Meredith Farley

On Content People, host Meredith Farley interviews creative professionals and leaders to get a behind-the-scenes look at their career experiences and turn that into actionable advice for listeners. Tune in to hear from experts in various media, and get inspired to find contentment in your own creative career.

Episode #7 Summary

In this chat with Meredith, Brianna de L’airre, a senior manager of Wayfair’s coaching enablement team, discusses everything from radical candor to the importance of embracing growing pains.

In the seventh episode of Content People, I had the pleasure of talking to Brianna de L’airre.

Brianna is a senior manager of the coaching enablement team in Wayfair’s Business to Business department. Although she has a background in education, she says teaching and coaching are two different things. In fact, she tells me the latter is more about encouraging self-discovery in the folks you’re coaching (as opposed to just imparting your own wisdom).

“You have to care, but you have to challenge,” she says — and that gets us talking about radical candor. That’s what Brianna calls “caring implicitly,” and it’s an important part of her coaching philosophy. It’s also an important part of being a manager, worker or creator in today’s world. 

Here are a few more things we discuss:

  • Why growing pains are actually your friend.
  • What it means to be a good coach.
  • Why the best salespeople are also the best listeners.
  • The importance of asking for feedback.
  • Balancing the different parts of your identity.
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After a chat like this, you’re sure to come away feeling inspired and empowered. I know I did.

Thanks for listening!

– Meredith Farley, Creator and Host of Content People

More Content for Content People

Meet Brianna: Visit Brianna on LinkedIn and feel free to share your favorite resources on coaching, sales behaviors and developing teams.

Radical Candor: Check out the book that inspires Brianna’s approach to caring implicitly.

Brafton: Do a little self-discovery of your own and learn something new with our digital marketing newsletter

Meredith’s newsletter: Click here to check out Meredith’s newsletter (also called Content People).

Podcast Transcript:

Meredith Farley: Hello, and welcome to Content People, a podcast where we talk to creative professionals and leaders to get a behind-the-scenes look at their career experiences, and we try to turn that into actionable advice for you, our listeners.

Tune in to hear from experts in various media and get inspired to find contentment in your own career. I’m your host, Meredith Farley. As some of you know, I used to be the COO at Brafton where I oversaw creative project management and consulting teams. I’m no longer with the company, but Brafton is still producing this podcast, so thanks Brafton.

We recorded this episode a while ago, I think actually it might have been back in the summer, so you will probably hear me make mention of my former role. If you want to keep up with what I’m doing now, you can check me out on LinkedIn and subscribe to my newsletter. Also call Content People, which we’ll link to in the show notes.

Give it a shot. It’s a once a week send where I share thoughts and actionable advice based on nearly 15 years of creative leadership. You can also listen, rate, and subscribe to Content People wherever you get your podcasts. Today, I’m here alongside Ian Servin, Creative Director of Video at Brafton and Producer of this show. Hey, Ian.

Ian Servin: Hey, Meredith.

Meredith Farley: On today’s episode, we talked with Brianna de L’aire, a coaching enablement manager at Wayfair, and we get into the weeds about sales coaching. Yeah.

Ian Servin: This was a really interesting conversation. As someone who’s a manager, who cares about learning about leadership, I’ve known a little bit about sales coaching and some of the sort of principles behind it, but I’ve actually never met or talked to someone that actually did it. As a manager, it is so cool to hear from someone whose main job, primary focus, it really is to motivate people and help them overcome obstacles and ultimately find success at work. She had a lot of really great insight to share with us.

Meredith Farley: Definitely. I mentioned this in the show, but Brianna is actually also a really good personal friend of mine. She’s really fun, also kind of funny to have a more structured formal combo with her and explore what she’s learned as a sales coach. Brianna is just such a savvy lady. Brianna, I love you, and thank you for doing this episode. With all that said, we’ll throw it over to our conversation with Brianna now.

Hey, Brianna, welcome to Content People.

Brianna de L’airre: Hi, Meredith. Thank you for inviting me.

Meredith Farley: I’m very happy you came. I’ll just start off by saying that this is a slightly different podcast and that I’ve had the chance to talk to lots of people who are super interesting, but who I don’t know very well. You are one of my best friends, so we’re going to play professional people on this podcast and talk about work, but some context for the listeners, I suppose, but maybe you could start off by telling us who you are, what you do out, Wayfair, and talk a little bit about the really cool content-related job that you have.

Brianna de L’airre: Yeah, yeah, and thank you again. Thank you so much for having me on the podcast. It’s so exciting to see your friends when they’re out there doing something so cool, and it’s just so awesome to be a part of that, and so I’m really grateful to be here. My name is Brianna de L’aire. I work at Wayfair in our B2B department, Business to Business, and my current role is I’m a senior manager of the coaching enablement team. What we do is enable our frontline coaches with coaching content and optimized tools for coaches so that they can go out there, concentrate on supporting sales behaviors, getting the best of their teams, and focus less on whether or not their tools are working and more on what’s really important, which is just person-to-person connection.

