Onboarding Tips and Tricks with Jess Lindgren

Jeremy · 0:00

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Jess · 0:46

Hi there, I'm Jess Lindgren, and today's leadership quote comes from Seth Godin, who says, People like us do things like this.

Speaker 3 · 1:00

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 1:17

Hey friends, just want to let you know, in case you didn't, that my best-selling book, The Leader Assistant, has a companion study and discussion guide to go along with it. It's called The Leader Assistant Workbook. Now, you can buy the Kindle eBook version of The Leader Assistant Workbook on Amazon, or you can go to leaderassistantbook.com and get a printable PDF version of the workbook. This version has all the space and margin in between the questions that you can write your own answers and take notes with. So it's a great way to print it out and keep track of your discussion and study guide notes. Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook. Hey, friends, welcome to The Leader Assistant Podcast. It's your host, Jeremy Burrows, and this is episode 313. You can check out the show notes at leaderassistant.com/313, leaderassistant.com/313 to check out the links and bio and all the fun info about this conversation that I'm excited to be having with my friend Jess Lindgren. Jess, welcome back to the show.

Jess · 2:35

Thank you. It's so great to be here all these years and episodes later.

Jeremy · 2:40

Yeah. So for those of you who happen to miss our first conversation, Episode 23, yes, Episode 23 was published back in 2019, I believe. And you can check out that conversation at leaderassistant.com/23. And yeah, a lot has changed since then, Jess. This is Episode 313. So literally hundreds of episodes, hundreds of interviews I've had since then. And I'm really excited to catch up with you and specifically talk about the topic of onboarding, onboarding an executive, onboarding yourself, all things onboarding. But first, why don't you catch us up? I know, you know, you've maybe relocated and have some changes in your life since 2019. So tell us a little bit about where you're living and what projects you're working on and all that fun stuff.

Jess · 3:41

Yeah, I do. So since 2019, I think life has changed for a lot, if not all of us, quite a bit. Back at episode 23, I was newly living in San Diego. I'd been there, I think just shy of or just after a year. And then obviously 2020 hit the pandemic and the longer things drug on. My husband and I just kind of used to joke with each other like, hey, my sister lives in upstate New York and I don't think they make houses there that are as expensive as what we pay in rent. You want to think about moving up there, like seems like a great time to make a real estate purchase. And just the longer things wore on, we were just like, it became less of a joke and more of a, this is something we could do. So we did, we ended up buying a house site unseen over FaceTime during the depths of the pandemic. Yep, we were going on house tours in August, September of 2020 and put in our offer toward the end of 2020, I think mid-November into early December. We put the offer in, set a close date, wound everything down with our life in San Diego, made a cross-country move in a car with three varying degrees of happy cats sitting in the back seat. And yeah, we call it an overcorrection. We had been living in a two-bedroom, thousand-square-foot condo in San Diego, and now we live in a seven-bed, two-bath, four-thousand-square-foot historic home in upstate New York.

Jeremy · 5:17

Wow. That's a little bit of a change. I'm sure the cats are happy.

Jess · 5:20

So for just two people, the cats love it. They absolutely love it. But it's a lot. There are definitely rooms where we don't set foot for days on end, sometimes weeks, and it's like, whoa, the sitting room. I haven't been here in ages. But yeah, it's been great and just my sister and her husband have three children who were one, five, and nine when we got here, I think. It's just been really great to be part of their lives. We call ourselves professional auntie and uncle. We're involved on the PTA. I always have to think about that because it's not PTO, because that's time off from work. PTA. So we're involved in the PTA, we're involved in the Little League, we're involved, my husband runs the Chess Club and I help him do that at school. We go to everybody's plays and concerts and dance recitals and also the neighborhood, auntie and uncle. It's great. It's really great and just so much flexibility in my work life. Finally have Ask an Assistant. Some of you may know me from the show and if you do, I thank you so much for listening. There's a lot of overlap between Jeremy and I in terms of being executive assistants who create for executive assistants. I just appreciate every single person who takes the time to listen. On top of that, my executive has made a big pivot. He still definitely does a lot with online business and that realm of things. But he, during the pandemic, got a new hobby of collecting Pokemon cards. And now we have a very large, it's 1.2 million and growing subscribers for the main channel. And he's coming up on a million subscribers for his secondary Pokemon channel. And we run Pokemon card events in 2025. It'll be one East Coast, one West Coast. And it's just some of the best, most impactful work we've ever done. And it's so much fun.

