Speaker 1: It's hard to write a good profile because you have
Speaker 1: to really examine these tiny nuances like you don't have
Speaker 1: much space, but that means you have to have a
Speaker 1: really tight message, like who am I from the perspective
Speaker 1: of someone that I would want to like me.
Speaker 2: Welcome back to On the Job Today, we're speaking with
Speaker 2: Grace Lee, a professional dating coach based in New York City.
Speaker 1: My business is called a Good First Date, and we
Speaker 1: started in twenty eighteen, and I work with men and
Speaker 1: women of all ages and situations on every aspect of dating,
Speaker 1: with my primary focus being online dating, how to optimize
Speaker 1: that your dating apps and everything that comes after that.
Speaker 2: Now, before you go thinking we've changed the format over
Speaker 2: here and On the Job, Grace and I are talking
Speaker 2: about much more than just dating on today's episode. Beyond
Speaker 2: learning what it means to be a professional dating coach,
Speaker 2: we'll uncover the surprising similarities between our romantic and professional lives.
Speaker 2: So even if you're happily hitched or dead set on
Speaker 2: staying single, stick around to get some valuable advice from
Speaker 2: this dating pro Being a dating coach was not something
Speaker 2: Grace Lee set out to do.
Speaker 1: I actually started working in corporate banking, and then when
Speaker 1: my daughter turned one, I left the bank completely. I
Speaker 1: opened a boutique in Shanghai, and then I sold children's things.
Speaker 1: It was really that great thing that happens when you
Speaker 1: are obsessed and love something and then suddenly it's your
Speaker 1: job and you get to do it all the time.
Speaker 2: On paper, everything was going well for Grace. She had
Speaker 2: a diploma from a good school, a successful career, a husband, kids,
Speaker 2: all the pillars of a thriving life. But in two thousand,
Speaker 2: in a nine, Grace's life took an unexpected turn with
Speaker 2: a divorce and a move to New York City. And
Speaker 2: that transition period was as challenging as you'd imagine.
Speaker 1: I got married when I was twenty six, and before
Speaker 1: then was pretty much a serial monogamous, so I had
Speaker 1: never really dated. And since I got married kind of young,
Speaker 1: I'd never had that experience of just being single and
Speaker 1: living that single person's life.
Speaker 2: But now there she was, thrust into a big, new
Speaker 2: city and this unfamiliar phase of life.
Speaker 1: I remember the first date I went on after I
Speaker 1: got separated. Couldn't believe how intense it was emotionally. It
Speaker 1: was like the whole, like the whole box of crayons,
Speaker 1: like every single emotion, from being completely obsessed and fixated
Speaker 1: to feeling like totally tragic, like nothing ever good will
Speaker 1: ever happen to me again.
Speaker 2: In time, though, the intensity of those emotions settled down
Speaker 2: and Grace started doing enjoy the process of going on dates.
Speaker 2: They offered her a healthy relief from the shakeup of
Speaker 2: the divorce and then responsibilities of single parenting.
Speaker 1: So when I moved to New York City, I had
Speaker 1: two little kids and mash dot com was just starting
Speaker 1: to get fired up, so I took the opportunity, was
Speaker 1: really curious and leaned heavily on match and just started
Speaker 1: dating a ton.
Speaker 2: Dates were also a great way for Grace to explore
Speaker 2: her new hometown and engage with people she'd never have
Speaker 2: met in the finance world.
Speaker 1: Being a parent, like having little kids, and also I
Speaker 1: was working in banking at the time, so that was
Speaker 1: my circle. And then suddenly with online dating, I could
Speaker 1: match someone from a completely different world, and I loved
Speaker 1: I loved the experience of just sitting down with someone
Speaker 1: and imagining myself in their childhood and what they did.
Speaker 1: It's kind of how also how I discovered different parts
Speaker 1: of the city, and it just really opened my mind
Speaker 1: to life outside of being a banker and having little.
