Starting a Company, Death to The Cover Letter, and Getting Hired with Bridget Flaherty

Bridget Flaherty is the Senior Talent Director at Fractal Software, which is a venture studio launching the next generation of vertical SaaS startups. Before going into talent, Bridget worked at the Jesuit Volunteer Corps. We talk about being a founder, women in the space, and how to get hired: all things applying, interviewing, and creating a cover letter.

Reach out to Bridget here: LinkedIn

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Transcript

Claire Calfo:
Hi Bridgette, welcome

Bridget Flaherty (she/her):
Hello.

Claire Calfo:
to What Your Mom Forgot to Tell You.

Bridget Flaherty (she/her):
Thank you. I'm so excited to be here. I feel like

Claire Calfo:
I'm

Bridget Flaherty (she/her):
it's

Claire Calfo:
so

Bridget Flaherty (she/her):
been a

Claire Calfo:
excited.

Bridget Flaherty (she/her):
long time coming.

Claire Calfo:
I know, I'm so excited that you're here. I just feel like we have such important and cool things to talk about. So I'm excited for everyone who's gonna listen to this, especially like people graduating from college and anyone who's like lost their job recently, I feel like can really benefit from what we're gonna talk about.

Bridget Flaherty (she/her):
Yeah, definitely a good time, I feel like, given everything that's going on, but also just, it's always important to think about kind of career stuff, even if you're super content in what you're doing, I think always important to kind of be retrospective about what you're doing and what you want to be doing and how you can get there in the most effective way. So I'm pumped, really

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
pumped to have the conclusion.

Claire Calfo:
absolutely. Before we get into all the juicy stuff, would love for you to just give everyone a background on you, like how you got to where you are today. You're the Senior Talent Director at Fractal Software, which is such a hefty and amazing title. So would love to hear how you got to that place and sort of those jumps you maybe made to get where you are today.

Bridget Flaherty (she/her):
Yeah, absolutely. Yeah. I mean, who would have thought that like five years ago, even three years ago, this would be what I would be doing. And sometimes I think about it every day and like who would have thought, but I'm happy where I am. Um,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
but yeah, a little bit of the background. I kind of taking like maybe 13 steps back. I grew up in Wisconsin, um, always had a dream of kind of wanting to go. To college in California, thought it was like this visionary type of thing, like different than Wisconsin. I'll go out and learn a bunch on the West coast and figure out what's next. But. went to school there and I think the first, my first foray as I call it into recruiting was, I was a tour guide at Santa Clara University where I went to school. And I found that job just to kind of have an on-campus job, get some money while going to school. And we really were kind of trying to recruit a lot of different students and people to come to the university that I was at. So I always think of it as being kind of the first recruiting gig that I had in my career. We were selling people on this like very expensive education one that would like change

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
the course of. their life after that. And so I thought it was an interesting kind of ability to get to know people, what was important to them, their priorities, and what encouraged them to at the end of the day come to Santa Clara or a different school. So I did that, loved it, loved the people aspect during college. Like I find myself to be a very big people person. Like sometimes I feel like I'm a little bit of an introvert knowing that I need to like have time to recharge. But in terms of my day to day, like I always want to be working with people. I don't think

Claire Calfo:
Mm-hmm

Bridget Flaherty (she/her):
I could be someone that just is sitting behind my computer or not. interfacing with either clients or customers or candidates in this case. So I did that during college and then I decided to do a year of service through the Jesuit Volunteer Corps, which is similar to like AmeriCorps or Peace Corps in a way. But I did that in Syracuse and I was actually working in volunteer recruitment for an HIV clinic. So working with folks that were like required to do community service to corporate level volunteers, really encouraging them to come volunteer for like our AIDS Walk, Run, or like just general kind of tasks that we needed to do around the clinic. It was a very different type of recruiting, but similar themes, and that I really liked, you know, working with different populations, especially in that case, kind of bringing groups of people together around causes that they were passionate about and cared about. And so that was a year-long contract. But at the end of that, I was like, what the heck am I going to do now? Like, I have no idea. I was very lost. I think having even like a deadline where I knew

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I had to like make a change made it a lot harder. to start thinking about

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
that when I probably started, what we should have started thinking about that. So that time kind of approached, I knew I wanted to be in New York City. And I think that is one thing that I think is important for folks that are like going out to find a next role is like anchoring around at least a couple locations, or if you want to be remote first and like choosing that you want to be remote first, because it kind of just like narrows

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
your search a little bit in a way that I think is productive versus just throwing things out the wall and seeing what sticks.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And so I chose New York. That was the place I wanted to go. And I found, I was applying to a bunch of stuff from nonprofits to tech jobs and just really all over just to see kind of who wanted me and what like piqued my interest once I started talking to the folks at the company. And I ended up going on to Built-in New York which I highly recommend for anybody that is trying to

Claire Calfo:
Gosh.

Bridget Flaherty (she/her):
find a job in tech, have you used it?

Claire Calfo:
Oh, I found all my jobs on Built in LA. So,

Bridget Flaherty (she/her):
It's just like the best. I mean,

Claire Calfo:
except for

Bridget Flaherty (she/her):
it's

Claire Calfo:
the last one.

Bridget Flaherty (she/her):
such

Claire Calfo:
Yeah, it's the best.

Bridget Flaherty (she/her):
a valuable

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
resource. And it's like, they curate all of these lists of top tech companies, best culture, like best workplaces, and they

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
have them for like New York and San Francisco and Chicago all over, but it's called Built in New York. And so I was on there and I found a junior recruiter role at a company called Leaf Link, which is a B2B marketplace in the cannabis space. They're essentially kind of like, if I was a dispensary, I would go on to Leaf Link to choose the brands that I would want. want to sell in my store. So it was a tech company, but kind of playing in this new budding industry, forgive my pun. But they, thank you,

Claire Calfo:
Good one.

Bridget Flaherty (she/her):
they brought me on to kind of scale between the series B and the C. So I was about 35 people when I joined. And then when I left, it was about like 120, 125. So there was a lot of growth in that year and a half. I was hiring across like product and engineering to data to marketing, finance, I was a sole recruiter during a period of time there. So it was really, really a good growth opportunity. to learn about different roles within a company. I always recommend to people if you don't know what you wanna do, starting a recruiting can actually be a really good foray into understanding what you wanna do. Could

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
you?

Claire Calfo:
you like understand the day to day of each person's job when you do that too.

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Yeah. And you work with the different hiring managers and see you understand their priorities. And it gives you this exposure to a lot of different functions that I think can sometimes go like unnoticed about that HR department in a way. So I joined there, I spent the time there. I loved the company. It was a great first job to be able to have within the tech scene. And then I was approached by this opportunity at Fractal where I met now, back when they were very, very nascent and just kind of I was very new to this venture studio concept, and I think a lot of people have been learning a lot about ways to launch a company. The last

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
couple of years, entrepreneurship has become something that more people talk about and want to experience. Basically what Fractal does is kind of accelerate and de-risk the opportunity for entrepreneurship for folks both on the operating side and engineering side that want to build a software company. So we focus within vertical SAS, which is really software for a very specific industry, whether that be golf courses or pest control businesses or physical therapy clinics, like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
very agnostic in terms of industry, but just building out software for these spaces that have really not had technology previously, or at least

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
have had bismole software. So what my team does now is we essentially go out and re-recruit for the founders of these companies that we invest in. So we look for CEOs and CTOs that we'll give a million dollars to and allow them to go out and build these software businesses. So we act as kind of investor, but also kind of incubate the businesses through diligence and the ideas and the people that end up becoming the founders. So it's a very different type of recruiting, but it's been awesome. And now I oversee the team of both recruiters and sourcers that go out to find our founders. So sorry that

Claire Calfo:
That's

Bridget Flaherty (she/her):
was long, but hopefully it's helpful. Ha

Claire Calfo:
no,

Bridget Flaherty (she/her):
ha.

Claire Calfo:
I mean, I would hire you if I got that three minute pinch. So

Bridget Flaherty (she/her):
Oh, there we go. You always

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
got to have your elevator pitch as a recruiter.

Claire Calfo:
yeah, that's

Bridget Flaherty (she/her):
Ha

Claire Calfo:
a

Bridget Flaherty (she/her):
ha.