Jeremy · 7:20

Wow, that's amazing. That's amazing. We'll have to do another episode on YouTube channels, maybe someday, because that's pretty impressive. Awesome. Well, that is super exciting. And, you know, we have a similar story. I was starting to think about back to where I was, and even in in 2019. And I was in St. Louis and I moved to Kansas City during the global pandemic. Similar to you. I bought a house. I think it was October, September, October-ish of 2020. And it was a fixer-upper. So we, you know, fixer-uppered it. And yeah, it was crazy times. But that's been, I guess, four, five years ago now. So, yeah, it's my kids are 11 and 13 and a joy and a pain all at the same time.

Jess · 8:22

And are they still great artists? Because after our first conversation, your kids sent me the cutest thank you cards with little kiddies drawn on them. They're being on the show.

Jeremy · 8:31

Yeah, they it takes a little bit more work, especially the older my older son. It takes a little more convincing to get him to do art these days because he's too cool, you know, but it happens. My younger son still still likes drawing and creating. So that's awesome. Awesome. Well, let's let's dive in then to onboarding. So in the Leader Assistant community, we have those of you listening who aren't on it. We have a free community on a platform called Circle. You can go to circle.leaderassistant.com and you can join our free forum. And several times over the last few years, there have been threads or conversations about onboarding and whether it's, hey, I'm starting a new job. What do you recommend that I do to onboard well? Or it's, hey, I've been in this role, but my executive for the last few years is transitioning out and I'm getting a new executive and I need to onboard them to the team. Or maybe it's even, hey, I'm starting a new role and I need to onboard, but I'm also starting with an executive that's never had an assistant. And so there's a little bit of onboarding them on how to work with an assistant, utilize an assistant, etc. So yeah, I just want to dive in and I know you've worked with the same executive for several years now and you have done a lot of onboarding and I'm assuming interviewing and hiring and all that stuff as well. So would love to just kind of hear all of your onboarding tips and tricks today and I think it'd be very valuable for the assistant community.

Jess · 10:14

I love it so much. Yeah, I've actually been with my present executive. We just crossed 10 years this year of working together. We are a pretty small team. So Pat has two separate teams, several separate teams that he's a part of, honestly. But the two major teams, one team is like eight people and one is two. It's me and him. So from the backend bones of the structure of the business, it's pretty tiny. But my role before working with him, I was working at a pretty hyper growth startup. We went from 200 to about 650 employees during my, I think just under two years working at the company. I was the office manager and onboarding definitely fell to me as the person in the Minneapolis office, which I had never done before, but got some great guidance from other people in the company, talked with HR to make sure I was doing everything right, crossing all my T's, dotting all my lowercase J's, and just making a really great, really welcoming experience for people was my favorite part of that job. I had never done it before. I was super nervous. I was super worried that I would forget things or when you're onboarding people, I can only speak to my experience in the United States. There are things that need to be done in a time-sensitive manner, like doing your I-9, your employment verification, ability to work in this country, getting those documents. I think the time is three days. You have three days to make sure that the documents are in their system and verified and good to go. It was definitely nerve-wracking jumping into it, but truly turned out to be my favorite part of that role and some of the most rewarding work that I did during my time at that company.

Jeremy · 12:05

Nice. That's awesome. And what, where do you want to start? What do you, do you want to start with like executive assistant onboarding? Do you want to start with, what's, what's, what's maybe a process for an executive that you're trying to onboard? How would you like to kick things off?

Jess · 12:23

I think what I would like to do is just kind of some general onboarding best practices, and then we can drill down into specifically onboarding an executive onboarding yourself as an executive assistant, if that works.

Jeremy · 12:36

That sounds perfect. Let's do it.

