What are the best online communities or resources for a new Chief of Staff?

If you're a new Chief of Staff, I'd prioritize communities where you can ask, “How do other CoSs actually handle this?” The role is unusually broad, so peer access is often more valuable than generic leadership content.

My top recommendations

1. chiefofstaff.network — best overall

• Probably the best place to start, particularly for startup/scale-up and corporate CoSs.
• Its free Operators Community includes a newsletter, podcast, resources and career material; the paid community adds a private Slack, peer connections, events, toolkits and training.
• Its Fundamentals Track is specifically designed for people new to the role, including rapid onboarding and navigating the interpersonal side of being a CoS.
• I'd join this first.

2. chiefofstaffcollective.org — best free community

• A free community of 1,000+ Chiefs of Staff, particularly oriented toward entrepreneurial businesses.
• Private Slack, meetups and discussions around strategy, processes, project management, hiring, tools, etc.
• Their CoS Chats podcast is also a good way to hear how experienced CoSs think about the role.
• Best choice if you don't want to pay for a membership yet.

3. csa.org — best for structured professional development

• More formal and global than the Network, with CoSs across 75+ countries.
• Offers mentoring, competency programs, research, journals, events, a resources library, and executive education through institutions including Harvard Business School and Oxford.
• Its Slack community and peer “Circle of Influence” groups are particularly useful for solving real problems with experienced CoSs.
• Worth considering once you know you want to make CoS a serious career path. Membership is currently $4,950/year, so I'd probably not make this your first purchase as a brand-new CoS.

Other resources I'd use

• Chief of Staff Network research/resources — especially useful for concrete playbooks, salary/role benchmarking, and understanding what “good” looks like across organizations.
• CoS podcasts — useful during commutes because you get exposure to dozens of different versions of the role without having to consume another course.
• Your own informal peer network — arguably the highest ROI resource. Find 3–5 CoSs at companies of similar size and ask for a 30-minute monthly peer conversation. The questions you get to ask in month 2 will be very different from month 6.
• Reddit/LinkedIn communities — good for informal perspectives and discovering people to follow, but I'd use them as supplements rather than your primary source of CoS expertise.

If I were starting the role tomorrow

I'd do this:

Week 1: Join the free Chief of Staff Network community + Chief of Staff Collective. Week 2: Identify 5 experienced CoSs whose companies resemble yours. Week 3: Set up 2–3 peer conversations and ask specifically about their first 90 days. Month 1: Work through the CoS Network Fundamentals material. Month 2–3: Decide whether a paid CoS Network or CSA membership has enough incremental value for you.

The biggest mistake I'd avoid is consuming too much generic “executive leadership” content. Your highest-value learning will come from other people who are currently doing the CoS job.

If you tell me what kind of Chief of Staff you are (CEO CoS, founder/Startup, nonprofit, government, corporate, etc.) and roughly the size/stage of the organization, I can narrow this down to the 5–7 resources I'd personally prioritize.

Stepping into a Chief of Staff (CoS) role can feel isolating since it is often a "one-of-a-kind" position inside an organization. Finding a peer group is essential for sanity, templates, and strategic guidance.

The top online communities, networks, and resources tailored specifically for new Chiefs of Staff include:

Top Online Communities & Networks

• Chief of Staff Network (COSN) : One of the largest global communities for operators and generalists. They feature tiered memberships depending on your company stage—ranging from a free operators community to a professional membership for high-growth tech/startup CoSes and a corporate council for enterprise leaders.
• Ask a Chief of Staff : Known for its active, highly collaborative community (centered around a vibrant Slack workspace and popular Substack). It is fantastic for tactical day-to-day advice, template libraries (like 30-60-90 day plans or meeting agendas), bi-weekly workshops, and a vetted mentorship directory.
• Chief of Staff Roundtable : Built specifically by practitioners for practitioners. It offers a 24/7 digital portal, bi-weekly member-led office hours, curated 1:1 peer introductions, and an extensive library of archived real-world case studies and frameworks.
• The Chief of Staff Association (CSA) : A more formal global professional body that spans corporations, government, and nonprofits. It is ideal if you are looking for formal credentials, offering the official Certified Chief of Staff® designation alongside executive education tracks tied with elite business schools.