Speaker 2: Kids were once the idea of having to go out
Speaker 2: into the dating world seemed overwhelming and intimidating. Soon Grace
Speaker 2: couldn't wait for her next date.
Speaker 1: I think because I was fresh out of a divorce
Speaker 1: and I didn't have any experience. I really went in
Speaker 1: full force and dated many, many people. You know, I
Speaker 1: was one of these people that might have gone on
Speaker 1: three or four dates a week.
Speaker 2: And being the organized professional type, Grace even made a
Speaker 2: spreadsheet to keep track of her potential suitors. Do you
Speaker 2: remember what some of those columns might have looked like?
Speaker 1: Sure, I mean there were basic ones, you know, age,
Speaker 1: I profession, something about it was fun to talk to them,
Speaker 1: might have been like a personality score, what they did
Speaker 1: for work, how much money they had, what neighborhood they
Speaker 1: lived in. I'm not proud to admit that, but that
Speaker 1: was definitely on the spreadsheet, just like it is in
Speaker 1: a database for any matchmaking service. And there's probably an
Speaker 1: attractiveness rating that fell outside of age and height, just
Speaker 1: if I was attracting them or not.
Speaker 2: And while Grace was doing fine on match dot com,
Speaker 2: She also put her name on one of those professional
Speaker 2: matchmaking databases and shortly thereafter gets invited in to fill
Speaker 2: out a questionnaire.
Speaker 1: They were asking me all kinds of questions and doing
Speaker 1: it in a very serious way, like why are you
Speaker 1: still single? What are you looking for? It was on
Speaker 1: your red flag list? All of these questions that are
Speaker 1: actually so fun to answer, and all of this information
Speaker 1: is there to help them match people well.
Speaker 2: And Grace found this whole process fascinating.
Speaker 1: So I remember during that interview looking at her and
Speaker 1: asking her if this was a real job, because I
Speaker 1: couldn't believe that this was someone's profession. And long story short,
Speaker 1: I was never match with that client, but I ended
Speaker 1: up working as a matchmaker.
Speaker 2: And initially Grace loved matchmaking, especially compared to banking.
Speaker 1: Speaking about the differences between matchmaking and working in Kaindance.
Speaker 1: The Monday morning meeting for matchmaking is hilarious. It's a
Speaker 1: bunch of matchmakers talking about their clients, talking about people
Speaker 1: in the database. Do you think that this person would
Speaker 1: go all with this person? So it was like getting
Speaker 1: paid to gossip, but of course in a very professional,
Speaker 1: purposeful way.
Speaker 2: But while Grace really enjoyed meeting her clients and helping
Speaker 2: them in their romantic journey. She found the particulars of
Speaker 2: matchmaking less than ideal. Well, not to mention, from her
Speaker 2: own dating experience, she knew that the dating apps, which
Speaker 2: were really gaining in popularity at this time, did a
Speaker 2: pretty good job of connecting people. That is, if you
Speaker 2: knew how to make an effective profile.
Speaker 1: I realized, like, I can help people get on a
Speaker 1: good first I'm very, very good at getting people on
Speaker 1: a good first date.
Speaker 2: So that's when Grace pivoted from being a professional matchmaker
Speaker 2: to a professional dating coach.
Speaker 1: There's a lot of work that goes into helping clients
Speaker 1: come up with their profile. It's intensely creative personal work.
Speaker 1: So it's really a matter of figuring out how to
Speaker 1: help people make their profile more like them, to be
Speaker 1: a better representation of them, and then also to teach
Speaker 1: them how to swipe and text so that they can
Speaker 1: filter people out and go on the days that they
Speaker 1: want to go on.
Speaker 2: To do this, Grace meets with her clients one on
Speaker 2: one and tries to get to the core of who
Speaker 2: they are.
Speaker 1: I'm always scanning for those things that are going to
Speaker 1: make them stand out because they're in a pile of
Speaker 1: thousands of people and they have a moment to make
Speaker 1: an impression, and then how do you present that. It's tricky.
