Shelley Trask is the Senior Executive Assistant to Cal Henderson, CTO at Slack in San Francisco. The Slack team does not use email. I love email. Shelley loves Slack. I am not a big fan of how easy it is for people to get ahold of me via Slack. This should be fun…
Shelley talks about what she loves about the EA role, productivity tips, and why Slack doesn’t use email internally. She also shares some insider tips on getting the most out – and embracing Slack, and talks about what it’s like to work for a fast-growing company. Thank you, Shelley, for a great conversation!
LEADERSHIP QUOTE
No one can make you feel inferior without your consent.
– Eleanor Roosevelt
CONNECT WITH SHELLEY
ABOUT SHELLEY
Shelley Trask is currently the Senior Executive Assistant to Cal Henderson, CTO at Slack in San Francisco. In the last two years, she scaled the Engineering EA team from a party of one to a team of five, supporting over 700 people. She previously worked at startups in AI, Biotech and SaaS, as well as advertising and environmental planning. When she’s not diligently working, you can find her gardening, playing with her tiny dog, browsing garage sales, and alternating between the 20 tabs open in her browser to find the best version of whatever she’s currently obsessed with. She would like to tell you about the bright future for art majors with discipline and organization skills.
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EPISODE TRANSCRIPT
Shelley Trask 0:00
Hi, I’m Shelly Trask. Today’s leadership quote comes from Eleanor Roosevelt. No one can make you feel inferior without your consent.
Podcast Intro 0:10
The Leader Assistant Podcast exists to encourage and challenge assistants to become competent game changing leader assistants
Speaker 3 0:21
check out my dad’s book at leader, Assistant book.com Welcome to Episode 65.
Jeremy Burrows 0:31
Hey, leader assistance. We’re one week away from book launch. So I’m very excited to launch worldwide on June 23. I’m going to do the Kindle version on Amazon for only 99 cents. Be sure to check that out next week. I’ve got a live event with Monique Helstrom. On book launch day, June 23, you can register at leaderassistant book.com/events. To join us we’re going to have a little online launch party and do some giveaways and do a little bit of q&a and yeah, just have some fun doing a live webinar with Monique Helstrom. Monique is former chief executive assistant to Simon Sinek. She’s been on the show before. So you’ve probably heard her and she also wrote the foreword to the book. So very thankful for her doing that. And just very excited to have her join me on launch day on June 23 for a live book launch party event leaderassistantbook.com/events. And if you haven’t yet you can download the first three chapters for free while you’re waiting for the complete book to come out. Leader assistant book.com. All right, let’s jump into today’s interview. I hope you enjoy it. And thanks for all your support. And I’ll be in touch next week for a book launch. Hello, welcome to The Leader Assistant Podcast is your host to Jeremy Burrows. And today I’m speaking with Shelley Trask from slack. She’s the executive assistant to the CTO. How’s it going Shelly?
Shelley Trask 2:05
It’s going well. Thank you, Jeremy, for having me on your podcast.
Jeremy Burrows 2:08
Yeah. And you’re, you’re in California, right?
Shelley Trask 2:11
That’s correct. Nice and overcast today.
Jeremy Burrows 2:15
So at least the temperatures above freezing.
Unknown Speaker 2:17
This is true. Awesome.
Jeremy Burrows 2:20
Well, what was your very first job? And what skills did you learn in that role that you still use today?
Shelley Trask 2:27
This is a great question for me my first job. I was 17, which is a little old to start your first job, but I was busy making art. My mother marched me into a discount linen store called Stroud, which has since closed and she told the person at the desk then her daughter would very much like to apply for this role. To which I I said what? And I sort of wish my mom had marched me into an office instead of a discount linen store. But I started there I was made a manager within three months, it was a total catastrophe of a company. As far as like working there within retail, it’s something that I look for people who have also worked in retail to see if you could do that you could do anything. I managed mostly women, many of whom were ages 40 to 75. I was 17. It was tough to earn the respect at that age. And I had to work really hard for that. The job was really painful. It was shoving really heavy bed into bags. I don’t know if you know it’s a comforter, a sheet said some other things all in one giant bag. And I had to shove them over my head all day long up into the shelving, and then folding hundreds of washcloths. So then we do that we do folding wash cars all day. And then we would just watch someone knock it all down in one swoop. So I think we can all agree retail hard. The things I learned though, I learned resiliency, I learned determination and I learned management because there’s nothing harder than managing at 17 when you’re still being managed at home by other people. And those were really good skills, and I honestly still think about it. My first boss, her name was Rosalind caisson. Hi Roz, if you’re out there, and I think about her a lot. She was a tough, tough lady.
