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Welcome to Deep Talks! Today, we're connecting the dots between two worlds that may seem
different but are incredibly aligned, project management, and travel advising. Joining us
is Cara Donlevy, founder of Curated by Cara and a recent Travel and Leisure Rising Star
award recipient. With a background in project management, Cara brings a level of precision
and professionalism to her client experience that sets her apart. So in this episode, we
are going to talk with Cara about how she applies her project management background to
everything from onboarding to itinerary delivery and how this mindset can help elevate any
advisor's process no matter their background.
Hi and welcome to Tea Talks. I'm Robin Bradley.
And I'm Jennifer Jacob. Consider us your travel industry best friends here to root for your
success every step of the way.
With my background in sales and marketing and my career as an HR management professional,
we've combined our experience to grow a simple itinerary creation company into a multi-million
dollar host agency. We've been in your shoes, juggling it all from building a brand to handling
the daily challenges of running a business. This is the place where you can expect to
get practical advice, fresh ideas, and maybe even a few laughs. We've made the mistakes
so that you don't have to. Sharing what we've learned to help you work smarter and scale
your travel business. So grab your coffee or cocktail and let's dive in. We're here to
help you build a business that works for you.
Welcome, Kara. We're so happy that you're here.
Thank you. Thank you for having me.
To kick us off, I would love for you to tell us a little bit about that background and
how you got into travel.
Sure. Well, I'm Kara. I'm a luxury travel advisor based in Boston. I live here with
my husband and my family. And I've been here since 2014, kind of grew up living all over
the East Coast, but love Boston. Don't plan on leaving.
I got into this role in a little bit of a non-conventional way. I went to Lafayette
College in Pennsylvania and pursued a bachelor's degree in engineering with a focus on construction
and project management. And I graduated in 2012 from Lafayette. And immediately after
that, I dove right into the commercial construction industry. And for the next 12 years, I worked
as a project manager overseeing the building of large-scale commercial and academic buildings
throughout Pennsylvania. Especially, I built a couple of buildings at Lafayette where I
went to school and then moved up here in 2014 and continued on that role until about 2024.
So I started my business curated by Kara in January of 2021 as kind of a part-time nights
and weekends gig. I love to travel and I always knew that I wanted to do something with it.
So I started that business and really just grew my book of business through referrals
and social media. I did that for a couple of years alongside my full day job. And then
in January 2024, as we wrapped up completing the construction of a building in Boston,
I was unexpectedly laid off, which came as a little bit of a shock. I took a few days
to just sit, reflect, and honestly, with the support of my husband and my family, came
to the realization that, "Okay, I can actually do this job as a travel advisor full-time
and I can make it work." So I kind of jumped all in. It was a little bit scary. I did that.
And honestly, I have not looked back. The business has taken off considerably. And it
was really during that time that I realized, "Wow, I can take so many of my project management
skills from scheduling, budgeting, attention to detail, and apply those to creating these
super memorable custom trips for clients." I love that you said that because I've always
thought when looking at these CRM platforms, that's why I was very attracted to travel joy
when I first made that transition was because it wasn't just a hub holding my client details.
It was actually these stages of an actual project. And to me, travel planning is project
management. There are various stages. There are budgets to be aligned with. There's a lot of
math actually as the advisor and a lot of managing expectations on timelines. And that's
very project management-based. Right. Yes. Let's talk a little bit about
those similarities that you're saying. So we just kind of touched on these, but
let's start with the scheduling and the timelines. Let's talk about how you feel
like that's so perfectly aligned. So with scheduling and timelines, so in the construction
industry, the motto that we lived by was on time and on schedule. The investors in the projects
wanted to make sure everything was always on time and on schedule, and that's what we strive for.
So similar in the travel industry, we want everything to be on time and on schedule with
the client. So that can be anything from coordinating the airport transfers all the
way to the hotel check-ins, to the experiences, to their day-to-day itinerary and making sure
everything behind the scenes works perfectly. A lot of the times your average person is not
going to see the inner workings of building a building or the inner workings of me sitting
here during the day and crafting this itinerary for them. Alls they care about is the final product.
So you want to make sure at the end of the day, you're delivering a final product
that's shiny, easy to manage, and the client is just able to enjoy.
And just like building a building, not to be redundant, but the actual things that you're
talking about, the granular details, the steps that are going into it, the little hiccups along
the way, you don't want the person who's commissioning the building or the actual person that's
funding the building. They are bringing in a project manager so they don't have to deal with
the granular pieces of the project. Exactly. And that's exactly travel planning. It is still
collaborative. You're still saying, "Here's how I want it done. Here's how I want it to look.