Meredith Farley: Okay, thank you. You have such an interesting job. I’m so excited to dig into it with you. One thing maybe I would start with, which I feel like is one of my first questions when you first told me about your role is, can you explain the B2B side of Wayfair to folks because I always think of Wayfair B2C, and I was like, who are you selling to? What is this team?

Brianna de L’airre: Yeah, yeah, B2B is fabulous. So the majority of Wayfair, of course, is our B2C selling direct to customer, but do you have a branch of Wayfair where we sell direct to businesses? So someone might say, well, what’s on Wayfair that supports businesses? We offer such a variety of products that work really well with specific verticals. So we’re selling to contractors, interior designers, we’re selling to office spaces, all the way from mom and pop shops who are looking to establish themselves and start a new storefront all the way up to hotel chains and property developers.

Meredith Farley: Very important question. Can you confirm or deny that the entire set of 365 days was all Wayfair items? Yes or no? Are you allowed to say?

Brianna de L’airre: I can neither confirm nor deny. But I will say that you might have allegedly pointed out that some of those items were very similar to what’s available on the Wayfair website. I don’t know who manages their set design, but they have a bold taste for sure.

Meredith Farley: Well, I suppose it wasn’t the real focus, but all right, interesting. So what is the average day in the life of Brianna at work?

Brianna de L’airre: I don’t think there is a singular average day. It really depends on what we’re working on. And so I would say the one consistent element throughout my days is that I am connecting with a lot of different people. I connect with my team daily, so I have a tiny but mighty team of two content developers. We wear a lot of different hats on the team, but I make sure to have a connection point with them where we go over everything from what they have planned for the day to what they had done the previous night and have a really loose connection that is fun and friendly, but professionally driven.

And then throughout the day, I’m staying connected with our stakeholders, connecting with sales program leaders, connecting with frontline reps, connecting with our operations team and our tools team and all of that good stuff. And so I find myself often in a project manager role where I’m the connective tissue between our centralized operations team and our sales teams. And so really aligning with everyone to make sure we have our key objectives in mind and moving projects forward.

Meredith Farley: I love the description of you as connective tissue.

Brianna de L’airre: Sure. Like a tendon, yeah, exactly.

Meredith Farley: So I want to come back to how much you talk to your team and how you cultivate a team environment in this remote world, but I’m really curious about what type of content your team is creating and how are you deciding what to create?

Brianna de L’airre: Yeah, that’s a great question. So a big focus on the training and coaching team, which is the team that I’m under in B2B training and coaching. We focus predominantly on creating content that helps our coaches selling behaviors. And so what we aim to do and something I think I see in a lot of spaces is requests tend to come to us as being sometimes complicated.

And what we find ourselves asking is how can we simplify this into a singular action? How can we simplify this to a point where a frontline rep is going to know how to implement this or a coach is going to know how to enact this in the coaching space? And so we’re producing content that supports sales behavior, like how to do pre-call research, where to look for, how to identify who to call, when to call, and really making sure it’s catered towards individuals and making sure it’s approachable by our coaches.

Meredith Farley: So kind of creating the process documentation and how to, for elements of the sales job, that then the coaches take that content and they use it to, all right, guys, like, here’s the documentation around how we want you to be doing research, around prospects, here are the steps, and then they’re kind of rolling it out and coaching the sales reps about how to utilize those frameworks.

But you guys are the ones who are thinking about what has to be done and how do we present it in a succinct and readable way? Do I have that right or am I missing something?

Brianna de L’airre: We try to make things as simple as possible and I gave you such a complicated answer. What we’re doing a lot is creating e-learnings to support new coaches on how to coach. We create facilitation guides on coaching interactions. So, Meredith, if you’re a frontline rep on a team and I’m a coach, my team might create a facilitation guide that’s super straightforward that walks you through an activity of how to support a very specific sales behavior. And we also work with our tools team to optimize coaching tools to make sure they’re straightforward, equitable, and they are solving for the needs of our coaches.

Meredith Farley: Got it. And so, the coaches in some ways are kind of your clients?

Brianna de L’airre: Yeah. I think our sales partners are our clients and at the end of the day are our true clients, the businesses that we’re working with. We have to keep their interest top of mind as well. But predominantly, we’re working with frontline managers and we’re working with coaches. We have a kind of a unique team with coaches in B2B called the senior sales coaches and they’re entirely a team dedicated to coaching frontline reps to help support managers with coaching. And so, we work really, really closely with them helping to design their training curriculum for when we bring new ones on board and making sure they’re holding true to our coaching methodology.

Meredith Farley: Got it. So, the sales team has a direct manager and then the coaches work with the sales folks and support the manager in training, process, onboarding, sales behaviors, all that good stuff.

It’s kind of, it’s really interesting because it’s internal content, but obviously incredibly commercially important content. I think a lot of times when folks think of content, they think, you know, blogs for a website or an ebook or that type of industry facing collateral. How do you think internal content is different and what are kind of some of the challenges of creating it?

