Dear Regina,

Step 1: Live in their world - even if it sucks (temporarily).

When I first started my Chief of Staff role full-time, I flew from my home in Seattle to Kauai where my exec lived and worked all of his hours. Unfortunately for me, he liked to start his first meetings at 8am Pacific, which was 5am Hawaii time.

There isn’t quite anything like waking up in an AirBnB before the roosters start crowing all across the island, before any real coffee shop is open, and stumbling into the office bleary-eyed. But that was my reality for five weeks straight.

Honestly, it was the best investment of my time. Showing up next to him every single day for weeks on end was how I got a front-row seat to his real working style, how he moved through decisions, what triggered him, and where his blind spots were.

You don’t need to do this forever, but do it upfront if you can.

If you're remote, make it a priority to spend at least one full workweek in-person each quarter.

Having facetime allows you to also do fun things outside of work. While in town, Matt and I would go to restaurants together after work. We would go out to the beach with his friends and I’d pack a cooler full of beer and seltzer water. We’d do bonfires late at night on the beach.

You get to serendipitously know your exec outside of work, too, but it’s easiest when you are the one creating that serendipity.

Step 2: Read their emails and calendar events like it’s your new favorite book series.

My first week working as a Chief of Staff, I read 2-3 years’ worth of my exec’s emails.

It certainly didn’t help that Matt was probably at “Inbox 100,000” (as opposed to “Inbox Zero”.) As someone who has been at Inbox Zero since 2011, it bothered (ok, really bothered) me that he wasn’t at Inbox Zero.

I quickly skimmed every important-looking sent item, deleted a bunch of automated emails for old calendar invites that were just taking up room in his inbox, and unsubscribed from five million newsletters he never read.

In his email, I looked up names of clients and investors that showed up in his calendar to better understand his relationship to everyone. I made myself an ongoing list of outstanding questions I would want answers to, and made a mental note to either answer those questions myself, or ask him later when the opportunity came up.

It was through this practice that I learned:

• His tone and communication style

• What he prioritized vs. ignored

• How he handled tough conversations

• What triggered him (this is important!)

After a week, I could draft emails in his voice. After a month, I could anticipate how he’d respond. The “aha” moment for me was when I would watch him coach: his coachees would tell him their problems, and I would silently make an educated guess on what his response would be. I could predict which anecdote he would tell, which coachee he would cite, which write-up he would share, and what advice he would give.

I was not only learning how to be my exec, but I was learning how to be a world-class coach in the process.

To this day, I still joke that I can turn on my alter ego of “rich Caucasian guy in his mid 50s with the confidence of an Ivy-League / MBA graduate / CEO coach to billionaires” just by recalling my days as his Chief of Staff. Admittedly, it’s pretty powerful stuff as a petite Asian woman that sometimes gets mistaken for being a high schooler, especially with my preference for backpacks and sneakers.

And it’s not just about mimicking for the sake of it. It builds trust - because humans trust what feels familiar. You become the person who “gets them,” which leads to more autonomy and less micromanaging.

Step 3: Create an async channel to capture big-picture thinking. 

Even before becoming a Chief of Staff, I’ve sworn up and down on the efficacy of async channels.

When I was Head of Operations at On Deck, I had about 20 direct reports, all ops associates and ops leads.

I also had another 5-7 EAs that skip level reported to me, and had to make sure they were unblocked with whatever tasks they had on their plates.

And that’s not counting the 15 Program Directors I worked with closely to make sure their business lines would launch successfully (and profitably) from Day One.

My point is, I had a lot of people to unblock, and not a lot of time. And a lot of people needed things from me, and I had to give it to them quickly.

Async channels saved my sanity.

You must have a dedicated Slack channel with your exec that’s just the two of you. In it, drop:

• Strategy questions

• Open-ended prompts

• Clarifying follow-ups

• Weekly recaps and nudges

Make it ridiculously easy for your exec to answer. “Hey - reminder that this decision needs to be made by Friday. I’m leaning toward X because of Y. Objections?”

Here’s one of my favorite examples from Nat, a frequent collaborator:

I write more about this exact setup in my Slack write-up - especially the Async Channel setup section. Go read it, copy the format, and make it your own.

Remember the “list of questions” I made in Step 2 above? Anything I couldn’t answer on my own would end up in this async channel. It made it super easy for my exec to batch-answer everything whenever he had time. I got my answers; he got his blocked time, and a Chief of Staff operator who could seemingly read his mind.

To this day, I use async channels with all of my assistants and collaborators. It helps us make sure nothing falls through the cracks.

