Jess Lindgren is a longtime C-Suite assistant, and host of the Ask an Assistant podcast. You can learn more about Jess by listening to my conversations with her on episodes 23 and 313 of The Leader Assistant Podcast.
I’m excited to re-post several episodes of Jess’ podcast on this show over the coming months and I think you’ll enjoy hearing her point of view on all sorts of topics relevant to the assistant profession.
In this Ask an Assistant spotlight episode, Jess answers a question about task management systems.
CONNECT WITH JESS
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
–––
THE LEADER ASSISTANT PREMIUM MEMBERSHIP
To learn more about how you can join growth-minded Leader Assistants, check out our Leader Assistant Premium Membership for ongoing training, coaching, and community.
THE LEADER ASSISTANT BOOK
Download the first 3 chapters of The Leader Assistant: Four Pillars of Game-Changing Assistant for FREE here or buy it on Amazon and listen to the audiobook on Audible. Also, check out the companion study guide, The Leader Assistant Workbook, to dig deeper.
LEADER ASSISTANT LIVE EVENTS
Check out our constantly updated schedule of events for admins and assistants at LeaderAssistantLive.com.
JOIN THE FREE COMMUNITY
Join the Leader Assistant Global Community for bonus content, job opportunities, and to network with other assistants who are committed to becoming leaders!
SUBSCRIBE
Subscribe to The Leader Assistant Podcast so you don’t miss new episodes!
You can find the show on Apple Podcasts, Spotify, Google Podcasts, Pandora, and Stitcher.
Join my email list here if you want to get an email when a new episode goes live.
LEAVE A REVIEW
If you’re enjoying the podcast, please take 2 minutes to rate and review the show on Apple Podcasts here. Each review helps me stay motivated to keep the show going!
–––
EPISODE TRANSCRIPT
00:00:00.500 –> 00:00:03.220
JEREMY: Person-Meeting Planning can be a lot to manage.
00:00:03.220 –> 00:00:05.940
JEREMY: That’s where Troop Planner comes in.
00:00:05.940 –> 00:00:10.560
JEREMY: Troop Planner is built to make life easier for busy assistants like you.
00:00:10.560 –> 00:00:19.640
JEREMY: Whether you’re organizing an executive offsite, department meeting or team retreat, Troop keeps it simple, fast and organized.
00:00:19.640 –> 00:00:34.480
JEREMY: 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.
00:00:34.480 –> 00:00:41.140
JEREMY: Troop has an exclusive offer for leader assistant listeners through Administrative Professionals Day, so don’t miss out.
00:00:41.140 –> 00:00:45.180
JEREMY: Visit leaderassistant.com/troop to learn more.
00:00:46.240 –> 00:00:49.200
JEREMY: Hey friends, it’s Jeremy Burrows, host of The Leader Assistant Podcast.
00:00:49.200 –> 00:00:50.680
JEREMY: Thanks for tuning in.
00:00:50.680 –> 00:00:58.560
JEREMY: Today, I’m actually excited to put the spotlight on my friend Jess Lindgren’s podcast, called Ask an Assistant.
00:00:58.560 –> 00:01:15.800
JEREMY: I had the honor of interviewing Jess in episode 23 and episode 313 of this show, so be sure to check out those episodes, leaderassistant.com/23 and leaderassistant.com/313 to learn more about Jess and her career.
00:01:15.800 –> 00:01:23.880
JEREMY: As for the Ask an Assistant Podcast, Jess takes questions from you all and then answers them on the podcast.
00:01:24.120 –> 00:01:29.900
JEREMY: So, I’m going to actually share an episode of the Ask an Assistant Podcast with you today.
00:01:29.900 –> 00:01:38.360
JEREMY: Be sure to go to askanassistant.com to listen to other episodes or again, submit your question for Jess to answer on a future episode.
00:01:38.360 –> 00:01:38.980
JEREMY: Hope you enjoy it.
00:01:45.342 –> 00:01:52.882
<v SPEAKER_3>The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.
00:02:01.130 –> 00:02:08.290
JEREMY: Hey friends, my best-selling book, The Leader Assistant, has a companion study and discussion guide to go along with it.
00:02:08.290 –> 00:02:10.990
JEREMY: It’s called The Leader Assistant Workbook.
00:02:10.990 –> 00:02:24.570
JEREMY: 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.
00:02:24.570 –> 00:02:33.210
JEREMY: This version has all the space and margin in between the questions that you can write your own answers and take notes with.
00:02:33.210 –> 00:02:40.510
JEREMY: So it’s a great way to print it out and keep track of your discussion and study guide notes.
