Rachel Bennett is a curious, self-motivator who loves to learn new ways to make life more efficient and effective for her executive.
In this episode of The Leader Assistant Podcast, Rachel talks about learning your role while onboarding an executive, communicating with an executive who travels extensively, and serving the work.
LEADERSHIP QUOTE
A day wasted on others is not wasted on oneself.
– Charles Dickens
CONNECT WITH RACHEL
ABOUT RACHEL
Rachel Bennett serves as executive assistant to the president of a nonprofit missions agency that serves missionaries all over the world. She is a curious, self-motivator who loves to learn new ways to make life more efficient and effective for her boss. She is also addicted to Todoist and all things project management software related.
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EPISODE TRANSCRIPT
00:00:00.440 –> 00:00:01.480
RACHEL: Hi, I’m Rachel Bennett.
00:00:01.520 –> 00:00:04.120
RACHEL: Today’s leadership quote comes from Charles Dickens.
00:00:04.800 –> 00:00:08.000
RACHEL: A day wasted on others is not wasted on one’s self.
00:00:14.185 –> 00:00:21.785
<v SPEAKER_3>The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.
00:00:29.791 –> 00:00:36.771
JEREMY: Calling all Executive Assistants, are you looking for a way to elevate your skills or earn that promotion you’ve been eyeing?
00:00:37.671 –> 00:00:45.331
JEREMY: Nova Chief of Staff’s Online Certification Course provides you with the knowledge and confidence you need to stand out on the job.
00:00:46.011 –> 00:00:59.771
JEREMY: Whether you want to land your dream position or level up in your current role, Nova’s Self-Paced Course gives you hands-on practice doing what Chiefs of Staff do every day.
00:01:00.491 –> 00:01:06.671
JEREMY: Visit leaderassistant.com/nova to learn more and secure your spot.
00:01:07.251 –> 00:01:11.791
JEREMY: That’s leaderassistant.com/n-o-v-a.
00:01:11.811 –> 00:01:15.131
JEREMY: Hey friends, welcome to The Leader Assistant Podcast.
00:01:15.151 –> 00:01:20.211
JEREMY: It’s episode 264, and this is your host Jeremy Burrows.
00:01:20.231 –> 00:01:22.751
JEREMY: I’m excited to be speaking with Rachel Bennett today.
00:01:24.371 –> 00:01:32.571
JEREMY: Rachel is an executive assistant to the president of a nonprofit missions agency that serves missionaries all over the world.
00:01:32.851 –> 00:01:38.071
JEREMY: And Rachel, first of all, welcome to the show and tell us what city you’re in.
00:01:39.071 –> 00:01:39.951
RACHEL: Thank you for having me.
00:01:39.971 –> 00:01:42.011
RACHEL: I’m coming from Cleveland, Ohio right now.
00:01:42.031 –> 00:01:43.991
JEREMY: Cleveland, nice.
00:01:44.191 –> 00:01:47.271
JEREMY: So are you from that area originally?
00:01:47.811 –> 00:01:52.311
RACHEL: No, actually I grew up in Southeast Virginia, bounced around a little bit.
00:01:52.311 –> 00:01:59.191
RACHEL: I moved to Pennsylvania when I was in high school and then went to school in South Carolina and moved up here after graduating college.
00:02:00.171 –> 00:02:02.731
JEREMY: Okay, so a little all over.
00:02:03.231 –> 00:02:03.531
RACHEL: Yeah.
00:02:04.271 –> 00:02:04.751
JEREMY: For sure.
00:02:05.731 –> 00:02:09.171
JEREMY: Cool, well, tell us a little bit about yourself personally.
00:02:10.231 –> 00:02:15.711
JEREMY: Do you have cats, dogs, kids, goldfish, all of the above?
00:02:16.591 –> 00:02:17.731
RACHEL: I have two dogs.
00:02:18.491 –> 00:02:20.431
RACHEL: We took on two puppies.
00:02:20.451 –> 00:02:31.271
RACHEL: So I have a two-year-old springer doodle, springer-spraniel mix with a poodle, and a six-month-old cockapoo, so cocker-spraniel and a poodle.
00:02:31.291 –> 00:02:33.291
RACHEL: So they keep us running.
00:02:33.711 –> 00:02:35.511
RACHEL: I’ve been married for almost two years.
00:02:37.351 –> 00:02:43.411
RACHEL: But yeah, we’re busy with two toddler fur babies right now and they keep us on our toes.
00:02:44.591 –> 00:02:45.431
JEREMY: Love it, love it.
00:02:46.091 –> 00:02:53.071
JEREMY: So what got you in to the world of executive assistants?
00:02:54.571 –> 00:02:56.511
RACHEL: I would say I probably stumbled into it.
00:02:56.571 –> 00:03:00.031
RACHEL: And the short answer is I really needed a job after college.
00:03:02.071 –> 00:03:06.511
RACHEL: I was looking for admin-type work in South Carolina, which is where I went to school.
00:03:06.831 –> 00:03:12.491
RACHEL: All the jobs kept flying through, and I ended up taking a position as an administrative assistant here.
00:03:13.331 –> 00:03:16.111
RACHEL: And that was about, goodness, that’s about six years ago.
