Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.
Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs
Your Business Can’t Grow If You Do Everything Yourself
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Resumes don’t tell you who someone is when the pressure hits, and that’s where most hiring advice falls apart. We sit down with Renee Hastings, president and CEO of Executive Help Now, to talk about what actually makes a virtual assistant relationship work: values alignment, clear communication, and the courage to delegate before you burn out.
Renee shares her journey from being raised in an Amish community in Wisconsin with an uncompromising work ethic, to supporting C-suite leaders at Fortune 100 and Fortune 500 companies, to building a virtual assistant agency that helps busy founders get their lives back. We dig into the real reasons delegation feels terrifying, fear of losing control, perfectionism, and the worry that mistakes will reflect on you. Then we get practical: what to delegate first (email, calendar, recurring client needs), how to stop expecting your assistant to be a mind reader, and how to onboard well by sharing context, priorities, and introductions to key stakeholders.
If you’re a solopreneur who thinks you can’t afford help, we break down fractional back office support and why even 20 hours a month can create leverage. You’ll leave with a simple reset plan: breathe, do a quick time analysis, write a “never again” list, and use it to start a clear conversation about budget and support. Subscribe, share this with a friend who’s drowning in admin work, and leave a review with the one task you’re finally ready to hand off.
More About Renee: https://executivehelpnow.aflip.in/whatcanavadoforyou.html
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Why Resumes Miss The Point
SPEAKER_02Some people think that what they're gonna find is in a resume. It's not. One of the things that has helped us to be so sustainable and maintain such a great quality team of folks is the fact that we hire primarily based on values alignment. I ask people what their values are in every single interview that we have. What things are most important to you? What gets you up in the morning? What makes your eyes sparkle? Where do you live? Where do you thrive? What do you look for? Those things don't show up on a resume. Again, those are just skills. Skills are important, and we have crazy skills assessments tests for our team as they're going through the process. But what will keep them is having rewarding work that meets them where they are.
Meet Renee Hastings And Her Work
SPEAKER_01Welcome back to Plan Like a Boss. I'm your host, Tanya Lawson, and today I'm here with Renee Hastings. Renee is the president and CEO of Executive Help Now, a virtual assistant service agency of U.S.-based executive support professionals. She and her cohort of business operations managers, project managers, and podcast producers provide fractional back office support, remote video podcast production support, and business consulting services to founders, executives, content creators, and show hosts. Renee and her team give busy executives the ability to eat more meals at home, take more vacations, and increase their productivity. Because let's face it, life is too short to schedule your own meetings, book your own travel, find your own guests, produce your own show, and check your own email. Renee, welcome to the show. I'm so happy to have you. Hey, Tanya, thank you so much for having me. I'd like to start all these interviews by asking my guests to tell me their story. How did you get here? Because I think our story and how everything evolved along the way to get us to where we are now is so important and we can all learn from it.
SPEAKER_02Yes, 100%. And I'm honored to share my uh journey because, like you said, it's made us who we are today.
Growing Up With Excellence As The Norm
SPEAKER_02And mine actually started way back when I was a little girl being raised on a farm in Wisconsin in an Amish community. So for those that are in listen-only mode, I'm a black woman. And my grandfather moved his family from the South to this Amish community as a sharecropper. And so we were the only black family in this community for miles and miles around. So if you saw another black person, they were family, literally. So my grandfather instilled in us because he had such a passion for excellence, he instilled in us a very strong work ethic. We were people of our word, we worked hard, honest, dependable, reliable. All of those things mattered because he wanted everyone in that community's experience with people who looked like us to be nothing but the absolute best. So we just kind of grew up, me, my cousins, my uncles, and aunts just kind of grew up with the expectation that everything we did would be done well and would be done when we said it would be done. And that was just the expectation. There was no questioning it. It was just, that's just the way it was. So fast forward a little bit, my mom leaves the farm and we go to Madison, Wisconsin, which is where I ended up graduating from high school. But when I was before high school, there was this program called the Summer Youth Employment Program. And my mom encouraged education. She felt very strongly about getting a great education. And so she encouraged me to be a part of this program where they basically put kids in work opportunities to discover their skills. This is before they were able to have work permits. That's why it was a special program. And my first assignment, I was assigned to the Madison Urban League, where they took me to this room that was piled high and deep with books as far as you could see. And my job by the end of summer was to organize these books, categorize them, log them, label them, and make sure that people could find them once they got put away. So that's when I discovered my love for organizing and creating categories and subcategories and sub-subcategories, which would later translate very well into a great uh employable work experience later on. The following year, they placed me when I was at the Madison Urban League, I believe I was 