00:02:40.510 –> 00:02:46.670
JEREMY: Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.
00:02:52.058 –> 00:03:02.038
JESS: Hello, and welcome to another episode of Ask an Assistant, the podcast for executive assistants and the people that love us.
00:03:02.038 –> 00:03:03.758
JESS: I’m your host, Jess Lindgren.
00:03:03.758 –> 00:03:05.558
JESS: Let’s get to work.
00:03:05.558 –> 00:03:11.058
JESS: Today’s question comes from esteemed colleague, Debbie, who wrote in via askanassistant.com.
00:03:12.578 –> 00:03:17.558
JESS: She says, hi Jess, do you have a recommendation for task management software?
00:03:17.558 –> 00:03:24.298
JESS: My executive has a dozen different projects going at any given time and it’s becoming unwieldy to manage them all.
00:03:24.298 –> 00:03:26.618
JESS: I’m afraid things will slip through the cracks.
00:03:26.618 –> 00:03:32.158
JESS: What have you used and loved and on the flip side of the coin, what have you used and not loved?
00:03:32.158 –> 00:03:35.258
JESS: Debbie, I know I say this all the time.
00:03:35.258 –> 00:03:43.738
JESS: 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.
00:03:43.738 –> 00:03:45.838
JESS: I would love to hear from you.
00:03:45.838 –> 00:03:49.258
JESS: And again, I know I say this all the time, but I really do love this question.
00:03:49.918 –> 00:03:56.618
JESS: I also work with somebody who has a dozen different projects going at any given time.
00:03:56.618 –> 00:04:01.678
JESS: My executive is an author, blogger, podcaster, YouTuber.
00:04:01.678 –> 00:04:07.738
JESS: He has three active and very well-subscribed YouTube channels at the time of recording.
00:04:07.738 –> 00:04:13.318
JESS: We run live events, we produce a podcast, like just so much going on.
00:04:15.138 –> 00:04:20.238
JESS: And he and I, over the 10 years we’ve worked together, have tried it all.
00:04:20.238 –> 00:04:24.298
JESS: And when I say we have tried it all, truly, we have tried it all.
00:04:24.298 –> 00:04:30.398
JESS: Asana, Monday, ClickUp, Notion, Trello, Basecamp, Co-schedule.
00:04:30.398 –> 00:04:32.838
JESS: I’m sure I’m forgetting some.
00:04:33.058 –> 00:04:47.318
JESS: 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.
00:04:47.318 –> 00:04:51.798
JESS: Like I distinctly remember Asana and Basecamp.
00:04:51.798 –> 00:04:59.458
JESS: And I want to say there might have even been some task and or project management happening inside of Box.
00:04:59.458 –> 00:05:01.378
JESS: Does anybody use or remember Box?
00:05:01.378 –> 00:05:06.978
JESS: It was like a Google Docs or Dropbox competitor.
00:05:06.978 –> 00:05:16.118
JESS: It was meant to be document storage, but I feel like it had, potentially, still has some project management and or task management capabilities.
00:05:17.298 –> 00:05:28.618
JESS: Absolutely broke my brain to have projects for the same company inside of three or four fully separate systems.
00:05:30.718 –> 00:05:31.978
JESS: You know, it is what it is.
00:05:31.978 –> 00:05:34.018
JESS: It was what it was.
00:05:34.018 –> 00:05:35.558
JESS: It is not the same today.
00:05:36.778 –> 00:05:39.598
JESS: But yes, my executive and I truly we tried it all.
00:05:39.598 –> 00:05:44.078
JESS: And honestly, I did not love any of them.
00:05:44.078 –> 00:05:50.238
JESS: It was always something where, you know, I loved the list and checkbox feature of Trello.
00:05:50.438 –> 00:05:52.338
JESS: And it has been years since I’ve used Trello.
00:05:52.338 –> 00:05:53.418
JESS: So don’t quote me on this.
00:05:53.418 –> 00:05:56.198
JESS: It could be totally different today.
00:05:56.198 –> 00:05:59.838
JESS: You know, it had great list and like checkbox capabilities, which I really love.
00:05:59.838 –> 00:06:03.498
JESS: I love checking stuff off, striking stuff through that kind of thing.
00:06:04.118 –> 00:06:11.478
JESS: But it didn’t, at the time, have the ability to like assign things dates.
00:06:11.478 –> 00:06:15.658
JESS: And sometimes that was really important depending on the project.
00:06:15.658 –> 00:06:27.378
JESS: 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.
00:06:27.378 –> 00:06:32.558
JESS: And then Trello had really great checklists and checkboxes, but not the ability to assign things by date.
