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Rachel Tan’s EA Cheat Code: What Outcome Do You Want? · CCing my EA Podcast

• 0:00
  Welcome to the CCMA podcast, where we interview executive assistants about the real tactics and stories they've learned from supporting busy executives.
• 0:07
  This episode is presented by Vimcal EA, the first calendar built specifically for executive assistants. Today, I'm here with Rachel Chan, who is the director of executive administration and strategic programs at Benchly.
• 0:18
  Rachel, thank you for joining us. Thank you for having me. I'm excited to be here. I'd love to just kinda learn a bit about how you ended up as an EA, and then we can kinda take it from there. How did I end up as an EA?
• 0:28
  Okay. I guess I didn't, I didn't start as an EA. I, previous to, like, being in tech, I worked for the government, and that was, like, slowly killing my life. And then my, you know, I li- live in San Francisco.
• 0:45
  I've been born and raised in San Francisco, so everybody was talking about tech. Everybody was in, like, cool new tech jobs and, you know, like, Twitter when it first started.
• 0:53
  I was going to the Twitter office with my friends and, like, eating their free lunch, and I was like, "What the fuck is all-- What, what is this?" And I got in as, into tech, into the tech space, uh, in Workplace.
• 1:04
  And w- we didn't call it Workplace back then. We called it, like, an... I was, like, an, an office manager. And as part of that job, I kept absorbing more and more things. Okay, we were a Series A company.
• 1:18
  We had 40 people in HQ, and starting at W- at Workplace Lead, and, and it stretched, right? I started doing recruiting.
• 1:26
  I started doing office culture and events, and then picked up executive support for the three executives that were in the company.
• 1:33
  I was with that company through acquisition for, uh, was with them for four years through acquisition. And when I was looking for a new job, I was like, "You know what? What do I, what do I like about my job now?
• 1:43
  Like, what do I wanna focus on?" And my next move made it official. Like, I stepped into a dedicated EA role, and the transition felt less like a career change and more like a, a narrowing, right?
• 1:54
  Um, and I really feel like most EAs I know don't start out as being EAs. Yeah. A hundred percent. They just kind of, like, fall, they fall into being an EA, and they're like, "Oh, I'm really good at this," and here I am.
• 2:05
  It's 20, 15, 20, 20 years later. How old am I? It's been a while. [chuckles] Okay. I actually prepared a couple things here. I didn't realize that you had previously been on a podcast. I was previously in a podcast, yes.
• 2:22
  Okay. So- It was really fun. Uh-huh... what does it mean to be an EA in a war room? Yeah.
• 2:28
  I mean, war room, to me, it's really just being in the same place where all the decisions are made, whether that's a table, it's an actual room, it's a Zoom meeting, right?
• 2:36
  But, like, being in the place, and you're part of those conversations where the big decisions are made.
• 2:42
  For instance, for our company kickoff, our war room is literally a room where everybody who's part of the planning team and, like, running the event goes to meet, is where we start the day and end the day, and where we spend our breaks.
• 2:56
  When you're talking about something, like, in the company, it could be, it could be a Slack channel for big comms that are happening the next day, right?
• 3:04
  We're announcing an IPO, or we're announcing a RIF, and we all need to be on the same page in real time. It's a really special place because you have to be on your toes. You have to pivot very quickly.
• 3:19
  You have to know how to execute also very quickly and read the room and everybody in it, [chuckles]
• 3:26
  and, you know, bring things up that other people are not seeing, like surface other opinions, surface other views that are not in the room also, right? And that's something that you have to think about.
• 3:36
  Is there a certain thing acr- that's similar for, like, what you bring to the war room across these? EAs are, are, are a really special place in the business because they have the ear.
• 3:48
  They're our ear, they are ears and eyes, right? They're really the bridge between what's on the ground and what's happening at the top level.
• 3:54
  It's very important to me to be able to make sure that I am the voice for people who, like, aren't in the room, even though that sometimes makes me a really squeaky wheel, or it makes me seem like I'm a contrarian.
• 4:07
  But that's my, that's my job, if I'm in the room, is to speak up. So if I'm in, you're gonna hear all about it. [chuckles] I see.
• 4:16
  So, like, you would say your biggest, the main, like, value you wanna bring when you're in these rooms is the unheard opinions? I don't, I w- I don't call them opinions. I would say that they were unheard experiences.
• 4:29
  Mm. I would call them, you know, things that are happening that have yet to be surfaced or spoken aloud, right?
