Music by Breakmaster Cylinder | Sound Design by Cashflow Podcasting
Jess Lindgren shares what it takes to build a working relationship that helps give you back your time and focus.
You’ll Learn
- The must-have traits of any great assistant
- The key to hiring an assistant
- Where to find great assistants hiding in your own network
About Jess
Jess Lindgren has worked in the C-Suite of small companies for 20+ years, and developed a diverse skill set by wearing many hats on any given day. She focuses on supporting her current CEO in his many endeavors, works to improve the effectiveness and efficiency of EAs around the world, and has very low tolerance for any meeting that could have been an email. Jess hosts the wildly popular* business podcast, Ask An Assistant. (*in her Grandpa’s woodshop)
She loves living in Syracuse with her husband and three cats in their century home. An avid fan of putting pen to paper, Jess personally replies to every handwritten letter she receives.
- Podcast: Ask An Assistant
- Website: JessLindgren.com
Resources Mentioned
- Book: The Hitchhiker’s Guide to the Galaxy by Douglas Adams
- Service: Fancy Hands
- Service: Care.com
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Jess Lindgren Transcript
Pete Mockaitis
Jess, welcome!
Jess Lindgren
Pete, thank you so much for having me.
Pete Mockaitis
Well, I’m so excited to get into your wisdom. We are talking about assistance, assisting. Whether you are the assistant or the assisted, I think we’ll have a lot of valuable wisdom to unfold here. And I want to, first, hear, in the assisting game, what is something that has been a surprising learning you’ve picked up that is just transformational, that makes for assistance working great versus not so great?
Jess Lindgren
I think the biggest thing is that people don’t think about this. People don’t think about this more now than they did. I have been an administrative professional, an executive assistant, for over 20 years now, and, things have definitely changed in that time. And people used to be way more focused. And this is general, because people still are focused a lot on hard skills over soft skills.
But people used to get really hung up on, “Oh, well, if you can’t type 90 words per minute,” “If you can’t pass this super nuanced clunky test on Outlook from 1998,” and a lot of those tests are very, like, you can’t do anything with shortcuts. You have to know exactly where to find stuff or you get knocked down on it. Nobody used to care if you were a good fit with your executive.
Like, people would look for executive assistants who were exactly like them, which is kind of the opposite of what you want. Like, you really want somebody that, if this is you, you want an executive assistant who’s going to come in and fill all those gaps for you, right? So, people really never used to focus on soft skills, emotional intelligence, that kind of thing.
And it’s always been something that’s bothered me in my earlier roles that we weren’t a good fit. We didn’t mesh well together. We were a little too similar and kind of butt heads quite a bit. So, that’s really something that I felt from an early time in my career, and have been very fortunate for the last 12 years to be working with somebody who appreciates a good working relationship in terms of emotional intelligence, in terms of soft skills, in terms of fitting better together.
And I do feel like industries as a whole, especially in the entrepreneurial sphere where we find ourselves, people are finding that that’s a much more valuable thing when they look for someone to hire to be their righthand gal or righthand guy.
Pete Mockaitis
Yeah, that makes total sense to me. And to that point about opposites, or filling in gaps, I think that’s fantastic because we humans have this natural affinity for folks who are similar to us and see the world in similar ways to us, and it feels so good. For example, I’m big on ideas, creativity, ideation. That’s really fun for me. And so, if I talk to someone else who’s the same way, it’s very exciting.
Jess Lindgren
Oh, for sure.
Pete Mockaitis
And we’re just like firing out ideas all over the place. And yet, if we wanted to accomplish something, we’re not a great duo.
Jess Lindgren
You need somebody behind the scenes, like kind of pulling you back down to the earth. Like, you’re up there, you’re just floating away with all of these ideas and stuff. And that’s not to say that I don’t have creativity and ideas of my own. They’re just different. So that’s something that’s really, really nice, is to have those, you know, respect for what the person does that I work with for sure.
So, yeah, that creative conversation, like it’s very fun and very important, but it is also good to have somebody, you know, like I said, like you said, filling in those gaps, pulling you back down to the earth and being able to get you on task, like, “Okay, it’s great that we’ve got these ideas, but has anybody written anything down? Have we put anything into the project pipeline? Are we making progress forward?”
And just someone to kind of, “Okay, there’s 20 minutes left of this hour meeting. We need to actually make some progress here.” So, it’s really great to have that give and take, and have somebody who really just kind of fills in your other half. You need that right brain to the left brain, the type A to the type B.
Pete Mockaitis
Okay. Well, could you, perhaps, give us a story, illustration, demonstration, example to make it really clear for what does outstanding assistance look like versus what okay assistance looks like?
Jess Lindgren
Okay. Yeah, something that really comes to mind for me is that there are a handful of careers in this world that people think just anyone can plop in and do it. People think that they can do real estate. People think that they can do retail. People think that they can do administrative work. And that’s just not true.
