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SPI 409: An Interview with Jess, my Executive Assistant (and How We Choreograph Our Work Together)

Back in 2014, I had 9,000 unread items in my inbox. There were a lot of messages from friendly people in Team Flynn that I just couldn’t get to. Then someone entered my world, got me to inbox zero, and became an extremely valuable part of Team SPI.

If you have ever thought that you don’t have enough time to do everything you want to do, you should listen to this podcast episode. Jess, my executive assistant, has made it possible for me to focus on the big picture items on my to-do list. I trust her to do so many things, and look forward to our Monday morning calls. She has just got everything so organized, and, well, it’s time for you to get to know her.

Today’s Guest

Jess Lindgren

Jess Lindgren delights in the details, whether she’s planning your quarterly board meeting, choosing the perfect gift for everyone on your list, or putting the finishing touches on another batch of her famous homemade marshmallows. She and her husband Bob enjoy living in San Diego, and when they’re not relaxing at home with their kitties, you’ll find them practicing yoga, exploring museums, or indulging in theater performances wherever they find themselves around the world.

You’ll Learn

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SPI 409 An Interview with Jess, my Executive Assistant (and How We Choreograph our Work Together)

Pat Flynn: Hey, what’s up team Flynn. I want to start this episode by asking you a question, and if you happen to answer yes to this question, I want you to know that you’re in the right spot. So this would be a great episode if you say yes to the following question: Has time ever been, or the lack-of-time ever been, an issue for you when it comes to running your business and/or the thought of you starting and running your business? If time has ever been an issue for you, well this is an episode that you need to listen to because today we have a very special guest, Jess from Smart Passive Income. That’s right. My executive assistant is on the show today who I hired a while back to initially help me out with my email because one day I looked at my email inbox and saw 10,000 unread emails.

Pat: But Jess, back in episode 115 when I interviewed her before, was just helping me with my email. She has since grown to an executive assistant rockstar, has helped several others learn more about executive assistant stuff. Whether you are an entrepreneur who is or is going to have an executive assistant, or maybe you are an executive assistant and you want to get some insight or looks at what it’s like working with an executive like myself. Well, you’re about to get in on that process right here. So stick around.

Announcer: Welcome to the Smart Passive Income podcast where it’s all about working hard now, so you can sit back and reap the benefits later. And now your host, he likes spicy, but then regrets it later. Pat Flynn.

Pat: Hey, welcome everybody. This is Smart Passive Income session number 409. My name is Pat Flynn and I’m here to help you make more money, save more time, and help more people too. And one of those things that can help you save more time than anything is having an executive assistant to help you with all different things. And I’m just very excited to welcome my executive assistant Jessica here on the show today. So we’re going to cut right to the interview right now. Hey Jess, welcome back to the Smart Passive Income podcast. Welcome.

Jess Lindgren Oh my gosh. Hi. It’s so wonderful to be here.

Pat: It’s been so long since everybody’s heard from you in episode 115 which was a while back, and I know this about you. You have yet to listen to that episode.

Jess: That’s so true. I can’t believe that was back in 2014. I had just started working with you a couple months prior and you’re just like, “Jess, you’re so great. I can’t wait, come on the podcast.” I was like, “Are you kidding? You’re really going to have me do this?”

Pat: Because, you don’t do that.

Jess: I didn’t do that at the time, but now I’ve gotten a little more comfortable with it. But you are so right. Even six years later, I still haven’t listened to it. Can’t bring myself to do it. I’ve skimmed the transcript, so I remember what we talked about. I remember what I was wearing that day. I remember where I was. I remember that I had microphone problems and Mindy on our team just happened to be at the coworking facility and I was like, “Help me, what do I do?”

Pat: And now you’re here back on the podcast. So, we’re going to talk a lot about what has changed, but if you can remember what we chatted about in 115 as a recap for everybody. Maybe we can start there and then just timeline—talk about what has happened since then. So episode 115 and starting with why I hired you, I needed help with the email and that’s what that episode was about.

Jess: That’s really where we started. Pat went from 9,000 unread items in his inbox down to inbox zero, as a result of my coming onto the team and it just… We talked about how to achieve inbox zero, what a big weight off of your shoulders it can really be to get email tamed, whether it’s you personally doing the email or whether it’s hiring someone else to take care of the email for you. Regardless of who’s taking care of it, as long as it’s being done and handled and people are getting their responses, it just frees up so much mental, physical, psychological energy for you to do everything else inside of your business.

Pat: Can you remind people how bad it was when we first started working together?

