Ellie Dunne, Executive Assistant to the Head of Global Security at Stripe, shares her tips and tricks for how to gather the context you need in order to confidently make decisions on your executive’s behalf and what that looks like in practice. Perhaps your executive never has the time to get you up to speed or lacks the communication style to provide you with the details... or maybe working from home has just made it all the more difficult to get your questions answered. Regardless, this is an important skill to have in your toolkit – something that takes time to master and something that Ellie knows how to do well!

There’s no denying the record of IPOs that have taken place on the US stock market this year and the flurry of organizations headed down that path next, so we decided it was time to dedicate an episode to the role an EA plays in taking a company public. We invited back former REACH guest Tanya Benvenuto, who played a significant role in Okta’s IPO back in 2017. At the center of it all, ringing the bell next to CEO, Todd McKinnon, Tanya lived and breathed this experience first-hand. In this episode, she shares what goes on behind the scenes, how best to support your executive through the process & how to navigate all of the additional intricacies and responsibilities that come with taking a company public all while maintaining the upmost level of discretion. So, if your organization has officially filed an S1, this episode promises to lend insight into the process and prepare you for that life-changing experience. 

We’ve talked a lot about what it means to support an executive in the business realm, but less has been explored about what it takes to support an executive in the personal realm. We decided it was time to dedicate an entire episode to estate management, so we invited prominent Estate Manager & Personal Assistant, Alicia Myers, to discuss all things estate management and how to successfully set up a personal household. We touch on how to create a household manual and implement a seasonal maintenance checklist, to how to coordinate a design & build project, to how to manage multiple estates and above all, what it takes to support individuals in the public eye who live highly complex, involved and demanding lives. Here’s a teaser for you: it requires resourcefulness, discretion, precision, attentiveness, flexibility and the need to check your personal values and opinions at the door. So, if you’re an Estate Manager looking for best practices from the best of the best or, perhaps, you’re currently a nanny or family assistant who’s curious about the estate management piece, or even an executive assistant interested in transferring to private service, this episode is for you!

Angela Wiley, Executive Assistant to the SVP of Americas Sales and the SVP of Global Corporate Sales at Equinix, talks about her experience supporting newly minted leaders and executives who had never experienced support until Angela! In this episode, we discuss the typical areas that first-time founders need coaching or direction from their EAs and specifically, how Angela built both a thoughtful and meaningful partnership with her former executive at Inkling. When supporting a new executive, your role takes on a different responsibility in that you become both an ally and a coach. As Angela puts it, supporting a fist-time founder is a tremendous opportunity to leave a legacy as an executive assistant for years to come. So, whether you’re supporting an executive who has never been an executive before or has never had an assistant before, Angela knows what it’s like to be in your shoes and is here to offer you advice and encouragement.

Shelley Trask, Senior Executive Assistant to the CTO/Co-Founder of Slack and avid thought leader in the administrative community, joins us to tackle one of her favorite topics: How to Support a Difficult Executive. (And in case you were concerned, no, she's definitely not referring to her current exec!) Listen in as Shelley shares her strategies for how to get around said difficulty and how you can help coach your executive’s behavior & influence their habits or even draw the line when a situation is simply incorrigible. Whether you’re dealing with the new exec, the too-busy exec, the non-responsive exec, the no-boundaries exec, the perpetually-late exec, or even the brilliant a**hole (as Shelley puts it,) we promise you’ll be taking notes throughout the entire episode & leave feeling equipped with practical knowledge you can begin implementing as soon as tomorrow!

If you’re looking for advice on all things salary negotiation, performance reviews and mentorship, you’ve stumbled upon the right episode. Mentorship is something Senior Business Partner, Autumn Heard, is incredibly passionate about. She currently manages a team of three admins at Medallia but has helped mentor, train and develop many administrative professionals over the years. In this episode, Autumn mentors our community by sharing her tips for things like how to prepare for a performance review, how to ask for feedback, how to provide support that aligns with your executive’s goals, how to negotiate the salary you want and deserve, and also what to look for in a mentor.

If you couldn’t join us for our first REACH Roundtable Livestream, we saved our audio playback for you. REACH Roundtable is an extension of our podcast where we invite former guests back to discuss all things hot topics in the Executive Assistant world. For our first Roundtable, we tackled the single-most relevant topic: “Returning to the Office.” In this episode, you’ll hear from the guests you know and love, Lauren Pelusi, Rowe Hoffer, LJ Cohen, and Kristin Beatham as they share their unique perspectives on whether EAs should be expected to return to the office alongside their executives and if not, how that forever changes the landscape of executive support. Join us for the next livestream and we'll address your questions in real-time. Plus you'll be able to enter our giveaways!

The Chief of Staff topic isn’t going anywhere! In this episode we interview Jenna Miller, Chief of Staff at Betterworks to share her perspective on the CoS role. With all of the hype around this somewhat squishy and nuanced position, we’re making an effort to bring you the insight and perspective you’re looking for. Jenna talks about her recent promotion to Chief of Staff and the ways in which the Chief of Staff role differs from her experience as an Executive Assistant. She also unpacks her expectations vs the reality of the position now that she’s in the thick of it. One of her clear distinctions is that in the EA role, you experience “quick wins” as you focus primarily on executing tasks on behalf of your executive. While in the Chief of Staff role, your wins and rewards take a bit longer to come to fruition since your initiatives are focused on not only the executive, but the entire org.

This is part-two of our two-part series with event planner extraordinaire Heather Keenan, President and CEO of Key Events.  Heather and her firm have orchestrated events the likes of which have been attended by queens, US Presidents, celebrities and the A-list of the business world. If you missed part 1, definitely give it a listen (Season 1, episode 16) where Heather shared how Executive Assistants could pull off a successful virtual event.  As in-person events resume, we wanted to bring Heather back on the show to hear her advice around carrying out a meaningful and successful in-person event (the best kind)!  Whether it’s a casual team happy hour or a formal executive dinner party, Heather says that every event exists to push business forward and it’s an Executive Assistant’s responsibility to nail that objective. One of her favorite tips when it comes to brainstorming and executing an event is “to paint with a big brush.” Join us for a conversation with tons of practical tips and lots of laughs! And you won’t want to miss her answer to our infamous REACH question with a twist. 

You’ve probably heard the term “seasoned” or perhaps even been labeled or felt as such. And in the Bay Area tech arena especially, it’s not uncommon to work alongside colleagues or even support executives who may be in their early 20s or 30s. So, we’ve decided to tackle the ambitious topic of what it means to age gracefully in your career as an Executive Assistant and, in particular, how you can avoid “aging out” of the EA career. Nicole Hawkins, Senior Manager of Administration at Patreon, who supports CEO Jack Conte, has volunteered to share her experience of being a “seasoned” EA and what it’s like to work with and support individuals who are younger than she is. We’ll be talking about how to stay relevant amidst younger talent, how to relate to an executive team and group of colleagues who seem to get younger not older, how to provide invaluable support despite age differences, and how to confidently package your experience when interviewing.