Ask an Assistant Spotlight - Weird Requests

Jeremy · 0:00

In-person meeting planning can be a lot to manage, but that's where TROOP Planner comes in. From organizing an executive offsite, department meeting or team retreat, TROOP Planner is built to make life easier for busy assistants like you. TROOP keeps it simple, fast and organized. From choosing the perfect location to managing budgets, coordinating travel and tracking attendee details, TROOP brings everything together in one easy-to-use platform so you can save time and focus on what matters most. Visit leaderassistant.com/troop to learn more. Hey friends, it's Jeremy Burrows, host of The Leader Assistant Podcast. Thanks for tuning in. Today I'm actually excited to put the spotlight on my friend Jess Lindgren's podcast called Ask an Assistant. Jess takes questions from you all and then answers them on the Ask an Assistant show. So be sure to go to askanassistant.com to check out more episodes and submit your questions for Jess. I hope you enjoy this spotlight episode of the Ask an Assistant show, and we'll talk to you soon.

Speaker 3 · 1:13

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

Jess · 1:41

Hello, and welcome to another episode of Ask an Assistant, the podcast for executive assistants and the people that love us. I'm your host with the scratchy throat because her nieces and nephews finally gave her her first cold of the fall 2024 season, Jess Lindgren. Let's get to work. Today's question comes from esteemed colleague Bridget, who asks, Hey, Jess, can you share some of the weirdest requests you've been given? I know I always say this, but I really do love this question a lot. Mostly, I think that I just love hearing from any and or all of you at askanassistant.com, but this question I particularly do enjoy. I love creative thinking. I love creative solutions. You give me, whether it's a budget, an amount of time, a deadline, you give me a project. I just cannot stress just how much I love getting to do something, quote unquote, weird. Yeah, it just... Okay, so full truth, full disclosure, I do not love a last-minute request. Harkening back to Ask an Assistant episode, looking at my spreadsheet, number 17, you can get things good, you can get things fast, you can get things cheap, but you can only pick two. Last-minute requests, by definition, they're gonna be fast. So since you've already picked fast out of the three of the good, fast, cheap pyramid, if you will, you're not gonna get good and cheap. Because again, you can only pick two. Good, fast, cheap. It's gotta be fast. You have to sacrifice good or cheap. More often than not, it's cheap that hits the cutting room floor. And also more often than not, the result will be good enough when with a little more advanced notice, things could have been good leaning toward better, and they could have been cheaper. You know, so like, I can pull things out for a last-minute request. I have many, many times, as anyone out there who's an executive assistant has. But just, I prefer fast to be the thing that we are sacrificing. I prefer to get things done far enough in advance so that we have better choice, range of choices, we have better pricing available to us. All of that said, I digress. We talked about Good Fast Cheap back in Episode 17. You can go listen to it if you want to. I'll even throw a link in the description to that episode. Make it easy on you. Also, Ask an Assistant 17 pops right up. Anyway, back to the matter at hand. Here are some of the requests that I have handled over the years, some of the weirder things that I've handled with a smile on my face. I do want to throw a few disclaimers out there before we get going with this list. One, I definitely consider these to be good weird. These are things that flex a creative thinking muscle, the creative thinking, the creative solution, the outside of the box way of getting things done. These are good weird things. Disclaimer two, personally, I love a mix of personal and professional tasks. I also talked about that back to the spreadsheet, which I have already moved away from. Time split talk. Okay, time split talk was episode six. I will also throw a link to that in the show note description. So I love a mix of personal and professional tasks. I know that that's not everyone's cup of tea. You're all going to have to make a decision about the 50-50, 60-40, 70-30, 80-20, 90-10 or 100 percent. However, that split is between personal and professional tasks. I love a mix. And that's going to come through, I think, in some of the things that I'm going to talk about here. And then three final disclaimer, I have been working with my present executive since 2020, like, exclusively with him. I just restarted my business this year in 2024 to support the operations of the podcast. I do not presently have any other clients that I am doing executive assistant work with. So yeah, I have been exclusively working with him since 2020. I did have several clients on a freelance basis from 2014 when the company started through 2020, so about a year after I accepted a full-time role with my executive. And I had a couple of long-term executive and or personal assistant roles pre-2024. Looking over my notes, my little list of the tasks that came to mind, I want to say one, maybe two of these are from my time with my present executive. You know, confidentiality and discretion are very important in any executive assistant role. I do feel like I am giving you some examples. Again, these are good weird things. These aren't like bad weird, like we're breaking any laws or doing anything morally questionable. These are just things that are creative thinking