CoS Slack Threads

My friends Cassie and Shre are building Tripsha to help companies and communities to organize offsites and retreats. They're currently leading a Crypto Summer Camp in Puerto Rico

Also recently mentioned in the NYT.

Blurb below in case you / your company might be interested!

Tripsha makes it easy for companies and communities to organize manage company/team offsites and retreats. Tripsha makes it easier to make your offsite concept come to life and less time-consuming thanks to our purpose-built platform and a team of travel experts who can provide guidance and help to ensure your trip comes off without a hitch!

1-pager here and message Shre, the co-founder with any q's (shre@tripsha.com).

Great thread by Wes Kao on how succeeding as a generalist, detailing 11

disciplines to become a sharper operator 🔪

The 11 disciplines are here 👉

GREAT new piece by @ckeil titled: "How to find and crush a job as a startup Chief of Staff" 🙌

On doing the role well:

• While being a Chief of Staff will get you access into the Executive “room where it happens” and you’ll likely get some cool stretch opportunities, **you can’t go into the role expecting sexy, high-level responsibility to be the norm.
• To be a great Chief of Staff, you’ll have to operate at all levels of the organization: holding your own in executive conversations and efficiently cranking through a massive quantity of menial tasks.

What other takeaways from the post did you have? What else would you add? Let us know 👉

A really great onboarding overview by Regina Gerbeuax, who is CoS to Matt

Mochary (who spoke at the CoS Summit).

"If I had to break it down into several steps, I'd say criteria for success

looks something like this:

• Days 1-30: Become an extension of the way your CEO thinks

• Days 31-60: Become an extension of the way your CEO behaves

• Days 61-90: Become an extension of the way your CEO makes decisions "

How to onboard yourself in 5 steps:

1. Ask any and all questions.

2. Watch how they write.

3. See if you can start predicting the way they'll respond to questions,

comments, and concerns.

4. Document processes as you learn them.

5. Understand what fear, anger, or sadness look like in your CEO.

<https://mocharymethod.notion.site/Chief-of-Staff-How-to-onboard-yourself-

in-30-days-21e2cc3acfbf47d39f99d6ce902d3054>

Hi! I recently had a conversation with our COO where she explained to me that

when she was a CoS for her CPO (Product) she had very little face time with

her Principal, that they rarely spoke to each other, she did her work by

fulfilling tasks brought to her by his team, that there were no direct

meetings with the Principal and that CoS is an extremely subservient role and

to expect a similar experience for me as CoS to our CEO. This is the first

I’ve heard of a CoS described in this way and I’m wondering if this is

typical? Thank you for any input you can provide.

🥁 5 summaries and videos from the Chief of Staff are available now for you 🥁

1. Building the Executive Office 3.0

2. Uncovering Your Creative Potential with First Principles Thinking

3. Scaling Up! How to Expand Your Chief of Staff Role

4. Improving Operational Business Models for Scale

5. Chiefs of Staff Living in a Not Boring World

The 6 Steps To Being A Successful Chief Of Staff by Avery Blank in Forbes [Link]

1. Know the substance and how to operate.
2. Triage information to react and, at the same time, be proactive.
3. Establish a system that keeps you organized and enables communication with key players.
4. Develop a rapport with colleagues so you know who to go to and get things done.
5. Make decisions, and know when to escalate issues to your manager.
6. Seek feedback.

What would be #7 to you? Let us know! 👉

Hi all,

Curious to hear who has an EA within their company and what the scope of

his/her role is vs. CoS? E.g. is the EA role more secretary related or does

he/she also take over some of the responsbilities of the Cos?

Has anyone done any recent thinking / have any great resources on setting up effective (management) reporting into the CEO?

