Better Hiring Strategies for Your Small Business with Dana Kaye

[00:00:00] Emily Thompson: Welcome to Being Boss, a podcast for creatives, business owners and entrepreneurs who want to take control of their work and live life on their own terms. I'm your host, Emily Thompson. In this episode, I'm joined again by my friend Dana Kaye, to chat about hiring, knowing when for what role, and how to figure out who to best fill it.

[00:00:21] You can find all the tools, books, and links we reference on the show notes at www.beingboss.club. And if you like this episode, be sure to subscribe to this show and share us with a friend. All right, bosses. It's time to add another podcast to your queue. Let me introduce you to The Shine Online, hosted by Natasha, brought to you by the HubSpot Podcast Network, the audio destination for business professionals.

[00:00:46] Natasha recently did an episode, I know so many of you will want to make a mad dash for as it's become a common topic than Being Boss community. It's called Why You're Burned Out on Social Media and a Solution. And if that's not your jam, Natasha's interviews and conversations about entrepreneurship, mental health and the art of shining online will certainly have something to fit your fancy Learn more and listen to The Shine Online wherever you get your podcasts.

[00:01:14] Dana Kaye is a lifelong entrepreneur who believes in the power of storytelling and authentic personal branding. In 2009, she founded Kaye Publicity Inc. A literary public relations agency, known for her innovative ideas and knowledge of current trends she coaches our clients on how to identify and establish their unique personal brands.

[00:01:35] In 2016, Dana launched Midwest Mystery Conference, formerly Murder and Mayhem in Chicago, a one day conference dedicated to crime fiction with mystery author Lori Rader-Day. She is also the author of two books, Your Book, Your Brand, The Step-by-Step Guide to Launching Your Book and Boosting Your Sales and The Personal Brand Workbook, and she serves on the advisory board of Propel PR.

[00:02:00] Dana, welcome back to Being Boss. So glad to see you again.

[00:02:03] Dana Kaye: Long time no see.

[00:02:05] Emily Thompson: Right. If you are unfamiliar, we had Dana on a couple of episodes ago. I actually just had this pulled up. You are in episode 323. This one I think as of recording is, let's see, 336, so you can go back 13 episodes ago. We had Dana on to have the conversation that we're here to have today, because that one, it didn't take like a wild turn or anything, but I feel like there was so much more set up.

[00:02:31] That needed to happen. So we dove into Dana's building of her company, how she has, uh, or how she has grown her team in the way that she has, how she's transitioned from being a doer into a manager, all of those things. And that episode, which really sets us up for this episode, which is really a, around knowing who to hire and for what and how to create a company culture that people want to stay and work in.

[00:02:59] So thanks number one for that conversation and number two for coming back to have this one.

[00:03:05] Dana Kaye: I will talk about team any time, it's such a challenge for so many of us. I think, you know, in our weekly C-Suite calls, I'm pretty sure that every week there's at least one team conversation happening. And so if I can share my experiences and what I've learned and help other bosses avoid any pitfalls, um, I'm always game to do it.

[00:03:27] Emily Thompson: Perfect. Perfect. Well, I, you're right. We talk about this all the time. Like team stuff is always a part of the conversation and you know, it is within the context of the C-Suite, but it also is with like every business owner that I know who has started building any kind of team. And so this is, this is, you know, your first VA who you just contract for a couple hours a month to, you know, start handing off some, some tasks to, it could be, you know, you're hiring a social media manager, you're hiring your first sort of consultant.

[00:03:57] Like it starts in those places and it moves into your first part-time employee, your first full-time employee. You're like 12 person, team, whatever it may be. Once you take that first step, growing and managing your team and you know, creating the environment in which they can work and get their stuff done and all of these things, it becomes a major part of what we as literal bosses in this situation, um, and what it is that we do.

[00:04:27] So I do what I really want to illustrate, I think with today's episode, I feel like we dove into this a lot in that previous episode, but here it's really about the intentionality that goes into choosing the right people that makes that part easier and better and more effective, and all of those things.

[00:04:49] So I'm excited, dive in.

[00:04:51] Dana Kaye: And you're in a season of hiring too, so I think you'll have lots to share.

[00:04:55] Emily Thompson: Oh my God, so many people. Indeed. So I hired someone this week. I'm doing more interviews over the next two weeks. Um, indeed I am, let's see, let's see where this goes. Because there's also an interesting sort of dichotomy happening here between the two of us.

[00:05:12] Where, and I, this has been how I've traditionally worked, but hiring professionals, which is what you do. And you talked about that a lot in the last episode, and that's something that I have done obviously also in the past. But as we have grown, the Almanac store in particular, I'm hiring a lot of college kids.

[00:05:30] Dana Kaye: Mm-hmm. .

[00:05:30] Emily Thompson: And so it's a whole different. It is a whole different ball game. Let's start with knowing when to hire. I would love from, if you can even remember your first hire, like what that was like and how you knew when it was time, and how that has evolved into where you are today. How do you now know when it is time to hire?

[00:05:55] Dana Kaye: So I did make my first hire really early. I made my first hire within the first year of business.

[00:06:00] Emily Thompson: Mm-hmm.

[00:06:01] Dana Kaye: Don't know if that was good, bad, right time or not, but I, at that point, I felt like I was taking on too much and I couldn't do it all myself. That was the point. And so I hired an assistant, which in hindsight, I think that a lot of us will hire, we think that that's the first hire we need to make, right?

[00:06:25] We think of all the low level stuff, like the managing the calendar, the inputting receipts, like all the data entry stuff. We think, okay, that's the first place we need to hire. And maybe it is. In hindsight, I actually don't think that that was the first thing I needed to hire. I actually think I needed to get more systems in place and I actually needed to get software and get other, you know, computer stuff versus a person.

[00:06:52] Um, but I think my first hire was an assistant. She was part-time. She was not good. Um, I was not good. Nothing about it was good. Um, and then from there I had some assistants and some interns. But I think my first like big full-time hire was in, in, I was about eight years, no, yeah. Seven or eight years into business.