Jess: Oh my gosh, it literally was 9,000 unread items and I just went oldest to newest. My brain almost melted. Doing that much reading, it was so hard. I didn’t know how hard reading could be, and just getting to know the SPI community and the audience and all the different people and what people say. I came in at a pretty good time. You had given up on answering emails right around your birthday. So, there were a ton of old happy birthday Pat messages. There were a ton of Merry Christmas to you and your family. So lots of really nice, happy, wonderful, friendly people that I got to know by way of digging through the old archives in the inbox. And that was such a cool way to get introduced because I was just… I came from a corporate environment, nobody emails a staffing agency to say, “Hey, thanks so much.” And people just went out of their way to tell you, “Happy birthday. Thank you so much for how you’ve changed my life.” “Merry Christmas, happy Thanksgiving.” So, it was really wonderful to come into this huge slew of just happy, positive, wonderful messages from everybody.

Pat: How might a person, and we’ll talk about this throughout this episode, but the experience of hiring a VA for example, to do that. It was great that you had access to all those emails to get a feel for my audience. How might somebody who hires a VA tomorrow help that person understand who is in the audience if they don’t have that. What would be the best way for a VA to understand who is it that we’re really serving here?

Jess: A really great way to do that is the executive—the person who’s doing the hiring—really needs to make themselves available. It’s a big investment of your time, your effort, your energy at the get go when you hire that person. Whether it’s a virtual assistant, executive assistant, whatever person it is that’s coming into help you run your business more effectively and efficiently. You as the executive, really have to make an investment of your time to be available to answer questions and that kind of thing. But then also just giving your assistant access to any books or programs that you may have produced, and also any books, programs, tools, software that your assistant might need. I remember my last corporate job, I had to beg and beg for years to get Adobe.

Jess: To be able to create PDFs and just do real basic office functions—it was “too expensive.” And so instead of getting the Adobe program, where they could’ve invested a couple hundred bucks, I had to spend… Because this was years ago, this is over 10 years ago that I would have been at that job. And the amount of time that I spent creating PDFs, and other things that Adobe can do, in a roundabout way because they didn’t want to spend the $200, was just maddening. So give your time, your resources, whatever they need, set them up for success because that can only help you.

Pat: Okay, that’s really helpful and we’ll dig in to that a little bit more, but let’s keep going back to when you first started working with me. What were the big psychological things that we could recap that you helped me get over to really help me get to inbox zero and start to feel comfortable again?

Jess: Really a lot of it was just you felt comfortable giving control over to me. I had originally started asking for delegate access, “Hey, I don’t really need to be in your inbox. That’s fine.” But it’s not full control and it’s harder. It’s more complicated to have delegated access than it is to have full access. And that’s a big leap of faith. It’s showing a lot of trust in the other person to say, “Hey, here’s my password to all my email, calendar, all that good stuff, just dive right in.” So just even on your part saying, “I trust you to take this over. I trust that you’re going to do good work with this, that you’re not going to do anything damaging to me, my reputation, my audience,” whoever that might be like, that’s a big leap of trust.

Jess: And then on top of that, we really got you over the psychological barrier of treating email, like text messages. So that was something you used to be, “Oh my gosh, an email just came in.” Ding, ding, your phone is bothering you all day long and you’re just like, “Well this person only sent me a thank you note so I can respond to that later. But this person has a question, I really need to get back to them. But I also need to record this podcast episode and I also need to prepare some slides for a talk. And I also need to do my book outline, but I really need to get back to that email.” So just freeing you up from all of the demands that people had on your time.

Jess: I thought that was really great and setting you on a schedule for when to check your email. Like I said, I haven’t listened to the episode, but you did say in the transcript that, at the time we recorded it back in 2014, you were checking email three to seven times a day. Now when you started, [crosstalk 00:08:45] you were checking 35 times a day. It was 30 or 35 times a day. You were living in your inbox. So we’ve really got you out of that mode and into checking it on a schedule. Now that we’re several years out, how often would you say that you check your email now?

Pat: Not even once a day.

Jess: Awesome.

Pat: Thank you.

Jess: That’s fantastic. No, I love to hear that.

Pat: Yeah. So, tell everybody how we got here.

Jess: How we got here is, just really telling Pat from the get go. I’m like, “Okay, who needs an immediate response from you? Who are those people?” You can name those people on one hand, your wife, your family, your mom and dad. Those people have a direct line of access to you. They know where you live, they know your phone number, they know how to get ahold of you. April can just. “Hey Pat,” from the other room, she has a more direct line of access to you. But people who are emailing you something, even if it’s super urgent, I firmly believe that all of that can wait 24 to 72 business hours. Somebody emails you Friday afternoon, you don’t really owe them a response until Tuesday or Wednesday.

Pat: And you get a sense of when it actually is a real emergency and you let me know when those come up and they’re few and far between.