Here's how I want the building to feel to someone that walks into it." And there might be some
specifications, but at the same time, you're collaborating, not controlling. And as a project
manager, you are behind the scenes making sure all of those things happen without that person
feeling every bump and crack along the way. Exactly. I could not agree more.
Let's jump to budget management because we talk about budgets in this kind of taboo way
in the industry where it's almost like a frustration point. We view it as a limitation,
and I wish we didn't really, but I think that's frankly the state of the world a little bit right
now. We are running up against so many limitations when it comes to budgeting. One of my favorite
travel advisors, he just posted on his story yesterday that he was helping his client find
tickets to Europe this summer, and he's like, "I cannot believe economy is $1,900." I'm like,
"Okay, my economy ticket was $2,200 times three because there are three of us in the family going."
And seven years ago, I'm going to take it back to when I started, a $6,600 trip, the
price of three airline tickets could have paid for air and four-star accommodations over a
12-day trip in Spain. I know that it's what I was making happen at that time. I wish we didn't
have to have it from a taboo lens necessarily, but it is our responsibility to manage a budget
and to make sure it all aligns with their expectations. I know that that was a really
rambly lead up for that, but I would love to hear your perspective on this.
Sure. Yeah. Managing client expectations, that's what it all comes down to.
Instead of saying what is your budget, say, "Okay, what are you looking to invest in this trip?"
When it comes from the type of hotels that you're looking to stay at, the type of experiences that
you're looking to do. So similar in construction, a lot of the times, the owner's not going to come
and tell me as the project manager, "I want to spend $20 million on this building," because if
that's the case, then we're going to do everything we can to get right to that $20 million mark.
Instead, they want to tell us what their preferences are, what they're looking for,
the services and amenities within the building, and then work together to craft something that
works for each of us. So that said, I think it's very essential to be mindful of the budget,
but instead more asking, "What is the investment that you're looking to make,
throwing out a couple ideas of numbers? Are you comfortable with this value? Does this make sense?"
And kind of go from there, and again, just over communicating to the client and working with
them every step of the way to make tweaks, to make adjustments, to finally get to that final number,
which could be more than what maybe was originally in their head, but I think part of our job, too,
is being able to show the client full picture, a whole vision of what they could see on this
trip, presenting experiences that maybe they weren't thinking about, and then it's, "Oh,
yeah, that is worth the extra money to do that." So just again, over communicating and kind of
working with them to put together that budget in place, and then when we're ready to pull the
trigger, everyone is comfortable with that number. You just took my mind completely to like HGTV style
shows, and I'm not likening project management. I know there's a very big difference between
like the interior design and decor than the actual project management, but I do think of it as,
"Hey, I know you wanted your bathroom to look like this, but what you're describing is actually in
this price point, and here's an opportunity. You're only going to do this once. You're not going to
renovate every few years, so do you want to spring for the hardware that has a more luxe look and
has a little bit better durability to it, and you are presenting things in a pragmatic way,
but you're sharing the opportunity you're not selling to them." And I think that's very parallel
in what you're talking about. So I like that you said that it might be a gradual kind of like
snowball effect of looking at the budget, because we all know that it's not, "Hey, here's your package.
That's not the end-all, be all," because they might actually want to upgrade later on. They might
want to add a private boating experience later on as they realize, "Hey, this might actually be
my one time to go to the Amalfi Coast, because next time we go to Italy, maybe we do the Northern
area." So the budget piece is more parallel to project management than I even realized. I was
thinking much more in the staging and the timing schedule management, but I think that the budget,
how do you feel like that helped you prepare for these conversations?
So one thing, again, that is pretty parallel, is in construction pricing is always changing.
Pricing of materials is constantly changing, going up over the years, and similar. So we have to be
able to be proactive and anticipate that if we are budgeting a job, let's say in 2024, but we know
that job is not actually going to start being constructed until mid-2025. We have to anticipate
and put a little bit of a percentage on that, that those costs are going to go up by middle of 2025.
So same thing, if someone comes to me and says, "Hey, I want to go to Italy again," just as an
example, next summer, for the past four years that I've been in this industry, pricing in Italy,
especially on the Amalfi Coast, has gone up every single year. So the number that I give them today
is most likely not going to be that number next year. It's probably going to be 10% to 20% more.
