39: Getting Started with Outsourcing featuring Jill Gum • Dolly DeLong Photography

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I'm Dolly — a Nashville based branding photographer for creatives & a systems + workflow educator (and Podcast Host) for creatives who want to be more streamlined with Dubsado and Systems. I'm here to help you look awesome (for your photos) & feel great about workflows!

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39: Getting Started with Outsourcing featuring Jill Gum

Episode 39 of the Systems and Workflow Magic Podcast with Dolly DeLong Featuring Jill Gum

Hey friends, welcome back to the Systems and Workflow Magic Podcast! This week I am so excited to introduce you to Jill Gum, of Jill Gum Photography & Education. She and I are covering all things outsourcing: how to prepare to outsource and all of the actual mechanics of bringing a new person into your business. There is truly so much to consider when outsourcing work in your business, and Jill has some of the best advice to set up your systems for success. I cannot wait for this conversation!

The Systems and Workflow Magic Podcast is brought to you by Dolly DeLong Education. This is a podcast for creative business owners who want to learn tangible steps to automate their business through workflows, systems, tools and strategy in order to go from scattered to streamlined with purpose. Because even muggles can become automated wizards.

Meet Jill:

Hey there, I’m Jill, and I teach women how to shoot like 6-figure photographers and build successful businesses on their own terms. I am also a mama to 3 amazingly effective alarm clocks, wife to my favorite person (and personal chef!), and a past high school choir teacher. For the past 9 years, I have been photographing joyful couples on their happiest day, and even 115+ weddings in, I still get that excited wedding-day-buzz before every wedding I shoot! But I chose hard paths when building my business, and I love helping others avoid making those same mistakes while finding their best version of success for their businesses and families. I empower my students to take beautiful, meaningful images in any situation as they create a business they LOVE, and a business that provides and thrives.

Review the Show Notes

Get to know Jill Gum (1:36)

How Jill got started with her business and outsourcing (5:28)

Your first steps with outsourcing (7:58)

Putting your systems in place in order to outsource (23:13)

The mechanics of outsourcing (32:02)

Stay connected with Jill (38:48)

Mentioned in this Episode

Get 20% off Outsourcing for Creatives: use code SYSTEMS PODCAST 

Jill’s Free Gift: Simplifying Outsourcing with Trello 

Episode 9 

The Legal Paige 

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Review the Transcript:

Dolly DeLong
Welcome to the systems and workflow magic podcast where I help entrepreneurs go from scattered to streamlined in their creative businesses. I’m your host, Dolly DeLong, a wife, a mom and a photographer turned systems educator. Join me every week as we have conversations centered around creating tactical workflows, and automations in your business. Now, let’s make some strategic workflow magic. Well, hey there friends. Welcome back to another episode of the systems and workflow magic podcast. This is episode 39. And we are going to be covering the topic of outsourcing with the amazing Gil gum of dill gum photography and education. She has a lot to share about how to get started with outsourcing. Because she is literally the outsourcing queen or at least I’ve deemed her that in my mind, because she is always super efficient with all the things and very organized. And in my mind, this is all in my mind, everyone. I just want you though. But I’m so excited to have her on the show and on the podcast today. Because I know this is a topic that many people either need to hear or they want to learn about or they’re too afraid to start diving into this topic. So I want to take the overwhelm out. And I want to give you some sort of strategy and system to go by. So Jill, I’m so happy to have you here. And I know you’re going to cover a lot of foundations of outsourcing with my audience today. But before you dive into that, do you mind sharing a little bit about yourself, who you are, who you serve, just like give us the whole scoop.

Jill Gum
Hi, Dolly, I’m so happy to be here. Thank you so much for having me. It just I’m so thrilled to be on this wonderful podcast of yours. I really thank you and I’m so honored to be a guest. So I am a wedding photographer and brand photographer in central Illinois. I also shoot families newborns, I shoot a little bit of everything. I never fully specialized because I just I just love taking pictures of people. And before I did all of that I taught high school choir for years and years I met my husband while teaching and that kind of previous experience in my life has led me to dive into education within my business as well over the last five years. So I love to teach moms how to take better photos of their kids beautiful photos in any situation, and potentially turn that into a business that helps provide and helps their family thrive. So that is what I do in the education world. I became a photographer because of being a mother, I had always loved photos as a kid took darkroom classes in high school, I was really into photography, but just had never kind of made the jump to buy a fancy camera until I had my first baby. And then we were well I think my husband was terrified by how many family sessions I was going to cause him to pay for in the first year of my baby’s life. So he’s like, maybe we should just get a camera and we bought one and I fell in love immediately and started a business maybe about seven or eight months later, I just dove in. And I’ve just loved it ever since. So I feel like that background has really given me a passion for working with moms and helping them in business owners do things in an easier way than I did when I was beginning my business.

