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How, Why, and When to Hire an Executive Assistant – Jess Lindgren
The Agents of Change

How, Why, and When to Hire an Executive Assistant – Jess Lindgren

Do you frequently find yourself wishing there were more hours in the day to get everything done? Or perhaps wish you had a way to clone yourself so you’d be better able to stay on top of things. Or maybe you just need to better delegate some of the stuff on your plate to someone else, so you have more time for the things that only you can do. Well, according to Jess Lindgren, you’re already 3 months too late. 

A smart boss knows they aren’t the best person for every job that needs to be done, so they hire people for those tasks. Whether it’s more on the personal side or business side, an assistant can make a world of difference for your business productivity. And what further makes hiring an assistant a reasonable option is the flexibility you have in deciding what role – and how much – that person will play for you.  If you think you can’t afford it right now, maybe you actually can’t afford not to, if you want to start seeing more growth in your business and time in your day.


Rich: My next guest delights in the details. Whether she’s planner her 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 3 cats, you’ll find them exploring museums or indulging in theater performances wherever they find themselves around the world.

A lover of putting pen to paper, she gleefully reads and replies to every handwritten letter she receives. I am very pleased to introduce, Jess Lindgren.

Jess: Hi, Rich.

Rich: It’s good to have you on the show, Jess.

Jess: Yes, thank you so much for having me.

Rich: Now you are an executive assistant. How did you get started in that?

Jess: Wow. That is 15 years ago, I just kind of fell into it. I was actually working at an amusement park, of all things.

Rich: Are you a carnie?

Jess: No, no, goodness, no. But just, you know, college jobs, you do what you can that fits in with your schedule and with a lot of flexibility. And I just ended up spending a lot of time in the operations office where all the executives would hang out. And from time to time they would say, “Ok Jess, can you help me with this or that?”, and it was kind of going above and beyond what your traditional guest services person at an amusement park would be. And just kind of fell into more and more jobs from there and truly this is something that I had always wanted to do. Just kind of a glam – to me – role; “Oh, yes Ms. Lindgren, can you please make sure that we have a reservation for tonight”, and “A gift for my wife and flowers for next week, and get yourself something nice while you’re out there, too.”

Rich: Well, especially that last part, that’s awesome.

Jess: You know, just little tokens of appreciation, always nice.

Rich: Now you bill yourself as an “executive assistant”, is that the same thing as a “personal assistant”?

Jess: It really depends on where you are in the world. In the U.K, “PA” – or, “personal assistant” – means pretty much the same thing as an “executive assistant”. In the United States a personal assistant is a little more “Hollywood”, if you will. And I’ve know people so it’s not exclusive to California or Hollywood by any means to have a personal assistant. A personal assistant is a little more of that, “pick up my dry cleaning”, “make sure I have my favorite coffee”. I’ve done work for people before where it’s strictly personal; birthday parties, gifts, and all that personal stuff. But the executive assistant usually involves a lot more professional stuff; scheduling travel, managing email, helping run reports, that kind of stuff.

Rich: So I know a lot of people who tune into this podcast are pretty busy entrepreneurs, business owners, and marketers. How do we know if we need an executive assistant?

Jess: If the thought occurs to you that you need an assistant, you are already 3 months too late. You needed an assistant 3 months ago. I firmly believe that an assistant should be one of the first hires that you make, because if you sit down and you look at what your billable hourly rate is to the overall health of your business, you absolutely should not be booking your own travel. You should not be assembling your own meeting materials. You should not be coordinating when you have a speaking engagement, you should not be doing that back and forth. If you’re setting up an interview with somebody to be on your podcast, your assistant should absolutely be, “Here’s the scheduling link to be on Agents of Change. Here is everything that I need you to know before you come on the show”. Because that way you can focus on what you’re good at that brings money into the door, and then you can afford to pay your assistant.

Rich: Alright. So if we’re sitting here and you’re saying we realize we’re already 3 months too late, how do we find the right person? Is it a personal ad, is it a specific search group that we engage with, how do we find that person?

Jess: My favorite piece of advice for people when you’re looking for that person is to look and think outside of the box. In today’s world you do not need to write a big, long job description. You do not need to post your job description anywhere unless you think you have the time to sift through 100-1,000 resumes to find the 1 or 2 good ones.