Like, I personally, I cannot go. I worked one. I didn’t even complete the four-hour shift at Victoria’s Secret in college because it didn’t work for me. Like, everything that they were training me to do, I was like, “Nope, this is not for me.” Real estate, you have to have, like, the back of your hand, you have to know, you have to have relationships all over town. I couldn’t do that. I don’t have that breadth and depth of knowledge and relationship the way that really successful real estate agents do.
When it comes to administrative work, it’s a lot of creative thinking. It’s a lot of connecting the dots. It’s a lot of thinking ahead. It’s just skills that not everyone has. So, the okay assistance is the person who says, “Oh, yeah. Well, you know, I’ve been working in sales for like 20 years, and I think I want to pivot and just do administrative work. Like, anybody can do that, right?” Like, people who are just sitting there, trying to bridge a gap.
And, like, I’ve been there. I’ve tried to, I’ve had times in my life where I need to bridge a gap from job to job where you just take whatever is available. But people think that it’s just a job that anybody can do, and that’s just not true. I think you do have to have interest in it. I think that you have to have really sharp critical thinking skills. And I think that you have to really be a helper. Like, you really have to be someone who wants to help, not just someone who wants to come in, cash a paycheck, kind of half-ass it?
Pete Mockaitis
Yeah, understood.
Jess Lindgren
Yeah, like you really have to have some grit behind you. You have to really be into it, especially to be a career administrative professional.
Pete Mockaitis
That’s good. So, let’s hear the rundown there. Grit, creativity, interest. What are the other critical components, both in terms of if you’re thinking about a career in assisting, or if you’re thinking, “I need to hire somebody,” what are the top things to be looking out for?
Jess Lindgren
Like I touched on earlier, you’re looking for emotional intelligence, really, because a lot of it is, especially in an executive and/or personal assistant with your executive relationship, there’s a lot of access. You’re in a lot of rooms where a lot of other people aren’t, you know? My last in-office job, I would sit in on weekly board meetings.
I would sit in on meetings with the executives’ direct reports, like they’re director-level people, they’re manager-level people. And you have a lot of access to a lot of information. So, like, you’re looking for confidentiality, discretion. You’re looking for people who just care. You’re looking for people who care. That’s really important.
Pete Mockaitis
Yeah, I’ve heard that’s probably the top theme when people ask me, “So, Pete, how do I be awesome at my job, Pete?”
Jess Lindgren
You care.
Pete Mockaitis
“You’ve done a thousand interviews.” Like, that’s kind of the thing is to care, fundamentally, about the work, about your customers, clients, your colleagues, the product or service you’re delivering. Like, to the extent to which you give a hoot, to the extent to which you get cool creative ideas, to the extent to which you go the extra mile, you try something different, you’re proactive, you’re into it, you’re engaged, versus kind of just chugging along isn’t great for anybody.
Jess Lindgren
Right. And there’s finitely, I’ve had days like that. I’ve had weeks like that. I’ve had months like that, where you are just kind of not engaged or you’re feeling burnt out or whatever. But, like, in the long run, you really do need that interest, that drive, that passion.
And when you are in an entrepreneurial sphere, you need to surround yourself with people who, I mean, A, you need to know what your mission is. Like, you need to know who it is that you’re serving. You need to know why you’re serving them. And you need to be able to articulate that to people when you hire them to work with you, and have it be a very intriguing mission that it is that you’re trying to fulfill.
Pete Mockaitis
And when you say be a helper, tell us about that, because in some ways, every job is being a helper, but I think you mean something specific.
Jess Lindgren
Yeah, I mean, even using a salesperson as an example. They’re trying to sell software to a company, or whatever the product might be. So, we’ll just say that this is a software company. They’re trying to help a company make a decision between five different software that are out there that all kind of do the same thing.
But that is still, at the end of the day, kind of a self-serving help. They’re trying to make a commission. They’re trying to make a sale. They’re trying to be number one on the leaderboard. They’re trying to get a bonus at the end of the year, whatever it is. But when it comes to being an executive assistant, being a helper is just so important because, a lot of times, you are the person who is picking up a lot of pieces.
You’re filling in a lot of cracks, and you also have very high standards when it comes to your work. You care about yourself doing a great job. You care about the company succeeding. You care about the executive that you’re supporting being successful. And, yeah, just every successful executive or administrative assistant that I’ve ever met just, like, really cares a lot.
You care about the office looking nice. You care about putting a good presentation, a representation of your company. You care about putting yourself out into the world. You care about, honestly, really great administrative professionals care about doing impactful work. They really do.
Pete Mockaitis
Yes, I hear you. And the salesperson, not that those motivations are evil, and, in fact, they’re sometimes extremely helpful. It’s like, “Ooh, this guy is on fire to make it rain. And thank goodness they do.”