• 4:38
  Because I think there's a very big difference in, like, sharing an opinion versus, like, sharing an experience or, like, sharing something that's fact-based. Yeah. Mm-hmm. That's interesting.
• 4:46
  So I, I, I, I think you're, we're saying the right things, but the verbiage I'm sensitive about. [chuckles] I totally get it. I love that. Yeah.
• 4:53
  Um, so speaking of, you know, what's being talked about and what's not, one specific thing for EAs is you have...
• 5:00
  You know, you, you know a lot of stuff, um, that other people might wanna know, but there's a gap between that and what you're actually allowed to say. So does, that seems a Spark like a moment. Yeah.
• 5:12
  Does that remind you of anything? This job is very lonely, and, and that's twofold. One, because you're typically the only person with this scope in your org or in your department or on your team, and two,
• 5:28
  because you have all this information that you can't readily share.
• 5:31
  And that feeling can be very isolating because you want to share all the good things with people because you know they're gonna be really excited, and you also want to share, like, bad things so you're not alone in your anxiety and misery, and, but that's also, you know, it's also part of the job.
• 5:46
  I think it's very important to have EA community because of that reason. Like, yes, I'm the only EA in, for instance, I was the only marketing EA, but I made other department EAs my community.
• 6:01
  I could commiserate, right, with people without spilling the beans, and they would totally understand.
• 6:05
  Whereas other, with people outside of the EA community, they kind of, like, goad you into telling, like, or trying to goad you- Mm-hmm... into telling your secret. Like, "Hey, what do you know about this?"
• 6:14
  Or, you know, like, trick you into, ask you trick questions to try and get you to spill the beans.
• 6:18
  But EAs have that kind of mutual respect and understand that, like, I know they can't say anything, but I'm here, I'm here to listen, and I'm here to, like, walk you through whatever ledge you're on.
• 6:30
  Do you have an example of, like, a, this super big secret that maybe you're now allowed to share? So, like, for instance, I knew that, uh, one of my previous companies was going to be acquired very early on,
• 6:43
  and lots of things were happening. You know, we were business as usual up until we announced the acquisition, as we had to be.
• 6:51
  So parallel processes of being in meetings, knowing that the things that are talk- being talked about in that meeting aren't actually going to happen was really fucking hard. Oh.
• 7:01
  And then acting like, and being the responsible person for this action item, for this thing that I know can't happen just puts you in a really f- pickle. It puts you in a pickle, right?
• 7:12
  Because you have to do the work, because you don't wanna be seen as somebody who doesn't do their work, right? Your name's against it, but you also are like, "Why am I doing this?"
• 7:20
  Because I know it does- it's not, it's not gonna matter. It's not gonna matter in two weeks. Dang. Because [laughs] That is tough. And you're saying the way you deal with that is with your, what, with EA community?
• 7:32
  Yes and no. If somebody is also, if another EA is also in the know, I then make that person my sounding board. Like, "Hey, how are we dealing with X, Y, and Z?"
• 7:44
  If I am the only person who knows, then I just, like, stress eat. Oh, no. [laughs] I stress eat, and then I hide in meeting rooms so nobody asks me questions that I'm uncomfortable answering.
• 7:57
  I'm also a very bad liar, right? So, like, putting myself in a position where I have to lie to people is not something that I can do comfortably. Um, so yeah. Work, I, working from home [laughs]
• 8:10
  really helps during those periods. [laughs] Is there something you feel like new EAs might not quite get about confidential information? There's a difference between confidential information and sensitive information.
• 8:24
  I think there's a line when I, when my, like, for instance, when I was first being an EA, I, I treated everything as confidential. What does that mean, treating everything as confidential? I was a black box.
• 8:36
  You, I would give nothing away. You would ask, and I would say, "I don't know. Ask your boss." In the nicest way possible, obviously.
• 8:43
  As a new EA, I think under- understanding what's confidential versus sensitive and understanding the threshold for your executive and what that level, what that tree of trust, I guess, looks like for them can help you mitigate those things.
• 8:58
  Do you have examples for sensitive versus confidential? Also, like, how do you treat them differently? Sensitive versus confidential. So for example,
• 9:07
  something that's confidential, I previ- uh, what I previously said was, like, we're about to be acquired, and I can't tell anybody.
• 9:13
  Something that is sensitive, for instance, I had a department that was going through a reorg. Mm-hmm.