00:03:16.991 –> 00:03:19.411
RACHEL: And I worked for two different administrators.
00:03:19.431 –> 00:03:23.731
RACHEL: So one was in the office and the other one was based in Taiwan.
00:03:23.831 –> 00:03:32.651
RACHEL: So I kind of had my role split between working with someone that was right there, working with someone who was overseas, different time zone and everything that goes along with that.
00:03:32.671 –> 00:03:38.751
RACHEL: But I first got interested in admin work probably when I was in college in my senior year.
00:03:39.011 –> 00:03:42.331
RACHEL: I did an internship with a pregnancy medical clinic in South Carolina.
00:03:45.291 –> 00:03:49.391
RACHEL: I went to school for counseling, but I also really enjoyed the admin work.
00:03:49.411 –> 00:03:54.331
RACHEL: So I did like reception work, scheduling, call center work, that sort of thing.
00:03:54.371 –> 00:04:00.791
RACHEL: But I just like to be available to help people with organization and communications, that sort of thing.
00:04:00.811 –> 00:04:04.171
RACHEL: So that’s probably what got me interested in it in the first place.
00:04:05.831 –> 00:04:06.851
JEREMY: Did you see it?
00:04:07.611 –> 00:04:09.611
JEREMY: You said you wanted a, you needed a job.
00:04:10.471 –> 00:04:13.951
JEREMY: But how long have you been an assistant now?
00:04:14.771 –> 00:04:17.031
RACHEL: It’ll be six years this coming May.
00:04:18.691 –> 00:04:27.411
JEREMY: And when did you kind of transition from, oh, I need a job to, oh, okay, I think I like this and I could do this for a career?
00:04:29.091 –> 00:04:30.711
RACHEL: Probably in the first couple of years.
00:04:32.411 –> 00:04:38.331
RACHEL: So I worked for two years as an Administrative Assistant for the two administrators I mentioned previously.
00:04:38.951 –> 00:04:46.091
RACHEL: And it was probably at the end of those two years that I started really getting into a flow with working with my one administrator.
00:04:46.111 –> 00:04:49.671
RACHEL: We kind of think what the other person was going to say.
00:04:49.971 –> 00:04:57.171
RACHEL: And it just got really a smooth working relationship that it was effective and it felt very successful.
00:04:58.011 –> 00:05:07.051
RACHEL: And it was at that point that our organization went through a leadership change where we had a new president coming on the summer of 2020.
00:05:07.811 –> 00:05:17.391
RACHEL: And I was asked to consider coming on as the Executive Assistant for him and felt very underqualified and not quite ready for it.
00:05:17.411 –> 00:05:22.851
RACHEL: But I jumped in and been doing that for four years now and had some bumps along the way.
00:05:22.871 –> 00:05:26.451
RACHEL: But I think we’re probably the best working relationship we’ve had so far.
00:05:27.271 –> 00:05:29.371
RACHEL: So it’s been really cool to see that progress.
00:05:31.311 –> 00:05:35.051
JEREMY: And what was maybe, you said, some bumps along the way?
00:05:35.071 –> 00:05:41.291
JEREMY: Are there any challenges or struggles or bumps, speed bumps that you want to share a little bit about?
00:05:41.791 –> 00:05:45.171
RACHEL: Probably the biggest bump was my own insecurity coming into the role.
00:05:45.351 –> 00:05:47.871
RACHEL: I didn’t think I had what it takes.
00:05:47.971 –> 00:05:55.711
RACHEL: And I think I was probably more concerned about other people not thinking that I had what it takes to do the position and to do it well.
00:05:56.431 –> 00:05:58.791
RACHEL: So that was one hurdle on my own part.
00:05:58.811 –> 00:06:14.331
RACHEL: And just working with the administrator and executive who is very different personality-wise from myself, who is, I think he was filling out the role himself while I was learning my role.
00:06:14.351 –> 00:06:19.471
RACHEL: And so we were both learning two different roles together at the same time and learning to communicate well.
00:06:19.511 –> 00:06:21.571
RACHEL: And communication has been a big thing.
00:06:21.771 –> 00:06:26.631
RACHEL: But it’s really improved and yeah, it’s gone really well.
00:06:28.711 –> 00:06:38.511
JEREMY: So one of the topics you suggested when I asked you what topics you wanted to cover was learning your role while onboarding your executive.
00:06:38.531 –> 00:06:50.131
JEREMY: Is that kind of what you’re referring to, that idea of like, so was it because the executive was new to the organization or was it because they had never had an assistant before or both?
00:06:52.291 –> 00:06:54.531
RACHEL: I would say just because he was new to the organization.
00:06:54.551 –> 00:07:08.091
RACHEL: He had worked with assistants in the past, but not quite in this type of role where it requires a very, how we call it, synchronous relationship where you’re both in tune and helping each other out on the same team, communicating a lot.
00:07:08.671 –> 00:07:12.171
RACHEL: And when he came onto this role, there’s a lot of travel involved.
00:07:12.311 –> 00:07:17.911
RACHEL: So most of the time of the year, he’s not actually in the office and I have to keep ball rolling on things.
00:07:18.071 –> 00:07:23.311
RACHEL: We have to communicate well and not let things fall through the cracks while there’s so much travel going on.
