EPISODE 590: Moving from Corporate Sales to Solopreneurship with Professional Organizer Lisa Malone

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[EDITOR’S NOTE: This episode featured an interview with Lisa Malone of You Have Arrived! She’s also featured in “The Entrepreneurs’ Toolkit for Success, at the Hey Taxi Live Launch Summit in February 2023. Register here.”

Find Lisa on LinkedIn.

LISA’S TIP:  “Find the one little thing that really lights your fire every day, so you can go to your meetings with that fire. People can tell from your voice if you’re in it or not in it. The one thing that you can do yourself is be in it. Get that energy out there, find fun. Find fun in every day because every day there’s challenges all over the place, and if you just can find that little spark, things will go well for you.”


Fred Diamond: I’m excited to talk to Lisa Malone. Lisa, you and I have been friends for, God, it’s close to 20 years. You were at Microsoft for a long time, and Microsoft was a client of mine before I created the Institute for Excellence in Sales. You and I worked very closely. I worked with a lot of partners in the not-for-profit space, and you were managing customers in the not-for-profit space. We did a lot of work. Obviously as friends, we’ve been following each other’s career, and I’m very excited right now. Again, Lisa Malone, you’re a professional organizer and you’re the creator of You Have Arrived!. Tell us a little bit about what You Have Arrived! is, and we’re going to have an interesting conversation today.

Again, a large part of the Institute for Excellence in Sales and the Sales Game Changers Podcast is our focus on corporate women in sales. You were definitely there and you left the corporate world to follow some of your passion and to bring some real value to some of the women that you serve. Tell us a little bit about You Have Arrived!, and I know that there’s something coming up you want to get across as well.

Lisa Malone: I have created You Have Arrived! with a stylist. As you mentioned, I’m a professional organizer. You Have Arrived! is an online course that is consumed on demand, that helps women with a closet full of clothes and nothing to wear transform their wardrobe and their closet so that it becomes this gorgeous boutique space that they can shop their own clothes and really through the course, do the work to figure out what do they want to convey to the world. Moving from corporate world to this individual solopreneur job has been an interesting experience. The thing that’s coming out that you had mentioned is I wrote a chapter in a book for entrepreneurs. Every chapter of the book is a different woman’s experience launching her individual business and what she has shared with others as a toolkit for those who are thinking about starting their own business.

Fred Diamond: You’re in your third year now. Again, it’s really interesting because we worked very closely for a portion of my time when I was a consultant going by the name of Diamond Strategic Marketing. Microsoft for a couple of years was one of my big clients. Luckily I found a VP who you reported to who liked me and brought me in, got me a contract, and I was working with a lot of the partners, and I knew you in the corporate space, and Microsoft is as corporate as it gets. Tell me about your mindset right now. Again, you’re three years in, and we’re also Facebook friends, so I see some really cool posts that you’re doing. Give me a little bit of a sense of, again, you are a 20-year corporate sales veteran, I believe you were at Microsoft close to 14, 15 years. Give me a little insight into your mindset right now as you’re helping women achieve more out of life.

Lisa Malone: It’s interesting how what I did for so many years is now applying. I coach myself basically. As a channel manager, you’re assigned implementation partners so that the software does well for the customer. Your job as a sales manager or channel manager is to work on them with the marketing, their conversions into sales, pre-sales efforts, and then maintaining the customer after the fact so that the experience is good, your reputation is good, all of the things that grow your business. I hear myself now when I don’t want to do work that I’m supposed to be doing, like creating a CRM system, making things automated to help me. Then we have these little arguments inside the head about what I should be doing, and I set myself back to plan for that, to make myself successful by really creating a virtual team for myself that I had in the corporate world.

Fred Diamond: Before we start talking about some of the lessons that you learned as a corporate sales professional that you’re now applying, give us a little more insight into the business that you’re doing right now. Give us a little more insight into exactly what are you doing for women and how are you helping them transform their lives?

Lisa Malone: A professional organizer, you may have seen Marie Kondo or The Home Edit, and those TV shows has gotten really popular. But what I have seen from my angle is that women put themselves last typically. I was the same way. Everyone is coordinated, every child is taken care of, the meals, the house, everything else, and they’ve put themselves last. I found through experience in my clients that when we redo a closet, when we are talking about outfits, the confidence builds, women are coming out like, “I’ve never been happier in my closet before. It’s such a beautiful place, and it inspires me to do more things.” Like they say on the airplane, put the oxygen mask on yourself before so you can help others. It’s that same concept.