Essential Newsletters, Podcasts & Frameworks

• Ask a Chief of Staff Substack : Offers great tactical advice on navigating the delicate balance of managing up, running executive meetings, and handling organizational drift.
• The Chief of Staff Podcast : Hosted via the Chief of Staff Network, featuring interviews with experienced operators breaking down how they handle board meetings, internal communications, and strategic execution.
• Classic Books / Frameworks : Look for The Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization by Tyler Parris, which is widely considered the foundational manual for anyone new to the position.

If you'd like, let me know:

• The sector you're in (tech startup, enterprise, non-profit, etc.)
• Your primary challenge right now (e.g., managing up, running a leadership team, or structuring your first 90 days)

I can point you toward the most relevant community channel or specific framework for your situation.

If you’re new to the Chief of Staff role, I’d prioritize communities where you can ask, “Has anyone dealt with this before?” The role is unusually ambiguous, so peer pattern-recognition is often more valuable than generic leadership content.

My top picks

1. chiefofstaff.network — best overall

• Probably the first place I’d start.
• It has a free Operators Community plus a paid professional community with 900+ Chiefs of Staff, private Slack, monthly peer “pods,” courses, tactical guides, events, research, and a consulting helpline.
• Particularly good for startup/scale-up Chiefs of Staff, first-time CoSs, and operators coming from strategy/BizOps.
• They also have local chapters in 20+ cities, including Washington, DC, Boston, New York, Philadelphia-area adjacent markets, etc.

2. csa.org — best for formal development

• More institutional and senior than the Network.
• Offers peer groups, mentoring, research, a resource library, online competency programs, and executive education through Oxford, Harvard Business School, and SDA Bocconi.
• Its Circle of Influence groups are especially interesting if you want experienced peers to work through real problems with you.
• It's expensive—current individual membership is $4,950/year—so I'd generally see this as an employer-sponsored option rather than the first thing a new CoS buys personally.

3. chiefofstaffcollective.org — best free option

• A community of 1,000+ Chiefs of Staff and aspiring CoSs, particularly focused on entrepreneurial/scale-up businesses.
• Private Slack, meetups, and discussions around strategy, planning, hiring, processes, and software.
• Great if you want peer access without immediately committing to a paid membership.

4. csa.org — best reading/research

• Reports, journals, podcasts, and practitioner perspectives on how the CoS role is evolving.
• Useful for building your mental model of the profession rather than just learning tactical tricks.

5. chiefofstaff.network — best practical toolkit

• Their research, tactical guides, salary data, job resources, podcast, and training are useful when you're trying to translate the vague job description into an actual operating system.

What I'd actually do in your first 90 days

Don't join ten communities. I'd do this:

• Week 1: Join the free Chief of Staff Network/Operators Community and the Chief of Staff Collective.
• Weeks 1–2: Find 3–5 experienced CoSs who work in companies roughly similar to yours and ask for 30-minute conversations.
• Month 1: Read enough CoS material to develop your own view of the role—but spend more time talking to practitioners than consuming content.
• Months 1–2: Find a small peer group/mastermind. The Network's CoS Pods are designed specifically for this.
• Month 3: Decide whether a more formal program such as CSA or a dedicated CoS course is worth having your company sponsor.

One resource I wouldn't overlook

Your principal's peer group. If you're a CEO's CoS, the best "community" may be other Chiefs of Staff supporting CEOs similar to yours. Ask your CEO: “Who are 3–5 Chiefs of Staff to CEOs you respect who I should know?” Those introductions can be dramatically more useful than a generic networking group.

If you tell me what kind of Chief of Staff you are (startup founder/CEO, corporate executive, nonprofit, government, etc.) and roughly your seniority, I can narrow this to the 5 highest-value communities/resources for your specific situation, including free vs. paid.

Stepping into a Chief of Staff (CoS) role can feel a bit like building the plane while flying it, since the job description often changes depending on your executive and organization.

