Ask an Assistant Spotlight - Jess Lindgren on Task Management Systems

Jeremy · 0:00

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Speaker 3 · 1:45

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

Jeremy · 2:01

Hey friends, my best-selling 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.

Jess · 2:52

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. Today's question comes from esteemed colleague, Debbie, who wrote in via askanassistant.com. She says, hi Jess, do you have a recommendation for task management software? My executive has a dozen different projects going at any given time and it's becoming unwieldy to manage them all. I'm afraid things will slip through the cracks. What have you used and loved and on the flip side of the coin, what have you used and not loved? Debbie, I know I say this all the time. First things first, I thank you so very much for taking the time to write your question in askanassistant.com for anybody out there listening. I would love to hear from you. And again, I know I say this all the time, but I really do love this question. I also work with somebody who has a dozen different projects going at any given time. My executive is an author, blogger, podcaster, YouTuber. He has three active and very well-subscribed YouTube channels at the time of recording. We run live events, we produce a podcast, like just so much going on. And he and I, over the 10 years we've worked together, have tried it all. And when I say we have tried it all, truly, we have tried it all. Asana, Monday, ClickUp, Notion, Trello, Basecamp, Co-schedule. I'm sure I'm forgetting some. When he and I first started working together 10 years ago, we had active projects in, I think, three or four totally separate task and or project management services. Like I distinctly remember Asana and Basecamp. And I want to say there might have even been some task and or project management happening inside of Box. Does anybody use or remember Box? It was like a Google Docs or Dropbox competitor. It was meant to be document storage, but I feel like it had, potentially, still has some project management and or task management capabilities. Absolutely broke my brain to have projects for the same company inside of three or four fully separate systems. You know, it is what it is. It was what it was. It is not the same today. But yes, my executive and I truly we tried it all. And honestly, I did not love any of them. It was always something where, you know, I loved the list and checkbox feature of Trello. And it has been years since I've used Trello. So don't quote me on this. It could be totally different today. You know, it had great list and like checkbox capabilities, which I really love. I love checking stuff off, striking stuff through that kind of thing. But it didn't, at the time, have the ability to like assign things dates. And sometimes that was really important depending on the project. You know, so what I'm getting at is you might log into one software and let's just say Asana had a really great capability to assign stuff dates, but their checklists and checkboxes weren't as great. And then Trello had really great checklists and checkboxes, but not the ability to assign things by date. So like each platform had its pros and cons. And again, this was 10 years ago. The last time I used Trello was probably four or five years ago. And I'm sure the platform has changed a lot within the last 10, even the last five, maybe even the last one year, who knows? But yeah, he and I have tried it all. And I spent a lot of time learning, setting up projects on various platforms. And every time that we had a check-in, every time we had a one-on-one, it was me going into the platform and saying, okay, inside of Trello, here are your tasks. Have you done any of these? I'm happy to be the one logging in, like whatever it is that I can bring to the table that streamlines systems and processes for my executive, that keeps him on task, that keeps him getting things done, I am more than happy to do. But it just turned out, he admitted several times, anytime we would implement a new system, he'd be like, Trello, right, haven't logged in to that in months. And so it just, it wasn't worth fitting myself into a platform that I didn't like or didn't understand or wasn't getting the full capabilities out of it, and paying for the privilege to do so. Like, I'm sure there were so many features and bells and whistles inside of any and or all of these