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From HR to Entrepreneurship with Tiffany Deans · Better Together

• Shawn Sundsvold: Hi everyone, welcome back to Better Together, the podcast sharing real stories from founders and business leaders navigating the true journey of entrepreneurship. We talk about the risks, the pivots, the pressure, and the growth that comes with building something of your own. I'm your host, Sean Sunsvold, joined by my partner in business and in life, Kelly Sunsvold. Today we're joined by Tiffany Deans. She is an HR strategist specializing in organizational development, employee relations, compliance, and culture building. She is the founder of Grounding Work LLC and after more than 20 years in human resources, including leadership experience in the federal sector, Tiffany understood how organizations succeed from the inside out. But instead of staying in a stable established career, she stepped into entrepreneurship and became what she calls an accidental CEO. What makes her story especially powerful is she wrapped up her very first year in business just as COVID broke the world. In this episode, Tiffany shares what that year taught her about resilience, client alignment, and building a business on strong, people-centered foundations. If you're leading through uncertainty or growing into a role you never expected, this conversation will definitely resonate. Tiffany, thank you so much for being here. I'm really excited to have you on the show today. Tiffany Deans: Thank you, Sean. I am so thrilled to be here with both you and Kelly. Yeah, it was. Shawn Sundsvold: Yeah, our first conversation, it was so fun. And I think this will be a really good conversation today. let's start, take us back to the beginning. What was that early career path and how did you find your way into HR? Tiffany Deans: Yeah. Yeah, so early, early on, like 20 years ago, I had an internship in an HR office. again, it was nothing that I grew up and said, hey, I wanna be in HR. It was an internship, it was paid. I said, cool, like, I something to do this summer. Kelly Sundsvold: Yeah. Tiffany Deans: I ended up really liking it. I really enjoyed it. I always knew I wanted to help people in whatever career path that I chose and HR was a thing and it stuck and I really enjoyed it. And so from then on, I found roles in different organizations that were HR and I was super gung-ho about it, loved it. did a bulk of my ⁓ HR career in the federal space. worked the federal government and I worked at a couple of different agencies. So I was able to really learn a lot about HR and grow within ⁓ federal government, which was awesome. Shawn Sundsvold: Yeah. Kelly Sundsvold: That's really good. That's really good. It's interesting, like... You know, HR is one of those things that, those departments that, you know, employees love and hate, but is very, very needed. Yeah, yeah. ⁓ So you've worked across both the private sector and in the federal space too. Like we just talked about, like your location to DC. ⁓ How did those experiences kind of shape the way that you ⁓ think organizations and leadership? Tiffany Deans: ⁓ yeah. ⁓ yeah. ⁓ yeah. Yeah. Mm-hmm. Yeah. Yes. Yeah, so I, like I said, I worked in the federal government and then before then I was in a couple of different other spaces. So I worked for some consulting companies and things like that. So while the work was similar because it's HR and people work, it was very different in how these organizations approached it. In the federal government, there is a lot more regulations and in addition to the HR regs, right? So there's just federal government regulations and things you have to kind of do. And a little more boxy versus ⁓ in private company where, you know, there's a little bit more flexibility in the way that you do things. And so it taught a lot in what I like and what I don't like ⁓ in my approach HR. And, you know, of approach to people. it also taught me a lot of structure too and what things really need to have more structure around it versus what things don't. So I was able to take a little bit from both sides and kind of make it into my own today. ⁓ Shawn Sundsvold: Awesome. And that subject and that conversation of making it your own, right? I think it leads in really well, you know, to the next discussion here of at what point did you start thinking about building something on your own, right? You've been in HR for 20 plus years and I know we've talked, but I'll let you tell a story, but it's like, you know, that shift happened for you and it happened fairly quickly. Tiffany Deans: Yeah. Yeah, yeah, it did. And, you know, I wish that I had some magical aha moment to say, hey, this was it. And