's true. Well, it's like being a parent.

Claude:

There's a knock of some matter.

Ruby Vesley:

And the second one is as leaders, we have to practice self-care. We have to take care of ourselves. And I think I care so much about this one just because I think it's my edge as well. Like the slowing down, taking care of myself, holding boundaries, all those things, having the tough conversations, speaking up. Like that's we have to do it. And when we take care of ourselves and model it for other people, we show up differently in the world. Like, think about when you're rested and you've really taken care of yourself, or you've exercised all week and you're going out for the evening and you feel alive, like that aliveness it impacts the people around you. That light goes beyond you.

Claude:

Yeah, totally. I remember actually there was one person on my team, and it was during a stress full time. And one day she, and I guess I was stressed. And one day she turned around and she's like, Are you okay? You're not the same. And that actually, and I appreciated that because at least it snapped me out of it. I'm like, Oh, okay, I need to be careful. I'm not showing up like I should be. My team sees it, and I I think that is so important, like you say, like self-care and realizing when to stop.

Ruby Vesley:

Yeah, yeah. It's authenticity too, right? Taking care of yourself and showing who you are and all of those things.

Jess:

Yeah. And I I've been encouraging my team, and actually they now say it, they're like, Oh, I blocked that out for this. I actually tell them, block it out on your calendar. Like, even if it's during the day, I'd rather you disappear for an hour to go do an exercise class or to, you know, whatever errands you need to do that will help you calm down. Have you need to go see a therapist, whatever it is, just to encourage that they do take that time for themselves. And I I'm honest with them too. Like, here are the two nights that I'm definitely have to leave by so-and-so time so I can be with my daughter. And I think it helps people feel more comfortable too, and you as a leader say you're doing it.

Ruby Vesley:

So and you practice it.

Jess:

Yeah.

Ruby Vesley:

Right. I mean, I have leaders who are like, don't work at night and turn off your computer, and they're sending emails at midnight or 8:30, and then and then the other people don't have boundaries, right? And it's it's going off on their phone or on their watch. And so then they're responding. So it's thinking about how we model it. And um, there's something we always say, you've probably heard this before, but and a leader brings the weather. How we walk into a room and how we feel, and people can feel it when we're faking it, they just can't.

Jess:

Most companies kind of use the belonging as a buzzword. How do you help companies move past that? What are some ways if today that company isn't showcasing belonging, that you can help them infuse that in there?

Ruby Vesley:

If you think about the model, even being an ally to others, it's abundance and generosity. I would always call that a starting place, which is making space for something other than work. Right. So there's a little spaciousness in there, or to your point, Jess, the um, hey, if you need to go take care of yourself, like letting people know it's okay to do that, but creating space for people to be together, either virtually and deeply present together. I think is the do people feel like you see them? Do people know that you care about them? Do you do little things that aren't expected to um let people know you're thinking about them? And and it really is, I would say, even just being present with someone and having a conversation and being curious about their life without judgment is amazing. You can see people light up when you start to ask them about whatever they care about, right? Like their DD group, right? Or their wedding they went to last Saturday, or pictures of the kids on their desks, or just sharing little pieces of who we are. We don't have to know everything, but creating space and time to know the human is the number one thing.

Jess:

Before we start recording, you'd made a comment about how you can be a best friend for yourself. What is what does that mean to you?

Ruby Vesley:

I love that you asked that question. Thank you. Very passionate about that. Um, when we wrote this book and we started thinking about, well, how do I show up in the world for others? We very quickly realized that there's actually a whole nother conversation that's equally weighted of how do I actually show up for myself so that I have the energy and the capacity and the aliveness and the willingness to actually invest in other relationships. As I think about this model, it's the same model, but it's focused on self-care. So the first one abundance and generosity. Do you create space and time for yourself? Do you practice lavish self-care? Some people, my buddy Eric's never gonna practice lavish self-care. I'm like, that's fine, but can you move it a centimeter over? So it starts with space and time for ourselves, which is the one thing that a lot of us cut when we have all these things going off and on in our personal and our professional lives, it's the easiest thing to cut because we can control it. The second one's connection and compassion. It's really checking in. What am I feeling right now? How has this week been? What's working? What's not? If we just keep living our lives above the fray and we don't check in, we are probably living a life that's unintentional. We've got to create space and time to connect with what are my values right now? What do I care about? What's most important? What needs to go? Because if we don't, we're keeping commitments that maybe aren't aligned with our values and what we care about. Maybe we're in a marriage that's not great, that we haven't dealt with for 10 years, right? If we don't slow down, if we don't take the time and connect and be compassionate with ourselves, it's it's hard to live the life we're longing for. The next one's courage and vulnerability. This is it's being willing to show a little bit of what's inside, letting the light show, let the cracks show a little bit. And the vulnerability for me is in taking risks that are based on what you care about, your values and your legacy and the life you're longing for. It's it's not ever easy to take big risks, but it is a little bit lighter if you know why the hell you're doing it and the stake in the ground, right? And why it's important to you versus doing something that's really scary and you don't even want to do it in the first place. And then the fourth one is candor and debate, which is kind of funny with yourself, right? It's like, why are we doing this? I don't know. You're telling me. Oh yeah, I don't know. It's sort of like, why am I doing this thing? Do I have to do this thing? Why am I making these stupid muffins for this thing that I don't really give a crap about anymore? You know, those sort of things, really assessing the situation and what stories am I telling myself? Either imposter syndrome or what stories am I making up about other people in my lives? Is that true? It's this questioning and willing to do things differently in some way. And then the last one's action and accountability, and that's keeping your word to yourself. But you can see how they all kind of start with abundance and generosity, which is space and time.

Claude:

And the result will give you the being the time to take care of yourself, right? The muffins or whatever. If I don't do that, then I have time to do whatever I love doing.

Ruby Vesley:

And they're all connected. And when we know what we care about, when we know who we are, when we're listening to an inside voice, in psychology, they call it the capital S self. In coaching, we call it the leader within or the wise one inside. When we're connected to that and showing up in the world as leaders, it's a way different experience, not only inside, but for the people who are watching us and dealing with us.

Jess:

It's like the putting your own oxygen mask on first. You need to take care of yourself before you really can, in a social wellness way, take care of others. Looking at yourself in the mirror as you're doing all of these things.

Ruby Vesley:

Totally. What am I experiencing and what do I need and what's different today? And even just taking stock for five minutes before you jump on a Zoom call, right? Just taking that moment to get everything out of your brain, putting everything aside, taking some deep breaths. Like you've you've even just tuned in inside, which is going to be very different than hanging up the phone and frantically going to the next one or running to the bathroom, or like it's um it just changes what it feels like. And and you know what? There's we can only do our best. We do this other activity, we do it in some of our workshops and our keynotes, and we'll say, okay, tell me your number one to 10. So maybe you could tell me if you're you're willing to do it. One is, and you can do it with your hands if you want. One is I have nothing today. I didn't even want to get out of bed, and I am and 10 is like, I'm cubing it. I feel so good and I'm alive and amazing. So, what's your number today, do you think? Just like a gut check-in.

Jess:

Listen, and Claude's face pretty much tells it all. Um, I'm gonna go first because I actually took the day off. And I actually got to get in a long run, so it was a 10 for me today. I woke up super jazzed, and there's a TV show that my daughter loves. We did the dance routine this morning, and even she was like, Well, this is the happiest I've seen you in forever.

Claude:

So I would say I'm a five or six.

Ruby Vesley:

Yeah.

Claude:

Yeah, it was a semi-friday and I worked.

Ruby Vesley:

I'll do it too. Vulnerability. I would say I am probably uh seven or eight.

Jess:

Okay, that's good. That's yeah.

Ruby Vesley:

I went to yoga and uh and I meditated this morning, but I did these things in anticip in anticipation of spending time with you. So I was preparing my brain, and I knew that if I worked until the moment I got on this call, that I wouldn't be able to really be present and I might show up a little faky, and I didn't want to do that. Oh it's so it's paying attention, like getting ready for what's coming.

Jess:

Yeah.

