Jess Lindgren has worked in the C-Suite of organizations great and small for 20+ years. She is also host of the Ask an Assistant podcast.
In this episode of The Leader Assistant Podcast, Jess shares tips and tricks for onboarding executives, team members, as well as the nuances between onboarding executives who have never had an assistant versus executives who have had assistants.
LEADERSHIP QUOTE
People like us do things like this.
– Seth Godin
CONNECT WITH JESS
ABOUT JESS
Jess Lindgren has worked in the C-Suite of organizations great and small for 20+ years. She focuses on supporting her current CEO in his many endeavors, improving the relationships between EAs and their Execs, and has very low tolerance for any meeting that should have been an email. Jess hosts the wildly popular* business podcast, Ask An Assistant.
*in her Grandma’s sewing room
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EPISODE TRANSCRIPT
00:00:00.500 –> 00:00:03.220
JEREMY: Person meeting planning can be a lot to manage.
00:00:03.220 –> 00:00:05.940
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00:00:05.940 –> 00:00:10.560
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00:00:10.560 –> 00:00:19.640
JEREMY: Whether you’re organizing an executive offsite, department meeting, or team retreat, Troupe keeps it simple, fast, and organized.
00:00:19.640 –> 00:00:34.480
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00:00:34.480 –> 00:00:41.140
JEREMY: Troupe has an exclusive offer for Leader Assistant listeners through Administrative Professionals Day, so don’t miss out.
00:00:41.200 –> 00:00:46.180
JEREMY: Visit leaderassistant.com/troupe to learn more.
00:00:46.180 –> 00:00:53.780
JESS: Hi there, I’m Jess Lindgren, and today’s leadership quote comes from Seth Godin, who says, People like us do things like this.
00:01:00.438 –> 00:01:08.038
<v SPEAKER_3>The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.
00:01:17.457 –> 00:01:27.197
JEREMY: 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.
00:01:27.197 –> 00:01:29.897
JEREMY: It’s called The Leader Assistant Workbook.
00:01:29.897 –> 00:01:43.457
JEREMY: 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.
00:01:43.457 –> 00:01:52.097
JEREMY: This version has all the space and margin in between the questions that you can write your own answers and take notes with.
00:01:52.097 –> 00:01:59.537
JEREMY: So it’s a great way to print it out and keep track of your discussion and study guide notes.
00:01:59.537 –> 00:02:06.877
JEREMY: Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.
00:02:06.877 –> 00:02:09.117
JEREMY: Hey, friends, welcome to The Leader Assistant Podcast.
00:02:09.117 –> 00:02:13.137
JEREMY: It’s your host, Jeremy Burrows, and this is episode 313.
00:02:14.077 –> 00:02:33.037
JEREMY: 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.
00:02:33.037 –> 00:02:35.217
JEREMY: Jess, welcome back to the show.
00:02:35.217 –> 00:02:35.717
JESS: Thank you.
00:02:35.717 –> 00:02:39.257
JESS: It’s so great to be here all these years and episodes later.
00:02:40.037 –> 00:02:40.337
JEREMY: Yeah.
00:02:40.337 –> 00:02:52.297
JEREMY: So for those of you who happen to miss our first conversation, Episode 23, yes, Episode 23 was published back in 2019, I believe.
00:02:52.297 –> 00:02:56.257
JEREMY: And you can check out that conversation at leaderassistant.com/23.
00:02:58.277 –> 00:03:02.617
JEREMY: And yeah, a lot has changed since then, Jess.
00:03:02.617 –> 00:03:04.257
JEREMY: This is Episode 313.
00:03:04.257 –> 00:03:08.717
JEREMY: So literally hundreds of episodes, hundreds of interviews I’ve had since then.
00:03:10.137 –> 00:03:23.977
JEREMY: 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.
00:03:23.977 –> 00:03:26.357
JEREMY: But first, why don’t you catch us up?
00:03:26.357 –> 00:03:34.797
JEREMY: I know, you know, you’ve maybe relocated and have some changes in your life since 2019.
00:03:34.797 –> 00:03:41.377
JEREMY: So tell us a little bit about where you’re living and what projects you’re working on and all that fun stuff.
00:03:41.377 –> 00:03:42.697
JESS: Yeah, I do.
00:03:42.697 –> 00:03:48.777
JESS: So since 2019, I think life has changed for a lot, if not all of us, quite a bit.
00:03:48.777 –> 00:03:53.837
JESS: Back at episode 23, I was newly living in San Diego.
00:03:53.837 –> 00:03:58.337
JESS: I’d been there, I think just shy of or just after a year.
00:03:58.337 –> 00:04:04.317
JESS: And then obviously 2020 hit the pandemic and the longer things drug on.
00:04:04.317 –> 00:04:14.417
JESS: 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.
00:04:14.417 –> 00:04:18.737
JESS: You want to think about moving up there, like seems like a great time to make a real estate purchase.
00:04:18.737 –> 00:04:28.457
JESS: 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.
00:04:28.457 –> 00:04:36.457
JESS: So we did, we ended up buying a house site unseen over FaceTime during the depths of the pandemic.
00:04:36.577 –> 00:04:49.597
JESS: 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.
00:04:49.597 –> 00:05:02.177
JESS: 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.
00:05:02.177 –> 00:05:05.117
JESS: And yeah, we call it an overcorrection.
00:05:05.217 –> 00:05:17.937
JESS: 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.
00:05:17.937 –> 00:05:18.777
JEREMY: Wow.
00:05:18.777 –> 00:05:20.257
JEREMY: That’s a little bit of a change.
00:05:20.257 –> 00:05:20.977
JEREMY: I’m sure the cats are happy.
00:05:20.977 –> 00:05:22.837
JESS: So for just two people, the cats love it.
00:05:22.837 –> 00:05:24.297
JESS: They absolutely love it.
00:05:24.297 –> 00:05:26.117
JESS: But it’s a lot.
00:05:26.117 –> 00:05:32.337
JESS: There are definitely rooms where we don’t set foot for days on end, sometimes weeks, and it’s like, whoa, the sitting room.
00:05:32.337 –> 00:05:33.317
JESS: I haven’t been here in ages.
00:05:35.097 –> 00:05:47.017
JESS: 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.
00:05:47.017 –> 00:05:48.977
JESS: It’s just been really great to be part of their lives.
00:05:48.977 –> 00:05:51.437
JESS: We call ourselves professional auntie and uncle.
00:05:51.437 –> 00:05:54.357
JESS: We’re involved on the PTA.
00:05:54.357 –> 00:05:58.497
JESS: I always have to think about that because it’s not PTO, because that’s time off from work.
00:05:58.497 –> 00:05:59.077
JESS: PTA.
00:05:59.077 –> 00:06:07.637
JESS: 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.