I, I know I'm going to, you know, start my own business, but it was not that at all. Like you mentioned, ⁓ CEO. I you know, working. I had just had my oldest daughter. So she was ⁓ one my at the time was really sick. And so I had come to this crossroads in my career and at work where I just didn't have the time to be there for my family and my time wasn't my own. And so I just, talked to my husband about it and I just kind of left my job. I didn't have anywhere to go. I didn't have any plans, but I knew I needed to be there for my family. So that was the push or the shift that got me out of where I was. And then from there, I said, okay, well, like, what am I going to do next? And I applied for a few jobs. I didn't hear anything back. And so I took that as a sign that I need to kind of do some, you know, something on my own. And so you know, kind of set some things up, but not really very seriously. ⁓ it wasn't until... ⁓ think probably about three months after I left my job, I had someone reach out and say, hey, Tiffany, you do HR, right? And I said, yeah, I do. And so she's like, well, I need someone to help me with a couple of projects. And I was like, okay, great. I just kind of fell into it. So was the work, but then also learning or trying to learn how to do the work of a CEO. And then I kept getting more and more business. ⁓ picked up really fast within those, I'll say three to four months, I was getting like different clients from word of mouth, which was great. And I was just kind of taking everything on. I'm like, sure, I'll do this, I'll do that. So I was really busy once I pressed like the go button on the business. I just, again, I kind of fell into it. Yeah. Kelly Sundsvold: It's interesting, we've talked to a lot of CEOs on and founders on the show ⁓ we've just, I mean, we've been in our careers for, you know, 20 plus years. ⁓ it's interesting how many entrepreneurs say the same thing that ⁓ weren't out to start a company. They really became kind of, they saw a hole or they had a need like you and your kid ⁓ ⁓ daughter and your dad and being closer to family like that. Tiffany Deans: Yeah. Yeah. Kelly Sundsvold: Accidental CEO is, we're starting to see more of a theme being woven and it's just that creativity of like, need to support my family, ⁓ but I also need have that flexibility. What does accidental CEO mean to you specifically? Tiffany Deans: Yeah. means to me that there was no, there a plan or anything ⁓ premeditated it. was just, it was something ⁓ that happened ⁓ and went the flow. And so ⁓ in operating in space, you know, like I said, I've been in HR for a long time, but I feel like, that same intern again in certain instances because I feel like I am learning how to navigate this space from a completely different angle. It's very different working for someone and working in established organizations. And then all of a sudden now you are building your own organization while still working and, you know, supporting clients. So it's a very Kelly Sundsvold: you Tiffany Deans: Yeah, just kind of a go with the flow. Go with the flow and like sink or swim type of type of thing. So it's a little mix of all of that. Yeah, that's what I would describe it. Shawn Sundsvold: Yeah, yeah, for sure. it's a process, right, to ⁓ all of that out. But I'm curious, what was it that surprised you the most about shifting from, am HR person, ⁓ and has been your career, to now I am this entrepreneur, CEO? What was the biggest surprise in making that shift for you? Tiffany Deans: Mm-hmm. Yeah. Mm-hmm. You know, think Sean, I think the biggest surprise for me now that I think about it is how much I was capable of. And so I didn't, know, working for someone else. It's like, you know, here's what you're supposed to do. Here's your job description. Very and white. Very okay. Very easy. And then coming into the space where you are, you are now, you are You are. Kelly Sundsvold: Mm-hmm. Tiffany Deans: the boss, you are the marketer, you are sales. you know, coming into it at first, was a little scary because I didn't know what I was doing and still don't always know everything. But then to know that I am capable of more than just HR, it's like, hey, I have these other skills that I either was able to kind of brush off, you know, and, and, or skills that I didn't even know existed. And so I'm just kind of like, wow, I can... Shawn Sundsvold: Mm-hmm. Yeah. Tiffany Deans: I can do, you know, a lot of things. A lot of things. So, yeah. Yeah. Kelly Sundsvold: Yeah, you can. Yeah. Shawn Sundsvold: You Kelly Sundsvold: No, that's awesome. mean, it's almost a little bit of self-empowerment. like you mentioned, like going into a business that, you know, had the four