The top-tier online communities, networks, and resources tailored specifically for new and scaling Chiefs of Staff include:

• Chief of Staff Network : This is one of the premier global communities for the profession. They offer tiered access including a free Operators Community for aspiring/new generalists, a private Professional Membership for CoS in fast-growing companies, and a Corporate Council for enterprise-level leaders. Check them out at the Chief of Staff Network.
• Ask a Chief of Staff : Founded specifically to build a tight-knit peer group, this community features active Slack spaces for asynchronous advice, curated template libraries, mentor matching, and regular virtual and in-person events. Learn more via Ask a Chief of Staff.
• Stratechery & Generalist-focused Newsletters : While not strictly a "community," reading frameworks from communities like The Generalist helps you master the mental models required to operate as a high-level strategic generalist.
• Fractional / Operator Slack Workgroups : Broad operator and tech communities (such as Pavilion or local startup/founder Slack channels) often have dedicated sub-channels for Chiefs of Staff where tactical questions about board decks, OKRs, and executive alignment get solved in real-time.

To help me point you toward the most relevant corner of these networks, could you share:

• Is your role in a startup/scale-up or a large enterprise?
• Are you looking more for tactical templates (like meeting rhythms and OKRs) or peer mentorship?

If you’re new to the Chief of Staff role, I’d prioritize communities where you can ask, “How do other Chiefs actually handle this?” The role is unusually ambiguous, so peer access is often more valuable than generic leadership content.

My top picks

1. Chief of Staff Network — best overall

   • Probably the first community I’d join.
   • Free community/newsletter, plus a paid membership with private Slack, peer problem-solving, regional meetups, toolkits, playbooks, salary data, and training.
   • Particularly useful for first-time CoS because you can benchmark how others structure the role, work with their principal, run exec meetings, prioritize, and navigate organizational politics.
   • They also have chapters in Los Angeles and San Diego, among 20+ cities, which could be useful if you're in Southern California.

2. Chief of Staff Association — best for professional development

   • A more formal global professional association spanning 75+ countries.
   • Stronger emphasis on structured education, research, mentoring, executive education, and its Certified Chief of Staff credential.
   • Its member resources include journals, research reports, templates/frameworks, recordings, and practical resources.
   • I'd especially consider it if you're thinking of CoS as a long-term career, rather than just a role you're trying out.

3. First Round Review — best free reading

   • Not a CoS community per se, but excellent for the skills that matter: executive communication, organizational design, operating cadence, hiring, management, decision-making, and working with founders.
   • Search specifically for pieces on founder/CEO relationships, operating systems, strategic planning, and executive teams.

4. LinkedIn — surprisingly useful if you curate it

   • Follow experienced Chiefs of Staff rather than relying on generic “Chief of Staff” groups.
   • Look for people who have been CoS at companies similar to yours and study how they describe their operating models.
   • A particularly effective tactic: send a short note asking another CoS for 20 minutes to compare notes on the first 90 days. CoS people tend to understand the unusual nature of the role immediately.

5. Executive/Operator communities

   • Depending on your company stage, communities around operations, strategy, startups, or executive leadership can be just as useful as CoS-specific groups.
   • This is especially important if your role is really a hybrid of CoS + BizOps/strategy/operations.

Resources I'd bookmark

• CoS Network research & playbooks — practical material specifically written for the role. Their current programming includes a Launchpad for aspiring/first-time Chiefs of Staff and Power Skills training.
• CSA resource library — research, journals, frameworks, templates, and recordings.
• CoS Network podcast — useful for hearing how experienced Chiefs think about the job rather than just reading frameworks.
• HBR — particularly material on executive teams, influence without authority, decision-making, organizational alignment, and strategy execution.
• First Round Review — particularly strong for startup/founder environments.

If I were starting the role tomorrow

I'd do three things immediately:

1. Join CoS Network's free community.
You can get the newsletter, blog, podcast, research, and community exposure without committing to the paid tier.

2. Find 5–10 Chiefs of Staff who resemble your situation.
Same company stage, industry, CEO/founder profile, and scope. Ask them what they wish they'd known during their first 90 days.