So in project management, again, anticipating that, "Hey, those prices are going to go up,
it's very similar to this industry," that you have to put a little bit of an increase on those
numbers so you're giving them a true well-rounded estimate. I like that you approach it so factually
too, because it's not like we create the pricing. And a lot of the time, people are very intimidated
to talk about pricing in this very factual way, but the prices are the price. We can't negotiate
the price. Exactly. And we're just the deliverer. And essentially, if you're coming to us to solve
the problem, which is to help you get the best possible experience because you don't know what
you don't know about that destination, then all I'm doing is being the communicator and the middleman
of the situation, but I'm not actually creating the price, just like you're not creating the
price of materials. Exactly. Okay, let's touch on risk management and problem solving, because
this is where I think you are so equipped for this. And I can completely see how your previous
experience has adequately prepared you for the what-ifs of travel. So let's just dive in there,
give us your thoughts on project management compared to travel advising in these two areas.
Sure. So yeah, I think with both, we always have to be prepared that something is going to
happen. Unfortunately, hope for the best plan for the worst is kind of my motto. In construction,
we could have everything buttoned up. We're waiting on final inspections. And all of a sudden,
there's an error on the fire alarm panel. And the fire department is just about to show up. And we
know that if we don't get this resolved, then we're probably not passing that inspection.
So having the electrician on site, having them ready to go and prepared. So similar to that,
yes, we could have this whole itinerary buttoned up, ready to go. Client knows what they're doing.
But all of a sudden, their flight is delayed. Their flight is canceled. Something is happening.
I unfortunately had a situation with a client a couple of years ago where everything was set to
go. They get to customs in Rome, and one of them was rejected due to their passport and sent back
home. Completely unique. Apparently, customs said their passport had been stolen, which was not
the case. The client was never aware they had their passport right there. But somewhere within the
customs system, it was marked as stolen. No, that's wild. So the one client stayed in Italy because
they had a wedding they had to attend to and the other one flew home. And they were supposed to be
gone for two weeks. So we immediately kind of worked together, jumped into action again. This
is a very extreme case. But through the help of the town they live in Massachusetts, we learned
that if we could get one of the town representatives to help out, they could get an immediate
appointment at the passport center here in Boston. So by the time the client had landed
back in Boston, we had an appointment set up. We had the step by step, okay, when you land,
you're going to go to this appointment. You're going to get your passport. It's going to take
24 hours to get. Book your flight back in 48 hours just to be safe. And in 48 hours,
he was back in Rome. But I'm very much of the mindset of like, I'm going to do whatever it takes
to resolve that issue and nothing is impossible to me. But you do have to be prepared at any given
moment that I could get a text or call that something is wrong and you have to be ready
to resolve it. This is where I do think that a lot of advisors who weren't going into this
industry with that mindset were kind of shaken out during COVID. Because if you are someone who
likes routine, if you are someone who likes to be able to get ahead of situations before they
happen, and I don't mean like, I actually kind of love the critical thinking piece of travel,
like I think those challenges are fun. Like, yeah, we did it. It's like such a victory afterward.
But if that's not where your adrenaline comes from, then this is probably not the right industry.
And I don't mean that to be negative, but maybe a support role in travel or a sales
role for someone, an administrative role where you can simply be doing something on the back end
or being a creative aspect of a travel agency. But the actual management of a trip does require
someone to have a little bit of a thick skin and to not be so emotional when something goes wrong
that they immediately take it personally. There's nothing you could have done to get ahead of that.
It's not like you are going to be able to check on their status of, you know, for the
password office. That's just the craziest circumstance I've ever heard of. But there are
obviously other things that come up in travel all the time that are going to derail plans.
And you have to be quick on your feet, but you even more than that have to show up confidently
to your clients so they don't lose trust. You getting nervous and falling apart,
they're essentially paying for you to be the one that controls the chaos.
Right. Calm, cool and collected.
Exactly. Like a wedding planner. Like I think those two things are very synonymous is like,
travel advisors are remote wedding planners, if you think about it.
I agree with you.
Okay. So I do want you to touch on though the liability, if you will, of that. Is that something
that you saw in project management? Because you might have been more of an employee structure,
not necessarily a 1099. But how do you feel about taking that risk management mindset and
realizing now, okay, well, this is my book of business. The buck ends with me. And it's my
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2025 your most impactful year yet. I've definitely lived and learned a little bit. I've made some
hiccups, mistakes along the way, but what I've learned is I do like to document everything,
both in project management and the travel industry. When you're signing up and starting a job,
you have a contract in place. The contract outlines for you exactly what your scope of services is,
what you are responsible for. And honestly, with my clients, I do the exact same thing. Any client
that's starting out with me is there is an agreement in place, and it does outline the exact services
that I provide and the services that I don't provide. So while the passport example was a
little bit of a unique situation, and I don't necessarily do that and provide that in my scope
of services, if for some reason something were to happen and fingers are pointed back at me,
I do at least have that agreement in place where I can say, hey, I was trying to help my client out,
but here is my scope of services. And this is what I provide just because I do have to keep
myself covered and I have a reputation in the industry and I want to keep that positive.
