Issue 40: Creating Great Remote Company Culture as a Chief of Staff
The "C" in CoS stands for "Culture"
Welcome back, aspiring and current Chiefs of Staff 👋🏼
In this week’s issue, we’re featuring a guest post from Jared Kleinert, Founder/CEO of Offsite. Offsite is the “go to” resource for any Chief of Staff planning a team retreat. They offer a curated marketplace with hundreds of offsite venues, all at 2️⃣ 0️⃣➕% discount for room blocks and meeting space, plus end-to-end offsite planning services for teams of 1️⃣ 0️⃣ to 5️⃣ 0️⃣ 0️⃣ attendees.
Click here to make a free Offsite account (no credit card required) and submit your first request for a spectacular offsite venue in a matter of minutes. And if you plan an offsite in April using our product, Offsite will give you up to $1000 off when you mention “Ask A Chief of Staff.”
Disclosure - I’m an angel investor in Offsite, but only because I wish something like this existed when I was a Chief of Staff planning team retreats at Hugging Face and AngelList!
*Interested in sponsoring a future issue of Ask a Chief of Staff, hit reply.
If you’re reading this, you are likely already a Chief of Staff at a remote/hybrid company, or you are an aspiring Chief of Staff and want to work remotely if possible.
Given that one of the most important roles of a Chief of Staff is to increase employee engagement, retention, and alignment, Clara asked me to share some “pro-tips” on building great company culture especially for remote and hybrid teams.
My company, Offsite, supports hundreds of the world’s top startups, VC firms, and Fortune 1000s (most of them remote-first or hybrid) with team retreat planning, which is one of the most important cornerstones of culture-building for remote/hybrid teams.
Without further ado, let’s discuss various ways you can create great company culture at a remote or hybrid company.
🔭 Refine Your Company’s Mission, Vision, and Values
Your company’s mission is ultimately what you’re selling to your team. Why should they join you on your company’s journey? Are you planning to make humans a multiplanetary species like SpaceX, save the planet like Patagonia, or spread ideas like TED?
Your mission statement is an opportunity to “rally the troops” whereas your Vision is the initial phases of this plan (ie the “How”). For Tesla, the Vision was to create an expensive car, then a mid-level car, and finally an affordable vehicle everyone could afford. For Amazon, the Vision was to sell books online, then expand into other categories.
Your Values are the habits, principles, and guidelines by which you execute your vision. For every company, this will be different. Less is more with company values, and they should be practical, so that everyone knows how to act when you’re not looking. Famously, Meta had an old value of “move fast and break things” which helped employees prioritize speed over perfection.
On The Offsite Blog, you’ll find a helpful webinar diving into these topics more closely should you wish to explore this further.
📝 Document Everything and Encourage Async Communications
With an increasingly global workforce, building a culture of documentation (and teaching your team about effective async communication habits) is going to become “make-or-break” to company culture.
Embracing tools like Notion for process documentation is not just about maintaining a knowledge base—it’s about architecting a scalable infrastructure that empowers every team member with the knowledge they need to drive forward. If you want to take PTO or parental leave, or suddenly scale up and hire dozens of people at once, your documentation will allow everyone at the company to quickly step into any role.
In order to keep everyone focused on “deep work” and also navigate multiple time zones without asking employees to work crazy hours, adopting asynchronous communication habits is key. Tools like Loom can help you and others convey nuanced, comprehensive ideas without the constraints of real-time scheduling or meeting on Zoom. Plus, Looms can be transcribed and turned into documentation!
The tools matter less than the habits you’ll need to encourage among your team. The best tool is the tool that your team will use. The important thing is to document important processes, teach everyone how to communicate effectively without having to schedule real-time meetings, and developing a company wiki that can help you with onboarding, training, and company-wide communications over time.
🕰️ Create A Predictable Rhythm of Business
It pays to establish rituals around goal-setting, reporting to investors, and investing in your company’s culture. Having daily, weekly, monthly, and quarterly “rhythms” keeps the business moving forward, and you can start with the basics before adding in other motions.
This is especially important for remote/hybrid teams where colleagues may work across multiple time zones, won’t see each other often in-person, and must be self-starting in their approach to work.