3. Build your own “CoS operating system.”
Create a living repository containing:

• Principal preferences
• Key stakeholders
• Weekly operating cadence
• Decision log
• Strategic priorities
• Open/unowned problems
• Meeting templates
• Executive-team dynamics
• Important metrics
• 30/60/90-day observations

That last piece is particularly important: the best CoS resources won't tell you exactly what your job is. Your first major job is figuring out what the organization—and especially your principal—actually needs from you.

If you tell me what kind of Chief of Staff role you have (startup/founder, corporate executive, nonprofit, government, etc.) and roughly your company's size, I can narrow this to the 5 communities/resources I'd personally prioritize for your situation, including free vs. paid.

Stepping into a Chief of Staff (CoS) role can feel like operating in a one-person department , making external peer support and vetted playbooks essential.

The top online communities, networks, and professional development resources tailored for new Chiefs of Staff include:

• Chief of Staff Network (COSN): One of the largest global communities for CoS and senior operators. It features private Slack access, salary and compensation benchmarking data, global chapter events, and structured programs like the Chief of Staff Launchpad (a cohort-based certification) and Power Skills training tracks.
• Ask a Chief of Staff : A dedicated community and resource hub for current and aspiring CoS. Founded by Clara Ma, it offers a supportive Slack community, mentorship opportunities, video archives, and a robust template/resource library designed to help new hires navigate onboarding and executive alignment.
• Chief of Staff Roundtable : A professional development group led by Philip Burns that offers weekly expert-facilitated roundtables, member-led office hours, an extensive library of recorded sessions, and a 24/7 digital portal packed with field-sourced practitioner insights.
• Chief of Staff Collective (CoSC) : Founded by Ben Legg, this is a prominent, free community specifically geared toward Chiefs of Staff in entrepreneurial and scaling businesses. It features active peer discussion channels, virtual meetups, and best-practice sharing.
• The Chief of Staff Association (CSA) : A globally recognized organization offering structured competency programs, self-paced virtual modules, and executive education paths connected to top business schools. It emphasizes formal credentialing and cross-industry peer support.
• r/ChiefsOfStaff : An active, informal online forum where practitioners swap tactical automation tips, management frameworks, and real-world advice on handling the isolation of the role.

Would you like help focusing on tactical templates/frameworks (like executive meeting prep or OKR tracking), or are you more interested in finding a peer-group cohort?

If you’re a new Chief of Staff, I’d prioritize communities where experienced CoSs share the messy, practical stuff—executive dynamics, prioritization, decision-making, planning, and “how do I handle this?” situations—over generic leadership courses.

My top picks

1. Chief of Staff Network — best overall

   • Probably the first place I’d join.
   • Large peer community, private Slack, regional chapters, events, research, templates, training, and a job board.
   • They have a free Operators Community for aspiring/new CoSs and a paid professional membership with deeper peer support.
   • Especially useful when you have a very specific problem and want to ask, “How have other CoSs handled this?”

2. Chief of Staff Association — best for peer learning

   • Strong international network with online programming and peer groups.
   • Its Circle of Influence groups are particularly interesting for working through challenges with other Chiefs of Staff.

3. Chief of Staff Academy — best for structured onboarding

   • Offers a CoS Primer, webinars, tools/templates, coaching, and a dedicated First 90 Days program.
   • Good if you're thinking, “I understand the job conceptually, but I need a framework for actually starting.”

4. Reddit — r/ChiefsOfStaff — best informal/anonymous perspective

   • Surprisingly useful for candid discussions about the role, books, executive relationships, compensation, and career transitions.
   • A recent thread, for example, had CoSs recommending The First 90 Days, Chief of Staff by Tyler Parris, and other practical leadership books.
   • The advice is less curated, so treat it as a source of perspectives rather than gospel.

5. The First 90 Days by Michael Watkins — best foundational book

   • Not CoS-specific, but exceptionally relevant when entering a new role.
   • The framework focuses on accelerating your transition, diagnosing the situation, securing early wins, and building the right relationships.

A few other resources I'd put on the radar

• Chief of Staff Network's podcast/research — useful for hearing directly from practitioners and understanding how the role is evolving.
• Chief of Staff Network local chapters — particularly valuable if you want relationships beyond online discussion; they currently list chapters across 20+ cities.
• LinkedIn — follow experienced CoSs and the dedicated CoS organizations, but use it more for finding people to learn from than for consuming generic “leadership content.”