Jess · 12:37

Awesome. Depending on the structure of your company, again, I'm working in a company of two, we have no plans to hire in 2025 or anytime soon. If you work in something like a fast growth startup, and again, that's where my experience comes from, so that's the example I'm going to speak from. But I think a lot of this is very applicable to pretty much any situation. The biggest piece, the biggest thing that I want to advocate for in any organization is please do your onboarding in person, if at all possible. Like, it is money well spent, it is well worth the investment to bring somebody. Just the number of times that I've had people live in the middle of nowhere and their internet is terrible, so they can't join the call, or they have never worked in a remote first environment, so they can't figure out time zones, or they've worked at, like, they came from IBM and now you're working at a fast growth startup who is a Mac shop, like everybody only uses Apple computers. They might have an iPhone, but they've never touched a MacBook before. So just having a lot of people in varying situations, it is so, so, so worth it, especially if you're doing any kind of group onboarding, which in a high growth environment, you're probably going to try to onboard two to 10 people any given week. It is so worth it to have people in person. If you have to do remote onboarding, which some companies do, they just don't have the budget, they don't have the time, they don't have a person to do the onboarding. If you really have to do remote onboarding, like I see people asking all the time, what are some fun onboarding activities? And it's like, there's nothing really all that fun about onboarding, like it's a, you know, like it's, it's not an icebreaker at a Christmas party. Like it's, it's a formal process. Like you can certainly make it warm. You can certainly make it engaging. But if you are going to stick with remote, you want it to be short. When I was doing remote onboarding before I started advocating for people to come to the office, it was like a three hour Zoom call with slides. And I didn't want to run the call, and the people on the call didn't want to attend it. Like how many times have you had a three hour Zoom call where you are fully engaged and paying attention once, twice in your entire life? Like, yes, it's just not ideal. So if you are going to stick with remote onboarding, keep it short, keep it sweet, keep it engaging, but not gimmicky. Like you want a lot of involvement. You know, people learn best when there are hands-on activities, things that they can do themselves. Not too early in the day for you or the employee, especially like at the time I was living in Minnesota, I was onboarding people from all over the country. You know, if we had somebody in New York and somebody in California, you don't want it to be 6 a.m. in California, 8 a.m. in Minnesota and 9 a.m. on the East Coast. Like, just pick a time that's not too early in the day to do your remote onboarding. Do it one on one, if at all possible. Like just, it gives you the ability to give that person your full attention. It lets the employee feel comfortable asking questions no matter how big or how small. And yeah, it just, it will go faster. Because if you have a group of 2 to 10 people, you're going to have some people who just run the gamut. You're going to have people who have an attention span of 2 out of 10. You're going to have people that have an attention span of 10 out of 10, and it kind of meets in the middle, but not always. So like doing it one on one, if at all possible just is the best case scenario for everybody, I feel. Develop and maintain a checklist so that all of your bases are covered. Make sure the important HR stuff gets taken care of. Make sure that things like issuing equipment, granting software licenses, giving access to internal systems, like the number of times you can ask your IT person, hey, make sure Jeremy gets XYZ things that are appropriate to his role. Have a checklist for each department. Like this is what this person needs. Do they actually have it? So that, you know, then the employee can just hit the ground running. Make sure all that hiring paperwork gets taken care of, a receipt of a handbook. And if you are going to do that remote onboarding, send them a gift card so they can eat lunch. You know, whether that's a delivery service, DoorDash, Uber Eats kind of thing, or in an ideal world, you know, ask them what their favorite place is, and send them a gift card for that.

Jeremy · 17:26

Yeah. No, I was just going to say, I like what you said about the, you know, not everyone, you know, even if you're doing group onboarding, it's like, well, some people, I was thinking, you know, you've got those people that ask tons of questions, right? And then you got those people that are like, no, I'm good, just get through what you need to get through and I'll figure it out, you know, like.

Jess · 17:48

Exactly.

Jeremy · 17:49

You don't want to have a two-hour call and you've got one person asking tons of questions, but everyone else was ready to go 20 minutes into it. So, right.

Jess · 17:57

And they're just checked out, they're texting their friends, they're posting on Instagram, and you're just like, that is time stamped. I can see literally that you're not paying attention to me.

Speaker 3 · 18:07

Like, yeah.

Jess · 18:08

So making it personalized like that really does, if you get somebody who is just like, I get it, I got it, I'm good to go, great. If you have the person who needs 100 questions, you've carved out time and space for them to feel comfortable asking those questions. Like, that's something that I say a lot on my show, is the only stupid question is the one that you don't ask. And by doing it one-on-one for a remote onboarding, that really lets people believe that you mean that.

Jeremy · 18:37

Yeah, yeah, that's good. And I've heard that you say that on your show a lot, and I love it because, you know, it's a lot better than the thing that my former youth pastor would say, where he'd say, there's no such thing as a dumb question, just dumb people that ask them. That's what he would say.

Jess · 18:56

Oh, that's terrible. That's terrible.

Jeremy · 18:59

And of course, he's joking, but still, it was...

Jess · 19:01

But not really.