Speaker 2: And while it might be tricky to boil someone down
Speaker 2: to a limited amount of text and a few pictures,
Speaker 2: when it does happen, Grace will tell you it feels
Speaker 2: better than banking. Ever. Did I love it?
Speaker 1: When we come out on the other end and we
Speaker 1: have it. When we nail the thing, it's like, Oh,
Speaker 1: feels so good, like we got it. Then the person
Speaker 1: forget the date, they're looking at the profile and they're like, Wow,
Speaker 1: I'm actually a pretty interesting person.
Speaker 2: In this way, Grace is helping people take stock of
Speaker 2: their lives to highlight what makes them unique, capturing their personality,
Speaker 2: and celebrating their achievements, and then to present all that
Speaker 2: to the world with the hope of catching someone's attention,
Speaker 2: which sounds pretty similar to sending out resumes and cover letters,
Speaker 2: doesn't it. So when we come back from the break,
Speaker 2: we'll explore the many parallels between online dating and our
Speaker 2: increasingly digital business world, and maybe we'll get Grace Lee
Speaker 2: to help us present our best selves, whether that's to
Speaker 2: a potential partner or our next employer.
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Speaker 2: We're back with professional dating coach Grace Lee. Through her
Speaker 2: service A Good First Date, Grace helps people put their
Speaker 2: best foot forward on dating apps and other online dating platforms.
Speaker 2: But it's not just our love lives that have gone digital.
Speaker 2: Job applications are submitted online, meetings happen over zoom, and
Speaker 2: most of our work communication these days runs through email
Speaker 2: or Slack. These shifts have revolutionized how we work, but
Speaker 2: they've also introduced some challenges, because anytime we translate ourselves
Speaker 2: into a digital format, there's a risk that something gets
Speaker 2: lost in translation, and that risk starts with our most
Speaker 2: essential documents.
Speaker 1: I think in a CV it's a little bit less esoteric.
Speaker 1: There is more standard ways of presenting yourself, so it's
Speaker 1: like kind of have to figure out those key things
Speaker 1: about yourself, how do you want to talk about them?
Speaker 1: And if you can take your ego out of it,
Speaker 1: you can start to think more carefully about how you're
Speaker 1: presenting yourself.
Speaker 2: As you all learned in a previous episode this season,
Speaker 2: a lot of our online job applications are first reviewed
Speaker 2: by AI, so yes, you need to have all the
Speaker 2: pertinent information in there, but eventually, hopefully your CV will
Speaker 2: reach human eyes. And just like with a dating profile,
Speaker 2: you want your CV and cover letter to catch that
Speaker 2: person's attention with clear and gauging messaging.
Speaker 1: So just thinking about, Okay, the other person is sitting
Speaker 1: there with your CV, they have a checklist of things
Speaker 1: that they're trying to tick off to move you to
Speaker 1: the next round. They're not invested in whether or not
Speaker 1: you get.
Speaker 2: The job or not.
Speaker 1: They kind of want you to because they don't want
Speaker 1: to keep doing this thing. They just want to find
Speaker 1: the person already.
Speaker 2: And while it might be tempting to make one resume
Speaker 2: and send it out to every job, Grace recommends customizing
Speaker 2: your messaging to the job you're seeking.
Speaker 1: In that case, it's going to be about highlighting what
Speaker 1: was interesting about your job. So if you're going into
Speaker 1: the hospitality industry, that job that you had over the
Speaker 1: summer serving coffee is actually going to be more relevant
Speaker 1: than your private equity job.
Speaker 2: And this isn't a send it and forget it sort
Speaker 2: of thing either. Just as Grace made a spreadsheet to
Speaker 2: keep track of our dates, as job applicants, we need
Speaker 2: to reflect on the responses our applications get. We need
Speaker 2: to ask ourselves what's working, what isn't, and then fine
Speaker 2: tune our messaging based on that feedback.