00:07:23.331 –> 00:07:27.051
RACHEL: So that was a different dynamic that took some getting used to for both of us.
00:07:28.751 –> 00:07:46.751
JEREMY: What’s maybe one thing during that time that if you’re going to do that again, you would maybe do differently or even just a practical tip for figuring it out on the fly as you’re onboarding an executive?
00:07:48.231 –> 00:07:52.031
RACHEL: Probably more patience with myself, to be honest.
00:07:52.631 –> 00:07:54.691
RACHEL: I can be a little hard on myself when I make mistakes.
00:07:55.331 –> 00:08:07.391
RACHEL: And there was a process where I was really focused on building trust with my executive and knowing that there had been maybe some bumps in previous relationships, working relationships in the past.
00:08:08.231 –> 00:08:10.951
RACHEL: I was really focused on getting everything right the first time.
00:08:11.631 –> 00:08:14.391
RACHEL: You’re human, you make mistakes, that doesn’t happen all the time.
00:08:15.051 –> 00:08:18.251
RACHEL: And you have to be a little bit gracious with yourself when you do make those mistakes.
00:08:18.271 –> 00:08:25.011
RACHEL: But I would beat myself up and worry that I had just pushed myself further back in the process of building that trust.
00:08:25.391 –> 00:08:29.111
RACHEL: And that probably didn’t do either of us any favors.
00:08:29.131 –> 00:08:31.171
RACHEL: So that was probably one thing I would do differently.
00:08:33.451 –> 00:08:42.931
JEREMY: And you mentioned that before the insecurity and just kind of like not having that confidence that you had what it takes.
00:08:42.951 –> 00:08:55.271
JEREMY: What has helped you, now that you’ve been in the role for a while, what has helped you overcome those feelings of, you know, I don’t know if I have what it takes.
00:08:56.291 –> 00:08:58.931
RACHEL: Probably experience and maturity plays into it.
00:08:58.951 –> 00:09:01.351
RACHEL: I felt like I was pretty young when I came onto the position.
00:09:01.371 –> 00:09:10.431
RACHEL: So, you know, being in the seat for a while helps you feel like, okay, I probably deserve to be in the seat because I’ve been doing the job for now as long as I have.
00:09:10.451 –> 00:09:20.871
RACHEL: But I think kind of one of the things that comes out in the book about serving the work and about having a mindset that I’m here to serve other people.
00:09:20.891 –> 00:09:30.071
RACHEL: I’m not just here to get my way and do what I want to do, but I’m here to provide a service, especially to my executive and to the people that we minister to.
00:09:31.431 –> 00:09:42.471
RACHEL: So having that mindset, I think, helps overcome that challenge where you see yourself as there to serve other people and not just to do what you want to do necessarily.
00:09:44.031 –> 00:09:44.251
JEREMY: Yeah.
00:09:44.271 –> 00:09:47.471
JEREMY: And for those listening, you know, I talk about this idea.
00:09:47.491 –> 00:09:59.511
JEREMY: There’s this quote from Dorothy Sayers in my book, The Leader Assistant, where she talks about the difference between angling for applause and serving the work.
00:09:59.511 –> 00:10:09.951
JEREMY: In other words, are you working to get affirmation and approval from others, or are you working because you want to do well, you want to do good work?
00:10:11.411 –> 00:10:23.611
JEREMY: And how Dorothy Sayers, she says that the community as a whole thrives when people care more about serving the work than angling for applause from others.
00:10:23.711 –> 00:10:29.451
JEREMY: And so anyway, that’s just kind of a side note as your to your reference of serving the work.
00:10:30.051 –> 00:10:34.031
JEREMY: And I think that, you know, experience is a big thing.
00:10:34.051 –> 00:10:52.731
JEREMY: I think that really grounding yourself on a regular basis with the, you know, OK, I’m not going to take this personally, you know, if somebody says something or disapproves of something I did, or like you said, your heart on yourself when you make mistakes.
00:10:54.711 –> 00:11:07.071
JEREMY: Just realizing that, hey, listen, you know, doesn’t really matter what other people think and doesn’t really matter if so and so approves of me.
00:11:07.491 –> 00:11:10.571
JEREMY: What matters is am I doing the best that I can with the tools that I have?
00:11:10.691 –> 00:11:12.871
JEREMY: And am I actually doing good work?
00:11:13.731 –> 00:11:15.851
JEREMY: And then the rest kind of falls into place typically.
00:11:15.871 –> 00:11:18.091
JEREMY: So anyway, thanks for.
00:11:18.091 –> 00:11:24.091
RACHEL: Yeah, I had that lesson taught to me pretty early on when I was being considered for the role.
00:11:24.491 –> 00:11:33.031
RACHEL: The former president of the mission had recommended me and he was available to, you know, talk to the process with me and that sort of thing.
00:11:33.051 –> 00:11:36.431
RACHEL: And I kept coming back to that question of do you actually think I can do this?
00:11:36.731 –> 00:11:38.091
RACHEL: Because I don’t think I can do this.
00:11:38.751 –> 00:11:45.971
RACHEL: And eventually, I think he got tired of me asking that and said, Rachel, you know, if God wants you to do this, you’re going to be okay.
