CCing my EA Podcast

Rachel Tan shares why asking an executive what outcome they want can save an EA from wasting time on the wrong solutions, how EAs bring overlooked experiences into rooms where decisions are made, and the difference between sensitive and confidential information. She also tells the story of a board dinner reservation that nearly became a disaster.

The EA cheat code: Ask what outcome they want

Earlier in her career, when an executive brought Rachel a problem, her instinct was to immediately return with solutions.

Now, she starts by asking:

“What is the outcome that you want from this?”

She might also ask how the executive feels about the situation and what they ultimately want to happen.

Those questions give Rachel the context she needs to understand how the executive wants her to show up. Instead of spending time developing 17 possible solutions with 17 different outcomes, she can focus on helping them reach the result they actually want.

The answer also creates useful precedent. If an executive explains why a particular interaction bothered them today, Rachel has more context for handling a similar situation tomorrow. She learns things the executive may not have thought to explain upfront.

That doesn’t mean Rachel withholds her own opinion. Once she understands the desired outcome, she can offer her perspective, challenge the approach if she believes it is wrong, and turn it into a more productive discussion.

Sometimes, the executive doesn’t know what outcome they want. The question makes them stop and think. They may return with an answer later, discuss it during their next one-on-one, or realize that the original problem no longer needs to be solved.

The cheat code is resisting the urge to solve too quickly. First understand where the executive wants to go. Then help them get there.

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Also in this episode:

• How Rachel moved from government work into tech and executive support
• What it means for an EA to be in the “war room”
• Bringing unheard experiences into rooms where major decisions are made
• Why holding confidential information can make the EA role lonely
• The difference between sensitive and confidential information
• What Rachel learned after an executive said, “Rachel tells me everything”
• A board dinner reservation that nearly became a disaster
• Using AI to document her impact and review how she spent her time
• Planning an international birthday celebration involving private jets
• Why being a trusted bridge remains the most fulfilling part of the job

At the time of recording, Rachel was the Director of Executive Administration and Strategic Programs at Benchling. She began her career in government before moving into workplace operations at a Series A technology company, where her responsibilities expanded into recruiting, company culture, events, and executive support. She eventually narrowed that broad role into a dedicated career in executive administration.

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Chapters:

0:00 Intro
0:22 How Rachel became an Executive Assistant
2:11 What it means to be an EA in the war room
3:43 Bringing unheard experiences into the room
4:53 The loneliness of holding confidential information
8:12 Confidential vs. sensitive information
10:12 EA cheat code: “What outcome do you want?”
12:25 When an executive broke Rachel’s trust
14:05 The board dinner that nearly became a disaster
15:32 Using AI to document your impact
16:55 Planning an international birthday celebration
17:49 What Rachel finds most fulfilling about being an EA
18:37 Outro

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Vimcal EA: https://vimcal.com/ea
CCing my EA newsletter: https://ccingmyea.com
Instagram: https://www.instagram.com/ccingmyea
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YouTube: https://www.youtube.com/@CCingMyEA
Spotify: http://open.spotify.com/show/6BuKDPxbOxFBO3y7wrRK4O
Apple Podcasts: https://podcasts.apple.com/us/podcast/ccing-my-ea-podcast/id1778714539

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The CCing my EA Podcast shares the real tactics and stories Executive Assistants learn from supporting busy executives.

Presented by Vimcal EA, the first calendar co-built with Executive Assistants: https://vimcal.com/ea

Leah Temena Husemann shares how playful “virtual bartering” helps EAs build relationships and manage competing requests, from charging three samosas for 15 minutes to asking for dog photos, recipes, or travel stories. She also explains when an EA should intentionally wait before carrying out an executive’s request and how to turn a folder of thank-you emails into a performance-review summary with AI.

The EA cheat code: Three samosas for 15 minutes

When someone asks for 15 minutes with Leah’s executive, she might joke that getting time this week will cost three samosas, while waiting until next week will only cost two.

The samosas aren’t really the point. Leah chooses something connected to the person and their culture or interests. It might be dumplings, pork buns, a photo of their dog, a recipe, or a story from a recent trip.

That small moment of humor turns a cold scheduling request into a more personal interaction. It helps the other person feel that Leah speaks their language, breaks down the initial barrier, and makes her more approachable.

