Sarah Calderon on the Strategic Partnership Between an Executive and their Assistant

Sarah · 0:00

I'm Sarah Calderon, and today's leadership mantra is Lead with Humility.

Speaker 3 · 0:11

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

Jeremy · 0:26

Calling all Executive Assistants, are you looking for a way to elevate your skills or earn that promotion you've been eyeing? Nova Chief of Staff's Online Certification Course provides you with the knowledge and confidence you need to stand out on the job. Whether you want to land your dream position or level up in your current role, Nova's self-paced course gives you hands-on practice doing what Chiefs of Staff do every day. Visit leaderassistant.com/nova to learn more and secure your spot. That's leaderassistant.com/nova. Hey friends, welcome to The Leader Assistant Podcast. It's episode 266. You can check out the show notes for this episode at leaderassistant.com/266. leaderassistant.com/266. And I'm just going to give you a fair warning. My vocal cords are a little bit tired. I've been battling an illness. I'm finally coming out of it, thankfully, but my voice is not quite 100%. So you're going to get the low and raspy and nasally Jeremy today, but I figured, you know, I can't, I got to keep the show rolling, right? I got to keep the show rolling. So I'm very excited to be speaking with Sarah Calderon. Sarah is really connected with you, Sarah. I think it was on LinkedIn originally, right? Is that right?

Sarah · 2:01

Yes, we connected on LinkedIn.

Jeremy · 2:03

And so we've been trying to get this going for a while, and I'm excited to finally talk with you. You're the founder of Hey, EA, which is an online training platform for executive assistants. heyea.com, and you're a career EA, and we're going to get into all that. But first, tell us where you're at in the world and what your favorite thing to do when you're not working is.

Sarah · 2:31

Awesome. Well, Jeremy, thank you so much for having me. First of all, it's a pleasure to be here. I am calling in today from Dallas, Texas. I am a Texas native. This is home for me and when I am not working, so I am the mom to an almost two-year-old and expecting my second this summer. So for me, when I'm not working, thank you. So for me, when I'm not working, it is time at the playground. It is singing along to the Frozen soundtrack. That really fills up my spare time and I couldn't be happier about it.

Jeremy · 3:10

That's great. Yeah. Congrats. Congrats again. I have two kids and they are a handful, but they are a precious handful. So it's fun times. So tell us about your career. Where did you end up landing in the assistant role and then why?

Sarah · 3:31

Yeah. So like so many assistants, it is a job that I kind of fell into. I actually first started as an office assistant way back when I was in college. I was doing a work study job, worked as an office assistant for one of the departments on campus. And then a couple of years after graduation, I ended up getting my first role as an executive assistant. I worked for a big four. So that was kind of my first foray into the EA world. And now a whole decade has passed. I've worked for a couple of other companies, and I just love the position. I fell into it like so many other EAs, and I haven't even really wanted to get away. I love the role. I love what I get to do every single day. So it's been a really great career journey for me.

Jeremy · 4:31

So when did you say career journey? When did you realize that it was a career?

Sarah · 4:37

I think in my second position as an EA, my second company that I was working for, over time, you get more comfortable in your role, right? You add more value. You get to stretch yourself and do even more in your position. And that was really the role where I felt myself kind of settling in to who am I as an EA and what am I capable of. And that for me is where I said, this is for me. This is the position for me. And I'm just going to keep doing this as long as I can because I really do love it.

Jeremy · 5:18

Awesome. And then, you know, there's this term strategic partnership that I've talked about several times in this podcast. Talk about it with other assistants of the world, being an assistant myself. Just this idea that, you know, we're not just task rabbits. We are strategic partners. And so talk to us a little bit about maybe how you started to see your role as a strategic partnership. And what that looks like. And then maybe even challenges you faced as you've worked with executives who didn't see it as a strategic partnership. Or just even to your more recent roles, how that's been a double sided agreement of, hey, you know what, this is a strategic partnership. And, you know, yeah, so talk through that whole phrase that we hear a lot of. And practically speaking, what do you see your role as a strategic partner looking like?

Sarah · 6:26

Yeah, that's a great question. What is a strategic partnership? It's something that it's hard to define sometimes. So when I think about strategic partnership, a lot of times I think about the first meeting that you might have with an executive. So let's say, for example, you have just started supporting an executive who's new to the role. Maybe they've never had an assistant before. You're just supporting them for the first time. And a lot of times that conversation with the first conversation you have with that executive, it can go a little something like the executive saying, Jeremy, I'll pick on you, for example.