Jess Lindgren
Yes. That’s great. Good for them.
Pete Mockaitis
Everyone is able to have paychecks from that revenue generated.
Jess Lindgren
Exactly.
Pete Mockaitis
And that variety of motivation and hustle works there, but it’s a very different flavor of motivation and drive than that which is a great fuel for a successful assistant.
Jess Lindgren
Yes.
Pete Mockaitis
Okay, I’m grooving with it. So, then I’m curious, if one is doing a recruiting process, maybe engaging in some interviews to assess some potential candidates, what are some top approaches for interviews or selection or recruiting that could help us find, indeed, these helpers who really care?
Jess Lindgren
Yes. Okay. So, I have really strong opinions about this, and I’m really glad that you asked. Right now, for anyone who’s out there paying attention, hiring processes are completely out of control. The number of people that I have spoken with who just, “I went through three, four, five, six interviews,” you know, they’re like, “Okay, you’re our top two candidate.”
And then they get ghosted, or then they get like, you know, “Oh, well, we almost picked you,” or, like, someone will come back, you know, three months later, “Well, we picked the other person and they didn’t work out. Are you still interested?” You need to slim down your hiring process. This is not respectful of the candidate’s time. This is not respectful of your time.
What are you doing if you are putting someone else through six rounds of interviews? Like, what is everyone else on your team doing? Your salesperson is not out in the field making sales because they’re sitting there interviewing a candidate. They’re part of the fifth round of the interview and you’ve got 30 candidates, and you’re going to make that salesperson.
Like, the number of people that I’ve spoken with, who are executive assistants, who are looking for work, and they’re just like, “Yeah, I had to meet with the recruiter first, and then I met with the outgoing assistant, and then I met with the sales team, then I met with the marketing team. Like, these are people I’m not even going to work with. Like, why are they putting the whole company through this?”
And if you’re doing this with dozens of candidates every time, that is such a poor use of everyone’s time. And every person right now, they have to take work off. They have to stay late at work because they took a long lunch break to come to your sixth interview, the seventh or eighth or ninth or 10th interview. Like, you need to slim it down. Honestly, every time that I’ve hired someone, I can tell from the time I shake their hand if I like them and feel like it would be a good working relationship or not.
Like, slim it down, make it shorter. You don’t have to purely go on vibes, but, like, hire, what is it that I like to say? Hire slowly, fire quickly.
Pete Mockaitis
It makes sense to me in terms of like, let’s be very thoughtful about who we take on. And if it’s not working out, don’t drag it out for three years.
Jess Lindgren
Exactly. Don’t drag it out. Don’t drag it out for three years. But also, like on the flip side of that so like, what I mean by hire slowly is, like, get somebody in the door, but there is going to be like a ramp-up process, especially when you’re dealing with executive assistants. Like I touched on earlier, you have a lot of access as an executive assistant.
In terms of the hire slowly, fire quickly, I like to say to people, “Give your new assistant the garage code. Don’t necessarily give them the keys to the whole castle.” Like, you can give them some information. You can make the training process, make the onboarding process kind of slow, methodical, thought out.
But make the hiring process itself, like have a clear job description, but know that there’s a lot of room for nuance, that things are always going to shift, especially with an executive administrative or personal assistant. There’s always going to be things that you didn’t think of, that you didn’t know you needed help with, that you didn’t know they could do, that you could hand off to them.
Like, just know that it’s a living document, that it’s something that you’re going to need to update as time goes on. But really, strip that hiring process down. It’s not a good use of anybody’s time. Make a decision, roll with it. But that’s what probationary periods are for. That’s what that onboarding time is for, is to get to know them, see if it’s a good fit.
I’ve certainly had people who came very highly recommended, who interviewed very well, and then performed very poorly. And that’s where the hire slowly, fire quickly comes in. Like, I hadn’t bought them a new computer. I hadn’t bought them a ton of software. I hadn’t given them access to everything, but, like, I did make a decision, hire them, bring them on. And then I’m just like, “Well, this isn’t working out. Sorry.”
Pete Mockaitis
Understood. Okay. So, you’re saying, let’s not do nine interviews, but rather, let’s give someone a shot, do the probationary period, and then that goes well, we really say, “Okay, here’s more access, here’s more things.”
Jess Lindgren
Yes.
Pete Mockaitis
What are some key things that might show up as indicators that, “Ooh, this person seems special out of the pack, and, thus, it likely warrants to advance to the probationary period”?
Jess Lindgren
Yes. I mean, I think a lot of it is just looking for that caring, looking for them filling in gaps, looking for them noticing things when they say, “Hey, Pete, we’ve been working together for a couple of weeks here. I’ve noticed that you have X, Y, Z thing. Have you ever thought about doing it this other way?”