Jess: They are few and far between, but it’s a lot of practice. It’s an ever evolving thing. As I was reviewing the transcript from the last interview that we did, I was just like “Wow, it doesn’t feel like anything has changed.” But a lot has changed because we don’t say, “Well this is how we did it when we first started working together. So this is how we’re always going to do it.” At the end of our weekly calls, I say, “Any other comments, questions, thoughts, concerns, anything?” The door is open, the table is here. What do you have, what’s working, what’s not? What can we fix, what can we adjust?

Jess: It’s not even necessarily that things are broken but maybe there are bottlenecks, maybe there are just places that things are feeling stuck and both of us feel comfortable to come to the table and say, “Could we tweak this? Could we fix this? This seems to have been working but it’s been six months. Is it really as efficient as it could be? Is there a different tool or software or something that we could be using?” We’re constantly evaluating and improving.

Pat: I think another fun thing to talk about would be how we still get those urgent emails addressed now, and I’ve shared this in person with a number of people and perhaps even a couple of times in podcast episodes here and there. But it just wanted to chat about our email answering process now, especially for those ones that on the surface seem they would need to be a little bit more urgent than just the ones that can wait or there’s general answers already available for those. So what’s our cadence for how do we get those things addressed and how do we do that?

Jess: So the way that it works right now is still pretty similar to how we did it when we first started working together. I work oldest to newest, so whatever came in, (because people always used to try and come in, “I’m going to email him Sunday night or first thing Monday morning and he’s going to see that and respond to that first.”) That’s not how we do it. We go oldest to newest because first in, first out and that way first come first serve, however you want to phrase that. And so going from oldest to newest, definitely, there’s a lot of nuance here. So, every organization is going to have different things that are the burning-fire emergencies. If we had a very urgent, “Oh my gosh, we just launched our new website on Monday, and nobody can search for anything” that needs to be escalated. But if somebody says, “Hey, I’m looking for a resource on how to start a podcast,” that can wait, as we bubble those really urgent burning fire things.

Pat: Right, we’ve canned answers for a lot of those questions too.

Jess: Yeah, yeah. We have canned responses for a lot of that and those are things that we maintain and refine. As you might release new resources or as you might update the archives, that kind of thing, we make sure that links are still current, we make sure that we’re giving the best, most current information. I think your how to start up podcasts tutorial, you update that annually, right?

Pat: Yeah.

Jess: Yeah. So we just make sure that all the best information, if we ever have a question, we just bring it to Pat’s attention and say, “Hey, are we still doing this right?” And go from there.

Pat: And then we do one thing once a week on Monday where we really get to go and actually get my voice still into those emails. But you’re still handling those emails.

Jess: Yeah. So every week, Pat and I have a 30 minute one-on-one and I just maintain—the tool that I use is Google Sheets. I have tried so many things over the years. I’ve tried, I couldn’t even tell you, and I don’t want to bad mouth anything that anybody might really use and love. But I’ve had so many tools and services over the years just not save or the app crashes and then this beautifully constructed list that I had, just disappears. So Google Sheets has treated me very well over the years and it’s just a simple two column spreadsheet. The first column, I always copy and paste the person’s email address because I find that that’s the easiest way to search for the piece of communication.

Jess: And then, I just write what I call an executive summary. So it’s just a one to two sentence, here’s the gist of the email because sometimes people might email us in a novel and how do you distill that without Pat needing to sit down and read and digest the whole thing. I can read and digest it for him and say, “Here is this email from whoever this person might be. Here’s what they want. How do I respond?” So that’s the third column: who’s it from, what do they want, what’s my followup?

Pat: And this is a actual phone call. So we’re not even in person. Jess just calls me 9:00 a.m. on Mondays. I expect this, I know this is coming, and I know it’s important and it’s a nice way to start the week because we can get those list items out of the way and it’s just boom boom boom. I mean how many would you say we get through within a half hour—it depends on the topic because we discussed some of these things and a little sometimes in depth. But we get through a lot.

Jess: We get through a lot. It really depends on the week. So some weeks, this morning when we talked, my list was very short and we were done inside 15 minutes. But sometimes if my list is long, I’m like, “Hey, no time for small talk, we got to get through this. I’ve got 50 items on my list.” And even during those 50 items, we might get through all of them in 30 minutes. That’s ambitious. But sometimes we do. But even while we’re talking, I refine my list Sunday night or Monday morning before we talk. And then I say, “Okay, here’s the stuff that really has to get answered.” So I’m even prioritizing as we talk or sometimes, the answer that you give to question five might also answer question 15.