Jeremy · 7:10

You can pick on me.

Sarah · 7:11

The executive might say, Jeremy, I've never had an assistant before. I'm pretty self-sufficient. I'm not really sure what you can do for me, but I'll just let you know if anything comes up. I'll send you an email. I'll send you a Slack. You'll hear from me. And it puts you into that reactive space, right? That almost task rabbit space that you just mentioned. And, you know, when you've been an assistant for a little bit, maybe you redirect the conversation a little bit and, you know, start talking about how you can help them with their travel and their expenses. And maybe you have an idea of a few meetings that you can go ahead and start scheduling for them. And all of that stuff is super important. Travel, expenses, calendaring. I mean, it's kind of the backbone of what we do, right? But even still, the executive might end that conversation with you and say, thanks for the suggestions. I have a trip coming up next week. But let me just work out the details and get back to you. So once again, you're left in that reactive zone, right? And when you're sitting back and just waiting for them to tell you what they need, it's not really engaging in a partnership, is it?

Jeremy · 8:25

Yeah, I mean, it's like I've had dozens of conversations and coaching clients with assistants and I've talked to them and it's like, I can't get my executive to give me more work or, you know, that just what you mentioned, they say they'll handle it themselves. And that's not the back and forth strategic partnership that many of us assistants desire.

Sarah · 8:52

Yes. Oh, my goodness. I can't get my executive to give me more work. Yes. Every time I hear an executive say to me, I'm really low maintenance. To me, that's even a red flag. You're doing too much executive. You need to offload some of your work. But what does that work? Right. That's a question that's really hard to answer. So for any assistant out there who's looking for more work from their executive, looking to build that partnership, I have the solution. So reframing the conversation with your executive and asking the executive, what are your goals? What are your KPIs? What are you accountable to achieve this year? And what are your, let's call it, three to five high-value activities that are going to contribute to you hitting those targets? So really dig into that stuff with your executive. This reframes the conversation. You're now in a proactive position. You are asking them what are they trying to accomplish? What are their goals? What are their priorities? And is it going to shock a lot of executives to have you sit there and ask them all of these questions? It probably will. Yes. They're not going to expect that from you. But I have to say, I just had a very similar conversation with a leader just this week. So I was in the office and I ran into a leader who, he works in a different division, usually outside of the US offices. So we don't really work super closely together, but we know each other. And this leader was recently promoted. And he was telling me that he, for the first time ever, is now going to have a dedicated assistant. And he just had a big question mark. He didn't even really know what to ask, but he was just saying, Sarah, I feel like I need help because I don't know where to start. How do I really start giving her my calendar and different tasks? He didn't even really even know what questions to ask me. He just had questions. And this is how a lot of executives will walk into that conversation with you. Whether they're a new executive or maybe you're just starting to work with them for the first time, they don't know how to handle it. It's just a bunch of questions. So the first thing that I said to him was sit down with your new assistant and ensure that she is clear on what your priorities are, what your KPIs are, what are you accountable to achieve. And he looked at me funny and he just goes, wait, I'm going to sit there and I'm going to talk to her about my goals. It was a really puzzling moment for him. But I said, yes, absolutely. That is step number one. That is really where you need to start. And unless she's super clear where you are going, executive, unless your assistant is super clear where you are going, they can't actually help you get there. And once the assistant is super clear on what the priorities are, they can be more proactive, they can think like the executive, they can anticipate and understand where the executive needs to spend their time. So for this leader that I was talking to, this was a huge lightbulb moment for him. And Jeremy, this was like a super quick three minute conversation. I mean, we just bumped into each other in the hallways. We had to run to our meetings. We were about to be late to our respective meetings. We had three minutes, but I couldn't let him go without helping him out just a little bit. But in three minutes, he got it. A lightbulb went off. So for any assistant out there who may be concerned about having this conversation with their executive because it feels a little bit full on to just start asking them, you know, what numbers are you supposed to hit this year? What is your boss holding you accountable for? It can feel a little intimidating to have that conversation, especially with someone you're supporting just for the first time. They will be a little bit questioning why you're asking these questions. But in three minutes, I can guarantee they'll get it. And that is the conversation that really changes the partnership. That's how you start entering into a strategic partnership. It allows you to be less reactive, more proactive. It's a small conversation that's so, so impactful.