00:06:07.637 –> 00:06:16.017
JESS: We go to everybody’s plays and concerts and dance recitals and also the neighborhood, auntie and uncle.
00:06:16.017 –> 00:06:16.657
JESS: It’s great.
00:06:16.657 –> 00:06:20.557
JESS: It’s really great and just so much flexibility in my work life.
00:06:20.557 –> 00:06:22.197
JESS: Finally have Ask an Assistant.
00:06:22.197 –> 00:06:27.837
JESS: Some of you may know me from the show and if you do, I thank you so much for listening.
00:06:27.837 –> 00:06:37.357
JESS: There’s a lot of overlap between Jeremy and I in terms of being executive assistants who create for executive assistants.
00:06:37.357 –> 00:06:41.877
JESS: I just appreciate every single person who takes the time to listen.
00:06:41.877 –> 00:06:45.037
JESS: On top of that, my executive has made a big pivot.
00:06:45.037 –> 00:06:51.437
JESS: He still definitely does a lot with online business and that realm of things.
00:06:51.437 –> 00:06:56.537
JESS: But he, during the pandemic, got a new hobby of collecting Pokemon cards.
00:06:57.217 –> 00:07:04.337
JESS: And now we have a very large, it’s 1.2 million and growing subscribers for the main channel.
00:07:04.337 –> 00:07:08.857
JESS: And he’s coming up on a million subscribers for his secondary Pokemon channel.
00:07:08.857 –> 00:07:13.037
JESS: And we run Pokemon card events in 2025.
00:07:13.037 –> 00:07:15.557
JESS: It’ll be one East Coast, one West Coast.
00:07:15.557 –> 00:07:18.457
JESS: And it’s just some of the best, most impactful work we’ve ever done.
00:07:18.457 –> 00:07:20.257
JESS: And it’s so much fun.
00:07:20.257 –> 00:07:22.417
JEREMY: Wow, that’s amazing.
00:07:22.417 –> 00:07:22.937
JEREMY: That’s amazing.
00:07:22.937 –> 00:07:28.797
JEREMY: We’ll have to do another episode on YouTube channels, maybe someday, because that’s pretty impressive.
00:07:29.957 –> 00:07:30.357
JEREMY: Awesome.
00:07:30.357 –> 00:07:33.597
JEREMY: Well, that is super exciting.
00:07:33.597 –> 00:07:36.177
JEREMY: And, you know, we have a similar story.
00:07:36.177 –> 00:07:41.657
JEREMY: I was starting to think about back to where I was, and even in in 2019.
00:07:41.657 –> 00:07:43.617
JEREMY: And I was in St.
00:07:43.617 –> 00:07:47.997
JEREMY: Louis and I moved to Kansas City during the global pandemic.
00:07:47.997 –> 00:07:48.717
JEREMY: Similar to you.
00:07:48.717 –> 00:07:50.257
JEREMY: I bought a house.
00:07:50.257 –> 00:07:54.237
JEREMY: I think it was October, September, October-ish of 2020.
00:07:56.037 –> 00:07:57.637
JEREMY: And it was a fixer-upper.
00:07:57.637 –> 00:08:00.957
JEREMY: So we, you know, fixer-uppered it.
00:08:00.957 –> 00:08:04.917
JEREMY: And yeah, it was crazy times.
00:08:04.917 –> 00:08:09.937
JEREMY: But that’s been, I guess, four, five years ago now.
00:08:09.937 –> 00:08:20.857
JEREMY: So, yeah, it’s my kids are 11 and 13 and a joy and a pain all at the same time.
00:08:22.377 –> 00:08:23.537
JESS: And are they still great artists?
00:08:23.537 –> 00:08:30.317
JESS: Because after our first conversation, your kids sent me the cutest thank you cards with little kiddies drawn on them.
00:08:30.317 –> 00:08:31.617
JESS: They’re being on the show.
00:08:31.617 –> 00:08:37.497
JEREMY: Yeah, they it takes a little bit more work, especially the older my older son.
00:08:37.497 –> 00:08:44.117
JEREMY: It takes a little more convincing to get him to do art these days because he’s too cool, you know, but it happens.
00:08:44.117 –> 00:08:47.377
JEREMY: My younger son still still likes drawing and creating.
00:08:47.377 –> 00:08:48.177
JEREMY: So that’s awesome.
00:08:49.777 –> 00:08:50.017
JEREMY: Awesome.
00:08:50.017 –> 00:08:52.157
JEREMY: Well, let’s let’s dive in then to onboarding.
00:08:52.157 –> 00:08:56.877
JEREMY: So in the Leader Assistant community, we have those of you listening who aren’t on it.
00:08:56.877 –> 00:09:00.277
JEREMY: We have a free community on a platform called Circle.
00:09:00.277 –> 00:09:04.317
JEREMY: You can go to circle.leaderassistant.com and you can join our free forum.
00:09:04.317 –> 00:09:14.677
JEREMY: 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.
00:09:14.737 –> 00:09:18.977
JEREMY: What do you recommend that I do to onboard well?
00:09:18.977 –> 00:09:29.157
JEREMY: 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.
00:09:30.297 –> 00:09:39.297
JEREMY: 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.
00:09:39.297 –> 00:09:47.457
JEREMY: And so there’s a little bit of onboarding them on how to work with an assistant, utilize an assistant, etc.
00:09:47.457 –> 00:10:03.297
JEREMY: 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.
00:10:03.297 –> 00:10:14.517
JEREMY: 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.
00:10:14.517 –> 00:10:16.277
JESS: I love it so much.
00:10:16.277 –> 00:10:18.597
JESS: Yeah, I’ve actually been with my present executive.
00:10:18.597 –> 00:10:23.177
JESS: We just crossed 10 years this year of working together.
00:10:24.097 –> 00:10:26.177
JESS: We are a pretty small team.
00:10:26.177 –> 00:10:31.577
JESS: So Pat has two separate teams, several separate teams that he’s a part of, honestly.
00:10:31.577 –> 00:10:36.157
JESS: But the two major teams, one team is like eight people and one is two.
00:10:36.157 –> 00:10:37.557
JESS: It’s me and him.
00:10:37.557 –> 00:10:42.517
JESS: So from the backend bones of the structure of the business, it’s pretty tiny.
00:10:42.517 –> 00:10:48.677
JESS: But my role before working with him, I was working at a pretty hyper growth startup.
00:10:48.677 –> 00:10:57.837
JESS: We went from 200 to about 650 employees during my, I think just under two years working at the company.
00:10:57.837 –> 00:11:26.817
JESS: 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.
00:11:26.817 –> 00:11:27.777
JESS: I had never done it before.
00:11:27.777 –> 00:11:28.737
JESS: I was super nervous.
