Samantha Pitre Quillen – Playing Poker, Cutting Cake | Conversations with Coaches | Boxer Media

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Samantha has coached clients at all levels – from CEOs to interns – and traveled extensively to teach people how to find career clarity, take their seat at the table, and make a real impact in the spaces they occupy. With over 15 years of HR experience in the corporate and start-up worlds, she understands that success is the intersection of opportunity and experience.

In this episode, Samantha and Kevin have a WIDE-ranging conversation – covering high-level coaching concepts, broad career strategies, specific tactics for realizing your goals…and really everything in between!

However, one message rises above the rest: Remember to dream like your six-year-old self, because big boundless dreams are the key to becoming the best and truest version of You.

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Kevin Stafford 0:00
Hello everyone and welcome to another episode of the formerly called Coffee with Coach’s podcast. We’re transitioning to conversations with coaches, which is just a little more literal. So we’d like that I’ll be drinking coffee, but we’ll be having a conversation and that’s the important part. I am your host, Kevin. And today I have with me coffee drinker, tea drinker, coffee drinker?

Samantha Pitre Quillen 0:21
Coffee intravenously.

Kevin Stafford 0:24
Nice, nice, nice. This is Samantha Pitre Quillen. Samantha has coached clients at all levels, from CEOs to interns and everything in between, and traveled extensively to teach people how to find Career Clarity, take their seat at the table and make real impact in the spaces they occupy. With over 15 years of HR experience in the corporate and startup worlds. She understands that success, and I love this line so much. Success is the intersection of opportunity and experience. Samantha, thank you for that line. It’s a beautiful way to sum up what success is. It’s very synced very deep. I love it. And thank you for being here.

Samantha Pitre Quillen 1:01
Oh, thank you for having me. I’m super thrilled about the opportunity. And I can’t wait to chat.

Kevin Stafford 1:06
Awesome. Well, let’s just go ahead and get started. And let’s get started at the start, begin at the beginning your superhero origin story, as I sometimes like to say, How did you become slash realize that you were a coach? Someone tell you or did you just kind of behave like a coach for a while and suddenly realize like, oh, so there’s actually a name for who I am? And what I do I should do that. Did you go from there to beginning a coaching practice?

Samantha Pitre Quillen 1:33
Sure. Um, so I’ll tell a story. As I was, I was the head of People Operations at a small startup. And my personality has always been, dive into your work, do good work, really show your results. And so I was pitching to our CEO, a learning management software platform that I thought would really revolutionize the way we were developing talent. And the way that we were intersecting with our succession planning and strategic planning and all of that. And at the same time, I had of sales was pitching to have our CRM revamped reran. And our CEO explained that he wasn’t going to have enough capacity, you do both projects, and asked us to prepare business cases. And he would make a decision. So we did that. I presented my business case, he said, and he was like, This is great. Let me take a couple days, I’ll come back to you. In the meantime, it was our monthly birthday celebration for the team. And I went to the event. And I noticed that the the team that was putting on the the individuals that were putting on the event, were struggling to cut cake. As the daughter of two amazing bakers, I’ve been cutting cake since I was eight, and often had my life threatened if I mess up cutting the cake. So I jumped in started cutting cake projects, managing where the cake distribution should go all of the things. And in that, and while I was doing that, covered in case covered in icing sticky the whole deal. I looked over and the CRM, I mean, they haven’t sales, and our CEO for having they were having this chat. They were laughing, they were joking, they were really just having a good time. And I kept I kept cutting cake. Two days later, our CEO came back and said that he was going to go with the CRM overhaul that our head of sales had suggested. And it was in that moment that I realized they were playing different games. It wasn’t playing chess versus playing checkers, they were playing poker. And all of the people that I interacted with every single day, they were putting their heads down, looking to do good work. Really looking to be the best employees that they could be. That wasn’t the game. And if I didn’t know the game for that long in my career, other people didn’t know that game that game either. And so it started and so in becoming a coach, it started with doing the referrals, friends of friends just helping out jumping in solving problems were coming and going to being a coaching practice was because I began to understand there are so many people out here who who just don’t have the community, they don’t have the community so they don’t have the support. They don’t have safe places to go to workshop problems, to brainstorm ideas, all of the things strategize. Like a lot of folks were out here with just no career plan, they were just out here, playing pinball, you know, bouncing from this opportunity to that opportunity. Maybe somebody was kind enough to show them some new opportunity that they didn’t know existed, but they weren’t being strategic. They weren’t being they didn’t create communities and networks, that were really designing them to have real clarity about what they wanted to do to make impact in the spaces that they were occupying to claim their seats at leadership tables. And so And notice, I said, clean, and I’m so big on that word claim, because I think people have earned the seat, alright. It’s just a question of if you’re going to claim your seat or not. And it’s almost like luggage, right? Like, it’s sure you packed it, you checked it, what are you going to claim it? So that was how I became a coach. And that’s how I became, I started a coaching practice. And really felt like it was necessary because I could see all of the guests. And the last thing I’ll say to that point is, I recognize that there was no place as adults once you get out of college. But even when you talk about graduate school, maybe there’s a little bit of conversation, but there’s no place to go to learn this. There’s no There’s no place that’s really teaching this anymore, right? Like after school, where do you go to talk about networking or strategic brand awareness or promoting your brand or brand brand evangelizing?

