#381: Ashley Langlais on Supporting the Goals of Your CEO

In this episode of The Leader Assistant Podcast, Ashley Langlais, Chief of Staff at DVx Ventures, shares her unique approach to being a strategic partner to a CEO. Ashley details her journey in supporting her CEO through a "big first," such as writing his first book, making his goal her own from day one. 

Jeremy and Ashley chat about how to provide support beyond calendar management for major initiatives like book writing, speechwriting, keynote prep, and internal/external messaging. 

Ashley also covers the Chief of Staff role as a true strategic partner and shares valuable lessons learned for next time.

Show notes -> leaderassistant.com/381

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Transcript

EPISODE TRANSCRIPT

Hey friends, welcome to the Leader Assistant Podcast. It's your host, Jeremy Burrows, and this is episode 381. You can check out the show notes for this conversation at leaderassistant.com/381. Today, I am really excited to be speaking with Ashley Langlais. Ashley Langlais is chief of staff at DVX Ventures.

00:00:46  
And we've got a fun conversation in store for you. So first off, welcome to the show, Ashley.

00:00:53  
Thank you. Thanks for having me.

00:00:56  
What part of the world are you in and what do you like to do when you're not working?

00:01:00  
I am right outside of Boston.

00:01:04  
And when I'm not working, I have a four-year-old son named Remy. And so I feel like I'm still, like, maybe still considered a new mom. So I think, like, just doing things with him, like playgrounds and aquariums and zoos, I feel like my whole spare time is focused on that. So it's been fun.

00:01:28  
Awesome. That's great. You said four? Yeah.

00:01:32  
He's four, yeah.

00:01:33  
Four, wow. That's a fun age. Mine are 12 and 14 now, so it's been a while.

00:01:39  
Oh, yeah. So, yeah, yeah, yeah. Do you have boys?

00:01:42  
Yes, yes.

00:01:43  
Yeah, so, yeah. So, you know the physical nature.

00:01:49  
Oh, yes.

00:01:50  
And the high energy that you deal with. Yep.

00:01:55  
Love it. Well, tell us a little bit about your career. What, how did you get started in the support roles? Did you, were you an assistant before you were, you were a chief of staff and tell us a little bit about your career journey.

00:02:10  
Um, so out of college I had a few like admin roles in various industries. Like I was in media right outside of college and I worked in a hospital for a few years. Um,

00:02:24  
But I'd say I was an admin assistant at Cambridge Associates, which is a investment consulting firm.

00:02:35  
And I think there's where I really like found my career.

00:02:40  
So I was an admin assistant there, supported like eight executives across like three teams. It was kind of crazy. And I felt like

00:02:50  
Yeah, and I felt like I couldn't make an impact on the executives themselves. And that's the part of the job that I really liked. And surprisingly, I didn't even know that an executive assistant role existed. But because that was the part of the job that I liked, I was doing some research, speaking to recruiters, and I found the executive assistant role. And I was like, that's exactly the role that I want.

00:03:16  
So after Cambridge, I worked at GH Smart, which is a boutique consulting firm. They consult on human capital. I don't know if you've ever come across like the who method for hiring in your... I don't know. Maybe if you kind of give me the short summary, it'll... It's just like, it's like an approach to hiring, you know, just like one of the approaches that like, you know, people in that space use.

00:03:46  
Um, and side note, their book, Jeff's Martin Randy streets book, who is very good, highly recommend.

00:03:55  
Um, and that like explains the method, but anyway, so they created that method and they're just, I loved my time there. I supported two principals, loved them, loved the EA team. It was remote before COVID. So their model is like freedom and flexibility. And,

00:04:16  
I just, they were just, like, such forward thinkers. Love them. Anyways.

00:04:20  
I was there for about four years, and then an EA that I worked with previously, we reconnected, and she said, oh, I heard of this really cool executive that's looking for an assistant. And I was like, well, I'm not really looking for a job, you know, whatever. And she was like, I would really encourage you to have a conversation with him. So I looked at his profile, and I'm like, okay, the former president of Tesla, the former COO of Lyft. I was like...

