AAA Spotlight Episode of The Leader Assistant Podcast

Jess Lindgren is a longtime C-Suite assistant, and host of the Ask an Assistant podcast.

In this Ask an Assistant spotlight episode, Jess answers a question about one on one meeting frequency and format.

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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 – 0:29]: 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.

Jess Lindgren [0:29 – 31:25]: 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. Today’s question comes from esteemed colleague Diane who says hi Jess, I just started a new role where I’m supporting the CEO. I’m replacing their outgoing assistant of 10 plus years. And and I want to establish a one on one schedule from the jump. Any pointers? Diane I love this question. It is something that I feel very strongly about that your time every week with your executive, your one on one or one on ones plural, depending on your workflow and needs. It’s some of the most important time that you and your executive will spend on any given week. So I really love the initiative to get something going from the get go. And you’re in a, I mean every single executive to executive assistant relationship is different, right? You’re talking about people in different levels of the company. Sometimes an EA might support a C suite individual, sometimes they might support a director or VP level person. Depending on your organization structure, you might have a president, a vice president, a director, all of whom support up to the CEO like you. Just every organization is different. Every executive and executive assistant relationship is different. But in this case coming in as a new person who is replacing someone of 10 plus years. First off, congratulations on the job. My goodness, the hiring market right now is absolutely bonkers and big, big congratulations like being selected to replace somebody of 10 plus years. That speaks very highly of you and the person that you’re going to be working with. Congratulations. 2 I really again love this question because again this time your one on one is so important. If we’re talking about I’m going to kind of boil it down to frequency and format. Although wrapping up my thoughts about you coming in as replacing someone that the executive has been with for a long time, you’re going to want to strike a very careful balance of replicating what worked with the outgoing assistant. So definitely, if the time is available, have the outgoing assistant sit with you and train with you for a week or two if they can. All that depends on the company’s budget, your executive’s desires and wants. The person who’s outgoing, maybe they’re starting a new job next week or taking a two week vacation to come down from 10 years of supporting one executive before they move on to their next adventure, you never quite know. But if you can get that time, even if it’s something where the company hires the outgoing executive assistant as a consultant for a few weeks or months, or you know, on call, or you have a one on one with them once a week, once every other week, once a month, just to touch in how things are going. Because a 10 year relationship is really long. That’s a very long time to work with one person. So again, you’re going to want to strike a a careful balance between what was working. But as a fresh new incoming set of eyes, it’s also your job to evaluate and recognize what isn’t working and what could use a tweak or some changes. But it’s just any new relationship, whether you’re someone’s first executive assistant, which was my case with my present executive, he had never had a fully fledged executive assistant before. That presents a unique opportunity. And coming into something where the executive is very well established, assuming, guessing, hoping that the company is very well established as well, that presents a unique opportunity as well. So again, just kind of get a feel for what was happening that did work and then definitely take all of that information, do some research into different methodologies or things that you might like, you know, project management tools, Ask other assistants that you might know in other companies what’s working for them, you know, because if this person hasn’t had a change since 2014 or earlier, things have changed in the last 10 years. Technology has changed, the way that we do work has changed, the world has changed quite a bit. So definitely striking that balance between what was working and what new, fresh things are you bringing to the table is a big important piece of it. So when it comes to the one on one itself, the first thing that is the absolute most important is do not let this time slip past you. My one on one with my executive is something that is always flexible. I am happy to reschedule. Whether something personal or professional comes up on my executive’s calendar, we have an understanding. He can move it, I can move it. He sometimes might ask a day in advance, he might ask 15 minutes in advance and it just doesn’t matter. Like my time. I know from 10 years of working with my present executive that he has always prioritized this time. And that was something that I really not demanded, but made clear was not negotiable when we started working together, that a one on one is absolutely