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I hired Jess, my assistant, to get my email inbox — with 9,000 unread messages — under control. She soon had me at inbox zero and our relationship blossomed from there. Jess is a total pro when it comes to assisting, admin work, and much more — she actually has a podcast on the subject at AskanAssistant.com.
Administrative Professionals Day is on April 21st this year, so I figured it was a good time to get Jess back on the show. I mean really, you should find ways to show appreciation for your assistants, admins, and everyone on your team year-round. But the importance of having a dedicated assistant or admin as an entrepreneur cannot be overstated (based on my experience).
So, how do you show appreciation to someone who basically acts as an extension of your entrepreneurial self? Or, how do you resolve conflict with an assistant, what do you do if they're not the right fit? We're going to get into all of that, discuss how Jess's role with SPI has evolved over the years, and a lot more. She's such a blast to work with and I'm so grateful that she's on the show with me today. Let's go!
P.S. — If you want to see how far Jess has come since we started working together, you can listen to our episode together all the way back in Session 115.
Jess has worked in the C-Suite of organizations great and small for 18+ years. She focuses on supporting her current CEO in his many endeavors, improving working relationships between EAs and CEOs, and has a very low tolerance for any meeting that should have been an email. Jess hosts the wildly popular* business podcast, Ask An Assistant.
*in her Grandma's sewing room
- What Administrative Professionals Day is, where it gets its roots, and how it can help lead people to a bigger mindset shift
- Why you should learn your assistant's language of workplace appreciation
- How personality profiles (e.g. Myers-Briggs or Enneagram) can help you develop your relationship with your assistant and team
- How Jess and I developed an excellent working relationship over the years
- Gift-giving tips for acknowledging people (like assistants) who work with or for you
- What to do when your assistant's going through a rough patch or not showing up in the way they need to
- How Jess's role with SPI has evolved over the years
- Why thinking about your assistant as working “with you,” not “for you,” can make a big difference
SPI 473: Assistants, Admins, and Appreciation (with Jess, My Assistant of 7+ Years)
So you're hearing my voice right now on this podcast, but what we don't hear or what we don't see, or even consider is all the people who help get this particular show on the airwaves for you, and the feed that you're listening to. Now, for six whole years, when I started my business, that was indeed all me, like literally all the things, including show notes, the artwork for each episode, uploading the podcast. All those things was all me, but then I got smart finally, and I finally hired people. I started small, but I hired people to help me with the things that I knew I shouldn't do anymore, or the things that I just didn't even know how to do as I wanted to continue to grow my business so I could serve you more, and there's many people behind the scenes. We've met a lot of Team SPI over time here. You're going to meet even more of them over time.
If you're a member of SPI Pro, thank you very much by the way, you've gotten to know a lot of my team a lot more intimately, but there's one person on the team that I want to highlight today, because in fact, in two weeks from the date of this episode popping up is April 21st, 2021, and that is actually Administrative Professionals Day. It was once known as Secretaries Day or Receptionists Day, or what have you. It's sort of evolved over time, but I wanted to bring on a special guest today, my own Executive Assistant, Jess. Jess is somebody who many people in the audience has gotten to know very, very well, some directly via email, many, in fact, in person. When I go and fly out to events, sometimes Jess comes with me, and when we hold events in San Diego, Jess is very much a part of that process and very much involved in the interactions too, so we thought it would be a fun idea for Jess and I to have a discussion about, well, what is appreciation? What does that actually mean?
What does it actually look like? How do you show appreciation? What different ways are there to do this? We're also going to talk a little bit about conflict between assistants and their executives, and some other things that you can think about to make sure that you have a great relationship with this person who is likely there to help you do more of what you can do best, and that's why today's important. Let's play the intro music.
We're going to talk for just another minute, and we're going to get right into it and bring Jess on the show. Here we go. I'm so excited for this.
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 thinks his voiceover guy is incredible for continually providing voiceovers for SPI for over a decade now. Thanks, John! Oh, wait, that's me. Thank you, Pat! - Pat Flynn!