Step 4: Stop asking for permission. Declare intent with a veto window.

You learn how your exec thinks by doing it as often as possible. Start making decisions you think they would make, before they make them. They’ll be impressed with your ability to emulate their decision-making logic tree.

Here’s how you do this:

• Propose what you’re going to do

• Give your exec 48 hours to veto

• Default to action unless they intervene

IMPORTANT: Get buy-in for this system first. Frame it as a way to keep the team lean and fast-moving, rather than waiting around for approvals.

It’s a guarantee that they will veto some of your decisions. It’s a guarantee you will sometimes predict their decision incorrectly. Don’t get defensive when this happens - it’s part of the learning process!

Instead, listen intently.

What was incorrect about your pattern-matching? What did they see that you missed? Where did your logic tree differ from theirs?

Over time, you’ll refine your internal compass so well that your decisions will become nearly indistinguishable from theirs.

And when that happens? You’re not “support” anymore. You’re now a strategic thinker.

A common retort I get often is, “But Regina, what if I don’t agree with my exec’s decision? Do I have to keep just making the same decisions they would make?”

Of course not! But the most compelling way for you to make your own decisions is not only being able to back up your own thinking, but showing them you understand their thinking, too.

Have you ever tried to argue with someone? (Join the club, of course you have.) The more you can show your opponent that you understand where they’re coming from and can effectively steelman their position, the more likely they are to steelman yours, too.

But you have to start from a place of trust, and part of that trust is showing your exec you can think like them. Skip this step at your own peril.

Step 5. Make 1-1s the most valuable time your exec can spend each week.

Execs often cancel 1-1s or schedule over them because they think it’s a waste of their time. Don’t allow yourself to run shitty 1-1s, and you won’t have this problem.

How do you avoid shitty 1-1s? By driving them yourself. You’re the operator here - don’t forget! No one is going to run meetings better than you.

I recommend using my 1-1 Meeting Template religiously. It gives you everything you need to run your 1-1s effectively, including:

• A clear agenda

• Strategic items to discuss

• A track record of everything they’ve asked for, and what’s been done

• A calendar review section, where you can close the loop on old events, prepare for new ones, and look into the horizon to be ready for anything else that comes up

If you pair the 1-1 Meeting Template with my Master Task Board template, you will literally never lose track of a single item.

Make this meeting so high-value that your exec walks away thinking, “That was the best use of my hour all week.”

Then, you’ll never have another 1-1 canceled, ever again.

I did this with my exec, and he actually requested we make our 1-1s longer to cover even more ground. They ended up being two hours. Because Matt charged $15,000 per hour in coaching fees, I knew my bar for my 1-1s with Matt had to be, at minimum, $30,000 worth of ROI every time.

Are you making your 1-1s that valuable?

Step 6. Get good at taking feedback - even when it sucks.

I knew Matt’s trigger feeling was anger. Sometimes, he’d say stuff I know he didn’t mean.

When that happened, I would pretend he was a toddler throwing a temper tantrum. It helped me shift from feeling offended, to feeling compassionate.

While you might call that condescending, I call it holding space for his big feelings, being good at my job, and shielding my heart from hurt.

Can you hear hard things without flinching?

Can you separate their tone from the substance?

Can you find the fear or stress behind the frustration?

Because here’s the truth: your exec will say something awful to you one day. They’ll snap, be rude, maybe even insulting.

Your job isn’t to take it personally. Your job is to say, “Alright, I’ll see you tomorrow,” and show up just as grounded. After all, feedback is the fastest builder of trust.

Get your emotional needs met from peers, mentors, or other operators - not your exec. That’s how you stay steady. And while I may be biased, this is one of the many things a coach is good for: often, CEOs will ask me to coach their CoSes, because they know it means I can hold space for them. This space allows them to have a healthier relationship, because their emotional needs are being met outside of their already-super-close relationship.

Bonus: Humans love their own reflection.

If you ever feel weird about “mirroring” your exec’s behavior, remember this:

“We love ourselves more than other people, but care more about their opinion than our own.”  -  Marcus Aurelius

Mirroring their thinking isn’t manipulation - it’s how you become trusted. And eventually, it's how you make space to evolve beyond just mirroring - into leading in your own right.

Linked Resources:

• 1:1 Meeting Template | Coaching Founder

• Master Task Board | Coaching Founder

• Slack Async Channel Write-up | Coaching Founder

• How to build trust with your exec | Coaching Founder

• Feedback: Leave nothing unsaid | Coaching Founder

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.