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[upbeat music] Hey friend, it's David Nebinsky, the community lead here at the Chief of Staff Network.

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We help chiefs of staff through the three Cs: cohorts, curriculum, and community via Slack with over 900 people in it. You can learn more about our membership, events, and courses at chiefofstaff.network.

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This episode was recorded at our Chief of Staff San Francisco Connect Conference. We were at such a beautiful venue that we decided to record the episode outside.

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As such, there's a little bit of wind, so the audio is not as clean as prior episodes. Thanks for understanding, and hopefully it makes you feel like you're going along for a walk with us.

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As a reminder, we have two more Connect Conferences this year, with one in New York in October and in London in November. Hope to see you there. This episode is with Ada Madigan, the chief of staff at Trust & Will.

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In this episode, you'll learn about how her role has evolved, how it initially started as an associate chief of staff, how the company is hiring an EA now, and so much more.

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So excited for you to level up as a chief of staff. Here we go with Ada. Okay. Uh, Ada, welcome to the podcast. Thank you. Nice to meet you, David. [laughs] We've emailed a bunch over the years. Oh, yeah.

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No, you're in m- you're in my life, but I've never met you. You know? [laughs] Like, you're a figure.

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I have to tell you this, um, yesterday I was doing a little recon on a product that we're cont- considering introducing- Yeah...

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to our company, and it's gonna be a big shift if we do make this decision, so I'm doing some, I mean, like, full due diligence- Yeah... on the decision.

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And, um, I was just looking at other companies that are using it, and, you know, copy-pasting to see who they are, what kind of companies they're running. Yeah.

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The very first person I copy and paste into my Google, the first picture that comes up is you with this person. Wait, what? I know. [laughs] Isn't that funny? I was like, weird.

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Like, that is so weird because we're sitting down to do this today. Yeah. I'll... Later on I'll grab the name and I'll share it with you. Yeah. I mean, it's either... It has to be you. Like, I know it is.

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[laughs] Or it's a really solid doppelganger, which is, like, another conversation to, like, have. [laughs] Yeah. Wait. Okay. I guess- Yeah. I- I'm, I'm glad we're having this. I don't know... I need to know more. Yeah.

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I know. [laughs] But I'm like, wait, people are here to listen to this chief of staff content- Yeah. [laughs]... not to know, like, David's random life stories- Yeah...

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and- As soon as we turn off these mics, I will go find that name for you- [laughs]... so you can bridge the gap. Yeah. Okay. [laughs] Cool. Um, so all right.

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So Chief of Staff Podcast, um, how would you say you got your current chief of staff role? I just had a little background in operations.

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I actually, after I exited college, um, when I graduated, I started my, you know, career in publishing oddly enough. Um, did that for probably five, six years.

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Did a little dance into some operations for a charter network for s- um, education. And then that operations background gave me enough to cold apply to this job that I have now.

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I had just moved to San Diego and, um, saw this company. You know, it's a San Diego-based company, and they had an opening, and I was like, "I could do that," and cold applied, and here I am three years later. Wow. Yeah.

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Like, uh, like saw the o- like saw the l- uh, job listing online and then applied online. Did you send any, like, DM, email, or anything like that? Um, I didn't. So reached out to... I'm trying to remember, actually.

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Applied, sent a email, I think, to their head of people. Okay. Missy, who's, like, one of my ma- like, just could not live without her now, which is so funny to think about.

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But yeah, sent, sent an email to her, I believe. And then, um, the only connection that I had was my sister-in-law, um, went to the same university as our founder, Cody. Yeah.

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And so she sent him a little nudge that said, "Just would vouch for this person," and yeah. So that was, that was probably helpful. [laughs] Yeah, yeah. Yeah. Got you in the door a little bit. Yeah. Um, okay.

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And then when you joined, what were you focused on then, and what are you focused on now? So I had...

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It was a unique opportunity in the sense that I joined as an associate chief of staff, which I don't think is a very common, uh, opportunity that that comes up. Um, and so I came into the role with a lot of...

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It was EA-heavy, for sure. Mm-hmm. But, like, that first phase was learning from the chief of staff who was in the role already. Okay. Um, she was gonna be eventually shifting out and, um, so it was like, you know,

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me there with the training wheels. Yeah. A lot of EA-heavy stuff, but also still getting a lot of face time with our board, our investors.