Hey, what's up, everybody? Pat Flynn here, and thank you for listening in on Session 473 of the Smart Passive Income Podcast. I got to say, I wouldn't be here today if it wasn't for my team, and especially Jess, and I'm excited to introduce her to you if you haven't listened to her before. She's been on the show a couple times before, in fact, the first time in episode 115, which was, I think just a couple months after I hired her for specifically email. In this episode, in addition to all the things I mentioned earlier, we are also going to talk about how an executive can do a lot more for you over time and all the kind of fun, quirky ways that she and I have learned to work with each other because that's how we've gotten to where we are, so here she is. This is Jess, my Executive Assistant. She's awesome. Here we go.
Hey, Jess, welcome back to the Smart Passive Income Podcast. How are you?
Hey, Pat. It's great to be here. I'm doing well. How are you?
Long time no chat, like yesterday, because you and I chat almost every day, and today, we're going to talk about, in fact ... The last time you were on the show, I think it was episode 409 or something like that, and we talked about how we work together, how we coordinate and choreograph our work, and the things we've learned over time. We've been together for seven plus years now, and it's been amazing, and you've done so much work. A lot of the audience knows who you are, has interacted with you, have seen you at events and whatnot. But today, we're talking about something special because this is about Administrative Professionals Day, but it's more than just the day, but this kind of topic - and actually Administrative Professionals Day is on April 21st this year, April 21st, 2021. Tell me about this day, Jess, and where this idea for this episode came from, and really, what our goal here is today.
Yeah, absolutely. Administrative Professionals Day is something that dates back to the 1950's, when it was originally Secretaries Day, so back when there would be inside of a company, that secretary, or receptionist, or some kind of administrative professional who kind of rules the roost or makes the office run like clockwork, and people only notice if something goes wrong because things are going so smoothly and so swimmingly the rest of the time, that it's just kind of smooth sailing for the person who is that front-facing receptionist, secretary, whatever the job title may have been.
Then, over the years, it's kind of evolved into Admin Day and Administrative Professionals Day, which is where it is now. It's just a day that is meant to recognize - and some companies do say Administrative Professionals Day or week, so you might do like a day thing once a year, or you might do kind of a week-long appreciation thing, depending on the size of your organization, depending on the number of administrative professionals that you might have on any given day. Yeah, generally speaking, just kind of something to recognize all of the invisible work that happens, because a lot of times administrative professionals are underappreciated, they're underpaid, they're not treated as great as they could be. So there is some division too about whether or not Administrative Professionals Day is a great thing to celebrate or not, but we can talk about that later.
Yeah, I mean, we're not here to tell you to, "Okay, now's the time to go do something for your assistant." Right? That's not the purpose of this. It's to have a discussion between myself and my executive assistant, Jess, who's again, been on the show before, but today specifically, just to kind of give you inspiration for how you might be able to think about who it is that you work with and how we can ensure that everybody's happy along the way, right? I think that a lot of people treat this day, if you will, just like sometimes Mother's Day or Father's Day. "Okay, I'll get you flowers. It's that one day of the year," and of course, we know it's much more than that. So maybe perhaps rewinding a little bit and talking about the relationship between a person and their assistant and how important that is, and how that needs to be a relationship that continues to thrive over time.
Yeah, definitely. I love it when people do want to recognize Administrative Professionals Day. I do think it does have a little bit of that, "Well, it's kind of a token. Here, we're going to do a little thing," but I do think it leads into a bigger mindset shift, especially for people in the entrepreneurial sphere, people who work in smaller, more agile organizations, or people who work in big organizations who are coming in and really trying to make change. I really think that there's a big opportunity for people to recognize their assistant as an extension of themself, no matter what level that they might be at, whether they're the CEO, whether they're the director of some department, whether they're a solopreneur.
Your assistant is an extension of you, and you as the person who has the assistant can't fire on all cylinders, unless you have a strong support person in your corner. So I think that there's a huge opportunity for folks to take the spirit of Administrative Professionals Day, and carry it with them throughout the course of the year.
I love that. What does that mean exactly? Does that just mean like, "Let's make sure to say thank you," or more tactically or specifically, what can an entrepreneur do to keep that spirit of that day sort of open throughout the year?
Yeah. I love that question. Something that I really see a lot is learning your assistant's love language. There's a really great resource online, if you just look up the love languages quiz, and you can get a feel for what your assistant's love language is, and then speak it throughout the course of the year. They do actually break it down, like you can do the love language, which is geared a little more toward personal relationships, and then there is like a languages of appreciation for the workplace.
