Jess Lindgren is a longtime C-Suite assistant, and host of the Ask an Assistant podcast.
In this Ask an Assistant spotlight episode, Jess talks about planning a company holiday party well in advance.
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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
Jeremy Burrows 0:00
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.
Podcast Intro 0:34
The Leader Assistant Podcast exists to encourage and challenge assistants to become confident game changing leader assistants.
Jess Lindgren 0:58
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. Jess, Lindgren, let’s get to work. This week’s question comes from esteemed colleague Rosa, who says, Hi, Jess, I have just taken over. Well, not exactly taken over. I have been handed the responsibility of taking over the planning for our company’s holiday party. The person who used to be in charge of this has moved on to another role. I have no idea where to start help. What do I do? Party planning is not my forte. This is not something I have a ton of experience with but I am open to learning. Any pointers and guidance would be appreciated. Rosa, I know I say this all the time, but I love this question. I really do. I love holiday party planning. I love any kind of party planning. I love party planning at home, all the way through party planning for hundreds, if not 1000s of people, and by party, I do mean more event planning than anything. Doesn’t necessarily have to be a party, but today we are talking about company holiday parties, and it is presently, early to mid September. This might sound a little wild, but start now like truly, especially if you are starting from a place where the person who used to plan the party has moved on to another role, whether it’s within the company somewhere else, get started now like you would be surprised if you’ve never done this before, if you’ve done this before, you would not be surprised you know that the prime venues are snapped up months, if not years, in advance. Start making those calls. You could, even if you don’t love party planning and you don’t want to do it, or you don’t have the bandwidth to do it, make a case for hiring an events professional to help you do it. That can certainly be part of your holiday planning, budget and journey. But truly start now. It’s early to mid September. Start making those calls, start making those site visits, start sampling those menus, go places. Let them treat you a little bit. But start early, because those events professionals at the venues are busy. They are already booking parties for everybody else, so don’t don’t wait, truly is the first piece of advice, and maybe even before you start making those calls and taking those site visits, see what you can salvage from any kind of vendor, lists, contacts, anything from last year that’s going to be the first place that you want to start. Hopefully, the person who has moved on from the company, it hasn’t totally thrashed all of their files just yet. Maybe it’s something where you can dig through some sent emails. Maybe if this person had another person inside the company that they worked with on kind of a holiday party committee, or whatever you might want to call it internally, start there. That is the very first place that you want to start after that. What I’m going to recommend is that we go back to ask an assistant episode 14, which is the who what, when, where, why? Of it all, and sometimes how. So breaking down a holiday party into those steps, the who what, when, where, why? It really depends on your company. How many people do you have? Is it all local people? Is it people who you maybe you have a handful of remote people? Is it something where maybe you’ve got folks spread all across the country and just a couple of central ish office hubs? Maybe you have a New York, a Chicago and a San Francisco? Is it something where you’re a global company and you need to be in charge of or have input in several holiday parties we’re. Really depends on your industry and the scope of your company. So I’m going to use a couple of examples that I am actually familiar with. So one of the roles where I was in charge of holiday party planning, I worked at a company called Anaplan. We had about 650 global employees at the time that I was in charge of doing a holiday party we had. I honestly don’t remember what the breakdown was in terms of global like, what the three regions were. It was America’s EMEA and APAC. I don’t remember what the breakdown was, but I feel like we had, let’s just say, for sake of conversation, about half so about 300 of those people, give or take, were based in the United States, whether they were at the company headquarters in San Francisco, at our Minneapolis office, we had a tiny little hub in Chicago and a nice little hub in New York City, but folks had the option to come to Minneapolis and San Francisco were the two kind of bigger, more established office presences. So anybody in the United States had the option to be flown into either of the parties or just not have a party. So you kind of have to decide who it is that’s involved in your party, whether, again, that’s all local folks, if it’s remote folks, if it’s global, folks you know, figure out, talk with your