[00:07:18] When I had my first full-time hire and then I hired a publicist, I hired another person to deliver the work. That might have been, if I had been further along in systematizing how I deliver work, that actually would've been the best hire because I can scale a lot better and a lot more quickly if I have other people who can actually deliver the thing.

[00:07:46] So our company delivers publicity services. And if I have an assistant assisting me, that's great, but I'm still the one delivering the services. If I have someone else delivering the services. That removes me from a few of our clients, it removes me from several of the processes. And so that's actually what I find to be the best way to scale is once you have your systems in place, once you have a method, um, our mutual friend Tara McMullin calls it the secret sauce the way you do business.

[00:08:18] Once you have that down, hiring other people and teaching other people to do that is a really great way to scale. So now, I would say for the past couple of years, that's where the focus has been, is hiring people to deliver the thing. So we have several publicists, we have two marketers. We have now, we hired a dedicated events person, um, and those, those are all people who are dealing with the, they're all client facing.

[00:08:47] They're the ones delivering the product, delivering the thing, being the face of the campaign so I don't have to be the face of the campaign. And then now that we're at that point, now we're starting to fill out the, let's call it the back office stuff. So we hired a research assistant. She doesn't deal with clients.

[00:09:06] She's helping the publicist and helping the marketers by researching new media outlets, finding new influencers, reviewing, uh, inbound media requests. So she's supporting them. And we also have an executive assistant who is the Jill of all trades and kind of helps everybody with everything and is highly organized.

[00:09:27] So we first started hiring people to deliver on the service, and then now we're starting to fill out with some of those back office things because we don't necessarily want. It adds a level of complication with clients where if I have too many people serving the clients, like that's not good. Right? The clients want to have a small team of people.

[00:09:51] They don't wanna be dealing with 10 different people. Um, and so right now we're trying to fill in some of the back office where we can support the client facing folks so they can increase their capacity.

[00:10:05] Emily Thompson: Love it. Okay. I literally, totally eight notes really important things that I wanna hit on because there's so many little nuggets in here that have to be, that have to be like shown a light on.

[00:10:16] Um, first, I love that you said your first hire probably should have been software. Yes, because I think that so many people are in exactly this place. So if you are in a place in your business where you feel like it's time to make your first hire, pause for a second and see if there aren't pieces of technology that you can use to do things faster, better, smarter, or totally automated so that you can have back more time before you go and hire someone else.

[00:10:48] I think that one is key. Maybe you need bookkeeping software. Maybe you need social media stuff. Maybe you need to check out some AI copywriting. Maybe you need to look at Zapier and sort of creating automations between your things so they talk to each other. I don't even know what it is. I mean, that is key.

[00:11:04] Um, and I know that you have become like a automation. I don't like, well, I don't even know what word is.

[00:11:13] Dana Kaye: Geek, nerd?

[00:11:13] Emily Thompson: Yes, sure. Yes, yes. Um, you are doing a lot of that. How much of your company now would you say is technology and automations?

[00:11:24] Dana Kaye: You know, it's hard to have a

[00:11:26] Emily Thompson: Yeah, that's a weird question. Yeah.

[00:11:27] Dana Kaye: Yeah. But I, so I will say, so this kind of goes back to like knowing when you need to hire, knowing what you need to hire.

[00:11:35] Emily Thompson: Yeah.

[00:11:35] Dana Kaye: So one of my favorite activities is when people are getting squeezed. When my team members or myself are feeling squeezed. We track our time, we have Toggl, um, there's other apps, but we look at our time and I look at where people are spending their time. So I literally will take, you know, Julia's time, I'll sort by duration and look at where she's spending her time and I start making notes. And I look at how much of this can be automated, how much of this does she in particular have to do? Or a publicist, let's say we don't wanna talk about people, but roles. How much does a publicist have to do?

[00:12:15] How much can, like, could this be done by an assistant, could be done by a more entry level person? And so I start making those lists. And I think if you think it can't be automated, try thinking harder and being creative like this is, I think what I love about automations is that you can be so creative and there's no one way to automate something.

[00:12:36] Like I'll change the trigger or I'll change the flow to accommodate different things. Um, and so like we just, you know, we added a new piece of software that we've been trying out recently and, it's great. And then my next step is, okay, how can it integrate? What else can I do? How can I connect it to Asana?

[00:12:55] How can I connect it to our calendars? Whatever it might be. And so I think that the first step is to look at what you're actually doing and what you actually wanna offload. And then just ask yourself, can this be a piece of software? So for example, our client onboarding process, we have a lot of steps to onboard a client, um, just high level.

[00:13:16] We have, I have to get them set up in QuickBooks. I have to task out their, create their project in Asana. I have to set up their stuff in Toggl. I have to set up their folder and Dropbox. I have to add all their assets to Dropbox. All of that's automated. All of that's automated.

[00:13:34] Emily Thompson: Yeah it is. Of course.

[00:13:35] Dana Kaye: Of course it's cause again, you think like, well, how can, how can they just be automated while we created a form in Airtable. So every new client gets a welcome email and. They will fill out a form, they fill out a form and it triggers these 10 different things that happen. We tried to get more granular, so again, it doesn't always work.

[00:13:58] Like I tried to do it something where if they accept the proposal, it automatically generates, the email doesn't work cuz I have to handpick who I wanna assign to the project. All of those things. So you might try some things that, to try to automate some things that don't work and you just double back or you think of a different way to do it.

[00:14:16] So we can't have an automated email, an automated welcome email, but I do have a template, a Gmail template that I use so at least I'm not reinventing the wheel every time. Um, so yeah, there's a lot of software that cuts down on our. It isn't just cut down on like manpower, womanpower, we have all female team.

[00:14:36] Um, but it does, it also cuts down on any friction or any balls getting dropped. Cuz I think that's really the piece cuz the only reason I'm so on top of things is because of software. I'm not naturally on top of things in any way. Um, I'm laughing cuz I almost didn't make this interview because I forgot that our son had a half day of school cause it wasn't on the calendar.