I've taken both quizzes. They amount to about the same thing, but if you have your administrative people, and everybody in your company, honestly, but administrative people specifically, take the quiz and just have them share those results with you, and learn how to speak appreciation to them, so whether it is, "Hey, Jess, you did such a great job on that project. Thank you so much," or, "Hey, Jess, you did a really great job on that project. Here's a gift because I thought you did a great job and I really want to recognize it." There are opportunities to take that and just weave it in throughout the course of the year and not make it just a one day a year thing, just really bake it in throughout the course of the year.
Yeah. I mean, and this is really great, and of course, remember, we're not just talking about specifically administrative assistants and whatnot. It's anybody in your business that helps you or works with you in a way who perhaps sometimes we just forget that they deserve things, and yes, we should always have sort of that minimum grace to say thank you when something's going well and those kinds of things, but ... I'm curious, what would you say to the audience in terms of your love language or your appreciation language, and how do we work together, and how do I support you with those things specifically?
That is fantastic. I would love to talk about that. I really came from a long line of executive assistant roles where I was not appreciated at all, so coming into working with Pat was really fantastic. You're a big gratitude guy, gratitude to everything that goes on in your world, and you've really been an extension ... Like you've extended that to me in so many ways.
I think my biggest love language or language of appreciation in the workplace is words of affirmation, so just hearing that, "Hey, Jess, you did a really great job," no matter how big or how small something is, it really goes a long way and is very encouraging. Also, you give me a lot of autonomy in my role. You're not constantly micromanaging me. You're not saying, "Hey, why did you do this the way that you did it?" You just said, "Hey, you did that thing that I asked you to do, and you did it so efficiently, and you did a great job, and we got great feedback on it from the audience, and you made me happy by extension," and I love that.
That's great. How did I learn what those language of appreciation were? Of course, when you work with somebody new for the first time, obviously, you don't know what that is, so is it, "Hey, assistant, could you take this quiz for me?" Is that how it is, or how would you recommend people who have an assistant or thinking of hiring somebody in such a manner, how would they begin to learn that language?
Yeah. I think that doing that quiz or any number of personality profiles, like the Myers-Briggs, or 16 Personalities, the DiSC Profile, Strengths Finder, Enneagram — all of those are really great tools to have your staff do just at the beginning, because like you said, it's an unknown relationship, it's new, you have to learn it as you go, and I think having those tools in your arsenal, they're not absolutes. It's not okay you are a type ... I think I'm a Type 8. I'd have to look at my Enneagram. I don't remember.
In the Enneagram?
Yeah, you're an 8.
I'm an 8.
I know. I know you.
I'm a Type 8, as Pat remembers, and I need to look up and learn more about the Enneagram, but having those tools in your repertoire can just really give you a great basis for having those conversations and saying, "Okay. Based on the fact that you're a Type 8 and ..." You, Pat, are you a 2? Is that right?
I'm a 3.
You're a 3.
A hardcore 3.
Hardcore 3, okay. Like what are ways that 8's and 3's tend to work together? Again, those aren't absolutes, but it gives you a great framework to start from and just really learn about each other and go into the conversation knowing each other's strengths and weaknesses, go into the conversation knowing about conversation styles and what will work and what won't work. Yeah, and then just really, it's time. Like Pat and I mentioned, we've been working together for seven plus years, and you do things, you work together, you work on projects, and you learn. You make mistakes, and you own up to those mistakes, and then you don't make them anymore. Again, I think I just really lucked out because Pat is so vocal with his gratitude, that it just really ...
It just kind of ... Yeah, it just matched and was really effortless.
I think you've done a good job because I didn't really take a test to tell you anything, but you have purposefully sort of found out what gets me fired up, and also what brings me down. You know that about me now. For example, one thing that I really struggle with is negative criticism. That stems from my childhood, and it's hard for me to continue to wear that thick skin sometimes, especially when it feels so personal. So oftentimes, you will shield me from a lot of that stuff, and I appreciate that a ton, and you'll obviously let me know when anything's like to a point where I need to know those things, but a lot of times, you do shield me from a lot of that stuff, and the bigger you get, the more audience that you have, the more likely you are to attract those kinds of things, so you've learned that about me.