00:11:28.737 –> 00:11:35.717
JESS: 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.
00:11:35.837 –> 00:11:45.437
JESS: 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.
00:11:45.437 –> 00:11:48.477
JESS: I think the time is three days.
00:11:48.737 –> 00:11:56.217
JESS: You have three days to make sure that the documents are in their system and verified and good to go.
00:11:56.217 –> 00:12:05.817
JESS: 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.
00:12:05.817 –> 00:12:06.657
JEREMY: Nice.
00:12:06.657 –> 00:12:07.437
JEREMY: That’s awesome.
00:12:07.437 –> 00:12:09.977
JEREMY: And what, where do you want to start?
00:12:09.977 –> 00:12:14.577
JEREMY: What do you, do you want to start with like executive assistant onboarding?
00:12:14.577 –> 00:12:21.517
JEREMY: Do you want to start with, what’s, what’s, what’s maybe a process for an executive that you’re trying to onboard?
00:12:21.517 –> 00:12:23.637
JEREMY: How would you like to kick things off?
00:12:23.637 –> 00:12:36.277
JESS: 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.
00:12:36.277 –> 00:12:37.237
JEREMY: That sounds perfect.
00:12:37.237 –> 00:12:37.677
JEREMY: Let’s do it.
00:12:37.677 –> 00:12:39.057
JESS: Awesome.
00:12:39.057 –> 00:12:46.817
JESS: 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.
00:12:47.937 –> 00:12:55.617
JESS: 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.
00:12:55.617 –> 00:13:00.097
JESS: But I think a lot of this is very applicable to pretty much any situation.
00:13:01.437 –> 00:13:11.317
JESS: 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.
00:13:11.317 –> 00:13:16.897
JESS: Like, it is money well spent, it is well worth the investment to bring somebody.
00:13:16.897 –> 00:13:42.897
JESS: 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.
00:13:42.897 –> 00:13:47.017
JESS: They might have an iPhone, but they’ve never touched a MacBook before.
00:13:47.017 –> 00:14:02.557
JESS: 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.
00:14:02.557 –> 00:14:05.997
JESS: It is so worth it to have people in person.
00:14:05.997 –> 00:14:16.677
JESS: 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.
00:14:16.677 –> 00:14:23.857
JESS: If you really have to do remote onboarding, like I see people asking all the time, what are some fun onboarding activities?
00:14:23.857 –> 00:14:32.877
JESS: 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.
00:14:32.877 –> 00:14:35.777
JESS: Like it’s, it’s a formal process.
00:14:35.777 –> 00:14:39.077
JESS: Like you can certainly make it warm.
00:14:39.077 –> 00:14:40.897
JESS: You can certainly make it engaging.
00:14:40.897 –> 00:14:46.297
JESS: But if you are going to stick with remote, you want it to be short.
00:14:46.297 –> 00:14:54.937
JESS: 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.
00:14:55.097 –> 00:15:00.937
JESS: And I didn’t want to run the call, and the people on the call didn’t want to attend it.
00:15:00.937 –> 00:15:09.577
JESS: 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?
00:15:09.577 –> 00:15:12.257
JESS: Like, yes, it’s just not ideal.
00:15:12.257 –> 00:15:17.737
JESS: So if you are going to stick with remote onboarding, keep it short, keep it sweet, keep it engaging, but not gimmicky.
00:15:17.737 –> 00:15:20.057
JESS: Like you want a lot of involvement.
00:15:20.697 –> 00:15:27.157
JESS: You know, people learn best when there are hands-on activities, things that they can do themselves.
00:15:28.957 –> 00:15:39.177
JESS: 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.
00:15:39.177 –> 00:15:44.437
JESS: You know, if we had somebody in New York and somebody in California, you don’t want it to be 6 a.m.
00:15:44.437 –> 00:15:46.317
JESS: in California, 8 a.m.
00:15:46.317 –> 00:15:47.917
JESS: in Minnesota and 9 a.m.
00:15:47.917 –> 00:15:48.577
JESS: on the East Coast.
00:15:48.717 –> 00:15:54.257
JESS: Like, just pick a time that’s not too early in the day to do your remote onboarding.
00:15:54.257 –> 00:15:56.937
JESS: Do it one on one, if at all possible.
00:15:56.937 –> 00:16:01.957
JESS: Like just, it gives you the ability to give that person your full attention.
00:16:01.957 –> 00:16:08.297
JESS: It lets the employee feel comfortable asking questions no matter how big or how small.
00:16:08.297 –> 00:16:12.897
JESS: And yeah, it just, it will go faster.
00:16:12.897 –> 00:16:18.177
JESS: Because if you have a group of 2 to 10 people, you’re going to have some people who just run the gamut.
00:16:18.217 –> 00:16:21.377
JESS: You’re going to have people who have an attention span of 2 out of 10.
00:16:21.377 –> 00:16:27.177
JESS: 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.
00:16:27.177 –> 00:16:34.397
JESS: So like doing it one on one, if at all possible just is the best case scenario for everybody, I feel.
00:16:34.397 –> 00:16:38.357
JESS: Develop and maintain a checklist so that all of your bases are covered.
00:16:38.357 –> 00:16:42.377
JESS: Make sure the important HR stuff gets taken care of.
00:16:42.377 –> 00:16:57.417
JESS: 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.
00:16:57.417 –> 00:16:59.277
JESS: Have a checklist for each department.
00:16:59.277 –> 00:17:00.737
JESS: Like this is what this person needs.
00:17:00.737 –> 00:17:03.057
JESS: Do they actually have it?
00:17:03.057 –> 00:17:06.777
JESS: So that, you know, then the employee can just hit the ground running.
00:17:06.777 –> 00:17:11.797
JESS: Make sure all that hiring paperwork gets taken care of, a receipt of a handbook.
00:17:11.797 –> 00:17:16.537
JESS: And if you are going to do that remote onboarding, send them a gift card so they can eat lunch.
00:17:16.857 –> 00:17:26.157
JESS: 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.
00:17:26.157 –> 00:17:28.317
JEREMY: Yeah.
00:17:29.197 –> 00:17:41.897
JEREMY: 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?
00:17:41.897 –> 00:17:48.597
JEREMY: 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.
00:17:48.597 –> 00:17:49.457
JESS: Exactly.
00:17:49.457 –> 00:17:56.017
JEREMY: 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.
00:17:56.017 –> 00:17:57.377
JEREMY: So, right.
00:17:57.377 –> 00:18:04.397
JESS: 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.
00:18:04.397 –> 00:18:07.377
JESS: I can see literally that you’re not paying attention to me.
00:18:07.457 –> 00:18:08.937
<v SPEAKER_3>Like, yeah.
00:18:08.937 –> 00:18:16.357
JESS: 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.