So I like to have an agreement in place so everyone is on the same page about what I can offer.
Now, do you actually individualize each agreement or is it a general terms and conditions that you
have someone sign each time? Because I'm thinking of more of like a construction agreement. It's
specified for each project. What does that look like for you in your process? Typically,
if you are a new client of mine coming on board, it is a pretty general terms and conditions. However,
if you have a more detailed trip, whether that be two or three weeks in Southeast Asia,
a couple of weeks going all over Europe, those will require some additional terms
that be put into the contract. So in those situations, I do have a little bit more of like
an amendment that's attached to that agreement that outlines some more of those specifics.
Wow. Okay. I've never really heard of that before. And I love that because when you do
take on a very high ticket complex long-term trip, it is very much like construction in that way.
You are setting building blocks and you're working towards something. So I can see how
having a more specific set of terms and conditions for each trip, especially potentially if you have
a different service suite and you're actually putting in there like you've chosen this level
of service, I can see how it would make a lot of sense to get that even clearer than just a
general terms and conditions. Let's talk about process. Sure. Project management is formulaic.
There is a reason that people have to test out of it and it's a true certification. It's because
it is a tried and true set of parameters on how things should be executed for the best efficiency
possible. So let's talk about how that framework and understanding that framework from a project
management perspective set you up for success with creating trust with your clients.
So I think the biggest thing before you even jump on that pre-initial call with your client,
in the construction industry, before we build any building, we like to walk the site. We like
to become familiar with the soil conditions, the environmental conditions, any unforeseen conditions
around us so we can fully understand what we're getting ourselves into before we even get into
the ground. So similar to that, I'm the type of person that likes to do as many site visits
and familiarization trips as possible so I can understand each hotel. Last month, I was in
Italy and over the course of 14 days, I was going to as many hotels as I could to understand the
hotel. What are the types of rooms, the accommodations, the services, the amenities, what they offer,
taking notes, taking photos. So then when I do have the call with the client, I can say to them,
"Okay, I've been here. I understand it. This is the type of hotel that I want to recommend to you."
Now, that's not going to happen for every single trip, but I think through those site visits and
becoming familiar is a really great way to set expectations with the client early so they know
early on what to expect going into the trip. So that's kind of like the first piece that I like
to do. And then from there, I do like to break the trip up into blocks. So okay, we have the initial
call from there. After you're signing the agreement, I like to book accommodations. We're going to work
together to get your hotels secured. From there, I then like to deal with the transportation piece,
flights, transfers, trains, private boats, whatever that might be. Get that done. Okay, from there,
then I like to work on the experiences. So I like to outline that in kind of different
buckets for the clients to see all of that so they can clearly understand the process going
into it. And then along the way, just providing visibility, open communication, my professionalism,
feedback answering questions, and just collaborating with them and again, knowing that
I'm their partner in this and that we'll be working together throughout the process.
Okay. So how are you laying this out for your clients? Do you actually, those blocks that you
were talking about, do you present those things in stages or do you present them all at one time
but kind of explain the why behind them differently? What does that actually look like to your clients
when you've done an intake call and now you've created the proposal? How is it being presented
to them so that they do have that understanding? So most of the time, I do like to present it to
them in blocks and I do communicate to them, okay, next steps are going to be accommodations,
book those transfers experience, so on and so forth. There are some situations where that
doesn't always happen, but I have found, and everyone might not agree with me on this, is that
when I present a proposal to a client that lists all the accommodations, the transfers, the 10 to
20 different experiences I can offer, it tends to be overwhelming. And then I find we're spinning
our wheels and looking at, okay, well, the boat says we're going to go to Capri, but I really
want to go to Ischia and I'm like, we haven't even booked the accommodations yet. So I like to really
just clearly take it step by step so we don't find ourselves in a situation where we're going down
this little hole of talking about these minute details when we don't even have the big blocks
booked yet. So interesting. I used to do something similar. So what I would do, I actually did not
have a planning fee up front, and it worked really well for me for that season of life.
I was right around 30, so there were a lot of honeymooners during that time, and my service
that I would showcase my value with is I would plan your trip from a skeleton perspective on a
complimentary basis. I did include the logistics, so I would say I'm going to include air,
transportation, and hotels. We're going to focus only on those key foundational components,
and then should you want to upgrade your service to a concierge level, it's XYZ per day, and then
I can get into the itinerary items, or I can even send you links because this is more of a budget
conscious time period and how that I'm talking about. I can send you my links and recommendations
through Viator, a project expedition, whatever outsourced wholesaler you want to utilize during
that time for the tours and experiences that I recommend in each destination, and it worked
incredibly well because even if they didn't upgrade, I was still making commission on those things.