Ruby Vesley:

And and also where am I at right now? And whatever your number is, that's your best. If you're a two this morning and you go to bed at night and you can reflect and say, okay, at a two, did I do my best? You're good. And you and you move on. So it's like giving yourself a little bit of grace as well. Um, this is actually an activity connecting it back to building connection on your team. This is something we do with with our team. We'll ask each other, what's your number today? We don't have to explain it. It's a quick uh check-in so we know how to show up for each other differently. If I know it's a three for you, I'm gonna ask the thing that I need today.

Claude:

I love that that part because, for example, I say to my team, what number are you? And they'll be a three. Do I then answer back, is there anything that can help you to elevate that number?

Ruby Vesley:

You have to use your eyes and your ears and your intuition and in that situation and sort of feel it out, depending on what you're trying to accomplish as well. My gut is that everyone gets to be, and we get to be okay with not having a good day. And then if there's a work-related, like, hey, I know today may not be feeling the greatest. Is there anything that you need? So it's I would say there's no really hard and fast rule. Definitely making it okay to be whatever number you are. So I'll give you an example of how we use this really quickly. We had an off-site strategy meeting, and we're not usually all in the same place at the same time, it's very rare. And we got together, and Eric will tell you that he really struggles with depression and anxiety. And so he will wake up sometimes and not even know what's gonna be there. And we had this time set aside, and he came to our meeting and he was kind of had his head in his hands, and we're doing like high-level strategy planning, intents where you need your whole faculty to really even be into it. Uh, and he, and so Morag, brilliant, she was like, Eric, what's your number? And I think he said he was a one, and he kind of put his head in his hands, and I'm like, There's no way we can do this. We can't force him to do this. We were actually at his house, and Morag's like, go take a nap. And Morag and I were able to adjust. We moved everything around and we did our work. He woke up like 45 minutes later. He was a two or three, but we honored his experience. We allowed him to choose if he wanted to come back. It's a very different thing than doing things we have to do. We tell ourselves we have to do things this way all the time, and we don't. So giving people a little bit of grace in that way.

Claude:

It's an incredible way for a leader to actually say to someone, it's okay. And it shows this empathy that is so incredible that at the end will make everybody work for you, do even more because they trust you, they allowed you to be a one.

Jess:

Helping yourself as a work capacity for yourself. If I come in as a one, no one's gonna change me as a one. Even if you don't have empathy for me or not, I have to be able to stand my ground and say I cannot do it today. And I think that's also a powerful message, too. This has been so lovely. I feel like we've learned so much. We have one final reflection to share with us one surprisingly simple shift that anyone can make to create more connection, joy, and trust at work, even if you're not in a leadership role.

Ruby Vesley:

Um, one of the things that is really powerful is when we reach out to someone just to check on them when we don't need something. It doesn't have to be for 10 minutes, it can be a quick slack or a text or to let them know that you're thinking about them outside of the work frame. It's a way to build trust. You have to be careful though, because the first time you do it, everyone's gonna be like, Why are they calling me on a phone? And then self-care. When do you gotta turn off your phone? You've gotta turn off your laptop, and you've gotta really be present. Really, all that others need from you is being being present. I like it.

Claude:

Thank you, Ruby. This conversation was like exactly what we needed. It's a reminder that connection is a strategy, but not a set effect, and it's also something that has to come naturally. If this resonated, share it with your team or your work bestie. Yes. Ruby, tell us how everyone can reach you.

Ruby Vesley:

You can have me on LinkedIn and more aggregate as well. Um, our website is skyteam.com and it's spelled SK Team, like the Isle of Sky. Thank you, Scooby. Thank you for having me.

Jess:

Remember, whether you're swapping snacks in the break room, rescuing each other from endless meetings, or just sending that perfectly timed meme. Having a work bestie is like having your own personal hype squad.

Claude:

So keep lifting each other up, laughing through the chaos, and of course, thriving. Until next time, stay positive, stay productive, and don't forget to keep supporting each other.

Jess:

Work besties!

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Claude F

Co-host
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Jess K

Co-host
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Ruby Vesely

Guest