Kevin Stafford 6:58
Yeah. And people say people like to talk about being lifelong learners. But a lot of times you just look at the way our lives are structured, our society is structured, you educate up to a certain point, and then that’s it, you’re done getting education, because you go to school, we got to go through high school, you go to college, you go maybe even as far as you go, you get a master’s degree, you get a doctorate, if you can get that in whatever field that you happen to be, and you go as far as you can, and then you’re done. It’s like, but no, that’s not the way life actually works. And you have all these people like in your identifying them perfectly, who are just out in the world, they’ve learned a ton from from schooling, and they have a ton more to learn. They know that they want that. But there’s nowhere for them to go, no one for them to turn to not in an organized way. Like you were saying it happens sort of ad hoc here. And there, you get lucky you stumble on a person, you find a mentor, someone takes an interest in you, etc. But this what you’re talking about, and I liked that you really emphasize the word strategic strategy, like what’s the plan for you to get the skills that you need this knowledge that you need this awareness that you need to play the right games at the right times, while still being the kind of certain kind of person who’s out there cutting cake, you know, you don’t want to stop helping people. But you do want to be playing the right games to get where you want to go. I love this so much. Obviously, it’s like get there’s so many different places to go from there. I love it.

Samantha Pitre Quillen 8:16
Yeah, it’s so important. And I think that it is about strategy and my exposure in startup environments have has helped me to understand that, that that the world is about metrics and strategy. If you don’t have an action plan, if you don’t have a roadmap, you’re just you’re you’re really just out doing a lot. But is it effective? Is it productive? Is it important? And as a, I’m dating myself, maybe but as a Franklin Covey, you know, sort of convert years and years and years ago, really isn’t important. Am I doing the urgent or not urgent and important tasks? And I think part of what defines important for us is or should be, what do we want? Some of and most of us don’t know that.

Kevin Stafford 9:12
That’s that’s, that’s frightfully scarily true. You think about that? It’s like, what do you what do you want? Like, if you just ask someone that question, they may have an answer, you know, they want you know, career advancement, or they want like, a certain size of house in a certain location. Like they’ll they’ll have like an answer. But then if you just ask them again, like, we want, though, I mean, I know that those are things and that are something like a career or a role or whatever it represents something that you want, but what do you want? And usually, it’s much more of a feeling or a state of being, you know, they want not necessarily you know, the house, but they want the comfort and sense of home that that can bring in to be able to maybe raise a family and there’s all there’s always like more to their answer than that when they when they first present. And it’s a scary question to ask somebody, what do you want? What do you really want because the implications can be well Life changing. To put it frankly.

Samantha Pitre Quillen 10:02
it can be and I think that when when you think about it, we also have not. After a certain point, we that’s not a muscle that we encourage people to use anymore. Because now we want people to be practical. We want people you know, when you’re a little kid, you get to dream super big. And super outlandishly. You get to say, I want to be an astronaut. I want to be a superhero. I want to be a tennis player, you a basketball player, you get to say I want to play football, basketball and lacrosse, right when you get to do all of it. And the older as we progress and anyway. People interject things like practicality, like you start to understand, like, difficult Miss priority. Yeah, all of the things. And I think that it’s that lack of one of the things that I do about clarity is like dream big. Like I tell people all the time channel, your inner six year old who wants to be a firefighter and astronaut, a racecar driver, you know, and a biotech and biophysics, right, like shadow your intersexual. Like what is like and that is a muscle that many of us, especially as adults, has atrophied unless we are proactively going back and really trying to use it.