00:04:50  
if he, if this wants to have a conversation with me, then sure. I'll have a conversation with him. Um, so I did. And that's like where it all started during the interview. My CEO now is like, you know, I'm on this board. I'm an advisory partner over here. You know, I'm doing this project. Oh, and I'm starting a venture studio. And I just couldn't like, I was just like, I couldn't not take this opportunity to like,

00:05:19  
do all these exciting things with him. So it's been six years now at DBX. Um, we built it to like, we've launched 12 companies. We have about like a hundred employees across the portfolio. Um, so yeah, it's been, it's been kind of like a wild ride.

00:05:36  
Wow. That's awesome.

00:05:37  
Yeah.

00:05:39  
So was the, when you first started working with the current executive, was the title executive assistant and then it morphed to chief staff or did it start with chief of staff?

00:05:49  
Correct. No, it was executive assistant, um, sort of like, like manager of the CEO office, basically. Um, so yeah, when I started, I supported him and then the other founders. Um, so it started as three founders and then we hired another, we took on another partner. So we had four, um, and I was primarily supporting the CEO and then just like other, you know, like

00:06:17  
lightly supporting the others, I'd say, until it got, like, a little heavy, and I recommended hiring another executive assistant to take on two of the partners.

00:06:28  
So that's kind of where we're at now. The chief of staff role happened because I think it was about two years into it, I sort of just, like, asked to...

00:06:44  
Really like changed my title. The the the reason was I felt like it was branding for me um

00:06:52  
like I needed the brand, as awful as it sounds, like for external people and also like inside because I was doing so many different things. Like I was sending out, you know, offer letters to people and like salary changes to people or, you know, telling the CEOs of our portfolio companies like, we need this, this, and this from you. And I just felt like, so internally I needed that branding. And then externally, like I was speaking to like lawyers and tax consultants and, um, you know, all of those external resources, I felt like I just, I needed that branding in order to, I don't know, not taken seriously, but just like, so they understood why they are on the phone with me, if that makes sense.

00:07:44  
No, that makes total sense. And I like that you, you know, you were able to present that business case and that your executive was supportive of it too.

00:07:53  
Yeah, absolutely. You know, like I think, you know, I was like doing the role without the title. And so I was like, I need the title in order to like bring it all together.

00:08:04  
Awesome. Awesome.

00:08:05  
Yeah. Yeah.

00:08:06  
Well, that's super great. It sounds like a fun, adventurous career. Thanks for sharing. And, you know, today I would really like to dive into really a overall concept of supporting the goals of your CEO, supporting the goals of your executive team. But specifically, you know, you reached out and we connected because your support of your CEO kind of went to a specific project of publishing a book, publishing and writing. Your CEO wrote his first book, right? Yeah. Yeah.

00:08:46  
You were very, very involved in that. And so I want to kind of walk through that journey. And if you're listening and you're like, my executive would never write a book. If they did, no one would want to read it.

00:09:00  
That's okay. There's probably other goals that your executive has that you can own as your own goals and you can help them execute and reach those goals. So even if it's not specifically a book, I think this is going to be a helpful conversation, but I'm also excited to chat with you, Ashley, because I've helped my former executive. I helped publish books and, you know, it's kind of part of that whole process. And then my current executive has tons of ideas, but one of those is also publishing a book. So,

00:09:36  
This is very relevant to me and my assistant role. And again, if assistants listening, if you're executives, maybe not writing a book, there's probably some big project that they want to do that you can learn a lot about in this conversation. So let's start with what was it like supporting your CEO through writing his first book?

00:09:58  
It was not what I expected it to be. I know you're not a stranger to this process and that world, so you'll be familiar with everything that I say, but I just felt like it was going to be a lot more straightforward.

00:10:18  
easier. I wasn't ready for how complex the publishing world is. And not just that there's so many different avenues in which to publish a book nowadays, but also there's so many different players.

00:10:37  
You need the editor and the agent and the ghostwriter and the publicist. And it was just like so many different players. So I think navigating the industry was the first step and also like one of the most challenging parts of the process.

00:10:56  
Gotcha. Gotcha. So let's actually, I'm curious. So when did the, when did the idea first hit your desk? Like when was it like, Hey, you know, I'm going to write a book and by the way, you're going to help me.