00:11:46.211 –> 00:11:47.371
RACHEL: And you’re going to do your best.
00:11:47.551 –> 00:11:49.291
RACHEL: And it doesn’t matter what other people think.
00:11:50.831 –> 00:11:51.991
RACHEL: And I was like, you know what?
00:11:52.131 –> 00:11:53.311
RACHEL: I just need to get over it.
00:11:53.831 –> 00:11:54.531
JEREMY: Right, right.
00:11:56.651 –> 00:11:57.051
JEREMY: Awesome.
00:11:57.511 –> 00:12:06.191
JEREMY: So what about you said you’re an executive, or you’ve worked with executives, you know, in the past as well, but who travel a lot.
00:12:06.651 –> 00:12:15.351
JEREMY: What’s some good tips on keeping track of all the different time zones and the travel itineraries and the flight changes and all the things.
00:12:16.631 –> 00:12:28.511
JEREMY: But then on top of that, not just logistically organizing all that, but trying to stay in communication and constant sync with an executive who’s gone all the time.
00:12:28.851 –> 00:12:33.471
RACHEL: Yeah, I’d say tools like monday.com have been a lifesaver.
00:12:34.271 –> 00:12:38.971
RACHEL: Those type of dashboards where we can both see the same thing at the same time.
00:12:38.991 –> 00:12:43.411
RACHEL: We even have it set up so that his priorities are on a dashboard.
00:12:43.491 –> 00:12:49.591
RACHEL: I can go in and see what he’s focusing on every week and what the priority level of each item is.
00:12:49.611 –> 00:12:52.111
RACHEL: I can upload files.
00:12:52.131 –> 00:12:53.751
RACHEL: I can add updates, that sort of thing.
00:12:54.051 –> 00:12:59.711
RACHEL: So having that collaboration where we’re both seeing the same things at the same time has been awesome.
00:12:59.711 –> 00:13:03.051
RACHEL: We have a regular one-on-one that happens every week.
00:13:04.811 –> 00:13:13.211
RACHEL: It’s on the same day, at the same time, and it can get moved wherever it wants to get moved, but the rule is that I think I’m the only one that’s allowed to delete it.
00:13:13.251 –> 00:13:16.591
RACHEL: So you can ignore the one-on-one meeting, but you’re not allowed to delete it.
00:13:16.631 –> 00:13:32.391
RACHEL: So we have a shared Google Doc where we’ll just make a really simple grid of items that I need answers on or I need to move forward with, and then he can go in to that shared document anytime and put in answers or updates so that I can move forward.
00:13:33.591 –> 00:13:38.311
RACHEL: And he can do that whenever he wants, but when it comes to the one-on-one meeting, that’s the document that we’re going to go through.
00:13:38.331 –> 00:13:45.231
RACHEL: So if he has free time, he can chime in and give some answers on things so we don’t have to spend that time on the one-on-one.
00:13:45.371 –> 00:13:48.251
RACHEL: That’s kind of how we handle the day-to-day stuff.
00:13:49.591 –> 00:13:57.871
JEREMY: And then what about like, you know, I’ve had this happen a few times in my career, and it’s like the worst feeling ever and the worst day ever.
00:13:58.111 –> 00:14:09.191
JEREMY: But, you know, your executive is traveling, and you get that dreaded call, my flight got canceled or my there’s a delay and I’m going to miss my connecting flight.
00:14:09.311 –> 00:14:11.531
JEREMY: Like what do you work with travel agents?
00:14:11.551 –> 00:14:14.171
JEREMY: Do you kind of try to manage it yourself?
00:14:14.451 –> 00:14:24.271
JEREMY: How is there certain software or sites that you like to use to help re-book and change the itineraries?
00:14:25.331 –> 00:14:45.911
RACHEL: Yeah, I think I’m probably blessed in that area in that I do most of his travel planning myself unless it’s a very complicated international itinerary, in which case I work through a travel agent so that they can be the on-call person, especially if a flight gets canceled, and it’s a complicated situation where he’s overseas and he needs help in that way.
00:14:46.111 –> 00:14:55.651
RACHEL: But for domestic transportation, I handle that pretty much myself, but like I said, I think I’m blessed in that if something goes wrong, he’s usually the one that handles it himself.
00:14:57.051 –> 00:15:01.991
RACHEL: That’s not the same situation for everybody, but I’m a little bit lucky in that regard, I think.
00:15:02.011 –> 00:15:05.251
JEREMY: I was going to say there’s a lot of assistants listening right now.
00:15:05.271 –> 00:15:07.211
JEREMY: They’re like, oh man, that would be nice.
00:15:08.231 –> 00:15:20.051
RACHEL: We’re pretty good on boundaries, and I’m thankful for that in the sense of, you know, if something happens on the weekend or on the evening, it’s pretty much an emergency level for him to contact me about it.
00:15:20.071 –> 00:15:21.551
RACHEL: And this is the same thing that goes for me.
00:15:21.571 –> 00:15:26.131
RACHEL: So we both try to respect that boundary and makes for a really good working relationship.
00:15:27.231 –> 00:15:28.011
JEREMY: Yeah, that’s huge.