Fred Diamond: Give me a typical demograph of a woman that you help, that you support?

Lisa Malone: Interestingly, it’s between 40 and 60 years old. I would say some of them maybe are in their mid to late 30s and they’re exhausted. Their kids are young to middle, or they started having children later in life. They have career jobs, they are overwhelmed, the house is getting away from them, and they really need help. It’s more help than a cleaning crew. It is organizing so that the home spaces are calm so that when they come home to their house, it’s an oasis, not another task that they have to deal with and that they’re overwhelmed by.

Fred Diamond: What brings you the most joy in doing this?

Lisa Malone: Making them so happy. I’ve seen relationships transform where a client is like, “This is it. I’ve had it. Potentially we might be selling this house.” The relationship might be over too. Loving, caring, conversation, teamwork, building. Literally, you do not realize how the clutter and chaos seeps into your world, your mindset, your approach to life. It’s depressing. We suggest as a professional organizer to start with your bedroom and your closet first because that’s your quiet time. You’re going to sleep in that space. You’re waking up in that space, and it really does make a difference in your day in how you approach whatever it is you’re doing in the day.

Fred Diamond: Obviously, we do Sales Game Changers Podcasts all the time. We post shows every Monday, every Wednesday. One out of every three show we do is focused on women in sales. Obviously, over the last three years, a lot has changed for pretty much everybody on the planet. Every single person on the planet has some degree of change. As a result of what you’re doing based on the last three years, could you have done this four years ago?

Lisa Malone: It evolved because I had retired to career 2.0 and I was thinking about starting a small business. I wasn’t quite sure what I was going to do, so I naturally rolled into something comfortable, which was an online directory of Microsoft Partners. I pictured myself going to Microsoft events as a guest, not as an employee, and enjoying my friend’s time, just going out there and having fun. But when COVID happened and all the conferences shut down, that ended that. I worked on the directory and I updated it with the latest Microsoft technology, but I was quite frankly bored out of my mind.

If it weren’t for COVID, I would’ve never discovered this passion I have for changing people’s lives and changing people’s homes. People needed offices in their homes. They were working out of a closet or at kids’ playroom, and the kids were home doing distance learning, and the parents were trying to have a career with balls flying in the house while the kids were in virtual gym class. It was crazy and I would’ve never have predicted this for myself, but one of my Microsoft managers along the way had told me, “If you do what you love, the money will follow.” I was like, “Okay, well, that’s so interesting. What does it look like for me?” It’s just so interesting how things unfold when you’re looking for those. You walk through the open window or door and just see what happens.

Fred Diamond: That’s an interesting quote, when you do what you love, the money will flow. Yes, and you have to be doing the right things. Who knows what the right things are? You’re three years into the business, the Institute for Excellence in Sales has been around for 11 years, I’m learning things every minute. With suggestions, things change, what’s the right way to go? What’s important for our customers? I’m curious, again, you worked for one of the top companies in the history of the planet, Microsoft, you were there for closer to 14 years. You worked in corporate sales and you worked with partners. What were some of the lessons that you took, or some of the knowledge that you took as a corporate sales professional at Microsoft to help you grow and launch your business?

Lisa Malone: I realized that when I am passionate about what I’m doing, and I care about that person, not me getting the sale or not me closing this client, I want that person to know, truly, this is for you. It’s a luxury service, you deserve these things. But I realized the same thing happened at Microsoft. When I was working with the partners and I really had the partner in mind versus myself, my numbers, my quota, it just was such a better partnership. I think that’s why our relationship is as good as it is, and all my partners, is because we really were a team. I think that can be the same for clients and customers. Get out of your head and your priorities and what you need to be doing and think about what’s in it for that customer, what’s in it for them, and how can you help them with what they’re doing, not yourself.

Fred Diamond: Partner’s a two-way street and the best relationships that you have aren’t just you from Microsoft to them. There’s a lot of expectations of course, but it happens over time. A company like Microsoft or an IBM is you have partners for years because that’s the business they’re in. This is the business that I’m in. It takes time for a business to grow. We’re serving mutual customers. You and I are both in the Washington DC area, generally the mid-Atlantic, the big customer, of course, is the government. Most people who work for the government aren’t going to leave. They’re going to stay in their jobs for their whole careers. You’re working with the vendor, you’re working with the partner, and then you’re servicing the customer.