00:11:09  
Yeah. So we were in our annual partnership review. That's what I call my annual reviews. Because I think it's helpful to position it that way so that you can get as much information from your executive in terms of goals and priorities for the year. So we were talking about goals. And he said, this year, my goal is to write a book. And at that point, it became my goal for the year. And so I was like, all right, let's do this.

00:11:41  
So that's when it happened. I think, like I said, it was challenging because neither of us are from the publishing world, and we don't have direct contacts in that world, but he has a huge network, and I feel like I have a decent network in my own right, and so I thought between the two of us, I would connect with somebody and they would be like, oh sure, here's my agent or here's my editor. And it's done. But it didn't happen that way. And so I had to do a lot of research and speak to a lot of different people in the space and near the space in order to really understand that world and to really find the right team for us.

00:12:31  
yeah what was the like the the publishing side so with my executive my former executive you know he had i think when i started working with him he had already published a book that had done pretty decent so he was talking to publishers but then for me personally with my book the leader assistant

00:12:56  
I was I had not published anything. I was kind of getting going and I had done a bunch of research and I had a friend that had done self publishing with a publishing partner that kind of helps you through the process, but doesn't actually own the rights to the book or distribute it necessarily. They just kind of help you get through the self publishing process. So how did you guys determine whether or not you would self publish or traditional publish?

00:13:25  
Yeah, so great question.

00:13:29  
Again, I didn't know that there were different approaches to publishing. I thought traditional was the way to go.

00:13:36  
That's where I sort of started. So like our initial approach was like my CEO is a fantastic writer, but you know, he has a day job and he doesn't necessarily have all this time and just a hundred percent focus to the book. So like we, we were like, we need a ghost writer or coauthor, someone to help him write the book. So our approach was to find a coauthor that came with relationships and knowledge of the process.

00:14:02  
Right? That was difficult to find.

00:14:07  
Because, and I talked to many and first of all, they're hard to find because they're ghostwriters, right? Like, um, but I did speak to some and some, you know, were either in between projects or just weren't a great fit for my CEO or, um, one of them that I talked to was like, his platform's not big enough. And, you know, he's, he's going up against Michelle Obama's book. Like, you know, build the, build the platform and then come back. And I'm like, wait a minute, like he has to be a celebrity or like a former first lady to write a book, like what?

00:14:48  
So I don't know. So that avenue just, I felt like wasn't working. So that is when I did some research into things like hybrid publishing and self-publishing.

00:14:59  
But my CEO really wanted to make sure that the traditional route with a top publisher, with a healthy advance was off the table before we did something else, at least for his first book.

00:15:14  
you know? Um, so how I, so how I ended up finding somebody, do you want to hear?

00:15:23  
So he had sent me this article that I think he read from like the information. Um, and the article was something like, here are the ghostwriters behind bestsellers and it featured five. And so I, and their contact information was like listed or their website or So I reached out to two of them that had the most bestsellers among the five and had a business book in their library.

00:15:51  
And one of them, the one that responded, her name is Carly Adler. She coauthored Mark Benioff's book, Behind the Clouds, I think it is, and Maynard Webb's book. And I'm like, there's no way that these people are going to respond to me.

00:16:08  
Not to me, to John, because I reached out as my CEO with the pitch. But she did, and she was all about the idea and was very welcoming to have a call with me.

00:16:25  
Um, but she was working on another project and we kind of went back and forth for a few months. And then she finally, she was, she was finally like, I'm not available, but I believe in the book. And so introduced us to our now agent.

00:16:40  
Gotcha. Gotcha.

00:16:41  
So like the initial approach ended up working. It just took a few repetitions.

00:16:48  
Right. Yeah. And it's not like you had like a.

00:16:52  
It was a little bit of a roundabout way, right? Like it wasn't like, oh, you know, go here, do this, do this.

00:16:57  
It just kind of had to... Totally roundabout. And also like, don't be afraid to cold call because you never know who's going to pick up the phone. Like I kind of can't believe that she did.

00:17:08  
Nice. So, OK, so you got that you you worked with an agent.