We’re growing like crazy and finding CEO isn’t getting enough information from certain areas of the business – so trying to create a framework for managers + c-suite to report key metrics and insights upwards

Question! My key focus for 2022 is building relationships with our leadership team (broadly defined, about 30 people), and I am looking for some structure or framework to guide those discussions until they become more regular and at ease. I am an introvert by nature, but can push myself (I was an elected official for many years!). I am in a new-to-me industry, so I tend to be shy in the unknown territory. My biggest objective for these meetings is to expand my principal’s reach, and equally importantly, ensure goal alignment and progression across the org. I dont want the conversations to start out transactional and focused just on the goals specific to their areas.

Any suggestions or frameworks for these 1:1s would be greatly appreciated. The cadence will vary across the team - some weekly, some bi-weekly, some monthly, some bi-monthly, some quarterly. Dependent on role/influence to corporate objectives. Thanks for listening/reading/suggesting!

A few asks for you all 😍

I’m recruiting a (1) CoS for our CTO, (2) People Culture Associate to

report to me (company CoS), and wondering if anyone has any of the following

to help guide me:

1. Your CoS job description that wildly attracted you to your role / one

that you thought was amazing

2. People Culture job description for an associate or manager

3. Recruiting process and/or interview questions for either roles that

you love

Review Self Assessment time! I’m stuck with how to respond to “What two

professional development goals do I want to accomplish in 2022?”

As a background: I’ve been with the company (tech startup 130 employees)

5 years and was promoted 1 year ago from a SR. EA to COS (no backfill no plans

to backfill) I’m supporting a team of 7 ELO members so I do a LOT. I’m

learning the ropes as I grow into the role (some changes include more

involvement with our Board, owning agenda, decks for our weekly ELO/leadership

meetings QBRs as well as being a more active participant, project management

with cross functional teams for weekly sprints related to our rally cry,

defining objectives, etc).

My Ask: With everything on my plate my honest response would be that I

want to grow into the role where I feel more comfortable and hit my stride so

that I can excel in it. How do I phrase this as a positive without committing

myself to taking on more work/responsibility/training/classes/etc?

Hi All -

Does anyone have thoughts on alternative titles to Chief of Staff? My

organization (Series A), is considering moving away from "Chief" titles to

"Head" titles inspired by this article - <https://blog.outschool.com/remixing-

titles/>. However, "Head of Staff" does not sound great nor is it

representative of a true CoS. I'd love any thoughts or ideas anyone may have!

Support Roles

We’re looking to hire essentially a “mini” Chief of Staff for each department

in our company.

We’ve stated that as a company, we’ll only have one CoS.

This role will do more than an EA and will support the whole department as

well as the executive. They’ll work on projects that need attention,

coordinating team events, scheduling for the exec etc..

My question is, what have you all seen this role titled as?

Here are some ideas we’ve come up with:

Idea #1. W/Career Progression Titles:

• Executive Assistant

• Executive Business Partner

• Sr Executive Business Partner

Idea #2. W/Career Progression Titles:

• Administrative Business Partner

• Business Support Manager

• Sr Business Support Manager

Thanks for your feedback!

have any of you guys put together a company wide strategy presentation -

getting to a 5, 10 yr roadmap that can be socialized with the company and to

get buy in from C suite? If so, any materials, or templates, structure that

you could share would be helpful. Thanks

Does anyone have recommendations on a format for investor updates? We're just

looking to revise ours currently.

What was an awesome All Hands you have done in the past 6 months? What was it?

Why was it aesome?

Hi All. It’s week 1 for me in the group and really looking forward to it.

I’ve been tasked to write a strategy paper and I wanted to check if there was

a resource to go to or a templates to share.

Hey all - does anyone have some examples of performance goals you've seen for

a chief of staff? Thanks!

Y’ALL can we talk about organizing slack channels? I recently put together a

comms guidelines document that’s been super well received but I’m feeling

paralyzed on making changes to our slack channel structure. generally, i know

we need to standardize our prefixes make our channels more specific b/c there

is info flying all over the place. Any best practices out there on a channel

audit or setup? Below was my first stab that didn’t get too much feedback from

the team….