imperative to the success of our working relationship, to the success of the business. So just make sure that whatever day time format it is that you choose, that it’s something that is prioritized and is not forgotten about. So in my present executive executive to executive assistant relationship, it’s flexible, but it always happens. So even if Pat, my executive, needs something on the fly, if he needs to change the time, if he needs to change where he’s calling from, that’s fine, but he never skips it. And in past relationships, it was definitely something where we had a one on one scheduled. Let’s just say for sake of conversation, we had a one on one on Monday. And then my executive might come in two hours past when we were supposed to meet and didn’t answer their phone when it was our time to meet. So, like, not only did we not meet by phone, we didn’t meet in person. Oh, I’m sorry, I’m sorry. My morning got away from me. Let’s try for tomorrow. My day is just, it’s Monday, it’s too complicated today. My schedule is too full. Could we look at tomorrow? And then it just kept. The can kept getting kicked down the road and every day there was a new excuse. And then Friday afternoon would come around and I’m packing up for the end of the day, getting ready to leave. Oh, Jess, I need you. Like, it’s so disrespectful of your time. It’s disrespectful of the working relationship. Just make sure that as you come into this new role, or if you’re in an established role and you recognize some similarities there, if your one on one is getting kicked down the calendar, moved day by day by day until it just doesn’t happen, or it doesn’t happen until the zero hour, change it. Stand up, say something. This time is way too valuable for everything. You just, you need that time. It’s time for you to have your executive’s ear. One on one. It’s time for your executive to talk about whatever it is they need from you. Talk about project priorities, talk about performance, talk about what’s coming down the pipeline, what’s coming up next quarter, what’s coming up next year. You know, it’s just time that is absolutely invaluable and needs to be prioritized no matter what. So all of that being said presently, my one, let’s, let’s talk about my present role in terms of frequency. When my executive and I started working together in 2014, we started off with daily, like every day for 15 to 60 minutes, just depending on what I needed because it was a new relationship. I was learning a lot about my executive, a lot about his business endeavors, a lot about the team and supporting members around him, learning about his family. Even though I lived in Minnesota at the time he lives, he lived and still continues to live in California. He had just moved house right when he and I started working together. So just a lot of changes for both of us. I had just quit my last full time corporate gig and gone freelance. And he was my, not my first client per se, but definitely my first big client. I had a lot of small local clients and this was something where I finally had landed someone that needed like 15 hours a week from me. So I had people like ad hoc, bought a bucket of hours from me, you know, a little bit of a retainer and was doing things as needed like hired one offer projects. This was my first big 15, you know, 10 to 15 hours a week and just getting to know each other. And yeah, started off day to day, 15 to 60 minutes just depending on what I needed, depending on what he needed. As we really got to, to learn about each other and know each other a little bit more. As I started to feel more confident and he in turn started to feel more confident in me, we very quickly moved to three times a week. So we would check in Monday, Wednesday, Friday or Tuesday, Thursday, Friday, just depending on how our weeks looked. Eventually, pretty quickly thereafter, we moved to Monday, Friday, check in at the beginning of the week, check in at the end of the week. How’s everything going? Um, and now that we’ve been working together for so long, I would say how long ago did we switch to once a week? It was at least six, seven, eight years ago. Like it really was not very long that I needed multiple touch ins a week. Um, there are definitely weeks where if we have a lot going on, like we just did our big event last month in June. Time’s still a little squishy. It’s mid to late July right now as I’m recording. But like leading up to that we definitely have more check ins as needed. But on a typical average run of the mill week, we touch base once a week for a maximum of 30 minutes and usually it’s more like 15 to 20 minutes. Just because 10 years of working together, I know how to respond on his behalf. I never pretend to be him. I always say hey so and so. Hey Diane, Jess, here on Pat’s behalf, here’s the answer to your question. If you need further information, please don’t hesitate to reach out. Like just providing that piece of information that they need that Pat does know. But it’s my job to mitigate distraction for him. It’s my job to keep the business running behind the scenes so that he can be the person on the podcast on the YouTube channel in front of the scenes. And that actually reminds me of something that I read a long time ago. Let me just find this real quick. Let’s see here. Okay, this is from Priority