Exactly, right. I'm not saying that's necessarily exactly what you're talking about, but I really
like that you do have a different approach to the rollout of the presentation because it allows
people to focus on what you want them to focus on, and I agree with you. When people have too many
options, they get analysis paralysis, and then you're just focusing on the wrong things, and I
find that when people are overwhelmed, they start throwing options at you that they've found online.
Yes, my friend recommended this, yeah. I'm like, no, no, no, no, let's focus on the task at hand.
Let's get low of the itinerary down first. I really find that interesting, and my question to you
is especially in transportation because I'm listening to this, and I'm like, so unique,
clutching my pearls, are people freaking out when they hear the transportation costs as a bundled
rate after you do the hotels because I might make hotel selections in a more conservative way because
I recognize the premium that transfers will cost. If the transportation comes after the hotel
selection, it might be a sticker shock of this snowball effect. I do full transparency. I do
get pushback from clients on certain transfer pricing, experience pricing, whatever that might be.
What I try to do to get ahead of that is on my initial call, I tell them, hey, I can work with
you to book your experiences, your transfers. However, I only work with a select group of
suppliers and vendors within that destination. They're based in that destination. They are fully
vetted. They're one of my trusted partners. I know I can count on them and I have full confidence
in them. Because of that, these partners do come sometimes at an added cost, but I always say that
to the clients before they even sign the agreement. Now, I can say that and they can still come back
and say, wow, these were a lot. If that is the case, kind of what you were saying is sometimes I do
just put them in touch with the hotel concierge because their pricing can sometimes be a little bit
more cost-effective. I never recommend ubers or taxis or anything like that to the client,
but I do say, hey, in most cities where you're going, this is still an option. I want you to
be treated like a VIP 5-star, but this is still an option. But I just, again, try to over-communicate
all of that to try and minimize any of those surprises. What I'm hearing you say is you're
managing expectations before it ever gets to the point of decision-making so that they're not upset
that they've gotten in too deep and then they're like, wait, you can assure them because you've
said, I am managing your budget. I knew this was coming and I wanted to prepare yourself accordingly,
but it is done in phases. I think that's where that budget management really comes into play is
you know what the next building block is going to be, how much that round of building the trip is
going to potentially cost. You can guide their expectations on the first stage so that when
they get to the second, it's not derailing the budget completely. Exactly. I think one thing
that was drilled into me so much in college and in project management was over-communicate,
over-communicate. And it's just to me, that's just what you have to do.
I mean, this is what I wish every supplier would understand. And I know there's a cultural difference
many times. A lot of suppliers, they want to give you an answer when they come back, but that can
cause a delay of like three days. But to me, even if your response is message received, I am looking
into this for you and you can expect to hear back from me within two days. That is appeasing my
frustration. I won't even get to the point of frustration if you just communicate that. So
that's the takeaway here is whether you're the advisor or the supplier, just managing that expectation
for your client, it makes life so much easier. No one gets to the point of frustration if they
know it's coming. Exactly. I'm working on it. I will get back to you an X amount of time. That's
it. Okay. So with that being said, we're talking about setting timelines. And I kind of just led
right into that by giving this finite timeline because I liked giving myself a deadline. It
allowed me to hold myself accountable for following up with someone or following up with,
whether it be the client or the supplier. So even if I was saying, here's your proposal,
if I haven't heard back from you in three days, I'm going to touch base. I liked those defined
deadlines because it made everyone understand the sense of urgency and the domino effect of how
responses were impacting the timelines of the trip itself. So can you talk about managing
expectations from start to finish with a timeline focus structure? Sure. Again, just kind of looking
at the initial console, the initial call that I have with the clients. That's when I'm outlining
for you the timeline, the schedule, what your trip is going to look like from the moment we're
having this phone call right now to the moment you're back and I'm touching base with you on how
was the trip? Please give me feedback. So I like to outline that step by step. Once I have the
initial call and learn from the client, this is what they're looking for. And I say to them, okay,
you know, I have this agreement, I ask you to sign. Once you sign that, I give them amount of days
that they can expect the timeline. So if I'm in a busy, crazy season, sometimes it's a little bit
more. If it's not as busy, sometimes it's a little bit less. But I always like to tell them, you
know, in three, four, five days, you're going to see this proposal for me. So right away, they know
to look out for that. Once that proposal is then sent to them, I do always like to say, and I'm
sure you know this too, inventory and pricing at hotels fluctuates sometimes by the hour.