stakeholders. If you will definitely involve accounting in this, any kind of person who is like Office leadership, especially if you’re dealing with multiple locations, you might have kind of mid tier leadership at your location, and some of the higher ups might be located in another office. So just figure out who, the who is in all of this, honestly, as the person planning the holiday party, I was of two minds when it came to the remote employees. I thought it was really cool that the company made space to make sure that remote employees were given the option. But it also, you know, depending on where somebody was coming from, it might be a multi stop, it might be a seven several $100 flight. It might be a two to $300 hotel night, plus, you know, per diem, all that stuff. So depending on where somebody’s coming from and just how bad travel is at the time that your holiday party is booked, you might be looking at like 1000 bucks, if not more, per remote employee to bring them to a holiday party. And I definitely had leadership kind of, kind of, you know, what? What am I looking for here? Barking in my ear, you know, just really nipping at my heels to keep the rest of the party in budget. So it felt really strange to have like, a $1,000 or more travel budget per remote employee, plus party budget. And then anybody who’s local, you know, I asked for any kind of wiggle room, that kind of thing, like, can we go a little bit above in this area? Could we reallocate some funds? And they were like, no. So it felt really weird to have all this money to bring remote employees in, but then have senior leadership say, No, we couldn’t go over on the party itself. So definitely keep that in mind if you’re going to be flying people in for the party where that makes your budget come out in the wash at the end. And again, I know I say this all the time, but like, talk to your financial people, talk to your legal people, make sure that everything is being covered. Maybe, if you do have remote employees, maybe it’s something where folks just get 150 or $200 or since folks locally would be allowed to have a plus one, if the budget, let’s just say, is $150
Jess Lindgren 9:01
per person, maybe instead of flying folks in for the party, you give them the option of kind of a party for two, whether that’s a like a couple 100 bucks, you know, one to $300 to go to a favorite local restaurant, or maybe there’s something more, like a generic like a DoorDash or something that involves a little bit less coordinating from your end. But something to keep in mind when you are working with remote and local employees, that the travel budget is not cheap, especially in December, and especially if you were going to send somebody like, we had a like, essentially a WeWork office in Chicago and New York, so not really a physical office where a party was being planned. If you’re taking somebody from New York to San Francisco in prime holiday travel like that gets expensive, so it might even be something like we’ll get to this at the end. Like all the reasons why it’s great to bring people together, whether they’re remote or local, but it definitely. Should be a factor in your decision making. So just depending on your budget, depending on your leadership’s wants and desires in terms of bringing everybody together, that’s your Who is it? Everybody? Is it? Just local folks, something in between. Figure it out onto the what it’s a holiday party. There’s definitely options. Anything you can do something kind of unique, like if you live in an area where there’s something really cool and interesting that happens in your area, whether it’s around holiday time or another time of year, and this kind of bleeds into the when of it all. I touched on this a little bit. December is a super prime travel time. So depending on what it is that you choose to do, maybe there’s some world renowned performance art of some kind that happens where you are, or maybe there’s some Michelin star chef, depending on what your budget is, it can be something super unique. It can be something kind of your more traditional venue, food DJ, Photo Booth kind of thing. But figure out what it is that you want the theme to be, the tone to be, the actual bones of the party, and go from there, and even if you do end up being kind of the only person who is in charge of making the party happen, definitely get some feedback from your local leadership, because, yeah, you just it’s it’s tough to be the only person making the decisions, and then have folks not really like what you chose. So it’s really good to get some of that input. And folks know their teams. They know their spouses or plus ones, people that might be coming and what they might like to see out of a holiday party. So moving on to the when, again, December, it’s peak time. It’s time where kids are off school, things are ending early. It’s dark, super early for a lot of the country, in the United States, and if you live like in Europe, you’re pretty far north, like it gets dark, super early. So figure out when it is that you’re going to do it. December can be very expensive. December is also very full, so you might have a hard time getting buy in from people if you pick a Friday night in December, but you might also have a lot of