YC Alum Advice for Managing Remote Teams

We hosted a virtual panel with YC alum on best practices for managing a remote team. We aggregated the advice shared by alum, including Sid Sijbrandij & Darren Murph of GitLab (remote team of 1,200+), Wade Foster of Zapier (remote team of 300+), Ian Tien of Mattermost (remote team of 100+), Nick Raushenbush & Finbarr Taylor of Shogun (remote team of 60), Rajiv Ayyangar of Tandem (remote team of 6) and more.

Here is advice from the YC community:

Question: Can you share any playbooks on how to quickly transition a team to remote?

Recommended playbooks and resources:
Remote work emergency plan: What to do (and where to start) (GitLab)
Remote work starter guide for employees: how to adjust to work-from-home (GitLab)
What not to do when implementing remote: don’t replicate the in-office experience remotely (GitLab)
The Ultimate Guide to Remote Work (Zapier)
Remote Work Guide (Shogun)
Transitioning to remote work in a hurry (Zapier)
Mattermost Handbook: Company Communications (Mattermost)
19 Foundational Tips for New Remote Managers (Olark)
3 Pillars of Building a Remote Team (Shogun)
The Future of Work (YouTeam)
Running a Remote Team for 7 years (SketchDeck)
Influencing Virtual Teams: 17 Tactics That Get Things Done with Your Remote Employees

Nick Raushenbush, Shogun: Here are the tools that we use on a daily basis:
Slack: For communication that is fast moving and somewhat ephemeral.
Ally.io: For objectives and key results (OKRs); quantitative goals are really important when it comes to remote teams and should be a team member’s northstar.
Notion.so: For permanent information, like our company’s wiki/ knowledge base.
Zoom: For synchronous communication.
Donut: For onboarding and remote socialization; Donut integrates well with Slack.
CloudApp: For communicating in annotated screenshots GIFs, and short videos. Sometimes a written explanation doesn’t suffice, but it’s not quite worth a call.
360 Learning: For scaling knowledge for business development and support; this tool enables you to create videos, turn transcriptions into written posts, create quizzes and peer-to-peer learning programs. Lessonly is a good alternative as well.
Rev: For transcribing video or voice into text. Much of remote communication is asynchronous; this is a nice hack for creating written content and transcribing meetings.
Loom: For video recording communications, creating tutorials, trainings, etc.

Question: I have a lot of experience working remotely, and I’m looking for a job. How do I find a remote position?

Question: What is the right cadence of check-ins? Not just for my executive team but for managers and their teams?

Wade Foster, Zapier: I’d keep in mind task relevant maturity (a concept from Andy Grove’s book High Output Management). When someone is good at something, you can go longer without check-ins. When someone is new to something you probably want more frequent check-ins. If my team was new to remote, I’d probably start with an AM and a PM check-in; then as we get more comfortable and have less frequent blockers, I’d scale the check-ins back.

What we do at Zapier:
– Weekly: 1:1s, Staff Meetings and All Hands
– Monthly: OKR Reviews, OKR Planning

Ian Tien, Mattermost: If your team is international and across multiple time zones, here is a detailed handbook outlining how to approach company wide communication. To start off, it is important to record meetings and take anonymous Q&A feedback asynchronously, so if someone is not able to attend they are still on equal footing to interact.

Nick Raushenbush, Shogun: When we were a smaller team we relied on ad hoc communication a lot more. Now we are more thoughtful with meeting structure. Monthly: Company-wide AMAs are a new thing, but so far we really like them. We’re planning for once a month but might drop to once a quarter based on feedback. Weekly: Team fireside chats for 30 minutes.

During meetings and check-ins I always ask:
– How are you doing and feeling this week?
– What are your blockers?
– What can I do to empower you to hit your goals?
– Do you need time, budget, human resources?
– Do you see any systemic issues/problems with how the company or product are functioning?
– Any questions for me?

Question: What do you do to keep culture alive when fully virtual and remote?

Ben Congleton, Olark: It starts with empowering your team to have space to think about the culture and values they want to present. Here are guides that we put together:

Rajiv Ayyangar, Tandem: We interviewed 100 remote teams and wrote a rundown of tactics for building trust: How to Build Psychological Safety in your Remote Team.

Nick Raushenbush, Shogun: Culture forms! Donut is a great tool to introduce team members to each other.

Question: We all know tools are important for remote work? How do you get people to actually use them?

Darren Murph, GitLab: If you’re forced to be remote, minimize your tool stack; minimize the chaos. It’s a lot for people thrust into remote areas, so if you can avoid introducing a new tool at the same time, avoid that. If you must do it, create documentation first, so the tool roll-out happens only after people have read, end-to-end, why you’re doing it, how they’ll use it, what it replaces, etc. Documentation is critical to adoption.

Ben Congleton, Olark: It is important to recognize that some business tools are critical while others are elective.The only tools that are company wide requirements are based on job function and team needs. For example, expectations are set around using Slack, Google Docs, Google Calendar and Zoom. Letting teams choose platforms and make tool decisions helps and benefits them directly.

Wade Foster, Zapier: We don’t enforce tool usage all that tightly outside of Slack and Zoom. What we do have is expectations on reporting. So if you reported to me, we’d agree on output at the beginning of the week, and at the end of the week, you communicate the result. The tools are a means to get to that — use whatever helps you get it done.

Question: What is the most important rule to follow as a remote team?

Yura Riphyak, YouTeam:It is extremely important to put everything in writing. Three reasons why:

  1. The written form disciplines thought and forces you to keep it short.
  2. All communication gets saved with no extra effort. This proves vital in case you need to involve more stakeholders in the future or revisit decisions that have been made.
  3. Textual content is searchable. Yes, you can record Zoom meetings — but how many of those recordings will you actually watch?

Question: What do you think about increasing peer 1:1 interactions?

For example:
When assigning a project, the manager also assigns a peer to discuss/help at the start, middle, and end of the project (vs full pair programming/working).
Encourage people to post office hours and list topics they’d like to help others do or learn.
Encourage or facilitate video chat amongst peers.

Yura Riphyak, YouTeam: Like most of the other things about non-work communication, we are trying to be light on any kind of management-induced activities. This stuff should happen bottom-up, not top-down. People who work remotely develop a comparatively high level of self-sufficiency and also a strong sense of personal space. One thing we are doing is making sure everyone knows about the others’ hobbies and interests. For example, we have a chess group, skiing group, and book club.

Rajiv Ayyangar, Tandem: At Tandem, we built rooms to allow for a virtual water cooler. Social proof (seeing that other people are talking) is a huge factor in whether teammates are willing to talk socially. A few factors that one could consider: Fun! If there’s a fun reason to talk, like a game you want to try or an icebreaker topic, that can help. Inviting vs. demanding. If you let people know you have office hours, or will be in a room/call during X-Y time, then it’s an invitation. If you say you’ll be video-calling random people, it’s demanding.

Via Y Combinator.