Claire Calfo:
good one. I love how you went all the way back to it's always nice to see how people's like paths align eventually at some point. So that's, that's very

Bridget Flaherty (she/her):
Totally.

Claire Calfo:
cool. Yeah.

Bridget Flaherty (she/her):
Yeah, I think whenever you're thinking about what you want to do, thinking back to what interests you, even when you were in high school or middle school,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
or even younger than that, I think is an important exercise.

Claire Calfo:
Totally, like the skills that have gotten you where you are. Like even if it's like touring people and like telling

Bridget Flaherty (she/her):
Cool.

Claire Calfo:
them, like selling, you could have even done sales if you think about it.

Bridget Flaherty (she/her):
I think, I mean, like recruiting and sales is like a Venn diagram

Claire Calfo:
So

Bridget Flaherty (she/her):
in

Claire Calfo:
similar,

Bridget Flaherty (she/her):
my mind.

Claire Calfo:
yeah.

Bridget Flaherty (she/her):
It's so similar. And like,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
you know, like sometimes though, like salespeople don't want to be called recruiters and recruiters don't want to be called salespeople.

Claire Calfo:
That's

Bridget Flaherty (she/her):
Like there's

Claire Calfo:
true.

Bridget Flaherty (she/her):
like that kind of dynamic maybe,

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
but

Claire Calfo:
that's

Bridget Flaherty (she/her):
they're

Claire Calfo:
true.

Bridget Flaherty (she/her):
definitely more similar than, than you think. I mean, you're selling people on a vision of a company and the product in some cases, the leaders.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And so it's definitely inches a little bit more closely to sales than some might imagine.

Claire Calfo:
Yeah, 100%. This is kind of an interesting question that just popped up, but I went to South by Southwest this year and one of the talks I went to was titled, by 2030, half of the workforce is going to be a CEO. Do you think that is true or what is your thought, especially working in industry where you are constantly recruiting founders and finding those gaps in the market? Do you think that's harmful or helpful kind of in a way?

Bridget Flaherty (she/her):
I love this question and I wish I was there to have seen the talk. I want to go to South by Southwest at some point, but I would love if it was 50% by that day. Like

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think it's trending that direction. I think in general, more people should want to be their own boss and work for themselves. And I think it's good for our economy more broadly.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I think it's definitely inching up. If I had to bet, it probably won't be at about half but maybe close. And I think there's been this like realization the last five years, at least in my opinion, and the people that I've spoken with, that there are a lot of employees that have just felt a little bit trapped, I think, by

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
either the golden handcuffs of equity in a company or even just believing that they need to gain X, Y, and Z experience before taking that plunge and maybe doing something on their own. But I think that with venture studios and accelerators, like Y Combinator and like...

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
You know, even just venture capital firms that have been more willing to bring people into like entrepreneur and residence programs, they've

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
lowered these barriers to entry that I think have been so prevalent, you know, historically in being able

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
to launch a business, whether that be not having an idea, you know, not having a co-founder, not having access to capital, especially for underrepresented groups, which I think

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
is something that, you know, we focus on a lot, but I think has just been ignored a lot historically.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
been these institutions that have put a priority on lowering those barriers to entry or removing them entirely that I think has allowed a lot of people to get or become like, untrapped from these institutions that they're in.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
So I think that's includes the numbers. And I think there's also just like this aspect of our society viewing entrepreneurship in a very positive lens.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Even if you go out and you do something on your own, you build your own company for a year or two years and it fails. you've got such amazing experience that

Claire Calfo:
So true.

Bridget Flaherty (she/her):
almost any other company that you interview with is going to view in a positive way.

Claire Calfo:
Yeah, yeah, you pretty much did every job that you could possibly do also.

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
If you're

Bridget Flaherty (she/her):
exactly.

Claire Calfo:
starting,

Bridget Flaherty (she/her):
And so

Claire Calfo:
yeah.

Bridget Flaherty (she/her):
you can, it's a good pivot point too, right? Or if you're like, I'm going to try

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
something, then maybe I'm going to do something completely different after, like it gives you that

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
breathing room to understand what that might be.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
But I also think there's like a healthy chip on people's shoulder almost too, or it's like, you've probably worked for a boss. I know I've, you know, definitely worked for bosses in the past, that you probably would want to do something a different way, or like the CEO

Claire Calfo:
100%.

Bridget Flaherty (she/her):
of your company, like they make a decision, you're like, you know what, I probably would have gone a different route with that. And I think

Claire Calfo:
100%.

Bridget Flaherty (she/her):
that's like a healthy tension to have, like where it just motivates you to wanna like go out and do it on your own.

Claire Calfo:
Yeah, 100%. I so agree with that. I think the closer you are working for startups like we have versus working for those larger corporations, you have such a unique eye into how operations work and how people make decisions. It gives you that assertiveness. I don't know, I, when I first got into tech, kind of just did whatever the bosses said. Then I think as I stayed in the industry, I'm allowed to disagree and people want me to disagree. And then if it doesn't go the way you want, then that's okay. But it's good to speak up and observe those things. So,

Bridget Flaherty (she/her):
Absolutely. And it's all like learning experiences

Claire Calfo:
yeah.

Bridget Flaherty (she/her):
too. And nine times out of 10, like when you do, you know, kind of push the boundaries, try to change the narrative a little bit, it's going to be appreciated.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And if it's not, you're probably not in the right environment in the first place.

Claire Calfo:
So true.

Bridget Flaherty (she/her):
And so

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
it's a good thing to like, as you're in an interview process, like understand

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
the way that they like gather feedback and like, you know, allow for pushback, healthy pushback and conversations. But, but I don't know, I think like not to make it, I mean, I actually know, I'm not even gonna say sorry about that, but like to make it a woman focused thing too, where it's like,

Claire Calfo:
Yeah, I was gonna

Bridget Flaherty (she/her):
I never

Claire Calfo:
ask about

Bridget Flaherty (she/her):
thought

Claire Calfo:
this.

Bridget Flaherty (she/her):
that I would want to be, yeah, like I'll just get ahead of it and bring

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
it up in

Claire Calfo:
perfect.

Bridget Flaherty (she/her):
the first place. Like I never would have thought about starting my own company

Claire Calfo:
Mm hmm.

Bridget Flaherty (she/her):
before I started at Fractal, like it never

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
even crossed my mind. Like, and now I think, seeing obviously the way that they support these people launching, but also just like, talking to people that are the same age as us, that have done

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
this and that are loving it, and they don't wanna ever do anything else. It makes it so much more achievable, which is why I think it's so important to see people that look like you in

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
these roles and get close to them and understand what they do. To understand it's not something that's so untouchable. Being a CEO

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
is not something that's unachievable for people.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
There's probably a lot of CEOs out there that are not doing the greatest job, but they're still probably making a good amount of money. And

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
so it's like, you might

Claire Calfo:
so

Bridget Flaherty (she/her):
as

Claire Calfo:
true.

Bridget Flaherty (she/her):
well just give your own shot at it.

Claire Calfo:
A hundred percent. Yeah. I, I so agree with that. I think until I heard about your company, I was like, Oh, like anyone can be a founder if they really like, there are resources now that there weren't like even five years ago, probably. And yeah, yeah. So I guess

Bridget Flaherty (she/her):
I mean, like.

Claire Calfo:
one question I have too, like in the women, like people of color too, like there really aren't that many. You know, BIPOC women CEOs and like you really see a majority of white males in those roles. And I think that's harmful in a way because a lot of, it's a lot of the time like the way we progress as a country and like as you know, together is like different ways of thinking and different like ideas and perspectives. So I'm like curious, have you've come across that in your job and like how you've like dealt with like maybe like encouraging diversity and how people can do that maybe in their job too.

Bridget Flaherty (she/her):
Yeah, absolutely. I remember when I was going through the process at Fractal, my interview process, which I think is, if it's important to you, it's always something you should ask about when interviewing

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
is like, you know, what are the priorities and what are the values of the organization around DEI, but also like, what are you doing? Like, what are you actively doing to kind of change the narrative or change the statistics? And I think for my job, it was like twofold. Like one, I want to understand what the internal team, obviously that I'd be interfacing with day to day would look like, but also. Like what are our priorities or values in terms of the portfolio of these founders

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
that we're recruiting? And I think right now, Workbench, which is an awesome organization that pulls together these, they're VC, but they pull together a lot of reports on diversity within tech specifically. And

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I think the stat was last year, it's like 2% of founders in enterprise software are women. Like 2%. Like

Claire Calfo:
Wow, that's shocking.