Jess: So if I get down my list and I say, “Well what you said earlier, nevermind,” or that one can wait until tomorrow. We’re running low on time. So, I would say on average 30 to 40 items when the list is long. But thankfully, lately the list has been a little bit shorter and that actually is great because it gives us time to… We’re preparing for FlynnCon2 and we can really go into, “What do you think about this topic? Well here’s what we’re working on this month for the event.” Gives us a little room to chat about that stuff too.

Pat: This is as opposed to me going into an urgent folder in email and having to then read every single one from scratch without knowing any context and then figuring out an answer or typing them out, which would take longer. So Jess does a lot of the hard work for me up front to filter—which emails do I need to see, and then instead of me still going in there and actually answering them by typing it out, Jess and I, we discuss it, I give her an answer. Then what do you do after I give you an answer, for example?

Jess: After you give me an answer, I never answer an email pretending to be Pat. I never say, “Yeah, Hey Pat here” because a couple of things, you and I have very different written voices. I learned how to type on a typewriter, so I still double space, even though that’s probably a crime to a lot of people, but so we have very different written voices, punctuation, written style, that kind of thing. So one, I never pretend to be Pat. Two, what if I say something and even though that is what you might say, someone might come back and say, “Well you said XYZ thing” and you think to yourself, “Well, no. I didn’t.” So I don’t ever want to be putting words in your mouth even though I think I might know what those words are.

Jess: So I just say, “Hey Joe, Jess here on Pat’s behalf, I spoke with him this morning. Here is the answer to your question,” and then I’ll just verbatim whatever you dictated, say that this is it or if it seems appropriate for me to re type it in my… Here’s what we discussed, here’s the answer. But yeah, I do the heavy lifting then, from that end. But you’ve made the decision, you’ve been involved in the email and making sure that it is handled in the way that you want. But then, yeah.

Pat: And I love that we get so much done that way. And I know that for example, if people email you with a question that you know, I need to learn about myself, you go… Correct me if I’m wrong. You go, “Hey Joe, I’m going to have a chat with Pat on Monday. We’ll get back to you soon after that.” And do you ever get a response going like, “No, I need Pat to answer.”

Jess: No. I mean a lot of it is just expectation management. So if you just let an email go untended at all, that’s when people are like, “Hello, is anybody there? Are you getting this?” And that’s when you get escalated. “I emailed you on Monday, it’s now Tuesday. I can’t believe you haven’t gotten back to me.” If you just get back to him with a quick, “Hey Jess here on Pat’s behalf, I will speak with him next week and get back to you.” If you say, “We’ve received your email, here’s when you can expect a response from us.” But then you have to… The third part about that is you actually have to keep your word and you say, “I’m going to get back to you next week,” you have to get back to them next week. But by and large, we’re so fortunate. Everybody who listens to the podcast, reads the blog, has ever attended one of your talks over the years. We have the best fans and people.

Pat: They are the best, seriously.

Jess: I’m just going to tell you right now, if you’ve ever been to an event where I’ve been there, I tell everybody who comes, I’m just like, “If it wasn’t for the SPI community, I mean Pat is awesome too, but if it wasn’t for the SPI community, I wouldn’t still be here.” Everybody is so nice, everybody is… And especially when I say, “Hey, we’ll get back to you in a week.” All anybody says is, “Oh my gosh, thank you so much for letting me know.” And even if I’m, let’s say, I get sick on Monday and I don’t get back to them right when I say I would, “Hey Jess, I know you said you’d get back to me on Monday. It’s Tuesday now.” And I’m like, “Oh my gosh. Yes. I’m so sorry.” “No, it’s great. Thanks so much.” Everybody is so understanding, so wonderful and just thoughtful and considerate and incredible with their replies. So, thank you.

Pat: Yeah. If you’re listening to this team Flynn, you’re amazing. #TeamFlynnforthewin, for sure. As a result of showing up in the email and going to some of the events and whatnot, the San Diego entrepreneurs meet up here. People have been getting to know you now, which is really neat. So no longer are you just behind the scenes and tapping your fingers on the keyboard, you’re showing up, you’re having conversations, people are getting to know you and you’ve been able to befriend a lot of the SPI community as well. What’s it been like to have that be a result of working under the SPI brand and what we’ve done together?

Jess: It’s really amazing. I can’t stress that enough. Coming from a corporate background, I was lucky if I might talk to some of my coworkers once a week and it was always very cold. I don’t know if that sounds harsh, but you just have… I mean you’ve worked in an office before?

Pat: Yeah, surface level, very professional.

Jess: It’s surface level, that’s what we’re looking for here. Very surface level, very professional, very, “What’d you do this weekend? How’s the cats? How is… whatever,” and it just doesn’t really go any deeper than that. I have made some of the most amazing friendships just from, like you said, the local SD entrepreneurs group. Whenever we travel and speak: conference organizers, the different AV teams that we interface with when you speak, just I have the workshop students, all the people that come here to San Diego for our workshops. That’s actually why I moved to San Diego. We did our first workshop. [crosstalk 00:20:42] Yes.