00:18:16.357 –> 00:18:23.897
JESS: If you have the person who needs 100 questions, you’ve carved out time and space for them to feel comfortable asking those questions.
00:18:23.897 –> 00:18:29.437
JESS: 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.
00:18:29.437 –> 00:18:37.697
JESS: And by doing it one-on-one for a remote onboarding, that really lets people believe that you mean that.
00:18:37.697 –> 00:18:40.117
JEREMY: Yeah, yeah, that’s good.
00:18:40.117 –> 00:18:55.377
JEREMY: 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.
00:18:55.377 –> 00:18:56.457
JEREMY: That’s what he would say.
00:18:56.457 –> 00:18:57.897
JESS: Oh, that’s terrible.
00:18:57.897 –> 00:18:58.977
JESS: That’s terrible.
00:18:59.037 –> 00:19:01.217
JEREMY: And of course, he’s joking, but still, it was…
00:19:01.297 –> 00:19:02.417
JESS: But not really.
00:19:02.417 –> 00:19:04.337
JEREMY: Right, right.
00:19:04.337 –> 00:19:06.417
JEREMY: But anyway, I love how you do that on your show.
00:19:06.417 –> 00:19:15.757
JEREMY: And then for those listening who aren’t aware or haven’t checked out Jess’s show, it’s Ask an Assistant Podcast.
00:19:15.757 –> 00:19:22.337
JEREMY: And you can find that on all the podcast platforms or you can go to askanassistant.com to check that out.
00:19:22.337 –> 00:19:35.517
JEREMY: It’s definitely, I love the, you know, many of your episodes are short and to the point and topical and interesting.
00:19:35.517 –> 00:19:37.157
JEREMY: And so I like how you put it together.
00:19:37.157 –> 00:19:43.137
JEREMY: Definitely a different style from my show.
00:19:43.137 –> 00:19:44.677
JEREMY: And I think that’s great.
00:19:44.677 –> 00:19:45.217
JESS: For sure.
00:19:45.217 –> 00:19:53.597
JESS: 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.
00:19:54.197 –> 00:19:56.337
JESS: But we’re totally different people.
00:19:56.337 –> 00:20:01.937
JESS: We’re doing totally different work, engaging with totally different people and topics.
00:20:01.937 –> 00:20:13.577
JESS: 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.
00:20:13.577 –> 00:20:13.917
JEREMY: Awesome.
00:20:13.917 –> 00:20:18.737
JEREMY: Well, let’s jump in into some more onboarding tips.
00:20:18.737 –> 00:20:20.977
JEREMY: What about, yeah, where do you want to go next?
00:20:20.977 –> 00:20:21.797
JEREMY: Where do you want to go next?
00:20:22.537 –> 00:20:32.597
JESS: 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.
00:20:33.817 –> 00:20:35.217
JESS: That was all that last section.
00:20:35.217 –> 00:20:40.477
JESS: I think there are pieces of that that can be applied to an in-office situation.
00:20:40.477 –> 00:20:50.297
JESS: 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.
00:20:51.397 –> 00:20:56.577
JESS: So, I really am passionate about a great in-person onboarding experience.
00:20:56.577 –> 00:21:04.597
JESS: And I think a lot of our listeners, a lot of our fellow EAs still do have and go to physical office spaces.
00:21:04.597 –> 00:21:12.237
JESS: 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.
00:21:12.237 –> 00:21:14.557
JESS: There is a subreddit.
00:21:14.777 –> 00:21:22.317
JESS: 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.
00:21:22.317 –> 00:21:27.797
JESS: You just never know who’s going to get asked to have a hand in the onboarding process.
00:21:27.797 –> 00:21:35.757
JESS: And I’m super, super passionate about people having a good onboarding experience when they’re coming to a physical office.
00:21:35.757 –> 00:21:37.817
JESS: So that’s where I would love to go.
00:21:37.817 –> 00:21:39.377
JEREMY: Yeah, let’s do it.
00:21:39.377 –> 00:21:39.877
JESS: I love it.
00:21:39.877 –> 00:21:42.957
JESS: So, get everybody, fly them in.
00:21:42.957 –> 00:21:43.977
JESS: I don’t care where they’re from.
00:21:44.557 –> 00:21:45.417
JESS: Give them the option.
00:21:45.417 –> 00:21:48.657
JESS: So like when I was working at the company is Anna Plan, it’s on my LinkedIn page.
00:21:48.657 –> 00:21:50.077
JESS: You can check it out.
00:21:50.077 –> 00:21:55.297
JESS: We had two main offices in the United States, one in San Francisco, one in Minneapolis.
00:21:55.297 –> 00:22:00.397
JESS: And so we would just give people the option, where do you want to go?
00:22:00.397 –> 00:22:02.397
JESS: You know, a fair few people chose San Francisco.
00:22:02.397 –> 00:22:07.017
JESS: Obviously, I would have chosen to go to San Francisco if I’d been given the option.
00:22:07.017 –> 00:22:08.877
JESS: But plenty of people still opted.
00:22:08.997 –> 00:22:16.057
JESS: You know, anybody who was, like, Montana and East would come to Minneapolis.
00:22:16.057 –> 00:22:19.657
JESS: You know, it just depended on flight availability.
00:22:19.657 –> 00:22:28.457
JESS: 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.
00:22:28.457 –> 00:22:31.277
JESS: But yeah, fly everybody in.
00:22:31.277 –> 00:22:35.037
JESS: They get FaceTime with their fellow team members.
00:22:35.037 –> 00:22:45.097
JESS: 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.
00:22:45.097 –> 00:22:49.357
JESS: The biggest piece was hands-on IT walkthroughs.
00:22:49.357 –> 00:23:01.517
JESS: 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.
00:23:01.517 –> 00:23:06.077
JESS: And they’d say they’d like hand me a closed MacBook and be like, I don’t know what, is this my paperweight?
00:23:06.317 –> 00:23:07.877
JESS: Like, where’s my computer?
00:23:07.877 –> 00:23:10.417
JESS: And I was just like, you have got to be kidding me.
00:23:10.417 –> 00:23:16.637
JESS: 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.
00:23:16.637 –> 00:23:18.837
JESS: They’ve never touched a MacBook.
00:23:18.837 –> 00:23:19.677
JEREMY: Yeah.
00:23:19.677 –> 00:23:21.657
JESS: Like, have a little perspective.
00:23:21.657 –> 00:23:31.517
JESS: 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.
00:23:31.517 –> 00:23:46.457
JESS: 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.
00:23:46.457 –> 00:23:49.697
JESS: You know, so there are just little things that are a little bit different.
00:23:49.697 –> 00:24:01.717
JESS: 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.
00:24:01.717 –> 00:24:02.997
JESS: You know, this is where you’re at.