So, looking for people who really care about not necessarily that everything needs to get totally optimized and automated, but, like, sometimes things are too close. Like, you’re too close to things to even notice that there’s an issue, and you just do things that way because that’s how they’ve always been done.
And then when someone brings their specific experience, their specific expertise to the table, listen when they have ideas, implement what makes sense, but really look for them caring. They want you to have more time.
If you’re the salesperson of the company, they want you to have two extra hours in your day to be focusing on your job because you’re doing something inefficiently, or maybe doing something that’s not impactful, something that doesn’t even really need to be done anymore, something that’s outdated. Look for them making suggestions that make everyone do a better job. Like, that’s really important.
Pete Mockaitis
And so then, back into the interview, of which there might just be one or two and not nine, there might be some questions along those lines, like, “Tell me about a time that you noticed an opportunity for improvement, and what you noticed, and how you communicated it, and what happened.” And so, it was like, “Oh, shucks, that’s never happened before.” It’s like, “Oh, well, maybe we should go with someone else.”
Jess Lindgren
Maybe it’s a different, yes, maybe you go with a different candidate if that’s never happened. Process evaluation and improvement is, honestly, my favorite thing to do. I’m constantly just like, “Okay, we did it this way. It turned out okay. Is there anything we could have done better?”
Pete Mockaitis
I like that. And then, so I think, as we talked about recruiting, hiring, we were thinking about it perhaps from a vantage point of a dedicated, full-time, or many hours of time person. I guess in the universe of acquiring assistance, I suppose there’s a whole spectrum from a full-time, 40 hours plus a week person, like on site, to remote, to asking a bot to do a thing, or asking a service. How would you lay out the spectrum or continuum of assistance? And what answer is probably right for what needs?
Jess Lindgren
Yeah, that is a wide spectrum. So, there are lots and lots of options out there. I will say that a bot, or your average ChatGPT or AI, I am not a fan. I really think work like this is nuanced. Like, people in the executive assistant sphere are, “Oh, my God, AI is going to take our job.” No, it’s not. It’s fine. Like, there’s way too much nuance in a lot of work.
And if the things that you need help with are things that can be automated by a bot, or an AI, you don’t need an assistant. But I do think that most organizations and most individuals, especially individuals running companies, really could benefit from having one, whether it’s five hours a week to 40 plus. When you get into that 40 plus timeframe, hire a second person. It is absolutely unfair to have, like, I’ve worked 60-hour weeks. It’s not fun or cute for anybody.
Your productivity, your effectiveness, your efficiency, totally starts to drain once you’re past like 35 to 40 hours a week. It just, it’s not sustainable, you know? But, yeah, there’s definitely opportunities. There’s virtual assistants based out of the Philippines. Like, that’s a very strong industry at this point. It was definitely something, when I started my company back in 2014, it was, “How do I differentiate myself?”
Like, VAs out of the Philippines were newer. But like, “How do I differentiate myself as the in-person personal and executive assistant here in the United States who is not charging $5 an hour? Like, how do I?” Because it is different. It’s a very different service. It’s a very different product that I have to offer.
And, yeah, you still can, like it’s a much more developed and stronger industry. People based in other countries outside of the US have seized the opportunity. I don’t want to say taken advantage of the opportunity because that’s not the right wording, but like seized the opportunity. There’s a demand, and people are meeting it. And I’ve heard nothing but wonderful experiences that people have had with virtual assistants based out of other countries.
And you can get five hours a week. You can get 20 hours because you had a busy month or maybe you had a launch coming up. You can hire someone for 40 plus, like that’s, honestly, how I started working with my current executive, is he hired me for a one-off project. And after that one-off project was done, he was like, “Well, do you want to help me maintain it?” because I was hired to tame his inbox.
Like, we went from 9,000 unread emails to inbox zero. And he was just like, “Well, you cleaned it up. Like, I can’t maintain this. Like, can I hire you to stick around? Can you do 10 hours a week for me ongoing?” And I was like, “Absolutely.” And then 10 turned to 15, 15 turned to 20, 20 turned to 60. I hired that second person, and then you adjust from there.
Pete Mockaitis
Well, that’s beautiful. And kudos to jobs well done. I mean, that’s often the reward for great work, is more work.
Jess Lindgren
It is more work. But, you know, when it’s work that you love, it is a reward.
Pete Mockaitis
All right. So then, we talked about there’s full-time, there’s half-time, there’s other countries like the Philippines, there’s the bots can do what the bots can do, but they are limited, all right.
Jess Lindgren
Very limited.
Pete Mockaitis
And so then, I’ve heard there are a number of services. I’ve tried Fancy Hands, and it’s quite limited.
Jess Lindgren
Okay, that’s a new one to me.