00:06:32.938 –> 00:06:35.878
JESS: So like each platform had its pros and cons.
00:06:35.878 –> 00:06:37.918
JESS: And again, this was 10 years ago.
00:06:37.918 –> 00:06:41.698
JESS: The last time I used Trello was probably four or five years ago.
00:06:41.698 –> 00:06:49.798
JESS: 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?
00:06:50.998 –> 00:06:53.758
JESS: But yeah, he and I have tried it all.
00:06:53.758 –> 00:07:00.598
JESS: And I spent a lot of time learning, setting up projects on various platforms.
00:07:01.218 –> 00:07:10.878
JESS: 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.
00:07:10.878 –> 00:07:12.698
JESS: Have you done any of these?
00:07:14.298 –> 00:07:28.658
JESS: 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.
00:07:29.958 –> 00:07:41.338
JESS: 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.
00:07:41.338 –> 00:07:56.378
JESS: 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.
00:07:57.458 –> 00:08:08.998
JESS: 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.
00:08:08.998 –> 00:08:22.618
JESS: 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.
00:08:22.618 –> 00:08:32.458
JESS: 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.
00:08:32.458 –> 00:08:41.658
JESS: You or someone at your organization have to research, take demos from salespeople, schedule a demo with a salesperson.
00:08:41.658 –> 00:08:51.798
JESS: 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.
00:08:51.798 –> 00:08:58.058
JESS: Maybe you have to have like a board of directors or the upper management team approve it.
00:08:58.058 –> 00:09:04.418
JESS: Like, these vetting processes can take weeks, if not months.
00:09:04.418 –> 00:09:25.478
JESS: 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.
00:09:25.478 –> 00:09:30.218
JESS: If you’re going to, if it’s just you and your executive, you know, is it you doing it?
00:09:30.218 –> 00:09:33.358
JESS: Is your executive doing it?
00:09:33.358 –> 00:09:42.138
JESS: 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?
00:09:42.138 –> 00:09:44.278
JESS: You have to manage dates for the tasks.
00:09:44.278 –> 00:09:47.138
JESS: You have to follow up on the tasks, make sure they get done.
00:09:47.138 –> 00:10:04.358
JESS: 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.
00:10:04.358 –> 00:10:07.418
JESS: Like, it’s a big job to do all that stuff.
00:10:07.418 –> 00:10:20.958
JESS: 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.
00:10:21.418 –> 00:10:24.858
JESS: All of that definitely fell 100% to me.
00:10:24.858 –> 00:10:27.718
JESS: It was up to me to choose the platform.
00:10:27.718 –> 00:10:33.618
JESS: It was up to me to implement it, to buy the licenses, to be the person doing all the data entry.
00:10:33.618 –> 00:10:36.198
JESS: Like, it was a lot.
00:10:36.198 –> 00:10:42.198
JESS: And my executive and I were a small organization of two.
00:10:42.198 –> 00:10:47.178
JESS: We don’t need a corporate structure that suits hundreds, if not thousands of people.
00:10:48.618 –> 00:11:05.338
JESS: 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.
00:11:06.818 –> 00:11:18.458
JESS: 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.
00:11:18.458 –> 00:11:33.778
JESS: 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.
00:11:33.778 –> 00:11:41.658
JESS: And it’s not necessarily for secrecy, although there is a lot of confidential work involved in being an executive assistant.
00:11:41.658 –> 00:11:45.038
JESS: It’s a lot of confidential company level information.
00:11:45.118 –> 00:11:52.438
JESS: It’s a lot of confidential personal and or professional information about your executive and the work that they do.
00:11:52.438 –> 00:12:15.578
JESS: 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.
00:12:17.598 –> 00:12:24.298
JESS: I work in organizations that have multiple project management softwares running concurrently.
00:12:24.298 –> 00:12:31.738
JESS: By the time I log in, log my tasks, check them off, I could have just done my work.
00:12:31.738 –> 00:12:32.818
JESS: I know what I need to do.
00:12:33.038 –> 00:12:37.598
JESS: An example that comes to mind is I know what I need to do to place a catering order.
00:12:37.598 –> 00:12:53.678
JESS: 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.
00:12:53.678 –> 00:13:02.698
JESS: A lot of people have not been super happy with me in putting, quote, place catering order, end quote.
00:13:02.698 –> 00:13:10.078
JESS: They want the granular view, they want review menu, place order based on headcount, review dietary.
00:13:10.078 –> 00:13:15.438
JESS: By the time that I log in and do all that, I could have just done it.