00:24:02.997 –> 00:24:06.657
JESS: I’m going to give you, I even learned more, like took a session at the Genius Bar.
00:24:06.657 –> 00:24:10.937
JESS: Like, how would you train somebody who’s never touched a Mac before?
00:24:10.937 –> 00:24:12.497
JESS: How would you do that?
00:24:12.497 –> 00:24:18.757
JESS: And then I was able to give a better in-office experience to our people coming from other companies.
00:24:18.757 –> 00:24:22.417
JEREMY: Yeah, I actually onboarded my father-in-law to a Mac recently.
00:24:22.417 –> 00:24:25.377
JEREMY: And it was like, where’s the backspace key?
00:24:25.377 –> 00:24:27.817
JEREMY: And I’m like, well, about that.
00:24:29.517 –> 00:24:31.517
JESS: It’s just a little bit different, right?
00:24:31.517 –> 00:24:33.977
JESS: And they’re critical, crucial differences.
00:24:34.377 –> 00:24:35.497
JEREMY: Yeah, he loves it, though.
00:24:35.497 –> 00:24:40.677
JEREMY: He’s like, he had a really old, I don’t know, Dell Windows laptop or something.
00:24:40.677 –> 00:24:42.697
JEREMY: One of the keys was falling apart.
00:24:42.697 –> 00:24:45.677
JEREMY: And he keeps saying, man, this computer is awesome.
00:24:45.677 –> 00:24:48.397
JEREMY: As soon as I click something, something happens.
00:24:48.397 –> 00:24:49.497
JESS: It just works, right?
00:24:49.497 –> 00:24:51.437
JESS: Did he have one of those…
00:24:51.437 –> 00:24:55.157
JESS: Do you remember the computers that have the little red mouse dot in the middle of the keyboard?
00:24:55.157 –> 00:24:57.017
JEREMY: Yeah, I think his latest one didn’t.
00:24:57.017 –> 00:25:00.377
JEREMY: But I think the one before that definitely did have that.
00:25:00.377 –> 00:25:02.957
JESS: I remember that from early laptops and still existing.
00:25:03.017 –> 00:25:05.117
JESS: I think Lenovo still does that.
00:25:05.117 –> 00:25:06.357
JESS: Probably, yeah.
00:25:06.357 –> 00:25:24.117
JESS: 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.
00:25:24.177 –> 00:25:25.617
JESS: Yeah.
00:25:25.617 –> 00:25:31.337
JESS: You can definitely develop a relationship with the hotel that is closest to your office.
00:25:31.337 –> 00:25:36.977
JESS: You don’t need people like, forget your Marriott points, forget your Radisson rewards, whatever it is.
00:25:36.977 –> 00:25:40.817
JESS: You’re going to be at the hotel that is around the corner from the office, and you’re going to deal with it.
00:25:40.817 –> 00:25:44.617
JESS: It’s one night, you can live, and it’s a company-sponsored thing.
00:25:45.317 –> 00:25:46.157
JEREMY: Right.
00:25:46.157 –> 00:25:56.317
JESS: 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.
00:25:56.317 –> 00:25:57.897
JESS: Like, no, you’re right here.
00:25:57.897 –> 00:26:01.037
JESS: I can come get you if you’re not at the onboarding.
00:26:01.037 –> 00:26:01.437
JESS: Right.
00:26:01.437 –> 00:26:03.037
JESS: Exactly.
00:26:03.037 –> 00:26:09.477
JESS: 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.
00:26:09.477 –> 00:26:22.097
JESS: 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.
00:26:22.677 –> 00:26:29.377
JESS: Making it not too early is a big thing, too, just because you will have people coming from other time zones.
00:26:29.377 –> 00:26:39.857
JESS: 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.
00:26:39.857 –> 00:26:46.517
JESS: Check emails, deal with voicemails, deal with vendors who have shown up unexpectedly, print your onboarding packets.
00:26:46.517 –> 00:26:52.477
JESS: Like, whatever it is that you need to do, giving yourself, like, a two-hour buffer, I found to be invaluable.
00:26:54.837 –> 00:27:03.377
JESS: 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.
00:27:03.377 –> 00:27:07.157
JESS: We would do hot breakfast once a week and then like cold breakfast.
00:27:07.157 –> 00:27:08.937
JESS: So like bagels, yogurt, whatever.
00:27:08.937 –> 00:27:10.897
JESS: But like we always had groceries stocked.
00:27:10.897 –> 00:27:20.077
JESS: 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.
00:27:20.077 –> 00:27:27.337
JESS: Feed and breakfast, that gives you some loose, natural ice breaking networking time with people that are there.
00:27:27.337 –> 00:27:30.897
JESS: Take everybody out to lunch as a good break.
00:27:30.897 –> 00:27:38.217
JESS: Just kind of break up your day of all the procedural onboarding stuff that needs to happen.
00:27:38.217 –> 00:27:47.937
JESS: 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.
00:27:47.937 –> 00:27:49.117
JEREMY: Yeah.
00:27:49.117 –> 00:27:50.357
JESS: Yeah.
00:27:50.357 –> 00:27:52.777
JESS: And definitely leading in to the onboarding.
00:27:53.917 –> 00:27:58.677
JESS: I developed and continued to update as things would present themselves.
00:27:58.677 –> 00:28:01.577
JESS: Like the Mac was a great example of this.
00:28:01.577 –> 00:28:04.097
JESS: Just a message with, hey, welcome to the team.
00:28:04.097 –> 00:28:06.577
JESS: Hey Jeremy, we’re so excited to onboard you.
00:28:06.577 –> 00:28:08.277
JESS: Here’s the office address.
00:28:08.277 –> 00:28:09.517
JESS: Here’s what you can expect.
00:28:09.517 –> 00:28:12.037
JESS: Here’s what the dress code looks like.
00:28:12.037 –> 00:28:13.697
JESS: We’ll feed you breakfast and lunch.
00:28:14.237 –> 00:28:16.717
JESS: We’re going to give you whatever kind of computer.
00:28:16.717 –> 00:28:22.917
JESS: Here’s some resources that maybe you could look at before you get here, if that makes you feel more comfortable.
00:28:22.917 –> 00:28:24.637
JESS: We’re going to do some onboarding paperwork.
00:28:24.637 –> 00:28:27.117
JESS: Here’s the documentation you need to bring.
00:28:27.957 –> 00:28:36.237
JESS: I’ve definitely run into situations where people did not provide that documentation in time, and we had to resend job offers.
00:28:36.237 –> 00:28:44.877
JESS: This is important stuff to cover, but just making it as warm and approachable as possible is so important.
00:28:44.877 –> 00:28:47.037
JEREMY: Love it.
00:28:47.037 –> 00:28:47.417
JEREMY: Awesome.