You've also learned that as a 3 - and this wasn't even like, "Oh, you're a 3. Okay, I'll do this." It's just you've learned this about me over time, and the three sort of tests, and the Enneagram test, and the love language stuff, like that sort of confirms all the stuff that you've learned about me. But as a 3, you know that I thrive off of recognition. The fact that when I see that I'm actually helping somebody, when I see results from the work that I'm doing, that fires me up. That gets me excited. That is my reward. And so you actually had this idea once to create a Slack channel literally for any time somebody mentions something like a article or has good feedback or whatnot, you just pop it in there. I go in there once a week just to kind of remind myself about, "Wow, there's really good things happening here. Okay, I'll keep going," and if I get down, that's kind of like one of several places where I have a lot of that positive feedback from my audience coming in from not just Instagram and Twitter, I have a wall here in my office with thank you notes and whatnot and such that also inspire me and keep me moving forward.
But that was stuff that you learned about me over time, right? What perhaps could you share to perhaps those entrepreneurs who shared this episode with their assistants to learn more? What advice would you give to those assistants who are listening to this right now to, on their end, have a better relationship with the person who hired them?
Yeah, I would say to those assistants, really just lean into your skills because a lot of assistants are very ... We notice everything. We're very perceptive. We pick up on trends, so like you and I had a recent, just this last week, I think, we had a couple of interviews and you said, "Hey Jess, could you remind me this person? What was the connection there, or a little bit of context for the conversation that I'm going to have?," and so I said, "Well, how about ..."
"I'm always happy to bring that information to you, but I also don't want to be unavailable when you need it. So how about, would it be helpful if I added some notes to the calendar appointment and said, "Here's where you get that information, and then you just know that there's always one place to go." So notice trends. Pick up on them. Improve and evaluate. I guess, evaluate first, and then improve as you can, and on the flip side of that, to the entrepreneurs who have the assistants, be open to that. You've hired an assistant because you have some areas that you're not quite as skilled at, like there's a lot of things that you can do.
You can book your own flights, you can make your own car and hotel reservations, you can manage your own calendar, you can answer emails, but is that the best use of your time? Probably not, so you hire somebody like me. You hire your assistant to help you be the best version of yourself so you can focus on your zone of genius and get out there and just really be open. When your assistant is coming to you with ideas, and thoughts, and process improvement, be open to that and just say, "Wow, my assistant is always ... She or he, he or she, always has my back, always looking out for me, always evaluating and improving, and this is awesome."
Yeah. That's perfect. Thank you so much for that. By the way, we've noticed over time that many others have really enjoyed conversations between you and I and others about the assistant life, and sort of what it's like to work for somebody else. You also have gone so far as to actually create a podcast, in fact, to help people even more who want to learn more about this or to specifically help assistants.
Can you talk more about this podcast? Where can people check it out? What's the name of it, et cetera?
Yeah, absolutely. I've been on the show here on SPI and AskPat even once a handful of times, and I've always been very shy to talk about this, so thank you for prompting me and not letting me shy out of it this time, because the last time, I was just like, "Oh, he didn't ask where people can find me, this is great." People can find me - the podcast is called Ask An Assistant, and it's just ... I've been an Executive Assistant for 17 or 18 years now, and I'm at the start of year eight with Pat, so you're coming up on more than half of my career here, but just, I've learned a lot along the way, I've seen technology develop, and especially over this past year, things have just ... Obviously, when everybody went remote, you and I had already been working remote for six plus years, so that part wasn't a huge transition, but just being available to provide advice and answers to folks.
I just, I have a big, random, broad wealth of knowledge and I'm here to share it, and people have questions, I have answers that I hope will help, and Ask An Assistant, that's how it was born, so AskanAssistant.com. I would love it if you checked out the show, rate, subscribe, do all the things, but ask me a question. I would love it. Just AskanAssistant.com, and you can ... There's a little place for you to record your question or type it if you're not feeling up to recording or if you want to be anonymous, and I'm here to help, so that's me.
That's so cool. That's so cool, and I'm reminded of when the first time you came on the show, episode 115, after I hired you to help me with my email list and I had to declare email bankruptcy and then start over, and we worked through that. If you want to go back in time and listen to Jess way years back, you totally can. Sorry, Jess, I'm throwing you under the bus here, but if you want to hear just what happens when you just continue to work through, and then you get inspired ... I mean, your voice by the way sounds amazing right now. You're using this new equipment, you're rocking it. Well done, so Ask An Assistant, check it out on the place that you're listening to the podcast right now.