00:17:14  
Did you then start writing or did you try to get the agreement with the publisher first? Like, how did that happen? Like, was it even a was it even a like, did the agent think, oh, we can get a deal? Or was this kind of like, well, we'll see. And you know what I mean? Like before you, I guess before you moved forward with the project, you had to figure out is it going to end up a traditional project?

00:17:43  
Yeah. Yeah, totally. And so like a book proposal is something that you need. So like, I think, I think the way, like the process is to get the agent, then you write the proposal and you shop that around to the publishers. Um, but because we were looking while I was looking into other avenues, like hybrid publishing or something like that, like,

00:18:06  
within those few months, like we pretty much had wrote the proposal because we had, we like wrote the pitch to sort of get people interested. And then, you know, I added all of the things that you need in a proposal, like how big my CEO's platform is and all of like the media appearances he's edited, whatever. So once we got the agent, we pretty much did have that proposal. The agent was pretty, he was like pretty certain that, um, it would get, it would get a deal.

00:18:38  
Um, yeah, I don't, I don't know if that's, if that's, you know, a different experience than, than you had, but yeah, he was pretty, he was pretty certain. I don't know if he only takes on books that he's certain about or what, but.

00:18:51  
Right. Okay.

00:18:52  
Yeah.

00:18:53  
So then you, you were like, all right, we're going to do this. So then you started submitting the proposal to different, different publishers.

00:19:00  
Yeah, so yeah, so the agent, okay, so as I said, like there's many different players. The agent I found is like, that's the person that does connect you to the publisher to get the deal. But they're also, and I don't know if this is true of all agents, but this one in particular was like,

00:19:21  
the one that guided us through the process, like anytime we had questions or wanted recommendations or wanted guidance, like that was the one that we went to. It seemed like he, like the agents kind of like looking out for the author. I don't, I don't know if that's like everybody's experience, but ours was really good in that sort of way. So yeah. So he connected us to the publishers and, um, and we got a few offers and then, you know,

00:19:52  
took one of them.

00:19:53  
So that's great.

00:19:54  
Yeah. Yeah.

00:19:56  
What would you say? So if there is assistance, you know, listening that are like, Hey, my executive wants to write a book as well, their audience, they're thinking, okay, their audience is the size or their, their reach is this far.

00:20:12  
Is there, are there kind of some ballpark numbers or ballpark, um, you know, goals for an executive's reach that that those listening could maybe help their executives aspire to to try and

00:20:27  
you know, get to the level, I guess, if you will, of where a publisher would actually consider it? Or does your experience, was there any sort of like, hey, if you have, you know, an email list of 30,000 or if you have a LinkedIn following of 50,000, are there any sort of benchmarks that you saw during that process that were like, oh, this would help?

00:20:48  
I mean, that's what, when I was talking to that ghostwriter, like, that's what she was saying, that you need, like, a newsletter of, like, thousands and you know 50 000 linkedin and twitter following um when once got like but carly didn't think that um the one that ended up like connecting us with the agent she didn't

00:21:12  
She was like, I'm actually surprised that you got that feedback. I think the contents of the book is pretty interesting in its own right. Your CEO does have a decent following. It's not mind blowing, but he's on CNBC regularly as a commentator. He is out there.

00:21:36  
I will say, though, we did take some time. So we hired a comms team. We have, like, a contractor comms team that worked to build my CEO's brand even before, like, the book. So, yeah, so they did, like, increase his followers on, like, LinkedIn. But, you know, it's, like, 15,000. It's not, like, 50. And they did, like, increase his...

00:22:06  
like his media hits and his appearances in media, like thought leadership, um, op-eds and stuff like they, they helped with that. So they did like boost his brand a little bit. And I do think that that probably is helpful.

00:22:22  
Um, you know, if your executive is going to write a book one day.

00:22:27  
Gotcha.

00:22:28  
Awesome. Super helpful. Um,

00:22:32  
Let's dive into the writing process. So how did you specifically support the writing process?

00:22:39  
So this was interesting too. I think like, so there are a lot of challenges to this project, um, navigating the industry, one of them, but like the second one, and I think this always comes up in our types of roles, but it was like not really knowing my role or how I can support. Cause I'm like the first time support to our first time author. Like, you know, I don't know what the process looks like and I don't know where I can be helpful yet. Um, but yeah,

00:23:09  
Go back just a little bit, even before the book came about. So my CEO was speaking at the World Business Forum, a couple of those around the world, and he was writing a speech for it.