00:15:30.631 –> 00:15:45.531
JEREMY: So, you know, in your little bio that you shared with me that I’ll put in the show notes at leaderassistant.com/264, you say that you’re addicted to Todoist and all things project management software.
00:15:45.551 –> 00:15:50.591
JEREMY: So what do you like about Todoist, for example, and then just in general, project management?
00:15:50.611 –> 00:15:56.711
JEREMY: Because I personally was a project manager for about a year in the middle of my EA career, and I could not stand it.
00:15:56.751 –> 00:16:02.171
JEREMY: I felt like I was a babysitter for all these other people, and I was just like, no, I just want to do my work.
00:16:02.191 –> 00:16:05.631
JEREMY: I don’t want to have to tell other people and remind other people to do their work.
00:16:05.671 –> 00:16:07.371
JEREMY: So anyway, what’s your…
00:16:07.391 –> 00:16:12.071
JEREMY: Yeah, why do you like Todoist and what do you like about project management?
00:16:12.871 –> 00:16:20.751
RACHEL: When I first started as an executive assistant, I was still using paper and pen, which there’s nothing wrong with that if that works for you.
00:16:21.511 –> 00:16:24.851
RACHEL: Kudos to you, it did not work for me after about 24 hours.
00:16:24.971 –> 00:16:36.131
RACHEL: So I quickly switched over to looking at a digital task management system, and I tried out a couple of different ones, but I really stuck on Todoist because it was so simple to use.
00:16:36.791 –> 00:16:53.231
RACHEL: I can just type in meet with my boss, T-O-M-P-1, hashtag, whatever project, and then it would schedule that task automatically for the next day, priority one, and then put it in the right project that I needed to go into that project listing and see everything that was underneath there.
00:16:54.211 –> 00:16:55.391
RACHEL: So it was just simple.
00:16:56.291 –> 00:16:58.271
RACHEL: It didn’t take me a ton of time to learn.
00:16:58.291 –> 00:17:01.831
RACHEL: It was easy to set up, and it was really customizable for what I wanted.
00:17:01.851 –> 00:17:09.471
RACHEL: I used money.com for more process workflows and that sort of thing myself.
00:17:09.531 –> 00:17:15.051
RACHEL: I don’t have a ton of collaboration with other teams on it, but it’s helpful for me to keep everything in one place.
00:17:15.071 –> 00:17:16.831
JEREMY: Nice.
00:17:16.891 –> 00:17:17.951
JEREMY: And do you enjoy…
00:17:17.971 –> 00:17:27.331
JEREMY: And is it more project management for you and your executive, or do you also manage, like, projects across the team?
00:17:28.151 –> 00:17:31.791
RACHEL: It’s mostly for myself and my executive.
00:17:32.271 –> 00:17:44.151
RACHEL: There’s some committee and event management that we use that software for and it helps keep, mostly like my timelines, for everything that needs to happen, keeping that going in the right direction.
00:17:44.911 –> 00:18:00.631
RACHEL: It was a bit of a change coming from my previous role into this one that I have more event management and longer projects where, in my role before, it was more day-to-day tasks that would conclude at the end of the day and I usually could wrap everything up pretty quickly.
00:18:01.231 –> 00:18:08.871
RACHEL: But this was more like, okay, you’ve got an event coming six months in advance, you better be doing your work now or you’re going to be in trouble in six months.
00:18:09.411 –> 00:18:15.571
RACHEL: So I quickly learned that I needed a tool outside of just pen and paper to keep track of where everything needs to be.
00:18:18.331 –> 00:18:38.911
JEREMY: And then another thing I wanted to highlight is, as an assistant, and really you can see this in the job descriptions when people are hiring an assistant, but this idea of being self-motivated or a self-starter, were you like that?
00:18:38.931 –> 00:18:41.631
JEREMY: You mentioned you’re a curious self-motivator.
00:18:42.431 –> 00:18:53.571
JEREMY: Were you like that when you started your career or did you just kind of evolve into, hey, I really need to be self-managed or initiate things on my own?
00:18:53.571 –> 00:18:57.111
JEREMY: I can’t just wait for my executive to guide me.
00:18:57.571 –> 00:19:00.071
RACHEL: I’d say I was pretty self-motivated from the start.
00:19:00.531 –> 00:19:03.451
RACHEL: I love to learn new things and figure out things I didn’t know before.
00:19:03.471 –> 00:19:07.311
RACHEL: So, I have an example in college.
00:19:07.411 –> 00:19:12.611
RACHEL: I rarely used Excel in college, which was a nice experience not to have to use Excel.
00:19:14.811 –> 00:19:17.751
RACHEL: So, I started working with a recruiting agency to find a job.
00:19:18.211 –> 00:19:24.311
RACHEL: One of the things they wanted me to do was a Microsoft assessment to see how good your skills are with Excel.
00:19:24.451 –> 00:19:26.811
RACHEL: I was panicking because I’d never used it before.
00:19:26.851 –> 00:19:33.751
RACHEL: So, I started watching as many YouTube videos as I possibly could about how to do formulas and learn Excel.
00:19:33.771 –> 00:19:35.151
RACHEL: I just found it fun.