[00:14:56] Um, fortunately we have an alternate plan, but again it's like the software is what keeps the balls from getting dropped. It's what keeps us organized. And so I think that anytime you can opt for software, we should, cuz it's reduces human, there's no human error. Right.

[00:15:14] Emily Thompson: For sure. One of the things, so I know one of the blocks a lot of people have, and I've come up against this with bosses from the very beginning to people who have been in business years is paying for software thing or like you will get nickel and dime to death.

[00:15:28] You'll have subscriptions, you know, all day long, every day, every month when another one's coming out. And the way I always, the, the way I reframe this is that as an employee, if you set things up well and right then the, you know, $400 a month that you're spending on all of your subscriptions all the way up to, I, like, I feel like at Being Boss, ours is probably like 2000 a month.

[00:15:52] Like if I really think at a lot of the stuff that we are using for, you know, everything from bookkeeping to social media, like all the way down, probably about 2000 bucks a month on, on subscriptions. That's an employee. And that is, and that's like a cheap employee, really when you think about it. And.

[00:16:12] Dana Kaye: It's way less to have a, it's way less to have software than it is to have an employee. And software is a lot easier to manage as we'll discuss.

[00:16:20] Emily Thompson: Indeed, indeed.

[00:16:21] Dana Kaye: Than an employee.

[00:16:22] Emily Thompson: Right? So easier to, easier, easier to train if you, if you change setup for training or training for setup. And there is very little management just sort of checking in and making sure things are doing what they're supposed to do and keeping up with updates.

[00:16:36] So that's a reframe that I wanna make it. And I love that you say that because that is incredibly important. And even as you add people to your team, if these software things are in place, it makes onboarding and it can make it easier and more difficult depending on, on, you know, who it is that you're, you're bringing into a role and how much they're gonna be involved with it.

[00:16:53] Um, but it makes it easier for you to run those pieces of the company that don't need human hands doing it. It can be automated. So first hire can be software. I also love that you mentioned that your first hire was not a good one because that is everybody. I feel like a lot of people go into that first hire going, you know, I'm not gonna get it right.

[00:17:13] You're right, you're likely not. It's likely not going to be a great scenario. I remember the very first time I hired a VA, it was useless. Like I, I didn't know how to delegate. I think she may have been a little new to it too. And there was like, it just immediately did not work. I think I paid for one month and was like, okay, this is not working.

[00:17:35] Thank you. Bye. And I got nothing out of it. Like that is going to be, I think the experience of everyone, unless you are just lucky or have it together or something. Um, in making that first hire your second, third, fourth, and beyond get better.

[00:17:51] Dana Kaye: Was your first VA, was she a contractor? Yes. And that's another lesson learned.

[00:17:57] Emily Thompson: Yeah.

[00:17:57] Dana Kaye: So I think that with my first VA. So I, so I, let's back up. So I, my office, I had a brick and like, I had an office. This was in 2009. And so like you're talking about all the systems and tools, like a lot of these systems didn't exist back then. You remember like your tanning salon days and

[00:18:18] Emily Thompson: Automations what?

[00:18:19] Dana Kaye: Automations

[00:18:20] Emily Thompson: were no such thing.

[00:18:21] Dana Kaye: No. And so we did what we, we we made do with what we had. But I think in hindsight, like hiring a contractor is way lower risk. And when we hired our first VA, like a vir, when we did go virtual and we had a virtual assistant, the first one didn't work out. I hired through a service and I came back to the service and I said, I don't think you gave me a seasoned person.

[00:18:45] I need like a really seasoned person. And so they're like, okay, we got you. And she was, had been a VA for 10 years, I think, at that, or been an assistant for 10 years at that point. So I learned a lot from her as, you know, as she was my first virtual assistant about her systems and her tools. And I was, and she was easy to train on our systems and our techniques.

[00:19:10] So your new hire most likely is you're going to, you're gonna be going for cheap, right? It's most likely gonna be like an entry level person. You're both inexperienced. You've both never done this before and no wonder it's not gonna be super successful. So starting with a contractor and perhaps a subject matter expert can really help with that because you are new to managing, but they won't be new to working for someone and they won't be new to the, the service they're providing.

[00:19:37] Emily Thompson: Yeah, for sure. Okay, next note I made. Um, oh. You started on this a little bit, talking about the difference between hiring some back office help and hiring for you, another publicist, like someone who's gonna be delivering to clients. One of the things that I always talk about when someone is thinking about really making any hire from their first to their 10th and beyond, um, is it's easy to think I need someone.

[00:20:02] I remember having, um, having someone literally come into my office very early days of Indie, just file papers, which like, totally, like, that's the furthest back office right thing to get someone to come do. But you know, it was just, it was something that I needed that I had it done, it was fine. But when it comes to actually making it hire, for real, for real, one of the things that I always recommend you think about is getting that person cl as close as you can to making money.

[00:20:32] In your business because this is an expense that you are taking on, and that doesn't always mean that you're hiring someone to deliver to the client. Sometimes it is, how can, like what is the biggest piece they can take off of your plate so that you are closer to making money or whatever it may be. But that little, that little question of who or what is going to help me make money as opposed to just like clean my desk is a really great sort of, uh, reframe for thinking about who it is you're hiring first.

[00:21:03] Dana Kaye: 100%. Because I think ultimately a clean desk is nice to have, but you can deal with having papers around, right? Yes. Like, it's not gonna make you, it's not gonna earn you more money. It's not going to like improve your business substantially. And so I think that getting them closest to the money is a really good frame.

[00:21:25] And I also think, if you're thinking about it in a way, like, okay, I'll hire a VA because then I have more time to sell. Well, what happens when you're so good at selling? Like, are you gonna be able to deliver on everything? Mm-hmm, like that's the next thing to think through. Uh, I had coffee with an entrepreneur friend earlier today and she's like, I think I'm ready to like go on podcasts and really start promoting my business and all these things.

[00:21:49] And I said, but you just said that you're booked through February. Like you just told me that you have no time in your calendar, so why do you wanna do this? And so thinking about like, if you're gonna free up time for yourself, if you're gonna make that space to take on more, are you also going to be able to deliver?