Bridget Flaherty (she/her):
shocking. Like think

Claire Calfo:
Oh,

Bridget Flaherty (she/her):
about

Claire Calfo:
that's so

Bridget Flaherty (she/her):
the split,

Claire Calfo:
sad.

Bridget Flaherty (she/her):
the gender split. It's so sad. And I'm like,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
It's unbelievable then that on the flip side of that, like female founded companies have like an unbelievably higher chance of success

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
than male dominated companies around companies. And so, and venture capitalists are super eager now, at least to be able to like invest in these people. But

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
it's again, like coming back to the barriers of entry, barriers to entry for these folks to be able to understand that A, like they can do it, that's where imposter syndrome comes in, but B, like. you know, there are organizations that have the resources to be able to make sure that they can do it successfully.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
We think within our portfolio, like I know like all of the female founders get like such incredible feedback. And I think

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
there's a lot of hurdles that naturally like underrepresented groups have to get over in any job,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
let alone being under, especially sometimes in like male dominated industries or white dominated industries. Like there's the industry component too that comes into play when it comes to the success of an organization or that person.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
But I think like you've nailed on the head, like different perspectives and different leadership. Like it's not only them being in the founder seats, but think about the people that they'll hire and like the impact

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
that they'll make companies that they're building.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
Like they could be another unicorn or like public company that has, you know, 75% of their engineering team. That's, you know, people of color, for example. And so

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think it's it's the ripple effects there are something that will serve our entire ecosystem a lot better. But it starts with people willing to take the bet. and go out of their way to find individuals from underrepresented groups. Because the easy thing is, across my desk, in terms of the applications we're getting,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
90% of them, if not higher, are a very specific archetype of person who maybe

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
went to a big consulting firm, a private equity firm, and then is in an operating role at a tech company.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Their LinkedIn's are almost identical.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And so

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
you've got to put in the work to find these people.

Claire Calfo:
100%. And there's different leading styles too. Like if everyone comes from a big four, they're taught a certain way of management and that might not be the best way of the future. Like you never really know. I don't know, those different backgrounds have different management styles, I'm

Bridget Flaherty (she/her):
Yes.

Claire Calfo:
sure.

Bridget Flaherty (she/her):
And

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think about it too, and this is something that my team talks about a lot, where it's like, a lot of people that grow up through these bigger and well-known institutions, like, there's a lot of people that pave their way for them, don't get me wrong, but there's

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
also a lot of people that are handed a lot of these opportunities, just due to the nature of the people that they've surrounded themselves with.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And so I often think the person that has that gritty drive to be able to like, you know, maybe have gone to not a top 100 school and like made it to an awesome company, progressed through that company, like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
has clearly had impact and has you know, really gotten over these barriers themselves in such an intentional way. Like, they'll probably have a higher chance of success because they've gone through these hurdles before.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
But it's not to say it's not wrong in the first place that they're there, but it's just kind of the statement or the

Claire Calfo:
And they're

Bridget Flaherty (she/her):
matter

Claire Calfo:
working

Bridget Flaherty (she/her):
of fact.

Claire Calfo:
hard because there's not like a fallback really. It's like, I'm working hard because I like want to, and I have to. So.

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Yeah. So I think and being a founder is not easy. It's very lonely.

Claire Calfo:
No.

Bridget Flaherty (she/her):
I mean, I haven't done myself so I can't say that but from what I've heard, it's lonely. It's hard, obviously hard to only have you and sometimes a co-founder to talk about certain things with and so you don't want to just give up when the going gets tough. Like you want someone that's going to be persistent through that.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Um, because sometimes the past experience can shed a lot of light on that.

Claire Calfo:
Yeah, speaking of that, just having that grittiness, like you mentioned, what if someone listening to this is thinking about, I do want to start my own thing, whether that is a tech company or even just something on their own, like you mentioned earlier, wanting to be their own boss. What kind of skills, and these are obviously things people can learn too, not just like, we're not inherently good at these things, but yeah, what do you think separates themselves from a good founder, and I don't want to say bad founder, but like... the person who really gets further and has a great team and has a good relationship with their team, let's say.

Bridget Flaherty (she/her):
I think, you know, getting down to like technical stuff, it obviously would depend on the industry and the product of what they're building. And I will say, like, I do think there is a myth out there that you have to be like super familiar with whatever industry you're building in in order to be successful. Like, I don't think that's true. Like,

Claire Calfo:
I

Bridget Flaherty (she/her):
this

Claire Calfo:
agree.

Bridget Flaherty (she/her):
is my personal perspective. Like, I think it's often great to have someone who's not familiar with an industry, like go into a new space, bring their skillset and be able to like define or disrupt whatever

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
is happening within that. opportunity. And so that aside, I don't think you have to have the industry experience to be successful. I do think in any job, no matter any founder job, no matter what you're building or what you're trying to do as a business, sales is a big piece of it. And that

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
comes in a lot of forms. I think being able to sell early hires on your vision when maybe there's no product built or there's no traction or there's no revenue or whatever it might be, being able to be someone who can share. what is exciting you about that opportunity with obviously people that you might hire, but then also in turn, like investors as

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
well as potential customers is hugely important. And I think something that you don't have to have been like a salesperson in your career

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
to be successful, but I think having that drive and that hunger to be willing to pick up the call or pick up the phone 100 times a day to make a call to a potential customer or be willing to travel across the country. country to go to like a trade show to meet

Claire Calfo:
Right.

Bridget Flaherty (she/her):
people that may be using your software or your products. And so I think being able to put yourself out there a little bit and sometimes an uncomfortable way to be able to make those connections and not be afraid to network, I think is a huge advantage and will kind of set you aside from maybe other people that are not putting in that sort of effort.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I also think like having, as it relates to hiring, which usually companies will do and no matter what stage you're at. Like having a good understanding of like what sort of team you want to build. Um, you know, I, I've worked with founders who are totally fine having a remote workplace. I've worked with founders who like want to have everybody in the office, you know,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
five days a week have that sort of environment. Like it sounds silly, but it's also something that I think is important, especially when you're, you're deciding to work with like a co-founder, for example, like

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
making sure that you're very aligned in the way that you want to build the company, um, I think is, is really important. And then I also think like. the timing and the acceleration piece is one too, like, or let me put that better, urgency. And like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
when you have a lack of urgency, I think that's when a company can suffer

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
and really being urgent and operating with velocity at like everything that you do, especially in the early days, like 15% of companies or something like that, like make it from their first point of fundraising to the next point of fundraising, like that's a very small amount. And so like... The faster

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
you can do things, the faster you can gain traction. Like that will give you a better advantage when it comes to raising more money. Um, if it's a venture backed business in this case, obviously there's a lot of types of businesses, but I think that's true of anything, any company that you're building, like doing it with urgency, um, and with intention, I think will

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
set you apart from other people. Last thing I'll say, and sorry, I'm going on here a little bit, but last thing I say is like the narrative that you have, which goes

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
to the sales a little bit. But even if you haven't worked in this industry, like being able to share with someone like why you personally are building this business

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
will go a long way.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Whatever it is, if you're selling dentist software, sharing a story about a dentist experience that you have maybe had that encouraged

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
you to want to build in that space.

Claire Calfo:
Like connect with people's emotions almost, I think, is like a big thing.

Bridget Flaherty (she/her):
Yeah, and like,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
you know, within I think there's a set out there that's like venture capital firms and probably many investors, they'll make their decision on whether they want to give you money within like the first two minutes of you meeting them.

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
Like the first question

Claire Calfo:
that's

Bridget Flaherty (she/her):
thing

Claire Calfo:
crazy.

Bridget Flaherty (she/her):
is like super huge, which like I could probably disagree with some of the philosophies behind that. But

Claire Calfo:
Yeah, there might be some gaps

Bridget Flaherty (she/her):
yeah,

Claire Calfo:
there.

Bridget Flaherty (she/her):
might be some gaps there.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
But

Claire Calfo:
Yeah. Yeah.

Bridget Flaherty (she/her):
anyway, something to think about.

Claire Calfo:
I love it. I kind of want to get into hiring a bit.

Bridget Flaherty (she/her):
Woo!