00:28:47.417 –> 00:28:53.897
JEREMY: Well, what about the first couple of weeks?
00:28:53.897 –> 00:29:02.177
JEREMY: Let’s say you’re done with the onboarding week or the onboarding, the formal onboarding.
00:29:03.397 –> 00:29:13.837
JEREMY: What is the, excuse me, what is the, maybe a few tips for what to do that first 30 days?
00:29:19.379 –> 00:29:28.359
JEREMY: The ping pong back and forth game of manually scheduling meetings is unnecessary and inefficient in today’s automated world.
00:29:28.359 –> 00:29:34.579
JEREMY: It’s time to embrace calendar automation for increased productivity and capacity.
00:29:34.579 –> 00:29:39.839
JEREMY: You Can Book Me by Capacity is my favorite automated booking solution.
00:29:39.839 –> 00:29:43.259
JEREMY: It’s a game changer for me and my executive.
00:29:43.259 –> 00:29:52.739
JEREMY: You can manage scheduling for your entire executive team, send automated reminders, add buffer time between appointments, and much more.
00:29:52.739 –> 00:30:01.659
JEREMY: You Can Book Me integrates with your existing Microsoft and Google calendars, so you can add automation without disrupting your current workflow.
00:30:01.659 –> 00:30:10.939
JEREMY: Go to leaderassistant.com/calendar to learn more and sign up for a free trial of this powerful scheduling automation tool.
00:30:10.939 –> 00:30:12.319
JEREMY: That’s leaderassistant.com/calendar.
00:30:19.578 –> 00:30:25.158
JESS: The first 30 days, it’s definitely going to depend by department.
00:30:25.158 –> 00:30:28.458
JESS: It’s going to depend on what your company even does.
00:30:28.458 –> 00:30:41.698
JESS: 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.
00:30:41.698 –> 00:30:44.458
JESS: But always making myself available as a resource.
00:30:44.458 –> 00:30:46.718
JESS: Like you have questions, you come to me.
00:30:46.718 –> 00:30:52.178
JESS: Like I will help you find the answer, no matter how big or how small of a question.
00:30:52.178 –> 00:30:59.938
JESS: 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?
00:30:59.938 –> 00:31:07.138
JESS: Are there certain skills that should be accomplished by then?
00:31:07.138 –> 00:31:22.658
JESS: 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.
00:31:22.658 –> 00:31:28.838
JESS: As the person who provides the onboarding, I think it’s really important to just touch base with folks.
00:31:28.838 –> 00:31:46.458
JESS: 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?
00:31:46.558 –> 00:31:55.378
JESS: 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.
00:31:55.378 –> 00:32:07.258
JESS: 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.
00:32:07.258 –> 00:32:15.258
JESS: But just being that person who can find answers for them is such an invaluable resource to any employee at any level.
00:32:15.818 –> 00:32:22.118
JESS: And just making yourself available, showing people that you’re still available, you haven’t forgotten about them.
00:32:22.118 –> 00:32:28.738
JESS: 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.
00:32:28.738 –> 00:32:30.058
JESS: Like, no, I’m still here.
00:32:30.058 –> 00:32:46.378
JESS: 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.
00:32:46.378 –> 00:32:47.718
JEREMY: Yeah.
00:32:47.718 –> 00:33:00.758
JEREMY: 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.
00:33:00.758 –> 00:33:13.658
JEREMY: 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.
00:33:13.658 –> 00:33:22.958
JEREMY: 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.
00:33:22.958 –> 00:33:29.318
JEREMY: 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.
00:33:29.318 –> 00:33:36.798
JESS: 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.
00:33:36.798 –> 00:33:37.738
JEREMY: Exactly.
00:33:37.818 –> 00:33:38.958
JEREMY: Yeah.
00:33:38.958 –> 00:33:40.798
JESS: I love that you mentioned hands on.
00:33:40.798 –> 00:33:57.798
JESS: 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?
00:33:57.798 –> 00:34:05.838
JESS: 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.
00:34:05.838 –> 00:34:09.058
JESS: What if I’m not here and you need to know how to use this elevator?
00:34:09.058 –> 00:34:24.218
JESS: 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.
00:34:24.218 –> 00:34:28.778
JESS: I have no idea how these people didn’t just explode from caffeine consumption.
00:34:28.778 –> 00:34:36.818
JESS: But teaching people, hey, when there’s a little error message, you don’t need to come find me to empty the grounds.
00:34:36.818 –> 00:34:41.798
JESS: You need to know the two buttons to press to empty the grounds yourself.
00:34:41.798 –> 00:34:54.478
JESS: 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.
00:34:54.478 –> 00:35:02.098
JESS: 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.
00:35:02.098 –> 00:35:05.118
JESS: I mean, again, breakfast, five days a week, coffee robot.
00:35:05.118 –> 00:35:10.698
JESS: We had such nice stuff at this company and making sure that everybody knew how to do everything.
00:35:10.698 –> 00:35:20.658
JESS: 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.
00:35:20.758 –> 00:35:23.218
JESS: They needed to do a major upgrade.
00:35:23.218 –> 00:35:24.198
JESS: Everybody was so glad.
00:35:24.198 –> 00:35:29.398
JESS: They’re just like for weeks, people were like, Jess, I’m so glad you taught me how to use that service elevator.
00:35:29.398 –> 00:35:35.638
JESS: 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.
00:35:35.638 –> 00:35:36.758
JESS: It was a good skill.
00:35:36.758 –> 00:35:38.538
JEREMY: There’s always something to do with the elevator.
00:35:38.538 –> 00:35:41.318
JEREMY: I’ll tell you what, keep that office with an elevator.
00:35:44.658 –> 00:35:46.318
JEREMY: I think it was one of my…
00:35:46.318 –> 00:35:48.078
JEREMY: The office in St.
00:35:48.078 –> 00:35:58.278
JEREMY: Louis that Capacity is headquartered out of is actually the same office that my CEO’s former company, answers.com, was headquartered out of.
00:35:58.618 –> 00:36:01.438
JEREMY: He’s used that same office for a long time.
00:36:01.438 –> 00:36:05.238
JEREMY: He had a couple stories where somebody had gotten stuck in the elevator.
00:36:05.558 –> 00:36:07.218
JEREMY: He’s like, I like to take the stairs.
00:36:07.218 –> 00:36:12.278
JEREMY: I take the stairs, get my steps in, but also because I don’t want to get stuck in the elevator.
00:36:12.278 –> 00:36:15.438
JESS: Yes, and even just teaching people where the stairs are.
00:36:15.438 –> 00:36:16.198
JEREMY: Right.
00:36:16.198 –> 00:36:20.078
JESS: So they’re not wandering into random doors or.
00:36:20.078 –> 00:36:30.798
JESS: 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.