walls, had all these systems in place, usually by probably by the time they're bringing in a full-time HR person, they've been around for a while, you know, and they have a clear, they have a clear path for what they want you to do, ⁓ your job role is. ⁓ And you're right. When you step out on your own, you don't have that. You are the person that's having to invent all Tiffany Deans: Yes, yes. Right. Yes. Kelly Sundsvold: that and so it's like not only are you inventing the product, you're having to sell the product, market the product, know, insert service where product is, but it can definitely be very stressful and you find out really quickly how quickly you can grow in certain areas and also some, I think some deficits that we have, you know, we've talked on this show about like how accounting was our first hire and I'm really glad we did that and you know, we are, Tiffany Deans: Yeah. Absolutely. Shawn Sundsvold: Mm-hmm. Kelly Sundsvold: We are a lot of first entrepreneurs, business, where lot of times we're their first marketing team. And I can imagine that ⁓ as fractional HR person, you're you're you might be the first HR person that this person has ever had. So you're taking all that experience ⁓ and being to ⁓ really pour these small businesses who don't have that ⁓ So talk to about what that first Tiffany Deans: Yeah. Kelly Sundsvold: year was like because I'm sure there was a lot of growing pains that you had but what was it really like strategically emotionally kind of digging a little bit on there? Tiffany Deans: Yeah, so if I'm being totally honest, I would say the first year was so exciting. it was exciting in a sense because it was new. It was something I had never, a space I had never been in before. And I mentioned before, I had so many, had ⁓ a of different clients and I was like, ⁓ my gosh. This is great. Like I was, I was busy. I was doing different things, meeting new people. And so I really, really enjoyed being able to do different things and not having like the same day every day. On the flip side of that, it was a lot to juggle. ⁓ because I was new, I said, you know, like I mentioned, I said yes to everyone and yes to everything. Okay, sure. Yes, I can do that. Sure, no problem. Like I said yes to everything. And so ⁓ it was exciting, I found myself very overwhelmed. And like, okay, like how am I supposed to juggle all of this? Cause you know, it was just me. ⁓ And I probably my first year I probably had, I want to say at a time, maybe like six clients. And so, ⁓ and clients, being there, Shawn Sundsvold: Yeah. Kelly Sundsvold: Yes. Shawn Sundsvold: Mm-hmm. Tiffany Deans: in-house HR. So I'm doing that for six clients. ⁓ again, I just jumped into this. So it ⁓ exciting because it was new and fresh, it was, man, it was, it was a lot. It was a lot. ⁓ Shawn Sundsvold: Yeah, yeah. So I'm thinking here is, you know, it's going through, right? You started your company in 2019. You get those first six clients. It's going really well. You've got all that excitement. And right as you're wrapping up year one and so excited, we all see March 15th happen of 2020. Tiffany Deans: Yeah. Shawn Sundsvold: Right? so I'm curious, like, especially like wrapping up year one, right at the height of COVID, right? Like, you know, April, I think was your kind of starting year. So March is that right at that wrap up for you. How did that impact you as a founder and somebody who's building a business? Like ⁓ us through what that like that, when that moment, what that moment looked like for you and how you pivoted and how you decided to keep going. Tiffany Deans: Yeah. Mm-hmm. Yeah, so that was a very interesting time. So for a few reasons, I remember specifically in March and I remember doing a training for an organization. I think a few days after that is when everything just kind of shut down. And so I didn't had one client that cut ties. They were like, hey, like we, you know, we're to have to let you go. And it was just it was so much uncertainty. And so. ⁓ everything shifted to being fully remote at the time, right? I had been working remote, but of course, if clients ⁓ me to be on site, I would be there as well. So everything shifted. No quite knew what to do and how to navigate this new space, and especially with all of their people. So the clients that I did have, I was busy ⁓ because were trying to figure out What do we do with our people? What are our new policies? How do we work now? We're not coming to the office or people are sick. Like it was just so much happening. So I was still very busy, but it was nice to be, was nice to not only just be home, but that everyone, were all in it together. And then on a personal note, I was actually, I was