platforms that I just was not like a master user of. And so, you know, just kind of ended up trying to recreate some pretty basic systems and processes inside of systems that were more robust and complex than either of us needed them to be. And so it just didn't make sense to keep them going, you know, like these platforms, no matter what you choose, are always going to be a big time investment up front. You or someone at your organization have to research, take demos from salespeople, schedule a demo with a salesperson. Like, oh my gosh, when you're scheduling across busy calendars, time zones, I don't have to tell you, you know, you have to get team input, you have to get budget approval. Maybe you have to have like a board of directors or the upper management team approve it. Like, these vetting processes can take weeks, if not months. And, you know, once all that's done, once you've already invested a ton of time, effort, research, money, because people's time is can be equated to money in actual budgetary dollars, you spend a ton of time getting to know the software, inputting the tasks, assigning the tasks. If you're going to, if it's just you and your executive, you know, is it you doing it? Is your executive doing it? If it's a bigger team, you know, how many people are on the team and who actually does what and needs all of the tasks assigned to them? You have to manage dates for the tasks. You have to follow up on the tasks, make sure they get done. You know, this is why there are people that their entire job is to be a project manager, you know, they do a lot of the meetings to determine schedules and workload divvying up and management of the project, project management software and tools. Like, it's a big job to do all that stuff. And a lot of times, if you work in a smaller team, a lot of that data entry and project management can fall to you as the executive assistant, especially again, in my situation where it's just me and my executive. All of that definitely fell 100% to me. It was up to me to choose the platform. It was up to me to implement it, to buy the licenses, to be the person doing all the data entry. Like, it was a lot. And my executive and I were a small organization of two. We don't need a corporate structure that suits hundreds, if not thousands of people. And again, when you have a structure that supports hundreds, if not thousands of people, you have people taking the demos, implementing the new software, doing the entry, and then if you're lucky, you just have to be the person logging in and checking your tasks off to keep it going. You know, so like all that said, I have found one project management software that I liked, one task management software that I liked, and I will talk about it in just a couple of minutes here. I will be the first person to admit that others who are not my executive, thankfully, but others that I work with have been a little frustrated with me because I honestly kind of refuse to use them. And it's not necessarily for secrecy, although there is a lot of confidential work involved in being an executive assistant. It's a lot of confidential company level information. It's a lot of confidential personal and or professional information about your executive and the work that they do. So there is an element of that, but it's also because by the time I remember which platform it is that I need to be logging into to do this stuff, because I have worked historically in organizations that change their platform every three, four, six, eight, 12 months. I work in organizations that have multiple project management softwares running concurrently. By the time I log in, log my tasks, check them off, I could have just done my work. I know what I need to do. An example that comes to mind is I know what I need to do to place a catering order. I need to review the menu, I need to make selections based on dietary needs and headcount, maybe call and discuss some of the finer details with the catering manager, and then place my order using their catering system. A lot of people have not been super happy with me in putting, quote, place catering order, end quote. They want the granular view, they want review menu, place order based on headcount, review dietary. By the time that I log in and do all that, I could have just done it. I really struggle with what feels like a combination of micromanage behavior combined with doing the job twice. Logging into a project management software to say that