Brianna de L’airre: Yeah. That’s a good question. And I think it’s something that we’re always looking to innovate on and improve on. I think something that I always keep as a North Star is that whenever you conduct a training or you have a coaching session or you’re engaging with content, it has to be as valuable, if not more valuable than that person’s time connecting with their, have to immediately be relevant. It has to immediately be applicable and they have to know what’s in it for me.

So when we think about creating content to support managers, sales rep coaches, we really want to make it action forward. We really want to keep adult learning principles top of mind. They have to know how to immediately apply it to their role. We have to make it approachable and easily understood. So we’ve been leaning very heavily into video, we’ve been leaning into audio, you know, instead of doing scenarios, we’re trying to directly take transcripts from interactions with customers and really make it as applicable and understandable as possible up front.

Meredith Farley: That makes a lot of sense. As you say it, I’m like, I kind of love these as guiding principles for content in general. When you talk about adult learning styles, can you say a little bit more about that?

Brianna de L’airre: Yeah, adult learning principles. So there are learning principles for children. There are learning principles for adults. And so it’s kind of like the difference between pedagogy when you’re a kid, you’re a sponge when you’re a kid. You can just sit in a room, someone can teach you geography and you can learn geography even though it’s not directly applicable to you immediately, but you learn it.

As an adult, we learn completely differently. So you need to, when I’m learning something, I learn best by doing. You know, you have to immediately understand the value of what you’re learning and be able to apply it immediately. And you need to have your objectives up front. You know what I mean? It’s kind of the guiding framework that we use when we’re creating content.

Meredith Farley: That makes a lot of sense. I feel like as you’re talking about that, I’m thinking too about how important that is for things like internal email communications out of business. And also, I would say email marketing and social media messaging too. You have to immediately tell people in one breath what this is and why it’s important to you. Otherwise, whoosh, moved on.

Brianna de L’airre: Yeah. I don’t care. And especially for salespeople, where I know it’s like the old saying, time is money, but it’s true. I challenged my team to say, if we’re in a meeting with someone, if we’re taking someone off the floor, what we’re offering has to be more valuable than the amount of money they could have made on the floor with their clients. So we, at the end of the day, money is king, right?

So we have to be able to prove our worth. We have to be able to have a value at stake and say, this is why it’s important that you read this. This is why it’s important that you engage with this training. And this is why it’s important that you’re coaching. You could have a little ticker on everyone’s video monitor that’s like this.

Meredith Farley: I love this brutal side of you, Brianna. I love this. Okay. So that makes, but so when you talk about pedagogy, you were a teacher for a moment. And so I’m super curious, maybe you could kind of walk back and, you know, you are also, obviously you are a business woman, but you’re also an incredibly talented artist and maker and the most like prolific creative working person. I know I don’t know how you do all these art projects all the time.

So could you talk a little bit about your personal journey from art and art school to teaching and then to B2B sales enablement?

Brianna de L’airre: Yeah. I grew up in the streets of art school. So I have a very unconventional background in the world of business, maybe it’s not so unconventional because, you know, artists are business people as well, but I went to school to be an art educator and to be an artist.

And kind of like, I joke about it, but I feel just like lucky to be here. You know, when I was early in my career and envisioned myself as the artist warrior like person out here making art, changing the world. And my father has always joked that I was designed and meant for Harvard Business School. And to this day, he’s still like, Brianna, you have to go to Harvard, dad, we can talk about it. But like while in school, it was somewhat ingrained in me that artists are also business people. And you know, anyone trying to make a livelihood or to sell their work needs to pay themselves back, needs to pay themselves first. I had one professor, Steve Locke, who I still think about all the time and he’s an amazing artist and you should check out his work, he’s super, super cool. And I just remember someone being like, Steve, how do you, how do you do this?

And he was like, well, start with minimum wage, pay yourself at least minimum wage, take into account all of your materials, take into account your education, take into account time spent, figure it out, break it down square inch by square inch and then price your work that way. And it’s like one of the most straightforward lessons I’ve ever had about knowing your own worth. And so, you know, you learn a lot. It sounds ridiculous. You learn so much in school, but you learn so much more than, you know, the curriculum and my art school education really taught me the importance of my own time.

And so I, when I graduated, I was teaching for a little bit and I, you know, I went through my practicum. I left knowing I didn’t really want to be a public educator, but knowing that I really love working with people and I, and knowing that I really loved like human interaction and bringing the best out of people. And I was just lucky enough to know someone who worked at Wayfair at the time who was like, Hey, we’re hiring if working with interior designers, you have an art background, you’ve worked in retail, why don’t you give it a shot, ended up getting hired as an entry-level salesperson. And just thinking I am going to be in this job for maybe a year, maybe a year, because again, I had the artist warrior mentality and then struggled with myself because I loved it.

I beat myself up so much because I was like, Oh, I’m just following in the footsteps my father laid for me as a child, it’s all like the Harvard business school mentality. But I really loved working with people, I really love selling, I really loved Wayfair. It’s been just an amazing environment to grow up in. And so I found myself with incredibly driven ambitious managers who defined my success as their success, you know, I had one manager, Jess Harrington, I’ll never forget saying like, Brianna, if you succeed, it means I’m succeeding.