Jeremy Burrows 4:17
So you know, folding all those towels and then wash claws and putting them on the shelf. It’s kind of like when you schedule a whole bunch of meetings and then your executive walks in and knocks all the towels off the shelf.
Shelley Trask 4:28
It’s exactly like it. I mean, it all travels to current current work for me, I remember what it feels like. That’s why when people get really upset when things change at work, I say hey, this is literally our job. We just you just do things and things change and you have to be able to go with the flow. Yeah,
Jeremy Burrows 4:45
definitely. So when in Why did you become an assistant?
Shelley Trask 4:52
So I did the retail for a year and a half obviously quick to get out of that went to administrative roles. Recognizing my skill set was very much computers, software, organization. And that’s kind of my personality type. I worked in an advertising agency I did 10 years at an environmental consulting agency in Berkeley, when I first landed in the Bay Area in 2002. And then 10 years later, all of my friends were working at startups, they were making a lot more money, and really seemed to be happy, they were getting free lunches, they were getting all these perks. And I thought, you know, 10 years is a good run. So I went in 2012, I officially changed my title from office manager to executive assistant. And recognizing that I had actually been doing that job for all this time, but didn’t really know about that role, didn’t know it made more money, didn’t know, I could get more prestige, and respect. And so I started at a company called Livefyre. And they were acquired by Adobe, I believe in 2014. I lasted there for about two years, and then went on to do other things.
Jeremy Burrows 6:01
So what do you love about the role?
Shelley Trask 6:04
I love the autonomy, I love the I get to be very close to the top level of every company I’m in without having to be the C-level executive. You know, and I think as many of us who work closely with them, we often probably say, I’m really glad that’s not my job, I’m really happy to be a supporting character to be the person behind the curtain. It’s a tough job, I wouldn’t want to travel the world constantly. But I love making it happen and making it happen really seamlessly for them. There’s just a lot of joy, the devil is in the details is something I say a lot, because it’s really, I’m a very detail oriented person. And actually, that’s one of my weaknesses is I often have to take a step back. And I rely on my co workers who have strengths, in sort of the bigger picture stuff to say, remind me if I’m thinking to my grow here, when I, you know, when I need to get bigger. And so I just think it’s an amazing role. This role didn’t exist, you know, we had secretaries. We’ve had office management. And in the end, we were, you know, I think part of it that allowed the power to build and the real relationships to build is the respect for the role and understanding of the value that this role provides.
Jeremy Burrows 7:16
Awesome. So tell us about one of the bigger mistakes you’ve made, and maybe specifically in one of the startup environments.
Shelley Trask 7:27
Yeah, so I have one personal one professional. So personally, I think not leaving a boss when I know that the boss isn’t a really good fit for me, or that I’m not going to learn anything more from working with this person or from working at the company. So something like if the company doesn’t really understand what the role is, I think, you know, I probably should have left earlier. Professionally, I did something really stupid. It’s very, a very minor thing. But I once did a really dumb thing when making duplicates of calendar invitations and g-cal. My company was trying to court multiple companies for an acquisition. And I was rapid fire sending out meeting invites that were really, really detailed. So I wanted to avoid recreating the wheel each time. But I once accidentally had the wrong name and an invite. And that was not cool. Luckily, the recipient didn’t figure it out. And I turned out fine. But just a reminder, even if you think you’re type A you think you’re perfect. You need to check your work three times.
Jeremy Burrows 8:22
That’s a that’s a good reminder. Yeah. So what’s maybe a productivity hack that you can’t live without?