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You know, my ch- my, uh, CEO kinda just, like, took me, you know, arm in arm, took me along with him, um, and just started learning the full context of the company and understanding, you know, where we, where we started, where we are, what our ideas were for the future.

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Um, and then about a year and a half into my associate chief of staff role, stepped into the full chief of staff role. Okay. And did that other person leave, and then that's how you moved up, or?

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She transitioned to a head of operations role. Okay. Yeah. Yeah. Okay. And then, uh, I love that... So it was associate chief of staff? Associate chief of staff. Okay. Yeah.

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So it was perfect 'cause, like, I was getting to learn from her, like how she facilitated exec conversations, how she thought about strategy, how she, you know, managed the relationships.

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I, like, got to see her hard at work for a year and a half, um, with her as, like, support, air coverage, but also, like, still getting opportunities to get my hands dirty.

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Um, so it was, like, truly, like, an ideal scenario for someone new to the role. Yeah. Yeah. Yeah, I've seen, like, deputy chief of staff. Associate chief of staff I haven't seen as much. Um- Yeah.

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[laughs] Maybe they made it up. [laughs] Yeah. [laughs] Or maybe after this podcast it, like, you know- Yeah. [laughs]... uh, becomes a lot more popular. Yeah. "You know what?

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I heard on this podcast associate chief of staff," and, uh- Yeah... they're like, "That's a new title. We're gonna start adopting that." Run with it. Yeah, yeah. Yeah, yeah.

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But still pay people like a normal chief of staff role. [laughs] Exactly, yeah. And it was, like, a lot of EA-heavy stuff. You know? It was like...

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I say this about my roles to this day, but, like, if it was on the CEO's mind, if it was on Cody's mind, it was on my mind.

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That still remains true, except I have, like, a full other bracket of work that works, like, is alongside that.

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But yeah, it's, um-It was EA heavy and s- to a degree still is, but that's why we posted a job opening for an EA yesterday. [chuckles] Okay. Oh, whoa. Okay. A lot has happened in the last 24 hours. [laughs] Yeah. Okay.

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[laughs] I'm like, wait, should we record another podcast tomorrow? [laughs] Maybe. Because in the last 24 hours- Part two. Yeah, yeah, yeah, exactly. Like, things...

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Uh, well, hey, things are moving in the chief of staff, uh- Yes... whenever, in the chief of staff role, so. Yeah. Um, okay. So then, wait, what do you... Did you advocate for this EA hire? Yeah. Yep, I did.

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Um, I think it's not lost on anybody that it's necessary at this point. Mm. I don't think that, like, you know, I, I don't mind that component of my job.

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It's just literally, um, c- like, a factor of being able to prioritize it to the degree that my principal deserves.

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Like, he deserves someone who can give their full attention to that, and I didn't feel like I could all the time, you know? And so, um, it feels like a very natural next phase for- Yeah...

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like, him too, as, like, as a, you know, high-growth startup CEO. Like, it's the next thing for him to have someone who can, like, really quarterback all those logistics for him. And which is beautiful.

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It sounds like that was... I don't know, was it a collaborative conversation of, like, "Hey," like- Mm-hmm...

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you know, "I'm continuing to level up," and, "Hey," also, like, "You're continuing to level up," and, like, "The company is continuing to level up" and like- Yeah. Yeah. Is that kinda how it went down? Exactly.

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And, like, I think, you know, it's been on our minds for a long time. Um, and it was just there are, like, I would much rather us hire a product person- Yeah... over, uh, an NEA that just takes work off my plate.

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Like, I would much rather prioritize a tech hire any day of the week. Hmm.

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But now we're in a position where it's like, you know, you can have an EA come in, and so there's, it's like there's a little bit of liberating feelings going on with that. Wait, wait.

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What did you mean by, like, the, like, you would ru- much rather have a product person, like- I want our, you know, I don't want our, I don't wanna... Like, me managing this component of the business

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is just extra work for me. It's just, like, a little extra time. Ah. You know? But, and I would rather, like, that head count, the money- Yeah... that goes towards that person,

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it's, I'd rather it go towards someone that's gonna drive our company forward from a product standpoint. I think that's where you should prioritize first and foremost generally. Yeah. Um, and so now it's not

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a having to choose between one or the other where we are right now. Love it. Love it. Okay. Um, and then, uh, what do you think that this will... Or I guess, like, yeah, what do you think this will free up for you?

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Or, like, maybe let's, like, kind of... You talked about this, like, other bracket of work. What's the other bracket of work? There's like, you know, this is a perfect example. Like, there...

