When to join a Chief of Staff community

How to build a world-class peer network (even if you never pay for one)

Author

Regina Gerbeaux
June 15, 2025 • Reading Time: 14 minutes

Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.

Preface

There’s a lot of buzz around operator communities, especially for Chiefs of Staff. If you’ve ever wondered whether joining one is worth your time - or your team’s money - you’re not alone. Let’s talk about what makes a community valuable and how to build your own operator brain trust.

Dear Regina,

Would you recommend joining communities like the Chief of Staff Network? Did you find those helpful at all? If there are any specific resources, books, etc. you found helpful, I would love to know! I’ve been loving the resources on your website.

(Chief of Staff, Series A company, ~20 people)

Dear Operator,

I should preface this response first by saying I am friends with many of the people who run Chief of Staff paid communities - I think the world of them and believe what they create is a net positive to the ecosystem.

I have done talks for the Chief of Staff Network and also Chief of Staff Roundtable, and I have sent plenty of referrals to them as well as the Ask a Chief of Staff and Operators Guild communities. If I didn’t believe in the power of high-quality, paid communities, I wouldn’t have said yes to collaborating with them.

It’s also worth noting that I was Head of Operations at On Deck for a year, back when our bread and butter were fellowships designed for specific verticals and roles. The Chief of Staff fellowship was, by far, one of the most popular ones we offered. So, that should tell you off the bat that I’m not against paid communities.

The two things that are abundantly true for Chiefs of Staff and Operators are:

  1. You need peers who are fellow operators. The role can be very lonely otherwise.

  2. You don’t necessarily need to pay for access to them, but it can certainly be a shortcut.

The best Chiefs of Staff I know are in deep, trusting relationships with 5–10 other operators who (1) can relate with their own experiences, and (2) tell the truth without mincing words. Sometimes, you can build this on your own, but sometimes, it makes sense to rely on a paid community to do this for you.

How to Gain the Most out of Paid Communities

Communities work exceptionally well if you’re willing to put in the time and effort to make the most out of it.

If you’re signing into Slack or Discord one time, introducing yourself, and you sign out never to log back in again, you won’t create the relationships you want. If you attend one or two events, silently participate, and never engage, you won’t learn what you want to learn.

Most paid communities are built around content and access. While this is great, you can get tons of content for free (including this newsletter, for example!) If you’re joining purely for the content, it doesn’t make much sense - unless, of course, the person writing the content is someone at the top of their field, and you’ll get access to content you wouldn’t get anywhere else. (More on that later… 😉 )

So what you’re really looking for is the clarity and collaboration aspect when you join a community.

The best way to get this is to be involved in the community. You can do this in a variety of ways:

  • Connect with people in 1-1 calls. You’d be surprised at the number of people who would be open to doing a virtual coffee with you! Look in the intros channel or your community’s directory, and find 1-2 people that seem interesting and whose paths and trajectories are similar or complimentary to yours. Ask them to hang out.

🛑 Don’t ask to just “pick their brain” or “have a virtual coffee” - the more senior the operator, the less likely they are to say yes.

Instead, point out the few things you have in common, state clearly why you think it would be great for the two of you to meet (“we have a lot in common and I’d love to say hello”), and make your request directly.

  • Ask lots of questions in the Q&A channel. Be the person that asks thoughtful questions, because chances are, there are at least two other operators in the community that have the same question as you. If you engage in the Q&A channel, you’re likely to find a lot of the clarity you’re searching for as an operator, and you can learn from other operators. This is also a great way to interact with more senior operators, who don’t necessarily have time for 1-1 coffee chats, but will take 5 minutes to respond to your Slack message (especially if it’s well-written and concise.)

  • Offer help more than you receive help. Everyone has something to offer, even the most junior of Chiefs of Staff. Participate frequently in discussions on Slack and in virtual and IRL events where you can offer some of your knowledge or experience to the person asking the question.

✅ Back when I had very little experience to offer, one thing I knew I could offer was the gift of great questions. It is free to offer clarifying questions, and flexes your critical thinking muscles.

Questions might start with…

“What do you think about…?”

“Have you considered how X might impact…?”

“How does this lead to your long-term goals of…?”

“How might this impact day-to-day operations as it relates to…?” and so on.

If you can ask great questions, even as a junior Chief of Staff, it demonstrates thoughtfulness and sharp thinking. It also makes you a better operator. Don’t shirk away from giving help!

  • Participate in events. Your paid community will have speaking events online, and probably some conferences or IRL get-togethers if you’re in a major hub like San Francisco, Los Angeles, or New York City. When speakers come, participate! Ask them good questions. Leave comments in the chat - your engagement inspires other quiet people to also speak up. This creates a vibrant community.

  • Be encouraging and celebrate wins in public. When someone says they’ve done something awesome as a Chief of Staff, celebrate it! Post it somewhere so you can actively create a culture of celebration. And if you’ve done something awesome, post it, too.