pregnant at the time. So ⁓ think in March I was six months pregnant. So ⁓ that point, Kelly Sundsvold: Mm-hmm. Shawn Sundsvold: Yeah. Wow. Tiffany Deans: It was very nice not to have to out and travel and be in so many different spaces. So I really welcomed that hard stop that we all had to do during that time. Yeah. Yeah. Yeah. Shawn Sundsvold: Yeah. Mm-hmm. Kelly Sundsvold: Yeah, that was quite the time for sure. And I can only imagine as a mom also, like just being six months pregnant and just be like, okay, I run shut down. Okay, cool. Me and the couch and Netflix, we're ⁓ have some time, bring my laptop, do what the work I need to do and just shift and realign, readjust for sure. So kind of thinking about like these hard lessons that you've had to learn through the first year, ⁓ Tiffany Deans: Yeah. Yeah. Yeah. Yeah. Yeah. Kelly Sundsvold: year it's the hardest. that I bet a lot of our listeners are relating to is the saying yes to everything because you just you're still figuring it out and said to a lot of things that I'm looking back on and I'm like I can't believe we said yes to that ⁓ but we and we did it and it was fine we learned through it. ⁓ But what some of the hardest lessons that you had to learn you know ⁓ just over the that you've been in business? ⁓ Tiffany Deans: Yeah. Yeah. Yeah, I think some of the hardest lessons, like it's not saying yes or rather saying no. Admittedly, that's been a lesson I've had to learn even up until maybe like last year, if I'm being like totally honest. And not just saying no to just, you know, any type of. Kelly Sundsvold: Yeah. Yeah. Tiffany Deans: know, client, but just also like the people that you work with. And it's like really knowing, it's knowing your capacity. ⁓ much as I get excited about things and I'm like, yeah, this sounds great. I to what I could really handle and how much of it I could handle. I also had learn, was, so hard. I'm at a good place now, but it took me like, up until last year to really learn my niche was. ⁓ in saying yes to everything and everyone, I was saying yes to all kind of industries and organizations and ⁓ I just really didn't fit. we, meaning me and the ⁓ I was working with, we were just not a good fit. And I had to really accept and own that and say, okay, Tiffany, these aren't Shawn Sundsvold: Mm. Tiffany Deans: your people respectfully right like they're not your people and that's okay like you can't be to ⁓ and i that like the the really like the big pill i had to swallow and just be like okay all right i'm not going to be everybody's cup of tea they're not going to be mine and it's okay ⁓ so just just accepting that piece that's the heart Shawn Sundsvold: Yeah. Yeah. Yeah, I think that... Every business owner goes through it, right? Unless they just come into it knowing exactly the niche they're gonna fill and do all that. It's like go through that process of like, okay, we take everything and then we realize, okay, that's not our cup of tea, right? And ⁓ know, you've got to figure out ⁓ you said, you know, who are the clients I align with the most and how do I set these boundaries for myself, you around protecting not just your energy and your time, right? But your business, right? Tiffany Deans: Yeah. Yeah. Yeah. Shawn Sundsvold: So I'm curious, like talk a little bit more about learning those lessons and you know as you were dropping clients or you know and going okay they're not mine they're not my my people right for one reason or another we just don't align but talk to me about that what that process looked like for you and and how you sort of worked through it because I think every every business owner struggles with it. Tiffany Deans: Yeah. Yeah. So one, will say this. Every client that I knew we weren't in alignment with, I knew it upfront. ⁓ I could tell I could feel it upfront, but I always said, OK, you know what? Well, maybe this one's going to be different. ⁓ every time I did not go with my gut, it ended up not being ⁓ a good fit. Shawn Sundsvold: Mm. Tiffany Deans: that I do want to say that at first. So, but then once, know, I signed anyway, we're working together. And I've clients who have said to me, ⁓ like, hey, is not gonna work. So it's ⁓ both ways. if I'm being like totally honest. And so I think had to, I've, ⁓ I've learned to work through it as far as like I did my best with the client and did my best work. But again, I think it's just that acceptance piece of it, which sometimes it's hard. Like if a client says, hey, this is gonna work, it's like someone breaking up with you before you break up with them. And you're kinda like, wish I did first, because you already knew, but. But then there's a piece where it's like you have relief, but