00:19:36.731 –> 00:19:53.591
RACHEL: Even when it came to finding the right software to use when I needed to switch over to a digital system, I looked at ClickUp and Office Otter and asanamoney.com and pretty much whatever I could get my hands on in just a way which one I liked the best.
00:19:53.871 –> 00:19:55.171
RACHEL: That’s the kind of thing.
00:19:55.251 –> 00:19:56.331
RACHEL: It’s fun to learn new things.
00:19:56.351 –> 00:19:57.571
JEREMY: Nice.
00:19:58.531 –> 00:20:03.331
JEREMY: Yeah, I think being curious is one of the best traits to have as an assistant.
00:20:05.571 –> 00:20:20.231
JEREMY: It really helps you learn more about the context of your organization, your executives, work that they’re involved in, your team, and so on and so forth.
00:20:21.571 –> 00:20:27.071
JEREMY: Well, Rachel, what would you like to say to new assistants?
00:20:27.251 –> 00:20:39.751
JEREMY: So if you’ve got assistants listening who maybe they’re just about to start their first assistant job or they’re a couple months in, any tips for the newbies listening?
00:20:40.411 –> 00:20:44.051
RACHEL: I still feel like a newbie, so I feel I’ve earned the right to say that.
00:20:44.071 –> 00:20:55.191
RACHEL: But I would say just have patience with yourself, patience with the process and the fact that it takes time to build trust and to develop a solid working relationship with your executive.
00:20:56.551 –> 00:20:58.011
RACHEL: Don’t hold your work too personally.
00:20:59.391 –> 00:21:00.511
RACHEL: It’s work for other people.
00:21:00.531 –> 00:21:02.091
RACHEL: It’s not always just work for you.
00:21:02.111 –> 00:21:05.631
RACHEL: I made that mistake before.
00:21:05.651 –> 00:21:16.811
RACHEL: I remember spending hours on a PowerPoint to have it get shredded the next day because I was focused on what I wanted it to be and not what it needed to be for my executive, that sort of thing.
00:21:18.611 –> 00:21:25.591
RACHEL: But yeah, just realize that it takes time to develop that relationship.
00:21:25.711 –> 00:21:29.631
RACHEL: It doesn’t come overnight, but have patience and keep working hard.
00:21:35.138 –> 00:21:37.718
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00:22:12.158 –> 00:22:12.578
JEREMY: Well said.
00:22:12.598 –> 00:22:14.858
JEREMY: Okay, so let’s fast forward then.
00:22:14.878 –> 00:22:19.978
JEREMY: We kind of rewound to newbies, but let’s fast forward.
00:22:19.998 –> 00:22:23.918
JEREMY: Where do you see your career going in the next five years?
00:22:25.158 –> 00:22:31.358
JEREMY: Are you excited about the role and do you see yourself as an assistant, I guess I should say, in the long run?
00:22:32.438 –> 00:22:37.998
JEREMY: Have you thought about the trajectory of your role as an assistant?
00:22:38.618 –> 00:22:39.578
RACHEL: That’s a good question.
00:22:39.598 –> 00:22:49.098
RACHEL: I don’t know if I see it in the long run, in the sense that I recently got married, I’m excited to build a family with my husband in the future.
00:22:49.638 –> 00:22:53.178
RACHEL: But where I am right now, I’m excited to be.
00:22:53.198 –> 00:23:10.858
RACHEL: The fact that I have the opportunity to build relationships with stakeholders, with donors, with many of the different ministries that we come into contact with, and I really enjoy the opportunity to serve them and to do my job well, and to learn how to do it better.
00:23:11.458 –> 00:23:14.258
RACHEL: So it’s kind of an ambiguous answer, but it’s what I got.
00:23:15.118 –> 00:23:15.698
JEREMY: Fair enough.
00:23:16.118 –> 00:23:19.418
JEREMY: How many are on your team, it’s your organization?
00:23:19.638 –> 00:23:21.338
JEREMY: How many employees?
00:23:21.358 –> 00:23:24.998
RACHEL: I would say under 50 staff members that are here on-site in Cleveland.
00:23:26.298 –> 00:23:30.538
RACHEL: The missionaries that we serve around the world is, I would say, around 450.
00:23:31.998 –> 00:23:34.138
JEREMY: And are you the only assistant in the organization?
00:23:34.418 –> 00:23:35.098
RACHEL: No, no.
00:23:35.618 –> 00:23:42.818
RACHEL: No, I’m the only assistant to my executive, but we have some other really key players in the office here that do a great job.
00:23:44.238 –> 00:23:51.418
JEREMY: Any tips or anything you’ve learned working with other assistants?
00:23:51.438 –> 00:23:52.358
RACHEL: Don’t compare yourself.
00:23:54.078 –> 00:24:00.938
RACHEL: That’s another thing that every working relationship with an executive is different, and that’s okay.
00:24:00.998 –> 00:24:04.478
RACHEL: It doesn’t all have to look the same way that your relationship works.
00:24:04.538 –> 00:24:12.678
RACHEL: And there’s always something that you can learn from something that someone else is doing maybe better, something that they can learn from how you’re working with your executive.
00:24:14.418 –> 00:24:16.098
RACHEL: So, yeah, stay humble.
00:24:17.298 –> 00:24:17.578
JEREMY: Yeah.