12. Wow. Wow. And then they the next summer they placed me at Norel Temporary Services, which I'm not even sure is still a temp agency anymore. But the owner of this franchise was a black woman. And people would come in looking for work, you know, people from the community. And my job was to hand them a clipboard with their application forms on it, have them fill it out. They give it back to me. I'd key it into the computer. And Tanya, with the clickety clack of every keystroke, I'm thinking in my head, people's lives are changing. With me putting this information into the computer, the owner's gonna be able to then find them a job and they're gonna be able to take care of their families and their lives are gonna be better. And so I made this interval that one day I'm gonna own an office or I'm gonna run my own business. And that I was 13 when I'm making these intervals. Just because it just resonated with me so much. So those following years, I took all the business classes, the typing, the shorthand, the uh dictation. I'm totally dating myself, I know. But I really had a joy and a passion for everything business, everything marketing, and ended up, because of all these credits I had from all the classes I was taking, I ended up graduating from high school at 16 years old. When I graduated, Tanya, I also had a one-month-old son. So I now couldn't go to college the way I had planned because now I had a son to take care of. But because of all of these employable skills that I'd been practicing since 12, I now had an opportunity to go to work for the state of Wisconsin Department of Transportation, I believe, is where I started at the state of Wisconsin. And I worked a full-time day job during the day and a part-time night job in customer service for Wisconsin Bell, because I didn't want to be another statistic. Because in school, in health class, they said, one in ten of you girls is gonna get pregnant by the end of this school year. And I said, Oh no, not me, not me, it's not gonna be me. Yeah, sure enough, I was that girl. And then they said, if that girl gets pregnant, she's gonna end up on welfare and she's gonna be a burden on society. And I said, Oh, surely that won't be me. And that's why I went to work all day and all night. But long story short, I couldn't keep that up because I missed my son's entire first year of life. I missed his first steps, I missed his first words, I missed all of his firsts. And I said to my then husband, I said, This is supposed to be your job. You're supposed to take care of us, so I'm not gonna do this anymore. And so I ended up staying home and asked him to work. Uh Tanya, we ended up on welfare. So moving fast forward, but I continued to work, continued to grow in skills, continued to grow in knowledge, and people saw the excellence that uh that I performed with. And they just kept promoting me and advancing me and giving me opportunities to stretch. And those have served me well. So I started out as maybe a receptionist and then a clerical assistant, and then an administrative assistant, and then uh an executive assistant to a director, and then eventually the executive assistant to the C-suite, chief executive officers, chief financial officers, chief
Corporate Rise And The Seed Of Business
SPEAKER_02marketing officers of Fortune 100 and Fortune 500 companies. And with those experiences and that growth and knowledge, I became privy to information that most people would never have access to because you're the confidant that that executive has, and he can have conversations with his assistant that he can't have with other people because people are looking up to him, you know, or whatever it looks like. So I took that responsibility very seriously and I was like Fort Knox. There was no getting any information out of me because I valued that relationship so much. So after working in corporate for all those years, it took someone else to say, Renee, you know you're supposed to own your own business, right? And I said, No, I don't think so. I'm pretty comfortable here in corporate with my three weeks of paid vacation and health insurance benefits. And they're like, hmm, okay. And they, but you know, it just takes one person to plant a seed, right? They just planted the one seed. And then I started thinking, hmm, what could it really look like? And so I started taking on, I started a business, executive help now, and started telling people about it. And just I'm just working on the nights and weekends because I still got my corporate day job. And that eventually evolved into the my our client, my client telling their friends about how great their lives are now because they don't have to do everything by themselves. And they kept telling their friends and their friends, and before I knew it, I was working just as many hours in my business at on the nights and weekends as I was working throughout the week. And so it became quite challenging because I would work my day job from eight to five. I'd come home. I'm a wife now, and I'd try to have a meal with my husband and then start on my business work at like seven or eight at night, work until two or three in the morning, take a nap, get up at six to be back at work at eight again, and doing this over and over and over again for months on end. And then the quality of my work started to suffer. Yeah, that's not sustainable. It is not sustainable. Those are the exact words that my uncle used when he is a retired IBM executive. He said, That's not sustainable. Your body is gonna shut you down, whether you want to be shut down or not. So you need to figure out how to fix this. You need an assistant. And so, Tanya, that's when I hired my first assistant. And I was able then to delegate the work that I was doing in my business to her. And then we would just check in for
Burnout Sparks The First Hire
SPEAKER_02a few minutes or, you know, an hour or so each evening where I so I could check in on the status of the different things. But I didn't have nearly as much to do in the business because I had someone to delegate it to. And then the quality of my work on my day job got better, my quality of sleep got better, my relationships got better.