Jeremy · 14:02

Yeah, you know, it's funny you mentioned that because I was talking with an assistant and they were like, or actually, I was talking with a company group of assistants and, you know, it's like, OK, well, this is a common question I get, but how do I do more for my executive? How do I level up and all this? And a lot of assistants ask the question, how do I become a better assistant? And I actually think that's the wrong question. I think the better question is how do you do more of or how do I as an assistant do more of my executive's job? And so to your point, it's like, hey, what are your goals? What are your KPIs? What are you doing? Because my goals are your goals and my job is to help you execute your vision. And so that executive is like probably clueless because, you know, never worked with an assistant, doesn't know what assistant does. And it's like, OK, well, I don't even know where to start. And you're right to point him back to just start with what's your job? What are you trying to accomplish? And then they can come in and help you with that. And so I think a lot of the times assistants focus so much on, you know, well, what's the best tip and tips and tricks of being a better assistant? When I actually think the future of our role is how much can we not only put ourselves in our executive shoes and understand what they're doing, but actually wear their shoes every day and do more of their job?

Sarah · 15:40

Absolutely. It's kind of an opportunity, if you think about it, to share the load a little bit. And while an executive, of course, has direct reports and a whole team and there's a big team of people that are mobilizing around company priorities, we're kind of the only ones that are in the trenches in that way together with the executive when we're in that partnership mindset, right?

Jeremy · 16:07

Yeah, exactly. Awesome. Well, what else about the partnership? Are there any stories in your career where the partnership wasn't going well and you had to work through it or examples of how it may be some wins that you and one of your executives that you've worked with have accomplished together?

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Sarah · 17:15

I will say one thing aside from having this conversation, which is super important, but the other thing that I've done in my career that has really changed the way I've been able to build partnership with my executives is being a part of their team, and I mean that in the sense of I'm in all of their leadership meetings, team offsites, everything that they're doing along with their direct reports, getting ingrained as someone in the team who's in those meetings, and I'm not talking about sitting in a weekly team meeting taking meeting or taking notes. I'm talking about sitting in that meeting as a member of the team. That has really changed. That's something that I started doing years ago and completely changed how I'm able to do my role and the value that I'm able to bring, not only to my executive, but to his direct reports and to his entire team.

Jeremy · 18:27

Well said. I think that part of that has to do with the HR org chart and the levels and the titles aligning well with, instead of just saying, everyone has 12 levels and everyone has salary bands, and you've got senior assistant, and then you've got director, and you've got senior director, then you got vice president and senior vice president, and you're working your way up this thing. All the departments have that, but then you throw in the assistant on the org chart, and they're just off in the ether, and they're just like, okay, well, this is whatever, and you're just the assistant. I think having that structure and fighting for that structure for the assistants really will help even just the organization overall to just practically see on the org chart that you're part of the team instead of just this little bubble by itself.

Sarah · 19:25

Yeah, absolutely. We're partnered to be executive, we're part of the team, and I think for any assistant who wants to start doing that, but maybe doesn't know how to navigate the conversation with their executive, when you sit down and have this conversation that we just talked about, about their priorities, digging into their priorities and understanding where they're going, the natural ending to that conversation is, and I'm going to be in all of your leadership meetings. I'm going to be close to the priorities, I'm going to be close to what's happening in the business. As things change, we all know, and business priorities change and objectives change, you have to change course sometimes, but you don't know about that a lot of times, unless you're in those key strategic meetings. Get aligned with your executive and tell them that you're going to be a part of these meetings, you're part of the team, and you're going to be part of these discussions, and that will tremendously amplify your value.

Jeremy · 20:35

What have you experienced or have you experienced situations where the executive is like, well, okay, but you can't be in these meetings? Have you ever experienced that?

Sarah · 20:48

There are some meetings that maybe from an HR perspective, from a confidentiality perspective, it doesn't make sense for me to be in there or the subject that's being discussed, maybe it's a 10-year-off thing and it's pretty confidential at this point, so it doesn't make sense for me to be in there. That's fine. My executive and I, we've had an open conversation and he'll let me know, this meeting, it doesn't make sense for you to be in for x, y, z reason, but you're in these next four and that's fine. Because I understand that if I'm not able to join a meeting, it's for a very specific business reason and we have that open dialogue and that open conversation that we're able to talk about it openly.

Jeremy · 21:39

Awesome. Great. Well, what's kind of the ongoing, you know, so you've had that conversation, you've established, okay, I'm going to be in the meetings, I'm part of the team, you know, my goals are your goals. What is the like ongoing investing in the relationship, investing in the partnership, keeping it going? What's what's kind of the process for that? And do you have any tips to share in that regard?