Okay. I want to talk about gifts. A lot of people struggle with gift-giving. A lot of people, comes natural, but if somebody were to, somebody like myself, for example, who has hired you, what is a gift that you appreciate? Does it have to be expensive? I know the answer is no, but give us some parameters, if you will, in terms of best gift-giving tips for those who want to reward and sort of acknowledge those who are working with them.
Yeah, absolutely. As much as I say that I do love words of affirmation, everybody loves getting a gift. A big part of that though, is that a lot of people hire an assistant to help out with things like gift-giving, so I - one of my favorite ways that I've ever been celebrated is I had this role where my executive, once a week we would get together and say, "Okay, here's your upcoming birthdays, weddings, celebrations. Here are the people who need a gift from you. Tell me what your budget is, and I'll take it from there." And so I would always say, "Oh, by the way, your assistant's birthday is coming up," or, "It's Administrative Professionals Day in four weeks."
"What is your budget?," and they would tell me, "Here's my budget for that," and then I would buy my own gift, wrap it, like wrap it, have it delivered to the office, wrap it, give it to my executive, they would hang onto it, so it would sit on their desk for two weeks.
That's so funny.
Then, on the day, they would come in either early that morning or the night before, and it would be sitting, perfectly wrapped on my desk. That to me was just so cool, because then ... You and I have talked about this over the years. I have cats at home - flowers aren't super practical. I'm lactose intolerant. There's so many beautiful, beautiful candies out there, not a lot of them are things that I can eat, and then my husband ends up getting them, and it's not husband appreciation day, it's Jess appreciation day.
So being able to take whatever the budget is, whether it's $10 or hundreds or thousands of dollars, you decide what your budget is, what makes sense to you, what feels good to you. I don't view it as like, what is the Michael Scott thing with the Christmas? It's you tell somebody I love you this many dollars. I don't view it like that. I view it more like it's thoughtful, it's personal. So really, just take the time when you're doing the gift. My accountant actually was really fantastic at this. She continues to be fantastic at this. When I was doing intake with her as a client, she asked a couple of just kind of innocuous questions. I don't even remember answering them, but suddenly, for my birthday and for Christmas, these beautiful gifts showed up at my home. She sent me these raw vegan chocolates for one of the holidays, and I don't remember what the other item was off the top of my head, but just kind of with the intake paperwork, just asked a couple little like, "Do you have any allergies? What are your favorite candies? What are ..." Kind of going along with the Enneagram, whatever kind of little intake quizzes that you might take with somebody, straight up just ask them. Especially if you're starting a new relationship and you just kind of bake it into your intake new hire paperwork, the person won't even remember that you asked that, and then they will be totally blown away when they get a gift card to their favorite place.
I will say with gifts, there's ... I know sometimes in bigger organizations, it's harder to personalize, it's easier to just kind of generalize, but there are certain things like if you were going to do a gift card for everybody in your organization, and you just do an Apple gift card for everybody, what's the percentage of people that have Android phones that aren't going to be able to use the Apple gift card? Even if you just ask something like, "Are you Apple or Android?Do you like Target or do you like ..." whatever the Target equivalent is. I'm not sure what other stores then Target, but just ask for a handful of places. "Where's a place that you would love a gift card to? Where's a place that you would use a gift card for?," so just kind of getting some of that -
Yeah, a little bit of stealth. Get that information when they're kind of inundated with information requests already and just go from there, and you'll look like a total hero.
What are your thoughts on if I were to like ... Again, what we're talking about works for us, and this is what we're discussing here. You can figure out what works for you too, but these are just kind of inspirations and ideas, but what are your thoughts on a executive, for example, who goes into social media, discovers their assistant's profile, scours around, maybe scrolls 50 items down in their Instagram, finds a thing, gives them the gift, they did the research. Is that cool? "Thank you for doing research and seeing that I love little Pokemon collectibles," that's, thank you. Or is it, "Oh my gosh, my boss went into my social sphere, scrolled all the way down, so all my pictures and picked the one that they thought ..."
That's creepy. Where do you draw the line with that?