00:36:30.858 –> 00:36:34.958
JESS: Just all of that, I think, is very empowering to people.
00:36:34.958 –> 00:36:41.358
JESS: And again, just instills pride and ownership and good.
00:36:41.598 –> 00:36:42.418
JESS: It’s just good.
00:36:42.418 –> 00:36:43.398
JESS: It’s good to be involved.
00:36:43.398 –> 00:36:44.878
JESS: It’s good to know how things work.
00:36:44.878 –> 00:36:49.358
JESS: And when I need to take time off, everybody needs to know how to operate the coffee robot.
00:36:49.358 –> 00:36:50.038
JESS: Okay.
00:36:50.358 –> 00:36:51.038
JESS: I’m not coming in.
00:36:51.038 –> 00:36:51.738
JESS: I’m out of town.
00:36:51.738 –> 00:36:54.238
JESS: I’m not coming in to fix the coffee robot.
00:36:54.238 –> 00:36:54.538
JEREMY: Yeah.
00:36:54.538 –> 00:36:59.098
JEREMY: And I think I think about this with my son, who my younger son, who is very Silas.
00:36:59.218 –> 00:37:13.338
JEREMY: 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.
00:37:13.338 –> 00:37:14.258
JEREMY: He doesn’t know the coach.
00:37:14.258 –> 00:37:15.838
JEREMY: He doesn’t know the practice facility.
00:37:15.838 –> 00:37:20.138
JEREMY: And it’s like it’s really hard for him to be excited about it.
00:37:20.138 –> 00:37:20.938
JEREMY: He’s I don’t want to do that.
00:37:20.938 –> 00:37:22.218
JEREMY: I don’t want to do that.
00:37:22.218 –> 00:37:31.058
JEREMY: 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?
00:37:31.058 –> 00:37:32.398
JEREMY: Which door do we go through?
00:37:32.398 –> 00:37:33.338
JEREMY: Where do we park?
00:37:33.338 –> 00:37:34.478
JEREMY: You know, he wants to know all that stuff.
00:37:34.478 –> 00:37:51.818
JEREMY: 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.
00:37:51.818 –> 00:37:52.678
JEREMY: And it can make them more…
00:37:52.678 –> 00:37:54.058
JESS: The bathrooms are.
00:37:54.058 –> 00:37:54.598
JEREMY: Yeah.
00:37:54.598 –> 00:38:03.558
JESS: 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.
00:38:03.558 –> 00:38:06.098
JESS: Like that’s a really important piece of it too.
00:38:06.098 –> 00:38:07.298
JEREMY: Yeah.
00:38:07.298 –> 00:38:13.738
JEREMY: Well, let’s transition to a couple of tips for onboarding executives.
00:38:13.738 –> 00:38:18.378
JEREMY: And maybe, you know, it’s up to you as far as how much you want to go into each.
00:38:18.378 –> 00:38:30.298
JEREMY: 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.
00:38:30.298 –> 00:38:36.098
JEREMY: And then maybe also a tip for an executive who’s new to have any assistant.
00:38:36.098 –> 00:38:37.938
JESS: Yeah, for sure.
00:38:37.938 –> 00:39:02.538
JESS: 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.
00:39:02.538 –> 00:39:08.678
JESS: In an ideal world, hopefully that person has left you some kind of manual of some sort, if you’re lucky.
00:39:08.678 –> 00:39:23.058
JESS: 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.
00:39:24.358 –> 00:39:34.138
JESS: If at all possible, get time with that outgoing assistant and get the inside scoop from them.
00:39:34.138 –> 00:39:35.858
JESS: Every executive is so different.
00:39:35.858 –> 00:39:38.438
JESS: Every executive assistant is so different.
00:39:38.438 –> 00:39:40.518
JESS: We all come from different backgrounds.
00:39:40.518 –> 00:39:43.618
JESS: We all come from different education experiences.
00:39:44.198 –> 00:39:49.118
JESS: We all come from, like for me personally, I haven’t worked in an office for over 10 years.
00:39:50.838 –> 00:39:58.618
JESS: I would have a steep learning curve coming back into an office, and I would need a lot of information from the outgoing person.
00:39:58.618 –> 00:39:59.978
JESS: That’s not always the case.
00:39:59.978 –> 00:40:02.578
JESS: Maybe the person has already moved on to a new role.
00:40:02.578 –> 00:40:05.378
JESS: Maybe they moved state and they’re just not available.
00:40:05.378 –> 00:40:10.698
JESS: Maybe your company doesn’t have the budget to hire them to give you training time.
00:40:10.698 –> 00:40:20.118
JESS: Whatever the case may be, if you can get that training time with the outgoing assistant at all possible, jump at that opportunity.
00:40:20.118 –> 00:40:29.718
JESS: 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.
00:40:29.718 –> 00:40:45.418
JESS: 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.
00:40:45.558 –> 00:40:47.758
JESS: You’re not here to like gossip or anything.
00:40:47.758 –> 00:40:56.178
JESS: But my last in-office executive, he really liked a, it was like a stadium cup.
00:40:56.178 –> 00:41:03.858
JESS: 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.
00:41:04.458 –> 00:41:10.098
JESS: And every day for lunch, he wanted the stadium cup overfilled with ice.
00:41:10.098 –> 00:41:12.778
JESS: I’m talking like a dome of ice on top of it.
00:41:12.778 –> 00:41:20.518
JESS: Like as much as you could get loaded into the cup without it falling off as you would walk it over to him.
00:41:20.518 –> 00:41:21.618
JESS: He wanted that.
00:41:21.618 –> 00:41:29.118
JESS: 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.
00:41:29.118 –> 00:41:36.718
JESS: But he would want the one can of soda and then the crazy cup of ice with his lunch every day.
00:41:38.278 –> 00:41:44.658
JESS: Because the paperwork, the manual that I got said a full and full was bolded and underlined.
00:41:44.658 –> 00:41:51.318
JESS: The outgoing person was just like, no, you don’t understand full, overflowing but still manageable to get it into the room.
00:41:51.318 –> 00:41:58.218
JESS: Just little details like that are really helpful to get from an outgoing person.
00:41:58.218 –> 00:42:09.718
JESS: 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.
00:42:10.238 –> 00:42:24.038
JESS: 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.
00:42:24.038 –> 00:42:28.078
JESS: Giving you honest, here’s how I like to communicate.
00:42:28.078 –> 00:42:33.498
JESS: I as the executive, I like to communicate by text, but I will not answer if you call.
00:42:33.498 –> 00:42:39.798
JESS: I like to DM on Slack, but I will not respond to a text message because my text messages are just a nightmare.
00:42:39.798 –> 00:42:44.998
JESS: Getting little nuance, things like that, and that’s not little when you’re communicating with your executive.