Dolly DeLong
And just for context for everyone. How old is your oldest?

Jill Gum
My oldest just turned 10. And then I have an almost eight year old and a four year old.

Dolly DeLong
So everyone listening? Jill has been at it for over a decade. So she knows her stuff when it comes out sourcing. All right. Fun fact about Jill. So Jill and I were in a mastermind together in 2021. And one of the best things about this mastermind was the relationships I formed from that experience. And I have been loving keeping up with Jill for well now like when this airs is going to be like almost two years ago, and I or a year and a half ago. And I love referring people to Jill because like I know she lives in the Midwest, but I refer like if I get like a client who’s wanting to learn about how to get started with photography, I refer them to her because again, she knows her stuff. She’s been at this for over a decade. She’s very consistent, she’s professional, she’s joyful, and she’s really fun to be around. So anyways, Jill, you all are in for a treat because Jill has so much wisdom.

Jill Gum

You’re so sweet, Dolly.

Dolly DeLong
It’s all true. It’s all true. So I say let’s give the people what they want. Let’s talk about some strategic steps in getting started with outsourcing for your own creative business. I know for me personally, this is something I have dragged my feet doing but if you listen to episode nine, I shared some of the first steps I had to take in order to better scale my own business. And one of the steps involved outsourcing. And so after listening to this episode, go back and give it a listen as well, because it might give you even more ideas on how to outsource areas of your own creative business. But since we have the queen of outsourcing herself on the podcast, Jill, I want you to take it away without sourcing for creatives. So where do we begin with this beast?

Jill Gum
This is such a good question. I feel like I wouldn’t mind sharing just a tiny little snippet about how it began for me, because I feel like I feel like we’re gonna get into how other people can can kind of decide it for themselves. But for me, I continued with my teaching job for the first few years of my business, I was teaching part time, but as a high school music teacher, that really means full time with part time pay. So I’ve got this other full time job. I’m a new mom, a semi new wife. And now I throw in this side gig side hustle that I loved. But within the first couple years, things got very busy very fast. And of course, like everybody else, when I started, I knew the art side, I did not know much about running a business. And I feel lucky to say that a lot of that comes naturally to me, I like to mark it that that stuff is all easy for me. But I feel like just figuring out how to do it on how to put it all together took me a long time. So by the time I decided I wanted to start adding education, I was just at kind of beyond a max capacity with my schedule. And that for me is where outsourcing came in that I needed a way to make some margin in my business if I was going to start this whole new area of my business. And the only way that I could do that is if I started to hand off tasks that did not have to be done by me. Because if I was going to start educating in my business that had to be me, I couldn’t hire somebody else to educate people on my behalf and my business, right, it had to be me teaching what I knew. But there were plenty of things that I was doing, that I did not have to be doing. And that to me is kind of the heart behind all of it is figuring out what those things are. And we’re going to talk a little bit about how to do it. But just figuring out what those things are so that you can create margin, either in your business to do new things, or in your life, if you’re just overworked and don’t have the time in your personal life that you want and need to be working a little bit less. So that’s how it started. For me. I started outsourcing about six years ago and have expanded it so much at this point that my virtual assistant does about half of the work hours that go into job and photography every week. So it’s a pretty huge part of my business at this point tonight, I can’t wait to dive in further.

Dolly DeLong
Man chill, I’m so excited to learn from you. And as you can see, I’m most likely going to be taking notes that are a little Google Doc that we are sharing between us. So do you mind sharing? Like, what are some first steps that you recommend? Like when creatives are looking at this daunting task? It’s overwhelming, it overwhelms me. And so like, what are some first steps you recommend?