I called the caterer just feels like doing it twice. It feels redundant. My executive has never cared if I use a task management software. He only cares if the food shows up at the event, when and how it's supposed to. He wants hot or cold, depending on the menu. He wants fresh, he wants beautiful presentation, he wants delicious. He wants people's dietary restrictions being respected and observed. He doesn't care if I logged in to Asana and said that I called the catering manager and placed the catering order. He just wants to know that it's done. When we show up to the event or we talk about the event a week before it's going to happen and he says, hey, is there food? I'm like, yup, it's already been placed. It doesn't matter at the end of the day when you're in an organization of two. I don't honestly even know if it matters all that terribly much in a bigger organization. But on top of that, a lot of what I do as an executive assistant, and I'm sure this is true for a lot of you out there listening as well, a lot of my tasks are very much on the fly. They're in the moment, they're ad hoc. If my executive asks me to reach out to our accountant to ask about our corporate tax return, the chances of me logging in to a task management platform to add and subsequently check off the tasks that I just did, it's not going to happen. It's just not going to happen. I did touch on this a little bit earlier. I did use and love Evernote for a while when I worked at a company called Anaplan. It was a SaaS company, Software as a Service, S-A-A-S is that acronym. It had a lot of really great collaboration features for the time, but this was 10 years ago, 2014. The Internet has changed. Software and task management and project management platforms have changed a lot in the last 10 years. A lot of companies have also all of the other task management softwares that I mentioned, Asana, Basecamp, Trello, all of that. A lot of those companies have integrated features that used to make Evernote unique. Plus, I still cannot bring myself to use Evernote after this happened. I had a big Evernote fail. A project that I was working on, I was moving our office from a co-working space in New York City to one grand central place, I think, is the name of the building. It's a very beautiful historic building in either Manhattan or the financial district. I'd have to look at a map. I don't know my New York City quite as well as I used to 10 years ago. But I was working on the move with my facilities director, and just had inputted a bunch of stuff into our collaborative document, walked away from my computer for whatever reason it didn't save. Could have been an Internet blip, could have been some kind of issue with my computer. I could have closed my laptop before it fully saved. Like, who knows? This is 10 years ago. It thankfully wasn't the end of the world, but like it was so stressful. And from that day on, I just could not bring myself to trust it. And very faithfully from then on, wrote things out on paper, had a very important notebook that lived at my desk in a locked drawer that only I had a key to. I would input things to Evernote and then double-check that things had saved. It was so stressful and honestly, I still think about it like once a month to this day, and it's been 10 years. So yeah, just all the different softwares and platforms that I've tried. Again, working in an organization of two, one of the best things is that we can be and are flexible, we work with the tools that work for us. So all of that aside, all the things that I've tried and didn't love, my current system, the things that I presently use and absolutely do adore. I think I talked about this a bit on a podcast episode that I did with my executive way back in 2014. We had been working together for about three months. It was super nerve wracking for him to be like, hey, come be on my huge podcast. And I was like, oh my God, okay. It honestly hasn't changed all that much in 10 years. It's a mix of Slack, which is kind of the Google, shoot, not Google, the Microsoft Teams version. It's the equivalent of Microsoft Teams. My Google Workspace is what they're calling themselves these days, although it will always be Google Apps for Business in my heart. So Google Apps for Business, my inbox, my calendar, Google Sheets. I definitely use the Timer app on my phone quite a bit. I still use a paper notebook, Post-it notes and really nice pens. The only way my notebook fails is if I lose it.