Truly you need to start with your network, start with the people that you know. And just think about, you never know whose kid is home for the summer and needs 10 hours a week. And especially something like an assistant role, I’ve done very successfully for 5 years on a remote basis. They can start with you while they’re home from college, and then continue working with you after you’ve established that baseline, very easily.

Rich: So what does this job pay? Like, what should we be willing to pay to bring somebody on as an assistant?

Jess: That’s a really great question because assistant roles have historically been very underappreciated, undervalued, underestimated, and underpaid. I firmly believe that if you want a good person you need to be willing and ready to pay for that. Think about the overall financial health of your business, think about what your hourly rate is.

Let’s say if you bill out at $500/hour, you should be willing to pay somebody $40-$50/hour. That’s 90% less than what you charge. That’s not a very popular opinion. If you look at the way assistant roles are built, I think my favorite one – this is several years ago – somebody was looking for an assistant on Craigslist. And they wanted that person to have administrative assistant experience of 3-5 years, they wanted a college degree, they wanted A/P and A/R experience, this person needed to be able to administer benefits and be the HR person, and they were willing to pay this person a grand total of $7/hour.

Rich: Alright, well that seems definitely a little bit extreme.  

Jess: Right. But still even today you get people, when I tell you that you need to pay a bare, especially if somebody is an independent contractor, minimum $35/hour. People really get nervous about that. But it’s worth it and you need to be willing and able and ready to pay the right person for them to stick around and do a great job for you, because truly you get what you pay for.

Rich: I think it’s because we combine maybe a virtual assistant with a personal or an executive assistant, and we’ve heard that we can get people for $10-$15/hour from somewhere else in the world. I mean sometimes I’ve even heard people pay like $4-$5/hour, so maybe that’s part of the confusion. But I think what we’re talking about here is somebody who’s going to be really involved with your business or your personal life, and we need a higher level of competency.

Jess: Absolutely.

Rich: So over the years I’ve thought about getting an assistant on and off. I think my biggest hang up is what exactly is this executive assistant going to do for me. I struggle with just what exactly am I going to outsource to this person. Can you help me with that a little bit?

Jess: Absolutely. When it comes to outsourcing each executive is different, and each assistant is different. So you just need to be very honest with yourself about what it is that your pain points are. So truly sit down, make a list, no pain point is too big or too small, there are no right or wrong answers. You can outsource literally anything to that person.

Let’s say I’m your new assistant and if you were to say to me, “Hey Jess, I really need somebody to come clean my house, I need somebody to clean up after my dog in the backyard, I need somebody to get my dry cleaning for me.” I live in California, I’m not exactly local to you. And even if I were local to you, a lot of those things I’m just not very good at. I might not be able to come clean your bathroom for you, but I can absolutely find the person who can and then manage them for you.

So really what it is like I said, sitting down and making a list of what your pain points are, there are no wrong answers. Talk to the people around you, talk to the people that you work with – whether it’s your friends or colleagues, your clients – you just never know what it is that you’re saying out loud, “Oh, I just wish that I had somebody to help me with x, y, z”, “Oh, I need to go home today, I can’t meet with you this afternoon because my ‘to do’ list is a mile long.” You don’t know what things that you say that you need help with that other people around you pick up on, and that can help you notice the trends.

Rich: What do you think about just writing down everything that you do over the course of the week and seeing which of the things you’re either not so good at or just hate doing?

Jess: Absolutely. That’s helpful, that’s extremely helpful, too. And it’s great for you to know where your time goes, you’ll be able to see gaping areas where you’re just like, “OK, I should not be doing this, someone else should.”  And it may not even necessarily be an assistant, it may be, “Oh my gosh, I’m doing invoicing, shouldn’t my accountant be helping me with that?”

Rich: Right. How about those people that say, “Listen, if I want it to be done right I’ve got to do it myself”, what do you say to those people?

Jess: I say to those people that delegation is an art form, it is something that requires a lot of practice, to be perfect, I am very much one of those people myself who believes that if something needs to be done right, I am the person who needs to do it. However, if you surround yourself with people who are smarter than you, people who are better than you at the things that you’re not good at, it just makes your life so much easier. And in the same process, you’re helping somebody else live a better life, too.