Jill Gum
Yes, that’s a great question. So one of the things that I tell my new business students a lot is that it’s very easy to think, Oh, I’m not ready for that yet. I don’t have to outsource yet. I’m just going to wait because I because I’ve only been in business for a couple of years. And honestly, I think that outsourcing as as soon as you possibly can, and we’ll talk about kind of what qualifies is that is the best idea. Because if you can start to offload small tasks in the beginning, it’s going to make it a lot easier than if you’re at a point where you’re already doing so many things in your business and have to figure out how to offload a ton of things at once. So just even as a photographer, and I know you have a lot of other types of business owners, but as a photographer, I’m not just shooting pictures and editing them and delivering them, right, as we talked about, as a small business owner, I’m also marketing and I have to sort of become my own web designer. And I also, gosh, when I list out all of the things that we have to do as small business owners, there’s just such a huge amount of things, I have to become a salesperson, I didn’t really know that I was going to be doing that and so many tiny little things. So if you think about all of those different hats that you have to wear, not only is it unlikely that you’re going to have time to do them all very well. But it’s unlikely that you’re going to be particularly gifted in every area. There’s the finances of running a business and taxes. I mean, there’s just so many different things. I know I’m not good at all of them. And I bet most people are not wonderful at every one of them. So when we start to think about outsourcing, we want to think about what things don’t have to be done by us. But we also want to think about what things do we not want to do because we’re just not gifted in that area. And I’m going to break some of that down a little bit a little bit as we keep going But I just feel like starting small early in your business is the best way to do it. So if I was to define when that is, I think you probably want to be profitable before you go ahead and start outsourcing because obviously you’re going to spend a little bit of money to outsource. And I will be honest, everybody’s definition of profitability is going to be very different. I actually think Dolly’s in mind might be quite different, because I think dolly is extremely smart and intentional. Well, I’m just thinking about it.

Dolly DeLong
Yes, I paid her to say, No, I’m just thinking.

Jill Gum
Profit first training and all of those things like you have dove deeper into that than I have. But but for the purposes of outsourcing, I feel like the easy definition of profitability is when the amount of money you’re making is worth it to you for the time that you’re working. And that’s going to be so different for everybody. If I’m 22 to 24, and unmarried, it might be worth it to me to work 60 or 70 hours a week in my business, and whatever I don’t know, I just I feel like the actual level of your profitability is really very personal, depending on what your needs are, and what how much you want to be working how much you want to be away from whatever work takes you away from. So it’s hard to give any sort of number, but you’ve got to be I mean, obviously paying yourself, and you have to be no longer using any. So I mean, if you happen to be using loans, teacher business, or I think you have to kind of be out of that area, in order to be profitable. And then it just has to be a spot where you are comfortable with with how much work you’re doing versus how much you’re getting paid. And I feel like once you are there, and then once you feel like your workload is a little bit beyond your capacity. So that might mean again that you are doing more work hours, then your pay is making you feel is worth it. That’s when you want to start off sourcing. And in the beginning, like I said, it can be so small that it doesn’t even it’s not, it’s not like you’re giving away just huge, huge parts of your business if you start small and early on in your business. So yeah, I’m just really passionate about people getting started before they’re so far in and so buried by work that it feels. I mean, I remember a little bit even when I started outsourcing, it felt like a job to figure out how to outsource. And at that point, there was nobody teaching about it. I mean, it was hardly even being talked about. So like now I have to find hours of time to figure out even how to outsource which is why I’ve created some resources about outsourcing because I know that struggle for me to figure out how to do it. And if I had just done it a little bit earlier, it might not have been such a struggle, because I wouldn’t have been so buried in work already. So I think those are kind of the first few things you want to be profitable. And then you want to be at that point where you feel like your workload is a little bit beyond your time capacity. And then the last piece of knowing that it’s time is that you really really need to be organized in the areas you want to outsource, you have to have systems in those areas. So there’s there’s kind of two parts of that the first thing that I like to recommend, and I would recommend this to everybody who’s listening, whether you think you’re near to a time of outsourcing or really far away, I recommend that for the next maybe two weeks of work time that you make a list of everything you do just have either a Google doc up or a notepad next to you. And every time you start a new job, you just begin right away making this list of the tasks that you’re doing. Because what you can do with that list, once you’ve kind of gone through a couple of weeks of work and covered most of the different hats that you wear in your business, most of the different things that you do is that you can then start to decide what you have to do and what somebody else could do. And in addition, what you want to do and what you don’t want to do, like I mentioned before, so I think that first step is to know what all of the jobs are. So sending emails, reading emails, then we’ve got all of your marketing jobs, posting on social media, list out each type of social media, prepping those posts in the first place, blog posts, SEO, I mean, the list is endless, as we all know. And you’ve got to know what all those jobs are so that you know what you could get rid of. And then of course, the next biggest key is that you have to have a solid system in each of those areas. I like to joke with my students, if for example, in whatever creative industry you’re in, if you decide that you want to outsource some of your onboarding process, your client onboarding process, and you say to your new virtual assistant, this they email me and then I email them some information back and then that I put them in a spreadsheet, I might send them a paid PayPal invoice for their deposit. Sometimes I send a gift sometimes I don’t and then there might be like some information to send them about like how to prep for whatever work we’re doing together. Good luck, your virtual assistants can what what the heck right? What am I supposed to do? So you have to have on your end kind of a pattern a system set up For those things that you want to give away, so that it’s repeatable, right, you need your virtual assistant to be able to follow the steps that you are following. And to do them over and over again every time. So that is one of the big keys, I think to kind of those first steps is that you have to be in a place where you are doing the same thing which your clients deserve anyways, where you’re doing the same thing for each client you have, or for each area, if you’re if you’re going to hire somebody, just to help you with blog posts, you’ve got to have kind of that system setup for what your pattern is, and how you start that process all the way through the end of it. And you have to have a way to get that written out or taught to your virtual assistant, I did a lot of that with just QuickTime screen recording videos. And that worked really, really well and was a simple way to make sure that I had like a recording of all of my systems that was going to be repeatable over and over again, by my virtual assistant.