00:13:15.438 –> 00:13:24.078
JESS: I really struggle with what feels like a combination of micromanage behavior combined with doing the job twice.
00:13:26.198 –> 00:13:35.778
JESS: Logging into a project management software to say that I called the caterer just feels like doing it twice.
00:13:35.778 –> 00:13:37.618
JESS: It feels redundant.
00:13:37.618 –> 00:13:42.298
JESS: My executive has never cared if I use a task management software.
00:13:42.298 –> 00:13:47.178
JESS: He only cares if the food shows up at the event, when and how it’s supposed to.
00:13:47.178 –> 00:13:51.238
JESS: He wants hot or cold, depending on the menu.
00:13:51.238 –> 00:13:54.418
JESS: He wants fresh, he wants beautiful presentation, he wants delicious.
00:13:54.418 –> 00:14:00.218
JESS: He wants people’s dietary restrictions being respected and observed.
00:14:00.218 –> 00:14:07.518
JESS: He doesn’t care if I logged in to Asana and said that I called the catering manager and placed the catering order.
00:14:07.518 –> 00:14:09.158
JESS: He just wants to know that it’s done.
00:14:09.158 –> 00:14:14.958
JESS: 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?
00:14:14.958 –> 00:14:16.998
JESS: I’m like, yup, it’s already been placed.
00:14:16.998 –> 00:14:20.638
JESS: It doesn’t matter at the end of the day when you’re in an organization of two.
00:14:21.398 –> 00:14:26.238
JESS: I don’t honestly even know if it matters all that terribly much in a bigger organization.
00:14:28.598 –> 00:14:39.778
JESS: 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.
00:14:39.778 –> 00:14:43.018
JESS: They’re in the moment, they’re ad hoc.
00:14:43.018 –> 00:15:00.538
JESS: 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.
00:15:00.538 –> 00:15:02.158
JESS: It’s just not going to happen.
00:15:03.698 –> 00:15:05.718
JESS: I did touch on this a little bit earlier.
00:15:05.718 –> 00:15:10.818
JESS: I did use and love Evernote for a while when I worked at a company called Anaplan.
00:15:10.858 –> 00:15:17.438
JESS: It was a SaaS company, Software as a Service, S-A-A-S is that acronym.
00:15:17.438 –> 00:15:23.958
JESS: It had a lot of really great collaboration features for the time, but this was 10 years ago, 2014.
00:15:23.958 –> 00:15:25.638
JESS: The Internet has changed.
00:15:26.938 –> 00:15:33.098
JESS: Software and task management and project management platforms have changed a lot in the last 10 years.
00:15:34.658 –> 00:15:42.778
JESS: A lot of companies have also all of the other task management softwares that I mentioned, Asana, Basecamp, Trello, all of that.
00:15:42.778 –> 00:15:50.078
JESS: A lot of those companies have integrated features that used to make Evernote unique.
00:15:50.078 –> 00:15:56.658
JESS: Plus, I still cannot bring myself to use Evernote after this happened.
00:15:56.658 –> 00:15:59.238
JESS: I had a big Evernote fail.
00:15:59.238 –> 00:16:10.178
JESS: 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.
00:16:10.178 –> 00:16:15.738
JESS: It’s a very beautiful historic building in either Manhattan or the financial district.
00:16:15.738 –> 00:16:16.678
JESS: I’d have to look at a map.
00:16:16.678 –> 00:16:20.798
JESS: I don’t know my New York City quite as well as I used to 10 years ago.
00:16:20.798 –> 00:16:34.718
JESS: 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.
00:16:36.878 –> 00:16:40.718
JESS: Could have been an Internet blip, could have been some kind of issue with my computer.
00:16:40.718 –> 00:16:45.498
JESS: I could have closed my laptop before it fully saved.
00:16:45.498 –> 00:16:46.698
JESS: Like, who knows?
00:16:46.698 –> 00:16:47.778
JESS: This is 10 years ago.
00:16:47.778 –> 00:16:51.878
JESS: It thankfully wasn’t the end of the world, but like it was so stressful.
00:16:53.018 –> 00:16:56.778
JESS: And from that day on, I just could not bring myself to trust it.
00:16:56.778 –> 00:17:07.558
JESS: 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.
00:17:07.558 –> 00:17:11.338
JESS: I would input things to Evernote and then double-check that things had saved.
00:17:11.338 –> 00:17:18.898
JESS: It was so stressful and honestly, I still think about it like once a month to this day, and it’s been 10 years.
00:17:20.458 –> 00:17:25.918
JESS: So yeah, just all the different softwares and platforms that I’ve tried.
00:17:25.918 –> 00:17:38.978
JESS: 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.