If I were starting the role tomorrow

I'd do three things in parallel:

1. Join a peer community.
Start with the Chief of Staff Network's free community, then decide whether the paid network is worth it after you've identified your actual needs.

2. Read The First 90 Days.
Use it as the skeleton for your onboarding plan rather than simply reading it cover-to-cover.

3. Build your own informal “CoS board.”
Find 3–5 experienced Chiefs of Staff who are in somewhat similar environments and establish occasional 30-minute conversations with them. This can become more valuable than almost any course.

The biggest mistake I'd avoid is trying to become a generic excellent executive. The CoS role varies enormously by CEO, company stage, and mandate. Your highest-value learning will come from people who have dealt with your particular version of the job.

If you tell me whether you're a CEO/Founder CoS, corporate CoS, political/nonprofit CoS, or a first-time CoS at a startup, I can narrow this down to the 5–10 resources I'd actually spend time on, including specific books, newsletters, podcasts, communities, and courses.

Stepping into a Chief of Staff (CoS) role can feel isolating because you are often a "department of one" acting as the connective tissue for leadership. Joining a dedicated peer community provides templates, sanity checks, and accelerated learning.

The top online communities, networks, and resources tailored for a new Chief of Staff include:

• Chief of Staff Network (COSN) - Widely considered the leading global professional organization for the role. It offers a robust Slack community, local city chapters, specialized development tracks (like their Launchpad and Fundamentals courses), and an extensive knowledge hub filled with member-generated playbooks and frameworks.
• Ask a Chief of Staff - A curated, highly supportive community focused heavily on mentorship, asynchronous Slack discussions, and virtual educational workshops. It is a fantastic environment for new or aspiring CoS to find a mentor and share day-to-side-day operational hurdles.
• Chief of Staff Association (CSA) - A massive global association spanning over 75 countries and multiple sectors (corporate, non-profit, government). They provide a dedicated global Slack workspace, international summits, and high-level academic partnerships (offering programs tied to institutions like Oxford and Harvard) for formal professional credentialing.
• Chief of Staff Roundtable - A private peer network built explicitly for newer and growing practitioners. They focus on clarity and confidence through weekly expert-facilitated roundtables, bi-weekly office hours, masterminds, and a massive digital library of archived tactical sessions.
• Chief of Staff Collective (CoSC) - A fantastic free community geared primarily toward operators in entrepreneurial and scaling businesses. It features a private Slack channel and regular meetups to crowdsource solutions for OKRs, planning, and software choices.
• The Chief of Staff Podcast - Hosted by the founder of the Chief of Staff Network, this show features raw, tactical interviews unpacking the unwritten rules, hard lessons, and operational frameworks used inside top companies.

If you'd like, let me know:

• What industry or company stage (startup, enterprise, non-profit) you are in
• Whether you are looking for free vs. paid/vetted memberships

I can recommend the exact community tier that fits your current focus.

If you’re a new Chief of Staff, I’d prioritize communities where you can learn from people actually doing the job—not just generic leadership content. The role is unusually context-dependent, so peer pattern-matching is incredibly valuable.

My top picks

1. Chief of Staff Network — best overall

   • Probably the best starting point for a corporate/startup CoS.
   • Has a free Operators Community plus paid communities, peer groups, events, research, a podcast, job board, and training.
   • Its professional membership includes private Slack, regional chapters, peer connections, and events.
   • Best for: day-to-day questions, benchmarking your role, networking, career development.

2. Chief of Staff Association — best for structured professional development

   • A more formal global professional association, with members across 75+ countries.
   • Offers competency programs, mentoring, events, research, journals, and a substantial resources library with frameworks and templates.
   • Best for: developing the actual craft of being a CoS and building a long-term professional network.

3. r/ChiefsOfStaff on Reddit — best informal/community perspective

   • Smaller and less polished, but useful precisely because people discuss the messy realities of the role.
   • Recent discussions include recommendations for training, peer roundtables, automation, and developing leadership presence.
   • Best for: “Has anyone else dealt with this?” questions and candid perspectives.