really disappointed employees if you don’t pick a Friday or a Saturday night in December. So just you know, do your best. You’re never going to get 100% buy in. You’re never gonna get 100% of people super thrilled with the who and the what and the when that you chose, but just do your best, you know, send out a little poll. Hey, these are the dates we’re considering. Does this work for you? And or a plus one? It can really be more expensive. It might also be something, though, where you’re kind of you have to spend the money during the calendar year. I don’t 100% know how fiscal year budgeting works, so I’m going to look into that for a future episode. But just depending on how your budgeting works, it might be something where you need to spend that money in December before the year is out. Or it might be something where you can kind of fudge things and move it into the next year. January, you’re going to have a lot more choice. January is typically a very slow season for a lot of service industry professionals, something where, like, you could really have your pick of restaurants, event venues, pretty much any day of the week. And your employees might really appreciate being able to do something to, you know, celebrate the holidays, but also kind of the start of the new year. So again, definitely pull all of your people make sure that you’re covering your bases as well as you can. But December, January. Figure out what’s best for you, best for your company, best for your budget. As to the Where do you need it to be? Something close to the office? Do you need it to be downtown, in the CBD, the central business district, or does it need to be in a suburb? This is another thing where you’re going to get different availability, different price points, depending on what part of town you go to. If you’re somewhere like a downtown parking, you know folks are going to have to potentially pay to park unless you’re able to secure a venue that has parking attached, unless you’re able to hire a valet for all of your guests. Something I would really love to recommend that you do is budget in safe travel back home for anybody who might be drinking Lyft gift cards or Uber, if you must, not that expensive and way better for everybody than getting charged with a ticket for driving under the influence. Yeah. Um, so it’s a really nice touch, too. It just shows your company, uh, shows your employees that you are caring about them, their well being. And, yeah, it’s just, there’s, there’s no downsides to it. Just make sure that everybody can get to and from the party safely. Um, why the why of throwing a company holiday party, it’s great to celebrate, especially at the end of the year, or if you are going to do a January great to start the new year after you’ve just done, you know, four to six weeks of holiday celebrations. Things kind of start to pick up right before Thanksgiving, and family stuff really doesn’t die down for a lot of people until after the start of the new year. So again, whether you’re doing January, or, excuse me, December or January, it’s a great way to celebrate. It’s a great break for your team. It’s good team building, like it’s just great for everybody to get together, especially if you do have some of those remote folks who are going to be flying in, people that you might see a lot on video calls, or once in a while when your department gets together, having everybody together over the holidays. It’s great for team building, great for communication, great for building those relationships at work and outside of work, if that’s what you’re into. It’s great for staff retention. It’s a total bummer to be like, especially using Anaplan again as the example that I know. So it’s the example I’m going to use Anaplan at the time I was there in 2014 to 2016 it’s a SAS company software as a service. And it, it was the first time I had actually worked in a SAS environment. And it seemed very, very par for the course that you would have a big blowout Christmas or holiday or end of the year celebration in some way, shape or form, you know, so that can really be a bonus for people, as they choose to work at your company and stay at your company. It’s a drag to hear that a company maybe isn’t doing well enough, maybe didn’t set aside any budget for a holiday celebration, especially if you have friends and colleagues who have moved to another company, kind of in the same industry, and, yeah, definitely a nice touch for folks, not a make or break kind of thing, but definitely something that I think a lot of people really look forward to. It’s something that where your company and or your individual department, depending on how you all roll, can use the holiday party as a way to create traditions. You know, something where every year everybody from the sales department goes out before the holiday party or something. I don’t have a great example off the top of my head, but it can be something where there’s just a traditional maybe you hosted the same venue every year, and then you get different entertainment, different food, or you have, like the Dundies, like using the office as an example, you have a little inter office, either it’s the office Olympics or the Dundies, you know, some kind of superlative awards for people.