exercises, creative thinking solutions, just problems that have been thrown my way that I really enjoyed solving. And I'm not going to tell you exactly which one belongs to which executive or client. So without further ado, here are some of the honestly weirder things that I've tackled in my 20 plus years as an executive assistant. One thing that I did somewhat recently is I placed the same photo order five times. So exact same photos, five separate charges, exact same amount using the exact same coupon code. I had to call ahead and confirm with the store so that they didn't call me first or just decide not to print all five orders because it was five the exact same thing. So letting the store know that it was not a mistake, letting the financial professionals in my life also know that it wasn't a mistake, letting my credit card company, corporate credit card rather, know that it was not a mistake. Mostly, I did this so that there's a couple of reasons here. One, then I didn't have to be the one collating the photos, getting fingerprints all over everything. And it was really nice that everything came in its own separate box so I could just put the personalization that needed to go with the photo order, you know, whatever else went into the box, whether it was a note, another gift, maybe a photo album, that kind of thing. But then everything was just ready to go and could be easily shipped out to the people that they needed to go to. In a similar vein, I collected quotes and photos from a client's group of friends and family. I got everything printed. I bought a bunch of super cute and fun craft supplies and made a scrapbook for someone I had never met. It was a birthday scrapbook and it was a lot of fun just like kind of getting to know this person through the little personal anecdotes and stories that people sent in. But yeah, very interesting and I am not like a scrapbook-y kind of person, but my client asked and I figured I could give it a shot. And it was a really fun, truly creative thing to get to do. And my client loved it and the person that they gave it to also loved it. I found out after the event. So yeah, that one was definitely one of the more creatively challenging things for me personally. I think some people are just really gifted at making beautiful scrapbooks and putting all that kind of stuff together. Like I definitely had fun buying all the supplies and doing it, but it felt more of like a technical project for me than like an actual, I'm going to make this gorgeous. I'm going to handwrite everything, make it perfect. I was very glad that the client was willing to accept printed captions rather than things needing to be like perfectly handwritten. But again, very fun and very satisfying that the person who received it loved it and still has it to this day. So very, very cool. On another occasion, I got my executive and their kids, the last hotel room available in an East Coast state. And this was during peak thunderstorm season, which I want to say is like August, September. It's been several years since I did this, so I don't remember the exact date. But definitely the time of year where huge thunderstorms just come rolling through the Northeast. And yeah, flights get canceled as a result. And I am talking like calling progressively further away from the airport without sending them to another city. I almost ended up sending them to another state, honestly. Because when you're in a major East Coast city and thunderstorms roll through and all the flights get canceled, you just kind of roll with it and do the best that you can. I ended up spending my night, like I said, calling around, finding literally the last hotel room that was available before looking at sending them to another state, spent time rounding up food, clothes, toothbrushes, because it was pretty late by the time the flight got canceled. So there weren't just like restaurants available. And then my executive is in a city with their kids. And not knowing the area and not wanting to go around to four, you know, it was way easier for me as a single person to go round up all the things that they needed because their bags were stuck on the plane. You know, everybody's bags ended up getting delivered a few days later. But yeah, like they couldn't get to any of their things. So I had to get them food, clothes, toiletries for a group of people. It was just really wild. I also had to that same night work on getting them home the next day, you know, because when the thunderstorms roll through, hundreds, if not thousands of people are impacted. Everybody's in the same boat trying to find a place to stay, trying to get the next best flight home. And that's how I spent my night in making it happen. Thankfully, I was in the same city as my executive at the time. We had been there for an event. But it was just a very... I was very glad that my executive was able to spend their time focusing on their kids and didn't need to focus on all of the logistics of it. And it did all work out, you know, obviously, this is years ago. And we're all still standing. But definitely a very interesting problem to solve that very much had a... This has to happen now. Make it happen. This was quite a long time ago. This would have been 2013. I had someone ask me to find a cigar lounge where they could go have like a dudes meeting. Like this was my executive's direct request. Like me and my dudes want to go smoke cigars and drink scotch. And they were just convinced that I wasn't trying hard enough to find them a cigar lounge where they could go. Again, this is 2013, where they could go indoors to drink alcohol and smoke cigars like the person would sell them a cigar.