4. Chief of Staff Network podcast + research

   • Even if you don't join the paid community, I'd consume the Network's podcast, research reports, salary research, and articles.
   • The Network says it has 30,000+ subscribers and publishes research based on experiences of practicing Chiefs of Staff.
   • Best for: getting a vocabulary for the role and understanding how other companies structure it.

5. Chief of Staff Roundtable

   • Worth investigating if you want a smaller, discussion-heavy peer group rather than a large professional network.
   • Recent CoS community members specifically recommended it as a place to bring real problems and learn from other Chiefs of Staff.
   • Best for: peer problem-solving and relationship building.

A few resources I'd add to your reading stack

• Paul Cohen's Chief of Staff Guide — particularly useful for thinking about how to shape the role and avoid common pitfalls. It was also highlighted in the CoS community's resource roundup.
• Maggie Hsu's Chief of Staff writing — especially good for understanding the corporate CoS role, first 90 days, and best practices.
• Emily Sander — her book, podcast, and newsletter are frequently recommended by practicing Chiefs of Staff.
• Harvard Business Review — useful for the executive-leadership side of the job, though I'd supplement it with actual CoS communities.

If I were starting the role tomorrow

I'd do this:

Week 1: Join the free Chief of Staff Network community and subscribe to its newsletter/podcast.
Week 2: Join or at least explore CSA and its resources.
Week 3: Find 5–10 Chiefs of Staff at companies roughly your size/stage and ask for 20-minute conversations.
Ongoing: Keep a private “CoS playbook” with templates for executive meetings, decision logs, weekly updates, stakeholder maps, operating cadences, and lessons learned.

The biggest thing I'd emphasize: don't optimize for consuming more content. Optimize for building a peer network. The most valuable CoS knowledge tends to be tacit—“Here's how I handled this CEO disagreement,” “Here's how I got the leadership team to actually use the operating cadence,” “Here's what I wish I'd clarified with my principal in month one.” That's exactly where communities outperform books and courses.

If you tell me whether you're a startup CoS, Fortune 500/enterprise CoS, nonprofit/public-sector CoS, or CoS to a founder/CEO, I can narrow this to the 5 resources I'd actually spend time/money on for your specific situation.

As a new Chief of Staff (CoS), you often operate as a "one-person department" without an obvious internal peer group, making external communities and curated toolkits essential for sanity and success.

The top online communities, networks, and resources tailored for new and aspiring Chiefs of Staff include:

• Chief of Staff Network (COSN) — One of the largest global communities for the role. They feature a free "Operators Community" for generalists , structured learning programs like the Chief of Staff Launchpad , masterclasses, and a thriving Pro membership with active Slack channels, templates, and local city chapters.
• Chief of Staff Roundtable — A peer-based network and digital portal boasting thousands of practitioners. It offers weekly expert-facilitated roundtables, bi-weekly office hours, curated 1:1 peer introductions, and an extensive library of recorded sessions and frameworks.
• The Chief of Staff Association (CSA) — A massive global membership organization spanning corporations, non-profits, governments, and healthcare. It offers specialized credentials (Certified Chief of Staff), a dedicated global Slack workspace, executive education pathways (with partners like Oxford and Harvard), and regional chapters.
• Chief of Staff Collective (CoSC) — A free community aimed primarily at entrepreneurial and fast-growing businesses. It provides a private Slack channel, informal meetups, and real-world peer brainstorming on operational or strategic hurdles.
• Ask a Chief of Staff — A supportive community focused heavily on mentorship, facilitated discussions, resume/transition advice, and curated template libraries built by experienced practitioners.
• Elevation Chief of Staff — Founded by executive coaches, this resource offers targeted certification programs and access to a private community ideal for new operators looking to master core mechanics like executive comms and off-site planning.

If you'd like to narrow these down, tell me:

• What type of organization are you working in (startup, enterprise, non-profit, etc.)?
• Are you looking more for tactical templates (like meeting agendas or OKR frameworks) or peer mentorship?

I can recommend the exact community or specific resource tier that fits your current mandate.