So what I've learned is clients don't want to hear that when they get a proposal from you and
it's $10,000 for a hotel and they don't give you a response for 30 days. They want to know that
that's still $10,000 for that hotel. And that is the one thing I overcommunicate in my emails that
this is not guaranteed. Even from the moment that I send you this email, this could change at any
moment. And once you are ready, please let me know your exact selections and I will then pull a final
number. So I do try and overcommunicate that piece as well. You know, I try and be transparent.
Hey, you can go on the hotel website and check my pricing if you're unsure. I'm quoting
the bar rates on the hotel website, providing those regular updates to your point. Hey, I got
your email. I need a little bit of time, touch base. I'll respond back to you. Clear communication
follow-up. So just outlining all of those steps and the timeline in an initial phone call and then
along the way I have found has been really helpful with clients. You know what I was thinking as
you were speaking was this to me is the language of a high-performing professional, which in turn
makes me feel like you attract high-profile professionals into your circle. Do you find
that the majority of your clients are really professional audience? Because I'm immediately
thinking here, if someone is an engineer, they're going to appreciate this approach so much. If
someone is a lawyer, they're going to appreciate this approach so much and they're not taking your
time for granted. They understand that there is a process in place. It's formulaic. It's consistent
and if they work with you more than one time, they know exactly what to expect because it's
consistent and you've created the process to be consistent. So I want to pause and allow you to
talk a little about how this has helped you attract a certain type of audience. I would say in the
beginning when I was growing the business, I launched my Instagram page and so a lot of my
business was from social media. And on social media, you're going to find everything. Yeah.
And when I'm starting to grow the business, of course, I'm going to take any lead that comes
my way. But as the years went on and that phased out a little bit and I did find that core group
of people on social media, many of which are very local, most of my business is Boston, New York,
New England based. They were then referring their friends and family who thought very similar
to them. And I slowly started to curate this group of people that are very like-minded like me,
understand the process, like you said. And sometimes I hate to say it, but sometimes maybe
our closest friends and family members are not the best fit for us. And of course, I want to
help everyone out, but I tend to gravitate towards those clients that I work the best with. And in
turn, they tend to gravitate towards me more. And we tend to just have such a better working
relationship. So I do have a lot of repeat business now that I think we're very aligned
on the same page. And it just makes it so much easier, I think for the both of us.
Do you find that your approach allows you to implement boundaries with your clients more?
Yes. And I will be the first to say sometimes I do need to do a better job of implementing
more boundaries. I'm also very much a people pleaser. And being in the construction industry,
the client is always going to be right. It's yes, no problem. We will make that work.
We'll find a solution for you. So in this industry, even if a client is kind of expressing
something we're in my head, I'm like, I don't know if that makes sense. Or okay, they're reaching out
to me at nine o'clock at night when I do clearly state my business hours. It's a big client. They're
spending a lot of money with me. I want to please them. So sometimes I need to do a better job of
setting boundaries, but I do think I have the processes in place that I can set those boundaries.
And I think if you have the processes in place, many times it doesn't come to the
9pm phone call unless it's a trial emergency because they understand that you're treating
your business like a business. I understand that in any business as a business owner,
there must be some point of flexibility where you serve your customer over your comfort zone.
That's just something you need to keep in the back of your mind. If you own your own business,
is there's going to be a time where the customer's priorities do come first and as an entrepreneur,
that's a decision that you have to make is, one, am I willing to make that sacrifice? And two,
if I'm not, then I either need to reevaluate what I'm doing to either get ahead of this
or change what I'm doing. Or I need to make it clear to that person that they are no longer
my clientele. But if that's your target audience and you want to make them happy,
then there are going to be some sacrifices along the way. I am the first to say I'm too rigid.
I have recently, over the past month, had some really incredible interviews for this podcast
that have made me realize, wow, I limited myself in many ways because of the rigidity that I had.
I think it served me incredibly well because I was leading a team and I wanted to lead
by example and I didn't want them to feel like they had to sacrifice their nights and weekends,
et cetera. But I swung the pendulum too hard. I gave everything in the beginning and then
I got so burnt out that I shut down. So that's what I would say is if you find the balance that
works for you in the beginning, you don't have to be so rigid because you don't get so burnt out
that you just emotionally shut down. So it sounds like it's working for you how you have it. So to
me, it's all about a balance and the lifestyle that you want to create. And if it works for you,
then it works for you. I would love for you to talk about some tools that have been tried and
true for you and that have worked to allow you to implement these processes and to maintain
that level of documentation that allows you to truly treat this like a project.