00:23:23  
And I felt like this was an area that I could totally help him with, but I'm not quite sure how to write a speech for him. Like, you know what I mean?

00:23:34  
So I asked one of my mentors and I was like, you know, do you have any advice? Like, I really feel like this is a place where I can add value, but I'm not quite sure how to go about it.

00:23:43  
I'm not quite sure how to go about it. And she was like, well, you could offer to be like a blank page because that's always the tough part of the writing process is kind of like, where do I start? So have like a session with him, do a brain dump. You collect the notes, organize them in a way that makes sense.

00:24:03  
and highlight areas that resonate with you and then build off that. So that's what I offered to my CEO. And my CEO is very self-sufficient.

00:24:14  
I was surprised that he took me up on my offer. Like, he would never ask me to help him with that. Like, he doesn't know. I don't think he knows that I could be helpful in that type of a scenario, right? So he said yes, and so I was thrilled. I got, like, my foot in the door to help him with something else, expand my role. And...

00:24:36  
And so, but he are, so he sent me what he had and he pretty much already had the outline. Like what he needed was kind of like to fill in the gaps with like stories that sort of like illustrate the points that he's making in the speech, if that makes sense.

00:24:53  
And so those, so, so we had like a, a riff session on that. I've, I watched like all the podcasts, all of the YouTube videos that are out there on them. I took like eight, Any kind of like notes that I felt like in meetings could be an example of something we could like elaborate on for this speech.

00:25:13  
Um, I like collected all of these examples and then during the riff sesh we like talked about them and just built the content that way or finalized it really So I was already familiar. So the book is is based on that content So it's already familiar with the content and already kind of like involved in that part of the process um but

00:25:37  
once we got the book deal with the agent also the agent found us a co a co-author so like that's also a role of an agent also so all right so now my ceo has the co-author he doesn't really need me to help him with like the writing sessions and everything so like how can i be helpful through this the writing process and so again wasn't quite sure like what my role looked like in this phase so I just joined everything I could to start so I could figure out like, okay, where are areas where I can be most helpful? So I started like in the writing sessions with my CEO and his co-author. And I was like, I don't need to be in these writing sessions. You know, like the co-authors got it. Like he's good at, you know, his job. He knows what he's doing. But like I can help behind the scenes managing the workflow. Like I want to review all the drafts that come through to make sure, you know,

00:26:32  
you know, um, all the points that my CEO wanted to make are made, or if I have any thoughts of what we could add, um, to like, it get even like more of a robust example or, or something like that. Like I stayed in the, um, I stayed involved just more of like a behind the scenes role.

00:26:55  
Gotcha. Yeah. Nice.

00:26:58  
So did it conflict or I guess one thing I'm thinking through is, you know, you mentioned, you know, your CEO has a day job and you obviously have a day job. So like, how was this just something that...

00:27:15  
you slotted in, right? Like solid in times or, you know, how did that conflict with at times, you know, did you feel like it was, it was pulling you away sometimes from your day job, if you will?

00:27:30  
Yeah, it was, it's, and even now, because it just, the book just launched on March 24th. So there's still some like,

00:27:39  
There's still a lot of promotion going on now.

00:27:42  
I felt like throughout this process, this was probably like a two year process from when my CEO said he wanted to write the book to when it got published, exactly two years. And so it definitely was like periods of heaviness and then periods of not so heaviness. So like during the actual writing of the book,

00:28:07  
it was like more manageable, you know? Um, but I would say like the heaviest part was, um, launch, like promoting for the book. So like pre-launch was the heaviest part because there's just so many, um,

00:28:25  
like interviews and appearances and travel and everything that, um, my CEO needed to do so that it could all come out around like launch time, you know? And, you know, like I said, like we're doing, we have investor meetings as you know, same with you. Uh, we have investor meetings and we have like, um,

00:28:47  
he has a bunch of speaking events and we have like internal ops reviews and I see meetings. And so it was, it was a challenging time because there was so many competing priorities for my CEO's time. Um, and I would say like still now I'm not out of it yet, but, um, yeah, but I think just always going back to like prioritizing, you know, it's like,