Thanks in advance for the help!

Channel Clean Up

We have too many channels not enough channels depending on who you’re asking.

Either stems from a lack of purpose in the existing channels today.

• How do we generally want to organize our channels as a baseline?

• Channels dedicated for team members (daily grind/team comms)

◦ Pre-fix: #team _department

• “Catch All” General channels for each team

◦ How do we define this channel to keep it specific to the department but

general enough?

▪︎ General updates, announcements, questions from the ## department?

◦ Pre-fix: #general_department

• Specific channels

◦ Example: By existing potential product

▪︎ anything related to it like data, suggestions, user feedback, performance,

legal implications

◦ issue is:_ when do these get created? is it feature or product based? _

▪︎ What do we miss doing it this way? ex what specific channels get lost in

the noise?

◦ Other ideas besides by product? “Topic” seems too broad in scope?

◦ How when would we want supplementary channels? So we can identify prefixes

▪︎ Cross functional projects?

▪︎ Shared goals / tactics for goals ?

Hi Friends! Does your org have a framework for which decisions get elevated to the CEO and what role s/he plays in them? My CEO is out of office for two weeks and I am already feeling the weight of my execs being paralyzed by not having his input on their decisions.

Hi all. We are a fully distributed team of ~50 team members in 13+ countries. We had to cancel our IRL team retreat when Covid hit and had plans to go to Oceanside, California. We’re beginning to think about plans for a 2022 IRL retreat.

Does anyone have any location or accommodation suggestions? We’ll likely have somewhere from 60-70 team members when the time comes. We generally want to avoid anywhere that would be too difficult to get to, but we’re open to US or non-US locations.

Hi everyone, I am looking for some recommendations for two topics:

• cap table / stock option plan management services that cover Europe and the US, and

• company-wide benefits plans (healthcare, pension, etc.)

If anyone of you has recommendations, I would love to learn more. :slightly_smiling_face: Thank you!

hello! I’m helping our company think through how we can celebrate wins and people better, and acknowledge achievements. Curious what has worked well / not so well at your respective companies?

me again! does anyone gather and share company feedback/sentiment with their C-level? I have 1o1s with a number of folks across the org and have been asking how things are going, what we could do better, etc… and sharing with the execs. Wondering if anyone else has done something similar, and what structures you’ve used?

Hi all, curious if anyone has recommendations of how their companies approach taking a stance / making a statement either internally or externally on social issues. Sometimes there is a clear reason to speak out, but I am in the process of creating a rubric and playbook that helps the company decide when to speak out, what steps to take, and best practices to consider when the answer is less obvious. Specifically, I’m interested in your experience and recommendation of how your companies consider the “threshold” to warrant a statement/stance, Put another way, what constitutes materiality. Open to all thoughts and feedback, thank you!

hi all - does anyone have a good one-liner you use when introducing yourself on a call? like hi i’m chief of staff, and in my role I…..?

Has anyone organized a remote way to recreate the social / “getting to know each other” vibe of an in person happy hour? For your exec leadership team that’s distributed across country

Does anyone have any resources around hiring scorecards that would incorporate DEI? We're a small start-up and want to make it a priority from the beginning

hey all, any CoS's here that lead or are involved in your company's DEI efforts? I'd love to pick your brain on some topics like hiring, committee structures, managing expectations priorities, establishing metrics, etc.

Has anyone planned an exec level brainstorm on strategy and/or company okr’s?

Last minute planning something for next week with our c-suite and would value any guidance people have for frameworks we can use to ensure the time together is well-spent!

Hello! Does anyone have a standard format or template they share with teams for OKR setting? I created a simple Google Slide but would love to see other examples :slightly_smiling_face: Thanks!

hello, everyone - for recurring exec/senior leadership meetings, does anyone have a list of/some discussion topics that you and your execs/senior leaders find impactful and worthwhile to spend time on in live meetings? thanks so much!