Claire Calfo:
And like sort of your experience, obviously, like you did recruiting for so long, and you still do it. What do you think? I think I'm going to start maybe just like with this one general thing and then we can go deep into other areas. But do you think a cover letter is important?

Bridget Flaherty (she/her):
I hate cover letters. I literally despise them.

Claire Calfo:
Thank God. I I

Bridget Flaherty (she/her):
Would you have like

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
hung up the call if I had said yes?

Claire Calfo:
I would have laughed and I would have never released this episode.

Bridget Flaherty (she/her):
No, yeah, exactly. I wouldn't have blamed you for it. But no,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think cover letters are a thing of the past. And I, for any jobs

Claire Calfo:
Thank

Bridget Flaherty (she/her):
that I've

Claire Calfo:
God.

Bridget Flaherty (she/her):
hired for, have never required a cover letter. I've, yeah. And I also just think, everybody knows the secret here, people. You have a draft that you use for every company and you edit five words and then you send it to every other company. It's such a thing that lacks... It lacks like personality is

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
a way that I view it. Like I'm not gonna gather someone's credentials or traits or whatever it is from a 500 word essay.

Claire Calfo:
It's just like a copy paste situation

Bridget Flaherty (she/her):
It's

Claire Calfo:
usually.

Bridget Flaherty (she/her):
a complicated situation. Yeah,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I will say though, one thing that I love that a candidate did recently and she's killer. And so I was happy that she did this in the first place to get my attention.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
She recorded a video of herself

Claire Calfo:
I was

Bridget Flaherty (she/her):
and sent

Claire Calfo:
literally

Bridget Flaherty (she/her):
it

Claire Calfo:
just

Bridget Flaherty (she/her):
in

Claire Calfo:
thinking

Bridget Flaherty (she/her):
email.

Claire Calfo:
this.

Bridget Flaherty (she/her):
Yeah, have you done that before?

Claire Calfo:
Never, but I was like, I wonder if you could do a virtual cover letter.

Bridget Flaherty (she/her):
It

Claire Calfo:
What?

Bridget Flaherty (she/her):
was amazing. So she

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
used Loom, which is like the great,

Claire Calfo:
I love

Bridget Flaherty (she/her):
so I don't know

Claire Calfo:
loom.

Bridget Flaherty (she/her):
if you can, I love Loom, I'm a big

Claire Calfo:
It's

Bridget Flaherty (she/her):
advocate.

Claire Calfo:
the best. Yeah.

Bridget Flaherty (she/her):
Um, so shout

Claire Calfo:
Okay.

Bridget Flaherty (she/her):
out

Claire Calfo:
Loom

Bridget Flaherty (she/her):
Loom. Yeah.

Claire Calfo:
sponsor me. Yeah.

Bridget Flaherty (she/her):
Um, but she like Loom this video of herself and specific to, specific to why she wanted this like founder opportunity.

Claire Calfo:
So

Bridget Flaherty (she/her):
Um,

Claire Calfo:
cool.

Bridget Flaherty (she/her):
so it was like individual to the company was under three minutes. Like it was super punchy at, I sent

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
it to my whole team and I was like, we should be reaching out to people this way with a video, like it's so.

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
And so I would say swap

Claire Calfo:
it's

Bridget Flaherty (she/her):
your

Claire Calfo:
more

Bridget Flaherty (she/her):
cover

Claire Calfo:
personal.

Bridget Flaherty (she/her):
letter with a video. It's more personal.

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
especially if you really like the company, like if you're like, this is my dream company or something and you

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
just copy

Bridget Flaherty (she/her):
it

Claire Calfo:
paste

Bridget Flaherty (she/her):
takes three

Claire Calfo:
the

Bridget Flaherty (she/her):
minutes.

Claire Calfo:
loom.

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
and it shows them

Claire Calfo:
it's

Bridget Flaherty (she/her):
your personality.

Claire Calfo:
actually probably takes less time.

Bridget Flaherty (she/her):
I think it probably

Claire Calfo:
Takes less

Bridget Flaherty (she/her):
does.

Claire Calfo:
time than actually, yeah. Like, cause people

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
are

Bridget Flaherty (she/her):
so

Claire Calfo:
just

Bridget Flaherty (she/her):
easy

Claire Calfo:
like

Bridget Flaherty (she/her):
to do.

Claire Calfo:
stressing and editing. So,

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
yeah.

Bridget Flaherty (she/her):
So I would recommend that for sure. But I think cover letters are a thing of the past. I would hope, at least. And LinkedIn, that's the thing. I don't

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
even ask for resumes half the time anymore. LinkedIn is what I use as a guiding light. And I will say that depends

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
on the industry. That's very tech first, I would say. There's probably

Claire Calfo:
For sure.

Bridget Flaherty (she/her):
some other spaces

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
that are a little bit less LinkedIn heavy. But. I think the written submissions and applications have changed a lot to what they were, I would say

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
like five to ten years ago.

Claire Calfo:
I think also what it is too is maybe remote work. You don't get to go in and meet someone in person, so you

Bridget Flaherty (she/her):
Mm-hmm.

Claire Calfo:
need that more face to a name almost more than you ever have before.

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
And you get that right away now too, which is great.

Bridget Flaherty (she/her):
I completely agree.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And I always like, the one thing I wish that Zoom would in some way, which maybe is possible, like I wish you could capture more body language on Zoom. Like that's

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
one thing that I feel like in interviews, like when you're in person in a conference room, like you can gather a lot of kind of information about someone by like the way they're moving their hands or like if they're sitting on their hands or whatever it is. And so I wish there was a little bit more interaction

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
there. But. I mean, Zoom obviously has done the trick for, I got my last job remotely. I hadn't met anybody in person. I think you might've too, but crazy.

Claire Calfo:
Yeah, I've gotten all my jobs remotely, which is crazy.

Bridget Flaherty (she/her):
It's so

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
different than what you would imagine. I just remember in college people flying everywhere for these interviews, and it's just so different now.

Claire Calfo:
Oh my gosh, yeah. Going into the office from Santa Clara to San Francisco every day,

Bridget Flaherty (she/her):
Oh my God, I talk about

Claire Calfo:
brutal.

Bridget Flaherty (she/her):
quality of life. I was thinking about that before graduating. I was like, much credit out there to all you people that are like taking the bus from San Francisco

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
to one of the Silicon Valley jobs, but I did not think I could do it.

Claire Calfo:
Oh my gosh. No, no, no.

Bridget Flaherty (she/her):
I'll take

Claire Calfo:
Could

Bridget Flaherty (she/her):
the subway

Claire Calfo:
not,

Bridget Flaherty (she/her):
for now.

Claire Calfo:
could not. I don't

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
care if there's wifi on the bus. No, no more.

Bridget Flaherty (she/her):
I know, yeah.

Claire Calfo:
So.

Bridget Flaherty (she/her):
I saw someone who was on the subway in Manhattan that had their computer out and I was like, I don't know. I don't know if that's gonna work.

Claire Calfo:
That's

Bridget Flaherty (she/her):
Like there's

Claire Calfo:
going

Bridget Flaherty (she/her):
something

Claire Calfo:
to be a no for me. That just

Bridget Flaherty (she/her):
wrong

Claire Calfo:
feels

Bridget Flaherty (she/her):
with

Claire Calfo:
wrong.

Bridget Flaherty (she/her):
that. Yeah.

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
Good

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
for them. Productivity.

Claire Calfo:
no laptops on the subway.

Bridget Flaherty (she/her):
Mm-mm. That's it.

Claire Calfo:
Oh my gosh, I love it. And then so kind of like throughout the hiring process, I guess, I feel like there's what, like 100 people apply and you probably will interview like what, 10, 15 people. Besides maybe something like a, you know, video cover letter, like what are other ways that people can really stand out? I know right now the market is not a great place and there are a lot of people without jobs and you know, how do you get, I guess, noticed and what's the best way

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
to do that?