va. So va like virtual assistant Priority va. Trevinia Barber, she used to write a really excellent blog. I do not know how old this piece is. I feel like I read it forever ago. But I’ve also lived a lot in the last 10 years, like we all have. I don’t have an exact date on this, but basically the piece says your EA should be a gateway, not a gatekeeper. And some of the stuff that she touches on in there is a gatekeeper is someone who keeps others out. They guard the executive from their team and clients, which honestly I think gives EAs kind of a bad rap as being judgy or defensive or hard to work with. Many executives think of their EAs or want them to behave like a gatekeeper. And I really love Trevinia’s perspective of inviting your VA to serve as a gateway. Your va, your executive assistant, your virtual assistant, whoever it is that might be on your team. On my podcast here, obviously we are leaning more toward executive assistants, but I think there’s a lot of bleed over into lots of different roles within an office. But basically, Trevinia’s piece is kind of what I even touched on in my little made up example of hi Diane, here’s the answer to your question. That’s a gateway. So instead of saying, yeah, let me just get back to you in a week with the answer after I’ve spoken with my executive. No, I know the answer right now. And instead of waiting for my executive, instead of adding it to their pile of tasks for the day, week, month, year, it’s something that I can take care of in the moment and then it doesn’t have to make it all the way to my executive, but when the need arises, the leader is always available. Like but it has to go through your executive assistant as that gateway, like just kind of a first filter on the information. And by empowering your executive assistant to act as a gateway rather than a gatekeeper, it just, it’s empowering on so many levels. It boosts your executive assistant’s confidence and ability to, and desire to frankly take on more responsibilities within the business. Most executive assistants are detail oriented powerhouses. So if you tell us the answer to something once, six years from now, we will remember and be able to just answer it from the hip. So getting back to the one on one of it all though, it is something where you filter out that first level of information, you get that time with your executive again. With so long working together, Pat and I have been down to one day a week for several years now. We’ve tried everything. If we’re. I’m getting more now into the format. So I hope what every, everything I’ve said for the last few minutes covers the frequency piece. Definitely start with more frequency to begin with. It’s a big, a big investment of your executive’s time from the start, but it’s definitely worth it in the long run. So getting into the format, my executive and I have tried every day of the week, literally Monday through Sunday, we’ve tried mornings, we’ve tried midday, we’ve tried evening. Um, I think the one that was the worst honestly was when we were doing Sunday nights. Um, it kind of had both of us in a, like a Sunday, you’d start the day feeling good and then as the day crept on, like even though it was 10pm Pacific, when my executive might be in his office anyhow, he might be working on passion projects, he might be doing something for his family and just needs the privacy of a closed door where work typically happens. Like it. Just doing it Sunday night had us both kind of tensing our shoulders and starting the work week a day early. So my advice would be unless it’s absolutely necessary or unless your weekend is like Thursday, Friday and then Saturday, Sunday are your work days. But if you are adhering to more of a four or five day Monday through Friday, Monday through Thursday workday, Sunday nights were just terrible really. And it took us, I would say like six months of doing Sunday nights. Like it was definitely a time we were Both always available 10pm Pacific. And that worked perfectly when I lived in Minnesota and when I lived in California, we’re both night owls. So the 10pm timing was fine, but it was just kind of the psychological cue of it being Sunday really didn’t work for us. Mondays are okay, but depending on what came in over the weekend, I might not be ready on a Monday for the one on one. Like I may not have gotten all the way through the inbox and all the requests that have come in since I logged off the last week or if I took a long weekend or if there was a holiday. Like Mondays are tough, at least in our experience. Tuesdays have been absolutely ideal. Like that has been my sweet spot for probably two, maybe three years now. Tuesdays are great because it’s not Sunday night. We’re not jumping into the work week prematurely. It’s not first thing Monday and my executive has a lot of like internal and recurring meetings that are set on Mondays. So it kind of takes him out of his flow as well. And just Tuesdays have worked really well with very minimal. You don’t have a lot of holidays in the United States on Tuesdays. So there’s not a lot of holiday related reschedules. Travel, you know, he might have a fair bit of travel where he comes home on a Sunday or a Monday. So it has been really great and working really well for us to be a Tuesday morning Pacific Tuesday, late morning