Jeremy · 19:02

Right, right. But anyway, I love how you do that on your show. And then for those listening who aren't aware or haven't checked out Jess's show, it's Ask an Assistant Podcast. And you can find that on all the podcast platforms or you can go to askanassistant.com to check that out. It's definitely, I love the, you know, many of your episodes are short and to the point and topical and interesting. And so I like how you put it together. Definitely a different style from my show. And I think that's great.

Jess · 19:44

For sure. And that's where I was saying earlier that like there's a lot of overlap in terms of us both being executive assistants and creating content for executive assistants. But we're totally different people. We're doing totally different work, engaging with totally different people and topics. And I think that that's really valuable to have lots of different perspectives, providing thoughts and ideas for our listeners, for our fellow executive assistants.

Jeremy · 20:13

Awesome. Well, let's jump in into some more onboarding tips. What about, yeah, where do you want to go next? Where do you want to go next?

Jess · 20:22

Since all that last piece was about like remote onboarding, like if you really just don't have the budget, don't have the time, don't have a physical office space to do an in-person onboarding. That was all that last section. I think there are pieces of that that can be applied to an in-office situation. But I really did after, I don't know, a few months of trying to do remote onboarding, I really advocated for and convinced leadership to fly everybody out. So, I really am passionate about a great in-person onboarding experience. And I think a lot of our listeners, a lot of our fellow EAs still do have and go to physical office spaces. And certainly from the questions that I've seen in The Leader Assistant circle space, there's a couple of Facebook groups that I'm a part of. There is a subreddit. There are definitely questions about, hey, I know I'm the EA to the Director of Finance, but somehow I got roped into helping with onboarding. You just never know who's going to get asked to have a hand in the onboarding process. And I'm super, super passionate about people having a good onboarding experience when they're coming to a physical office. So that's where I would love to go.

Jeremy · 21:37

Yeah, let's do it.

Jess · 21:39

I love it. So, get everybody, fly them in. I don't care where they're from. Give them the option. So like when I was working at the company is Anna Plan, it's on my LinkedIn page. You can check it out. We had two main offices in the United States, one in San Francisco, one in Minneapolis. And so we would just give people the option, where do you want to go? You know, a fair few people chose San Francisco. Obviously, I would have chosen to go to San Francisco if I'd been given the option. But plenty of people still opted. You know, anybody who was, like, Montana and East would come to Minneapolis. You know, it just depended on flight availability. Maybe their sister lives in Minneapolis, and they're going to meet her for dinner after they get a free flight on this company's dime, like whatever. But yeah, fly everybody in. They get FaceTime with their fellow team members. They get FaceTime with you as the person who is doing the onboarding, whether you're an executive assistant, an HR person, an office manager, whatever it is that your role is. The biggest piece was hands-on IT walkthroughs. Like, I touched on this earlier, but the number of people that came, and these were people like in their 40s, 50s, sometimes 60s, who were coming into our office for onboarding. And they'd say they'd like hand me a closed MacBook and be like, I don't know what, is this my paperweight? Like, where's my computer? And I was just like, you have got to be kidding me. And then a friend of mine pulled me aside, and she's like, Jess, these people have been working at IBM for like 30 years. They've never touched a MacBook.

Jeremy · 23:18

Yeah.

Jess · 23:19

Like, have a little perspective. And I'm like, thank you for giving me the perspective, because it's just I had been so long without a PC that the MacBook felt very natural. But there are some things like on a MacBook, the mouse default scrolls backwards from a PC, or like it's command the instead of control Z for the shortcut. You know, so there are just little things that are a little bit different. And by gaining that perspective, I was able to then give a better, less sassy, less snarky in my own head onboarding experience to these people like, hey, I'm meeting you where you're at. You know, this is where you're at. I'm going to give you, I even learned more, like took a session at the Genius Bar. Like, how would you train somebody who's never touched a Mac before? How would you do that? And then I was able to give a better in-office experience to our people coming from other companies.

Jeremy · 24:18

Yeah, I actually onboarded my father-in-law to a Mac recently. And it was like, where's the backspace key? And I'm like, well, about that.

Jess · 24:29

It's just a little bit different, right? And they're critical, crucial differences.

Jeremy · 24:34

Yeah, he loves it, though. He's like, he had a really old, I don't know, Dell Windows laptop or something. One of the keys was falling apart. And he keeps saying, man, this computer is awesome. As soon as I click something, something happens.

Jess · 24:48

It just works, right? Did he have one of those... Do you remember the computers that have the little red mouse dot in the middle of the keyboard?

Jeremy · 24:55

Yeah, I think his latest one didn't. But I think the one before that definitely did have that.