Jess Lindgren 18:18
Definitely, a lot of options for you to create traditions, and that’s something, again, that ties into team building, whether it’s for your department or the company as a whole. And it’s also a really great time to foster some community engagement. Over the years, I have done Toys for Tots drives, and I think if, if I’m thinking of the right organization. I think Toys for Tots is the one where, like, you can even have a marine come to your event, like, if you’re raising, you know, bringing in enough toys. And if your local Marines, troop chapter, pardon me, Marines for not knowing regiment. That might be the right terminology there. But it is something where you can have a marine come to your event to collect the toys. You can use it as a fundraiser if you don’t want to do like Toys for Tots or something like a food drive, where you have physical items that you have to take care of. A lot of nonprofit organizations make it so easy these days to just get in touch. Set up a link where folks can donate. And that’s definitely something where you don’t even have to be part of the company to donate. You know, if you have friends or family that are really invested in whatever cause it is that your company chooses to support, whether it’s some kind of bigger overarching charity like the Red Cross is a big one. I really love world central kitchen chef Jose Andreas does some really wonderful and impactful work in areas that experience extreme weather, like hurricanes, tsunamis, earthquakes, that kind of thing. They’re also. Doing some really incredible humanitarian efforts in Ukraine and Gaza. So just some really great organizations that you can get in touch with. They’ll help you set up either whether you know if you need a private link for your company or organization to be able to track how much it is that you have contributed, or you can ask folks who donate to dedicate it to a certain name or in memory of a certain person. You might also pick somebody inside the company, like maybe somebody had some kind of medical or personal family issue, and instead of having your fundraising drive go toward a larger organization, maybe it’s something where you pick, whether it’s an employee or a local community member to to support them directly. You know, a lot of those big organizations, they still do really excellent work. They have often really great infrastructure behind them. The money does go to good use, but when you do find local people that you can support that money, just the effect is amplified, and especially if you’re going to pick one or maybe a small group of individuals to benefit from your fundraising, it just, it’s really great community engagement, stimulate your local economy, and that’s a great way to do it. A couple examples, specifically over the years, things that I’ve done my company gal Friday, 612, everyone gets a plus one to the company holiday party. And everyone when you’re a company of one is me. So my husband really loves it. He loves the annual Christmas party. Holiday Party, we pick a restaurant, whether it’s somewhere that we really love going, that we’ve been already, or somewhere that we want to check out. We take a lift to dinner. We do appetizers, drinks, dinner, dessert, the whole, whole nine yards for two of us, it’s usually two to $300 total. So it’s a splurge, it’s a gift, but it is a lot of fun. So you know, even a company of one, you can still mark a holiday party and really go all out and just have some fun with it, if you’re a small startup. So I worked at a company where I actually got the idea to run my own holiday party. I worked at a company of about 10 people, and we did same thing, just a dinner at a nice restaurant. Everybody got a plus one, and it was the same deal. Drinks, appetizers, dinner, dessert. It is really nice when you throw these holiday parties, if you can take people’s dietary restrictions into account. This is something that I’ll talk about in a future episode in more depth about how to be mindful of dietary restrictions and how to execute that, whether it’s for a group of 220, or 300 600 people, it’s easier than you think, but it just, it’s, it’s kind of a drag when you are going to a holiday party and, you know, let’s say they pick a pizza restaurant and you’re dairy free, like I am, like, you know, you don’t want to feel like a thorn in anybody’s side, but you also don’t want to go to the party and leave hungry. So the other example, just touching on it again, working at Anna plan, I did a couple of different very, very different holiday parties. I did get to plan two parties while I was there. And the first year that I got to plan the holiday party, everybody was just begging left and right, like just Jess we really want to do something unique. We want to do something different. What I ended up doing is I secured us a block of tickets at a local theater production at in Minneapolis, if you’re if you’re familiar theater de le genoon, it’s theater of the young moon, one of my absolute favorites still to this day. I mean, I think I saw this production of hunchback when I was probably a teenager, and I have seen literally 1000s of theater production since, as a grown up, their production of hunchback still is in my top five productions that I’ve ever seen in my entire life. And off the top of my head, I cannot remember what the play was. I will have to look that up and put it in the show notes. But I had the theater like, they have a little event space, kind of up lofted above the the What am I looking for here? Not the stage. It’s up above, like the seating area. They have a lofted area where you can do catering before. Andor after the show. So it was something where we had dinner catered in before the show. We had a big block of tickets, so everybody who worked at the company who wanted to come and their plus one got to sit and stay for the theater production we did chocolate covered strawberries and champagne afterward, and excuse me. And the cast of the show came out to mingle with us. I thought it was really cool, really unique. I never heard the end of it after that party. So it was something that I definitely cornered a lot of the upper management to say, Okay, you all, were the ones who were begging me to do something unique. I did something unique. It didn’t go over well, I want to do something a little more traditional, if you will, in terms of a holiday party. So I got some really good feedback from everybody about what didn’t work, and turned it into something that totally did work. I rented out the varsity theater in Minneapolis, Minnesota. It’s a wonderful venue, like just gorgeous, perfect amount of space for the size crowd. We had, I would say we had, like, 200 employees, 150 let’s just say 150 employees. And everybody, if they wanted one, had a plus one rented out the venue. The venue has, like, really, it’s set up to be a theater, but it also has some upper balconies, so it’s got some depth to the space. It’s got really beautiful architecture inside of it, some really gorgeous finishing touches, like the railing around the upstairs balcony is gorgeous. It’s got some comfortable furniture upstairs. I hired Jake rude. He’s a local Minneapolis DJ. He does transmission dance nights at First Avenue. He’s also on the current if you’re not familiar, look him up. He’s fantastic and wonderful. Oh my god, if you’re considering a holiday party in Minneapolis, you will not be disappointed if you hire him, like all of your Minneapolis locals will know who he is, and he just knows how to work a crowd, like he did such a great job balancing holiday ish music, but not going overboard, like it was just a really great ambiance and really, really added to the overall quality of the party.