Bridget Flaherty (she/her):
Yeah, I love this question. I think, obviously, like, for the basics, like making sure that you have obviously your resume that looks good, send it to like as many people as are willing to look at a resume. Because I do think while

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
cover letters maybe are a thing of the past, like, I do notice when people maybe have like typos on their resume or things aren't like as fluid or it's not as kind of structured. And so I think it is important to make sure that you have the basics on. as well as LinkedIn profiles and things of that nature. I always say the first thing, which it seems a little bit obvious, but I think some people say they're going to do it often and then don't end up doing it. But reaching out to the recruiter or the hiring manager on LinkedIn or email is something that I think can be very overrated or underrated. Sorry, not overrated, underrated. I think for me, every time I've hired people in the past, like even now, if someone sends me a LinkedIn message. Odds are I'm going to definitely look at their application. Like I'll look and if they're qualified, I obviously will make sure that

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I have a conversation with them. Something that's short and sweet often can do the trick, but putting yourself out there and putting a face to the name, similar to the video concept. But oftentimes

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
if they see that you're a person, you're going to be viewed differently than just an application that they're reviewing. If you don't know who the recruiter is, reach out to all the recruiters at the company. There's not a bad thing about that either.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think. the more people you reach out to, the higher chance that somebody is going to respond. And so use kind of your diligence skills on LinkedIn or Google and find, even people that are in the role that you're applying for. Like I'm really

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
curious to learn a little bit more about your day to day, like just submit in my application. Like would love to chat if you have 10 minutes, 15 minutes. And keep it low lift. Like I think that's the other thing too, where you don't have to be asking for like an interview every time. Like you can just be asking for like a coffee chat

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
or something that... doesn't make it seem as formal, I think is often helpful. So that's

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
one thing

Claire Calfo:
100%. Yeah.

Bridget Flaherty (she/her):
I would say. The

Claire Calfo:
I

Bridget Flaherty (she/her):
other

Claire Calfo:
have done

Bridget Flaherty (she/her):
thing

Claire Calfo:
that

Bridget Flaherty (she/her):
too,

Claire Calfo:
multiple

Bridget Flaherty (she/her):
I would

Claire Calfo:
times.

Bridget Flaherty (she/her):
say.

Claire Calfo:
Oh, sorry. I was going to say, I've done that multiple times where I reach out to the recruiter or someone on the team. And I'm like, I just applied for this role. I would love to chat more about the companies and the culture and whatever. Can you point me in the right direction of whoever is hiring for this or something like that? And it's just so easy to do. It takes like two minutes. So.

Bridget Flaherty (she/her):
Yeah. And I think it's like, it's important to not just kind of click, submit on the application and feel like you're kind of done and you've checked the box. Like if you really like a role chase after it, like that's kind of

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
the sales kind of again, like you want to sell yourself in the best way possible. And I promise you like not only sending LinkedIn message, but use your network, like see people

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
that maybe had worked there in the past or know people that worked there in the past. And what goes around comes around. Like, you know, I'm sure you have, and I have as well, like had calls with people that are looking for their next job and they want to

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
speak about advice and things of that nature.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Chances are people are usually willing to have those conversations. I've only been

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
turned down maybe once or twice. I think it's really worthwhile to put yourself out there a little bit and see what you learn through that process.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I would even say getting creative around it, doing a little bit diligence around maybe the company's been featured in an article recently, or maybe there was a podcast with some of the employees or something

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
like that. do a little bit, like five minutes of research and send one of those snippets to whoever you're reaching out to and it'll go a long way. And

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
it'll, it'll be like, Oh my gosh, this person put in all this time to like figure out these things about the company and are showing that to me through this message. And so,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
um, a little bit more work can, can often go a long way through that process.

Claire Calfo:
Yeah, absolutely. And I know you had a second thing, so what was that?

Bridget Flaherty (she/her):
Yeah, no, for sure. I mean, I think the other thing too, in order to like stand out is, it's gonna sound very simple, but once you've maybe had like a first conversation, which I think to your point, like let's say there's 100 people that apply, they probably talk to like what 40 to 50 first people in a conversation usually, like thank you notes. Thank you notes are a thing that

Claire Calfo:
Yes!

Bridget Flaherty (she/her):
I feel like have been forgotten. And I'm like, what

Claire Calfo:
I

Bridget Flaherty (she/her):
is

Claire Calfo:
always

Bridget Flaherty (she/her):
this?

Claire Calfo:
send a thank you, no, I always do, every

Bridget Flaherty (she/her):
Good.

Claire Calfo:
time. I have to, I

Bridget Flaherty (she/her):
I'm

Claire Calfo:
feel

Bridget Flaherty (she/her):
so

Claire Calfo:
wrong

Bridget Flaherty (she/her):
glad.

Claire Calfo:
without it.

Bridget Flaherty (she/her):
That's a right answer. And I think like,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I don't know if it's, I'm not gonna, I don't know if it's a Gen Z thing, who knows? Like I'm not gonna put it out of generation,

Claire Calfo:
True.

Bridget Flaherty (she/her):
but it has been some sort of like shift in the ability to send a thank you note. And like,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
even as a recruiter, like I was, you know, back at LeafLink, like taking entry calls, entry level roll calls, like very like low lift, like not a

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
ton, but like the people that sent me a thank you note. It makes a difference. Like if you send it to the recruiter, the hiring manager, whoever, like, and making it thoughtful too, like pulling

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
something out of your conversation that you had with them. Um, you know, asking if they, maybe they were going that weekend to like a trip with their family or like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
a vacation, like asking about these things, like making sure that there's still that personal element, um, is I think it just makes a difference. And so

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I would definitely encourage you to continue to do that. Um, cause it's absolutely helpful through the process and it makes

Claire Calfo:
And

Bridget Flaherty (she/her):
people

Claire Calfo:
it just,

Bridget Flaherty (she/her):
stand up.

Claire Calfo:
it makes you like likable too. Like you're not too cool for a thank you note, just do

Bridget Flaherty (she/her):
Hmm,

Claire Calfo:
it. Like it's

Bridget Flaherty (she/her):
I know.

Claire Calfo:
a good way to stay in touch to like being on a thread with someone via email or LinkedIn or whatever. Even if you like connect with them on LinkedIn after and send them the thank you note, like it's so easy to do. And it is

Bridget Flaherty (she/her):
Absolutely.

Claire Calfo:
like a nice touch.

Bridget Flaherty (she/her):
Yeah. And like, it's such a good point about like thread or having that email connection because you never know, like even if you don't end up going that job that time, or

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
maybe they don't hire you or you don't want to move forward, like let's say

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
maybe two years down the road, they have a role that you're interested in and you want to like reach back out. Reaching back on the same thread where you had a thank you note is like a very good look. So

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
it's good to be leaving it. Like the world is such a small place and there's

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
always one degree of separation between everybody and their mother.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And so making sure that you kind of close the loop. every time. And that's the thing that I would say if there's any recruiters listening to this, like

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
that's why you always follow up with candidates. Like never ghost, like ghosting is just like,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I don't understand it. I really don't understand it from both sides. Like candidates

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
ghosting recruiters, recruiters ghosting candidates, like just all the communication thing is so important. And just delivering that good candidate experience is something that everyone should just put as the first priority.

Claire Calfo:
Yeah, 100%, I agree. Those are great. And then

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
in the interview process too, what are really good red flags to look out for and green flags for a company? Because we've all worked for a bad company or a bad boss per se or hiring manager, and I hate to use the word bad, but maybe just bad at managing or maybe

Bridget Flaherty (she/her):
Mm-hmm.

Claire Calfo:
the company's just not well structured or managed. And what are those things you think in the process that you can look out for to identify whether that's gonna be a good fit or you? for you.

Bridget Flaherty (she/her):
I love this question. Yeah, I always say it like, it's not a good fit or there's areas for improvement

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
in the partnership

Claire Calfo:
work in

Bridget Flaherty (she/her):
we'll

Claire Calfo:
progress.

Bridget Flaherty (she/her):
call it, but there you go, yeah. I think red flags, well, actually I'll start with green flags. Like I think

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
kind of just, it's good segue, like communication through a process, responsiveness. Like I think that's something that I always look out for from the candidate side, but also in job searching. Like I want them to reply to my email. sounds crazy, but like I want them to reply to my email within like two hours. Like I think that's something that, you know, being able to put a priority, if they're putting a priority on you through the hiring process, like chances are they're going

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
to prioritize you working at the company. And so

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
I think that's a certain green flag is that you never have these moments of like, I don't know what the next step is, or I haven't been in touch with them for a couple of days. Like that acceleration and momentum I think is a really good sign.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Second, I think like them not rushing you, like I think it's fair for people to be put on a deadline, but I think like anytime I hear folks that have been through a recruiting process in like less than a week, I'm like, whoa, whoa, whoa, whoa, whoa. Like they didn't even have a time to like think about you versus like you thinking about the opportunity.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And so I think allowing there to be a little bit of space to breathe

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
is a helpful thing. And there's a line there, but I think that's a healthy one to toe.