00:17:38.978 –> 00:17:51.578
JESS: 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.
00:17:51.578 –> 00:17:58.158
JESS: I think I talked about this a bit on a podcast episode that I did with my executive way back in 2014.
00:17:59.378 –> 00:18:02.638
JESS: We had been working together for about three months.
00:18:02.638 –> 00:18:06.338
JESS: It was super nerve wracking for him to be like, hey, come be on my huge podcast.
00:18:06.338 –> 00:18:08.278
JESS: And I was like, oh my God, okay.
00:18:09.698 –> 00:18:12.838
JESS: It honestly hasn’t changed all that much in 10 years.
00:18:12.838 –> 00:18:22.778
JESS: It’s a mix of Slack, which is kind of the Google, shoot, not Google, the Microsoft Teams version.
00:18:22.778 –> 00:18:24.258
JESS: It’s the equivalent of Microsoft Teams.
00:18:25.618 –> 00:18:33.358
JESS: My Google Workspace is what they’re calling themselves these days, although it will always be Google Apps for Business in my heart.
00:18:33.358 –> 00:18:38.778
JESS: So Google Apps for Business, my inbox, my calendar, Google Sheets.
00:18:38.778 –> 00:18:43.478
JESS: I definitely use the Timer app on my phone quite a bit.
00:18:43.478 –> 00:18:49.038
JESS: I still use a paper notebook, Post-it notes and really nice pens.
00:18:49.038 –> 00:18:51.798
JESS: The only way my notebook fails is if I lose it.
00:18:57.387 –> 00:19:06.347
JEREMY: The ping pong back and forth game of manually scheduling meetings is unnecessary and inefficient in today’s automated world.
00:19:06.347 –> 00:19:12.567
JEREMY: It’s time to embrace calendar automation for increased productivity and capacity.
00:19:12.567 –> 00:19:17.847
JEREMY: You Can Book Me by Capacity is my favorite automated booking solution.
00:19:17.847 –> 00:19:21.267
JEREMY: It’s a game changer for me and my executive.
00:19:21.267 –> 00:19:30.727
JEREMY: You can manage scheduling for your entire executive team, send automated reminders, add buffer time between appointments, and much more.
00:19:30.727 –> 00:19:39.647
JEREMY: You Can Book Me integrates with your existing Microsoft and Google calendars, so you can add automation without disrupting your current workflow.
00:19:39.647 –> 00:19:48.947
JEREMY: Go to leaderassistant.com/calendar to learn more and sign up for a free trial of this powerful scheduling automation tool.
00:19:48.947 –> 00:19:50.327
JEREMY: That’s leaderassistant.com/calendar.
00:19:57.547 –> 00:20:03.887
JESS: That’s it if it gets lost or damaged, and my husband and I have three cats.
00:20:03.887 –> 00:20:08.407
JESS: They all have their own little quirks, the orange cat, and that is his name.
00:20:08.407 –> 00:20:12.447
JESS: The orange cat likes to chew on paper, so I do have to be very careful.
00:20:12.447 –> 00:20:26.287
JESS: 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.
00:20:26.287 –> 00:20:36.727
JESS: 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.
00:20:38.107 –> 00:20:43.287
JESS: But yeah, truly the notebook, the only way it can fail is if I lose it.
00:20:44.367 –> 00:20:49.347
JESS: When my executive sends me a task, I can often do it in the moment.
00:20:49.347 –> 00:20:59.307
JESS: 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.
00:20:59.307 –> 00:21:02.447
JESS: I was a pretty early adopter to Slack.
00:21:02.447 –> 00:21:12.367
JESS: I used it for some consulting stuff as early as 2012 or 2013 maybe, and then started professionally using it full-time in 2014.
00:21:14.167 –> 00:21:15.647
JESS: This was not a feature back then.
00:21:15.887 –> 00:21:20.767
JESS: 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.
00:21:20.767 –> 00:21:22.587
JESS: Who knows?
00:21:22.587 –> 00:21:26.027
JESS: But I can set a reminder for myself in Slack.
00:21:26.027 –> 00:21:33.367
JESS: 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.
00:21:33.367 –> 00:21:40.447
JESS: I can fire off an e-mail from anywhere in the world with my iPhone.
00:21:40.447 –> 00:22:03.287
JESS: 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.
00:22:03.287 –> 00:22:07.967
JESS: Do I want to be reminded this afternoon or next week on Monday?
00:22:07.967 –> 00:22:09.807
JESS: So I really love that feature.
00:22:12.287 –> 00:22:15.227
JESS: I used to send myself an e-mail.