And so with that mentality in mind, grew my career at Wayfair, moved from an entry-level salesperson to a senior salesperson to a manager, sales manager, and then transitioned into training and coaching. And I’ve been lucky enough to develop my role in training and coaching and grow my team. And it’s been just an absolutely crazy adventure. So long winded. I’m so sorry.

Meredith Farley: No, it was totally great. And I was kind of just, as you’re talking, I was remembering going, like visiting you in the Wayfair office, which obviously pre COVID, and it was just kind of like a magical space with scooters or something.

Brianna de L’airre: Yeah, it’s, you know, it’s got strong startup vibes. The snacks were good. Absolutely infamous. Absolutely infamous.

Meredith Farley: Well, it’s kind of funny how you, you know, you were an art education and you’re still like you’re in a somewhat of an educator role right now. Do you feel that way? Or does it feel very different from that in practice?

Brianna de L’airre: I think coaching and educating are different. Like coaching and teaching are different for sure, because teaching and especially, you know, I went to school to teach public, like K through 12. And so childhood education is so different. Again, kind of how we discuss adult learning principles, but I also think coaching is so much more about self discovery while teaching is imparting information.

And so I do leverage so much what I learned as an educator in the coaching space. But I think my takeaways from that are maybe not as straightforward. I think like, I think a lot about the idea of a classroom learning space. And that’s all taken from, you know, when I was a teacher, I had, I feel like I’m referencing so many people from the past, but I had one professor in school who was saying, don’t forget about the importance of your walls, right? Your walls can teach. And so in a virtual setting or in a coaching setting, I’m thinking like, how can I create an environment that is also conducive to learning and learning and self discovery?

Meredith Farley: Oh, interesting.

Brianna de L’airre: Yeah.

Meredith Farley: Like, so when you’re saying your walls can teach, he’s referencing the things you as a teacher might choose to put up on the walls. Yeah. So, and all right. So what are, do you feel like one can create a virtual space? I suppose it would be your own workspace that is somehow coaching or teaching. Is that possible?

Brianna de L’airre: I think what I take from that is that space is intentional. And I think you can do that in a virtual setting by creating a space by calling it into existence. So you can say like, Meredith, so excited to meet with you today. We’re gonna have a coaching discussion, like before we get into it, we can talk about X, Y, and Z, but are you ready? Like here’s our goal for today and kind of like establish the space, you know?

Meredith Farley: Yes. I love that. I feel like establishing the space just through like, I am speaking into existence, the structure that we are going to inhabit throughout this conversation. Yes.

Brianna de L’airre: Yeah. And this is our goal, you know? Or are you ready? Because it has to be an educated guess, right? Like coaching is a two-way street and so much of it is uncomfortable. Like coaching should kind of be uncomfortable because it’s challenging. So being in the right mental space in order to have a coaching conversation is so important.

Meredith Farley: Do you mean, and also too when you said coaching is kind of about self-discovery, you, I presume that you mean coaching is about helping the one being coached to discover. So when you say it should be uncomfortable, do you mean like the one being coached might feel a little uncomfortable?

Brianna de L’airre: Yeah. Yeah. Absolutely. I’m a woman of many one-liners. One of my favorites is you can’t grow when you’re comfortable and you can’t be comfortable when you grow. And that’s why they’re called growing pains. But it’s challenging, you know? Especially when you’re being coached on the right thing, it’s resistance to it because you’re ingrained in a certain way, right? Feels like you’re challenging, you know, it feels like you’re challenging something that has grown in a specific way and that always is like, oh, it feels weird, but that’s kind of how you know it’s working.

Meredith Farley: Yeah. I think that’s a really, a very thoughtful thing and helpful to keep in mind because a lot of roles, like so many roles like job specs, et cetera, you know, people are looking for a player coach. Like their coaching has become such an important part of what kind of manager somebody is.

And when, if you’re pushing someone in a direction and you can tell they’re feeling a little uncomfortable, I think a manager needs a certain amount of experience to feel comfort with their staff’s discomfort and to be, and to not, you know, cow-tow to like people pleasing, smoothing things over, not having the conversation you need to have because it feels a little confrontational or a little potentially just challenging, I suppose.

Brianna de L’airre: Yeah. I think you’re hitting on radical candor. Yeah. It’s like you have to care. You have to care, but you have to challenge. Okay.

Meredith Farley: We’ve talked about radical candor. Would you mind defining it a little bit here in case folks aren’t familiar?

Brianna de L’airre: Yeah. Yeah. Radical candor. I mean, it’s like caring implicitly, having like genuine care for someone, but also challenging them. It’s a matrix, and I am forgetting the name of the woman who is the author of Radical Candor. I’m going to look it up. Okay. We can throw… It is worth, it is worth knowing. Kim Scott. Kim Scott is the author of Radical Candor. All right.

Meredith Farley: We can throw some radical candor notes in the show notes for anyone to check that out.