to mid afternoon to even honestly 6pm eastern for me on the East Coast. So yeah, Tuesday has just been really great for us to kind of miss that Monday onslaught. Give us time to settle into our week, give me time to get through everything that might come in over the weekend and on Monday, honestly. So Tuesdays have been great. Wednesdays are fine. That’s the day we typically reschedule to if a Tuesday doesn’t work for whatever reason. Thursday, I mean we’ve had a four day workweek for at least five years. Question mark. I’m not 100% sure on how long it’s been, but I know it was, I feel like it was pre pandemic. So I feel like it might have been 2019 or 2020 that the four day work week was instituted. I’ll have to go back in our records and figure that out. But Thursdays for us, that’s our Friday. So like we’ve already been through an entire week by Thursday. And if we were working a five day work week, which many of us do Friday, what, what does that help you that helps you go into the weekend or like with, with a huge to do list sitting on your shoulders or it gives you however many hours of cram time before you leave. So instead of things winding down on a Friday afternoon, you might get a whole new onslaught of tasks that have Give you a stressful Friday afternoon or like I said, just kind of has your mind thinking about what are things going to look like on Monday? Because I just got a huge pile of things to do on Friday. So yeah, Tuesdays work for us. It’s never more than 30 minutes unless we have like a ton going on. Um, and typically, like I said, It’s 15 to 20 minutes max. We have also tried every manner of format. We have tried scheduling Zoom calls, we’ve tried Skype. We’ve tried meeting inside of Slack on, I think it’s called Huddles. All of that has run into like the number of times where we’ve fired up our Zoom and either or both of us needs to run an update on Zoom. Skype, for whatever reason isn’t connecting or the sound quality isn’t good. So it’s constantly like, huh, can you repeat that? We honestly, for probably the majority of our 10 years together have been just talking on a phone call. Then there’s no pressure for either of us to be camera ready. There’s also way less possibility of technical issues if it is something where one of us is in a particularly poor location for cell phone reception, which honestly Southern California, bad cell phone reception, lots of peaks and valleys that can put you in really funky dead spots. Like, we had an office for a while that literally no cell phone service and we were paying like a thousand dollars a month for Internet and it still wasn’t great. So every so often you do find yourself in kind of a cell phone dead zone. And those are the times where we’ve pivoted and just, hey, my cell phone isn’t working. Can we hop on something else? And then we just do a quick pivot, figure out which service is going to serve our needs in the moment. But I would say at least seven, eight years we’ve just been hopping on a quick phone call, which is great because I can, I always prioritize being at my computer. I have my little one on one spreadsheet which I will make available in the templates on ask an assistant.com and it’s literally just a two column spreadsheet. Who and what do they want? So who. I always take the email address of the person requesting. Depending on your company, that’s something where you might largely deal with internal stakeholders and fellow esteemed colleagues, if you will. But in the industry that we’re in, it’s. We’re a team of two. It’s just me and my executive. And so we almost exclusively, if it’s not the Two of us talking with each other, we’re dealing with external stakeholders. So speaking engagements that he’s going to attend, people that we’re partnering with for a YouTube video, an event that we’re putting on, or an event that he’s attending. Like, it’s almost exclusively external people. So I always pull the email address, put it into my spreadsheet so that satisfies the who piece. And then the what do they want? Is just an executive summary. So somebody might send me several paragraphs of information about what they want. And then instead of having my executive sit down and need to read and then distill all of the information, I read it, I distill it, I make a one to two sentence executive summary to get the information or the approval that I need from my executive to take next steps. And then my executive can do whatever he wants during our one on one. If he’s going to be sitting at his computer, great. We recently had a one on one where he had a speaking engagement in Las Vegas. Las Vegas is not very far from San Diego, so he drove. He was literally like, hey, Jess, can I put you off for like two hours? I just need to wrap some stuff up before I leave and then I’ll call you from the car. So it just. My husband and I joke about this all the time. Living in the future is the absolute freaking best. It is the best to live in the future and be able to A, push the call off by a couple hours, B, be able to live in a different state from my executive in a totally different time zone and just have it work. And C, take the call from my executive while he is in his car calling me. From his sunglasses. He’s got a pair of those, like sunglass, I think they’re like bone conduction headphones and