Pat: If you didn’t know Jess lives in San Diego now. She moved here to work with me and I’m just so thankful and blessed and I feel so grateful that you’re here. And I’m sure you’re loving the weather too.

Jess: Oh my gosh, this is incredible. I mean, I’m originally from Minneapolis, Minnesota, and we were just there a few months ago for Thanksgiving. And the first day we were there, we got a foot of snow and over the five days we were there, snow, rain, ice, sleet, all of it. And the instant I got home, I was just like, “Wow, 65 and cloudy. It’s hot here. It’s hot in San Diego. This is fantastic.” Yes. So we love it here in San Diego. But truly after that first Power Up Podcasting live workshop that we ran in 2017, after that workshop, I called my husband from the detergent aisle at target. I don’t even know why I was in the detergent aisle; I was staying at an Airbnb. I did not need laundry detergent, but I’m at target and I called him and I was just like, “So, we’re moving to San Diego.” And he’s like, “Okay.” He’d literally never been here.

Pat: He’s awesome.

Jess: Sight unseen, my husband Bob was just like, “Yep. All right, cool.” But yes, the SPI community, team Flynn, you’re the reason that I’m still here. You’re the reason that I’m even more here, more present in San Diego and Pat, you’re a really awesome bonus to that.

Pat: Thank you. And it’s why you’re here in the studio right now, recording this podcast, right buddy. Not just to give an update, but we’re going to talk a lot more about tips so that you and your VA can have a great relationship. You’re an executive assistant and you’re doing a lot more than email now. Can you run a list of all the responsibilities and things that you’re dealing with now or participating in?

Jess: Yeah. Back when Pat and I started working together in 2014—he and I were just talking about this—the only thing that he sold was the Let Go digital book on Amazon. That was it. That was the only thing. And truth be told, we gave more copies away of that than we sold. You would go on interviews and say, “Hey, if you want a copy of my book, just send me an email and we’ll send it over to you.” So I remember doing a lot of that when I first started and then it just really ramped up from there. It was Let Go, the digital book, and then—what happened first was Will It Fly? first, before the courses?

Pat: Yes.

Jess: Yeah. So you wrote your bestselling book, Will It Fly??. I was in Arizona visiting my grandparents when that book hit the… Is it New York Times or Wall Street Journal?

Pat: Wall Street Journal. Yeah.

Jess: The Wall Street Journal bestseller list. I was visiting my grandparents while that happened. And then we just started developing courses and building a huge cohort of students who take all of our courses on podcasting, affiliate marketing, and smart from scratch—building your idea into your own business. So, I’ve been very involved in building the student community and supporting the student community for the last few years. You wrote SuperFans very recently, and then your speaking has just, every year, your demand, just skyrockets. People see you and they’re like, “We saw you at Social Media Marketing World. We’ve got to have you on our stage.” So a lot of support for your speaking and travel in addition to books and courses.

Pat: The arrangements for travel for sure. But you’ve been even coming to some of these events as well to support, especially the bigger ones where I have a lot of things going on and I need a right hand person to help manage my time and just keep me going through the crowds because sometimes it gets crazy, and we’ve also gotten to become really good friends and learn a lot about each other and how each other works and it’s developed into this amazing relationship. I’d love for us to speak a little bit about some of the things that we’re open with each other about so that we can work better together so that we could help each other out.

Pat: There are some things that on the surface might seem weird in terms of just needs that we have for each other to help each other out. And this is largely based off of events past, and how… I know for you specifically, if you don’t mind talking about it, your previous position before working for me it was very tough and there was a lot of things that worried you about, well how might we work together and is it going to be the same? Can you talk a little bit about that and what we’ve decided to do coming out of that and it might again seem really small but to you it’s really big.

Jess: Yeah, the last role, like you said, it was really tough. The person that I was supporting—from my perspective— really treated me like a whipping post, a scapegoat, “My assistant botched that, my assistant messed this up.” Definitely thrown under the bus all the time and treated really poorly. And I was just like, “All right, if these people can make $50 million a year, I can figure out how to make $50,000, I can do a salary,” quit my job, somehow, I mean just a chance encounter, got hooked up with Pat and we’ve been working together ever since. And I remember probably six months to a year in, you had really started traveling more and you would always ask me and you weren’t rude or demanding or anything, but you’re just like, “Hey, you promised you’d make me this itinerary for my travel.”