Shelley Trask 8:33
So when I was in the world of Gmail, which was most of my career, I couldn’t live without boomerang. I needed boomerang. So I you know, if I’m writing to somebody, and I’m waiting for them to respond, I would always have a boomerang so that my boss wouldn’t say, Hey, did you ever get that meeting scheduled? The other one was the LinkedIn Sales Navigator, which used to be called report IV. It is a really great way it’s a plugin, it’s a really great way for you to see who you’re writing to, so that you can address the gender properly. I would write to a lot of people whose names I couldn’t tell if it was you know, Ma’am, sir. And it was really kind of intimidating. It’s like, oh, my gosh, if I get this wrong, you know, and then of course, if you’re working with Japan, that’s a whole other level. So the LinkedIn Sales Navigator is great. And then as far as working at Slack, there are a ton of, of tips like you know, marking unread saving to Slack bot to remind you later. There’s a lot of ways to prioritize your sort of workflow in Slack.
Jeremy Burrows 9:30
So, let’s talk about Slack a little bit. Why don’t you all use email internally?
Shelley Trask 9:42
Well, once you stop using email, you will understand why it first it’s like whoa, well, this is very strange. I loved email I was I thought I was the master of Gmail. I have all my labels, I had timezones now I find it really painful to email. I’m really bad. My inbox is is a hot mess. And it used to be inbox zero. But we don’t use it internally at all, because the product actually completely replaces the use of email at Slack. So we do use email externally, I do need to talk with candidates externally, I do you know, if I’m going to schedule a meeting with my boss, I will obviously reach out via email. But then I try to move it into Slack as quickly as I can. So we actually have a plugin that allows me to forward emails from my inbox into Slack. So if I want my boss to see an email, I actually just forward it to him in Slack. And he doesn’t ever have to go into his inbox because he doesn’t at all use email. We also have a really cool feature that allows an external party to email me and I can reply to them from within slack. And they think that I’m emailing them. So it just looks like email to them. We can go back and forth, and I won’t need to use email, but they have the option to join a shared channel with me and slack and your channel is a term for basically I have a channel with for instance, you and you’re not a part of the company, but we have a private channel together. So it’s something you can use for vendors, or for kind of one offs like travel agents.
Jeremy Burrows 11:08
So I’m personally a fan of email. And I like slack when it comes to communities like online communities. kind of forum type format, I have a hard time with slack in the sense of people pinging you all day, it feels like people texting you all day. It’s I don’t like personally, I don’t like how it’s organized. In I can’t I have a hard time organizing it the way that my brain works. So what would you say to people like me that are listening that are kind of in the same boat where they’re like, you know, I like email, I like the, you know, the order that you know, the visual visual order that it’s in? How have you kind of helped people embrace slack?
Shelley Trask 12:00
That’s a great question. Because obviously, when I started here, I had not used slack very much I used it very casually the way that you’re describing for DMS, at my last company, basically, if there’s a visitor, I’d say, Hey, your visitors here, and that would be a Slack message. But that was really the depth of usage. So when I when you join slack, the company you are in for a wild ride, or onboarding is two and a half days. It’s a very intensive onboarding, I’ve heard it’s phenomenal. And then on top of that, I, if you’re an admin, the admin team will then onboard you for another, you know, rest of the week. And then obviously, we give you a little bit more time to acclimate, because you have to learn how to use the software. So I think that one of the things you’re bringing up about it being sort of not easy for you, I think the number one thing is you have to learn the shortcut keys and you have to learn the shortcuts. So knowing that you can find any channel by its name by pushing Command K, and it brings up a little finder box, basically, you just start typing and then all of the channels pop up. I do everything in shortcuts all day. And when you you retrain your brain with the shortcuts, everything you do is infinitely faster. I don’t think people are always optimizing for shortcuts. And that’s that includes in Gmail, too, like the Google products have wonderful shortcuts as well that a lot of people don’t use. So number one, like get to know your shortcuts, you won’t have to look for anything, because you just use the search command. You can also do things like marking unread. As far as being interrupted by a bunch of DMS kind of the way you’re feeling like Whack a Mole. What I do is, you know, I look at urgent DMS from people depending on who they are, obviously, something from my boss might be priority over someone who’s like four levels down. I also can mark them unread, or I can have them remind me tomorrow to ping that person, which is great. So it’s kind of like, for me the slack bot feature is the same as boomerang in Gmail. So really learning how to use that slack bot. And slack bot has a feature in the last I’m not sure how many months but we’ve integrated it so that you can, you can say remind me to you know, in exactly 9am In three days to ping Jeremy. So it’s a little more dialed in just like boomerang as the other one is, you know, I’m looking at urgent DMS, I’m looking at responses and threads. And I’m looking at updates that are high priority channels. And that’s where my attention is focused. So I think one of the issues people have when they start using Slack is learning how to focus their attention in the right places. I first started here, and I was looking at every single bolded channel thinking that it was something I needed to read. But it’s not the same as having a notification, which is a number symbol right over one of your channels. So just like really learning the product and we have amazing training online for free. There’s a blog, there’s all kinds of written documentation. And I actually have a channel where I teach people as well.