Pete Mockaitis
Well, the nature of the tasks were limited, in that they’re like 15-minute requests. So often, like it’s really crap shoot. It’s kind of like an Uber situation. It was like, you’ll get who you get and, hopefully, they’re with it. But it’s hard to say, “Oh, you’re great. Let’s keep doing the thing.” It’s like, “Well, no, you might get me next time. You might not.”
Jess Lindgren
Oh, you might never get them again. Interesting. So, it’s not something where you can say, “Okay, Jess did a great job. Five stars. I want her again.” Interesting. Fancy Hands. I’ll have to look into that.
Pete Mockaitis
Yes, so it’s very limited, such that I’ve actually had a hard time using my requests, and I’ll probably be canceling them shortly. So, are there any other services or resources or directories or agencies or spots folks can go, and say, “Oh, they usually have some great folks”?
Jess Lindgren
You know, there are agencies out there, the ones that I have personal experience with, and the ones that I’m familiar with are, unfortunately, out of business.
Pete Mockaitis
Oh, bummer.
Jess Lindgren
Yeah, so I don’t have specific agencies, necessarily, to recommend at this point, but I can say that there are more people who would be great at being an assistant in your network than you probably could ever imagine.
Like, the number of people who have a kid in college, who has 10 hours a week to give you, or the stay-at-home mom who’s been out of the workforce for a number of years, and, thankfully, kind of like the emotional intelligence piece, like people place more importance on the emotional intelligence piece. People are less, like there used to be a big stigma if you had a huge gap on your resume like that.
But people are really coming around to, “Okay, a stay-at-home parent is, like, the perfect person to hire for a role like this because they are managing a household, they’re managing children’s schedules, they’re managing all, they’re feeding however many people, however many meals every single day, they’re staying on top of laundry.”
Like, being a stay-at-home parent is a whole huge job and a really untapped market. Like, you just never know who has, like a friend of mine, their youngest just went to kindergarten this year, so all three kids are, like, eighth grade, fourth grade, kindergarten. All of a sudden, the stay-at-home parent has two, three hours a day where they could pick up some work, if someone had it available for them.
So, really, I like to recommend that people just put out, especially when you’re in a position where you have a podcast, you have a newsletter, you have social media, “Hey, friends, hi, I’m Taylor Swift, and I’m asking the Swifties. I’m looking for, hey, Swifties, I’m looking for an assistant for 10 hours a week. Who can help?” Taylor Swift is going to get a slightly different response than you or I would, you know?
Pete Mockaitis
“Ahh!!”
Jess Lindgren
And, Taylor, if you’re hiring, hello. But just, like, ask, and you just never know. Like, that’s how I ended up in the role that I have, is I wrote an email, I quit my job, I threw a party and just told everybody I knew about it and I was like, “Hey, you should come to this party, and here’s what I’m doing. I’m, basically, what people now might call a fractional executive assistant.”
So, I was like, “Fractional executive assistant work. And I guarantee, if I can’t do what you need, I know somebody who does.” And 15 minutes after I sent that email, someone reached out to me, and said, “We have a job for you.” And 12 years later, I’m still doing that job.
Like, the power of networking is so real and you will see people all the time say, “It’s not what you know, it’s who you know.” That’s unfortunate because not everybody knows everybody. But when you do know some people, it can be very nice and very cool.
Pete Mockaitis
Yeah, I’m thinking about my buddy, Scott, mentioned, I think, one of his kids’ friend’s moms, they just had a number of very pleasant exchanges with her, and she indicated that she was looking for some stuff to do, I think, with kids in school situation. And they said, “Well, hey, maybe you could help us with this and this and this.”
And now, there’s like just a growing list of, she does all these things that make their life work in terms of, “Well, hey, could you help coordinate some things with our Airbnb property? And could you coordinate these Amazon returns?” And so, there’s like a dozen bullet points or more by now. And so, it just seems like, “Are you a billionaire, Scott?”
He’s like, “No, no, he’s not. But he’s found someone delightful who does have that helper’s heart, who just enjoys doing this, and they appreciate just the heck out of her,” because, like, “Oh, my gosh, our lives are so much less stressful and more wonderful because you’re in it. Thank you.” And she’s happy to help, and, it’s win, win, win, win.
Jess Lindgren
Yes, that’s the phrase I tell to everybody. Like, anybody reaches out, and I’m like, “Happy to help. I’m going to write a book someday. Put a pin in that.” But truly, like, everybody brings different skills and different tools to the table. Money is a tool. Stop hoarding it. Start using it to make your life better.
And the stay-at-home parent who was looking for a few things to do, as their responsibilities at home start to change, as the kids get older and maybe graduate, go off to college, all of a sudden that person has more time, effort, and energy to put into their work. You can take more things off of the person that you’re working with. You can take more things off their plate. And it’s a very reciprocal symbiotic relationship. And, yeah, it can be really great for everybody.