00:29:13  
how does this fit in, in the list of priority? And if it's not on the list of priority, it doesn't fit in, you know, I also think there's something to note too, where, um, well, two things really like during this time, I think to keep in mind that, you know, you're not just managing your executive's calendar, but it's also like you're managing their energy because they're not just doing, um,

00:29:41  
Even if it's not just travel, but it's like how many pitches can he do in one day? Not just book pitches or promotion, but also like the investor pitches or a speaking event or even like a, you know, a pre-call to a speaking event so that like he's, you know, he's brainstorming and having these thoughts. Like how many output, high output meetings can you stack on in one day? Like definitely needed to be more mindful of that than like, you know.

00:30:11  
any other time, I guess. And then also,

00:30:15  
like there was some times where my ceo was feeling like a little burnt out and would be like let's push that podcast off until post launch and i would push back and be like here are the metrics here's the recommendation from the publicist like you know how many books are you going to publish in a year this one moves the needle like i'll try to make your travel as comfortable as possible I'll stack on other meetings to make your time as efficient as possible. But I really think you should reconsider doing this podcast, you know? So there is like some, some sort of like managing that too, you know?

00:30:55  
Yeah, totally.

00:30:58  
Awesome. Well, what would you say this experience did to change, you know, changed how you thought about or, you know, how you work in your role?

00:31:09  
What was the biggest difference or, yeah, what did this experience do to how you view your role?

00:31:17  
I think that it's... It made me reflect on the role itself, and it's kind of like the role is not clearly defined.

00:31:32  
And I think that's part of it. That's like the challenge of the role is that it's not clearly defined, but it's also kind of the beauty of the role because.

00:31:40  
you can make it as involved, as strategic, as like impactful as you want. Um, and, and, and that you're like, your executive gives you the room to operate in.

00:31:54  
Um, and I think like that's, it's, it's exciting, you know? Yeah.

00:31:59  
I love that.

00:32:03  
Well, what to kind of close the loop and thanks for sharing that journey. I know it's, I'm sitting here, my wheels are spinning because I'm thinking, all right, what am I going to, what parts of this process am I going to have to hit you up for help on for my executive?

00:32:20  
I can only share my experience, which I know, like, I don't, I don't know if it's like, you know, a cookie cutter experience across the board. So, but I'm happy to share and help how I can. Yeah.

00:32:31  
Awesome. But to wrap it up, I would love to hear kind of

00:32:36  
the high level from your experience, what do you feel makes you effective in the role of chief of staff? And maybe even just a tidbit for those listening who are currently in the assistant role, or maybe they're in the chief of staff role with the assistant title. Yeah. Yeah. What would you say is, yeah. What's made you effective in that role?

00:33:01  
I think like, yeah,

00:33:05  
For me, the role was earned by like creating value. And the best way that I was able to create value was through access. And so I think like...

00:33:20  
that's kind of like first and foremost is to like gain that access. So like asked to be in meetings, asked to be looped into conversations, asked to be part of a project that might not be in your wheelhouse because like you're going to gain context and business knowledge and you're going to be able to create value with that knowledge, you know, like, um,

00:33:45  
Knowledge is power. That's always what I think. But the way that I ask for that access is not like, hey, do you think I should join the board meeting? It's, would you mind if I join the board meeting so I can take notes, track action items, and gain context?

00:34:03  
And if you position it that way, I've never been told no. And then when you start adding value...

00:34:11  
based on like the information that you're getting from those meetings. And you don't even have to ask to be in them anymore because like you're expected to be in them.

00:34:21  
That's well said. That's awesome.

00:34:24  
Thank you so much, Ashley, for your time and keep up the great work and your support for your CEO and your team. And what's the best place for people to reach out if they want to just connect and say hi?

00:34:39  
LinkedIn probably is the best place. Yeah. Yeah.

00:34:43  
Great. Well, I'll put your LinkedIn link in the show notes at leaderassistant.com/381.

00:34:56  
And check out all the links in the bio and all that fun stuff in the show notes. So thanks again, Ashley. Really appreciate your time. Thank you, everyone, for listening. Keep up the good work and we'll talk soon.