Jeremy Burrows 14:55
So yeah, so I’ve learned things like okay, I’m going to star The, you know, VIPs that I have to talk to all the time because I’d rather just go click their name versus trying to do a keyboard shortcut or type in their name and have to find the direct message. But then in then I’ve also done things like I mute a bunch of channels. But, but they so that they don’t come up in a bold way notification, but they they’re kind of, they do show up when there’s something unread, but it’s not as urgent feeling right? Um, so I do like those kinds of things. I think my biggest thought, and I wonder if you have like a hack for this, my biggest thing, the reason I like email is I like to see things in order of, of, basically, when they were received. And I have a hard time organizing my my slack in that way. Because I just always feel like I’m jumping around. And I’m like, I would just like to go through an order of, you know, in order of receipt.
Shelley Trask 15:57
Yeah, I can I understand that, actually, because I do like that about email as well, because you have the sorting feature, as well. I do think that there are some things that our product will be improved upon to look forward to in the future as far as sorting and being able to take a little bit more control over the channels and the way that you look at them. So I’m looking forward to that. But I do think, I guess because I’m so current on Slack and up to date. I’m not concerned with exactly what time something was sent, because I’m usually looking at it. But I guess if you’re a casual user, and you’re using it for like a social group, I could see that. And then the other thing I really want to stress is, I also think one of the reasons people don’t enjoy using slack when they first start is that others are not threading properly. So your Slack page, your channel should not look like a bunch of discussions. It should look like a topic, and then threading, another topic and then threading. And if people aren’t willing to make that commitment to each other to use it correctly. It’s really hard to read. I’ve looked at other people’s slacks and just can’t believe what it looks like. It’s impossible at that point. So I think there’s some best practices to establish as well. Yeah,
Jeremy Burrows 17:12
I agree. And I feel the same way about looking at other people’s inboxes. Oh, how do you even? Or sometimes I’m like, maybe that’s why you’re not getting anything?
Shelley Trask 17:23
Yeah. Or I think well, you must be a master searcher. That must be your strength. Yeah.
Jeremy Burrows 17:28
Awesome. So what is it like working for fast growing large company and a lot of people have heard of a lot of people use? What are they’re kind of some pros and cons to being in a company like that.
Shelley Trask 17:46
Definitely. It’s incredibly exciting. And slack was definitely, let’s see, I probably the only company I had heard of that I joined, you know, before joining. When I saw the job opening, I thought to myself, Wow, I don’t know, like that’s a company I’d really like to work for. That’s pretty intimidating. I don’t even know if I could get in there because I haven’t worked at a company that big. So we grew from 1000 people to around 2000 People in under the two years I’ve been here. It’s been really hyper growth for a long time. And our admin team has grown from around eight people to 24 people now. My engineering admin team alone has grown from just me to eight people. But I love working here, it’s number one, Slack is the friendliest company you could ever work for people are genuinely excited that you’re here. And they care about you and what you have to say, first workplace. It is a kind of workplace we are I think thoughtful before we say things, you know, like take a take a minute, think about what you’re going to say does it really affect people appropriately? Even as we’ve grown so quickly, we’ve managed to maintain that. And I think another thing that is kind of because the software we make and use every day has such visibility and transparency. There’s a transparency to the company that is built into that. So you see a lot of what is being written in channels that are social channels that our work channels, you see the way your coworkers are writing and what they’re talking about. And it alone, like by being able to see what people are saying and comment on it and people reacting to what you say it creates a camaraderie as well at Slack.