Pete Mockaitis
Well, let’s talk about the assistance and the assisted relationship, and that doesn’t necessarily need to be an executive, per se. I think there was even a piece recently in the Wall Street Journal or New York Times about how, “Hey, normal professionals are hiring assistants now, and it’s just so great.” So that’s cool.
The term executive assistant is, I don’t even know, if it’s the one to use. You may or not be an executive and assistance is great for you, regardless. So, tell us, within the relationship, what are some top dos or don’ts? What are things that drive you and other assistants just nuts, like, “Don’t ever do this. This is so, I don’t know, demeaning or frustrating or annoying.”
Jess Lindgren
Ooh, those are good questions. So, really, I just touched on this. Money is a tool, don’t be stingy. Pay your assistant well, pay them better than you think. You’re going to get what you pay for. If your budget is $5 an hour, you’re going to get very different service than if your budget is $150 an hour. And, like, that’s what I charge and that’s what I get paid, and that’s what I do. I mean, depending on the project.
But, you know, like your budget is very different and you’re going to get people who can prioritize things differently for you. So, like, really, if you, as an executive, I mean, even if you’re not like an executive-executive. You are the executive of your home. You can call them personal assistant, if executive assistant feels wrong. You can just say assistant. Like, we don’t really get super hung up on titles, but, like, pay them well.
If you’re some Fortune 500 executive-level, director-level, manager-level person who’s pulling in $500,000 a year, you have a budget to pay for someone good, and you’re going to get what you want the better that you pay. So don’t be stingy. You also need to not be a micromanager. You need to understand that people who are assistants are professionals. We’re good at what we do, especially when you’re talking with somebody like me who has been doing this for 20 years.
I am fantastic at what I do. You can give me very vague instructions. You can throw me into the deep end. I’m going to swim. It’s fine. You don’t need to hire me slowly. You can just bring me on and say, “Okay, here’s this whole backlog of tasks. Start wading through things.” Like, I love fixing problems. I love untangling messes. I love doing those things that feel so impossible to you, that feel your to-do list is just, it’s a list of things for me to just check boxes off of.
It doesn’t have the same emotional weight or stress associated with it for me. So don’t be stingy. Don’t be a micromanager. Like, tell me what you need done and then trust that it’ll get done. If it doesn’t get done, you’re going to know about it and then you can step in and micromanage, or whatever. But, like, back off.
Like, tell us what you need us to do and then let us do it. Give us some breathing room because we’re professionals and we’re good at it.
Pete Mockaitis
Well, I guess I’m thinking about the universe of expectations. And, for example, and I don’t know if this is a dated reference. But, I think, I’ve heard instances of, “Oh, if someone is getting coffee and getting dry cleaning, like that’s demeaning and beneath them.”
But, in other ways, another way of viewing it, it’s like, “Oh, that’s exactly what is needed and is helpful for that person at that time.” And so, I guess I’m guessing, you tell me, that whether that is or is not appropriate or, you know, “Pick my kids up from daycare,” or school, or karate lessons, really just depends on communicating those expectations upfront, and seeing if that’s a fit.
Like, you know, “Actually, driving kids around is something I can’t stand doing for whatever reason. They’re noisy and they are sticky.” Or, like, “Oh, how delightful. I get to spend some time with these precious cherubs.” So, I’m guessing that’s a do is to be clear about expectations and get aligned, and you can be able to share either way, like, “Actually, that’s kind of outside of our scope and not really in my zone of skills,” and just doing that dance.
Jess Lindgren
Yeah. So, that really is communicating what the job description is, because when you say executive assistant, that has the connotation of being, at least in the United States, you know, other countries like the UK, if you have seen any references to this at all, whether in the business world or the entertainment sphere, you’ll see people talking about their PA, their personal assistant.
So, in other countries, the title does mean something different. But here in the United States, executive assistant has the connotation of being a person who helps you with your professional life. Whereas, a personal assistant is the person who helps you with your personal life, or your assistant, again, whatever title it is that you’re going to give it.
I talk a lot about your time split, like how your job is split between professional and personal responsibilities. In my present role, it’s like a 95-5 professional to personal split. So, like 95% of the time, I’m doing professional stuff, and there’s a pretty, not a hard line, but like I don’t do any of the personal stuff, and that’s fine.
And I’ve also had roles where it’s like 95-5 the other direction. I’m just doing personal stuff. I’m helping you with, like one of my favorite things I ever did. I got hired to help someone hire and manage a plumber. They had a leak under their sink. So, like, I had to vet the different people who were available. Thankfully, I had a plumber that I loved.
So, I just hired them, came over, had to buy them, you know, they’re like, “I need a new vacuum. I need a new cat tree. I need a new…” whatever. So, like, got to knock everything out, like had everything delivered to the house the day that I was coming to manage the plumber. Got to just sit at the house and manage this service person, while they were there. And then I got to take their Instagram celebrity cat to the vet.