From there, Leah can better understand what the meeting is actually for and how urgent it really is. If someone is leaving the company in four weeks, she can prioritize that conversation. If the request can wait, the relationship she has built makes it easier to push the meeting back without making the person feel dismissed.

Leah calls it a “virtual barter,” but one colleague eventually made it real. After traveling from Plano to Jersey City, he brought her an entire box of samosas because the meeting she had arranged proved so impactful.

This approach took time. Leah first needed to establish her credibility with her executive and the wider team before she felt comfortable adding more personality to these interactions.

The food is just the opening. The actual cheat code is finding a personal, playful way to turn a transactional request into a relationship.

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Also in this episode:

• Moving from the Philippines and beginning her career as a part-time filing clerk
• Building an 11-year partnership with the same executive
• Why a supportive executive relationship creates room for an EA to grow
• Learning not to judge someone from the first few interactions
• When intentionally delaying an emotionally charged request protects the executive
• Saving appreciative emails in a wins folder and using AI to summarize them
• Why building a community at work makes the role more fulfilling

At the time of recording, Leah was a Senior Executive Assistant at JPMorgan Chase, where she had worked for 13 years and supported her executive for 11. She also coached colleagues internally, led workshops, supported offsites, and helped other EAs learn how to use AI.

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Chapters:

0:00 Intro
0:31 Leah’s role at JPMorgan Chase
1:31 Eleven years supporting the same executive
2:20 Why a supportive executive relationship matters
4:27 From filing clerk to Senior Executive Assistant
6:42 EA cheat code: Three samosas for 15 minutes
8:51 Why the “virtual barter” works
10:48 When someone actually brought the samosas
11:46 Earning permission to show more personality
13:33 Adapting the tactic beyond food
14:32 Don’t judge someone from the first few meetings
16:56 When not to do what your executive asked
18:25 Build a wins folder and let AI summarize it
20:16 The most fulfilling part of the job
20:44 Outro

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Vimcal EA: https://vimcal.com/ea
CCing my EA newsletter: https://ccingmyea.com
Instagram: https://www.instagram.com/ccingmyea
TikTok: https://www.tiktok.com/@ccingmyea
LinkedIn: https://linkedin.com/company/ccingmyea
YouTube: https://www.youtube.com/@CCingMyEA
Spotify: http://open.spotify.com/show/6BuKDPxbOxFBO3y7wrRK4O
Apple Podcasts: https://podcasts.apple.com/us/podcast/ccing-my-ea-podcast/id1778714539

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The CCing my EA Podcast shares the real tactics and stories Executive Assistants learn from supporting busy executives.

Presented by Vimcal EA, the first calendar co-built with Executive Assistants: https://vimcal.com/ea

Caitlin Jovovich shares how playing to your audience can help EAs win support without formal authority, from orchestrating a team “one-two punch” to reframing disposable cameras as an event activation. She also tells the story of pulling together a COVID-era IPO celebration days before giving birth.

The EA cheat code: The “one-two punch”

Caitlin’s broader principle is to play to your audience. When you need to move an idea forward without much formal authority, having a good idea isn’t always enough. You also need to understand how the person in front of you communicates, absorbs information, and needs the idea presented.

One way Caitlin applied this was something her team began calling the “one-two punch.”

Before an important meeting, the team would workshop the idea together and poke holes in it from their executive’s perspective. They would then decide how to present it: one person might lay the groundwork, another reinforce it, and the person with the most trust or context explain why it mattered.

For one proposed social media post, this preparation helped the team connect an idea that seemed unimportant in the moment to a larger strategy planned for three months later. Caitlin believes the idea probably would have died if she had simply presented it alone.

The same principle helped her get approval for disposable cameras at a company offsite. The CMO rejected them when they were presented as expensive, disposable swag. Caitlin reframed the exact same idea as an event activation that would create shared memories, produce employee-generated photos, and eliminate the need for a photographer. It was quickly approved.

The idea didn’t change. Caitlin changed how she presented it based on the person receiving it.