[00:22:08] And maybe so maybe it is a two-prong approach. Hiring someone to deliver and help free up so you can sell more. You know, I've, the past few years I've been making hires in two, I've been hiring two people at a time. Um, it's great for economy of training. It's great for them to have comradery and it's a lot easier just to fan through a bunch of resumes all at once.

[00:22:31] Um, but I think looking at if you're going to make this capacity for yourself, what are you gonna do with it?

[00:22:37] Emily Thompson: Yeah, exactly. And do you, do you have the capacity to follow through with what happens when that's all in place? When was the last time you said It's almost too easy when talking about a piece of tech?

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[00:23:39] Um, one more thing that I want to, that I want to address around your initial comments is you didn't really touch on this because you're Dana, and I, I, I know that you feel this, but like, you, you did not allude to it in that you went into it thinking, you know, maybe it should have been a publicist, you know, from the get-go.

[00:24:01] A lot of times I know that bosses will hire someone to file their papers as opposed to being the publicist sitting right next to them, helping them deliver the thing because of this mindset that no one will do it like me.

[00:24:16] Dana Kaye: Hmm.

[00:24:16] Emily Thompson: And I just wanna say it out loud right here, right now. When I hear a boss say that, whenever I hear anyone say that, that is a red flag, baby boss mindset.

[00:24:27] Right then and there of like, of you are really like, you gotta get over that. Absolutely. Get over that. Because you're right, to some extent you're wrong in that sometimes people can do it better than you. And three, that's just part of the process.

[00:24:43] Dana Kaye: Mm-hmm.

[00:24:44] Emily Thompson: of getting them in, getting them trained, teaching them all of the things I like to think about, um, my first, I think my first real hire and definitely my like long-term hire is Corey.

[00:24:54] Hi Corey, who still edits this podcast, hired Corey 10 years ago. 10 years ago. And I hired him on to start just doing some coding work for me. So I was a web designer and developer. I, he was my publicist, right? Who to come sit next to me and do the thing. He wasn't doing the big projects that I was doing, but he was doing all of the maintenance stuff.

[00:25:17] Very green still in college. Um, knew plenty of things. Also was teaching him a lot of things along the way. Um, and has, is now way better at all of the things than I am. We were just looking at reviewing some website stuff for Almanac and he was saying words to me I'd never heard before.

[00:25:39] Dana Kaye: Love that.

[00:25:40] Emily Thompson: Right? And so getting someone in to do the thing with you, um, to do it and allow them to become better than you, starts with you getting them in to do the things that only you can do in this moment. And everything can be replicated by someone else.

[00:26:02] Dana Kaye: There's nothing that delights me more than me learning from my team.

[00:26:06] Emily Thompson: Yes.

[00:26:07] Dana Kaye: If my team teaches me something or if I come in and say, this is how we do it. And they were like, well actually Dana, you're wrong and this is why. I love that because it means we're getting better. It means we're getting better.

[00:26:19] Emily Thompson: Yeah. And we're getting better. Like they're getting better than you. Or like the company is getting better than you.

[00:26:27] All. Too often I will hear bosses talk about how, you know, if, if they're not hiring up, they're keeping the hires down, right? They're hiring that like, you know, cheap contractor. They're, you know, hiring someone who they're gonna have to teach how to do the thing there builds this frustration that they're the only one in the company who knows how to do the thing, or they're still the ones that are, you know, keeping the ball rolling or whatever it may be.

[00:26:53] And that's what happens when you are afraid to let someone come in and do the thing that you think you can only do yourself, or that you're gonna have to make a real investment to do it. You stay in this place where, where you are the one that you know, has all the knowledge and you are just continually teaching.

[00:27:11] Whenever you can hire up, this thing happens where they are coming in and they're showing you, they're presenting you with a plan, right? They're teaching you all the new things and, and, and then the company is moving faster. Maybe not even faster, but just beyond where you can take it in this moment.

[00:27:28] 100%.

[00:27:29] It's a great feeling.

[00:27:30] Dana Kaye: I think it's also thinking about the type of business that you want. So like if you're in the, like Paul Jarvis company of one camp, right? Yes. Like you can just do the, the people on Upwork or the VA or the random, you know, bookkeeper or whatever it is, and you can just be the person.

[00:27:47] But this conversation is about those of us who want to make a greater impact with our business and scale it in a bigger way. And so it's really just thinking about the type of business that you want. Like I would like my business to exist beyond me.

[00:28:02] Emily Thompson: Yes.

[00:28:03] Dana Kaye: Like I think it took a long time. I mean, it's called Kaye Publicity, it's my last name, but we're now, I think, whatever, four, almost 14 years later.

[00:28:14] Finally at a point where we have name recognition beyond me. Like there's people who know my company name, who have never met me, and that's a really, and I couldn't have done that without hiring really great, talented people.

[00:28:27] Emily Thompson: Yeah. Oh, I also love that that it's example is, you know, it is a very personal brand that you have achieved this growth beyond yourself.

[00:28:36] Okay. I wanna go back to this, this question and get really practical with it, of like really when to hire, because I've heard a couple of mindsets around this in the past. I have my own. But I want to know from you when it comes to filling a specific role in your business, like you know that a hire is like right then and there, at what point do you recognize that and actually start the process of hiring someone?

[00:29:03] Dana Kaye: So this is a shift. I'll speak to it. When we were, when I was just me or just one other person?

[00:29:10] Emily Thompson: Mm-hmm.

[00:29:11] Dana Kaye: I knew it when I would start, there's a few signs when I start turning down clients or feeling like we didn't have bandwidth.

[00:29:19] Emily Thompson: Mm-hmm.

[00:29:19] Dana Kaye: when I started feeling like we were really squeezed or overworking when I felt like we were struggling to deliver on our promises, those were all signs that we needed help. Or I shouldn't say that. Those were all signs that something needed to change. So I have options, right? I could take less clients and make less money, could take less clients and charge more.