Dolly DeLong
This is all like this point. One is a masterclass in itself, y’all. So hopefully, like, even if you, if you’re driving, don’t take notes. But if you are sitting still, I hope you’re taking notes and give this episode a realist. And because Jill is sharing a lot of information and just for context for everyone, like I know that I speak to a lot of different creatives who are needing help with systems. And we’re like just getting started with systems and workflows. And you can apply this to whatever business you run, you can make it applicable to your personal business. And I wanted to share my own story with with you and with Joe, like I have recently this year started saving up for working with the VA like on two very specific tasks that I do all like every week, and it takes me about three hours. I’ve mapped it out already. I’ve like done what Jill suggested I mapped it out. I have created a Trello board with all of the steps and then I created another chart listing out the steps within that step. And so I’m going to be creating loom videos and how I’ve been saving up for like intentionally saving up I’m like using air quotes right now I know you can’t see me. But this is something that I got from Shana Skidmore. She is the creator of the blueprint model. And I was a part of that. I call it like the Mastermind course with with Shana. But she taught about the importance of taking out like let’s say you have you have a VA for you hire them out for 10 hours a month, I don’t know. So you divide that into four, I can’t do math right now on top of my head was like almost like three to four hours a month, a week. I mean, and so what if she like gave this example? Like, what if you took out to like this industry standard for paying a VAs between like, lower end 25 to $40 an hour. Okay, so what if you took out, she gave this great example. And it just like stuck with me, and I started doing this. And because I did this, I now have three months saved, like I’m gonna have three months saved up for my VA so that I can onboard her for 90 days at three hours a week. And so it’s this take out $25 from every session you do like if you are a photographer, and put it aside in a savings account, and specifically label it savings account for VA or whatever you want to label it as. And so now I know exactly like a naming where my money is going. And I’m going to have that contractor specifically work three hours a week on two very specific SOPs for me standard operating procedures for me and I feel, I don’t know, I just feel like a light bulb went off when she explained it like that for outsourcing because I thought I had to be like, making 10s of 1000s of dollars per month like to hire out workers. And she was like, No, you don’t have to hire somebody full time. And you don’t have to. Somebody can work for you as a contractor for two hours a week. And on one specific task just to get started. Yes,

Jill Gum
I think that’s so wise Dolly, and I will say Dolly and I were chatting before the podcast here a little bit about kind of the timeline in which you do you do things yourself and in comparison to the timeline that you teach. When I started outsourcing. It was back in like the wild west of I think I think my virtual assistant, I did like $10 per hour in the beginning. It was crazy. And that’s not applicable anymore, as dolly said, but when I started and I don’t know if dolly wants me to get in the hole, like how do you find someone I think it’s a little different now than it was when I started because again, not a lot of people were outsourcing at that point. But I literally just thought through people that I knew that I thought would have some of the skills and dove in because in the beginning for me sort of like what Donnelly was saying, it was just these tiny, tiny steps. Now again, I was all already buried. And I think I should have done it much earlier. But I started with just some basic things like, for example, as a wedding photographer, I tag vendors in every blog post, well, it’s probably like a 30 minute job per blog post to go through and find everybody’s website or their Facebook and get them tagged in there. So my virtual assistant can do that, there’s no reason that I have to be the person looking it up, she can find the questionnaire that’s already made and do that herself. My virtual assistant can make Facebook albums for me, there’s no reason for my time to be spent adding a bunch of photos to Facebook album and writing descriptions. So many people have that skill that doesn’t have to be used. So those two things are very small. But in and of themselves, were probably an hour and a half of work per week, that then I don’t have to do. And also if you’re starting small like that, I mean, I think it’s, it’s ideal to find somebody who is going to grow with you, of course. But if you do start with Dolly, I think that’s the best option. That’s what what I luckily fell into as well, my virtual assistant had no idea about this industry. And now as a virtual assistant for other people like this has become her whole career. So she has stayed with me. But if that doesn’t work for you, for some reason, there are a lot of people you could find to could post Facebook albums for you and tag event. I mean, there are so many little easier jobs that you might have a upper teenage niece or nephew that could do I mean, there are so many options for somebody who feels overwhelmed and finding like a really well established virtual assistant, or in being able to pay for that there are a lot of things you could you could do to potentially find somebody who us very trustworthy. I feel like the trust is really, really important in this process and something I teach a lot about. But there are a lot of options for people you can find to do some of those really, really simple starter tasks, I am assuming that dolly is probably going to outsource some higher level tasks, because because she’s pretty advanced in her business at this point. But if you are somebody who’s just in your first couple years, you could still be giving up some of those jobs that really don’t have to be you and at a much different capacity, price point. All of those things depending on on where you are in your own business.