Kevin Stafford 11:30
Yeah, a good friend of mine once put it to me in a particular way that really kind of stuck with me is that you can only you can only grow as big as your biggest dream. Which, which, when I first heard it, I was like, oh, that sounds cute. You know, I kind of like I didn’t dismiss it, but I was like, Oh, that’s a that’s a cute turn of phrase. I like that, then I have kind of like sat with that for a while in my life for years. I’m just like, you know, there’s some, there’s some real truth to that kind of statement, you know, and I love that that encouraged me to dream like a six year old. Because yeah, I think back to when I was six and man. I mean, I was having weird dreams, things. I was like, you know, they’d be an astronaut or whatever, but why not, you know, just like, let yourself dream to that whatever size you can dream to. And then, you know, find your way from there. I just I love that. It’s so and I think I think you’re right, people don’t, don’t realize that they not only can but should still be dreaming like that. Definitely. Let’s, uh, let’s move let’s move into the nuts and bolts of your coaching business. The way I like to ask this kind of it kind of captures a lot of where this conversation can go. Who do you coach? And how do you coach them? So the who obviously being like the, you know, what positions professional, personal, you know, CEOs to insurance, we’ve already kind of covered your spectrum. And then the how being Do you focus on one to one coaching or one on one coaching? Small teamwork, maybe like keynote speeches, even like, you know, book writing or course creation? So yeah, who do you coach? And how do you coach them?

Samantha Pitre Quillen 12:58
My clients are women and professionals of color. And we’ve already called recovered CEOs, to interns. However, they are people who understand that they are so there, wherever they are on their, the lifecycle of their career, they understand that they are seeking and needing support and community and, and guidance at so that they really understand that they don’t want to do this thing called a career alone. And when I talk about the lifecycle of a career, you know that developing those are the that early stage in the careers as you’re an intern, or early stage, professional who’s looking to try new things, explore, get into some things figured out some things you really don’t want to ever knew again. And oh, I like this, I could do that. Or maybe you’re looking for external transition. Now you’re in a space where you’re clear on where you want to go, what you want to do, that you’re looking for the right cultural fit. For an organization that really speaks to who you are and what you do, and how you enjoy doing it. Maybe you’re looking for an internal promotion, you’re looking to just get ahead and to take that next leap. Maybe you’re looking for people management, and really ready to lead a team of your own. And the last sort of phase if you will have a career journey and my opinion, is a person who’s looking to now spread their throughout their thought leadership that’s really looking to get how they view the world and see this industry, this profession, the work that they have done to share their best practices and expertise and, and design the future of this kind of their kind of work. So we really create opportunities, whether that’s one on one coaching mastermind Times groups. We, we create opportunities for that. And for them to get that support for them to find that community, for them to really have a place to talk through a salary negotiation, for instance, a way to wage job opportunities, one of the things that I realized that really was part of the impetus is, you know, I mean, in my as I reflect on my own career, I remember my, when I, you know, quote, unquote, made more than my, my, my parents. And it was one of those moments where I got a job offer and it was, I thought it was a lowball offer. But where was I gonna go to discuss that this six figure offer? For a head of People Operations was a lowball offer, was I gonna go to my parents who, in their entire career journey had not made that much money? Was I gonna go to my friends who didn’t do what I did? And some of them thought that that was a really, you know, a good offer? Or was I gonna go to my friends that were investment bankers who were like, That’s my bonus check. Where was I going to go. And I realized that without having a real community of people that understood what I was going through, even in feet, how I felt about the lowball offer. And not being in community with people who understood what I was, you know, what I needed to do strategically to get to negotiate a higher offer. It was, it was a lonely place. And so so much of what I now know it and see is that people make mistakes, just because they’re only they’re only getting advice from themselves or from other people who don’t know, either. And either way, it’s bad advice. The only way to get or improve, or get better advice is to really be in a situation where you have folks that just know and can help and share best practices. Courses just a moment, but that was coming.

Kevin Stafford 17:16
That’s cool. Good, cool. That’s okay. I’ll get back to that. Just a second. I just, I love I had this image as you were talking of someone walking down a path that had been walked down by 1000s and 1000s and 1000s of people before, but they’re walking on it alone. And they also can’t quite see the path. You know, it’s like this. It’s this weird combination of it’s like, there are so many people who exist who know exactly what you’re going through right now. And you don’t have access to them. And it’s just like, that’s, that shouldn’t that shouldn’t be, that should not be the case.