[00:29:44] I could take on more clients, charge the same, and bring in other people to deliver. Or I could do what I did is bring in more people to deliver, charge more and take on more clients and do it all. And so I think that when I started seeing, again, our time, our weekly times as going up, like the amount of time we were billing each week, when I saw that things were starting to slip or things were just feeling a lot of friction, and when I felt like we had to turn down clients, not because they weren't good quality clients, but because we didn't have capacity, that's when I was like, okay, now we need to hire.

[00:30:27] Now I try to hire more proactively. So right now, we spoke about this, the last episode. I hired a publicity director before I needed one, and it's very boss and a little nerve-wracking. Um, I think since last episode we, we've gotten a lot more stable and it's, we're we're seeing the light where she's like operating more at capacity.

[00:30:49] But that was something where, I'm, I'm trying now to hire, because we're at a certain level. We have a certain amount of team, we have a certain amount of revenue. I'm trying to anticipate and hire ahead of demand. And so look, so I, same thing. I look at where there's friction, I look at where I don't have capacity.

[00:31:07] My biggest capacity block right now, or currently still right now is being able to field new client inquiries. We get an average, we get anywhere from three to five new inquiries a day. Probably one to two of them are quality and I'd say one a week. About one a week is how is I'll be taking on proposals and wanting to like give a full proposal.

[00:31:40] When I give a proposal, I read the whole book. So right now she, our new publicity director is fielding all the new people. But guess what? Our clients write more books. So I still have three books to read. I've read three books in November. It is November 10th, no, November 9th . I have read three books and given three proposals.

[00:32:01] Um, and that's just for our current clients who wanna re-up. So there's still that f, there's still that, um, squeeze a little bit. And so I think that I try to now hire more proactively to give more capacity. But I think in the beginning again, it's more about cash flow and revenue planning and all those things that you just have to look at where everyone's getting squeezed and looking at what you can do to free up their bandwidth.

[00:32:27] Emily Thompson: Yeah. Mm. One of the things that come up for me in that is that when you're paying attention to what's happening in your business, you sort of develop your own signals. Right of when it is that you need to hire. And so even you mentioned earlier looking at like when your entire team is, um, is spending more time on things and then things within yourself as well in your own workload, really sort of finding those for yourself.

[00:32:53] And I love that you, you transitioned from being a little more responsive or reactive to being now more proactive because I think that's one of the things that you were afforded as you grow your company. I think, you know, when you're small, you just, you get to a place and you put it off long enough that , you know, you finally make the decision, you do it and you get a little better at it as you, as you go.

[00:33:14] I've also heard. I feel like maybe Kathleen is an advocate of this. I may be putting words in her mouth. Sorry, Kathleen. Um, but I think she's a really big proponent of like, of really waiting to hire. She's, she is not one to take on risks and she'll be the first to tell you that, um, does not have a very high tolerance for risk.

[00:33:33] She's, so, she's going to wait until things hurt a little bit more before she finally makes the move to hire. And even to this day, I think to some extent. Me, on the other hand, I'm on the exact opposite of the, of the spectrum, if I wanna be staffed up really good as early as possible, um, which really just means I end up getting staffed when I need it.

[00:33:54] Because that's the thing that I also really wanna point out here is it takes so long to hire someone that if you start when you need it, it's too late.

[00:34:07] Dana Kaye: 100%. They don't operate at full capacity for six months.

[00:34:11] Emily Thompson: Yeah.

[00:34:13] Dana Kaye: It's the first 90 days, which is like their trial period. They're probably your employees operating at maybe a 30% capacity.

[00:34:22] So like they're working full-time, but you have part-time work, right?

[00:34:28] Emily Thompson: Yeah.

[00:34:29] Dana Kaye: And so it is a big investment. It does require a lot of patience. So if you already need them, then you need to get them on board real quick. And if you rush that process and rush the training process, it's not going to, it's not going to end well.

[00:34:41] Emily Thompson: Yeah.

[00:34:41] Dana Kaye: At least I don't think so.

[00:34:43] Emily Thompson: No.

[00:34:43] Dana Kaye: But I, I think it also changes for everyone and their, again, their risk tolerance and their, and their capabilities. So when I was younger, I'm old now, so when I was younger, I could say, all right, I'm going to like burn the midnight oil for a couple months, build up my cash reserves, and then hire.

[00:35:04] I can't do that anymore. Like, I can't work at night. I can read at night, can't work at night. I only work 20 hours a week. I have a kiddo with lots of varying needs. Like I just can't do that. So I also think it's everyone's tolerance and everyone's ability. So like in some ways, yeah, cash flow wise, it would be so lovely if I could just be squeezed for a few months and build up some reserves feel better and then hire when I really, really need to.

[00:35:32] But that just doesn't work with my lifestyle. So I think it's also, I would rather take home less pay or be a little squeezed for a few months and keep my lifestyle as is in terms of my time. So that's the other piece of look, knowing Kathleen may have a lower tolerance for risk and a higher tolerance for work, whereas I can, risk does not bother me in the slightest, but I will get aggravated if I'm having to work late every night or if I'm trying to take meetings while also at a swim meet or whatever it may be.

[00:36:04] And so everyone kinda knows their different personalities and their different levels of tolerance.

[00:36:09] Emily Thompson: Yeah. Oh, the second one is definitely me too. Just don't, uh, don't affect my lifestyle, get so angry. Um, but yes, so six months for someone to be effective, but also the hiring process is at least two months as well.

[00:36:23] So if you look at, that's like an eight month lead for bringing really any, and this is from like, unless you are hiring a contractor with a process, and even then that's like, that can be questionable sometimes. Um, if you are hiring someone to come in and do the thing that you have built for them to do, you're looking at eight months for them to be in place actually doing it.

[00:36:46] And at least effectively no additional adjectives. Um, because the hiring process is about two months. You're creating your job description, you're putting it out there, you're taking in, um, you're taking in applications, you're scheduling interviews. They're gonna wanna put in a two week notice likely to the job that they currently have, or, you know, can't they have a wedding that weekend?