Jess · 25:00

I remember that from early laptops and still existing. I think Lenovo still does that. Probably, yeah. But yeah, like if you're making that transition, like just noticing trends in the people that come through your office and being able to then learn from it yourself and educate yourself and to be able to give people a warm, welcoming onboarding is just so important. Yeah. You can definitely develop a relationship with the hotel that is closest to your office. You don't need people like, forget your Marriott points, forget your Radisson rewards, whatever it is. You're going to be at the hotel that is around the corner from the office, and you're going to deal with it. It's one night, you can live, and it's a company-sponsored thing.

Jeremy · 25:45

Right.

Jess · 25:46

Just have everybody as close to the office as possible so they can walk, then there's no, oh, I couldn't figure out the trains, oh, my taxi got stuck in traffic. Like, no, you're right here. I can come get you if you're not at the onboarding. Right. Exactly. Again, just like the remote onboarding, set it not too early and try not to do it on a Monday if you can help it. Like, Monday is when everything goes wrong, and just having it on a Tuesday, Wednesday, Thursday just makes it less stressful for you as the person providing the onboarding. Making it not too early is a big thing, too, just because you will have people coming from other time zones. And for you personally, if you get into the office at 8, and your new hires are ready at 8.30, you haven't had time to whatever it is you need to do. Check emails, deal with voicemails, deal with vendors who have shown up unexpectedly, print your onboarding packets. Like, whatever it is that you need to do, giving yourself, like, a two-hour buffer, I found to be invaluable. I would always feed new hires breakfast in the office, because we had a company culture of breakfast once, actually every day, not just once a week. We would do hot breakfast once a week and then like cold breakfast. So like bagels, yogurt, whatever. But like we always had groceries stocked. And I would make sure that hot breakfast was the day that we had new hires in the office, which we always did every week, even if it was just one person. Feed and breakfast, that gives you some loose, natural ice breaking networking time with people that are there. Take everybody out to lunch as a good break. Just kind of break up your day of all the procedural onboarding stuff that needs to happen. And then definitely schedule if they have team members that are local, make sure that the highest ranking person in that department is available to take them out to dinner.

Jeremy · 27:47

Yeah.

Jess · 27:49

Yeah. And definitely leading in to the onboarding. I developed and continued to update as things would present themselves. Like the Mac was a great example of this. Just a message with, hey, welcome to the team. Hey Jeremy, we're so excited to onboard you. Here's the office address. Here's what you can expect. Here's what the dress code looks like. We'll feed you breakfast and lunch. We're going to give you whatever kind of computer. Here's some resources that maybe you could look at before you get here, if that makes you feel more comfortable. We're going to do some onboarding paperwork. Here's the documentation you need to bring. I've definitely run into situations where people did not provide that documentation in time, and we had to resend job offers. This is important stuff to cover, but just making it as warm and approachable as possible is so important.

Jeremy · 28:44

Love it. Awesome. Well, what about the first couple of weeks? Let's say you're done with the onboarding week or the onboarding, the formal onboarding. What is the, excuse me, what is the, maybe a few tips for what to do that first 30 days? The ping pong back and forth game of manually scheduling meetings is unnecessary and inefficient in today's automated world. It's time to embrace calendar automation for increased productivity and capacity. You Can Book Me by Capacity is my favorite automated booking solution. It's a game changer for me and my executive. You can manage scheduling for your entire executive team, send automated reminders, add buffer time between appointments, and much more. You Can Book Me integrates with your existing Microsoft and Google calendars, so you can add automation without disrupting your current workflow. Go to leaderassistant.com/calendar to learn more and sign up for a free trial of this powerful scheduling automation tool. That's leaderassistant.com/calendar.