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Last, um, couple weeks ago we were all together for the first time as, like, the company we are today in Scottsdale, Arizona.

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And that summit, you know, there was a lot of really amazing things that came out of it, and a lot of it is for me to carry forward afterwards.

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You know, we conducted this blockbuster workshop that, you know, is basically like, "Hey, there's 100 people in this room." There wasn't, there was 90. Yeah. Correcting myself. "There's 90 people in this room.

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Like, everyone sh- fire up a hand and tell us, like, what's wrong. Like, what's going on at the company that you're having a hard time with? Where are we dropping the ball? Where are you not happy?" And, like, not, like,

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you know, it was very, um, like, uh, like data. You know, someone threw their hands up and like- Yeah... "I want more," like, this data. Blah, blah, blah, blah, blah, about data. And it's like, okay, great. We got that.

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Let's, let's solution. Let's solution, do that.

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So what I have now are, is, is this huge stack of ideas to combat this problem, and, like, before I might not have felt like I could've given things like that the attention I want to, and I don't want our team to ever come to us and say, like, "Here are all these issues we're having," and then us not do anything with that.

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And so now I feel like I really do have the time to, or I, especially once this person's onboarded, like, to go and s- focus on that and get, get those things, um, like, get the plan to combat those things back to the team and say, "We heard you.

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Here's what we're doing. Um, here's what's happening now. Here's what's happening later."

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I just feel like I'll have more time to, like, get into the nitty-gritty of those things and do them well and not, you know, mad dash, trying to just get it done with all the other things as well.

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So just starting to focus. So sound- Yeah. So it sounds like your focus is, is becoming more and more around, like, building the product of the company. Like, the company is the product, so to speak.

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Not like- That's how... That would be my product, yeah. [laughs] Yeah. Yeah. Not at all a tech, um, leader at all, but yeah.

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I think, like, how our company functions, that's a great way to put it, and I feel like that is my product, yeah. What, uh, yeah, like, h- how do you, if that is the case, um, what does that, like...

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What kind of goals or KPIs do you have, or, like, what do, what are the kind of things that you're, like, thinking about driving or focusing on driving if, like, you

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were f- like, really thought about your work and role as, like, driving the product of the company- Yeah... like, and the product, the company being the product?

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I always, and this is m- me as a generally type A person, uh, I always want our OKR and strategic planning pro- I mean, we all- Yeah... it's what every chief of staff is, wants. We want that to be smooth and easy.

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It's never gonna be easy. It's always, like, super hard. But, like, from where we s- from when I started, uh, when I took over this process compared to where we are today is so much better, but I know

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I can get, I, and I know we can get even better with it, like, how we approach that quarter over quarter. Yeah. And actually, this is, uh, something that I, I have learned.

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I mean, I've, I've recognized it as a learning for myself in the last little bit is, like, I spent the last year, 'cause we, we reorganized, um, our executive team.

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We basically have, like, a new executive team, and-I spent the last year like focused on them kind of.

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Like, I kinda just had my head towards them, and when thinking about like the OKR planning process, I'm like, "Oh, it's time to like go a later- layer deeper with everybody, and like start connecting more directly with, um, the rest of the team on this."

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'Cause like,

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the, the ownership of it, like, to- for us to have all those things pen to paper, our OKRs for every quarter, like it is all of our responsibility on that team, but like ultimately if it's not done, I feel like it's my problem.

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Mm. Like it's my fault. And getting the buy-in of the rest of the team to make those things happen, and then them also be able to hold their execs accountable is like a huge, uh, a huge benefit.

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Like if I can get that team working with the executive team as like their accountability partner almost, then it makes my life a lot easier, too.

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And so I'm starting to penetrate oh- beyond the executive team on like that process. Mm. Feel like I lost your question, but [laughs] No, no, no, no, no.

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I think it's like what I'm hearing is around like you focus on like the first couple of people, like the first layer, but then like as you're building out this product- Yeah...

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the company being the product, you're now like finding the other influencers, stakeholders- Yes... et cetera. Like- Yeah... points of like where you can drive impact, change, et cetera. Yeah. Um- Yeah.

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So it seems like you're building out, like you had like an MVP- Mm-hmm... and now you're- Yeah. [laughs] That's it, actually... you're scaling. [laughs] Yeah. Yesterday recorded a like new Loom [laughs] Yeah...

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for the team to reference as we go into this process for Q3, and yeah, trying to just... It's been... That's... I mean, it- it's been iterated on so many different times, and it...