[00:37:06] Uh, the weddings in every interview, they're like, I have a wedding next weekend. I can always. Um, and so you, that's like a two month process there and then six months to really get them in and get them effective. Um, so think about that whenever you are thinking of when it is time for you to hire, eight month lead time.

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[00:38:16] You talked about this a little. But I wanna talk about for what you hire. So you talked about like sort of front of house, we have a legit front of house here, um, or a back office. What you do, what someone else does, what no one is doing.

[00:38:34] How do you decide what you are hiring your next person for?

[00:38:41] Dana Kaye: I think it goes back to the looking at what everyone is doing.

[00:38:45] Emily Thompson: Mm-hmm.

[00:38:45] Dana Kaye: And so every year, sometimes every six months, but usually just every year we have everyone make a list of everything they do on a regular basis. And we will say like, do you wanna do more of it?

[00:39:00] Less of it, stop doing it. Anything you wanna start doing? All those things. So we take a look at that and so if there's things where people are like, I would like to stop doing this, I'll look for patterns. Um, there's also, I think we mentioned this in the last interview, I use Clockwork by Mike Michalowicz and Clockwork

[00:39:24] basically advocates for everyone having a primary role, every role. Having a primary job function calls it the one for your pocket, the one for your back pocket, as well as a company's Queen B role. What is the thing that your company must do or it will suffer if your company can do only one thing? And don't just, for those of you listening, don't answer it.

[00:39:44] Actually take the steps in the book. We redo our Queen B roll every, probably every two years with the whole group. We all do it as a team. And so for us, our Queen B role is securing media coverage. I can stop doing sales. Because if we're securing media coverage, clients will find us. They'll say, how did that author get on the Today Show?

[00:40:07] How did that author get on NPR? And they'll come find us. So securing media coverage is our Queen B role. So that is the first thing I hire for. If that is suffering or our Queen B role is suffering, that's the first thing I'll hire for. If the Queen B role is stable, I'll look at everyone else's primary roles and look at how those are suffering.

[00:40:28] So that's how I prioritize the hiring. And also if any of our team members are not in their zones of genius, if any of our team members are doing things that they're not really good at. Right? So in the beginning we had, um, the role was marketing and events. The marketing person did all the events. It made sense.

[00:40:50] There's lots of cross promotion, cross things there. However, our two marketing people, Events wasn't their strong suit, they could do it, but it's very detail oriented. Lots of little things, lots of follow through. It wasn't in their zones of genius. So we hired an events person. We hired a dedicated events person who all these little details and checklists and all these things is in her zone of genius.

[00:41:13] And so that's kind of how I down, I look at what's the Queen B role? Is that supported? The second is what's everyone's primary role? Are they all doing that to the best of their capability or do they need support or do we need additional help? And then the final step is, is everyone is role. It's role alignment.

[00:41:32] Is everyone in their zones of genius doing work that they find valuable, doing work that they enjoy? And if not, can I take the two or three things that people aren't enjoying and is there any common thread that could create a unified role.

[00:41:47] Emily Thompson: Yeah, this, you did it. That's, that's pretty much what we do as well.

[00:41:53] And I will say, if you are a solopreneur and you want to know what this looks like, this looks like literally sitting down and writing out everything that you do. So I like to go through, you know, the past month of to-dos, like my task list, what are all the things that I did? I did marketing, I wrote blog posts, I, you know, X, Y, Z, whatever those things are.

[00:42:12] And then I always go through and, you know, I will highlight in one color everything that I love doing and that, you know, supports that Queen Bee roll and what it is that you know, I'm doing, I can do best what my core genius is. All of those things. And then in another, um, color, I will highlight like what I would love to never do again.

[00:42:31] And then I take those what I would love to never do again, and anything that's in the middle, and see if I can't create a job out of it. Like is is the thing that I hate doing all of the marketing stuff? Well then I probably need a marketer. Is it all you know, related to copywriting? Then maybe I just need a copywriter, or whatever it may be.

[00:42:48] You can do that literally just for yourself as well, and then scale it as Dana explained for everyone on your entire team to figure out what role needs to be filled next in your business. This is also really important to do, um, as opposed to just sort of trusting your gut as to what you kind of feel an itch for in this moment.

[00:43:08] Or maybe because you know, your friend hired an event planner for this thing may, that may not be a great a social media manager. How about that one? That's always the hot one. But if that's not what really what your business needs in this moment, then that like, you know, gut call you're making is not going to serve you and your long-term growth goals.

[00:43:29] So love that.

[00:43:30] Dana Kaye: Well, and it goes back to being a little more creative too. So like this research assistant role that we hired for earlier this year, that's a new role. And it came out of the team members talking about what creates friction and the friction was coming out of when the campaigns weren't going well.

[00:43:52] Meaning they would pitch their contacts, pitch their lists if they didn't get the responses that they wanted, going back to the well to find new contacts or find new people or find other outlets. That was the friction. Additionally, we try, we're creative folks, so we don't like to just go to the same people all the time.

[00:44:14] Every new client, we try to think of something, a new angle, a new hook, something we could do differently. That also requires finding those people in research. So again, the research piece came out of this need of. Multiple people saying, I find it hard. I find it difficult when the campaign isn't going well and I have to go find podcasts.

[00:44:34] I have to go find, track down someone's contact information when my, the, you know, editor of the book section of the New York Times leaves. They announce the new person, but we don't have their email and we have to find it. Um, that slows people down. I also had our marketing people were fielding inbound requests from influencers.

[00:44:56] You know, everyone's a social media influencer now, so every, you know, Jane, Jane and John and Jim want a free book. And so getting those inbound requests, finding, do they get engagement, do they have a following? Is it a real following or is it bots? You know, all of those things takes time. So we didn't have this role before, but I saw these common threads of like, oh, we need someone who can like be an online detective basically.

[00:45:21] Right? Find email addresses, see if people are legit, find new podcasts that make sense. And so that's how this role sprung out of, so I think it's not just saying, I need a social media manager, finding out what do you actually want them to do? Like what functions do you need them to do? And then you can create a role around that.