Sarah · 22:15

Yeah, absolutely. It is an ongoing thing for sure. And one thing that I like to talk about a lot, and I talk about this in my course as well, is the power of the reset. A lot of times we will, it's easy for us to just kind of get stuck in a rut. Maybe you were joining some meetings and then you felt like you were a little bit too busy to join them. And so you need to kind of get back into them. Or maybe your executive has stopped sharing your, or maybe your executive has stopped sharing their priorities or has started keeping you out of the loop simply because they just are forgetting to tell you things. Sometimes that stuff happens. We get busy. We get caught up in our own stuff. And in those situations, you just hit reset. You call for a reset conversation with your executive. Maybe you go back to this foundational conversation about looking at their priorities, looking at their KPIs. Or maybe you need to reset another aspect of your partnership, your communication, a task. Maybe a task has grown inefficient and needs to be reset. Call for those reset conversations with your executive. And it's a good thing. So anytime you call for a reset, your executive should know, all right, we're getting back on track. Good stuff is going to come out of this conversation. And we are going to course correct and head in the right direction. So that's my suggestion. As time goes on, identify when things maybe aren't working or have stopped working or need to be reevaluated, stop and reset.

Jeremy · 23:56

Nice. Great tip. Love it. So, okay, before we jump into a little bit of kind of why you started Hey, EA, what's kind of the last thing you want to say to assistants in regards to maximizing their executive strategic partnership?

Sarah · 24:17

The one thing that I will leave them with is a little nugget from the executive's perspective. Executives, they do feel the pain of not having a strategic partnership, but they don't know that that's what they're feeling. For an assistant, we know when we're not operating in a strategic partnership, right? We start asking those questions, like all of the questions that you get from your community, Jeremy, how can I get my executive to give me more work? How can I be a better assistant? That's how we feel the pain of not having a strategic partnership. But executives, they actually feel it too. They just don't realize what it is. They think it's just the pressure of the job. And when you reach a certain level of success in corporate America, in your career, you kind of think that just being a stress to the max frazzled mess, that's how I'm supposed to be. I'm a vice president. I'm a president. I'm a CEO, whatever it is. I'm just supposed to be stressed to the max all the time. But what if it didn't have to be that way? What if after working with your executive to create that strategic partnership, they could come to you and say, I actually like my job again. I actually have a better relationship with my family because I can be more present. I actually feel like hitting our targets is attainable. And that's exactly what I'm seeing happen. And that's the feedback that I've been getting from the teams that I've been working with. And Jeremy, who doesn't want that, right?

Jeremy · 26:02

Right. Yeah, that's great. Awesome. Well, Sarah, thanks so much for being on the show. Tell us a little bit about why you started Hey, EA and what it is and where people can learn more.

Sarah · 26:16

Absolutely. So I started Hey, EA because I was really looking for resources as an assistant. And so I created Hey, EA in order to help assistants love their jobs again and also to help executives find more fulfillment in their role, too. It's amazing how we can really, truly help each other. And that's really why I created Hey, EA. So for anybody who might want to kickstart their partnership, they want to have a conversation with their executive and really start driving the strategic partnership, I created a free communication guide that is on my website, which is heyea.com. And that guide is going to be a great starting point for anybody. So you can go to my website, heyea.com, and download that free guide. Also, you can sign up for my free weekly newsletter. I just drop into your inbox once a week with a super short, super quick email that I hope gives you a ton of helpful resources and value. And then second, I'm offering my course, The Profit Center Partnership, which again, you can find on my website. And just for your listeners, Jeremy, I want to thank you so much for having me on. So for your listeners, I'm offering a 10% off code for my courses. So they can just enter Jeremy10 at checkout and get 10% off of the courses. So anybody who might be interested in that. And also I'm on LinkedIn. So come connect with me on LinkedIn, just Sarah Calderon on LinkedIn.

Jeremy · 28:06

We'll all put all those links in the show notes at leaderassistant.com/266 so people can find everything easily and reach out and say hi. You know, best of luck to you in your career and your baby and all that, all the good stuff. And yeah, thanks again for being on the show. It's been great chatting with you about a strategic partnership between an executive and their assistant. And I know that it's a topic we could talk about for a long time. And we will talk about it again and again on this podcast as it's important. And I think your nuggets of wisdom were great and helpful. And I'm excited for everyone to listen and reach out and say hi.

Sarah · 28:48

Thank you so much for having me. It's an honor to be on your podcast, Jeremy. Thank you.

Speaker 3 · 29:02

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