SPEAKER_01Everything got better when I brought on an assistant. Love that. That is such a beautiful story. And I don't think that person planted the seed. I think 13-year-old you planted the seed, and that person just gave it a little bit of fertilizer, a little bit of water.
SPEAKER_02Agreed, agreed. Because it wasn't until then that I remembered, oh yeah, I did say that a long time ago.
SPEAKER_01Yeah. And it, you know, I I can't imagine that childhood where you had the pressure of representing an entire race of people.
SPEAKER_00That that's a lot of pressure.
SPEAKER_02It really to me, Tanya, it didn't really feel like pressure though. It just when something is just an expectation, like that's what everybody does. It's just like what everybody does. You know what I mean? Like, so all my uncles, all my cousins, my aunts, we this is it was just the norm for us. So it didn't feel like pressure because I was too young, number one, to understand the the implication of my of all of our actions. It was just this is what you do, this is how you act, this is how you respond, this is how you show up. I love that, period.
SPEAKER_01I love that. I love that. And you know, and I I'm a I am a music teacher and I also teach part-time at a university. And I have a little seventh grade student. Her mom is a pediatrician, and when this little girl emails me, she writes the most professional emails. And my college students, they can't do that at all. And like you said, it's you know, I I told her I was like, that's a good email. She's like, Oh, my mom taught me that this is how you send an email. And yeah, good. Good. So now you talked about hiring that assistant was like the the step that really kind of took everything off your plate so that you could perform better at everything else. Yes. And
What To Delegate First
SPEAKER_01uh say you're a solopreneur out there and you you need someone, maybe you can't afford someone full time. What are the first tasks that you should delegate?
SPEAKER_02So I one of the first things that I delegated to my assistant was my email. So, like when I would get an email, I would check my emails from my phone during my breaks and on lunch and and that sort of thing. And anything that needed something done, I would just forward it and I would say to my assistant, please assist. Period. Thanks, exclamation point, smiley face. And so that was one of the first things I did. I was just delegate my emails and the tasks that were coming in. And then she would also manage whatever was happening with the clients that I was serving. So they had travel arrangements to make, the board meeting itself, committee reports to follow up on and make sure we're included in the deck and all the different things. So those were the first things that I delegated was my calendar, my email, and whatever the clients needed.
SPEAKER_01Love that. And so I know for a lot of solopreneurs, their business is their baby. And handing that over to someone else can be completely terrifying. And they pull back and they hold off not hiring help because they're thinking to themselves, oh,
Fear, Control, And Learning To Trust
SPEAKER_01nobody can do it as well as I can. I need to handle it all. What would you say to those people?
SPEAKER_02I would say to them, I can relate. Because I went through that exact same thing myself. And because I knew that I was tired. I knew the quality of my work was suffering, which we know is not acceptable. And so I knew something had to change. But when the idea of handing something over or letting somebody in to my space and in behind the curtain of all of my business, I my heart would start to race, like literally race. I'd start to get shaky. And I'd and I was, and I'm a praying woman. I'm a woman of faith. So I pray a lot. I pray all day. And I'm like, Lord, what is this? Why am I feeling so shaky? Why is this terrifying me so to be to at the idea of having someone else in my stuff? And I realized that the bottom line of it all was fear. Fear of loss of control, fear that, like you said, no one can do it as good as me, perfectionism, fear that they might make a mistake, you know, and it would look make me look bad or make our client look bad. All of those things. It was so that it was so heightened in my awareness that this is something that was keeping me from being able to reach that next level. And so I prayed for strength and courage to do do it in do it afraid. I just did it afraid. And and it it wasn't easy. I'm not even gonna lie and say it was easy. It was not easy, but I knew in my mind that it was a step I had to take. And if I was gonna be all that I could be, or this business is gonna be all that it can be, I had to get over this. So it took some, I had a great community of people around me, um, uh, you know, Bible study group and prayer partners and things like that. And let me tell you, I needed all the prayers. But that's what I got. I did it. And the more my assistant kept performing well and working with excellence and representing me well and representing the company well and putting out excellent work, the more my trust began to grow. And the the more she did that, the more my trust grew, the more I was able then to delegate because she'd earned the trust. Does that make sense?
SPEAKER_01That totally makes sense. That totally makes sense. And you know, you know, it's it's scary. I agree. I totally agree. I've um I've hired several VAs and some of them have been worked brilliantly, some of them have not at all. And that's gonna happen. Now, when some say someone out there listening and they're like, okay, I do need help. I need to look for someone. What are the first things someone should look for when they're looking to hire an assistant?