[00:45:41] It could be maybe you actually just need a content creator, not a marketer. Maybe you know how to market and you're fine to schedule hashtag optimize, whatever, but you don't wanna be in Canva making stuff, or you don't wanna be writing captions. So thinking actually about what you don't wanna do and then create the role around that versus saying, I just need, I just need an assistant. I just need this, um, and get a little creative.

[00:46:08] Emily Thompson: Yeah. Yes. All of it. So if anyone needs help with this, here comes a plug I like to use. Um, um, wow. What is, there's a section in CEO Day Kit called Your Dream Job.

[00:46:20] Dana Kaye: Yep.

[00:46:21] Emily Thompson: Is that what it's called? ?

[00:46:22] Dana Kaye: Ideal day. Ideal day.

[00:46:23] Emily Thompson: No. That, that's one. But there's also your dream job.

[00:46:26] Oh my God, everybody. I'm literally gonna have to go look this up. I'm obviously an awful bargainer. I don't even know how to talk about my own thing. Um, there is a section in CEO Day Kit that is called for everybody to see if I got it right or not. Crafting your dream job. That's it. I use this step in CEO Day Kit.

[00:46:47] I literally do have so many of these printed out, I just can't remember what it's called, um, where I will sit down, I will do this exercise, I'll also get my members of my team to do this as well. And it fills a lot of those questions of, um, of what, what are you great at? What do you love? What do you feel most competent doing?

[00:47:04] What would you like to never do again? So it sort of has the structure for asking those questions and getting those answers and then writing out all those roles. So if anyone would like a nice worksheet. Um, for that CEO Day Kit beingboss.club/ceo is where you can get that. And I still use that every single time I am thinking about making, especially a new like, sort of higher tier how a higher tier, hire, how about that? Because I also just do a lot of like lower tier hires these days too. Um, okay. Next question for you. And this might have to wrap up with this question. So funny. We'll have to do, we have to do like a follow up follow up of this to get into this culture piece.,

[00:47:50] Dana Kaye: we just need like, like mini, mini series

[00:47:54] Emily Thompson: Dana and Emily sort of spinoff show

[00:47:59] about hiring. Cuz I do wanna talk to you too, eventually about company culture because that's so important. But we've talked about when to hire, we've talked about what to hire for. I wanna talk for a moment about how to figure out who was the right fit. And not just for a role, but also for your business.

[00:48:19] So you figured out who it is or who you need. Um, you've been doing interviews, maybe you have a couple really great candidates. What are some of the things that you look for to get the right person in the job?

[00:48:31] Dana Kaye: I think we have to talk about culture at that point, right? Yes. So yes. You know, you have to figure out what are.

[00:48:38] We do the, another plug for CEO Day Kit, knowing your values.

[00:48:42] Emily Thompson: Oh, yes.

[00:48:43] Dana Kaye: So we have, I have personal values, but I have company values, um, creativity, consistency, and community. Three Cs. Easy to remember, easier to remember. And so that's really the first piece is knowing what your company values. Knowing what your culture is so that the people can come in and embody that or fit in well.

[00:49:06] Um, I've stopped hiring for hard skills. I really believe that a lot of these hard skills can be taught. Don't know how to use Canva. I can teach you that. Don't know how to use Buffer or Meta business suite, whatever. Like I can teach you all that. I'm less concerned with that. Soft skills are harder to teach and I don't know that curiosity is possible to teach.

[00:49:31] Emily Thompson: Mm mm-hmm.

[00:49:33] Dana Kaye: And so the first thing I look for is, are they curious? Do they like learning? Are they like interested in learning new things? Are they curious? If they're not, it's gonna be really incredibly hard to train them or teach them, and because they'll never look for the answer themselves. They'll never think like, oh, I wonder if there's another way to do this, or, I wonder why we do it this way.

[00:49:56] They'll never wonder. And so if they're not curious, I can, I have a few questions that I ask that you can kind of gauge, but I also gauge it in the kinds of questions they ask me at the end of the interview. If they ask, depending on if they ask me really good, interested questions that don't have to do with the job at all.

[00:50:16] Just like, how'd you get into this industry? What are you finding to be like, challenges in the industry? How has your business changed? The curiosity piece is always something they need. If they're not curious, if they don't ask questions, they're done. I, I don't, at the end of the interview, I just know that that's not a good fit.

[00:50:32] And then the second piece is how do they embody our company values? So are they active in the community? Right? Do they, if they're in publishing, like are they going to bookstores? Are they going to author signings? Are they members of organizations? Um, creativity. I'll always ask about like a camp, something they've done that they're really proud of, or a way they've thought outside the box that they, you know, that was really effective.

[00:50:59] Um, and then consistency. A lot has to do with their resume. I'll look at do they keep jobs? Do they bounce around a lot? Um, do they, so it's not just like, Were they working? Just like, are they consistently working? Did they work there for a year? All of those things. And so that's the company values piece.

[00:51:18] And then some of it is gut feeling and practice. You might not get it right, the first few hires, but it, once you do have a team. The other nice thing is there's a panel of interviewers. Um, so you have money people interviewing them and we can talk about them. So this last round, I was the second interviewer.

[00:51:38] I wasn't the primary interviewer because there they weren't my direct reports. So Haley, it was her direct reports. So she interviewed them and I just came in for the final three and me, her and our publicity manager discussed those last three, um, for each, for each job. So I think we tend to focus, and I think this is going back to questions about diversity and inclusion and all of these things, right?

[00:52:02] We used to be like, okay, do they have industry experience? Do they have. Um, you know, do they have, do they go to a four year college? Did they have, what's their gpa? I actually don't care anymore. I really don't care. I care they have to write a cover letter so I can see that they can write. That's a, a really part of, that's also possible, but more challenging to train on.

[00:52:25] And I have little tests that to see if they follow instructions goes back to the consistency piece. So this last round, um, the instructions in LinkedIn, we posted on LinkedIn and the instructions were send a cover letter and resume to this email address with the last book you, your, the last great book you read as the subject.

[00:52:47] So anyone who just hit that apply on LinkedIn button, not a quality candidate cuz they can't follow instructions. So incorporating some of these things into the actual application process. So if you value creativity, asking them a question as part of the application process that would express their creativity if you value, um, what are your company values?