Jess: You said that’s something that I can do and it would be really helpful. I would love to see all my stuff in one place” and I would always drag my feet. I was always giving to them my super last minute and really worried about what is Pat going to think about this. Is he going to get mad at me because again my old position, if there was even one tiny typo, I would get berated for weeks. Just I wouldn’t hear the end of it if there was one thing even slightly wrong. So, it translated into working with you. I was really scared. “What is he going to think about this itinerary that is that I’m going to give him. Is he going to think it’s okay? Is he going to think it’s horrible? What if I make a mistake? Oh my gosh.” I seriously beat myself up for months before I even brought it up to you.

Jess: And then one day, I just steeled myself and I was like, “Okay, just take the bull by the horns, just tell Pat what you’re thinking. He’s a pretty reasonable guy. I don’t think he’s going to scream at you. I don’t think he’s going to yell at you. I don’t think he’s going to fire you.” That would be so silly. Why would you think that? And so I did. I just sat you down one day during one of our check-ins that we had talked about, snd I said, “Okay, I have something to talk to you about. And what was your thought?

Pat: I was like, oh my God, are you leaving? Please don’t leave me.

Jess: No. So I’m super serious. I’m like, “Okay, we have to talk,” and that’s never a good thing when somebody gives you that, “We have to talk.”

Pat: Or it’s like, “What did I do? I’m going through previous interactions to go, “Did I say something or did I miss something that I…” all that stuff. But you were just very open and honest with me.

Jess: Yeah. And from my perspective, I thought my voice was shaking. I thought I was talking super loud. I thought I was asking for too much, and I just said to him, “In a previous position, I used to really get thrown under the bus, really treated poorly if I made even the tiniest mistake.” And truly these travel itineraries were the worst of it because that executive traveled a lot and would just scrutinize them down to the detail and just really got upset if there was any mistake. So Pat, for me, if you could, this is going to sound silly, but when I give you an itinerary, if you could just tell me, “Hey Jess, these itineraries are so helpful. Oh my gosh. April loves these itineraries. I can print a copy and leave it at home and April knows exactly what I’m up to, where I’m at. If she needs to get ahold of me. I print a copy and keep it in my backpack when I travel so I can just quickly reference stuff.”

Jess: “I love the way that you put everything into my calendar so that I can just one click to find all my information for my flight.” I really needed that verbal affirmation, I needed Pat telling me, “Hey, you’re doing a great job here.” Words of affirmation is not really my love language for most things in my life. But for this one specific thing I was just like, okay, this gives me so much anxiety. You’re not the same person as my last executive, but it has translated. It’s transferred to this new role that I’m playing with you and your organization. So this is how I think I could fix it. This is what would fix it for me. If you told me how great they are, how helpful they are, even if you don’t mean it, I don’t care, just tell me. And that will hopefully help me feel more confident about that one area for such a small thing. Yeah. And it’s been really helpful.

Pat: Good, and they continue to be helpful by the way. Keep doing them. April and I both love them. Thank you for that. What’s the big lesson here for anybody working with an assistant when it comes to this openness? What’s the big takeaway?

Jess: The big takeaway is the assistant has to feel comfortable coming to the executive with what they see or feel as a problem. Even if it’s one-sided, I thought it was a problem. You didn’t think it was a problem, I don’t think.

Pat: No. But I listened and I acknowledged and I want to support you. Right. And so what did that do for the rest of the things, knowing that I was there and I heard you and I was going to do that for you.

Jess: Really what it did is just reinforce that you are what I thought. A great guy, you’re reasonable, you’ve got a cool head on your shoulders, you’re not going to flip out about really small stuff. And just made me feel more confident in everything that I did. Anytime that I had a problem, no matter how big or how small, “Hey, can we talk about this thing,” and I don’t even cloak it anymore in like, “Hey, we need to talk.” I’m just like, “Hey, here’s this thing, let’s talk about it.” So Pat’s done a really great job of creating a welcoming, supportive, safe environment.

Pat: That’s a good word.

Jess: Yeah. And just like a really great space to say, “No topic is too big or too small. No topic is too hard or too soft, just come talk to me about it.” And there’s been a lot of professional stuff, but even personal stuff when I’m like, “Hey, I got sick,” and you’re like, “Can I send you chicken soup?” I’m like, “Oh my God,” where does this safe space end? It doesn’t. So Pat’s just, —yeah, you’ve done a really great job from my perspective as your assistant of creating that space for us to talk about anything and everything.

Pat: So would you imagine that a person having just hired somebody to express that expectation up front that everything’s cool, you’re welcome to tell me anything. Is that a smart thing to do up front or is this something that just happens over time through your leadership type and just your care for the other person?