00:22:15.227 –> 00:22:23.367
JESS: I definitely do that a lot less now that Slack has the capability to remind me of a message.
00:22:24.607 –> 00:22:30.807
JESS: I will set a timer on my phone or put an appointment in my calendar to do it later.
00:22:32.747 –> 00:22:38.507
JESS: Yeah, honestly, I used to use my inbox a lot as a to-do list.
00:22:39.227 –> 00:22:48.987
JESS: And since Slack introduced the little ability to set a reminder, I very, very rarely send myself an e-mail these days.
00:22:50.327 –> 00:22:58.927
JESS: If something was to require a dedicated block of work time, I will work around whatever is best for my day or my week.
00:22:58.927 –> 00:23:04.847
JESS: I am so very privileged to work with somebody who doesn’t care when I do my work.
00:23:04.967 –> 00:23:09.947
JESS: They just care that it gets done before it’s due, if that makes sense.
00:23:09.947 –> 00:23:18.227
JESS: As long as things happen before it’s a problem, like using the catering example, you can’t place a catering order.
00:23:18.227 –> 00:23:21.507
JESS: I’ve talked about this before in the good, fast, cheap.
00:23:21.507 –> 00:23:22.607
JESS: You can pick two.
00:23:22.607 –> 00:23:25.167
JESS: Things can be good, they can be fast or they can be cheap.
00:23:25.167 –> 00:23:30.987
JESS: If I place my catering order weeks or months in advance, it’s going to be good and it’s going to be cheaper.
00:23:31.587 –> 00:23:37.667
JESS: If I place my catering order the day before my event, it hopefully will be good.
00:23:38.707 –> 00:23:42.587
JESS: And since it needs to be fast, it’s not going to be cheap.
00:23:42.587 –> 00:23:50.827
JESS: Or if it needs to be fast and it needs to be cheap, it’s not going to be good.
00:23:50.827 –> 00:23:53.007
JESS: You know, so just I’ll link to that episode.
00:23:53.007 –> 00:24:05.887
JESS: 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.
00:24:05.887 –> 00:24:10.867
JESS: He doesn’t care how or when or why or how.
00:24:12.167 –> 00:24:23.267
JESS: 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.
00:24:23.267 –> 00:24:41.267
JESS: 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.
00:24:41.267 –> 00:24:48.427
JESS: But anyway, so when things need a dedicated work time, I work around whatever’s best for my day and my week.
00:24:48.427 –> 00:24:59.727
JESS: 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.
00:24:59.727 –> 00:25:10.247
JESS: 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.
00:25:10.247 –> 00:25:17.447
JESS: I’m talking helium balloons at the dollar store, you should see the entry to my house.
00:25:17.447 –> 00:25:23.227
JESS: I’m talking self-checkout at Wegmans, we go kill an hour in the store looking at everything.
00:25:23.387 –> 00:25:27.007
JESS: She loves the beer displays at the back of the store.
00:25:27.967 –> 00:25:31.907
JESS: The beer companies all send their little mascots.
00:25:31.907 –> 00:25:36.127
JESS: There’s a Santa Claus back there, there’s half a horse for Sam Adams.
00:25:36.127 –> 00:25:41.507
JESS: There’s a little Snoop Dogg figurine from Corona.
00:25:41.507 –> 00:25:48.827
JESS: 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.
00:25:48.827 –> 00:25:51.127
JESS: I’m also talking French fries at the pizza place.
00:25:51.367 –> 00:25:55.467
JESS: There’s a pizza place in our neighborhood that makes the best French fries.
00:25:55.467 –> 00:26:02.887
JESS: 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.
00:26:02.887 –> 00:26:08.587
JESS: My niece and I do it up and it’s only getting more fun the older she gets.
00:26:08.587 –> 00:26:12.367
JESS: But on top of that, I’m always available to my executive.
00:26:13.847 –> 00:26:18.927
JESS: I have very few apps that push through to my phone with notifications, Slack is one of them.
00:26:19.887 –> 00:26:25.527
JESS: So I’m always available to answer quick questions that he has or fire off a quick email.
00:26:25.527 –> 00:26:31.407
JESS: But things can almost always wait a couple hours until I take my niece home.
00:26:31.407 –> 00:26:37.827
JESS: For things that require a phone call, I usually try to choose an off hour for the business.
00:26:37.827 –> 00:26:45.927
JESS: 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.
00:26:45.967 –> 00:26:50.667
JESS: I live in New York, I work California hours, time zones are always a factor.
00:26:50.667 –> 00:27:01.887
JESS: 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.