Claire Calfo:
Yeah, I agree. I feel like 24 hours is not long enough to respond to a job offer. You need more time.

Bridget Flaherty (she/her):
No, I know. And right

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
now in the market, people are taking advantage of that in a big way.

Claire Calfo:
100%.

Bridget Flaherty (she/her):
Like I've heard like 48 hours is like the standard now. And I'm like, boy, oh, like

Claire Calfo:
No,

Bridget Flaherty (she/her):
I still get

Claire Calfo:
no,

Bridget Flaherty (she/her):
people

Claire Calfo:
no.

Bridget Flaherty (she/her):
a week, like push for a week. You definitely.

Claire Calfo:
Yeah, yeah, and you probably have other offers or interviews, so it's totally normal and fine to wait that out.

Bridget Flaherty (she/her):
Yeah, and chances are, that's a thing that you can't forget, is when you're at the end of a process, the company, and let's say they make you an offer, they want you, and it'll be harder for them if they let you walk away, because they're gonna have to start all over, in a sense.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And so, when you're at that finish line, you are in the driver's seat. You can ask for whatever you wanna ask for, and it's also a good opportunity, because you don't know when you're gonna be able to ask again for whether it's that more salary, or equity, or whatever it might be. And just ask for it. just

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
you are the most important person in their world at that moment. And so like use that to your advantage.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And don't be shy in doing that. And that's, I mean, it's another green flag, if they give you that space, I think it shows that they're respecting. And obviously, they're going to put a deadline,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
so they're not gonna let it drag out forever. But allowing that to be a conversation more than them just making a decision, I think is a good, a good thing to think about.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Other green flags, like I think, we talked about a little bit, it was it relates to DEI, but like seeing people that look like you, I think You know, in, it's

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
successful in roles, I think is an important thing. You know, I always look at people that maybe had since left a company, like recently, whenever I'm looking at other corporations or jobs that I may be interested in. Like if you see a lot of like, I don't know, maybe early level or like entry level people leaving or like senior level people leaving, like it's a good thing to ask about through the process and understand kind of why that churn or attrition is happening. You know, understanding kind of like, you know, was there just like a department that maybe everyone was upset with that left in all at the same time, or was it more widespread than that? And so just kind of understanding and poking

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
holes a little bit, I think is important. But those are some of the green flags, I'd say like, red flags. I always say to people like, it's okay to look on like glass door and those sites, but like they're such reactionary, like feedback

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
forums that just take it with a grain of salt. Like it's better to get

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
your own opinion through going through the process than just making a judgment call based on the feedback that's on those sorts

Claire Calfo:
So

Bridget Flaherty (she/her):
of websites,

Claire Calfo:
true.

Bridget Flaherty (she/her):
right? Like it's just, it's very reactionary.

Claire Calfo:
It could be like five stars on Glassdoor 2 and you have like a horrible experience there

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
or vice versa.

Bridget Flaherty (she/her):
And it's super individual. Like that

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
one, that one person wrote is not going to like mirror your exact same experience. And so I think it's important to like,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
make your own, like make your own judgment call, go through the process yourself, like gather the information, obviously speak to people that work there and do, I call them like reverse references. Like always

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
ask when you're at the last stage of the process to talk to people that are in the role or at least in a similar function. So you can understand.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Or people like if you're gonna work for this one manager, like ask to speak to people that report to them.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
They're gonna probably do references on you, like you can do references on them and understand the experience

Claire Calfo:
100%.

Bridget Flaherty (she/her):
of people that have worked with that person. So I would say like, red flags the inverse, like rushing through them, rushing you through the process, like shows a little bit of desperation, I would say probably not in

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
a good way. I would say like a sloppy process, like this may be the recruiter in me speaking out, but like... You

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
should know from the beginning of the process, like what all the steps will be, what the timeline is going to be, what's going to be asked of you through the process, whether there's a take home

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
or a pitch or whatever it might be. Um, and

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
then following that structure, I think is a really good sign. Um,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
and I think like speaking to people on the leadership team, like no matter how big the company is, like you really want to be able to speak to people at every level, um, to understand kind of the dynamics and how they interface. And like, if you're aligned with the leadership style. Maybe you don't have to interact with that person actually in the day to day, but it's good to know the people that you might be working for, even if there's a couple of layers of separation. Also, just try as much as you can to speak to someone who maybe has left the company, or doesn't work there anymore.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
Use your networking skills and find someone. Granted, they may have not left on good terms sometimes, they may have a different perspective, but you're just gathering all the perspectives to make your own calculated decision. So it's

Claire Calfo:
Totally.

Bridget Flaherty (she/her):
not as much of a red flag,

Claire Calfo:
You're

Bridget Flaherty (she/her):
but

Claire Calfo:
doing

Bridget Flaherty (she/her):
something

Claire Calfo:
research.

Bridget Flaherty (she/her):
that might realize a red flag, doing research, exactly.

Claire Calfo:
Yeah, yeah, so smart, yeah. And I guess outside of those green red flags, what are good questions to maybe ask the recruiter or the hiring manager to get a grasp on whether that's culture, or what your day to day is going to be like? What are your favorite questions you get asked? And this could be even to put yourself out there again, how to stand out, those questions that are really um

Bridget Flaherty (she/her):
Mm-hmm.

Claire Calfo:
you know impressive in your opinion.

Bridget Flaherty (she/her):
Yeah. One of my favorite questions recently is, like, and it usually is most applicable if you're talking to the manager of the team that you might be working on, or like a leader of some

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
capacity. But like, what keeps you up at night, I think is a very powerful question.

Claire Calfo:
Oh,

Bridget Flaherty (she/her):
Yeah, it's

Claire Calfo:
yeah.

Bridget Flaherty (she/her):
like, it just like makes you think for a second.

Claire Calfo:
I asked that in my very first job interview. I totally forgot

Bridget Flaherty (she/her):
good for

Claire Calfo:
about that

Bridget Flaherty (she/her):
you

Claire Calfo:
one. That one's good.

Bridget Flaherty (she/her):
there

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
you go bring it back to the arsenal

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
that's a good

Claire Calfo:
I forgot

Bridget Flaherty (she/her):
one

Claire Calfo:
about that.

Bridget Flaherty (she/her):
um

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
because

Claire Calfo:
there

Bridget Flaherty (she/her):
i

Claire Calfo:
you

Bridget Flaherty (she/her):
think

Claire Calfo:
go.

Bridget Flaherty (she/her):
like there's a lot that keeps people up at night and like if someone asked me that question like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
i would probably be honest and i think like it's

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
it's different than just saying like what's the biggest challenge that you're experiencing and like people are going to pull something that maybe

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
that day they're

Claire Calfo:
snore.

Bridget Flaherty (she/her):
frustrated with and like say it and be

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
like okay um but i think that when it goes a little bit it goes a little bit deeper so and i don't know like i think like being able to position it in a way where it's like, this is usually like the biggest thing that might be a, why this, whatever it is company might fail is usually

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
what you're trying to get at. And it's okay if there's fail reasons or failure reasons. And I think like just knowing them is important when you're going through a process.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
So that's one that I always encourage people to ask.

Claire Calfo:
You also

Bridget Flaherty (she/her):
I

Claire Calfo:
probably

Bridget Flaherty (she/her):
think.

Claire Calfo:
get to know if people have work-life balance. Like if everyone answers like, oh, like work keeps me up at night. And then versus if they're like, oh, this, but also like, I'm passionate about this or like, I think about this a lot or, you know, like you probably get like

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
a better sense on how that is.

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
Yeah. And hopefully, yeah, hopefully. And I think asking people that that's a good point too, like the work life balance thing. Like I think you have to ask it in a pretty explicit way to get like a real answer versus like how's work life balance. But like, walk me through your last week. Like how did that look day to day? Like what were like the projects you were on?

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
Like what did you do after work? What hobbies you have after work? Like understanding that there are more. And kind of helps that personal thing of standing out too, like understanding the person beyond the work, I think is important because it speaks to the culture that the company probably has.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And I think the other thing too is like, when's the last time, to a manager again, like when's the last time that you receive feedback, I think is a really positive one

Claire Calfo:
Ugh,

Bridget Flaherty (she/her):
too, understanding

Claire Calfo:
that's

Bridget Flaherty (she/her):
like...