• 9:18
  And I had to share with the other EAs, like, "Hey, this information, like, what, this is, something big is going to happen, and I need your help in cascading comms," right?
• 9:29
  And we built this entire comms plan that needs, that needed to happen, and many hands had to be involved. So sensitive being, and, and using, going to use the, the exact same example.
• 9:40
  Sensitive being something big is happening. I have a part in it. Here's how I can help you help me. Mm-hmm. Confidential being what exactly that thing is. And I think that really depends on who you're talking to, right?
• 9:54
  'Cause I could be talking to the CEO, where nothing is confidential, and I could be talking to the COO, where some things are confidential.
• 10:02
  So again, like, really understanding who the tree of trust is for specific situations can help you decide if something is confidential versus sensitive. I have a question that I've been asking every guest.
• 10:14
  What is one small tactic or habit or rule that you've picked up that made your job easier? So I'm basically asking- Yeah... for your EA cheat code. When an exec comes to me and says, "Rachel, like-" Hmm...
• 10:26
  "this is a thing that happened," instead of me leading with my take on it, I lead with, "What is the outcome that you want from this? Okay. How do you feel about this? What do you want to happen?"
• 10:38
  That gives me a lot of context for how they want me to show up for them versus... And it's just a l- it saves so many cycles for me, and, like, my brain space.
• 10:49
  And, uh, 'cause early in my career, I was like, "Here's, you're coming to me, Johnny. You're my executive. You are coming-" Mm-hmm... "to me with a problem. I, as a new EA, am coming to you with solutions.
• 11:03
  I now, as a seasoned EA, am asking you, what is the outcome that you want, and let me help you get there, instead of me coming to you with, like, 17 different solutions and, like, here's the outcome of that.
• 11:14
  Like, 17 different outcomes." So it just saves so many cycles, and it also gives me context that I can use for, like, future situations, right? You, Johnny, didn't like when this person said something to me today.
• 11:29
  When that person says something to me tomorrow, I'm gonna assume you're also not gonna like that because you didn't like it today, right?
• 11:34
  So you're giving me precedent, and you're also giving me context that you're not necessarily giving me upfront. I imagine sometimes people don't even know what they're, they want out of you- They don't know...
• 11:43
  too, though. And it really makes them think, right? Like, "Oh, I've, nobody's ever asked me that." Like, I've had, I've had execs say that. Like, "Nobody has asked me that. Thank you for asking. This is what I want."
• 11:54
  And then I can come with my take after. Like, I, uh, I'm very opinionated, [laughs] but my opinion doesn't come primary to what my exec needs and wants.
• 12:03
  If I feel very strongly about, "That, that's not the right thing to do," I will say that, right? And then it's a discussion. Like, it does make people- Think about what it is exactly that they want.
• 12:13
  And sometimes they have to come back. They're like, "Actually, I don't, I don't know. I don't know what that is. Let me come back to you." And then it's a topic for discussion on our next one-on-one. "Hey, you said this.
• 12:22
  Have you decided, or is it no longer a problem?" 'Cause sometimes that happens, too. Is there a lesson you've learned only by getting burned once? I had an exec...
• 12:31
  I like to build trust very early with my executives and, you know, being the eyes and ears of their organization, you know, information comes up and comes down, right?
• 12:41
  I had an exec once tell somebody else, like, "Oh, hey, I heard this happened. Rachel tells me everything." And- Oh. Right. Exactly. Oh, no. [laughs] Like, why would you fucking say that?
• 12:55
  And so it didn't erode trust between me... Actually, I should rephrase that. It eroded trust between me and, like, gen pop, right?
• 13:05
  Because that was like, "Rachel tells him everything, so don't say anything to Rachel," right? That came, that trickled down that person's org. But it also eroded trust between me and my exec 'cause I was like, I don't...
• 13:15
  Well, I, what we s- uh, what I say to you is not so you can tell on me, right? And, and vice versa. Like, you say things to me and I'm not gonna go tell on you.
• 13:24
  But it really opened my eyes to, like, my level of discretion is not always my exec's level of discretion, and needing to state upfront what this relationship looks like and what I expect out of it moving forward.
• 13:38
  So now anytime you're sharing information, you do, do you add, like, a extra, "By the way..." Yes.
• 13:43
  Now it's like, hey, almost every, at the end of every one-on-one, I go through, like, what we talked about today, and to confirm, like, here are the action items that I took down, right?
• 13:53
  Here's what you own, here's what I own. But also, is anything here confidential or sensitive? Mm. So getting that upfront at the end of every meeting- Yeah...