Dolly DeLong
Yeah, and this is just me like before we’d like merge into like the second point that Jill’s about to share. This is me being like overly cautious about everything, make sure that there is a contract between you and your VA or your contract, like whoever you’re contracting out the certain processes that you want help with like one to three hours a week, because you need to protect them and yourself. Like there needs to be clarity clarification. Because when there is I don’t know, misc, no communication whatsoever, or just open endedness there will be frustration, there will be frustration on both ends. And so just make sure that you are taking the time to save your time, yourself some time with frustration in the long run. So set up some contracts for yourself. And I’ll link my favorite contract shop to the show notes of this podcast episode. Okay. And there are some great contractor contracts from the Legal Paige. And I will link it there. Okay, so you guys have no excuse?

Unknown Speaker
Yes, I completely agree completely.

Dolly DeLong
So we just went over just like how to get started. So what is so what now?

Jill Gum
Yes. So the next thing that you really have to have to be prepared for I kind of touched on before is that you’ve got to have those systems in your business in place. So that you can really describe and well communicate with your virtual assistant about those tasks. In my own opinion, that means that you really need to, you need to have your full plan for your for onboarding your clients for your client workflow once they’re on boarded. If you’re a photographer, you’ve really got to have like that gallery delivery method worked out, you’ve got to have your your marketing plan settled for each individual client that you take, what are you doing, to further market what you do for them, and therefore what you can do for other people, all of those things really, really need to be well structured and well organized, so that you can easily communicate and share those jobs. I know that when my virtual assistant, like I said she just did this for me kind of for fun, and then over time, started her own business and took on a lot of clients. And in the beginning, I know that she struggled a lot and I don’t know any specific details, of course, but I know that she’s struggled a lot with getting very clear cut instructions from some of her from some of her new clients about what they wanted her to do. And the more clear you can be the better return you’re gonna get for your investment. And I feel like one of the things that that I hear a lot from from my students is that they’re really, really nervous about handing over their work. They’re nervous about handing over their baby. You know, this thing that you’ve built and worked on can somebody else actually do it as well as me and I totally understand that feeling. I think for me, that hold up came the most in the idea of an editor for my photos. Um, just because that felt so personal, I will just say, as somebody who has now been outsourcing editing for five years that I got over it very fast once I realized, return on time on on it, and yes, somebody else can match your photos, I swear they can. But, but it is really hard. And it is it’s hard to trust somebody enough to invite them into those processes. And also to be able to take that little step back of like self awareness that occasionally things are not going to go exactly the same as you would have done them. And that’s okay to your business is going to be fine. If one Facebook album gets posted missing some tags, you know, everybody’s gonna live. So I feel like you just you have to get a little bit of perspective in place so that you so that you can just be ready to give those tasks away to somebody else who is just going to do is just going to do an amazing job giving you some margin back in your life.

Dolly DeLong
I was just gonna say I’m like jotting this down in my notes, too, I really think it’s important. Even if you have  your systems in place, and you have like set processes and workflows, that’s great. But it’s going to take time to actually train the contractor, the VA, whoever I would say like give it a solid 90 days, like if you are intentional about like you’re in it to win it like this is the long haul and you want this person to work with you or you want the system to be handed off, or this task to be handed off, then you you have to like just know going in like this is going to take some time, it’s going to take a quarter to at least train this person, and they are going to mess up and you are going to have to be okay with communicating with them. Not like I am already preparing myself to be okay with my future VA messing up on some things. Like they can’t read your brains, like they can’t read your mind. They can’t read your brain. This is not as emotional for them as it is for you because it’s your business. But you can still treat them like a human, give respect and communicate with them and let them know hey, like, um, I noticed that this link was missing. Like let’s say somebody takes over your newsletter for you. And you like have them test it out, create videos explain exactly what you want, and then trust the process. And it was it’s going to be I believe it’s going to be a growing process for you and you will, there’s a difference between a mess up and then you seeing red flags, there’s a very stark difference. So if somebody genuinely messes up and they fix it and they move on, versus somebody who constantly is not good at communicating is not showing up is like, you know, the red flags for yourself. So you will you will, you will know the difference.