Claire Calfo:
so good.

Bridget Flaherty (she/her):
their flaws, but also the way that they receive feedback. If they're kind of brushing it off in the answer, saying, oh, someone told me X, but it wasn't that big of a deal. Or like, oh, yeah, this person ended up leaving the company. OK, that's

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
a big red flag. You want to understand

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
the way that they... Because getting back to the beginning of this conversation, you want to be able to push back in a healthy way.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And so understanding the feedback loops, I think, is really important.

Claire Calfo:
Yeah,

Bridget Flaherty (she/her):
And then

Claire Calfo:
so

Bridget Flaherty (she/her):
I'd say...

Claire Calfo:
true.

Bridget Flaherty (she/her):
nitty-gritty stuff, like just asking like when, what are the review cycles? Like what is the process for like promotion? Like understanding those things too. Because I just speak to so many people who are stuck, not stuck, but like are just frustrated because they wish that they've had like a recent promotion or a salary increase. And like it's just something that they never talked about

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
before joining the company. So it's important to get those questions

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
answered too.

Claire Calfo:
Yeah, absolutely. And then my last question around this is just when you're at the end of an interview or even at the beginning, what's the best etiquette around talking about salary? And should you always take the first offer? So if you come back to me after the whole process, I get the job, and you're like, Claire, I'm offering you X, Y, Z, should I always just accept that? Or should I, you know, pushback and it could be dependent, but I'm curious on your recruiter perspective on this.

Bridget Flaherty (she/her):
That's such a good question. And this is also coming from someone who I have to be self-reflective here because both of the jobs that I took are in tech. So LeafLank and now Fractal, like I did not negotiate

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
salary.

Claire Calfo:
Uh huh.

Bridget Flaherty (she/her):
The first was a mistake. I wish I would have done in the first. I wish I would have negotiated more in the first job. The second was a little

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
bit more interesting because I think it was, they were paying me very fairly. Like I think I knew

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
at that point that it was like, market for what I would be doing. Like I really dug deep on that and it wasn't

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
increased from what I was getting before. But to get back to your question, like second question, you should always try to negotiate. Like, and

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
so I had to make the disclaimer that I did not, but like

Claire Calfo:
Yeah

Bridget Flaherty (she/her):
coming from my reporter in any job that I would take moving forward from here, like definitely negotiate because it sometimes could be the last time that you can ask that question for at least like a year. And so you

Claire Calfo:
So

Bridget Flaherty (she/her):
just

Claire Calfo:
true.

Bridget Flaherty (she/her):
want to make sure that you check that box. As I said, like they're not gonna wanna lose you at the finish line. Oftentimes they're gonna do whatever they can to make it work. Or like, I always say shoot for the moon because you'll land amongst the stars somewhere. So just

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
try to like stretch it as much as you can. And they'll oftentimes, worst case, come back in the middle or stick to it. And if you're excited, you'll accept it anyway.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
But I think like etiquette wise, you know, in the first conversation. Usually a recruiter will ask you like, what are your salary expectations for

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
a next role? And there's obviously they can't ask you what you're currently making because of legal stuff. And that's usually

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
the way that they'll position it.

Claire Calfo:
And don't tell them that.

Bridget Flaherty (she/her):
And don't tell them that exactly. And so I think like

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
flipping it, flipping it on them is usually the best way you can do it. And now there are actually laws. New York at least, I think California and probably a couple other states

Claire Calfo:
California.

Bridget Flaherty (she/her):
too, where you have to have the salary range in the job description.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And so you should know more going into the conversation than you might have like two or three years ago. But asking them and they're

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
required to answer, like what's the salary range that you have slotted for this role? That way you have a better

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
understanding. And let's say like it's lower than what you were hoping for. I think it's important to be honest as early as you can in the process

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
saying, like I'm actually shooting for X to Y range and like if that's not something that you can make work, like I don't want to waste your time, you can do it in a very respectful way. So

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I would say like as always you can have the salary conversation the better. If you somehow find yourself in the middle of a process, which can happen without like having talked about salary, don't be bashful of just like emailing the recruiter,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
whoever you're in contact with and saying like, do you mind if we just chat for 15 minutes, like want to make sure that we're aligned on like compensation expectations before we move into the next round of the interview. Like it's never too late

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
to ask the question. This is what I'm saying.

Claire Calfo:
Totally. Yeah. Yeah. And I think the biggest thing that I've learned too, just in negotiation, in those early stages, like you were saying, is again, what we said already, never tell them what you're making right now. And

Bridget Flaherty (she/her):
Yes.

Claire Calfo:
just do your research. You were saying too, look at the market and see what your years of experience. There's all these resources now of places you can go and say, I have this many years. I do this.

Bridget Flaherty (she/her):
Yes.

Claire Calfo:
I'm in this industry. And they'll provide you with the high and the low. And you can shoot off the high if you're feeling bold. And Um,

Bridget Flaherty (she/her):
as you

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
always should.

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
I

Claire Calfo:
there's

Bridget Flaherty (she/her):
always

Claire Calfo:
like

Bridget Flaherty (she/her):
say

Claire Calfo:
way

Bridget Flaherty (she/her):
shoot

Claire Calfo:
more

Bridget Flaherty (she/her):
off

Claire Calfo:
out

Bridget Flaherty (she/her):
the

Claire Calfo:
there.

Bridget Flaherty (she/her):
high. Yeah, shoot off the high because I think

Claire Calfo:
Always.

Bridget Flaherty (she/her):
like

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
and also it's important

Claire Calfo:
Even

Bridget Flaherty (she/her):
to

Claire Calfo:
if

Bridget Flaherty (she/her):
you

Claire Calfo:
it feels

Bridget Flaherty (she/her):
too

Claire Calfo:
crazy,

Bridget Flaherty (she/her):
like

Claire Calfo:
just do it.

Bridget Flaherty (she/her):
just do it. Always do it because like they're not going to and especially as a

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
woman like oftentimes people do not like shoot for the moon in that way like which I probably just did by saying it was fair the amount of money that I was getting

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
paid but it's like if everybody goes out and asks for more so you

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
might as well just do it too. But like it's important to also think about

Claire Calfo:
Exactly.

Bridget Flaherty (she/her):
what's important to you in terms of compensation. Like there's a lot

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
you know, base salary, there's equity in some cases. And so making sure that you understand

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
like what is most important to you before going through those negotiations, I think is really important. But

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
easy to get on the phone and say like, oh, this is what I want, I want, but like, if it doesn't work for you, like that's okay. But like, don't say that, like, no, just be like, this is what I'm

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
looking for. Leave, let

Claire Calfo:
Take

Bridget Flaherty (she/her):
there

Claire Calfo:
that

Bridget Flaherty (she/her):
be

Claire Calfo:
out of

Bridget Flaherty (she/her):
the

Claire Calfo:
your

Bridget Flaherty (she/her):
healthy

Claire Calfo:
vocabulary.

Bridget Flaherty (she/her):
team. Exactly, never apologize.

Claire Calfo:
It's OK out

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
of your vocabulary. Yeah.

Bridget Flaherty (she/her):
it's okay,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
never say I'm sorry. Like, just don't be bashful

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
about it.

Claire Calfo:
For sure. Yeah, because it is normal. If a recruiter hears that all the time, I'm sure. You've heard people negotiate constantly. So it's not like it's abnormal that you're asking for something higher.

Bridget Flaherty (she/her):
Yeah, exactly. And I'd

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
say the only other thing I would say there is like, I often find when I make an offer to a candidate, like, and I say, let's say the deadline's a week out, usually,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
like, I'll only hear about the salary stuff like two days before the expiration of the offer. Like bring it up

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
early and often. Like when you, when you get an offer from someone, like the next day, if you want to shoot higher, like tell them then because it'll give you more time to like work through that negotiation. And oftentimes

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
if they, because it shows if you're trying to negotiate. Oftentimes it shows your excitement about the opportunity. Like you wouldn't negotiate if you didn't actually want this job. And

Claire Calfo:
Right.

Bridget Flaherty (she/her):
so we'll wanna close you even faster if they know that you're like at the finish line, but really

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
it's just the details of comp that you're working through. So bring it up, like don't wait till the last minute, like bring it up as early as you can.