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I at first like was frustrated with myself that it wasn't perfect the first time around. Um, put a lot of pressure on myself, and then I'm like, "Oh, the iteration is just part of it.

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That's how it goes, and you just keep learning and, and implementing what you learned from the last session, and just keep doing it." Yeah. Yeah. Um,

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and has there been any other like major like evolutions or moments within like the three years or so? Yeah. I mean, my... So the three years, it's like there's all sorts of fuzzy transition periods.

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[laughs] Um, the first year was like that foundational understanding the company, like working styles, the people, et cetera.

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Second year, you know, it was tricky and hard to get us to where we are now, and now we're like in this mode of IPO readiness, and thinking about that, and looking like down the road and how we pull that off, and what we can be doing today to make sure- Yeah...

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like that we're in a good place for that to re- be a, you know, realistic outcome for us in the next few years. So. Love it. Yeah. That's an exciting part.

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I mean, I'm like, it's crazy to think, like the energy of the company has shifted- Mm... a lot, and I'm so grateful for it. Like, not to say that the energy of the company wasn't good before. It was great.

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They have such a strong culture. I love the momentum that I feel where we are now. Mm. And, um, the people around the table that are creating that momentum is, yeah, it's palatable. Hell yeah. Yeah.

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[laughs] So it was that first year that was like foundational, the second year, and then like now this third year feels like we're in a new like- Yeah... launch phase. Chugging. Yeah. Yeah. There's... Yeah.

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I was gonna try and make some silly analogy- [laughs]... about a train with a bunch of coal in its belly or something. [laughs] Yeah. Skip that. [laughs] Yeah. That's cool. Yeah. Try it again later.

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Um, is there anything you'd wanna share to, you know, other chiefs of staff or aspiring chiefs of staff? Oh, gosh, yeah. I mean, connecting with other chiefs of staff on your...

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is on a regular basis is the most valuable thing you can do for yourself. Mm. I... It is... Everyone knows this who is a chief of staff. People who aren't chiefs of staff might not know it.

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It is a very lonely island-of-one job sometimes. Um, and I also feel this thing of like, I don't really have a team. Like, my... The executive team is where I exist, but they have their teams that they're attending to.

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Mm. And having your team of chief of staffs that are there to jam through things with you, um, you know, validate each other, learn from, is

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like, I don't think there's anything more valuable that you can do for yourself than like connect with pe- other people in the role.

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Um, so yeah, that and being comfy with the iteration and, you know, understanding things are gonna shift, and you're gonna learn, and you're gonna implement those learnings, and you just ke- keep doing it over and over again.

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[laughs] Yeah. Yeah. So that's why I love the Chief of Staff Network. Oh. It's been like vital for me in that, you know. A lot of the people I talk to frequently are people I met through it, so. Amazing. Yeah.

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Love hearing that. Yeah. Um, anything else you wanna share? Anything about the company or anything else? I mean, yeah. We kinda didn't do an intro to the company, did we? [laughs] We just jumped in.

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[laughs] You can edit this back. You can pop this back in. Uh, Trust & Will is the leading digital estate planning platform. We are trusted by one million families and individuals.

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Just closed our Series C, which is a crazy thing to say. C. C. Yeah. Yeah. When I came on, I was... I helped, you know, get the Series B over the finish line. Um, and, you know, got...

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That was a perfect learning opportunity to prepare me for this last round, and it was a lot of fun. I, I love fundraising. And you worked on that stuff? Yeah. Yeah. I quarterbacked that internally, and I...

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It's, I don't know, kinda nerdy maybe that I love fundraising, but I do. [laughs] It's so fun. I remember once we were in an investor call, and someone was like, "What do you guys like about your jobs?"

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And I know I'm supposed to say, like, "I do love our mission," obviously. Yeah. Like, I love that, but I'm like, "I love the fundraising part." [laughs] I like getting...

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I like going out there and being like, "Here's what we're doing. Here's what we're gonna do with your- the money, and here"..., you know. Yeah. Getting that plan out there. Yeah.

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So I f- find that process very satisfying. Love it. Um, well, if people wanna find you, they can find you on LinkedIn. Yes. Um, and, uh, yeah, this has been so great. Yeah. I'm so glad we had this chat. I know.

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Seriously. I'm so glad to like meet you, mate. [laughs] Not just a bubble on Slack anymore. [laughs] Thank you so much.

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