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implementing strategies that work now back to the episode. I guess first and foremost for CRM
software, you mentioned it as well like travel joy, I could not live without. And it might also be
because how my mind works, but what you were saying about having the inquiry block, okay,
every day I can see who are my inquiries, I can see who I sent a proposal to, who's approved it,
who's traveling. It's just so easy for me and I don't know what I did without it prior, but it
keeps me very organized. So that's kind of my go-to. I can manage client agreements on there,
client preferences, credit card information was secure, credit card information, whatever it might
be. So everything is there. So that's kind of my go-to and my platform I'm using all of the time.
And then from there, I also use access. A lot of people might also use Trabify, which I've used
before, but access is great because you can build your day-to-day itinerary in there for the client.
It updates regularly, flights sync, which is really great. And then we also have an app
that the client can put on their phone. And so when they're traveling, they can see every day
what they're doing, where they're going. And then they can also flip to the documents tab that has
all of their hotel confirmations, train tickets, whatever it might be. So it's a one-stop shop
for securing all the documents for clients. So I've gotten really positive feedback on that.
That's been wonderful. I use Canva for more of my marketing purposes. I have my whole brand kit
loaded into Canva. So when I am creating material for social media or for clients,
I can just put my branding right on there, which is really great. Two others is I use Seon a lot,
the commission tracking software base that's through our agency. That's been really helpful to
manage when I can expect a commission and if I've received a commission. And then also having a team
behind you, as I've grown my business, I need additional help and I need more resources. And
I now have a team and I have a sales coordinator that keeps me in line and does a lot of the
back of house business that really allows me to sell. Because at the end of the day,
if I want to make my business successful and profitable, I do need to sell. So having those
resources behind me has really allowed me to grow and become successful within the business.
Is your team local to you or are they remote? Local to Massachusetts.
Are any of your team selling or are they truly support roles for you?
Yeah. So I have a great sales coordinator that works for me. So right now, her role is just
sales coordinator. So working with commissions, invoicing, I do have her working with the clients,
kind of those more detailed itineraries working through experiences that they want, transfers
that they want. Right now, that's kind of just the role, but eventually I do want to grow into
having her sell travel and being a team member, that is my goal for the future. And I've kind of
started to map out a plan, you know, how I can do that. Amazing. How did you decide that it was
time to hire? Probably working way too many hours and sitting here at night and my husband's like,
so are you going to get off your laptop anytime soon? Or, and I did realize that if I want to
maintain a healthy personal life and relationship, I do need to start setting some boundaries and
adding in some additional resources. So I love my job. I would work 20 hours a day if I could.
That's also not healthy. So by bringing in additional staff to help me. And I think it was
about, you know, almost a year ago at this point that I was like, okay, I'm at the point where
if I want to grow my numbers, I need to bring someone in. You're right. I think there is a point
where you can only do so much and you either have to find a way to support those post intake call
steps, like maybe past point of deposit, you've got a client experience manager or you outsource
marketing. You cannot be everything to everyone. It's just not possible. It's not scalable.
There is a limit to how much one person can produce. So you have to make a decision of,
am I going to grow my team? What is that going to look like? Or what can I outsource?
And many people choose independent contractors, but then you have to recognize that they could
go elsewhere without any notice because they're an independent contractor. And they might be
intertwined with your brand identity and have to find another brand identity. They might want to
be their own brand, or you can hire employees that are then very loyal to your brand. And
they truly are just detail-oriented, amazing humans that support your ability to do the
piece of the business that you love, like hopping on a call and talking about the potentials. Then
saying, "Hey, let's go through this DMC. Here are my notes from the intake call." And you hand it off,
and there's this supply chain after that. There are so many great ways of doing business.
I don't want anyone to think there's one-size-fits-all in this industry. And I love that you do have
a little bit different approach because so many people right now are looking at sub-ICs,
and then how do you control the risk management there?
Right. The virtual ICL, all of that stuff, I agree. And speaking of risk management, that's
where my mind goes immediately. If someone's an independent contractor, how can I control the
chaos? I know. And I like to control things, whether that's a pro or a con. I do like to
have some sort of control around everything. Well, in this industry, we can only control
so much. So, it does feel good to control the things that you can. Exactly. Right.
Okay. So, when you have so many systems and processes in place, to me, it does allow a business
owner to be present in other areas of their business, not just in the client experience.