Claire Calfo:
Yeah, absolutely. Yeah, and then also it gives you more time to talk to the hiring manager. It gives everyone on the back end more time to adjust and figure out budget and do whatever they. It depending on the company size too. If you're a smaller

Bridget Flaherty (she/her):
Exactly.

Claire Calfo:
company, they probably need more time. But I think,

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
yeah, I like what you said. Early is better. So

Bridget Flaherty (she/her):
Yeah,

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
definitely.

Claire Calfo:
that's good. I know we're really close on time. So is there anything that we haven't talked about that you really want to share with us or something that's really important? that we should keep in mind just like on the topics we've talked about or just in life.

Bridget Flaherty (she/her):
I think one thing is before, because I feel like I've talked to so many people the last couple of weeks that are like on the job hunt,

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
maybe through unfortunate layoffs or just kind of thinking about what's next in general.

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
And I think one thing that's super important before you start sending those applications or reaching out to people is just understanding kind of the state of mind that you're in before going into that job

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
search. Because

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
I think like oftentimes like finding a job can be a job in a lot of ways. And it's not to say that you can't do it while having another job. currently, but I think you want to make sure that you're not like wearing yourself too thin or like beating yourself up because you're going to get rejections. It's going to be shitty sometimes.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
Like you're going to be turned down from things that you maybe really wanted. And like you want to make sure that you're, you know, feeding yourself and your soul in a healthy way through that process. Um, cause you'll be spread thin. I think you're going to have to make tough decisions. Like anytime you have to decide about what you're doing as a career. career choice is like a big decision and you need to give yourself grace

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
through that. And you're going to learn a lot about yourself along the way. And so it's important to make sure that if you're not feeling just right, like, let yourself sit a little bit, don't rush into it, like, write down like what you want to prioritize and in the next role, and it'll help kind of guide that journey. But don't be afraid because I think there's a lot of pressures like when you're job searching, like from whether it's parents or friends or whatever it might be

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
to like send in 100 applications, like you just got to get it moving. And I'm not going to say that you don't have to put in that work like you do, but

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
doing it when you're doing it for yourself is just so much better than when you're trying to do it for somebody else. Um,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
and the other other thing I would say there too, is like, oftentimes I find myself like poking around job boards when I'm like really upset with something that's happening at work. Um, or like

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
really just like, you know, PO about, you know, my coworkers saying X, Y, and Z. It's like, I'm going to go look at this job

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
board and find something else. Like, That is the opposite time of when like you should be looking for a job. Like you should be looking and thinking about that when you're enjoying what you're doing. So it's not like clouded

Claire Calfo:
Right.

Bridget Flaherty (she/her):
in a way. And that obviously

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
if you're in a toxic environment or like really stretched thin, like there's a lot of circumstances that it's, that's not going to be entirely possible, but try to make sure

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
that you're running towards something versus running away from something. I think is the best way I can put it.

Claire Calfo:
Yeah, I love that, running towards not away. That's

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
so true. And yes, agreed on the toxic stuff, toxic work environment, but yeah, that's such a good tip, I think.

Bridget Flaherty (she/her):
Yeah. And the other thing too,

Claire Calfo:
Okay,

Bridget Flaherty (she/her):
I would say

Claire Calfo:
well,

Bridget Flaherty (she/her):
is like one other thing, just briefly

Claire Calfo:
oh yeah.

Bridget Flaherty (she/her):
with all, with chat GPT and like all this AI stuff, like if you're ever struggling

Claire Calfo:
Ugh.

Bridget Flaherty (she/her):
with like inspiration of like jobs to like companies or like questions to ask, use it, like it's such a good spark to like just get

Claire Calfo:
It's

Bridget Flaherty (she/her):
things

Claire Calfo:
so,

Bridget Flaherty (she/her):
going. So

Claire Calfo:
yeah,

Bridget Flaherty (she/her):
that's

Claire Calfo:
it's

Bridget Flaherty (she/her):
my

Claire Calfo:
amazing

Bridget Flaherty (she/her):
last plug for the day.

Claire Calfo:
what it can do. And you can personalize the, like, give it as much, maybe we shouldn't be giving AI all this information, but give it a lot of information and be like, I'm looking for this

Bridget Flaherty (she/her):
And...

Claire Calfo:
job, I've done this in the past, like, what would I be good at? Like, it's such

Bridget Flaherty (she/her):
Yeah.

Claire Calfo:
a crazy free tool.

Bridget Flaherty (she/her):
Yes.

Claire Calfo:
I saw on Snapchat, they just added like a little chat GDP on that, it's like, ask me anything, and it's like a person. I'm like, what

Bridget Flaherty (she/her):
going

Claire Calfo:
is

Bridget Flaherty (she/her):
to

Claire Calfo:
happening?

Bridget Flaherty (she/her):
be everywhere. But get

Claire Calfo:
I know.

Bridget Flaherty (she/her):
ahead of it and use it to your advantage because it's probably using some of our information. So might as well just

Claire Calfo:
100%.

Bridget Flaherty (she/her):
use it for life worth. Yeah.

Claire Calfo:
At this point, it's fine. Just take it all. My last question for you is obviously the name of the podcast, What Did Your Mom Forget to Tell You? We

Bridget Flaherty (she/her):
I

Claire Calfo:
love

Bridget Flaherty (she/her):
was thinking

Claire Calfo:
her.

Bridget Flaherty (she/her):
about this. I know we love that. I was thinking about this before getting on the call because I was listening to a couple of the other ones, but what did my mom forget to tell me? Oh, okay, this is gonna be one. Hopefully my mom will listen to this, but sometimes your mom can be wrong. Sometimes your mom is wrong,

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
which

Claire Calfo:
Oh yeah.

Bridget Flaherty (she/her):
I'm sure all of us have learned time and time again, but especially as you're job searching to bring it full circle here, like you know yourself better than anybody else.

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
And there's gonna be a lot of pressures from people to steer you one way or the other, but you were made from these parents in this family that raised you and grew you to the person you are now, so you can trust yourself a little bit. And so it's

Claire Calfo:
Mm-hmm.

Bridget Flaherty (she/her):
okay to not always listen to the people that kind of brought you to where you are today, but respect them always.

Claire Calfo:
So true. And you went to college, you had your own experiences, you know yourself, you know what your skills are. Yeah.

Bridget Flaherty (she/her):
Yes, absolutely.

Claire Calfo:
Yes,

Bridget Flaherty (she/her):
So that's

Claire Calfo:
I love

Bridget Flaherty (she/her):
my...

Claire Calfo:
that one.

Bridget Flaherty (she/her):
You've probably heard a lot of good ones.

Claire Calfo:
I have, I need to make a compilation of all of them. That was my plan.

Bridget Flaherty (she/her):
Yeah, I love that little book. I would

Claire Calfo:
Yeah.

Bridget Flaherty (she/her):
buy it.

Claire Calfo:
Yeah. Oh my God. That's a good idea. My next money tool.

Bridget Flaherty (she/her):
There we go.

Claire Calfo:
Okay, well, Bridget, thank you so much. I just

Bridget Flaherty (she/her):
This

Claire Calfo:
like,

Bridget Flaherty (she/her):
is so fun!

Claire Calfo:
I'm so excited for like my I'm thinking my sister right now. Like I'm so excited for her to listen to this while she's like job searching posts like with upcoming graduation and just all the people who are maybe like recently laid off like I think it's just gonna be

Bridget Flaherty (she/her):
Absolutely.

Claire Calfo:
such a good listen. Yeah.

Bridget Flaherty (she/her):
Yes, well thank you and reach out to me people, whoever's listening to this, I'm always happy to help with like recruiting stuff. So find me on LinkedIn, happy to help in any way I can.

Claire Calfo:
I'll put

Bridget Flaherty (she/her):
And thank

Claire Calfo:
your

Bridget Flaherty (she/her):
you Clay.

Claire Calfo:
contact info in the show notes for everyone.

Bridget Flaherty (she/her):
Please do, yes, reach out, anybody and everyone.

Claire Calfo:
Okay, wonderful. Okay, I'm going

Bridget Flaherty (she/her):
Yay.

Claire Calfo:
to

Bridget Flaherty (she/her):
Woohoo.

Claire Calfo:
stop the recording and we can stay on.