00:24:17.598 –> 00:24:29.418
JEREMY: So when you say compare, you know, are you, for you personally, are you talking like you would struggle to compare saying, oh, this person’s got more experience than me?
00:24:29.698 –> 00:24:34.118
JEREMY: Or, you know, how are you comparing yourself to the other assistants?
00:24:34.758 –> 00:24:36.038
RACHEL: Mostly experience.
00:24:36.218 –> 00:24:49.618
RACHEL: And I would say too, and I’ve noticed this more in the last couple of months, that when you see an assistant and their executive doing really well together and operating really well together, it’s easy to make the assumption that it’s like that all the time for them.
00:24:50.678 –> 00:24:51.898
RACHEL: It’s not like that all the time.
00:24:51.918 –> 00:24:58.878
RACHEL: I know that even with my own executive, there are times where I even thought like, you know, if somebody, you know, watches interaction, they’d be really impressed with it.
00:24:58.898 –> 00:25:02.818
RACHEL: And then five minutes later, I’m like, oh, I guess I can’t believe that he did that and that type of thing.
00:25:03.158 –> 00:25:05.718
RACHEL: So don’t make those type of judgment calls.
00:25:06.638 –> 00:25:11.158
RACHEL: Every working relationship, it has the highs and the lows and that’s okay.
00:25:11.638 –> 00:25:11.978
JEREMY: Yeah.
00:25:13.038 –> 00:25:24.438
JEREMY: What do you, what do you tell people, whether it’s friends, family, you know, people you run into at a coffee shop, what do you tell people when they ask you, what do you do?
00:25:24.458 –> 00:25:31.018
RACHEL: It doesn’t sound really good, but I tell them I send a lot of emails, which is true.
00:25:31.478 –> 00:25:48.398
RACHEL: But yeah, mostly the majority of what I do is a lot of travel management, board relations, donor relations, a lot of communication with our missionaries and then with outside parties.
00:25:49.378 –> 00:25:51.758
RACHEL: So a lot of email.
00:25:52.418 –> 00:25:54.018
JEREMY: Yeah.
00:25:54.098 –> 00:25:57.598
JEREMY: What is your number one email management tip?
00:25:57.638 –> 00:25:59.798
JEREMY: And do you manage your executive’s email or?
00:26:00.658 –> 00:26:01.678
RACHEL: Yeah.
00:26:02.378 –> 00:26:09.898
RACHEL: I went through a certification earlier this year that kind of had me just reorganize how I do my own email.
00:26:09.978 –> 00:26:18.998
RACHEL: But it’s not original with me by any means, but I have a Action Reply folder, a Pending folder and an Archive folder.
00:26:19.378 –> 00:26:24.298
RACHEL: And everything that comes in my inbox goes into one of those folders within the day.
00:26:24.878 –> 00:26:29.538
RACHEL: So I have a zero inbox, but I have a larger Reply folder.
00:26:29.558 –> 00:26:30.598
RACHEL: So it’s not a big deal.
00:26:30.618 –> 00:26:36.198
RACHEL: But yeah, so that’s actually been probably one of the most helpful things.
00:26:36.818 –> 00:26:41.778
RACHEL: But it’s one of those results of being curious and seeing how other people do things.
00:26:41.798 –> 00:26:43.238
RACHEL: And like, I want to give that a shot.
00:26:43.618 –> 00:26:45.438
RACHEL: And I did and never looked back.
00:26:45.458 –> 00:26:46.938
RACHEL: It’s been very nice.
00:26:48.138 –> 00:26:51.538
JEREMY: So you do that for your inbox and your executive’s inbox?
00:26:51.858 –> 00:26:52.938
RACHEL: I do it for my inbox.
00:26:52.958 –> 00:26:54.118
RACHEL: We’re working on my executive.
00:26:54.138 –> 00:26:56.658
RACHEL: So we’re getting there.
00:26:56.678 –> 00:26:58.958
RACHEL: I was going to say.
00:26:58.978 –> 00:27:00.138
RACHEL: So that’s a start.
00:27:00.418 –> 00:27:01.498
JEREMY: You said action folder?
00:27:01.518 –> 00:27:02.838
JEREMY: Nice.
00:27:03.098 –> 00:27:03.418
RACHEL: Nice.
00:27:04.218 –> 00:27:13.238
JEREMY: Yeah, it’s always such a give and take, really, with your executive’s inbox, because it’s like, well, they want to do it this way.
00:27:13.258 –> 00:27:15.398
JEREMY: But you know that that’s not the most efficient.
00:27:16.038 –> 00:27:24.518
JEREMY: But you want to change the system in a way that they see the value in it, you know, and that they can get on board with it.
00:27:24.538 –> 00:27:27.178
JEREMY: Otherwise, they won’t actually, they won’t change anything.
00:27:27.198 –> 00:27:28.438
JEREMY: They won’t do anything different.
00:27:28.978 –> 00:27:29.738
JEREMY: Yeah.
00:27:30.438 –> 00:27:34.558
JEREMY: So what’s your what’s your favorite part, though, about your current role?
00:27:34.578 –> 00:27:36.438
JEREMY: Like, is it the travel?
00:27:36.458 –> 00:27:40.458
JEREMY: Is it the is it the email?