Jill Gum
Yes, I cannot agree more. And I honestly talk to my students a lot about that communication piece, because I think it’s important and I think it’s important to establish in the beginning, you know, I, I speak a lot to my students about starting the relationship in such a way that there is a very open line of communication, I actually recommend to them, they set a monthly time, especially in that first quarter. I love that idea of the 90 days that they set a monthly or maybe even weekly in the beginning time that is is not specific to me handing her tasks or him tasks and him giving them back to me but more specific to just an open ended conversation about how things are going from both ends. Because if you start with that open line of communication, where it’s very easy for you to say, Hey, I noticed that you paired these image and this is a photography reference again, but compare these images in this specific way. And I actually would really rather you do this instead, I don’t really like to black and whites together, I want a black and white paired with the color, whatever it is, if you start with that, it’s so much easier to continue that throughout the longevity of your relationship. Or maybe your virtual assistant is uncomfortable with the return time for something and they just need more time. But if they feel hesitant to ask you for that, it’s gonna be a lot harder long term because those things are just going to compound. So I really recommend to my students that from the beginning you set just a weekly, five minute phone call five minutes zoom session, whatever it needs to be, and then eventually monthly once things are a little smoother to just check in and see how it’s going from each end. How are you feeling about what what you are outsourcing and sending so far? How are they feeling about the process? What can you do better? What can they do better? What are they doing well, and what are you doing? Well, just to kind of keep that communication open.

Dolly DeLong
I do want to point out that there is a difference between an employee of your business and then a contractor that you’ve hired out. So I might be butchering this again, I go to your lawyer go to somebody who knows these terms exactly. But from my understanding a contractor they can work whatever hours at whatever like time of week for you because they don’t work for your business. Yes, you’re paying them but they’re being they’re contracted An out versus an employee is working based off of the time frame that you’ve set. So make sure that you are honoring. If you hire a full time employee or a part time employee, then they work under your hours, your set hours versus if it’s a contractor. And if they can work from three in the morning till five in the morning, that’s when they want to work. Well, then that’s when they work. Okay. You don’t dictate when your contractors work for you.

Jill Gum
Yeah, and I’m gonna pop in on this really, really quick, this is a side note, but it does have to do with outsourcing. I think people get really nervous about the legality, what are we calling it the legalistic whatever,

Dolly DeLong
I don’t even know.

Jill Gum
The reality of having somebody work for you, right contractor or employee and what that means for taxes and all those things. And I that is not an area of my business that I am gifted in. And it is an area of my business that I outsource. That being said, I do believe I have learned at this point, this is not legal advice. This is just my best understanding that a contractor also works for other people. So they are like, like Dolly was saying they are not linked to your business as an employee. There’s somebody who does that work for other people with their own equipment and their own things. That’s something that was one of the differentiations that we learned that allows us to my virtual assistant is considered a contractor because she does this work for other people with her own equipment. If you for example. Uh sorry for the other photography reference, I cannot think quick enough about another good front camera reference. But like if I have somebody who’s an associate photographer, and they come to my house and pick up my camera and my lenses to go shoot a session, that probably falls a little more under an employee sort of situation because they are not using their own gear and doing things for other people as well. That might be a way to kind of help you differentiate if you start looking this up and you’re like, oh my gosh, I don’t even understand how I have to pay them or how I clean them or how I deal with taxes.

Dolly DeLong
If you are, you to your CPA, talk to your CPA because they like I’ve been talking with my CPA, you all met her on the podcast at whatever episode Jackie, love you. She’s one who has helped guide me through this. Absolutely. Yep. Let’s go on. Okay, so you talked about just where to begin. And then the importance of okay, you’re, you’re ready to outsource? Okay, set up some systems in place so that you can better train and communicate with that new hire either contractor or employee. So let’s talk about the actual mechanics of outsourcing.

