💥 I Survived a Reorg and Made It Look Easy

Hi Friends,

Reorgs are like earthquakes, you may not have caused the shift, but you're the one keeping everything together while everyone else is still processing. Whether it's a quiet leadership shuffle or a full-blown org chart explosion, EAs are the first to notice, and often the last to be looped in.

This week, we’re talking about what it really looks like to show up like an operator when everything is in flux. From asking the questions no one else is asking, to designing new rhythms that make leadership look like they have it together (spoiler: they don’t), here’s how to navigate a reorg like a strategic powerhouse.

With love, and lots of Coffee,

Chrissy

We officially launched our private Slack community for EAs yesterday! 🎉

👀 If you applied, check your inbox (and your junk folder — just in case).

🚪 Haven’t signed up yet? Apply now before your exec forwards this to you. 😉

👉 Join The Inner Office

We’re thrilled to announce that Cortney Hickey, Executive Assistant to the CEO at Zapier, will be joining us for an exclusive Inner Office AMA (Ask Me Anything) — available only to community members.

She’s one of the sharpest EAs in tech, leading at the intersection of operations, product thinking, and executive leverage. We’ll talk about:

You do not want to miss this.

📬 Members of The Inner Office will get the invite directly — join us and bring your best questions.

TL;DR: Leadership has changed, priorities are shifting, and people are confused but afraid to ask.

What people hear: "We're optimizing for the future." What it really means: "We’re reprioritizing everything and hoping someone’s taking notes. (Hint: that someone is probably you.)"

Red flags a reorg is brewing (or already happening):

Reorgs are stressful, but they’re also a massive opportunity to reposition yourself.

A few years ago, I joined a new team that was mid-reorg. No one knew who owned what. People were hesitant to speak up, everything felt a little... sideways. 🙃

Instead of waiting to be told what to do, I proposed a leadership meeting cadence, created a shared doc to track ownership gaps, started a distribution list, and asked alignment-building questions execs weren’t even thinking to ask. That’s how you shift from task-taker to trusted operator.

Here are tips to help you do the same:

1. Map the Chaos Start identifying who reports to who, what changed, and what’s still unclear. Even if it’s unofficial, clarity is currency right now.

2. Propose a Leadership AMA or All-Hands Use tools like Slido or Google Forms to collect anonymous questions ahead of time. Categorize them. Prep your leaders. You’re not just booking a meeting, you’re facilitating cultural trust.

3. Suggest a "Reorg Rhythm" Offer a new meeting structure (e.g. weekly syncs, bi-weekly pulse checks, or decision-making workflows). Bonus points if you run it for them.

4. Ask Strategic Questions “What’s falling through the cracks?” “What does success look like in 60 days?” “What do we need to unlearn from the previous structure?”

5. Build Clarity Where There Isn’t Any Create a shared doc with new roles, goals, and gaps. Track open loops, flag misalignment, clarity = influence.

6. Stay Calm, steady & Observant. You don’t need to have all the answers, but your presence can anchor the room