I think for me personally, that's how I do a lot of - because you've had me do gifts for folks over the years, and that's how I've done a lot of my research. Like when I'm gifting for somebody that I don't know, I've gone and dug and found some really thoughtful gifts. "Oh, this person has a dog," and then a couple of posts back, they posted about their favorite toys or their favorite treats. It's very easy then to say, "Oh, well, Pat has a dog, and his dog's favorite treats are XYZ."
Once you get to a certain level or age or whatever, it becomes harder and harder to gift people, because depending on where you're at, I think a lot of people, when you need or want something, you either save up for it and buy it yourself - so like if you're kind of a specialty hobby person, you know what pieces you need and don't need. Or if you have a thing that you need or want, you just kind of go out and get it. I think something like that, that to me is a very innocuous way to do some research, and that's the way that I do a lot of my gifting research personally.
Yeah. That makes sense. If everything out there is in the public anyway, you shouldn't be bothered by somebody actually going and doing that, or else you should just hide it if that's kind of weird to have somebody do that, right?
Yeah, and I would say too, that if somebody's, like if their profile is listed as private, if you were to go and say, "Oh, hey, I see that so and so follows them," and then ask them to do it, that's where it might get a little creepy. But that's something that you definitely could ask again, kind of an intake like, "How do you feel about social media? Are you okay doing that? What are your profiles?" And then people can kind of either share or decline to share as it feels comfortable for them.
Cool. Thank you. What are some quick, easy ways to help perhaps an assistant who might be going through a tough time? Sometimes we have bad days. Everybody has bad days. And perhaps the executive out there is noticing that their assistant's kind of going through some tough times and struggles. How might one best help and serve that person?
I think when you're ... Because when you do have an assistant - executive assistant, administrative assistant, otherwise whatever job title they might fall under, just noticing that somebody is having a tough time and make the first move and say, "Hey, I noticed that you've been maybe a little bit down ..." You don't even have to say, "I've noticed XYZ change about you," because maybe the person doesn't even realize that they are exhibiting that, like front-facing wise. But just kind of taking a moment to say, "Hey, I really care about you. I care about you as part of this company. You're very important. If there's ever anything that you need to talk about, my door is open. This has been a really stressful and strange year. If you need ... Here's a comp day. Just no questions asked, take a day off, take some time for yourself," and just kind of in a very open but compassionate and caring kind of way, because whatever the person might be going through, they may or may not want to share any of those details with you.
But just really making it clear that you're there for them, you support them, that can really make all the difference, and just making resources available. If you say, "Hey, is there something that I can help you with? Would dinner delivered to your house so you don't have to cook tonight help, or would lunch, just for you, make you feel special and appreciated?" Just kind of throwing a couple of ideas out there, but really just putting it in that person's court to say, "Hey, I'm here for you, whatever you might need."
Cool. Thank you for that. I want to share a scenario that actually happened in real life to somebody. I'm not going to mention any names or anything, but this is a real-life scenario and situation between an assistant and an executive.
This person who is an executive or an entrepreneur had been working with this assistant for three, four years. Amazing relationship, they kind of built the company together side by side, and then this person's assistant, their lives changed. Something in their life happened, such that they just weren't as reliable anymore. They weren't showing up, they weren't reporting like they were supposed to, dropping the ball, if you will, and of course, you're weighing this relationship that you built together over time with the reality of the situation being that things are not great right now business-wise because you're dropping the ball. How would you recommend an executive approach the assistant in a way that's not confrontational, not in a way that would kind of get this person to either just blow up - or how would you best recommend an executive approach a situation like that?
Yeah, that's a great question and a tough, sticky situation that I have definitely heard. I don't think this is the same person that we're talking about, but I -
It's common thing. I mean, it happens.
It's very common. Very common. I think it kind of ... We touched on some things, even just in the last little question that you had, about try to be as open and understanding and nonjudgmental as you can. Use a lot of I language instead of you language. So instead of saying, "You've been dropping the ball," "You seem tired," "You seem cranky," "You seem whatever it is," keep it about you, the executive. Say, "I'm struggling right now. I'm noticing that things are falling through the cracks. What can I do to support you? Whatever might be happening, how can I support you? Or, again, are there resources that I could provide for you if we're ..."
gain, not naming names, but this is a situation that I encountered once. A fellow administrative professional started dropping the ball, started slipping, and it turned out that they were struggling with substance abuse. We found evidence of the substance abuse in their trash can at work. That's how bad it had gotten, but just pulling them aside, getting your best ...