Jeremy · 14:27

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Jess · 15:27

And just let them smoke it. And the Indoor Clean Air Act was enacted in the state of Minnesota in 2007. So six years prior, this was outlawed. I had to spend time proving that I had researched not only the Minnesota Clean Indoor Air Act, but also that I had exhausted all options for someone to sell my executive and their dudes some cigars and some scotch and let them smoke it indoors. I was just like, hey, if you're happy to have everybody over to your gorgeous home and do that, I'll get you somebody. Like I can find you a person who will like come to your home and roll you cigars and let you smoke them and bring you a bottle of scotch. But like you literally, you can't do that. No indoor facility is going to let you do that in 2013. Ask me in 2006, maybe. But we weren't working together then, so not my problem. But that was a fun one, like proving that I had done the research and being like, listen, this is literally against the law, you can't do this. On a different occasion, I got to choose and hand deliver a cat tree to an Instagram famous cat. Later, I got hired by the owner of the cat to take the cat to the vet. So that was an exciting, that one was really fun. I'm gonna have to dig up some photos and maybe even find the kitty's name because I don't remember his name off the top of my head, but that one was really fun. Just like they contacted me out of the blue, they were like, hey, we need a new cat tree. And I was like, hey, this thing, I mean, this thing called the Internet exists, but like, I'm happy to do it. If you're paying, I'm happy to do it. So it was really cool. Sweetest cat on the face of the planet. He was big, he was floofy, just a little sweetheart, and it was a lot of fun to get to hang out with him and then take him to the vet. On yet another occasion, I have, I've stayed at clients' homes. I did write down on my notes that I stayed at a clients' home during a day to oversee a plumbing installation. I have been there for housekeeping. I've been there to pack and unpack luggage. I have gone to my executive's home to pick up. So like if they had back to back trips, I have gone to their home to pick up the luggage for trip number two, meet them at the airport, swap out luggage, take their trip number one luggage home, and give them trip number two luggage. All kinds of stuff that involves being at executives and clients' homes. So yeah, but again, you know, it's weird, it's different, but it's good weird. Honestly, like we'll talk about this in a future episode, but I really think that anything that helps my executive do their job better is something, and is not illegal as we just touched on with the cigar and the indoor air act thing. Not doing anything that's against the law, not doing anything that doesn't sit right with my own moral barometer, if you will, moral compass. But like anything that helps them do their job better and is within good weird bounds, I'm happy to do it. But again, we'll talk about that in the future, because I know that that's not everyone's deal to want to do a mix of personal and professional, and everyone's boundaries are different and valid. There's no problem with that. But just these are some of the things that I have considered good weird. This one, this one always makes me laugh. On several occasions, and I worked with this person for several years, so it wasn't like I was going every other day. But just on several occasions, whenever my executive's child needed to miss school, they were sick, they were traveling, whatever the reason might have been, going to pick up the homework. This was many years ago. So like kids today have apps and maybe like a special folder where all the homework communication goes to and from the student, the school, and the parent. You know, this was back in the day again. I've been doing this for 20 plus years now. So this was quite a while ago. But I used to have to go to the child's school to pick up homework anytime that they missed. And my executive insisted every single time that I needed to drive their Escalade instead of the company van because I couldn't be seen rolling up to the school in a minivan. Like they really needed me to keep up appearances and drive their Escalade. And again, this was maybe mid to late aughts. So the Escalade was very fancy. And definitely it had a rear view camera. And at that time, that was like the height of luxury. Also very nice to have that rear view camera because if you have never driven an Escalade before, holy buckets. It is really helpful to not have to like reach around, put your arm on the passenger seat. If you can even reach it in an Escalade and crane your neck around and like guess that you're hitting the right marks, oh my gosh. Super fun driving that car, but definitely very weird to have to be keeping up appearances at the kid's school by driving the family Escalade. Winding down the list, I've got just a couple left here. Once upon a time, I consider myself a very good gifter. This one stands out to me as a particularly special one. I was tasked with researching a client, a prospective client. I found out through doing a little bit of digging that they were like a vintage aviation nerd. I ended up buying them a pin that happened to be a replica of an airplane that they owned. And my executive ended up landing the client, and the client later told us that the pin was a big part of their decision to work with us. So again, just like a super unique challenge, and one that really paid off and one that I still just remember to this day, like getting to do the research, finding the pin, buying it from a seller on eBay, having it delivered, getting it wrapped, and getting it to my executive, only to have us land the client, and some pretty important work was very cool. And then the last one that I had on my list here is I found a store. Again, this is the Goodfast Cheap. Hey, my cat is here. Normally not allowed around when I am recording because he is a little turkey and loves a microphone, but he is here with us. Hi, kitty. I found a store that could sell me 20 specific microphone models. Again, if I'd had a little more advanced notice on this, I could have bought them from a retailer that would have given us a better price and could have had them delivered directly to the event site instead of needing to make a special trip myself, but got to love that mileage and the event ended up being super fun. But found a store that could sell me 20 specific microphones same day and personally drove them from San Diego to an event in Orange County. Again, good, fast, cheap, keep it in mind, but love a creative solution, all the things that I talked about, glad that they all worked out in the end. I'm sure that there are plenty of others. Eight, eight. You want to say hi to everybody listening, Kitty? I hope you can hear him purring. He loves all of you very much. I'm sure there's plenty of others, but those are the ones that came to mind in the moment while I was sketching out some notes for this episode. Winding things down because my cat is absolutely going to continue clawing at my microphone. I am not in the podcast closet. I am recording in my room because again, that scratchy throat, not feeling 100 percent, don't want to go sit in my cold podcast closet to record. I'm recording with a wireless lav in my room and winding things down. There you have it, Bridget. I really hope that that answers your question. I would love to know what the weirdest requests are that you've received. Lay them on me, askanassistant.com, give your kitties a little snuggle, stay hydrated out there, all of my beautiful, wonderful, esteemed colleagues. And until next week, take care. All right, kitty. All right, Mr. Man, I hear you, I hear you.

Jeremy · 24:42

You're listening to The Leader Assistant Podcast.

Speaker 3 · 24:55

Please review on Apple Podcasts. gobullos.com.

Jeremy · 25:10

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