Jess · 30:19

The first 30 days, it's definitely going to depend by department. It's going to depend on what your company even does. So definitely checking in with, like in my role as the office manager, setting the tone for that first day was really important, and then turning them loose to their team. But always making myself available as a resource. Like you have questions, you come to me. Like I will help you find the answer, no matter how big or how small of a question. You can definitely get some information from the different departments and say, okay, what are the 30 day, like are there goals that need to be hit? Are there certain skills that should be accomplished by then? Especially if your company has any kind of internal learning management system, like an LMS, like a place where employees can engage with that material, and get to know the company inside and out. As the person who provides the onboarding, I think it's really important to just touch base with folks. So if you have everybody in to onboard, let's say on a Tuesday, on Friday, after they've had their first whirlwind week with the company, and they've gone home, and they're getting to know all of their information, all of their computer, all their new systems and passwords and whatever, just touch base, like, hey, how's it going? Like, here's my calendar link, I would love it if you booked a time with me, if you have any further questions now that you've had some time to digest everything. And then just like once a week or once every other week as the person who provided the onboarding, just touching back in, because again, it's going to depend so much based on the person's role based on their department. But just being that person who can find answers for them is such an invaluable resource to any employee at any level. And just making yourself available, showing people that you're still available, you haven't forgotten about them. It's not like a one day deal where you get to know Jess, you get to know whoever it is that's doing the onboarding, and then they just disappear. Like, no, I'm still here. And if you have random questions as they come up, that which everybody will, doesn't matter how big or how small, like everybody's going to have something come up and just making them know that you are available as that resource is so important.

Jeremy · 32:46

Yeah. I like to, I kind of have a philosophy of like very hands-on that first couple weeks, you know, and like guiding them through everything, super hands-on. And then over time, you just kind of get a little bit, you kind of remove those hands so that they are able to kind of be free to figure things out. But what I've seen on the flip side, what I've seen done poorly in the past is, you know, people that just throw throw them into the deep end. And they're like, all right, well, here's your stuff and let me know if you need anything, you know, and have fun swimming, like, right.

Jess · 33:29

I took your water wings away and I haven't taught you how to even do a doggy paddle, but good luck holding your computer above the water and not drowning.

Jeremy · 33:36

Exactly. Yeah.

Jess · 33:38

I love that you mentioned hands on. That was something that I was super passionate about too, is making sure that I walked everybody through how to do a lot of office things and building things that at the time people would be like, why are you teaching me how to use the service elevator? I'm like, okay, well, let me tell you why, because someday you're going to move a big piece of furniture into the office. What if I'm not here and you need to know how to use this elevator? I would teach people how to use the coffee machine because it was like, we called it the coffee robot and it had milk powders and coffee grounds and whatever, and in a busy office where people were literally drinking triple espressos all day long. I have no idea how these people didn't just explode from caffeine consumption. But teaching people, hey, when there's a little error message, you don't need to come find me to empty the grounds. You need to know the two buttons to press to empty the grounds yourself. So just walking people through and just being very like, this is your space, this is your office, whether you work here five days a week, whether you're remote and you come in a couple days a month, you need to know how to do this stuff. It's really important to be proud of the space and invested in keeping it nice and knowing how to use all of the really nice equipment. I mean, again, breakfast, five days a week, coffee robot. We had such nice stuff at this company and making sure that everybody knew how to do everything. Honestly, that elevator, our building put the main elevator that was right outside of our front door out of commission for three months because they were doing elevator maintenance. They needed to do a major upgrade. Everybody was so glad. They're just like for weeks, people were like, Jess, I'm so glad you taught me how to use that service elevator. I'm so sorry that I was salty about it when we were doing onboarding, but it was such a good skill and I'm like, that's right. It was a good skill.

Jeremy · 35:36

There's always something to do with the elevator. I'll tell you what, keep that office with an elevator. I think it was one of my... The office in St. Louis that Capacity is headquartered out of is actually the same office that my CEO's former company, answers.com, was headquartered out of. He's used that same office for a long time. He had a couple stories where somebody had gotten stuck in the elevator. He's like, I like to take the stairs. I take the stairs, get my steps in, but also because I don't want to get stuck in the elevator.

Jess · 36:12

Yes, and even just teaching people where the stairs are.

Jeremy · 36:15

Right.

Jess · 36:16

So they're not wandering into random doors or. Yeah, just like being very hands on, teaching people all the little nuances of things that maybe seem irrelevant or too much in the moment. Just all of that, I think, is very empowering to people. And again, just instills pride and ownership and good. It's just good. It's good to be involved. It's good to know how things work. And when I need to take time off, everybody needs to know how to operate the coffee robot. Okay. I'm not coming in. I'm out of town. I'm not coming in to fix the coffee robot.

Jeremy · 36:54

Yeah. And I think I think about this with my son, who my younger son, who is very Silas. He's very nervous or hesitant to want to do something that is new or go to like, let's say he joins a new basketball team and he doesn't know the players. He doesn't know the coach. He doesn't know the practice facility. And it's like it's really hard for him to be excited about it. He's I don't want to do that. I don't want to do that. But, you know, we get once we get him there and get him familiar with, okay, he wants to get there early because he wants to know where's the gym? Which door do we go through? Where do we park? You know, he wants to know all that stuff. And there's people like that in the professional world too, that this eases a lot of that anxiety of starting a new job and making them comfortable with their surroundings and familiar with how things work and yeah, how to use the coffee machine and whatnot. And it can make them more...