Jess: I think it’s a mix of both. You definitely need to set that expectation, that you as the executive you say, hey this is a safe space for you to talk to me about things but maybe even you have to set the example of…” “Hey Jess, here’s a thing that I need to talk to you about.” So, lead by example in that realm and say “Here’s something that I’m struggling with. Could you help me?” Because I think there is a little bit of a line maybe, you don’t need to air all your personal laundry…

Pat: Of course.

Jess: Airing on the professional side and then the personal side comes with time. But definitely from a professional standpoint, set the tone, set the expectation because it’s one thing to hear somebody say something like that, but it’s another thing to see someone do something like that.

Pat: What other tips might you recommend for a person who is new to working with somebody under them or is about to hire somebody? What are just… Let’s list off a whole bunch of recommendations that you have for the executive to make sure this relationship’s going to grow and turn into something helpful.

Jess: Absolutely. Yeah. So, when you are hiring someone, hire somebody that you like. Hire somebody that you feel like you can trust. There’s a lot of that that comes with time.

Pat: You’re going to talk to them a lot.

Jess: You’re going to talk to them a lot. You will. Because Pat, I think you would had maybe a couple of VA’s over the years.

Pat: Yeah. VA’s in the Philippines and they were amazing. They did all the work that they were supposed to do, but very little communication outside of just the tasks itself and not really any care for stuff outside of that work, which is why I wanted to hire somebody in the US who is more… This is who we’re serving. If we could come up with ideas together, that’d be amazing. We’re in this together. Yeah, I’ve worked with people before.

Jess: Yeah. But this is the first true executive assistant, more involved, more intuitive, go above and… Not even above and beyond, but go deeper into things. So again, if you’re looking for somebody that you like, somebody that you feel you can trust, because truly, every person that I’ve ever worked with, I can tell from the time if I shake their hand. Obviously you and I didn’t shake hands until a couple of years later, we had a video meeting. I think I remember that. I think you had just moved into your home. Kai was a baby, a teeny tiny baby. She was so small and I was just like, “Who’s this Pat guy?” But we had a really great phone call and just went from there. And you start small and you build that. Yes. So you start small, don’t give somebody the keys to the castle. Give them the code to the garage and then lock the door.

Pat: We started with email, in 115, you can listen to that episode. And then we’ve just as you’ve heard, grown from there, travel with support for events and now it’s even as big as you taking a major role in the experience that people and our guests have at FlynnCon. And that’s so amazing. And a part of that is just me knowing where you want to go and how do you want to grow and always being open and conscious about that.

Jess: And that’s my other big tip. Something that really drove me out of corporate was the expectation that as an executive assistant, you personally do all of the loose ends. There was a big expectation that I should be able to and absolutely should take on bookkeeping, accounting, that kind of stuff. I am not good at that stuff at all. I can find you and hire you and manage a bookkeeper and accountant, that kind of thing. But I can’t do that work for you. So, really just respecting your assistant’s boundaries, skills, lean into their skills. Don’t try to force a square peg into a round hole.

Pat: Yeah. And then tips for perhaps the assistant that’s listening to this that you might have to help them not just serve their executive but also remain happy and thrive and do good work.

Jess: Yeah. For the executive assistant, virtual assistant, anybody in an assistant type role, receptionist, administrative assistant, whatever your title might fall to, take care of you. That’s probably the biggest thing that I’ve learned over the last five, six years is taking care of me, enables me to take better care of you.

Pat: What do you mean by taking care of yourself?

Jess: Taking care of yourself means eat better, exercise more. I gave up wearing high heels years ago. I only wear flats because I’m walking at a conference I might walk 10 miles inside of a convention center. I’m not doing that in high heels. Every day of FlynnCon, I took an Epsom salt bath every night even though I was only averaging six hours of sleep. One of those hours was like, “Okay, go back to the hotel room, take a bath, relax.” Take care of your body, take care of your body and your person before you can take care of somebody else. So that’s the biggest thing that I would really offer to any assistant is make sure that you’re being taken care of. Don’t be afraid when you’re interviewing, ask questions, research the person that you’re going to be working with, the company you’re going to be working at.

Jess: That was always something when I was interviewing, you get to that awkward, “Do you have any questions?” And I’m like, “No, I guess, when do I start? What’s my salary?” No, have some really good, thoughtful, don’t be afraid to show your personality a little bit when you’re meeting with that person for the first time, show that you did a little bit of research and that you’re interested in whatever the topic is, that the person is involved in, and have good boundaries. That was something when you and I started, I’m just like, “Hey, I’m available like 9:00 a.m. to 6:00 p.m. but after that…” because I was a contractor, I was just like, “If you bug me, midnight central, I’m going to charge you double.”