Jeremy Burrows 19:30
So how have you navigated your own career growth in the midst of the overall company doubling in size?
Shelley Trask 19:40
Yeah, obviously, the growth of the company is directly tied to my ability to grow as an EA. And that’s something that I’ve been seeking for a long time in my career. I’ve worked at smaller companies, you know, really startups that were 40 that got really up to 200 Max. And I often felt like after a few years years I’ve maxed out my ability to really tackle big problems and create new processes, which is my favorite thing to do is to come in and fix things, and figure out how to make them better. Working in a fast growing company means that I have yet to run out of interesting problems, or solve or things to improve upon. So basically, there’s every day there’s a new challenge here. One example recently that I’m really proud of is our admin career path. When I started, we had a career ladder that was recently adopted. And in reading it, a lot of us were sort of like, well, I don’t know that this applies to me and my career here, I don’t just, it was very opaque. And when we’d have career conversations, or bosses would say, I don’t really know how to figure out where you are on this ladder. And so a small group of us recently completely rewrote and recalibrated our path based on our company values, and the strengths and qualities that we believe successful admins possess to be valuable players here. The path is, it’s actually being passed to HR to our principals for adoption, I think today. So that’s a really good feeling. It’s awesome. Yeah.
Jeremy Burrows 21:03
So what’s the word of the company values?
Shelley Trask 21:06
So we our company values are smart, humble, hardworking, and collaborative. And we mapped the values to job knowledge is smart. Communication is collaborative business and org impact is hard working. And communication is collaborative. And I get all of that. Yeah. So it was it was pretty fun to do. It took a lot of work.
Jeremy Burrows 21:36
So this kind of segues to the next question, what should assistants be doing to advocate for themselves when it comes to responsibilities, compensation and respect? So you talked about, hey, you know, we’ve kind of redone the career path for the admin team. What are some other things that assistants can do to advocate for themselves?
Shelley Trask 21:59
So I hear a lot about people feeling like they’re not getting the respect that they deserve at their job. And I want to make sure that they’re earning the respect as well. I would say first, make sure that you work at a company that recognizes what you do, and the value that you provide, like do they understand the role when you’re being hired, if you’re interviewing with them, and they’re bickering about what the role is, that’s a good way to step out of that interview, I’ve actually left an interview before, where people didn’t agree with the role was. Second, make sure that you represent that value. So be professional, go that extra mile to make your work look beautiful, fix the spelling errors, refine the presentation, make yourself invaluable, and a key player proactively tackle projects, don’t wait for someone to tell you what to do. That’s number one way to earn respect, and to advocate for yourself. Once you continue to provide that value, you should be able to create a case for yourself for compensation, keep track of your major milestones and have career conversations often with your manager. If your manager isn’t great at it, because let’s face it, executives, often are not good managers. They’re wonderful executives. And to be really successful. As an admin, I think you need to be your own self advocate. Get to know their chief of staff, get to know your HR business partners, your managers, peers, as well make sure that they know the value that you deliver. Don’t be shy, I have another EA here who always reminds me of what someone wants told her. She says you are in the business of you. That is it. That is your business. So if you’re not reflecting, you know, your own image upon the world, like you’re not doing the job, you’re not here for anybody else. That being said, of course, you are also here for your company, right. But I would also say respect comes naturally when you’re being professional when people see you working hard, and also delegating when you should delegate because there’s respect around that as well. You know, don’t be a martyr, don’t kill yourself, if you don’t have to. Being clear about expectations on what you can deliver, having strong communication, both verbal and written skills, all of that creates respect. And if you’re doing all of this, and you’re not getting anywhere, it’s time to leave. We’ve all been there. I’ve had my own regrets that I didn’t leave certain situations sooner, but in the end, you have your own path. You have to trust your instincts.