then you're like, know, man, is this, is this a reflection on me? Is this a reflection on like the work that I did? But just kind of, you know, taking that time to really just say, okay, know, Tiffany, you did your best. And it's It just didn't, it just didn't work. ⁓ And that's So. I think for me, a lot of it is just kind of working through the, through the ⁓ taking everything just personally, which really hard as a business owner, like not to do, right? Because this is you, this is a reflection of you, this is your baby. ⁓ And sure you all get it too, you know? So yeah, so I think just kind of ⁓ you working through that piece kind of. Shawn Sundsvold: Mm-hmm. Yeah. Kelly Sundsvold: Yeah. Yeah. Tiffany Deans: And I learned how to work through it quicker and let it make me stagnant or kind of stop me from ⁓ the work. But it's a lot of self work that I've had to do. ⁓ Kelly Sundsvold: It's, it really is man so much of what you said I I feel like we should go get coffee and talk about this on a deeper level because we'll go meet in DC. ⁓ I am sure there's 35 coffee shops that would be quiet that we should go talk. man, I feel that to the core. know, when those clients, especially ones that you really like and you think things are going really well or maybe they are and they just like we had a client step off last year. Amazing. Loved her to pieces. She was, you know, Tiffany Deans: I mean, let's go. Let's go, Kelly. Yes. There are zillions. Yes. Yeah. Yeah. Kelly Sundsvold: I said she was the best boss. She was a business coach. loved working with her and man when she wanted to shift ⁓ marketing, she was getting, she's I have tons of leads. ⁓ What I need is sales help. ⁓ And really just was not closing those sales. And so she had to shift her money from marketing to sales. And I was just like, I'm so sad. Can we still talk? And she's like, we better. ⁓ And ⁓ we've maintained a friendship, but ⁓ Tiffany Deans: Okay. Yeah. Yeah. Yeah, yeah. Kelly Sundsvold: you know, honestly, she needed to do that because it was best for her business. And that alignment piece, my gosh, man, I feel that. But ⁓ are right on, and I think so many of our listeners ⁓ our audience that hears that, and as an entrepreneur of like, especially like service-based businesses, it's hard. ⁓ It really, really is. It's a mindset shift to not take that personal ⁓ and to really keep Tiffany Deans: right. Yeah. Yeah. Kelly Sundsvold: keep moving forward. So what lessons, you know, we talked a little bit about that mindset that you have to build up and I'm sure that's a constant thing that always having to ⁓ kind ⁓ realign, What ⁓ are some lessons that you're still actively applying today that you've learned in your business? Tiffany Deans: Yeah, think ⁓ of the biggest lessons I'm learning ⁓ and I think Sean mentioned it, but just about boundaries. Not saying yes or no to certain clients, but the clients that I have said yes to, okay, what are my boundaries? ⁓ And I being in a service-based industry and business and, I'm an HR, so I wanna help the people and are always so many people things happening. mean, so right? But I have to make sure, I have to be my best self in order to help my clients. And so I have put a lot of things on the back burner for myself, like for Tiffany and then for my business. to, you know, at a detriment to make sure that my clients have everything that they need. And so then I've done this and I got a gold star from them, I found myself in a situation where it's like, ⁓ well, I didn't even do this for myself or I didn't, you know, I'm not even thinking about myself in the same way or my business in the same way that I'm thinking about for my clients. And so working through boundaries and saying, like, I'm not gonna respond to emails after this time or I'm not going, you know, these are the days that work and it's so hard or even, you know, taking time ⁓ that is, ⁓ my gosh, like I've gotten so much better at it, but just learning how to know, unplug and take time off because I found, I've, I was on a vacation, I did something with my kids, I think probably last year, and I can't remember where we went right now, but I was doing both and taking my laptop with me, and here we're on vacation and doing things, but then I'm like, hold on, and mommy's sending an email, mommy's doing this, and trip right there, I was like, okay, this has to stop, I can't do both, ⁓ one, I'm not being a good mom to kids because I'm... physically there, but I'm ⁓ mind, everything else, my energy is not. And you know, so I don't want that for my kids. I don't want them to have to grow up and remember, yeah, I remember on all those ⁓ vacations, you were always working like, you know, I don't want