Jess · 37:52

The bathrooms are.

Jeremy · 37:54

Yeah.

Jess · 37:54

You know, just like all those little things that, yeah, just give you the lay of the land and help you feel at home, at ease. Like that's a really important piece of it too.

Jeremy · 38:06

Yeah. Well, let's transition to a couple of tips for onboarding executives. And maybe, you know, it's up to you as far as how much you want to go into each. But I'm wondering if maybe you have a tip for onboarding an executive who is, you know, new to you, but maybe not new to having an assistant. And then maybe also a tip for an executive who's new to have any assistant.

Jess · 38:36

Yeah, for sure. Definitely when you are established in your career and you are coming to an executive who is established in their career as well, there is a decent chance that you may be filling in, well, rather taking over, you know, a role of someone who has left the company for whatever reason. In an ideal world, hopefully that person has left you some kind of manual of some sort, if you're lucky. That was definitely my last formal EA in an office job was I got handed the most beautiful, like just had the smallest, tiniest, most detailed information in it and it was incredible. If at all possible, get time with that outgoing assistant and get the inside scoop from them. Every executive is so different. Every executive assistant is so different. We all come from different backgrounds. We all come from different education experiences. We all come from, like for me personally, I haven't worked in an office for over 10 years. I would have a steep learning curve coming back into an office, and I would need a lot of information from the outgoing person. That's not always the case. Maybe the person has already moved on to a new role. Maybe they moved state and they're just not available. Maybe your company doesn't have the budget to hire them to give you training time. Whatever the case may be, if you can get that training time with the outgoing assistant at all possible, jump at that opportunity. Because even if that person only worked with your executive for six months, that's still six months worth of experience that you are then getting some intel on. Maybe they worked with that executive for 10 years, and now you're going to get 10 years worth of quirks and information and facts and opinions and definitely still maintain discretion and decorum. You're not here to like gossip or anything. But my last in-office executive, he really liked a, it was like a stadium cup. Like you go to a baseball game and you get the big cup that your soda comes in, and he had an entire cupboard full of these cups. And every day for lunch, he wanted the stadium cup overfilled with ice. I'm talking like a dome of ice on top of it. Like as much as you could get loaded into the cup without it falling off as you would walk it over to him. He wanted that. He wanted one can of, I don't remember what soda it is off the top of my head, because this has been over 10 years since I worked with them. But he would want the one can of soda and then the crazy cup of ice with his lunch every day. Because the paperwork, the manual that I got said a full and full was bolded and underlined. The outgoing person was just like, no, you don't understand full, overflowing but still manageable to get it into the room. Just little details like that are really helpful to get from an outgoing person. That's my biggest tip as a seasoned executive assistant coming into a role with a seasoned executive, if you will, is to just get that training time if at all possible. If it's not possible to get that training time, making sure that your executive prioritizes giving you as much time as you need when you first start, and being honest with you. Giving you honest, here's how I like to communicate. I as the executive, I like to communicate by text, but I will not answer if you call. I like to DM on Slack, but I will not respond to a text message because my text messages are just a nightmare. Getting little nuance, things like that, and that's not little when you're communicating with your executive. If you're like, well, I thought that they would really respond to a phone call, but they never answer, and then you're sitting there feeling stressed, and work isn't getting done because you can't get ahold of your executive. So like making sure that they prioritize time to give you taking that time, and getting and documenting those honest answers. And if you were the executive assistant coming in with someone who has never had an EA before, which was definitely my experience with my present executive, he'd been just kind of winging it before we started working together. Like he'd had a couple of VAs through the Philippines, so this would have been like 2010 to 2013. And he just from his mastermind, they were like, you need an executive assistant. Like you need somebody who can make and answer phone calls. You need somebody who has the connecting the dots skills that an executive assistant has. Somebody who's going to notice things and help you go further. And I just happened to luck out, be his one interview for the role, and 10 years later, we're still going strong. We're just shy of 11 years now, actually, it'll be 11 years in March of 2025. And coming to that, just being open is really important because a lot of times if you do come from academia or a big corporate background, or maybe you've only ever been in an office and this is your first remote role, be very open and very flexible. This is a great opportunity for you and your executive. You're coming at this with a totally clean slate of an executive. They don't know what they need help with. Just being very honest with, these are the things that I can take off your plate. These are the things that I should take off your plate. You should no longer be booking your own travel. You should no longer be checking your own email. These are the things like you, executive person, you should be doing podcast interviews, you should be recording YouTube videos, you should be doing the things that make money, like hard money, and my support allows you to continue to do that. But just being very open and just kind of forgetting, like keep the skills with you, but kind of forget the structure of what you came from, because you're building a totally new structure with your executive who's never had an EA before.