Brianna de L’airre: The concepts of radical candor are so important, and I think the other thing to remember is there’s no such thing as a… You don’t just become a coach. Coaching is also a learned skill. There are skills that go into being a good coach, and it’s a practice. I actually like referring to it as a practice, like my own coaching practice, because it’s something that develops over time, it’s a language you develop, but the core concepts of creating safe space, like a psychologically safe space, to have a one-to-one connection where your coachy knows that you have the best intentions for them.

When you’re challenging them, it is in an effort to see them grow, and really just making sure that in that scenario, if your coachy says something that’s wrong, if you’re the coach, you owe it to them to say, hey, that might not be the right answer, but have you thought about looking at it this way, or what’s another way that you can answer that, or this is wrong because X, Y, and Z, so really spelling it out, what is another way that we can do it?

Meredith Farley: So a responsibility to not let things slide because of the dynamic you have both consensually entered into, which is that you are the coach, they’re the coach-ee, or mentee, you care about them and their performance, and as such, you’re going to be candid in a radical way.

Brianna de L’airre: In a radical way. Otherwise, you fall into one of the other matrix quadrants is ruinous empathy, and that is when you basically just yes someone, or if someone gives you the wrong answer, and you’re like, that was awesome, but then they never improve. You’re never going to see improvement if you just are a people pleaser.

Meredith Farley: Yeah. I mean, whenever we talk about this, I feel like I know I sometimes am conflating coaching with management, but I feel like it’s just so true. So like remind me again, the X axis is what? What’s on the X axis of this matrix?

Brianna de L’airre: So care and challenge.

Meredith Farley: So say cares on one side, challenges on the other side, and then the Y axis is what again?

Brianna de L’airre: No, no, no, care challenge.

Meredith Farley: Oh, care is the X axis. Y is the challenge.

Brianna de L’airre: Exactly. So you have obnoxious aggression.

Meredith Farley: So let me guess which that one is obnoxious aggression is high challenge, low care.

Brianna de L’airre: Yes. Exactly. Exactly. There’s ruinous empathy, high care, no challenge.

Meredith Farley: Ruinous empathy. You care a lot. You care almost so much about how they feel, and you’re uncomfortable when they’re uncomfortable so you’re not going to challenge them at all.

Brianna de L’airre: Yes. Exactly. Okay. Exactly.

Meredith Farley: And then radical candor is, high care, high challenge.

Brianna de L’airre: Yep. And then there’s manipulative insecurity. Manipulative insincerity. Sorry. Manipulative


Meredith Farley: Oh, that sounds like a psycho one. So that is like, that would be, wait, manipulative insincerity. That would be, what’s that, high, what is that one? High challenge, low care.

Brianna de L’airre: So that would be, it sounds like you care, but you’re not challenging. Or like, you’re not, you’re not caring or challenging.

Meredith Farley: Oh, no care, no challenge, just manipulative insincerity. Yeah. I have to say, this is the second time I’ve tried to talk about a matrix with someone on this podcast. I think I’m doing better this time, the first time I glossed over, but I hope that there’s a lot of visual learners listening because we’ll put it in the show notes. I think it really applies to lots of management and I also love how vicious and brutal these are.

Brianna de L’airre: I know, the nomenclature is radical. But I think like, I’m actually interested in the conversation around the differences between managing and coaching because in my mind, I think they are different. And I think that we ask managers to be coaches a lot. I think the expectation is that if you’re a manager or coach, but as I said before, being a coach is a skill and one that you need to develop, it’s not just like the second you become a manager, you also become a coach.

So I think there are like very specific differences between the two. I think managers have to be really powerful feedback givers to be able to find the sand and say, here’s the situation, here’s the behavior, here’s the impact, whereas coaches are really strong question askers to say, what happened? What did you see? What did you learn? What will you do? And I think those are two very different frames of mind. Maybe I’m thinking like way too black and white, but I think those are different styles of conversations and I think they yield different results and both are incredibly important.

Meredith Farley: Yeah, totally. I think, I feel like I vacillate between the two throughout the day, depending on the relationship I have with the person that I’m overseeing, I think probably more junior folks, I probably manage a little bit more, I’m more like, these are the four things you need to do, any questions great. And then for folks who are either more senior and or who I feel like have potential to continue growing into their role a little bit, I’m probably doing a lot more coaching and just giving them tons of boring anecdotes that they’re very politely listening to me about.

So how would you define the difference between the two? Well, I guess you said already, like so like coaching is like questioning, helping them discover in themselves their own, the answers, and then kind of putting guardrails on it and management is more just like, you did this wrong next time, do this, like a little more one sided, would you say?

Brianna de L’airre: Yeah, I don’t know that it’s always has to be like corrective or I think managers set expectations and they define terms of success and they establish goals and you help your team by removing roll blocks, you help your team by providing feedback, you, you know, you support your game in that way as a manager and you have management conversations, right?