00:27:40.458 –> 00:27:47.498
JEREMY: Is it the just being involved in the executive level conversations?
00:27:47.518 –> 00:27:49.818
JEREMY: Like what’s your what’s your favorite part of your role?
00:27:50.818 –> 00:27:53.018
RACHEL: Probably really enjoy the travel arrangement.
00:27:53.278 –> 00:27:57.898
RACHEL: So my boss is most of the time not in the office.
00:27:57.918 –> 00:28:10.678
RACHEL: But every time he goes somewhere, whether it is speak at a church or school or a conference, there’s tons of different pieces of the puzzle that I have to put together and make sure it’s a fluid experience for him that I haven’t missed anything.
00:28:10.698 –> 00:28:17.518
RACHEL: But getting to know him better has been it’s been helpful in the sense that I can see things coming now that I couldn’t see before.
00:28:17.698 –> 00:28:24.418
RACHEL: And I know the questions to ask to get the ball rolling on questions that will come up later if they’re not answered right now.
00:28:24.798 –> 00:28:29.198
RACHEL: So I enjoy that part of the puzzle, the unknown that something can always come up.
00:28:30.018 –> 00:28:30.338
JEREMY: Yeah.
00:28:32.198 –> 00:28:37.798
JEREMY: And then is there do you can you think of any of those questions off the top of your head?
00:28:37.818 –> 00:28:55.338
JEREMY: Like, if if someone listening has an executive that travels a lot and speaks at conferences and whatever, is there like a go to like, you know, two or three questions that you’re like, I’ve got to get the answers to these and then I can I can run from there.
00:28:56.238 –> 00:28:58.098
RACHEL: Um, it’s usually related to speaking.
00:28:58.118 –> 00:29:03.518
RACHEL: For example, my executive wants to know the theme that he’s supposed to be speaking on.
00:29:03.538 –> 00:29:07.538
RACHEL: He wants to know what time he starts, what time he stops, how long he’s supposed to be speaking.
00:29:08.698 –> 00:29:13.918
RACHEL: He wants to know who’s been speaking there before what their topics have been that sort of thing.
00:29:15.538 –> 00:29:16.718
RACHEL: That will be an example.
00:29:17.018 –> 00:29:17.378
JEREMY: But, yeah.
00:29:18.878 –> 00:29:19.198
JEREMY: Yeah.
00:29:20.438 –> 00:29:26.058
JEREMY: I’ve done a lot of coordinating for my executives for speaking engagements as well.
00:29:27.178 –> 00:29:29.798
JEREMY: And then obviously now I do my own speaking engagements.
00:29:29.818 –> 00:29:34.678
JEREMY: So I kind of have fun to be on the other side of the planning too.
00:29:34.698 –> 00:29:37.038
JEREMY: But yeah, those are good tips.
00:29:37.778 –> 00:29:40.358
JEREMY: So Rachel, thank you so much for being on the show.
00:29:40.378 –> 00:29:41.298
JEREMY: It’s been fun to chat.
00:29:42.018 –> 00:29:50.658
JEREMY: Sounds like you’ve got a fun environment and a fun executive partnership going and you’re learning and you’re curious.
00:29:50.698 –> 00:29:55.198
JEREMY: And so keep leading well and keep being curious.
00:29:55.918 –> 00:29:59.058
JEREMY: And is there any kind of final word that you want to say?
00:29:59.078 –> 00:30:16.158
JEREMY: Or one way I like to ask at the end of the conversations are, you know, if you were to put a billboard on the busiest highway in the world that all the assistants drove by on their way to work, what would you what would you put on that billboard?
00:30:18.958 –> 00:30:22.098
RACHEL: I probably put something along the lines of that life is for service.
00:30:25.358 –> 00:30:31.818
RACHEL: And that’s where I get my fulfillment from knowing that I can help other people be a benefit to other people.
00:30:32.078 –> 00:30:34.878
RACHEL: And I enjoy that part of my job very much.
00:30:35.018 –> 00:30:37.818
RACHEL: But thank you so much for the privilege of coming on.
00:30:37.818 –> 00:30:39.178
RACHEL: I really enjoy the conversation.
00:30:40.278 –> 00:30:41.498
JEREMY: Yeah, yeah, my pleasure.
00:30:41.658 –> 00:30:47.178
JEREMY: And we’ll put your is it okay to put your LinkedIn in the show notes and people reach out and say hi?
00:30:48.638 –> 00:30:49.258
JEREMY: Okay, cool.
00:30:49.638 –> 00:30:50.378
JEREMY: Well, I’ll do that.
00:30:50.398 –> 00:31:00.358
JEREMY: Rachel, the show notes will be leaderassistant.com/264leaderassistant.com/ 264.
00:31:00.718 –> 00:31:02.178
JEREMY: Thank you, everyone for listening.
00:31:02.358 –> 00:31:04.198
JEREMY: And thank you, Rachel, for being on the show.
00:31:04.398 –> 00:31:06.098
JEREMY: And have a have a great week.
00:31:16.122 –> 00:31:18.882
RACHEL: Please review on Apple Podcasts.
00:31:25.240 –> 00:31:27.020
RACHEL: goburrows.com.