I remember once, I did a lot of consulting to small companies, and there was this one particular company that was interviewing someone to come on board as a BD professional. The guy worked at IBM and I interviewed him. I said, “Why do you think you’ll be successful?” He said, “Well, I worked in the entrepreneurial division at IBM and we were helping startup type things.” He said, “So I’m perfect for this type of a job.” I said, “Yeah, you were in the entrepreneurial division at IBM. Every 10 feet there’s a copy machine. You got paid on time. You had world-class benefits. There was a kitchen everywhere you needed. There were administrative assistances all over the place. Yeah. You were entrepreneurial at IBM.” You were at Microsoft, very similar. A lot of support. We had beautiful buildings that were always on the leading edge of innovation. You had beautiful conferences. You were just at the forefront of supporting employees and being a good citizen. Now you’re on your own. You have to wear every hat. There’s not that, “Hey, can you …” There’s no assistant around because there’s no assistant. Talk about the challenge as an entrepreneur of wearing every hat when you had this world-class support team.

Lisa Malone: It’s overwhelming. I think that the more you think about it and stew on it, the more it freezes you up. What I have done on every day is just say, “What are we doing today? What are our top priorities? What are the priorities that I want?” That was also a switch, is that corporate dictates here’s your priority, but it’s nice when it’s in your hands because you can say, “All right, everything we need to do today needs to generate money.” Talking to a friend is making money, it is networking. When you relate it to that, it’s not as overwhelming. It’s like, just start, just do things. There’s so many things at our fingertips now, and not to get geeky, but that AI, I know how to talk about professional organizing, and I had a journalism degree from Ohio State. I know how to write, but I ask the AI tool, like, “What are the top five things about professional organizing?” It comes up with these answers, and I just know that I’m covering all the bases.

There’s so many things now that help you, like tutorials and all of that. Anyway, I’m getting off topic, but that’s how I go through my day, is just making sure I’m doing something to move the dial. Of course, I’m a wonderful procrastinator, I do run off, but I try to reset myself, my mindset, and be like, all right, go ahead, take a break, walk around, or whatever. But what can we do that’s creative that will get the juices flowing and never think of it as, “Oh God, I got to do it again.” Here we are another day, I don’t know what I’m doing. If that’s the case, go back, get a job, work for somebody else. You don’t need to be depressed about it. You want to find that, because that’s where the opportunities flow, and telling everyone what you want to do, whether you are screaming it from the rooftops or just telling everyone that you come across, people don’t feel like you’re pitching them. They just see you so excited in what you’re doing and they want to help you. All the opportunities come from there.

Fred Diamond: After you left Microsoft, you went to another company. It’s a great story that you’re telling us. You worked in corporate and the reality is when you work in corporate, you’re working for the company. You could even be creative and entrepreneurial. Again, we talked about how Microsoft in a lot of ways was a great place to work, but you still had a quota and you were committed to selling Microsoft technology at the end of the day. Generally, they treated you well, as a lot of big companies do. A lot of big companies like the Salesforces of the world and the Apples, they treat their people well, but you’re giving up yourself.

Now you’re entrepreneur, you’re all about Lisa Malone Industries, even though your company’s called You Have Arrived!. You’re the president. I tell people when they go to work for themselves, you’re the VP of sales for Fred Diamond Industries, or Lisa Malone Industries, you still got to get sales. I’m just curious, do you miss anything about the corporate world? Of course, it’s changed. The whole world has changed. There’s layoffs going on now. Microsoft has gone through so many iterations at the end of the day, cloud, and all those things. Things have definitely changed from what they were 5, 10, 20 years ago of course. Do you miss anything about working in corporate as compared to being a proprietor?

Lisa Malone: Yes. I miss having work friends. I’ve gone out and built my own group of work friends. I’ve networked with every professional organizer in the area, and we get together, and it’s just the camaraderie. It’s like working from home. You don’t go to the water cooler and run into anyone, and you really don’t run into anyone now. I’m grateful not to have eight hours of Zoom calls a day to be able to see my coworkers. But just missing that. I’ll go to conferences and stuff like that and make new friends. Online, it is such a welcoming environment. It’s surprising how much of a partnership other professional organizers are. I partnered with a stylist to create You Have Arrived!. We have an amazing relationship and partnership. That’s what I do miss. I miss creating new best friends every time there’s a new team to be working with, so making friends.