And so, you know, like sometimes it can be, I think that stuff is really fun and really cool. There are people who do not want the responsibility of being in charge of someone’s pet, being in charge of someone’s children. So, like, just making sure that the job description is clear from the get-go of what it is that you, the person needs help with, and what you are expecting the assistant to do, because you can also hire five-hour a week professional support and 10-hour a week personal support.
I like what you said, though, about things that are considered dehumanizing. I don’t find it dehumanizing when somebody, when my executive, like in my current role, when we work together in person, a lot of it is making sure that he is fed and hydrated and caffeinated. And that’s not offensive to me. I love doing that stuff. By feeding him and giving him coffee, he’s able to do his job. Like, that is not offensive.
Pete Mockaitis
Well, that’s, “How Pat going to be ‘super stoked’ if one of these fundamental needs are missing?”
Jess Lindgren
Right? Like, this is just basic needs. Like, his shelter is taken care of because I got him a hotel room. His food needs are taken care of because I, literally, scheduled into his day, “Okay, here’s where you have a break. Here’s where you’re going to eat a Caesar chicken salad.” And I have protein bars in my bag. Like, that’s not offensive to me.
But some people, that would be very offensive. What is very offensive across the board is people not having their tempers in check, “I’m not your mother. I’m not your wife. I’m not your teacher. I’m not your daycare provider. Like, grow up.” That is absolutely unacceptable. I don’t care what it is that’s frustrating you. You need to have your temper in check.
And if that’s not something, that not a skill that you currently have, you need to work on that. And you need to hire somebody else who is fine getting yelled at. Like, treat people with basic respect. I have been yelled at. I have had things thrown at me.
Pete Mockaitis
Oh, jeez.
Jess Lindgren
Like, seriously, I have had people, you know, throw a sheaf of papers, like, right into my face. And I’m like, “That is unacceptable.” So, like, have your temper in check, have your behavior in check. This is either a professional office or it might be inside of your personal home. But when you are bringing someone in as a hired professional, whatever that profession is, get it together.
That’s the dehumanizing stuff. That’s the unacceptable stuff. The number of times I’ve heard from assistants that, “I got yelled at yesterday, and it was worse than last week.” And I’m just like, “This is escalation. This is abusive. This is not okay. And, like, don’t tolerate that in the workplace.” But, like, also, if you’re the person who’s hiring the assistant, don’t act like that.
Pete Mockaitis
Yeah, absolutely.
Jess Lindgren
Yeah, that’s the unacceptable stuff. Like, anything else, like job duty-wise can definitely be negotiated. And if you don’t, as the assistant, want to be the person who gets the coffee or the dry cleaning, it’s 2025. Like, Uber Eats is a thing. There’s plenty of services that will deliver your dry cleaning.
Pete Mockaitis
That’s right, “I will coordinate the delivery services associated with these tasks and forward you the bill.”
Jess Lindgren
Yes, you can be the person who does the project management of it, right? But you don’t have to be the person physically going to the coffee shop. You don’t have to be the person carrying the dry cleaning down the street. Yeah.
Pete Mockaitis
And when you brought up those examples of the plumber and the cat, and you mentioned that, “It’s your to-do list. I don’t have any emotional pulls associated with it,” I think that’s a really great concept to highlight here, is that there are many things that I think we’re capable of doing, but we have some sort of emotional resistance.
And so, like, I’m thinking about, “Oh, I should probably upgrade my video backdrop, but that feels like such a project. And I’m going to have to talk to a dozen different salespeople who are going to ask about my needs and my desires and my measurements.” And because I just have emotional resistance, like I’ve been dragging my feet, I haven’t really done it.
Jess Lindgren
Yeah, for sure.
Pete Mockaitis
And yet, if someone else who’s just like, “Okay, I feel totally neutral about that. I would be happy to pull together all of those options and go through that legwork of talking to those people and relaying those measurements and your preferences a dozen times so as to find a winning option for you.”
Jess Lindgren
Yeah. And the other thing that a great assistant will do is say, “You know what, Pete, you don’t have to take a dozen meetings for that. You need to take three to five meetings. You need to pick the person who…you know, I’m already lowering your ceiling of 12. I’ve lowered your ceiling to five. I’m not going to talk to more than five people.”
And if I already have a service provider or, “Oh, hey, I had a video backdrop created. Just last year I have a great service in mind.” Now you’re talking to zero people. You’re just giving me a credit card so I can order it for you.
Pete Mockaitis
That’s good. Beautiful. Well, tell me, Jess, are there any other key things to keep in mind before we hear about some of your favorite things?