Jeremy · 45:13

Yeah, and I think I kind of would combine the two where if the executives had an assistant, you mentioned trying to interview the former assistant, but if you can't, try to spend a lot of time with the executive and just kind of getting all of that information out of them so that you know what the preferences are, and how they like to work, and how they like their schedule, and so on. Then with the executive that hasn't had an assistant, you still need a lot of that time, but I found that you're more almost guiding them with that time, versus just kind of getting the download of, here's how you like things to happen. You're kind of more saying, hey, here's how I've done things in the past. How does this sound to you? Here's how I do calendar management. Here's how I've done email management. Here's how assistants around the world typically do this process. How does that sound to you kind of a thing?

Jess · 46:19

That was definitely something. My present executive was very generous with his time, and we moved very quickly from meeting several times a week for like an hour at a time, like three to five days a week. We were meeting for 60 plus minutes, and then a few weeks later, it was three days a week for 60 or less, and then a few weeks later, it was twice a week for 30 minutes, and now 10 years in, it's once a week for 15 to 30 minutes depending on what's going on.

Jeremy · 46:49

Yeah.

Jess · 46:50

Then we're in constant communication throughout any given day, throughout the week, but just that actual concentrated, these are the things that I need his eyes and ears on once a week.

Jeremy · 47:04

Yeah. Awesome. Well, this has been great. Lots of great onboarding tips. And is there any like kind of last thing you wanted to say or thing you want to make sure that you communicated to the assistance of the world today about the topic of onboarding?

Jess · 47:22

When it comes to onboarding, just I know I've said this a few times, but like keep it warm, make yourself as approachable as possible. And especially if you do work in a company where potentially the person that is responsible for the onboarding is not warm and approachable. Find a diplomatic way to find the right person for that role. Like I've definitely worked in companies where there are career HR people who have been in the role for 30 plus years and just do things the way that they do things. And, you know, first impressions really matter, especially when you're bringing people in to, you know, it's an exciting time to be starting a new job. People are excited because they got a new role that is bumping them up in job title or responsibility or salary or a new location that they're really excited about. Like, make sure that the person who is providing the onboarding experience at your company is warm and friendly and approachable and providing safe space for people to ask and get their questions answered.

Jeremy · 48:34

Love it. Well said, Jess. Thank you so much again for sharing your tips. We're excited to highlight Ask an Assistant episodes on The Leader Assistant Podcast this year and for those listening, stay tuned for some clips and spotlight episodes of Jess's conversations with or answers to questions that people have submitted for her show. And I'm excited to highlight your show on my show.

Jess · 49:07

Thank you so much for having me back. I'm really excited to be part of The Leader Assistant's sphere this year and in perpetuity.

Jeremy · 49:14

Awesome. What's the best place for people to reach out if they want to connect with you or listen to the show or all the things?

Jess · 49:23

The best place to find me is askanassistant.com. That is where you can ask your questions, you can listen to the show. I love to hear from any and or all of you. I don't have a show without folks that are asking questions. No question too big or too small, no problem too large to untangle. Again, the only, and I do mean only, stupid question is the one that you don't ask.

Jeremy · 49:52

Love it. Well, thanks again for listening, everyone. And you can check out the show notes and yeah, again, stay tuned for future conversations and future clips from Jess and Ask an Assistant Podcast, but you can check out the show notes at leaderassistant.com/313, and we'll talk to you next time.

Speaker 3 · 50:22

Please review on Apple Podcasts. gobullos.com.

Jeremy · 50:37

Hey, friends, my best-selling book, The Leader Assistant, has a companion study and discussion guide to go along with it. It's called The Leader Assistant Workbook. Now you can buy the Kindle ebook version of The Leader Assistant Workbook on Amazon, or you can go to leaderassistantbook.com and get a printable PDF version of the workbook. This version has all the space and margin in between the questions that you can write your own answers and take notes with. So it's a great way to print it out and keep track of your discussion and study guide notes. Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.