Jeremy Burrows 24:13
So could you talk about your team? So how did you grow the team? And do you have any tips for interviewing?
Shelley Trask 24:24
Yeah, actually, another project we did was we wrote up new interview questions. So I try, I tried to reach out to my networks. And sometimes that works, and sometimes it doesn’t. I’m also a member of an administrative group called org. org, which is a free group that anybody can join very, very valuable and helpful. We historically at Slack, we’ve used recruiting agencies to help us find high caliber candidates here. But I’m also not afraid to go on LinkedIn and cold email someone I’ve made connections this way, even if I don’t get a higher out of it. It’s kind of a long term relationship. An interview tips. I love this one. So another EA here. I think it was her husband who asked this question. So we have a question now that we use, which is what’s your zombie apocalypse plan? It’s so good. There is no right answer. I’m looking for what your face says. When I asked you this question. Are you funny? Can you be funny? Can you come up with anything on the spot, which is our job? Really? Anyways? Like you have to figure out things on the spot. That’s the whole question. And people who get kind of thrown by it. This is about improv, you know, being a good eight is the art of improv.
Jeremy Burrows 25:37
Yeah, that’s great. Yeah, I like the zombie question. I always, always, I love apocalyptic shows and movies and thinking about end of the world scenarios and prepping for my end of the world scenario, maybe that’s why I’m a decent. Of course, my wife’s always like, why, like, No, I don’t, I don’t know why you think like that, like, Well, somebody’s got to be prepared if it happens.
Shelley Trask 26:05
I do think that’s an easy thing.
Jeremy Burrows 26:08
Awesome. Well, Shelly, thanks so much for taking time out of your day to share your tips and tricks, a little bit of your story. I’m going to close the interview with one of my favorite questions, what makes an assistant a leader.
Shelley Trask 26:24
So you’re a leader by design, I mean, you are truly leading the pack in your role and supporting your executive properly. You are a leader, because people see you leading. I think that respect is tied in with that as well. And your lead by example. So you’re leading not only your company, but you’re leading the people who you hire to work with you on your team, by example. Have one more thing I would say to go with that? I would say do great work. Be appropriately assertive. Speak up when you have good ideas. fight against injustice for both yourself and your co workers. Don’t be an asshole. tackle problems, even if you might not get credit for it. Or if people will not know who did it. It doesn’t matter.
Jeremy Burrows 27:17
Yeah, like the you know, when we started our company, one of our there’s six of us day one. And I think it was probably that day we talked about can we make it a rule not to hire assholes.
Shelley Trask 27:31
That’s definitely one of our rules at SLAC. Don’t hire assholes. And if you notice one, say it like
Jeremy Burrows 27:40
Well, is there somewhere we can find you online or support what you’re doing.
Shelley Trask 27:45
Unfortunately, I don’t have much of a an online presence. I have a website that I probably should do something with someday. But for now LinkedIn, definitely find me in the org.org. I’m a I’m a volunteer for org.Org or run a Slack workspace training people on how to use Slack and all the best practices, much more than I’ve discussed here. So I very much invite you to join that workspace through the org. org website. But I look forward to joining more and doing more good work for other admin occasions.
Jeremy Burrows 28:15
Awesome. Well, thanks again, Shelly. Keep up your good work with slack in your your EA teams. Yeah, it’s fun to fun to see you all grow and get kind of help companies and help communities connect and get out of email.
Shelley Trask 28:35
I promise we’ll get you there someday.
Jeremy Burrows 28:37
We’ll see. We’ll see.
Shelley Trask 28:40
Thanks, Jeremy.
Jeremy Burrows 28:42
Thank you again, Shelly for a great interview. Episode 65 Show Notes are at leaderassistant.com/65. And again, the book comes out in a little over a week. So leaderassistant book.com/events to join Monique Helstrom and I for a launch party on June 23. Talk to you next time.
Unknown Speaker 29:18
Please move you on Apple podcast. Goburrows.com