they might have a camera feature included. Like, it’s just wild. And it’s honestly some of the best, crispest audio I have ever heard. I really need to ask him what those are so I can get a pair myself. Anyway, plenty of times where he’s not necessarily on a road trip to Las Vegas, but he’s walking the dogs in the neighborhood. He’s running to the UPS store to pick up the mail. He’s doing any number of things super flexible for both of us to just be able to hop on a phone call and not worry about the technology piece and make sure that our systems and apps and software and everything is up to date. Like, it just works. So in conclusion, Diane, definitely strike that balance between what it is that worked with the previous assistant, but also kind of like, put your own spin on it, pave your own way. Make sure that you are not just a carbon copy of the person who left. You are your own person. In a previous executive assistant role, I took over. My name is Jess. Jessica, but I go by Jess. And the previous assistant who I took over for, her name was Jessa. The number of times over the first year that I worked at that company where people called me Jessa was absolutely infuriating. You know, easily understood, but still infuriating because we are very different people, very different working styles, very different look. Physically, she was a very lovely blonde lady. I am a very lovely redheaded lady. Like, we look nothing alike, sound nothing alike, work nothing alike. So definitely put your own flare on it, but strike that balance. Pull in some things that used to work so that there’s still a familiar framework for your executive. Ask them, and as politely and diplomatically as you can, demand that they make a big investment of their time at the get go. The number of people over the years who complain about feeling totally out of their depth or unsupported or like they don’t know what to do or like they haven’t been trained, because people assume that an executive assistant can just come in and figure it out. Like, yeah, we can come in and figure it out, but we still need positive reinforcement. We need somebody telling us that we’re doing good work and that the decisions that we’re making on the fly as we learn more about our executive and the company environment that we’re in, like, we need positive reinforcement for all of that so we can continue to feel empowered and learn and all that good stuff. So, yeah, it’s just. It’s going to be a big investment of time from your executive from the get go. Definitely see if you can’t get that outgoing assistant to also provide you some training. Again, whether it’s time right up front, maybe you can overlap each other by a week or two. Maybe the old assistant can come in once in a while until you really feel confident, but definitely move to make that separation. And then after the big investment of time, get into a cadence that feels good, where you feel supported, where you feel like you’re getting the time and attention from your executive and feedback time, attention and feedback from your executive that’s so invaluable and just only serves to further develop your working relationship with each other. Get into that cadence. Like I said, I personally, especially after having done all seven days of the week, Tuesday is awesome. But There are plenty of people out there who still have a day to day. Like a day by day, every single day they might meet for 30 to 60 minutes and that works too. It just happens to work for me and my executive that we meet once a week and then obviously he’s available throughout the week via Slack for anything that I need at any time. But like the time where we really try to get the most out of it and put all of those little bits and pieces that keep the business running and touchstones on projects, we try to do that once a week. He’s always available for more if I need it. And then figure out the how of your one on one. Is it something where you’re working remote? Do you need a zoom call where it’s something that you can record and come back to? Is it Skype? Because you’re that’s just the platform that you use. You’re a Microsoft shop and Skype is just built into every single machine in your company’s infrastructure. Is it something you use WhatsApp because you’re in different countries? Is it something that a phone call will work? Are you in the office together all day, every day and sitting down in the same room is just the best way to make it happen. So Diane, I really hope that all that helps. I would love to know as you dive into this role and grow and develop within your working relationship with your executive and at the company, let me know where you land. Are you doing every day a few times a week? Once a week? Once every. I mean, don’t go every other week. I think it’s very important to touch base at least once a week. But let me know. I would love to know your frequency and format and any input that Diane, you or any of the rest of you listening esteemed colleagues may have. Ask an assistant.com I’d love to hear from you. Comments, questions, thoughts, concerns, lay them on me. And until next week, take care. You’re listening to the Leader Assistant Podcast.

Jeremy Burrows [31:35 – 31:46]: Please review on Apple Podcasts gobos.com.

 

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