Jeremy · 18:57

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Jess · 19:57

That's it if it gets lost or damaged, and my husband and I have three cats. They all have their own little quirks, the orange cat, and that is his name. The orange cat likes to chew on paper, so I do have to be very careful. Thankfully, I have a small office, my podcast closet where my notebook lives, and then if I ever do bring it out of my podcast closet, we have a platform bed that has storage drawers. And you better believe that the notebook lives with my laptop, they never leave each other, and they stay safe from my orange cat's teeth. But yeah, truly the notebook, the only way it can fail is if I lose it. When my executive sends me a task, I can often do it in the moment. If timing and or technology doesn't allow, I will set a reminder for myself in Slack, which is a feature that did not exist 10 plus years ago. I was a pretty early adopter to Slack. I used it for some consulting stuff as early as 2012 or 2013 maybe, and then started professionally using it full-time in 2014. This was not a feature back then. I could not tell you when this feature was instituted, and maybe it was a feature back then and I just didn't use it. Who knows? But I can set a reminder for myself in Slack. Like if he sends me a note, hey, check in with our accountant about our tax return, I can just say, hey, I'm on it. I can fire off an e-mail from anywhere in the world with my iPhone. If I'm really just not in a position, if it's something more complex than just, hey, accountant, give me an update on our tax return, something where I need to reference files or send attachments or type more than just a couple of sentences, I can press on the message and get a little, hey, remind myself in an hour, remind myself in two hours, set a custom reminder. Do I want to be reminded this afternoon or next week on Monday? So I really love that feature. I used to send myself an e-mail. I definitely do that a lot less now that Slack has the capability to remind me of a message. I will set a timer on my phone or put an appointment in my calendar to do it later. Yeah, honestly, I used to use my inbox a lot as a to-do list. And since Slack introduced the little ability to set a reminder, I very, very rarely send myself an e-mail these days. If something was to require a dedicated block of work time, I will work around whatever is best for my day or my week. I am so very privileged to work with somebody who doesn't care when I do my work. They just care that it gets done before it's due, if that makes sense. As long as things happen before it's a problem, like using the catering example, you can't place a catering order. I've talked about this before in the good, fast, cheap. You can pick two. Things can be good, they can be fast or they can be cheap. If I place my catering order weeks or months in advance, it's going to be good and it's going to be cheaper. If I place my catering order the day before my event, it hopefully will be good. And since it needs to be fast, it's not going to be cheap. Or if it needs to be fast and it needs to be cheap, it's not going to be good. You know, so just I'll link to that episode. I don't remember the episode number off the top of my head, but yeah, as long as things get done before they are due and before it is a problem, I am so very privileged to have an executive who just cares that things get done. He doesn't care how or when or why or how. And on top of that, I am also so very privileged to be not a very great morning person who lives in the Eastern time zone and works with someone in Pacific. So it just it works out really well for both of us that when he needs something at, you know, midnight my time, I'm still awake and I don't have to start my day until like 11 or noon Eastern, which I honestly just adore. But anyway, so when things need a dedicated work time, I work around whatever's best for my day and my week. I am very fortunate with all of the aforementioned flexibility in my schedule and trust from my executive to be able to pick up my niece from school on Wednesdays. Her school does basically like a half day, she's four, so she goes to a preschool and we have anti-adventure days on Wednesdays, and they're the best. I'm talking helium balloons at the dollar store, you should see the entry to my house. I'm talking self-checkout at Wegmans, we go kill an hour in the store looking at everything. She loves the beer displays at the back of the store. The beer companies all send their little mascots. There's a Santa Claus back there, there's half a horse for Sam Adams. There's a little Snoop Dogg figurine from Corona. We actually just recently met the guy who sets up the displays and he was very pleased to have a tiny little fan and my niece. I'm also talking French fries at the pizza place. There's a pizza place in our neighborhood that makes the best French fries. We call ahead and we order our French fries and we pick out a slice of pizza for my husband when we get to the pizza place. My niece and I do it up and it's only getting more fun the older she gets. But on top of that, I'm always available to my executive. I have very few apps that push through to my phone with notifications, Slack is one of them. So I'm always available to answer quick questions that he has or fire off a quick email. But things can almost always wait a couple hours until I take my niece home. For things that require a phone call, I usually try to choose an off hour for the business. Using the catering example, I am not going to call during peak meal hours or like on a Friday, which is a huge day for catering. I live in New York, I work California hours, time zones are always a factor. If I need to do something like with an airline, I have found that calling super late at night, so like 11, 1130, midnight Eastern is a great time to get right through to people. I have a notebook, it has a spiral binding that is large enough to accommodate a pen and has built-in dividers. Anytime I find notebooks like this, I always buy the store out. That notebook lives next to my laptop, but my notebook is a lot more project-based than task-based these days. I'm always working from a different room in the house or a different place around town. I might be in the dollar store parking lot. I might be at the self-checkout at the grocery store. Like I'm not bringing my notebook everywhere because again, the only way for it to