How does having a defined structure and also a defined support team allow you to bring in the
passion and the creativity that makes every trip special to your client and then allows them to
come back and return to you time and time again? I think by having these processes in place, which
did take me some time to develop and tweak them a little bit, but now that I have them in place,
it does allow me to think more creatively. So, okay, when I go on the call with the client,
I already know what I'm going to tell them as far as timelines and my typical terms and conditions,
et cetera. But now, let's get into some of the more fun stuff. And an example I wanted to use was
everyone can plan a romantic dinner on the caldera in Santorini, right? But taking it and
thinking a little bit more creatively and getting to know the client, maybe it's a honeymoon or
an anniversary or something like that. I have a supplier that I work with that can plan this
beautiful private luxury picnic at an undisclosed location you won't know until you get there.
On the caldera, you have waitstaff dedicated just to you. You have the handcrafted linens and the
pillows and the candles. And you have the local wines from Santorini and the fresh seafood. Maybe
we get a professional photographer to capture the moment. That really takes that romantic dinner
that everyone can advertise and elevate it to the next level. So, that's one of my favorite parts
about the job is, okay, now I don't have to think as much about these processes because I have them
in place. So, let's talk about some fun ideas. I mean, you could talk to me about Italy all day
long and we can get creative as creative as you want. But I really just like doing that because
the client you can see is get so excited about it. Oh, we can do that. Oh, I never thought about that.
And that's what makes the job fun. And I just think I have a lot more time now to focus on that,
which maybe makes me as an advisor stand out too and ultimately helps me sell more.
And I also think that when you say picnic on a caldera, you don't even have to disclose all of
those details. You can say like a really beautiful picnic on a caldera and it almost like downplays
it a little bit. They're going to be excited anyway because that sounds beautiful, but then they get
there and you've got a floral arrangement and they have this dedicated staff and they're like,
wait, I did not know this is what she meant by that experience. I really love that. I also
love that having processes, templates, systems in place allows you to do the piece that you love
to do. When you free your brain up from the mundane administrative pieces of the job and
you're not just operating from a place of reactivity in your inbox, it does allow you to serve your
clients so much better, so much more creatively. And that's what gets people to come back to you
because someone might come to me for a Santorini trip, but if it's a run-of-the-mill Santorini
trip because I have so many clients right now that I'm like, yes, this is good enough. Get it
out the door. Well, that was their honeymoon. Are they going to come back for their anniversary or
maybe they're just going to do a single stop in Antigua for their anniversary or so they're not
even going to think of me. But if I helped translate their vision into something spectacular,
they might be like, you know what, this is a special occasion. We should call Jennifer.
We should call Kara. Yes. I want anyone who feels like their book of business is getting away from
them a little bit to hear this loud and clear that if you have a chance where there is a lull in
business, don't think, how can I get more clients? Think, how can I serve my existing clients more?
How can I take this week of no inquiries and really dive in, audit my trips, make sure I'm not
messing anything up? First of all, really audit the trips so they're correct and you have all the
details you need, the flights are right, but also maybe a little surprise and delight along the way
so that you don't have to spend money or time marketing as much because you start to really
develop these entrenched relationships with your clients because they come back to you for every
celebration and trip throughout their life. I agree. And having those little moments and sending
an email to a repeat client, how are things going? A handwritten note, I've done that. And
you'd be surprised at how many people I might not have heard from them in six to eight months.
And they, oh, actually, glad we heard from you. We're actually planning this trip. What do you
think about this? And that goes a long way instead of trying to reach out for more clients, like you
said. Do you market yourself as a project management-based professional on your website
anywhere? To me, if I saw that, I would be like, yes, she takes my trip seriously. I would use her.
So can you share how you've actually woven that into your marketing plan?
I love that you say that because when I have these calls with clients, I do talk through that a
little bit. But I think there is room to push that and grow that a little bit more. I have
this great website. It's awesome. But maybe putting in something like you said about the project
management approach and how I approach things would go a long way. And so I think having this
conversation with you today has really given me some time to think through it and think about
how many advantages there are. And it's definitely something I'm going to implement into my marketing
a little bit more moving forward. I love that. I think it could be part of your brand,
really. I actually met a newer advisor at E3 this past year. And he's like, I came from
project management, but I really love the teak approach with the templates because it really
speaks to my love language of how I want to run my business. And I was like, you have to start
marketing yourself as the guy who treats every trip as seriously as a project management situation.
I just feel like that gains a lot of respect. And because there is that lower barrier to entry
in the travel industry, when you say that you have been credentialed for something
and you have a professional background and something that runs very parallel,
it just adds a level of credibility that people could really respect.
Yeah, I love that idea. And I will probably be using that. So thank you.
Well, thank you so much, Kara, for being here. It was such a delight to meet you and to hear
all about your approach. And I'm so grateful that you shared your wisdom and your experience
with us today. Well, thank you for having me. I really appreciate it. Absolutely.
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