that to be the memory. So really having just to set those boundaries so that my professional and personal life are balanced somewhat. Shawn Sundsvold: I build a business to live my life the way I want to it. And then how do I Tiffany Deans: Yes. Yes. Shawn Sundsvold: interspersing all these pieces in to create the life I want. You had a 20 career in before you jumped to your own business, right? Tiffany Deans: Absolutely. Yeah. So it definitely, taught me all things HR. Like I am very confident what I do and what I offer. ⁓ can do HR in my sleep. can, know, someone brings something to me, I can tell you exactly what's gonna happen. You know, have seen all kinds of all kinds of scenarios, all kinds of things. And so... You know, it's prepared me in a sense that that nothing, nothing really catches me off guard or surprises me I just ⁓ haven't seen it all. I'm not going to say, ⁓ I've seen it all. I've done it all. I have not. But know how to ⁓ manage ⁓ I get overwhelmed. ⁓ what it didn't teach me. I have people skills, but having people skills from the perspective of a business owner is different. ⁓ And I say that in a sense because I didn't really know how to talk business because I worked in HR. so then I found myself in spaces and in rooms where Shawn Sundsvold: Yeah. Mm-hmm. Tiffany Deans: I didn't know how to speak like a CEO. And struggled with that. ⁓ still do at times, but I just, didn't know the lingo. didn't know what certain meant, how to connect the dots. And so, yeah, ⁓ I felt I was starting from ground zero. I had no idea what... Shawn Sundsvold: Yeah. ⁓ Tiffany Deans: anything meant like in the business world. I just knew HR. So, yeah. Shawn Sundsvold: Yeah. Kelly Sundsvold: Yeah, yes, yeah, for sure. So getting close to the end here, but I wanted to give you an opportunity to share with us what you do ⁓ grounding work. Tiffany Deans: Yeah, so I have, say I have the pleasure of being able to partner organizations and come in and help them make the workplace just a better place. You know, spend so much time at work ⁓ and I've been a firm believer that you shouldn't be unhappy at or be in a space where, you know, the, you know, where you work isn't like the best placed. ⁓ able to come in and partner with ⁓ CEOs and leadership to help not only like the culture, you know, of the workspace. ⁓ so with culture, that's, you know, employee engage, ⁓ employee engagement. You just making sure people helping, helping to really be able to understand their people, ⁓ listen to their so that they know what's going on with them and then that way they know how to really focus on the business. And then also I help with policy. I'm really big on kinda helping set things up. And so that's why I work with, specifically now, startups and I call them startovers. So if an organization is in transition, then I can come in and help because we're starting from the ground up. So hence like grounding work. Shawn Sundsvold: Mm-hmm. Yeah. Tiffany Deans: And so we're setting the foundation. So helping you put your HR systems in place. I said, policy, compliance, onboarding, offboarding, ⁓ what that looks like, ⁓ and really doing it in a very humanizing way. yeah, yeah. ⁓ Shawn Sundsvold: That's awesome, that's awesome. And we talked about a little bit at beginning that HR is that scary word. Right? Like we've all been in corporate America, you know, and done it and, know, we hear HR and we're just like, you know, so I love that you're doing, I love that you're doing it in a way to connect, right? And to not make it this scary thing, right? That so many people think it can be, right? So for people who want to learn more about you and what you do and how you run your business and how you help them, how can they get in touch with you? Tiffany Deans: I know. I I know. Kelly Sundsvold: you Tiffany Deans: Yeah. Yeah. Yeah. Yeah. Yeah, yeah, absolutely. Well, I am definitely, I love LinkedIn. So you'll find me there. So my, ⁓ my name is linkedin.com slash IN slash TS Deans. I'm also ⁓ my website, You can find me there ⁓ and I'm pretty everywhere, but LinkedIn, that's, that's my jam. I love it. So. Kelly Sundsvold: Nice, nice. ⁓ Tiffany Deans: I'm there. Yeah. Shawn Sundsvold: Well everyone who's listening, know, definitely go look up Tiffany. ⁓ Today's been a fantastic conversation and I thank you so much for your time and your insight and you know, just being so transparent with us about what those early years looks like. So thank you very much. Tiffany Deans: it has. Thank you. Yeah, thank you, Sean, thank you, Kelly. This has been great. I look forward to the next time. Shawn Sundsvold: Awesome, love to have you on again at some point. Thank you. Tiffany Deans: Yeah, thank you.