Pull in a professional. I'm pretty sure we ended up having a substance abuse person come in to have that conversation with us, and we ended up - the company ended up sponsoring this employee through their treatment and road to recovery. So definitely provide resources as you can because a lot of times, if people are struggling, they might not have resources outside of work, they might not even know that they're struggling that bad, and you as the employer might not be equipped to handle whatever it is that's going on, so bring in professionals as you can. Bring in like a mental health worker or anything like that to support the work that you're doing with them.
Sometimes that definitely can help. I think providing resources is an amazing strategy in a way to hopefully help alleviate the situation and get everybody on the same page. A lot of times it's just miscommunication sometimes and different expectations on both sides, and kind of, like you said, setting some time to kind of get on the same page together can be really great.
Then, other times, person, one person or the other or both end up changing to a point where it's, probably doesn't make sense to still be working together, and that is a reality as well. And in the case of the person who I'm speaking of, it had to come to that unfortunately, but it wasn't without research, it wasn't without second, third, fourth chances, but of course, the business has to do what the business needs to do sometimes, so ...
Right. Yeah, and I mean, there are even smaller things, like not every situation is going to be quite as extreme as the one that I described. But there are definitely resources for an evaluation like, "Hey, here's the original job description that we hired you to do. Currently, these things aren't being met. What resources, training can we provide? What support can we provide?" And if it's just not a good fit anymore, that's okay too.
Like, "No harm, no foul, but just it's not a good fit for us to continue working together, but we can support you in your search for something different, but our company currently needs something different too."
Yeah. That's great. I love the way you phrased that.
To finish off here, because that was a little bit more on the negative side of things, I want to think about things positively as well. I want to offer the example of you, Jess, as your employer. I hired you for a very specific reason in certain tasks in the beginning, back in episode 115 for email and a few other sort of super-administrative sort of things, but your role has changed over time, and I want to know from your perspective, what that's been like to have your role change. How has it changed for people in case they don't know, and how was that welcomed?
Yeah. Definitely. Pat and I originally got connected, again, 115, SPI 115. I was brought into tame Pat's inbox, and so we went from 9,000 unread emails to inbox zero. We hit inbox zero, I would say like 70 percent p of the week.
Sometimes there's a few little straggler messages that still hang on there, but we try to keep that up as much as possible, and so it went from a one-off project to, "Well, hey, now you tamed the inbox, but how do I maintain it from here, so could I keep you on to maintain that?" Then, as time went by, the team would say, "Hey, we don't have the bandwidth for this piece of the process anymore, but we don't want to hire a whole new person to do this one small thing. Jess, could you expand your bandwidth a little bit?" I have been so fortunate over the time since 2014 with the team. I've touched on everything that we've done. When you and I started working together, the only thing that you sold was a 99 cent ebook on Amazon, and we gave away more copies of that than we sold.
It was a lot of the email communication, but then it branched out into supporting the AskPat Podcast in a small way. I've been scheduling all of the guests for Smart Passive Income and AskPat for several years now, supporting your speaking career, Pat, so all of your travel, all of your logistics, running events, so a big part of FlynnCon and any kind of meet-ups that we've done in San Diego or around the country, and it's just, it's been wonderful. It's been so great to have the opportunity to branch out and say, "Hey, this is something that I can do, or this is something that I can definitely learn how to do." And just having your confidence in me to say, "Hey, Jess, yeah. You've proven yourself over the last one year, two year, five years, seven years to be reliable, and I know that if I give you the reins on this project, that you'll do a great job. And whatever resources that you need, you will get them or ask me for them, and will make it happen." It's just been wonderful and just all of the autonomy and the flexibility to do what I think is right, the way that I think is right is priceless.
Yeah. No, and thank you for that. It's definitely been a journey for sure, but it's been cool to see the sort of up-leveling of just kind of like what we're doing together, and it's more than just email now, of course. I think that this is a very common thing because when you find somebody that's great, of course, you want to allow them to grow their career as well, so I'm sure that you didn't ... In fact, there was a time where you were like, "I think I've outgrown the email now," because you are still in the email, but not to the extent that you were in before.