Speaker 1: Yeah, it's like I can't believe I didn't get invited
Speaker 1: to any first round interviews for banking. I can't believe it,
Speaker 1: and then just being curious about it, like, oh, I
Speaker 1: wonder why not. Maybe there's a good reason.
Speaker 2: Eventually, though, if you get through those early rounds, you'll
Speaker 2: be asked in for an interview, and Grace says interviews
Speaker 2: bear an uncanny resemblance to a first date, despite the formalities.
Speaker 2: It's just two people trying to get to know one another.
Speaker 1: So for every single thing you have on your CV,
Speaker 1: have a story, and that story should be about how
Speaker 1: what you did makes you qualify for this job, and
Speaker 1: that story should just be interesting and fun, one that
Speaker 1: you enjoy telling, so that you have a good conversation.
Speaker 2: So in the same way you might highlight your love
Speaker 2: of live music on your dating profile. Grace suggests coming
Speaker 2: into the interview with a strategy to move the conversation
Speaker 2: in a purposeful direction.
Speaker 1: Let's say you're going to an interview and you really
Speaker 1: want to learn about AI. That's something that you want
Speaker 1: to do in your career. So you want the conversation
Speaker 1: on the interview to touch AI at some point, and
Speaker 1: you want it to be pretty central, so that you
Speaker 1: can talk about the things that you've done on your
Speaker 1: own and you can analogize how those skills might help
Speaker 1: a company like theirs. Even if the job that they're
Speaker 1: trying to interview you for may not be an exact fit.
Speaker 1: Now they've seen you and they said, oh, this person
Speaker 1: is really interesting and they've brought all this experience in AI.
Speaker 1: So even if my department isn't looking for it, maybe
Speaker 1: this is a candidate that would be good for this
Speaker 1: other department.
Speaker 2: And we should also remember that the interview is a
Speaker 2: two way street.
Speaker 1: You can show them that you're interested in a lot
Speaker 1: of ways by being attentive by being interested in their story,
Speaker 1: by sharing things about yourself that you want them to know,
Speaker 1: and then you have to let them meet you half
Speaker 1: way too. I would try to touch on a lot
Speaker 1: of different topic until I found the one that I
Speaker 1: thought they were comfortable with. Then they can bring themselves
Speaker 1: out and that's when you can test real compatibility.
Speaker 2: That same advice still applies after you get the job,
Speaker 2: or even if you've had the same job for decades,
Speaker 2: because at the end of the day, no matter what
Speaker 2: we do for work or how long we've been doing it,
Speaker 2: our professional lives revolve around interpersonal relationships. As Warren Buffett said,
Speaker 2: partnership is not a legal contract between two equal individuals.
Speaker 2: It's an emotional alliance between two people who are committed
Speaker 2: to each other's success.
Speaker 1: The number one thing you need in any situation, job, romance,
Speaker 1: friendships is mutual interest. And when we don't have that,
Speaker 1: things like point fall apart.
Speaker 2: And speaking of falling apart, since we're talking about relationships
Speaker 2: of all sorts here, it'd be wrong not to acknowledge
Speaker 2: that sometimes they break down, that our passions wane, or
Speaker 2: a job just run its course. That isn't to say
Speaker 2: we should all be quick to jump ship and run
Speaker 2: to the next new thing. Lasting rewarding relationships take work
Speaker 2: and commitment, but if that time comes grace. Lee has
Speaker 2: learned from personal experience that sometimes starting a new is
Speaker 2: just what we need.
Speaker 1: I love getting to know my clients, and I love
Speaker 1: watching them have these breakthrough moments where they come to
Speaker 1: me and they're so worried about something, and those moments
Speaker 1: where I can just reassure them that they're doing fine. Yeah.
Speaker 1: I want people to feel good about their lives and
Speaker 1: optimistic about what could happen, and confident that they're doing
Speaker 1: everything they can to find the person they want to
Speaker 1: be with.
Speaker 2: For on the job, I'm Avery Thompson