Jill Gum
Yep. Okay, so I’m gonna get real basic for a minute. And you’re just going to have to pardon me. But I just think that it’s helpful to mention. So when I started my business, I of course, had to pick a way to organize my files on my computer and write it well, I think actually started with Dropbox and switched to Google Drive at some point doesn’t matter. Either way, you want to have some sort of system that you’re going to be able to access easily from different computers, different devices. And for me, now, that’s Google Drive. And that has become kind of the central hub in terms of, well, there’s a few central hubs, I’m gonna get to the rest of them. But that has become such a key important factor for us in terms of file structure and organization. So we have a shared folder. And within that shared folder, all of the different tasks that my virtual assistant does are kind of split up by folder. And then as we make documents, as I made training videos, all of those things, then went in those folders, so that she knew where to find things. I knew where to find things, we do kind of a regular cleanup of those folders because it needs it sometimes. And then we’ve got kind of that shared folder system. The next thing that I think is maybe the second biggest key other than that shared file system, is that you’ve got to have a way to communicate jobs and Dolly and I are both in love with Trello. It is the program that both of us use dolly actually I feel like showed me how to like beautify things on Trello. I’m telling you, if you’ve never seen one of Dali’s Trello boards, they are beautiful. I have just a background she has like, I can’t even describe it. They’re beautiful. You got to check them out. So we both love Trello. And that is what I use with my virtual assistant she has her own and I’m not gonna get too much into the technicalities of Trello in case you don’t know about it, that’s a whole other whole other episode. But and maybe there have you done it. Have you done a specific Trello episode yet?

Dolly DeLong
Um, I have not that I can think of. This is my, this is my let’s talk about let’s just break it all down.

Jill Gum
It’s an amazing program for yeah, I cannot well, you can pay for it. Yeah, committed enough. So essentially, my virtual assistant and I have a board, which is essentially just picture like a web page, just a big web page that has a bunch of different organizational devices within it. If you are unfamiliar with Trello, there’s no way to explain it without diving into all of it. So I’m just gonna say it’s an online system that allows us to very detail in a very detailed way flush out jobs that she has to do, it shares all of my workflows. Dolly mentioned before that she’s got her book workflows on Trello as well. You can assign tasks to certain people and label them certain ways. You can even check a little checkbox when they’re done, which I really enjoy. There’s so many capabilities on Trello that allows both of us and kind of like I have real time to see who’s doing what, whose job it is next, what part of every process we’re at. And that has been really, really key to what we’re doing, it’s so important to me that I actually share Trello board templates with my students, because I just feel like it is vital to your outsourcing to have a way to communicate those jobs other than just email or, or however you’re choosing to communicate, I think I think you’ve got to have something where you can really see all of the steps laid out and all of the systems. So I think that’s really key to having in the beginning. And then the only other thing that I know, I mean, there’s a lot of account access questions that come up with a virtual assistant. So I feel like I might as well mention that as well. I use a password program called LastPass. I don’t know Dolly, if you have anything like this, I do, I use that saves all of my all of my internet passwords, right? Because of course, we’re supposed to have them so different each time. And then it’s hard to remember them all. And that that program allows me to share my passwords with my virtual assistant without her actually knowing the passwords, so then she can access all of my accounts, you’re going to have to have some method worked out for that for whatever they’re going to need access for. And then in my particular area of work, and I know Dolly’s as well, we both use client management systems. And that’s another area that my virtual assistant has her hands in very deep in terms of all of our workflows for my clients. And I use Honeybook, I know Dolly uses Dubsado and they both have some different features and benefits to them. But I have always used Honeybook since I stopped using sticky notes which I do not recommend to you, I recommend a program.

Dolly DeLong
I have a really funny story about sticky notes. And I’ve shared this before I don’t know if anybody remembers but when I used to use sticky notes like this like reminded me Dolly, you just need to completely commit to the upside of this was when my son was one sublease was like under one he found my full workflow like on sticky notes. And he toured them off the wall without me knowing. And he threw them in the toilet. I was like, it was very hard for me. Like I wasn’t good at like he was under what y’all like, exploring? Yeah, he couldn’t control it. He was curious. They’re colorful. And I’m not gonna say it like, like on because like, oh, just in case like you have like listening ears with you because my son listens to this with me. But he I just told my husband Well, that went down. Like no, it was I fully agree, like sticky notes are pretty visually, but like get something digital for yourself because somebody something will come and destroy, yeah, you’ll lose or it’ll become unstable,

Jill Gum
like client payment reminders on sticky notes on my computer. Just horrible. It was not good, not good way of doing business, you’ve got to get a client management system, you just have to. So that my virtual assistant has access to that and is able to move things through the workflows that it gets kind of techie, when you start talking about move, move portions of my workflow forward. But that’s that’s what she’s able to do in my client management system. So I feel like you really want to kind of have that part organized as well, assuming that your virtual assistant is going to do anything with your clients. Now, like I said, if they’re only going to start with social media type work, blogging type work, like you said, newsletter type work, they might not have to have their hands in your client situation. So you might not have to have that part as well fleshed out, as you need to have, for example, a Trello board where you can assign jobs to them. So you just have to think about what you’re going to have them do. And what are the what are the full steps that they need to have well prepped by you in order to do that work well.