    You know how it’s inspiring to see someone post progress pics of their gym gains and their bodies getting stronger and healthier? This is along the same lines. We do this for physical improvements, but shirk away from doing this in skill improvements. If your community doesn’t do this, start doing it, and watch as others begin to join you in a culture of celebration.

  • Make it a point to connect with interesting members. When I was starting out my tech career as an operator, I had maybe 30 LinkedIn connections and knew no one in Silicon Valley outside of my hiring manager. I set an arbitrary goal to connect with 500 interesting people over LinkedIn through my work within two months. I think I got there in one.

    Every time I met someone who I found interesting, I immediately sent a LinkedIn message with a note: “It was wonderful meeting you today through _____! I would love to stay in touch.”

    9 times out of 10, they would accept my connect request and respond with something like, “Great to meet you too!” And that would open up the line of communication.

    Years later, when I needed to search for an operator who knew XYZ or had domain expertise in something, when I would resurface this person, I now had the LinkedIn message to give me context on how I met this person, when we connected, and why they should talk to me again. It usually goes something like, “Hey ____, not sure if you remember me - we connected over ____ x number of years ago. Hope you are doing well! I wanted to ask you…[request goes here.]”

    I’ve still never gotten ghosted, not even once, when I write this way. They see our message history, remember our exchange was pleasant, and immediately want to help. I have helped people get jobs, meet customers and investors, and many other ways through this practice. My network is one of the things I have going for me, and I love using it to help the people in my life who I care about.

How to Create a Free Community for Yourself

While you don’t have to join a paid community to have a community, it can be a shortcut. We’re lucky enough to have some really awesome communities already up and running with accessible yearly membership fees.

But what if you’re frugal, or your company isn’t resourced enough to sponsor your membership?

Here’s how you can create your own community to hold you over in the meantime.

  • DM people with thoughtfully crafted messages. Never underestimate the power of a cold DM or LinkedIn request! I get these all the time and it might surprise people to know I say yes very often if the messages are well-written.

🛑 As I mentioned earlier, avoid phrases like “picking your brain” or “virtual coffee.” Those are almost always instant “no”s in my book. Also in that same category: “I saw we had mutuals in common” or, “We went to the same school, let’s connect.” So what? That means nothing to me.

Instead, rely on highlighting something they’ve done (“I deeply admired your piece on…” or, “I’ve followed your work since you were working at…” or something similar), and tell them you’d love to stay plugged in on their journey or ascent.

  • Ask for advice. If you want silence, ask to connect. If you want connection, ask for advice.

  • There is an incredible phenomenon that happens when you ask people for advice. People LOVE feeling smart. Asking them for advice when your question is thoughtful, simple, and pointed usually results in a response. And when someone responds and gives you advice, the most magical thing happens.

    They become invested in your journey. They literally want to know how things are going to pan out if you take their advice. They care more, because now they’re somehow connected to you.

    If you can ask a question like, “Hey ___, I’m dealing with X situation right now - would love to get your take. What would you do if ____? I think you probably faced something similar at [your company.]”, it’s almost inevitable that they will respond if they have time to.

  • Systemize your outreach. Make it a point to reach out to people on a frequent basis. Connect and follow people whose work you admire. Share notes of love and appreciation at least once or twice a week.

    I sent out so many of these messages in my earliest days, that I essentially built my network by making sure I expressed gratitude to the people I wanted in my life in an authentic manner.

  • Make intros yourself. Everyone has a network, even if it’s small! I would offer to make intros even when my LinkedIn connections were <100 people big. I would keep in mind interesting personalities and find ways to connect two people I really liked.

    I’m certainly not the master of this - if you want to read more, I highly recommend reading Adam Grant’s Give and Take and jumping to the section that talks about how Adam Rifkin does this. (In fact, Adam Rifkin and I connected about a year after I read this book - a testament to his ability to connect with people far and wide!)


    Offer to be helpful, and people will offer to be helpful to you.

Conclusion

Most CoS communities give you access to knowledge that you can replicate with AI and a little curiosity. If you’re paying, pay for calibration and connection, not commoditized info.

And if you’re reading this - you're already ahead.

Because you know where to find the stuff that’s actually good. Like my templates and resources, and this newsletter.

The best operators I know don’t go it alone. But they’re also not wasting time inside massive Slack groups hoping to get value from lurking.

You don’t need a badge, a membership, or a logo. You need your people. The ones who get it. Who’ll call you on your BS.

Just don’t do this work alone.

Until next time,

Interlude: School of Operators 👀 (surprise!)

I’d be lying if I said I didn’t constantly think about how to help operators connect better. As a result, I’m thinking about launching the School of Operators.

It would include a crash course on how to be operationally excellent with new, members-only templates and content released frequently, off-the-record monthly masterminds for CoSes and COOs (limit 8-10 pp group), and facilitated coaching from me.

This would be invite-only and optimized for people who are high-trust, no-BS, and tomorrow’s greatest C-Suite leaders of Silicon Valley and beyond.

Still in the early planning stages, but if your ears perked up reading that, you can drop your name here to stay in the loop by replying to this email.

Resources Mentioned 📌 

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About Regina Gerbeaux

Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale).

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.

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