Jess: I’m not even joking. But it was really great to set those expectations and boundaries from the get go because Pat very rarely would bother me for something, and I don’t think it even was like, “No, I can’t afford to bother her.” It was just like, “No, Jess, she’s at home, it’s family time. She’s on vacation.” That kind of thing, just really set and respect those boundaries from the get go because it’s way too easy. A personal assistant, executive assistant, it’s a role that blurs the lines between professional and personal needs sometimes. And if you set those expectations upfront, it’s easier for both you and your executive to respect and maintain them.

Pat: How would you recommend an assistant who is feeling a little worried about how the executive may be feeling about the work that they do? Maybe they are unsure of whether or not they’re doing a good job and they haven’t gotten any good feedback and just they’re starting to feel a little bit of anxiety. How might you recommend an assistant figure that out or approach the person they’re working for?

Jess: Definitely take stock of the person that you’re working with. How do they like to be approached? When do they like to be approached, and then speak their language. That’s something that most assistants are really great at, is being adaptable to different communication styles. So, if your executive really likes a latte first thing in the morning, pick a time and you say, “Hey Pat, you and I need… I’m going to make you this latte and then we’re going to sit down and chat.” Or if the person very no nonsense, no BS, you can just sit them down and say, “Hey, I’m having questions about this. Can we talk about it?” So, really it’s a… What I’m looking for here is you need to know yourself fairly well, but you also need to know your executive, so that you can meet in the middle.

Pat: How might you recommend if an assistant actually does mess up in some way, which is no assistant’s perfect. But let’s say you mess up on something, what’s the best way to handle that?

Jess: I love that question. The best way to handle that is own up to the fact that you messed up. Just say, “Hey, I will be the first person, I want to tell you before you find out that I messed up.” Or if the executive does find out first just say, “Yep, that was me. Yep, I messed that up. How can we be better going forward? What can we do? Here’s where I think the communication breakdown was. Here’s where I think, something’s slipped through the cracks,” maybe that we forgot-

Pat: Is that the executive saying that or the assistant saying that?

Jess: The executive assistant. The executive assistant needs to own whatever the mistake was and then say, “Okay, you missed your connecting flight, what happened? And it’s not even to throw anybody under the bus. It’s not to point fingers or put blame on someone’s shoulders. It’s how can we be better? How can we do this differently next time, so that it doesn’t happen again?”

Pat: Right. And that’s the big thing I think a lot of people are just wanting to make sure is that the mistakes don’t continue to happen. But hopefully, most levelheaded people understand that nobody’s perfect and as long as the person owns up to their mistake, we can improve and make things better for the next time. Man, it’s been great catching up, Jess. It’s been a lot of fun and I hope this has been fun for you listening to see just how much Jess’s grown in the company, a well-deserved obviously and how much more she’s going to be showing up in the future for all of you. You’ve likely gotten to know her via email, you’ve gotten to know her now here on the podcast and hopefully if you haven’t yet done so, you’ll be able to meet her in person, maybe at FlynnCon or some other event in the future. And any final words of advice for those listening?

Jess: Really just know as an executive assistant, you are doing such a great job. You move mountains every single day and you’re doing amazing work that enables your executive-

Pat: So important.

Jess: … To do what they do best. And I think executive assistants are largely underappreciated. Whatever your love language might be, I’m sure that all of you love hearing that you’re doing a great job. Let me be the first person today to tell you, you are doing such a great job. Every single day that you show up to work, every single day that your executive is out doing what they do, you are such a big part of making that happen and it’s so important and you’re wonderful and I just love you all.

Pat: And if you have an assistant and they’re not listening to this, but you know that they are doing great work for you, now would be a good time to just let them know and recognize that, if you haven’t done so already. Thanks Jess, appreciate you being here. All right. I hope you enjoyed listening to Jess here on the podcast and to consider just where she was in episode 115 and still having not listened to that episode. I think Jess, I know maybe you’re going to listen to this, but you’re a rock star. Thank you so much for what you do for me, and I know a lot of people have come up to you to say the same thing. But hopefully this is a helpful episode for you, the entrepreneur or you, the executive assistant who is helping an entrepreneur and just know this is just so insightful.

Pat: So Jess, you’re awesome. Thank you so much. If you’ve gotten value from the show, let me know on Instagram or Twitter at Pat Flynn. I want to hear what you think and then finally, you can check out the show notes and links to things that we mentioned at smartpassiveincome.com/session 409. Once again, smartpassiveincome.com/session409. On behalf of myself and Jess, just thank you so much for listening, and being a part of team Flynn, for subscribing to the show and as always, Team Flynn for the win. Peace.

Announcer: Thanks for listening to the Smart Passive Income podcast at www.smartpassiveincome.com.


Smart Passive Income Podcast

with Pat Flynn

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