Dolly DeLong
Yeah, I love this so much Jill, like you’ve shared so many, like golden nuggets of wisdom. And for those of you who are listening, please like this is one of the episodes you’re gonna want to re listen to several times. And even if like you listen to it once but you still want to learn from Jill like Jill has a treat for you all she agreed to create a 20% off coupon codes exclusively for the listeners have the systems and workflow magic podcast for her outsourcing for creatives course. And so in the show notes, I’ll have a link to the outsourcing for creatives course by Joe gum, and the 20% off code is systems podcast all one word and again, the link will be in the show notes and notes will be in the show notes. So just in case your like systems podcasts like how do you spell it like so it’ll all be insurance, but this is something that I highly recommend you invest in especially with Jill like she has over a decade of experience like it’s not like she just invented this last week like she walks the walk she talks the talk And so check it out. I will like talk be talking about this for a very long time I’ll be I always point people towards Jill when it comes to outsourcing so that among many things, so please check it out. And while we’re ending on that note, Jill, I have several questions for you. Can you share with the audience like, what freebie you have for everyone that like kind of can help them along with outsourcing? And then how can a person connect with you?

Jill Gum
Yes, okay. I’m gonna start with the second question. So in terms of connection, I am on Instagram at Jill Gum Photography, you can find me on Facebook at the same place. I have a free Facebook group for moms who might want to learn more, I’ve got so many different things in place like that, that I would just love to connect with you on. I also have a newer YouTube channel.

Dolly DeLong
It’s really it’s like, legit you all it’s legit.

Jill Gum
Yes, I’m really enjoying that. So please feel free to connect with me in all those areas. Reach out to me, send me a message. I would love to chat with you and hear a little bit more about your business. And of course, we’d love to answer any further questions about outsourcing that you have. I love connecting with people. So please feel free to do that. And then I think we are also sharing a freebie that I have that is all about using Trello for outsourcing. It’s just a little video lesson that I have. It actually comes with a Trello board template and even if you already outsource or you use a different what are some of the other I’m so in love with Trello Asana, Asana.

Dolly DeLong
Yeah, a really good one. ClickUp is really good. Monday, I have been very tempted to completely switch everything over to like there’s this other program that several people use. Oh, man, it’s like eluding my brain right now. And somebody is screaming it at me right now. But I’ll come to my mind, but like Asana has been like is one of the ones I’m like, Ooh, maybe I shouldn’t use Asana. But this is a reminder to everyone. Like, if you find something that works for you, then continue to Yeah, like, every, like, don’t feel like you have to buy all the project management software tools, like find one that works for you and your business.

Jill Gum
Keep it simple, keep it simple. So even if you use one of those products, instead, I really gain a lot of value from seeing how people use even different programs because it can remind me of things that I’m not doing with my own program, and maybe should be so feel free to check out that freebie. Again, it’s just going to be a video that’s going to walk you through how I use Trello without sourcing. So if you heard about it, and you were interested in what Trello was, but don’t quite know yet or don’t know how to organize jobs for potential VA this would be a great, great free resource for you to check out.

Dolly DeLong
It’s seriously bothering me that I can not remember this. I’m just like looking at my phone. I’m like, What is this call? It’s um, it’s something that no, but although I have heard I’ve used notion for with Dubsado and it’s been like, really interesting to use in conjunction with Dubsado Oh my goodness. We’re not ending. No, I have to know I probably won’t figure this out. So if you guys like are listening and you’re like Dolly it’s this just mess just send me a DM to help me figure out what project management tool I am I missing out as something that a lot of people swear by it.

Dolly DeLong
Oh, man. Sorry. Well, no, I just want to say thank you so much for coming on the podcast today. Jill, I sincerely value you so much. And I just just, you’re amazing.

Jill Gum
Well, thank you. So much for having me. Dolly it truly means the world to me. I’m so excited about your podcast, I share it at every time that I can because I just feel like you are providing such a value for your listeners. So I really truly it’s an honor to be here.

Dolly DeLong
Thank you so much. And for everyone, please shoot Jill a DM and let her know like how you’re gonna start implementing outsourcing for your own creative business. And then as always, I hope you have a wonderful streamlined week and I will talk to you next week. Thanks for coming by. Thank you so much for listening to the systems and workflow magic podcast. You can find full show notes from today’s episode at dolly DeLong photography.com forward slash podcast. If you’re loving the podcast, I’d be so honored if you’d subscribe and leave a review on your favorite podcast player. Be sure to screenshot this episode, share it to your stories and tag me at Dolly DeLong education over on Instagram. Until next time, go make some strategic workflow magic.

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