00:42:44.998 –> 00:42:54.978
JESS: 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.
00:42:56.098 –> 00:43:03.998
JESS: So like making sure that they prioritize time to give you taking that time, and getting and documenting those honest answers.
00:43:05.118 –> 00:43:19.258
JESS: 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.
00:43:19.258 –> 00:43:25.298
JESS: Like he’d had a couple of VAs through the Philippines, so this would have been like 2010 to 2013.
00:43:26.898 –> 00:43:31.158
JESS: And he just from his mastermind, they were like, you need an executive assistant.
00:43:31.158 –> 00:43:35.038
JESS: Like you need somebody who can make and answer phone calls.
00:43:35.038 –> 00:43:40.738
JESS: You need somebody who has the connecting the dots skills that an executive assistant has.
00:43:40.738 –> 00:43:46.118
JESS: Somebody who’s going to notice things and help you go further.
00:43:46.118 –> 00:43:54.118
JESS: And I just happened to luck out, be his one interview for the role, and 10 years later, we’re still going strong.
00:43:54.118 –> 00:43:59.098
JESS: We’re just shy of 11 years now, actually, it’ll be 11 years in March of 2025.
00:44:00.158 –> 00:44:18.638
JESS: 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.
00:44:18.958 –> 00:44:21.798
JESS: This is a great opportunity for you and your executive.
00:44:22.018 –> 00:44:26.258
JESS: You’re coming at this with a totally clean slate of an executive.
00:44:26.258 –> 00:44:29.638
JESS: They don’t know what they need help with.
00:44:29.638 –> 00:44:33.578
JESS: Just being very honest with, these are the things that I can take off your plate.
00:44:33.578 –> 00:44:37.238
JESS: These are the things that I should take off your plate.
00:44:37.238 –> 00:44:39.698
JESS: You should no longer be booking your own travel.
00:44:39.698 –> 00:44:42.378
JESS: You should no longer be checking your own email.
00:44:42.378 –> 00:44:59.618
JESS: 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.
00:44:59.618 –> 00:45:12.518
JESS: 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.
00:45:13.938 –> 00:45:38.718
JEREMY: 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.
00:45:38.778 –> 00:46:01.098
JEREMY: 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.
00:46:01.098 –> 00:46:04.458
JEREMY: You’re kind of more saying, hey, here’s how I’ve done things in the past.
00:46:04.458 –> 00:46:06.318
JEREMY: How does this sound to you?
00:46:06.318 –> 00:46:09.038
JEREMY: Here’s how I do calendar management.
00:46:09.038 –> 00:46:10.798
JEREMY: Here’s how I’ve done email management.
00:46:10.878 –> 00:46:16.258
JEREMY: Here’s how assistants around the world typically do this process.
00:46:16.258 –> 00:46:18.698
JEREMY: How does that sound to you kind of a thing?
00:46:19.858 –> 00:46:21.038
JESS: That was definitely something.
00:46:21.038 –> 00:46:31.398
JESS: 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.
00:46:31.398 –> 00:46:49.318
JESS: 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.
00:46:49.318 –> 00:46:50.138
JEREMY: Yeah.
00:46:50.138 –> 00:47:04.158
JESS: 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.
00:47:04.158 –> 00:47:06.518
JEREMY: Yeah.
00:47:06.518 –> 00:47:06.878
JEREMY: Awesome.
00:47:06.938 –> 00:47:08.878
JEREMY: Well, this has been great.
00:47:08.878 –> 00:47:10.718
JEREMY: Lots of great onboarding tips.
00:47:10.718 –> 00:47:22.098
JEREMY: 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?
00:47:22.098 –> 00:47:30.658
JESS: 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.
00:47:30.658 –> 00:47:40.858
JESS: And especially if you do work in a company where potentially the person that is responsible for the onboarding is not warm and approachable.
00:47:40.858 –> 00:47:47.578
JESS: Find a diplomatic way to find the right person for that role.
00:47:47.578 –> 00:47:57.938
JESS: 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.
00:47:57.938 –> 00:48:07.398
JESS: 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.
00:48:07.398 –> 00:48:18.318
JESS: 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.
00:48:18.318 –> 00:48:32.738
JESS: 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.
00:48:34.258 –> 00:48:35.538
JEREMY: Love it.
00:48:35.538 –> 00:48:36.378
JEREMY: Well said, Jess.
00:48:36.378 –> 00:48:40.778
JEREMY: Thank you so much again for sharing your tips.
00:48:40.778 –> 00:49:03.878
JEREMY: 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.
00:49:03.878 –> 00:49:07.078
JEREMY: And I’m excited to highlight your show on my show.
00:49:07.078 –> 00:49:08.598
JESS: Thank you so much for having me back.
00:49:08.598 –> 00:49:14.518
JESS: I’m really excited to be part of The Leader Assistant’s sphere this year and in perpetuity.
00:49:14.518 –> 00:49:15.278
JEREMY: Awesome.
00:49:15.278 –> 00:49:23.018
JEREMY: 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?
00:49:23.018 –> 00:49:25.378
JESS: The best place to find me is askanassistant.com.
00:49:27.018 –> 00:49:32.518
JESS: That is where you can ask your questions, you can listen to the show.
00:49:32.518 –> 00:49:34.838
JESS: I love to hear from any and or all of you.
00:49:34.838 –> 00:49:39.318
JESS: I don’t have a show without folks that are asking questions.
00:49:39.318 –> 00:49:44.358
JESS: No question too big or too small, no problem too large to untangle.
00:49:44.358 –> 00:49:50.938
JESS: Again, the only, and I do mean only, stupid question is the one that you don’t ask.
00:49:52.358 –> 00:49:52.738
JEREMY: Love it.
00:49:52.738 –> 00:49:54.618
JEREMY: Well, thanks again for listening, everyone.
00:49:55.178 –> 00:50:12.438
JEREMY: 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.
00:50:22.762 –> 00:50:25.122
<v SPEAKER_3>Please review on Apple Podcasts.
00:50:31.555 –> 00:50:33.255
<v SPEAKER_3>gobullos.com.
00:50:37.295 –> 00:50:44.255
JEREMY: Hey, friends, my best-selling book, The Leader Assistant, has a companion study and discussion guide to go along with it.
00:50:44.255 –> 00:50:46.955
JEREMY: It’s called The Leader Assistant Workbook.
00:50:46.955 –> 00:50:59.955
JEREMY: 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.
00:51:00.555 –> 00:51:09.155
JEREMY: This version has all the space and margin in between the questions that you can write your own answers and take notes with.
00:51:09.155 –> 00:51:16.595
JEREMY: So it’s a great way to print it out and keep track of your discussion and study guide notes.
00:51:16.595 –> 00:51:22.755
JEREMY: Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.