00:27:04.147 –> 00:27:12.467
JESS: I have a notebook, it has a spiral binding that is large enough to accommodate a pen and has built-in dividers.
00:27:12.467 –> 00:27:16.107
JESS: Anytime I find notebooks like this, I always buy the store out.
00:27:16.107 –> 00:27:24.287
JESS: That notebook lives next to my laptop, but my notebook is a lot more project-based than task-based these days.
00:27:24.287 –> 00:27:29.587
JESS: I’m always working from a different room in the house or a different place around town.
00:27:29.587 –> 00:27:31.767
JESS: I might be in the dollar store parking lot.
00:27:31.767 –> 00:27:33.867
JESS: I might be at the self-checkout at the grocery store.
00:27:33.867 –> 00:27:42.527
JESS: 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.
00:27:43.467 –> 00:27:47.567
JESS: So it stays at home, and I can always go get it when I need it.
00:27:47.567 –> 00:27:56.747
JESS: 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.
00:27:56.747 –> 00:27:59.387
JESS: We’re running to live events next year.
00:27:59.387 –> 00:28:02.527
JESS: There’s a section in my notebook for our live events.
00:28:03.947 –> 00:28:12.987
JESS: 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.
00:28:12.987 –> 00:28:25.987
JESS: 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.
00:28:28.547 –> 00:28:31.627
JESS: That’s my task management system.
00:28:31.627 –> 00:28:35.167
JESS: I think I’ve talked about all the things that I use.
00:28:35.167 –> 00:28:41.667
JESS: Slack, set reminders on messages that come through, a timer on my phone.
00:28:41.667 –> 00:28:47.747
JESS: I can set a reminder for when I get home, 20 minutes, an hour, four hours from now, whatever.
00:28:47.747 –> 00:28:52.367
JESS: You can set a little custom note that says do whatever the thing is.
00:28:52.367 –> 00:28:58.007
JESS: A paper notebook, I’m not using it as much these days, but it’s always there if I need it.
00:28:59.047 –> 00:29:06.047
JESS: Like any good executive assistant, I have entirely too many Post-it notes and gorgeous pens.
00:29:06.047 –> 00:29:07.167
JESS: You need some, hit me up.
00:29:08.767 –> 00:29:13.127
JESS: Google Apps for Business, my Inbox, my Calendar, my Sheets.
00:29:13.127 –> 00:29:23.967
JESS: 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.
00:29:23.967 –> 00:29:41.807
JESS: 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.
00:29:41.807 –> 00:29:50.227
JESS: I definitely try to make myself very available to people, which is great being flexible like that.
00:29:51.727 –> 00:29:58.347
JESS: However, let’s talk about Google Sheets, the Google equivalent to Excel.
00:29:58.347 –> 00:30:00.847
JESS: I have a very basic spreadsheet.
00:30:00.847 –> 00:30:09.487
JESS: It’s literally two columns, it’s who and what of the who, what, when, where, why of it all.
00:30:09.487 –> 00:30:13.587
JESS: Who and what, sometimes a when if I really need it.
00:30:13.587 –> 00:30:29.547
JESS: 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.
00:30:29.547 –> 00:30:33.987
JESS: So that’s the who, the what, what’s the executive summary of the ask?
00:30:33.987 –> 00:30:44.627
JESS: 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?
00:30:45.647 –> 00:30:53.847
JESS: When, if there’s a deadline that can usually be covered in the what field, like you can include that in your executive summary.
00:30:53.847 –> 00:31:06.687
JESS: 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?
00:31:06.687 –> 00:31:09.987
JESS: What’s the tone of the blurb that you’re looking for and what’s your deadline?
00:31:09.987 –> 00:31:15.427
JESS: Like that can all fit inside of one to three sentences in an executive summary.
00:31:15.427 –> 00:31:18.507
JESS: If you really want the when field, go for it.
00:31:18.507 –> 00:31:31.047
JESS: 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.
00:31:31.047 –> 00:31:34.767
JESS: And that really covers it for me.
00:31:35.907 –> 00:31:41.867
JESS: It’s not sophisticated, but it is built on technology that has literally never failed me.
00:31:41.867 –> 00:31:42.907
JESS: And it works.
00:31:42.907 –> 00:31:45.047
JESS: It works for me.
00:31:45.047 –> 00:31:57.487
JESS: 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.
00:31:57.487 –> 00:32:01.747
JESS: And I was really concerned that they were going to be like, oh my god, this is so outdated.
00:32:01.747 –> 00:32:03.747
JESS: This is so clunky.
00:32:03.747 –> 00:32:06.107
JESS: We need to get you into XYZ system.