Samantha Pitre Quillen 17:46
Well, and I think one of the problems is also we use terms that we’ve never defined and never shown, right? Networking. Everyone, like we’ve all heard that term. If you said, Do you know what networking is? There’s literally no human being alive is gonna say no. However, when you fight when when I say things like, Well, what’s your strategy? When I say things like, Well, what’s your nurture? What’s your nurture pattern look like? When I think when I when I suggest to people that they do they’re sending emails that don’t speak to their value propositions? They are like, what? You mean, I just don’t say, Hey, I think you’re interesting. Do you want a coffee? Like, you mean, there’s more science and art and skill than that? It’s like, yes. You know, I see people do this daily that our networking is, you know, we also have vilified networking, networking, people are like, oh, yeah, I know what it is when you need a job. You know, you call up a bunch of people and tell them you needed to have and it’s like, and we don’t really we don’t have you know, one of the fundamental pieces is we don’t talk about what these things actually are. We don’t talk about you know, even when we talk about, like, finding a new job, everybody’s like, Oh, you just get an a resume that can get through an ATS, an applicant tracking system. And I’m like, No, honestly, that’s, that’s not effective either. Just applying isn’t the key either. So really helping folks to unlearn some things and giving them new perspective and new strategy on other things is so important.

Kevin Stafford 19:34
Man, I okay. You are clearly I have so many like I have questions conceptual. I have questions specific like you seem like you basically you have you have the full spectrum. You have the concepts, you have the strategies, you have the tactics, the details, the redefinitions the expectations to dream, how to dream, it’s like you’ve you’ve got it all. If you don’t mind me saying where can people find out more about you? Where can people connect with you engage with you? How do you like to meet people for the first time when they just want to know more about who you are and how you coach and maybe how you can help them.

Samantha Pitre Quillen 20:12
So the first step is our website, creating Miss And that is a great place of actually, I just got off a phone call not too long ago, as we are revamping and retooling it so that folks that get there can really a find things so much more easily as well as have access to this wealth of a library of information that I’m just kind of sitting on and not getting out. So the but the first way they can get past these creating Miss It is definitely going this later this summer, we are launching a blog that is really that, that I’m really excited about where I’m letting folks submit questions. And every week, we’re just going to answer questions that I think are going to be hugely beneficial to both folks that follow me as well as to, to, to new folks that just come in and just can scroll through and be like, I wonder if she’s got a post about such and such. And like they can also find us on Instagram we are at creating Miss Jones. It’s the same handle. And there we are always we’re doing a little bit of everything. We’re doing some q&a stuff. Some days, we’re doing some motivation. Never to you know, sometimes you just need a little pep. We’re doing some we’re doing some motivation. We’re doing some some q&a of I’m always asking for feedback. So if there’s nothing for me to have a poll on Instagram at all. And we are also this later this year, we will also have a YouTube channel by the same name.

Kevin Stafford 22:03
Okay, I was actually just going to ask about that. It’s like, it sounds like a YouTube channel is like if you don’t already have a goal, and it’s in your near future. Because you everything, your approach the q&a, the accessibility that oh, yeah, people are gonna want to see people want to see you and your, your people just talk and share.

Samantha Pitre Quillen 22:19
Yeah, really, the YouTube channel, we hope is going to be one of the things that I am huge about. Everyone doesn’t necessarily gravitate towards my style. And nor should we all have preferences, we all are a little unique. And so I can’t one of the reasons I wanted so to my head of operations, and from my team’s perspective, so I have an operations head of his like, can we just do one thing for a minute for you? Sorry. But one of the reasons I wanted to use his channel was so that I could bring all of my favorite other coaches to have conversation as well. I wanted to, because I know that that the you know, I’m not going to start naming all of the coaches that I think are so incredibly talented, I’ll be here, I’ll be here all day, somebody and they’ll be upset. But I want to bring all of those voices because I think that there space for all of us. This this, we look at how many people are in the workforce, we know that there are there’s a person for everybody. And there’s a coach for everybody in that same breath. So I really want to leverage the channel to be able yes to connect and talk to the clients that are gravitate towards me specifically, but also to share and open them up and maybe expose them to some coaches that they didn’t know existed, but they also will gravitate to as well.