Like there’s a difference between a performance management conversation and a coaching conversation. I feel like that’s kind of where the distinction comes into play. But just like you said, I think, you know, you, you, you switch, you know, you go back and forth, you can have a management conversation right before you have a coaching conversation. Hey, Mayor, I’ve noticed that you, there has been a drop in the amount of outbound calls that you’ve made. And so the goal that we have is X, Y, and Z. Let’s have a coaching conversation. Let’s talk about it. All right. Or, you know, do you want to have a coaching conversation about that?

Meredith Farley: It’s kind of like you manage situations and you coach people and behaviors.

Brianna de L’airre: Yes, exactly. You manage to results, you coach to behavior. Like that.

Meredith Farley: All right. Cool. Well, let’s come back a little bit to your own team and your own management style and collaboration style. So it sounds like you are doing daily group ups with your folks. Is that right?

Brianna de L’airre: That is correct. Yeah.

Meredith Farley: So like how do you approach them? How do you structure them? What are you trying to accomplish in those moments and meetings?

Brianna de L’airre: Yeah. Yeah. I think, and I said this to my team, like my, my goal for my team is to have them feel and be empowered so that they feel like, even if they don’t know the answer to something, like they’re able to find solutions, they feel empowered to share their voices. I want them to basically work me out of a job. My goal for my team is to feel like even if I’m not there, that they have things completely under control.

Meredith Farley: It’s a great goal.

Brianna de L’airre: And so I work really hard to create an environment that I trust them implicitly. I have a new employee. She’s been in the role for maybe like 90 days now and she is already owning projects, building relationships across teams and it kind of starts with day one of just calling that into existence saying, Hey, I trust you, we’re going to work together, you’re going to make mistakes, that’s okay. It’s not just okay, it’s kind of my expectation because the only way you’re going to learn is if you make mistakes.

And so as a manager, I’m also a coach and I am building the behaviors of ownership and leadership, strong content developers who are, you know, using critical thinking techniques and, you know, challenging for clarity and really, really strong communicators.

Meredith Farley: I think, and I know we’ve chatted on it a bit, but I think in a remote world, those daily touch points are, well, for me, they’re super important. I love talking to my team every day, even if it’s not a super formal reporting meeting of any kind. It’s just like, Hey, how’s it going? How are you feeling? How’s the team feeling? Let’s chat about XYZ and I feel like it makes me feel more, it reminds me that I’m working with people.

I’m not just working with a computer screen, but I know there are some folks who feel a little bit differently and I have never been a, this isn’t, this could have been an email person. Really? I mean, maybe I just, maybe sometimes I think I, well, no, I’ll be honest. No, I haven’t. I think it’s because, I think we’ve talked about this a little, there’s that essay managing oneself, which is a great classic essay and they talk a lot about at one point, like, are you a reader or are you a talker?

And the anecdote is that I think it was LBJ after Kennedy was assassinated, came into Kennedy’s team and Kennedy’s team. Kennedy was a huge reader. So they would put complex, comprehensive briefs together. He would read them earlier in the morning and just know everything. He’d like absorb it, be like, good, I’m good for the day, I get it. And he’d be briefed and they were doing the same thing for Johnson, who was not a reader. And he was just like, they were like, why is he like, didn’t he read the briefs? He doesn’t know about XYZ, but he was a talker.

So he, what he needed was people to come in and like talk to him. He’d ask questions and I always assumed that I would be a reader since I was a writer, but I am not, I’m a talker. And it’s helpful for me to process and talk things out because I feel like I’m going to have questions, et cetera. And but I don’t know if it comes back to like one thing I feel like we’ve talked about that I’m really interested for your thoughts on is when we think of salespeople or leaders generally, we tend to think extrovert. I’m curious about how introvert versus extrovert impacts how you lead your teams and like what you think. How does one need to be an extrovert to be successful in sales?

Brianna de L’airre: I think it’s a really interesting question. I don’t think you have to be an extrovert to be successful in sales. I think extrovert, like I’m an extroverted person with like introversion caramel center. Like I’m an introverted extrovert or an extroverted introvert. I’ve got a little bit of both. I think everybody does, but I think in sales, we tend to reward people who exhibit extroverted behaviors. But just because you’re extroverted doesn’t necessarily mean you are a very, very strong salesperson. I mean, obviously, right? I think to me, strong sales folks are listeners.

People who are listening to their clients, they’re people who are identifying areas where their clients need help because the best sales are ones that clients are excited to make. People who are excited to make sales are ones who like see the value in what they’re buying. And so like with our sales team, we’re working with millions and millions of products and we’re working with a whole swath of types of clients and businesses that all have really particular needs that all have different things that they value. And so if you’re just the loudest person in the room, and I’m saying that extroverts are always the loudest person in the room, they’re not.

But if you’re so extroverted that you forget to listen, you might sound like a great salesperson, but it definitely won’t show up in your numbers. I’ve definitely been coaching and listened to calls and said to myself, this sounds like such an engaging call, but why didn’t it go anywhere? And then you actually think about the actions on the call. They just had a great conversation, but it didn’t actually lead to a next step. It didn’t actually lead to uncovering the client’s need or anything. And so if you’re not a really strong listener, you’re not going to get anywhere.