Daily: Standups
Should you have an office-first culture, this might be a literal “standing” meeting, where everyone shares what they accomplished yesterday, what they are working on today, and what’s blocking them or where they need help.
As a remote-first company, you can use a tool like Geekbot (which integrates with Slack) to facilitate this exercise.
Weekly: All-Hands Meeting, 1-on-1s, and Company Scorecard
As a founder/CEO, every Monday I meet with my direct reports and encourage them to do the same with their teams. These “1-on-1s” are about them, not me, and give my direct reports the space to share where they need help, what’s going well, and what potential landmines we’re moving towards. I also typically ask how everyone’s weekends were, and ensure I’m meeting people “where they are at” given whatever is going on in their personal lives.
We also have a 30 minute “All-Hands” meeting where leadership briefly runs through major company updates by department. We also start each meeting with a quick share of gratitude and a fun icebreaker so we can get to know each other a little better each week. Finally, we share the top 5-10 metrics being tracked so we know if we’re achieving our OKRs or not.
Quarterly: OKRs, Board Meetings, and Offsites
Each quarter, we pick 2-4 company-wide “objectives” as well as 3-5 “key results” that would indicate whether we accomplish our objective or not.
If we want to increase margins, for example, then one key result might be to raise prices by 10%. Another might be to reduce our Cost of Goods Sold by 20%. We use our key results to figure out how everyone will contribute to accomplishing company-wide goals.
We also plan offsites quarterly with our leadership team and twice per year with the entire company. Depending on whether you are remote-first or office-first, and how large your team is, will dictate how often you should plan team retreats. However, at minimum your leadership team should meet for 2 full days each quarter, outside of the office (if you have one) and at a destination where space is cleared for strategic planning.
🏕️ Why Offsites Are So Important
If you are remote-first, you should also plan 2-4 all-company offsites per year to increase employee engagement, retention, and alignment by including them in strategic planning efforts, reiterating company Mission, Vision, and Values, and celebrating your success along the way.
One of the best ways to leverage offsites for employee retention, engagement, and alignment (especially for remote and hybrid teams) is to develop a regular cadence for offsites.
These should not be one-off experiences. They should be predictable so you can plan in advance, utilize feedback from previous offsites to make future experiences better for your team, and increase the ROI on each offsite you host.
With a regular offsite cadence, you and your principal can also plan for the appropriate staff to take on this responsibility in the future, whether you continue to plan offsites but reduce scope in other areas of your job description, bring in other team members to support you, or choose to outsource offsite planning to a trusted resource like Offsite.
For pioneering remote-first companies like Buffer, Automattic, Zapier, Basecamp, 15Five, Atlassian, and others, offsites have been touted as pillars for building exceptional company culture. It makes sense - if you are remote or hybrid, offsites may be the only times of year your colleagues will see one another, meet new team members, and recommit to your company’s trajectory.
Ready to plan an offsite for strategic planning, mission/vision/values setting, and engaging your amazing team? Offsite.com makes it easy by saving you time, money, and stress whenever you plan a team retreat, conference, or offsite. Choose between the firm’s Airbnb-style marketplace and save over 20% on hundreds of boutique offsite venues globally or use its end-to-end offsite planning services.
Click here to learn more or reach out to jared@offsite.com. If you plan an offsite in April using Offsite, we’ll give you up to $1000 off when you mention “Ask A Chief of Staff.”
🎥 Upcoming Events and Workshops:
April 23rd: Leveraging Generative AI as a Chief of Staff
April 25th: Coffee and Co-Working at Industrious (NYC, in-person, free for all to attend)
April 26th: CoS Virtual Coffee Mixer: #3 hosted by Ask a Chief of Staff, Nova Chief of Staff, Ambient (Free for all to attend)
April 29th: Landing a Chief of Staff Role
May 10th: Volunteering at Battery Park City (NYC, in-person, free for all to attend)
August 7th-9th: First Ever Ask a Chief of Staff Summit 📣 📣 📣
As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.
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Love this! Offsites also encourage teams that haven't worked together during the quarter to interact organically and find ways to collaborate that can strengthen the company overall.