Jess Lindgren 27:31
The Varsity also had really excellent food. So it was just something where folks it was. I think I did past appetizers more than like a sit down dinner and then an open bar, and it just, it went over great. Everybody loved it. Everybody could kind of mix and mingle. A few senior leadership people got up on stage with a microphone, gave a few remarks at various points. It just went over really well. And we hired a really great photo booth. I’ll see if I can dig up a photo from that, because, honestly, I looked amazing. And the photo booth people did a great job. Also, if you’re in Minneapolis, Cadence and Eli fantastic photographers. I don’t know if they still do their photo booth or not, but it was a really gorgeous, really classy setup. They brought really fun props, like, sometimes when you do a photo booth, the props are kind of cheesy or flimsy. They brought really cool, like, I remember specifically, they brought Hulk hands, like those foam Hulk hands, so really quality props. And the background was just like a shimmery sequin covered peachy fabric. It was really beautiful, and the photographer that came did a really great job getting everybody to have fun. So all of that put together the party was a wild success. And Oh. So back to the tradition thing. What I did for everybody’s party gift is Anaplan and varsity have the same number of letters, and if you look up the varsity theater, they have a really cool marquee on the outside of the building. So I took a picture of the marquee, and I worked with a glass etching vendor and changed varsity so in the same font, but changed it to Anna plan. And so everybody got a glass, like a pint glass, with the Anna plan on the varsity logo. And then, you know, Anna plan company Christmas party, uh, 20 probably 2015 because I let Yes, because I left in 2016 like summer of 2016 so this would have been the 2015 holiday party. So I don’t know if they kept that up after I left, but it definitely if I had gotten to plan the 2016 holiday party, I definitely would have kept that going. So lots of options to create those. Little traditions, create memories, create things that your teams all do together, if you’re going to do anything in terms of door prizes, like I’ve been to holiday parties in the past where folks have won airline tickets, they’ve won Xboxes, they’ve won PlayStations, they’ve won $500 in cash. They’ve won gift cards to fancy restaurants. Talk to your legal and financial professionals, talk to your general counsel, talk to your accountant, talk to your CFO. Make sure that rules are being followed. I don’t have any I didn’t plan that party. I just attended it. I have no idea how that stuff gets recorded and written off as a business expense. I just don’t know. So if you’re going to do anything like that, it’s very generous. It goes over extremely well with your employees. I hope you are not surprised to know. But if you’re going to do something like that, just make sure all of your bases are covered, that you’re staying within budget and that any kind of tax rules that might be in effect for your city, state, country, are being followed so Rosa. I really hope that that helped. That’s my big old feelings on holiday parties. Just definitely stick to the who, what, when, where, why, of it all. Sometimes the how is you? So always keep that in mind. Don’t be shy to tag some people in definitely get feedback from your upper leadership, the who, just kind of a brief recap here, the who is all of your employees. Hopefully everybody gets a plus one that definitely makes it a little more enticing to want to attend. So that’s the who is, your employees, hopefully a plus one. The what it’s a holiday party. Make it fun. Who, what? When is it going to be December? Is it going to be January? You’re going to decide what’s best for you, your company, your budget, everyone’s availability, the wear, find the venue that makes the most sense. Find something with good parking, or hire a valet. It is worth every single penny. Make sure that folks can get home safely if anybody’s going to be drinking, invest in those Lyft andor Uber gift cards. And why team? Building tradition, building great way to celebrate a successful year or kick off a new successful year. So again, that really wraps everything up. Rosa. I hope that was helpful. Anybody out there listening? You know, I would always love to hear from you ask an assistant.com Keep those questions coming. And yeah, that’s everything I’ve got for today. So until next week, stay hydrated and take care.