Meredith Farley: So if someone is an introvert and they want a career in sales, what do you think they might need to be mindful of in so far as perceptions or behaviors that could help them be recognized for the abilities that they have, even if they don’t fit a stereotypical mold?

Brianna de L’airre: Yeah. I think sales is one of the more beautiful career paths because at the end of the day, it’s all results. So even if you don’t sound like what you think of when you think of a salesperson, if you have the results to show that you’re effective and you’re impactful, that’s really all that matters. So if you’re a more introverted person, I would say lean into curiosity. I would say lean into questioning and lean into listening. And if you are a curious person who is interested in learning about people who ask the right questions to uncover the needs of your clients and you are able to identify the products that they need, you’re going to be a successful salesperson.

Meredith Farley: I love that. That’s really interesting. So kind of somewhat related to introversion, extroversion, people feeling like they fit the mold of the job that they have or want. Imposter syndrome, number one, do you think you have it?

Brianna de L’airre: I definitely feel, I have moments of imposter syndrome. And I think part of that might come from the non-traditional background where I’m like looking around and I’m like, oh my God, it’s me. It’s me. I’m making. I absolutely respect, appreciate, and have put so much value into my education. I think sometimes I’m like, oh my God, I have gotten here from experience. Where I am in my career is because of the experience that I’ve had in the people that have been such amazing managers and coaches. So I definitely encounter moments of imposter syndrome for sure. And I think what I’m appreciative of is that those are just moments, you know.

Meredith Farley: Yeah. It’s not like the full on like, oh, every day you first work through a wall of imposter syndrome.

Brianna de L’airre: Yeah. But I think that’s a part of growing pains, right? Anytime you feel imposter syndrome is a crossroads of feeling challenged. And so it’s a moment for myself to look at my own career from a coaching perspective and to provide myself some feedback. And I was like…

Meredith Farley: is it like imposter syndrome?

Brianna de L’airre: But it’s not the syndrome. It’s like the, it’s not that imposter syndrome is a coach. What it is is the bioproject of feeling challenged. And so, you know, when you go to a place and, and like this is what our perhaps feel like or this is what, you know, anyone who is growing in a role has, has moments of questioning their own performance has moments of questioning their own value and their own input.

And I think just as I would hope our coaches would challenge our, our coaches to say like, hey, you know, why are you feeling that way? Or can you talk me through that feeling, where is it coming from? Because what it is is a symptom, but it’s not the cause, right? And so you don’t coach the symptom, you don’t coach the imposter syndrome, but you want to take a look at like where you think it’s coming from. And then you can make an action plan against it.

Meredith Farley: I think that makes so much sense. And I think too, that like, I feel for folks who are like 22, 23 in their very first job out of school, everything feels so challenging sometimes because you’ve never encountered it. You’ve never worked through a moment of imposter syndrome or a moment of being like, who am I? How did I get here? Is this really my reality?

I kind of wondered too, I feel like sometimes what’s been helpful in the past around those things is like, you know, you read the room for a sec, you get a little validation. You’re like, no, what I said wasn’t insane or the way I approach this is normal. I wonder in a digital environment, how, if they like, how they get that same positive confirming feedback or reassurance. I’m sure it happens…

Brianna de L’airre: I think it’s interesting because I don’t think feedback is passive. What you’re talking about is walls talking, right? Walls teaching, where you look around, you see behavior around you. You’re in an office space. You can model yourself off of someone. You can have a, you know, yeah, in a virtual setting, it’s so much harder, right?

The lens is a distancing, it’s really, really hard to say, you know, how was my performance chalking up against another person’s performance or is my performance chalking up against my own expectations for this role? And so you kind of have to switch your mentality from passive to active in that case, and it is more challenging.

I know like it’s exhausting, it can be, but being more engaged is so important to reach out and ask for feedback and, you know, get 360 feedback. Ask for feedback from your stakeholders, ask for feedback from your clients, ask for feedback from your manager and your manager’s manager, and like ask for it in the spirit of radical candor.

Meredith Farley: I love, I think that’s really, really good advice. I love that. It’s hard and uncomfortable.

And it’s funny too, I think maybe another element of that is too, is being willing to give feedback when people ask and, you know, figure out a way to be truthful, though kind. I think so often people might, too, you know, you ask someone for feedback and they might not feel, for whatever reason, like comfortable saying what they actually think. And so it’s like, what did you call it, being very proactive and active and engaged and asking for the feedback, and then also as a colleague being a willing participant and like providing that feedback to folks.

Brianna de L’airre: Yeah. And asking for feedback on specific things, right? I think asking for vague feedback can be more harmful sometimes, I don’t know if that’s the right word. Ask for feedback on a very specific thing and especially if you’re, you know, to circle it back, having imposter syndrome, like isolate out what’s triggering that and ask for feedback on it. You know, we can’t see, like we need mirrors to see ourselves and people who are mirrors in this digital environment are colleagues and, you know, our managers. So that’s the only way we can truly get a good snapshot of where we are.