For example, my assistant – yes, I am an assistant who has an assistant – my assistant is fantastic at killing a ‘to do’ list. She’s the person that when you have things, she’s good at killing that ‘to do’ list, and she’s great at things that need to happen on a certain day or at a certain time, or anything that needs to happen every day – something that needs to happen Monday through Friday – she is so good at that stuff. I sit and look at that stuff and it drives me crazy, it just feels like busy work. I give it to my assistant and it just all magically gets done and it feels amazing.

And then at that same time, I am helping her live a really comfortable, really happy, flexible, supported lifestyle.

Rich: So once we’ve decided or maybe even found this person, how exactly do we onboard them? What does that process look like or what tips do you have for us in terms of bringing that person on board?

Jess: When you bring that person on board the first thing that you need to do is carve out as much time as possible. You need to be available to this person, you need to be very honest with yourself about your communication style. Some things that I really strongly recommend that everybody do on both sides of that relationship – both the executive and the assistant – is take the strengthsfinder test, take the Myers Briggs, really see how your strengths and weaknesses complement each other.

And then after you’ve brought that person on – so hopefully do all those tests before you commit to hiring someone – but once you’ve picked the person and you’re ready to start training, you need to be as available as possible and you need to talk to that person and ask how do you learn best. And then you need to be willing and able to teach them in that style that they learn best. If they learn best through a screenflow video, you need to sit down and make videos of every single thing that you need them to do. That’s a one-time investment, it’s a lot of time and effort up front, but then your assistant has those videos forever.

Like me personally, I never watch videos. Don’t waste your time if you’re hiring me, don’t waste your time making me videos because I’m not going to watch them. I want to shadow you and learn while doing, or I just want you to throw me into the deep end and I’ll do it and say, “This is how I think you would do this, am I correct?” And then before pulling the trigger on whatever it is, then I’ve had time to meet with you and confirm that’s how you’d want it done.

Rich: Ok, that makes a lot of sense. Now one of the things that I might want this person to do is to vet my LinkedIn requests, and my Facebook requests, and even run my email before me. Should this person pretend to be me, should they be The Rich Brooks as far as the outside world can see?

Jess: My feeling on that is, no. Truly because you don’t know what your assistant may have said to someone out in the world. Yes, they are definitely acting in your best interests on your behalf. But then when you see someone in person that says, “Oh, hey Rich, do you remember when you said x, y, z via email?” And you’re like, not really.

So there’s two sides of this her. If the person is totally flying solo I firmly believe in, “Hey, this is Jess here on Rich’s behalf”, and then you’ve set the expectation for the person on the other side of who it is that they’re speaking with, they know that they’re being taken care of faster maybe by me being the liaison to respond.

But then there’s something, too, when you have a weekly or daily or however often one-on-one with your assistant and then they say, “Ok Rich, a person emailed in and they need to know this”. If you dictate something to that person, then absolutely they can pretend to be you. But that’s dictations, it’s not just them taking the initiative and pretending to be you. Because that way at that point, you know what’s said even though you’re not the person that did the typing, you know exactly what was said and what’s going on in that conversation.

Rich: So you touched on this a little bit before in terms of both people coming and being open and honest. But what makes for a good, healthy relationship between the entrepreneur and the executive assistant?

Jess: You definitely need to trust each other, that’s a huge one. If you don’t trust each other than what are you even doing? You’re going to give this person presumably access to lots of personal information. Over the years I’ve handled people’s address, social security numbers, credit card numbers, all that stuff, and you need to have a high level of trust with that person.

If your personalities don’t mesh, that’s 95% of your success. So you need to like the person, you need to trust the person, you need to be comfortable letting this person in. You really have to have a shared passion for whatever it is that you’re doing. For example, I worked with a group for a while who were Burger King Franchisees. I’m not particularly passionate about fast food, that was not an easy role for me. So you really have to have some investment in whatever the company’s mission is, whatever your entrepreneur’s mission is, that’s really important.

Rich: Jess, how do I know if things aren’t working out with this person and how do I handle that? What are some of the signs that I should be looking for and how do I get feedback in a way that might fix things that are fixable?

Jess: So the signs that you’re looking for are if you gave someone tasks to do, generally speaking, the executive assistant should basically be an extension of you. So the things that you are giving this person to do, you will notice if they’re not getting done. If you don’t have a flight on your calendar, if you don’t have an itinerary on hand for your next speaking engagement, you’re going to notice that things aren’t getting done.