Kevin Stafford 23:51
Oh, I love it. That said That’s right, like near and dear to my heart. Obviously, that’s a big part of what we do with this little podcast is just just letting people know that there are as many different kinds of coaches as they can imagine, and that there is a coach for them. And that it’s one thing that I have found. So I mean, it’s it sounds corny, but it’s heartwarming, the way that the entire coaching industry, every single coach I’ve spoken to, which is this point is over 100 And just for this podcast, they all understand that they have something tremendous to bring to the kind of people who would be a good fit for their coaching. And they understand that not everyone will be and they know at least three or 30 other coaches, whether they’ll be like, You know what, I might not be the coach for you. But you know, who I think might be this person, this person in this person. And it’s just it’s something it’s so universal across the coaching industry. I just love being a part of it and getting to amplify just a tiny bit and I love that you’re doing the same.

Samantha Pitre Quillen 24:44
Well I think what’s so important is we see if your whatever your genre, whatever your specialty and your niche is, you also see the bad folks out there. And so you you you want to share all of the other great people who are doing great work So almost silence or quiet some of those, those bad voices. So the fact that I can bring you with and the difference was, and I’m sure for you as well, but I’m bringing you folks that I’m, I’m backing I’m saying yes, this is a good one. So I was like, you know, when you’re you’re you’re you’re you’re really good friend gives you a restaurant review recommendation you’re like, Okay, well, so and so says that they like it and they’re a foodie, so I’m gonna go with that as well, that has, that is a really different way than just reading Yelp reviews. So, and I think especially in the career coaching space, there are so many folks out there that are just, there’s so much noise out there that I think having somebody say, hey, look, you know why, if I’m not for you, that’s okay. But this person is really good, or this person or, like you said, the 30 other ones that I can interact with and expose you to? I think that that’s so important.

Kevin Stafford 26:02
And I, I really love something that you you said right out. And it’s something I hadn’t quite thought about in this way before or I have, but it’s I love that it came to light right here at the end of our conversation is that the way to quiet or move the more toxic voices out of the conversation is not to shush them is to, but I mean, sometimes someone needs a good church, but really, it’s to elevate the voices that have something to bring to elevate the positive voices, the useful voices, the voices that are committed to the service, like it’s elevate the right voices. And that’s the way to quiet, but maybe not. So Right. Once I yeah, I left feel so powerful. I love that.

Samantha Pitre Quillen 26:42
Well, and I also think it’s because, you know, as we all know that, and I agree with you, some people just need to be silenced. But for the most part, silencing of voice without amplifying the good voices, there’s another one that’s going to come right back. It’s sort of like whack a mole, right? They’re gonna, they’re going to reform and they’re going to pop back up. So if you are just silencing bad voices, you’re gonna that’s going to be a full time job. Whereas if you’re amplifying good voices, they really will at some point, drown out the toxic voices. And they will give people the ability because they will have you know, more of those good voices, to also ask better questions, even of the toxic folks, to some degree so that you don’t have to even shush the toxic folks, they’ll just sort of not, they won’t select them. And that way, they’ll just kind of fizzle and die on their own. Man,

Kevin Stafford 27:47
I have already taken up more of your time than I scheduled and I feel like I could take up a lot more, but I’m gonna make I’m gonna make myself stop talking to you now. Samantha, you’re fantastic. Thank you so much for talking to me today. Thank you so much for being who you are. I love the everything that you represent the way that you communicate yourself the work that you’re doing. I love it, I am pleased to have just been a tiny little part of it today. So thank you for talking with me for being here and for doing what you do.

Samantha Pitre Quillen 28:15
Thank you so much for having me. I greatly appreciate it. And um, yeah, I appreciate the work that you do for coaches, some, I think a lot of times we forget that our voices are unnecessary, because there’s so much noise in the world. And sometimes it’s really great to, to be in a space with with someone who’s trying to amplify good voices. So thank you again for this opportunity. And I am just honored to have been part of

Kevin Stafford 28:45
it. Awesome. We’ll keep it we’ll keep we’ll keep all this good work going. Thank you. Thank you so much for listening. Everybody who’s listening to this. Freak out find Samantha learn more about her connect with her. You already know you won’t be sorry. So anyway, just wanted to say that. Love you all. We’ll talk to you again soon. Thank you

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