00:32:06.107 –> 00:32:10.747
JESS: And we just explained the spreadsheet that we use.
00:32:10.747 –> 00:32:12.907
JESS: And everybody was on board.
00:32:12.907 –> 00:32:15.307
JESS: They were just like, hey, if it’s not broke, don’t fix it.
00:32:15.307 –> 00:32:17.707
JESS: Like this is working.
00:32:17.707 –> 00:32:25.707
JESS: We haven’t had a problem in 10 years if you two using this spreadsheet, this system, this process, let’s not overcomplicate it.
00:32:25.707 –> 00:32:28.707
JESS: And I was so relieved and so grateful.
00:32:30.067 –> 00:32:37.927
JESS: And there’s just with all these platforms that are out there, like we already use and pay for Google Apps for business.
00:32:37.927 –> 00:32:41.267
JESS: Why have more services that do the same thing?
00:32:41.267 –> 00:32:45.927
JESS: Like you can replicate so many things in Google Sheets and Google Docs.
00:32:45.927 –> 00:32:47.467
JESS: Both are super collaborative.
00:32:47.467 –> 00:32:58.267
JESS: 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.
00:33:00.127 –> 00:33:10.627
JESS: 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.
00:33:10.627 –> 00:33:15.387
JESS: And honestly, there’s so much you can do again inside of Google Docs, Google Sheets.
00:33:16.567 –> 00:33:17.827
JESS: Why reinvent the wheel?
00:33:17.827 –> 00:33:20.287
JESS: Don’t stress yourselves out.
00:33:20.287 –> 00:33:36.847
JESS: 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.
00:33:36.847 –> 00:33:38.587
JESS: So I’d really love to hear from you.
00:33:38.587 –> 00:33:40.587
JESS: To everybody out there listening, let me know.
00:33:41.727 –> 00:33:46.767
JESS: I will be posting a poll on my LinkedIn in conjunction with this episode.
00:33:46.767 –> 00:33:52.627
JESS: What task management software, systems rather, because not everything’s a software.
00:33:53.747 –> 00:34:03.187
JESS: I just spent 15 minutes talking about how much I love notebooks and pens and things that really aren’t task management software.
00:34:03.187 –> 00:34:04.627
JESS: So what’s your system?
00:34:04.627 –> 00:34:05.547
JESS: How do you get things done?
00:34:05.547 –> 00:34:06.647
JESS: How do you keep track of things?
00:34:06.687 –> 00:34:09.247
JESS: What do you use and what do you love about them?
00:34:09.247 –> 00:34:13.287
JESS: I would love to be swayed on any number of systems.
00:34:13.287 –> 00:34:31.907
JESS: 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.
00:34:31.907 –> 00:34:35.027
JESS: Like I’m sure people were like, oh my God, how does she not forget things?
00:34:35.127 –> 00:34:37.287
JESS: How do things not fall through the cracks?
00:34:37.287 –> 00:34:41.667
JESS: How does she not have a little button that she can click off to say that she did the task?
00:34:41.667 –> 00:34:52.327
JESS: 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.
00:34:52.327 –> 00:34:55.567
JESS: But again, I’d love to be convinced otherwise.
00:34:55.567 –> 00:34:56.887
JESS: Let me know.
00:34:56.887 –> 00:34:59.167
JESS: Lay your comments, questions, thoughts and concerns on me.
00:34:59.167 –> 00:35:01.747
JESS: askanassistant.com.
00:35:01.747 –> 00:35:03.627
JESS: And until next week, take care.
00:35:12.930 –> 00:35:15.050
JESS: You’re listening to The Leader Assistant Podcast.
00:35:25.535 –> 00:35:27.915
<v SPEAKER_3>Please review on Apple Podcasts.
00:35:34.328 –> 00:35:36.028
<v SPEAKER_3>Go bullos.com.
00:35:40.068 –> 00:35:47.028
JEREMY: Hey friends, my best selling book, The Leader Assistant, has a companion study and discussion guide to go along with it.
00:35:47.028 –> 00:35:49.708
JEREMY: It’s called The Leader Assistant Workbook.
00:35:49.708 –> 00:36:02.728
JEREMY: 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.
00:36:03.328 –> 00:36:11.928
JEREMY: This version has all the space and margin in between the questions that you can write your own answers and take notes with.
00:36:11.928 –> 00:36:19.368
JEREMY: So it’s a great way to print it out and keep track of your discussion and study guide notes.
00:36:19.368 –> 00:36:25.528
JEREMY: Again, go to leaderassistantbook.com and click on Workbook to check out The Leader Assistant Workbook.