Fred Diamond: At one point I went to work for myself in 2002 and I used to sometimes say that the worst part of it was that the refrigerator is right there all the time, and you’re still in great shape. Good for you. But it was the water cooler conversations. It was the Monday morning, “Hey, what’d you do for this weekend?” There’s a lot of people online. I got so many people online, I could be talking to people all day, but it’s the human touch. Of course, the pandemic has taken a lot of that away from us. I’m curious on a little bit of a different twist. Again, the Institute for Excellence in Sales, we help employers attract, retain, motivate, and elevate top tier talent, specifically for women in sales and minorities in sales. One of our big programs, of course, is our Women in Sales Leadership Forum, which is run by Gina Stracuzzi. How is your business approach different as a woman than what you have seen working with and managing men?

Lisa Malone: Interesting you should say that, because I just shared this with my husband who’s a small business owner and sold his company, so now he’s working in corporate. Women are so different than men. It’s almost a community. We talk about manifesting success and all that. It’s funny because, he’ll be embarrassed when I’m saying this about him, but he rolled his eyes like, “Ugh, manifesting,” but it’s the truth. The more you talk about what you’re doing and say, “I want to make a million dollars in revenue this year.” People are like, “Well, that’s interesting. Tell me more about it.” It’s just a supportive approach. I’m not bashing men or whatever, but it’s not the old boys club. I was really the only woman in the room for so many years between the partners and the customers. I didn’t really notice because it was just my world. I only have brothers, I only have sons, but it’s just so great to be with other women.

I went to a conference and one woman got up to get herself a glass of water and she turned to me and said, “Can I get you a glass of water while I’m up?” I’m like, “Oh my God, yes.” No one has ever asked me that. It’s a great space. I highly recommend finding a network of women who just can relate to what your life is like, what you’re dealing with, how many things you’re juggling, and just make you feel like you’re not abnormal. People are there for you and find your cheerleaders.

Fred Diamond: You just mentioned something that we hear all the time, when you said you were the only woman in the room. One of the of big programs of the IES, Institute for Excellence in Sales is our women in sales program, and I’ve heard that a hundred times. We weren’t planning on talking about this, but since you’ve had such a long and successful career in corporate at Microsoft and a couple of other companies before you created You Have Arrived!, what would be your advice? Because we have a lot of young women sales professionals who listen to the Sales Game Changers Podcast and read the transcript to the show. I don’t want to ask a trite question, like, what would you tell the younger Lisa Malone, but what would be two things that you would tell a woman in sales, let’s say she’s in her late 20s, early 30s, or getting started. Because a lot of the great companies are hiring more women as women see sales, corporate sales, as a career opportunity, what would be some of your advice for them to think about and to apply to be successful?

Lisa Malone: I would say don’t be so nervous to walk into that room. Because if you look at the body language of men, they’re just doing their thing. They’re just as nervous as you are. They’re not very confident, no one’s confident. It’s just how you portray yourself and walk into the room and be like, “Hello, I’m so-and-so.” Don’t shrink. Don’t think you got to sit in the back of the room. I like to sit at the end of the table, mostly because I like to see all the faces and it’s a power seat, but I don’t look at it as that. I don’t try to do a power play. I just want to make sure I can see everyone and hear what they’re saying and be my authentic self. I think that’s what makes you taken seriously. Of course, you could talk about clothing and how you want to portray. What you feel on the inside needs to show on the outside. You want to be taken seriously. You want to be thoughtful in what you’re saying. But you don’t want to shrink. You don’t want your voice not to be heard because you’re worried what people are going to think of you. Be yourself.

Fred Diamond: You were hired to the company. You deserve to be in the room. You deserve to have your voice heard. We’ve heard that so many times. All right. We talked today with Lisa Malone. She’s a professional organizer. Her company’s called You Have Arrived!. She has a course to help women organize, not just the closets, but their whole house, pretty much?