Meredith Farley: Yeah. Like, that’s a sound bite, we should save that.

All right. Well, like in the last few minutes, I don’t have too much time left, but we’ve touched on the fact that you are an artist, you’re a maker, you have a very creative background, and then you’re in this very, you know, commercially focused role. How do you balance that? Sometimes I wonder, is it work for you to push yourself, like, because you’re very prolific, you do like more crafts and projects in one year than most people do in like a decade. Does that come back? And then also sometimes I’m curious, do you ever feel like one of your identities fits you more than the other? And how do you balance those two sides of yourself?

Brianna de L’airre: Asking the deep questions, Meredithj. I don’t think that I don’t see the two sides of myself as two sides. It feels like a whole thing. But I think I am a real big proponent of work time is spent in work time, and then everything else is your time. And so I think time management is incredibly important, which again, a practice, not something that is perfect, but, you know, really holding true to working hours, making sure they don’t bleed into your own personal outlook.

And then like some, a piece of, I don’t know if it’s feedback or reflection from my father, who is one of the wisest human beings on the planet, and I think we actually talked about this yesterday, but like your mind recharges in two ways. One of them is sleep and one of them is play. And so it’s an important practice in this world to figure out what your play is as an adult, because it’s not the same thing when you’re a kid. Figuring out what is play to you. And so I really, really am charged by, you know, creating and making and exploring.

And it looks, I think like you kind of refer to how I have a lot of different creative practices. But part of that is just like following curiosity and like exploring new things and new mediums. And I am so incredibly grateful to have a role, a job that allows me to sustain a creative lifestyle and allows and supports my artistic practices.

Meredith Farley: I mean, I think that’s a really helpful way to think about it. And I guess I asked that question too, thinking about some people who maybe work in creative fields, creative marketing, who kind of struggle sometimes where they’re like, oh, I thought of, you know, it feels a little bit like they’re doing something adjacent to what they’d hope to do.

But I think the way you’re outlining it is like a really healthy mental framework for thinking about your job as something that supports your creative life as opposed to the reason why it has to be your creative life.

Brianna de L’airre: Well, listen, I went through all that when I was in my early 20s, when I first got hired with Wayfair. And I was like, I’m supposed to be like a warrior poet, I’m supposed to be like, and it was, it was the concept of supposed to be that really got me like that was the thing when I went back to reflect on that. I was like, who said that? Who said I was supposed to be this? Who said I was supposed to be X, Y, and Z? And what gall? Like what? It was myself. Right? I was like, how dare they say this about me? But it was myself.

I was the one who was saying your creative practices and passions are supposed to be the things that fuel you. And why? Like to what end? I actually get so much more satisfaction from flexing into a part of my brain that I otherwise wouldn’t have known I loved. I love problem solving. I love communicating. I love working with different types of people under a shared goal and finding solutions. Like that is so fulfilling to me. And it’s different than the part of my brain that is like wildly fulfilled by creative endeavors, but me. And so I don’t feel the need to sequester my identity into one or the other. I think there are elements that bleed into both.

And so I think anyone who’s like really struggling with identity and like professional identity and how it is like that concept of supposed to be, I’m supposed to be this. Take a look at what you like about one aspect of your work. Take a look at what you like about your creative endeavors and like, do they have to be each other? And for some people, it’s yes. And that’s totally fine too. But I think a lot of us feel a lot of applied pressure and we’re the ones applying it.

Meredith Farley: Yeah. I think that’s a great, really helpful advice. And I feel like you gave some amazing nuggets of wisdom throughout this conversation. So thank you so much, Brianna. And if you want to like follow you, LinkedIn with you, et cetera, where are the best spots to look up Brianna online?

Brianna de L’airre: Yeah. I think LinkedIn is the best spot. So Brianna de L’aire and I apologize. Well, I don’t apologize, but I warn ahead of time. My last name is a little bit like a password.

Meredith Farley: I’ll put it in the show notes. Everyone it’s got apostrophes and lowercase letters where you don’t expect them.

Brianna de L’airre: Grammar, Meredith. There’s grammar in there. Be careful. But LinkedIn would be the best place to connect. And if anybody has any resources that they want to share with me on coaching, on sales behaviors and developing teams, I’m always a student, always learning, and I’m always looking to support my own practice. So I send it on back if you want to connect with me. I’ll connect with you too, and I’m so excited to grow the network.

Meredith Farley: All right, everyone. Hope you enjoyed our chat with Brianna.

Ian Servin: Next week, we’ll be talking with Jessica Holton, CEO and co-founder of Ours, a relationship health company.

Meredith Farley: And we’ll make a couple little plugs here to support the show. You can rate, review, and subscribe. Those things make a huge difference, and we appreciate it. And if you like this conversation, you would probably like my fledgling newsletter, Content People. We’ll throw a link in the show notes to subscribe if you’re interested.

Ian Servin: And that’s it, folks. Thanks so much for listening. If you want to get in touch, you can always email us at