• 14:00
  and coupled with, like, all of our action items has helped everybody stay on the same page. Have you ever had a moment where something almost was a disaster, but then you, like, caught it right on time?
• 14:11
  Very recently, I planned a board dinner for a restaurant that has two locations. Mm. Okay? Oh. I, I did all the right things. I confirmed what location it was at, confirmed the time, told them I was going to be there
• 14:28
  to drop down place cards, because, you know, that's what we do at every board dinner. I, m- you know, do seating arrangements, print menus, all the things. I get to the restaurant.
• 14:39
  They don't have any of this information. I thought I fucked up. I was like, "Oh no, did I make this reservation for the wrong place?" So I'm sitting in front of the manager on my phone looking it up. Like, no, okay, no.
• 14:51
  I did not fuck up. My reservation is confirmed for here in 15 minutes. But they had it at their other location. They're like, "What?" And they were like, "Can you send your people to the other location?" "No.
• 15:02
  They're coming in 15 minutes. I'm not making them turn around. Can you fix this back table for me now?" They made it happen. It ended up being okay. Was it great? No. They were not prepared for 20 executives to be there.
• 15:16
  It was not the level of service I expected of this restaurant that I have been to before, that I love, that I know very well. They did the best they could with the time that they had.
• 15:27
  I did the best I could with the time that I had. But that was almost a disaster. A common problem a lot of EAs have is in showing their impact.
• 15:35
  So, uh, today we talked a lot about confidential stuff, sensitive stuff, or where, you know, the success is in fact that nothing happened, like, that was the success.
• 15:45
  But then how do you demonstrate the impact on these things that you can't talk about or you can't show?
• 15:50
  Previous to last year, it was literally, like, reflecting at the end of every week, like, what did I do this week, and writing it down. What did I do this week? Who did I help? What do I need to pivot for next week?
• 16:02
  But now, now that I have AI- [laughs]... um, that has been super helpful, right? Because we have an enterprise, we have an enterprise Claude account, and at the end of every week I do the same thing.
• 16:14
  "Claude, what did I do this week?" And Claude is connected to my Slack, it's connected to my email, it's connected to my Zoom, it's connected to my transcripts, like, everything. How did I show up this week?
• 16:26
  How can I show up better? How was my tone? What did I spend time on this week? What did I actually get done?
• 16:31
  So I have a rolling log of, like, all those things happening week to week, and then I can do, you know, just like I do for my exec when I do, when we do audits every quarter, right? What did you...
• 16:41
  Did, did you actually spend the time on the things that you said were important? Right? Um, how should we rebalance your calendar looking forward? I do the same thing for me. And Claude has really helped with that.
• 16:54
  [laughs] We've made it towards the end. Let's zoom out a little bit. Is there, uh, what is the most unusual or proudest thing that you have done for your exec?
• 17:04
  The coolest thing I've ever done is, and this goes personal, okay? I p- planned a previous exec's big birthday party. Mm. I mean, multi-international,
• 17:17
  tens of people, like, I think it was, like, 40 people, private jets, many different countries, like, start to finish, planned his birthday party. [laughs] Um, and that to me was really fucking wild, because
• 17:36
  rich people are insane. [laughs] Mm. Was this for, like, a 40th or something? Like, a, a new decade? 44. 44? Interesting. 44. Yeah. Yeah. Nice. Well- Super cool.
• 17:51
  [laughs] Uh, and despite all the chaos that comes with the job, what is still most fulfilling to you? I am, I'm an eldest daughter with ADHD, okay?
• 18:03
  Which means I'm very type A and I'm a people pleaser, and I get to be all of those things in this job with authority. So it, like, tickles my brain in the way that it needs to be tickled.
• 18:15
  But going back down, I am, like, it is ve- it's fulfilling to me to be the bridge, it's fulfilling to me to be the ear that people trust, right?
• 18:25
  Like, people trust what I say, they trust my work, they trust my work ethic. And, like, being in a place where I feel valued in that way is incredibly meaningful to me. Excellent.
• 18:38
  Well, that's it for this episode of the CC My EA Podcast. Thank you, Rachel, for coming on and sharing your tactics and stories.
• 18:45
  If you liked this episode, subscribe to CC My EA for more practical EA stories and tech tips.
• 18:50
  And if heavy calendaring is part of your role, check out the Cal EA, the first calendar built specifically for executive assistants. See you next time.