fail is for it to be lost, and I cannot afford to lose that notebook. So it stays at home, and I can always go get it when I need it. For example, my executive has a new book coming out next year, and I have a dedicated section in one of my notebooks for the upcoming book tour that we're planning. We're running to live events next year. There's a section in my notebook for our live events. As for post-its, if there's something that absolutely must happen, the next time that I open my laptop, I will write it out on a post-it note. I open my laptop, I put it over the track pad so it can't be missed and it can't be lost if I put my laptop in a bag, and most importantly, it can't be eaten by my cat. That's my task management system. I think I've talked about all the things that I use. Slack, set reminders on messages that come through, a timer on my phone. I can set a reminder for when I get home, 20 minutes, an hour, four hours from now, whatever. You can set a little custom note that says do whatever the thing is. A paper notebook, I'm not using it as much these days, but it's always there if I need it. Like any good executive assistant, I have entirely too many Post-it notes and gorgeous pens. You need some, hit me up. Google Apps for Business, my Inbox, my Calendar, my Sheets. Inbox, I don't really email my things, email myself things as much as I used to since Slack allowed you to set a reminder on any specific messages. Calendar, I set times for myself to make calls, I set work blocks so that my husband knows what's up and when I need quiet, and I set things for when I know what works for my schedule and it works for the person that is involved on the other end. I definitely try to make myself very available to people, which is great being flexible like that. However, let's talk about Google Sheets, the Google equivalent to Excel. I have a very basic spreadsheet. It's literally two columns, it's who and what of the who, what, when, where, why of it all. Who and what, sometimes a when if I really need it. Who, I take things as they come in through my executive's inbox, take the email address so that I don't just say, oh, Jason from whatever, the email address will pull up exactly the person, exactly the message that I want. So that's the who, the what, what's the executive summary of the ask? If somebody sends you six paragraphs, can you read them, synthesize them, and condense them down into one to two sentences to tell your executive what the ask actually is? When, if there's a deadline that can usually be covered in the what field, like you can include that in your executive summary. That doesn't necessarily need, like right now, one of our coaching students asked for a, like a blurb for their book and, you know, hey, what's the title of the book? What's the tone of the blurb that you're looking for and what's your deadline? Like that can all fit inside of one to three sentences in an executive summary. If you really want the when field, go for it. And spreadsheets, you can make spreadsheets as complicated, as cute, as whatever is you want them to be, but truly, mine is just who and what, who's asking and what do they want. And that really covers it for me. It's not sophisticated, but it is built on technology that has literally never failed me. And it works. It works for me. We just had some change up in our team, and we had a meeting with the new team to discuss the process that we presently have. And I was really concerned that they were going to be like, oh my god, this is so outdated. This is so clunky. We need to get you into XYZ system. And we just explained the spreadsheet that we use. And everybody was on board. They were just like, hey, if it's not broke, don't fix it. Like this is working. We haven't had a problem in 10 years if you two using this spreadsheet, this system, this process, let's not overcomplicate it. And I was so relieved and so grateful. And there's just with all these platforms that are out there, like we already use and pay for Google Apps for business. Why have more services that do the same thing? Like you can replicate so many things in Google Sheets and Google Docs. Both are super collaborative. I don't know if anybody listening remembers, I think it was called like Google Wave, question mark, or like Google Plus, their little social networky thing. But like thankfully, Google has really streamlined a lot of their offerings over the years, has gotten rid of the things that were superfluous, that were redundant, and really focused on their core suite of offerings. And honestly, there's so much you can do again inside of Google Docs, Google Sheets. Why reinvent the wheel? Don't stress yourselves out. Obviously, a pared down system like this, a very cobbled together system like this of Google Sheets and Notebooks and Post-its, and a little bit of Slack, a little bit of a timer on the phone, it's not going to work for everybody. So I'd really love to hear from you. To everybody out there listening, let me know. I will be posting a poll on my LinkedIn in conjunction with this episode. What task management software, systems rather, because not everything's a software. I just spent 15 minutes talking about how much I love notebooks and pens and things that really aren't task management software. So what's your system? How do you get things done? How do you keep track of things? What do you use and what do you love about them? I would love to be swayed on any number of systems. If there's something that I'm just missing about Monday or Notion or Trello or what have you, like I would really, really love to be convinced otherwise, because I'm sure that my system made some people itchy listening to it. Like I'm sure people were like, oh my God, how does she not forget things? How do things not fall through the cracks? How does she not have a little button that she can click off to say that she did the task? Like honestly, for me, crumpling up and throwing away a post-it note feels way better than clicking off a task in whatever given project and task management software. But again, I'd love to be convinced otherwise. Let me know. Lay your comments, questions, thoughts and concerns on me. askanassistant.com. And until next week, take care. You're listening to The Leader Assistant Podcast.

Speaker 3 · 35:25

Please review on Apple Podcasts. Go bullos.com.

Jeremy · 35:40

Hey friends, my best selling 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.