Hiring For Values Alignment
SPEAKER_02I love this question because some people think that what they're gonna find is in a resume. It's not. One of the things that has helped us to be so sustainable and maintain such a great quality team of uh folks is the fact that we hire primarily based on values alignment. I ask people what their values are in every single interview that we have. What are what things are most important to you? What things uh what gets you up in the morning? What makes your eyes sparkle? Where do you live? Where do you thrive? What do you look for? Those things don't show up on a resume. Again, any those are just skills. Skills are important. And we have crazy skills assessments tests for our team uh as they're going through the process. But what will keep them is having rewarding work that meets them where they are. And so if the more I know about that, the better I'm able to assign them things that match where they thrive. And that I think is most important, more important than can you write a right or correct email or can you, you know, do these other skills things? While skills are important, I'm not trying to minimize skills, but I'm saying where their values align is more important because if somebody is like money driven, money hungry, everything's about the money, they're gonna, you know, do whatever it takes to get the money, they're cutthroat kind of people. Those are not our people.
SPEAKER_01No, they're gonna be done as soon as a better money opportunity comes along.
SPEAKER_02Exactly. And and I'm not saying that those are bad things, I'm just saying those things aren't what we have to offer. That's what they can find someone somewhere else. And that's the environment that they need to be in to thrive. And so I'm not knocking it. I'm just saying that wouldn't be a good fit for us.
SPEAKER_01Does that make sense? And that makes sense because also skills can be taught. Absolutely. 100%. But but values are something that are deep-seated. So I love that that's what you first look at. And and I think that's good advice for anybody out there looking to hire. Now, when it comes to hiring someone and having someone work for you, you have to delegate things. What are some of the most common delegation mistakes that you see entrepreneurs make? And what can they do to prevent these from happening in the first place?
SPEAKER_02So, some like you said earlier, a lot of people have a problem with delegation. Um, and they
Delegation Mistakes And Better Onboarding
SPEAKER_02fear delegation like I did. And but once they finally let themselves do it, and I'm thinking of a client uh in mind right now, and that's kind of why I'm smiling, because he had a hard time with it at first as well. And we kind of coached him through what to do and how to work well with his assistant. One of the things that he would do was just give an assignment with no background, no explanation, no understanding to the person of how this matters to the other things going on in his business or in his world, but just do this one thing and then basically expect his person to be a mind reader, to know all the things that it takes to get this thing done and what's most important and what's not very important. So one of the mistakes I believe that entrepreneurs make is expecting your person to be a mind reader and not taking the time on the front end to help the person understand what they're what you're asking of them and how it adds value to the rest of the company, where it, where it fits and why it's so important that they do this particular thing. The more time you take on the front end to even cast your vision of what you want for your business to your assistant, then you set up your assistant for success to be able to help you even better because they know now this isn't just about a travel arrangement. This is about a relationship that's trying to be developed because we're trying to get here instead of, you know, staying back here. So I believe that communication is one of the delegation mistakes. Lack of communication is one of the delegation mistakes that a lot of entrepreneurs make.
SPEAKER_01Yeah, I can definitely see that. And I've I've made that mice, that mistake myself early on. Just just taking the attitude of, oh, you're the expert at this, go ahead and handle it. When and then it didn't go the way I wanted it to. And I have nobody to blame but myself. Right. We have to manage expectations, right? Yeah, and that's it, that's a tough lesson to learn, but that's Part of entrepreneurship. You you make the mistakes, you learn from, you move on and you don't make them again. And I agree. I agree. I the more time you spend up front training and working with who you've hired, it's gonna save you way more time and headaches in the future. 100%.
SPEAKER_02And I think I'm sorry, go ahead.
SPEAKER_01No, I was gonna say also just giving them permission to ask you questions because I think a lot of times they might get nervous about that.
SPEAKER_02Yes, they do. And when you give them that permission, then it's so freeing because you're saying, I'm accessible. Come to me, I'm here for you. I want you to be successful, I want you to succeed. Ask me whatever you need. I think another key thing too is to make part of your orientation, meeting other people within the business that are key stakeholders to you, people that matter to you, people that you work closely with and introducing, making that proper introduction and saying, hey, this is my new assistant. She's going to be reaching out to you on my behalf, give her whatever she needs, and then allowing that time for that person on the team to show them a little bit about what they do and that so they can get a full picture of what the business is, how it operates, what uh what the the goals are, what the metrics are, what they're shooting for, so that they can truly feel ingrained in a part of your entire back office and and be more, be able to be a greater assistant than if they just were given a task to do. Yes, yes.