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Also in this episode:

• How Caitlin unexpectedly became an Executive Assistant
• Bringing repeatable processes into scrappy companies
• Becoming the organizational “catch-all drawer” and then cleaning it out
• Producing a COVID-era IPO celebration with limited information and shifting dates
• Why making difficult things happen remains fulfilling

At the time of recording, Caitlin was the Executive Business Partner to the CEO at Jasper. Her career spans executive operations roles at established global brands and fast-growing technology companies.

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Chapters:

0:00 Intro
0:20 How Caitlin became an EA
2:27 From luxury brands to fast-moving startups
4:10 Building processes in scrappy companies
5:23 Creating an Office of the CEO playbook
7:21 EA cheat code: Play to your audience
8:24 The team “one-two punch”
10:34 Winning support for a long-term social strategy
12:57 Turning disposable cameras into an activation
16:23 Pulling off an IPO party during COVID
18:39 Why making the impossible happen is still fulfilling
20:17 Outro

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Vimcal EA: https://vimcal.com/ea 
CCing my EA newsletter: https://ccingmyea.com
Instagram: https://www.instagram.com/ccingmyea 
TikTok: https://www.tiktok.com/@ccingmyea
LinkedIn: https://linkedin.com/company/ccingmyea
YouTube: https://www.youtube.com/@CCingMyEA 
Spotify: http://open.spotify.com/show/6BuKDPxbOxFBO3y7wrRK4O 
Apple Podcasts: https://podcasts.apple.com/us/podcast/ccing-my-ea-podcast/id1778714539

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The CCing my EA Podcast shares the real tactics and stories Executive Assistants learn from supporting busy executives.

This episode is presented by Vimcal EA, the first calendar built specifically for Executive Assistants: https://vimcal.com/ea

Jodie Mears shares why protecting an executive’s time sometimes means being professionally unpopular, how she documents her impact, and why “just because you can fix it doesn’t mean you should own it.” Plus, the story of the time she chased down a UPS van to fix a mistake.

The EA cheat code: Be professionally unpopular

Executives need someone to protect their time, and leaders often struggle to create boundaries for themselves. In Jodie’s experience, they’re often much happier allowing their EA to create those boundaries for them.

That might mean allowing an executive to say:

“Jodie won’t let me do that.”

Or:

“Jodie has protected that time for project work.”

For the EA, this requires removing yourself from the equation emotionally and not worrying too much about being blamed. The point isn’t to be difficult for the sake of it. It’s to protect the bigger picture and make sure the executive’s most important goals still get fulfilled.

Sometimes, being professionally unpopular is simply part of the job. All for the right reasons.

Also in this episode:

• How Jodie accidentally became an Executive Assistant
• Friday Wins: documenting your impact while it’s still fresh
• Chasing down a UPS van after realizing she’d made a mistake
• Her Time, Tone, Turf framework for deciding when to escalate
• Why constantly rescuing everyone can keep an EA trapped in tactical work

Jodie is a C-suite Executive Assistant at Bentley Systems and a speaker, mentor, and writer focused on helping administrative professionals grow their confidence, visibility, and impact.

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Chapters:

0:00 Intro
0:24 How Jodie accidentally became an EA
2:26 Personal brand, visibility, and showing your impact
5:49 Friday Wins: how Jodie tracks her impact
8:17 EA cheat code: “Be professionally unpopular”
11:09 The time Jodie chased down a UPS van
14:13 Time, Tone, Turf: when to escalate
15:25 Getting fired over spelling mistakes
16:38 “Just because you can fix it doesn’t mean you should own it”
18:30 What Jodie finds most fulfilling about being an EA
19:29 Outro

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Vimcal EA: https://vimcal.com/ea 
CCing my EA newsletter: https://ccingmyea.com
Instagram: https://www.instagram.com/ccingmyea 
TikTok: https://www.tiktok.com/@ccingmyea
LinkedIn: https://linkedin.com/company/ccingmyea
YouTube: https://www.youtube.com/@CCingMyEA 
Spotify: http://open.spotify.com/show/6BuKDPxbOxFBO3y7wrRK4O 
Apple Podcasts: https://podcasts.apple.com/us/podcast/ccing-my-ea-podcast/id1778714539
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The CCing my EA Podcast shares the real tactics and stories Executive Assistants learn from supporting busy executives.

Presented by Vimcal EA, the first calendar co-built with Executive Assistants: https://vimcal.com/ea