Lisa Malone: Yes. I’ve done whole houses. I’m starting to scale back to doing boutique spaces. That’s any closet, or makeup, and bathrooms, and that kind of thing. Only because again, you start with these small spaces and then it evolves the whole space. When the women are hiring me to do their whole house, I like to start with their path as they walk in the house, the kitchen area, so that when they’re coming home, they’re calm and then we jump straight to the bedroom and the closet. What are you doing when you’re waking up? What does your bathroom look like? How are you taking care of yourself?

Fred Diamond: You had a nice illustrious career working at Microsoft and you did very well for yourself there. Now you’re working for yourself and you seem so alive. Again, we’ve been friends for a number of years and you’ve always been a bright person, but you seem alive right now, which is amazing. Again, for people who are watching or listening, we’re also recording all our shows on video. When you were at Microsoft, did you think about going to work for yourself at some point? Was that something that you had contemplated? Or did this just one day you just said, “You know what? I’m done with corporate. I still have to earn a living. We still have kids. We got college in the future, et cetera.” Were you thinking about the mentality of going to work for yourself, or not?

Lisa Malone: I honestly was very intimidated by it. Along the way my husband had always encouraged me to quit and do something, but it’s a lot. It’s like there’s something comfortable about where you’re doing well. It’s hard to take that step. Side hustles became a thing. I’m not even sure when side hustles became a thing, but trying a side hustle is like dipping your toe in the water without making that huge jump just to see, is this me? Is this going to work? Everything’s a risk, and like all those people that got laid off at Microsoft, I actually belong to a Facebook group called Microsoft Old Timers. All of these people who’ve been working for 20 and 30 years at Microsoft have been cut. They didn’t expect it. They’re devastated. It’s very emotional, but I want to tell them it’s going to be okay. You’re an incredibly talented human being who’s worked at an incredibly wonderful place for so many years. Take something that you love out of that, that really was your passion and go with that, because that’s where you’ll find your little niche. That’s where you’ll find so many people now that have one to two people businesses that need a complimentary service or person. Try things out in the year. That’s my answer to your question, is no, I didn’t really think I would be this entrepreneur successful person. I get it now. I get follow your passions and the money will flow.

Fred Diamond: Like I tell people, I went to work for myself in 2002. You’re in sales, and you and I talked about this in the pre-interview. If you have a spouse or if you have a child, you’re in sales and my bit of advice for entrepreneurs is always two. One is make sure that your spouse is supportive. Two, you have to let everybody know this is what you’re doing. Especially people who’ve been in corporate for a long time, people are going to want to help you find a job. You were at Microsoft for 20 years and you were just laid off. Okay, I’ll keep my eyes open in case someone’s looking for another partner manager or someone who does solution sales or engineering or whatever it might be.

But if this is where you want to go and so many people are going this direction, you have to let people know, this is what I am doing. I am now a, in Lisa’s case, I’m a professional organizer. This is how I help people. If people say, “Well, gee, I think that Salesforce has some openings.” Thank you. But I’m really looking forward to helping women grow their comfort zones by helping them organize. Those two things I usually advise. Lisa, thank you so much. I just want to acknowledge you. First of all, when we were working together at Microsoft, it was always a joy. It was a great client for me as an independent consultant to have Microsoft as a client.

You and our good friend Christine Zmuda were so helpful in me having Microsoft as a client for five years. It led to a bunch of full, not full-time gigs, because I was working as a consultant, but full-time-ish type client. It was great to work with you back then.

I’m very excited to see your success with You Have Arrived!. Like I’ve mentioned, I think it’s a perfect thing for you and I’m very excited for you, personally, and for the value that you’re bringing so many people out there and getting their house organized, which makes such a difference. It makes such a difference. Especially for women who are very busy with work and managing the household and managing parents that are getting older, and the house gets left by the side and then one day you wake up and it’s like, “What the hell am I doing here? This place is horrible.” Just those things that you’re doing to make them enjoy life more. You’ve given us so many interesting and great ideas. Give us one final action step, something specific people listening to the show right now should do to take their sales career to the next level.

Lisa Malone: I would just say find the one little thing that really lights your fire every day, so you can go to your meetings with that fire. People can tell from your voice if you’re in it or not in it. The one thing that you can do yourself is be in it. Get that energy out there, find fun. Find fun in every day because every day there’s challenges all over the place, and if you just can find that little spark, things will go well for you.

Transcribed by Mariana Badillo

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