There's even other people on the team now who handle a lot of that stuff, and thank you to them as well, but you were going to grow into the sort of manager/director sort of specialist with regards to the events that we were going to put on, from FlynnCon to other things, and of course, then the pandemic happened and COVID, and so we aren't holding in-person events. But you had started to do a lot of that stuff, not just with FlynnCon. In FlynnCon, interestingly enough, your big role is to just make sure my family was taken care of, and that was huge for me, and I want to thank you for that.
But you were going to also manage a lot of the more intimate sort of workshops that we did in person in San Diego, which you've done and a few of the more intimate situations, which we always had a blast doing.
We always had a blast doing that. It's been so fun, and I can't wait until we can get back to doing that again at some point, but for now, just hopefully this episode inspires you to consider how important an assistant is, how they are, like you said, Jess, an extension of who you are and that you are unable to do your best work without them. I find that to be very, very true, and I can't thank you enough here publicly, Jess, for everything that you've done and continue to do for me. I want to say that - and I'll have you finish off this episode with inspiration for the employer or for the executive to, just as a nod to yes, Administrative Professionals Day, but this is the full year. This is not just like your assistant, but assistants all across the board.
Anybody with assistant in the title deserves something like this. Do you want to speak to that, and also maybe let's just finish off with what we can have people think about coming out of this episode?
Yeah, definitely. Just really take it ... Don't make it a one-day thing. Make it something that lasts all year long, and take care of your people, and just really show them that they're appreciated. Show them that they work with you and not for you.
I think that that mindset shift, both for the employer and the employee can be really huge. Some people really thrive with a lot of structure, with a lot of deadlines. Some people like myself thrive with autonomy, and flexibility, and freedom, and just try to learn each person in your organization as best you can. And whether that's you as the CEO or maybe a company culture, position or something like that, just really make it a priority in your organization because showing people that they are appreciated and a valued part of your organization through your words, through your actions, through gifts, through good pay, through bonuses, it does nothing but breed loyalty and love for the company and love for the people and other organizations that you support, and it's so important. If there's anything that Pat or I can do to help you make that a reality, just feel free to reach out. We're here to help.
Yeah, and again, don't forget, AskanAssistant.com for the podcast. And feel free to share this with your administrative team as well, or anybody else. I think this is an important episode for sure that hopefully you get some good vibes out of this, and thank you, Jess. We appreciate you. Looking forward to connecting with you again publicly here, because I know we always do it privately, but this has been a lot of fun. Thank you.
Make sure to stick around because you're going to hear in the backstage pass, in fact, if you do have access to that, our sort of premium feed that is ad-free, but also gives us a little bonus time with our guests, you can check that out if you'd like. We'll have more information about that in the show notes if you haven't gotten access to that already. And be sure to check me out on the follow-up Friday episode here on the public feed, where I'm going to go deeper with just me about the relationship that I have with Jess and some of the things that I'm thinking about doing in the future, and how we're all sort of, kind of in this together. So thank you, Jess. Thank you to everybody, and yeah, some final words coming soon.
Yeah, all right. I hope you enjoyed that episode with Jess. Isn't she amazing? She's so great. Jess, thank you so much. I know you're probably not going to listen to this, but you also have a podcast to take care of now too, which is super cool. I'm so proud of you.
AskanAssistant.com if you have a question for Jess that you'd like to get answered on her show, check out AskanAssistant.com. Of course, make sure you subscribe to this show too, and if you ever send an email to us and especially with relation to any events or other things in the future like that, you'll probably hear from Jess in the future, and I look forward to potentially having us all together maybe at another FlynnCon or another event down the road, so - wooh! All right. That was super fun.
I'm sure you're going to hear from Jess later in the future, as well as several other team members of Team SPI here on the show too. If you'd like to get the show notes for this episode, all you have to do is go to SmartPassiveIncome.com/session473. One more time, SmartPassiveIncome.com/session473. Thank you so much for listening in. I appreciate you. Hit that subscribe button if you haven't already, and as always, cheers, peace out, and Team Flynn for the win.
Thanks for listening to the Smart Passive Income Podcast at SmartPassiveIncome.com. I'm your host, Pat Flynn. Sound design and editing by Paul Grigoras. Our Senior Producer is Sara Jane Hess, our Series Producer is David Grabowski, and our Executive Producer is Matt Gartland. The Smart Passive Income Podcast is a production of SPI Media. We'll catch you in the next session.
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