SPEAKER_01Now I know maybe a lot of people out there listening right now are thinking, you know, I'm I'm a very small business. I am a solopreneur. I don't have the money to
Fractional Support And The ROI Math
SPEAKER_01hire a full-time assistant. And in a way, they they wear that solopreneur badge, like a badge of honor. Like I do it myself. I'm a one-woman person. But sometimes I feel like maybe there's a little fear behind that. Oh, I'm a I could do it all myself. And it might be just because they're nervous about hiring. They're they're nervous about spending that money. So what if someone maybe they can only, you know, afford a handful of hours a month, you know, not you know, halftime, quarter time. What would you say to them? What how could they benefit?
SPEAKER_02Yes, absolutely. So there are companies out there like Executive Help now, where you the packages start at just like 20 hours a month. So 20 hours a month, if you break it down, is five hours a week, which is like an hour a day. And some people might think, oh, well, can't do anything in an hour a day. You can do a lot in an hour a day. And just imagine if you got those hours back. You got five hours a week back in your life. Usually it translates to a lot more than that that you get back because you're now freed up. Your mind is freed up. So definitely take advantage of those companies that offer fractional back office support so that even those things that you are doing now can be delegated to somebody else. Because think of it like this, Tanya. You're the owner of a whole business. Let's say you make $2,000 an hour. And with your $2,000 an hour pay, you are trying to hunt somebody down to schedule a meeting. Is that the best way to spend your $2,000 an hour time? Absolutely not. Absolutely not. You delegate to that to someone else who isn't as expensive as you so that you can spend your $2,000 an hour time out there doing what's going to benefit the business and improve the bottom line. If it's not making you money, you should not be doing it.
SPEAKER_01Absolutely. Even $100 an hour is not worth chasing that down. Right? Right, exactly. Yeah. I just kind of say that for a fact.
SPEAKER_00No, no, no, 100%. 100%.
SPEAKER_01And so let's say you have an entrepreneur out there listening right now, and they are definitely feeling overwhelmed in their business. And they just don't know where to start when it comes to getting the support and the help they need.
SPEAKER_02Where do they begin? I think the first thing that you'd want to do is take a moment to breathe. Breathe in deep. Exhale,
The Overwhelm Reset And Next Steps
SPEAKER_02drink a tall class of ice water, and start writing a list of those things in a perfect world, what you would never do again. Those things that you would delegate, things that take away your time from actually being able to focus on the business now, fixing things, whatever needs to get fixed, or focusing on your future and where you want to go with the business. Write a list. What does it look like? How are you doing like a time analysis? How are you spending your day? Are you spending an hour checking email? Are you spending an hour responding to email? An hour networking, an hour on social media, an hour doing this, that, or the other, whatever it is, make a list. And then you reach out to a company like mine and you say, look, this is what I have going on. This is my budget. These are the things I want to have done. Can you help me? And then we have a conversation and we see what it looks like. And hopefully bring you on as one of our new clients.
SPEAKER_01I love that. Yeah, no. And I I love that you can go with that approach. Like, this is what I need done. This is what I have to spend. What can you do? And I think that's a good way to approach it. Now I always like to to to end these episodes with the same question. I want you to think
Courage, Abundance, And How To Connect
SPEAKER_01way, way back to that younger self who's starting out in business. If you could give her one piece of advice, what would it be?
SPEAKER_02If I could give one piece of advice, thinking back to my younger self, I would say, be courageous and know that you deserve abundance.
SPEAKER_01That's beautiful. That's beautiful. I like that. I I feel like I should write that down and put it in my office somewhere to look at every day. Be courageous. Know that you deserve abundance. Yeah. 100%. To the people out there listening who are like, yes, I want to do this. I want, I need some work. I want to talk to Renee. How can they find you?
SPEAKER_02Well, they can reach me on all the socials. So we're at Executive HelpNow on LinkedIn. Uh, our website is executivehelpnow.org. There's a contact form there. Um, we're on Instagram and I actually have a YouTube channel called Renee Speaks. If anyone wants to check out uh those social podcast type of activities, that is another service that we offer through another business called Livestream Editors. If someone wants to do a show and doesn't want all the work, we offer Done For You service. And that's at LivestreamEditors.com.
SPEAKER_01Awesome. We will make sure to link that in the show notes. And as you're listening out here, I want you to start thinking, what would you do with those extra five hours every week? Would you take your kids to the pool? Would you go play a game of golf? Would you maybe just sit down with a cup of coffee in a great book? And as you're thinking about that, go ahead and start making that list of tasks that you need to delegate so that you can contact Renee and get working. And until next time, keep planning like a boss.