Jess Lindgren
Key things to keep in mind is just, I really love to recommend to people that, when they’re getting ready to hire an assistant, it means that they have been ready for six months to a year. So, like, it’s time if you’re really thinking about it, that means that you have been ready for a while. I want you to talk with the people that you work with.
So, if you are the manager of a department, talk to all the people that you interact with for a week, just say, “Hey, if I was going to hire an assistant, what do you think I need help with? What do you think I could offload from my plate?” And you just never know what things that you, I don’t want to say complain about, but like what things do you say like, “Ugh, it’s time to do the TPS reports.”
Like, maybe you need somebody that you can hire that can help you do the TPS reports. And, again, you’re too close to it. You’re too in it. You are just in it. You’re bogged down by the emotional weight of everything that you have outstanding to do, and it’s hard to even know what you might need help with. So, ask the people around you that you work with.
Ask the people around you at home, because you definitely don’t know, what are you letting off steam about to your spouse, to your children, to your friends, to your family? What did they hear when they say, “How’s work going, Pete?” And all they hear about is the quarterly inventory night or whatever.
Like, your assistant could come in and totally revamp the process to the point where you get excited about doing quarterly inventory, because now that it’s been evaluated and optimized, it’s, all of a sudden, really exciting and everybody orders pizza and it only takes three hours when it used to take eight. And now it’s like a big company party because you hired this person to come in and help you.
Pete Mockaitis
Yes, I like that a lot. And I think that this notion of the emotional weight of things is powerful in terms of it’s not just a one to one, you know, hour-dollar exchange situation. Because if you have a lot of emotional angst associated with, “Oh, I’m dreading this, leading up to it. And then, afterwards, I’m so drained from having done it. And then I’m complaining about it.”
It’s like, you may have paid for one hour of services that goes away from your plate onto the assistant’s plate. And yet, that has freed up more than an hour of product goodness in your world.
Jess Lindgren
Yes. Yes, absolutely. And, like, the other thing I really like to tell people is make a list, no matter how big or how small, because you touched on this, too, that there’s a lot of people who feel like, “Oh, well, I should,” or, “I already know how to do this. Why can’t I fit this in?” Everybody needs rest and recovery time. And so, you are buying time, you’re buying services, you’re buying expertise from someone who can help you.
And again, it’s 2025, almost 2026, some crazy how. There is no shortage, depending on where you live, of things that you can hire out. There’s a really great site called Care.com. It definitely is geared more toward housekeepers, nannies, that kind of role. You don’t know what retired grandma, that lives right around the corner from you, wants 15 hours a week, of picking the kids up from their activities, folding your laundry, and making dinner for everybody.
You just don’t know until you pay Care.com for a subscription, you invest the money, because Care.com is going to give you, like they do the vetting, they do the, you know, they’re saying, “Okay, here’s the five candidates that we think, based on what you’re looking for help with, that you might like.” You, ultimately, have to interview them, make the decision.
But, like, Care.com, they’re the hub for you, where the people come that are looking for work. When you ask your network, when you say, “You know, these are the things that’s kind of a weird mishmash of personal and professional stuff that I need help with,” you don’t know who has five or 10 or 15 hours, and who has what expertise and interests to bring to the table for you. Ask.
Pete Mockaitis
Perfect. Thank you. Now could you share a favorite quote, something you find inspiring?
Jess Lindgren
Yeah, absolutely. My favorite quote is from Leslie Knope, the character from Parks and Rec, “One person’s annoying is another person’s inspiring and heroic.”
Pete Mockaitis
Thank you. And a favorite study or experiment or bit of research?
Jess Lindgren
A favorite study. So, I really love the Pareto principle, the 80-20 rule. Just 80% of your client, like, especially as an administrative professional, 80% of the emails I receive, one minute less don’t even need to be answered. Twenty percent of those emails are going to take up 80% of my time. It’s just all day, every day.
Pete Mockaitis
Yeah. And a favorite book?
Jess Lindgren
I really read a lot of fiction. I am a huge The Hitchhiker’s Guide to the Galaxy gal.
Pete Mockaitis
Yeah. And a favorite habit?
Jess Lindgren
Favorite habit. I love to get enough sleep and drink enough water and get enough exercise.
Pete Mockaitis
Agree. And is there a key nugget you share that is frequently quoted back to you, a Jess original that people find so delightful?
Jess Lindgren
I would say the biggest thing that I put out into the world is the five W’s, the who, what, when, where, why of it all. Like, really, just any problem, any situation, can be solved or enjoyed or put together with the who, what, when, where, why of it all.
Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?
Jess Lindgren
I would love it if you checked out my website JessLindgren.com, J-E-S-S L-I-N-D-G-R-E-N.com.
Pete Mockaitis
All right. And a final challenge or call to action for folks looking to be awesome at their jobs?
Jess Lindgren
People looking to be awesome at their jobs, stay hungry and stay foolish.
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