[00:53:10] Emily Thompson: So at Almanac we have experience, wonder and collaboration.

[00:53:16] Dana Kaye: So even in the process like of collaboration, like is there a way in the application process that they can demonstrate this, demonstrate wonder what's a thing that you've always been curious about and have you taken steps to find out something that will just filter, that'll filter some of these things.

[00:53:37] If they're put off by these questions, then yeah, if they're put off by these questions and they're not the right fit for you. So I try to get as much filtering done in that process while also having a broad and inclusive, um, application process. Because again, The issues of getting diverse folks into your organization is that if you're just going to people, you know, going to avenues that you're familiar with, you're gonna just hire more people like you.

[00:54:05] So if you go as broadly as possible, you have the chance to get different types of people and diverse thinkers into your organization. But hopefully they have similar values with the comp, they align with the company's values.

[00:54:18] Emily Thompson: Yeah, absolutely. You mentioned that you can teach the skills, which is right.

[00:54:25] Um, but it's the personality. So that gut feeling you get whenever you talk to people, whenever you like, are engaging with them and also making sure that they reflect those company values back to you because they are gonna be responsible for upholding them within within your organization. And then also just, I wanna reiterate this idea of you're still gonna get it wrong sometimes too.

[00:54:44] Dana Kaye: Oh, 100%. , 100%. They're people, you're getting their best version. Like people can just be really great actors.

[00:54:51] Emily Thompson: Yeah.

[00:54:52] Dana Kaye: People can be really, um, yeah, they could just be really great at performing, but that's why you ask these questions that kind of get at the root of it.

[00:55:01] Emily Thompson: Mm-hmm.

[00:55:01] Dana Kaye: Like again, how can they demonstrate curiosity in a way that can't be faked? And that if you're curious about stuff, it's going to make your job so much easier. Whereas they might lie about their ability to code. Right. They might say like, oh, I can code, and you find Mm, no, you can, you know, drag and drop on Squarespace. That's not coding , but they, but you can teach that, right?

[00:55:25] Emily Thompson: Yeah.

[00:55:26] Dana Kaye: And so I think. It's also a little bit, um, well, we can get woo here. So there's this, this piece about the, there's this piece about like looking for certain, asking certain questions, gathering all that data, but I also pay a lot of attention to my intuition. So things like my body language. If I find myself leaning forward towards the computer, we're a virtual company.

[00:55:49] If I find myself leaning towards the computer, that's a good sign. If I find myself backing away, that's a sign that it's a no-go. Um, I do draw tarot cards sometimes throughout, throughout the interview. Um, I'll just throw some cards and look at them and reflect on them later. Sometimes I'll draw a card after to just get a sense of what I really feel about them, but that's the other thing I started doing was that I used to squeeze these interviews in between things.

[00:56:15] And I really try to have like a one day of interviews with 15 minute breaks in between so I can like process what just happened and process how I feel about it because. Yeah. Otherwise you just get back in your day and you don't really like know how you feel. So I also think just paying attention to your body language.

[00:56:31] If you find yourself crossing your arms, leaning away, like your body's like, get out of here. You can take that as a sign. That's probably not a good fit.

[00:56:39] Emily Thompson: Yeah. Oh, I love it. Dana, this has been such a treat. I've loved a little peek into this process for you. How it is that you decide when to and what you're gonna be like, what the role is going to be, and even a little bit into who it is that.

[00:56:54] That is going to fill that role. I would love to come, have you come back to talk, talk about company culture.

[00:57:01] Dana Kaye: I feel like we can just have like hiring, like every Friday we just drop an episode about hiring,

[00:57:08] Emily Thompson: hiring Friday,

[00:57:09] Dana Kaye: hiring happy hour,

[00:57:10] Emily Thompson: right? I love it. I love it. I, I think there's definitely some room to have several conversations about this because this, this really is, you know, taking it to the next level of being boss and literally moving into that boss role and is one that a lot of newbie struggle with.

[00:57:25] But I also know people, I do just wanna say that I know people who have been 10, 15 years in business, who have had teams, who have had employees, um, still struggle with the process of really figuring out what the next role should be. Like what is really going to be the best, um, best new role for their business.

[00:57:43] Still like getting the right person in all of those things. This is something that really is. Once you start hiring, it is a part of what you do until you move out of the role of being boss in the company that you're building. Um, so I appreciate you coming and sharing all of this with us.

[00:58:01] Dana Kaye: Thank you. It's been fun. Always a pleasure to chat.

[00:58:04] Emily Thompson: Perfect. Then why don't you tell everyone where it is? They can find you around the internets.

[00:58:10] Dana Kaye: Um, my company is k publicity, k a y e publicity.com. And if you're an author looking to increase your sales and grow your readership, you can visit your breakout book.com.

[00:58:23] Emily Thompson: And last but not what's, making you feel most boss?

[00:58:27] Dana Kaye: You know, I today felt really boss. Um, I all, I had to do the only two things on my to-do list were to read and review our Q3 PNLs and budgets and balance sheets and adjust our forecast. So the two things. The creative artsy side of reading, and then also the CEO or CFO role of reviewing our worksheets. And I did did it at a really cute cafe.

[00:58:57] Emily Thompson: Perfect. Oh, then you did it right? Indeed. Totally right. Perfect. Thanks Dana. This has been a treat.

[00:59:03] Dana Kaye: Thank you.

[00:59:07] Emily Thompson: All right, boss, because you're here, I know you want to be a better creative business owner, which means I've got something for you. Each week, the team at Being boss is scouring the news, the best entrepreneurial publications and updates and releases of the apps and tools that run our businesses, and is curating it all into a weekly email that delivers the must know tips and tactics in the realms of mindset, money, and productivity.

[00:59:30] This email is called Brewed. We brew it up for you each week to give you the insight you need to make decisions and move forward in your creative business. Check it out now and sign up for yourself at beingboss.club/brewed. That's beingboss.club/brewed now, until next time, do the work. Be boss.