The way to really get that feedback is when you’re doing that initial training, ask the person how they best receive feedback. If I have a problem, how do I talk to you about this? What is the best way for me, personally? I want you to shoot straight, I don’t want you to dance around the issue. I want you to tell me and say, “Hey Jess, you messed up.” And I’m the first person to admit when I did mess up. How can we learn from this and do better?

At the heart of that issue, though, hire slowly and fire quickly. So when you are bringing that assistant into your life, to start off you do not need to give that person 10, 20, 30, 40 hours a week. You can give that person a one-off 5-hour project that does not delve super deep into company information, your personal information, and you can just get a sense for how that person works, how quickly they work, how they deliver results.

And after the first 5-hour project has been successful, move on to a 10-hour project, move on to a 15-hour project, and just go from there. And if things don’t work after the first 5-hour project, no harm no foul.

Rich: This may be a little bit in the weeds but are these positions usually an employee, or is it more of a 1099 situation?

Jess: It depends on how you have your business set up, what your preferences are, and what your assistant’s preferences are. So yes, this does get very nuanced and it’s very specific situation by situation. My assistant, for example, is a contractor. I have no desire to have employees running through my company, and I’ve done a lot of really successful 1099 contractor relationship work myself over the last 5 years.

 I personally prefer contract work because I get paid for every minute that I’m on the clock, I get to set my schedule, while obviously delivering the level of service and results that my Executive expects. But for me personally, I think I’m kind of unemployable at this point. So it really just depends on the person.

Rich: What are some of the first tasks that you’ve seen out there that people should be thinking about giving up? Like, what are the things where if I’m just getting started in this and I’m not sure how comfortable I am doing this, what are some easy wins for me as the entrepreneur or business owner?

Jess: Easy wins. So that’s going to really, again, that’s kind of one of those nuanced questions depending on what your preferences are. And also it depends on what your comfort level is with delegating professional stuff versus personal stuff. You definitely need to determine what percentage of personal versus professional, and that’s another one of those places where there’s no wrong answer, whether it’s 80% personal and 20% professional, or the other way around.

So just quick wins. If it were a personal thing, can this person schedule a dog walker and did the dog walker do a great job. Did the housekeeper show up on the day at the time that we agreed on? If it were a professional thing, did this person pull the right report after I gave them a little bit of training? Or if you use a specific piece of software, did the person just dive in head first and say, “Oh no, you don’t need to train me. I’ll get through the knowledge base and I’ll get you that result”, because that’s a really big characteristic that you’re looking for. A good executive assistant is somebody that, even if they don’t know the answer or they’re not familiar with a piece of software that you’re using, they have that innate thing inside of them, that innate desire for knowledge and curiosity to go out and figure it out themselves.

Rich: That makes a lot of sense. If there was one piece of advice that you would give to somebody that’s considering and executive assistant after listening to this interview, what would it be?

Jess: My piece of advice would be, find somebody. Find somebody and start that relationship. Again, it ties into the “higher slowly, fire quickly”. You just never know what kinds of things you can outsource to that person that will make your life that much easier.

I know that when you’ve got a family and other people depending on you – a significant other, maybe some children – freeing up your time to be able to spend more time with them, to lower your stress level, to allow when you are on vacation to actually be on vacation because you can trust and know that someone is taking care of things in your absence, is completely priceless to the rest of your family and the people around you. 

Rich: Awesome. Jess, I’m sure a lot of people would like to learn a little bit more about you. Where can we send them online?

Jess: You may absolutely come check me out at jesslindgren.com.

Rich: Thank you. Thanks for stopping by, Jess, it was a great time talking to you and you always have a great approach on how to think about executive assistants.

Jess: Awesome. Thanks so much, Rich, my pleasure.

Show Notes:

Jess Lindgren understands the power of a good assistant and what it can do for personal and business growth. Find out more about how a personal assistant can help you by checking out her website.

Rich Brooks is the President of flyte new media, a web design & digital marketing agency in Portland, Maine, and founder of the Agents of Change. He’s passionate about helping small businesses grow online and has put his 20+ years of experience into the book, The Lead Machine: The Small Business Guide to Digital Marketing