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Staying connected—and strategically consistent—in a remote workplace: A look at Skillshare's operating cadence
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Staying connected—and strategically consistent—in a remote workplace: A look at Skillshare's operating cadence

The weekly, monthly, quarterly, and annual meeting cadence Skillshare uses to achieve alignment and business results.
Skillshare approaches its work culture just like its product—always testing and iterating to determine what works and what doesn’t. In 2019, and emphasized that I was describing our processes captured as a specific moment in time. Just as we did then, our leadership team consistently meets to update Skillshare's processes as the company grows and priorities change. And when Skillshare transitioned to a remote workplace in 2020, meeting cadence and team engagement remained vital to keeping Skillshare connected.
The focus of this doc is how we run Skillshare now—and gives you every tool you need to adapt our processes to your team. Watch as I walk through our operating cadence, and then read on for the changes we’ve made over the past two years.
Problem: Operating a high-growth business in 2021
Skillshare was founded ten years ago and has grown tremendously over the years. As a high-growth business, we have to continually evaluate our processes and operating cadence. In other words, the processes that worked for us as a startup ten years ago are different than those driving the strategic goals of our 500+ employees.
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The problem is that you need to plan for these future process changes today even if everything is running smoothly right now. And doing so involves meeting with key cross-functional stakeholders to see what challenges they face and what resources they need for near and long-term.
Keep in mind that our current operating cadence may not work perfectly for your organization. I hope that our model acts as a template you can build off of and mold for your own organization.
Solution: Consistent and predictable processes in a fast-changing environment
This solution may sound counterintuitive, but providing some sort of consistent and predictable operating cadence helps our team stay on track to hitting their goals.
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Yes, things get messy sometimes, but everyone at Skillshare understands that things may not go as planned. It’s ok to veer off our plans if need be. Skillshare is such an amazing organization because we can stay nimble and have a structured operating cadence as a north star.
Goal-focused adaptation
No matter how our operating cadence evolves, changes are grounded in 3 goals.
Consistency of operations: We should be confident in the direction Skillshare is heading.
Consistency of strategy: Being distracted by the newest, shiniest approach to an old problem is hard to avoid. We’ve found success in scheduling breathing room between big-picture strategic decisions. And we spend that time thinking, researching, and debating potential strategy shifts.
Balancing short- and long-term: There are opportunities to be missed in thinking too far ahead and not far enough ahead. We try to shine lights on both short- and long-term goals, when they need it. We want to recognize both opportunities and threats early, and then have an established process for determining how we will respond.

The easiest way for you to get started with an operating cadence at your organization (no matter the size) is to categorize each of your operating processes into annual, quarterly, monthly, etc. buckets.
Skillshare’s operating cadence
We’ve established a set of annual, semi-annual, quarterly, monthly, weekly, and bi-weekly rituals to drive our goals and establish predictability around our decision-making processes. Expand each header to learn more or click the header to go straight into the the templates.
We start initial planning for the following year in Q4. Our approach to annual planning combines bottom-up input from the entire team and top-down structure and guidelines from the management team. The bottom-up approach gives us a broad base of input from which to decide our direction for the coming year and builds consensus among the team, but the challenge is driving alignment and making sure the strategy is cohesive. A top-down approach ensures alignment, but makes it harder to get buy-in from the broader team and potentially misses valuable ideas and input from those closest to the action.
Performance reviews are held twice a year: a 360 peer review with compensation assessment and a mid-year check-in. Managers should be giving regular feedback without waiting for a review cycle, so feedback given during a formal review shouldn’t come as a surprise.
Our culture is very important to us, and we invest a lot of time and resources into improving how we work together. Every year we run a full engagement survey through CultureAmp, and the resulting data gives us a feel for where we are doing well as a company and where we can improve. It also provides us with a benchmark to see how that feedback is changing over time, as well as compares us to an index of companies at a similar size and stage of growth. While our absolute numbers are generally very good compared to the competitive index, we try not to focus too much on the actual metric and think more about the trends and hotspots we can address.
We develop our OKRs on a semi-annual basis, primarily as an alignment tool. So, Company OKRs > Department/Team OKRs > Individual OKRs. We typically have 3–4 company-level OKRs, and then each department creates more specific OKRs that roll up to the company level goals, and then individuals roll up to departmental.
A consistent challenge for every business is helping employees understand why their work matters. We use OKRs to create a very clear line from the individual goals to the overall company goals so it is clear why their work matters.
At the end of the month following the end of the calendar quarter, we run a Quarterly Business Review (“QBR”) instead of our normal weekly town hall or monthly all-hands meeting. In the QBR, we typically block out a half-day to review our progress over the last quarter and discuss our updated plans and priorities for the quarter ahead. The goal is for it to serve as a check-in point, where we pull back from the day-to-day to make sure we’re still all pushing toward the same strategic goals and reassessing what is working and what’s not. We then do a half-day fun activity, typically getting out of the office for some team building. About 20% of our team is distributed so we try to fly each remote team member in for a QBR at least twice a year.
At the end of every quarter, the product and engineering pods update their quarterly roadmaps. The product roadmaps are always flexible — we can make adjustments at any time based on what we are seeing day-to-day. That said, we use a quarterly refresh to take a deeper look at what we’re building and where we are putting our engineering resources.
Once a month, typically on the last Friday of the month, we hijack the weekly to review our financials, key metrics, and initiatives. As somewhere between the Town Hall and a full QBR, this meeting is a checkpoint between our QBRs and gives us another opportunity to share wins and address any issues that have come up. We include a segment of ‘Ask Skillshare Anything’ so that the team can surface any open questions they have, regardless of the topic.
Once a month, we ask the team to go update OKRs. We are looking for a quick update, not a full-blown report, so this should not create a lot of overhead for the team.
Every week or two, each team has a departmental meeting to share information, drive alignment, and address any operating issues. These are often large meetings and very expensive from a $-per-hour basis, so they need to have a clear objective, defined agenda, and be run efficiently. A key part of an efficient meeting is assigning a note-taker to capture decisions, open questions, action items, follow-ups/next steps, etc.
Every Monday afternoon, the management team and key departmental stakeholders meet to discuss our core weekly metrics and progress toward our OKRs. The goal of this meeting is to share progress and identify any new opportunities or problems early so that we can get ahead of them. We have a dashboard that has the key business metrics, and then a shared doc where we review departmental progress toward our OKRs. It is a good opportunity for the attendees to hear what is going on in other departments and get feedback on their own initiatives.
The management team has 2 meetings per week. The first is right after the BizOps meeting, and it is our ‘Flex Agenda’ meeting. The goal of this meeting is information sharing and alignment, and we often surface issues that need more attention or a longer conversation. Each member of the management team can drop in agenda items to cover any issues where they need to share an update, get quick input, raise a potential topic for a deeper dive, etc. These items should be quick — 5 min or less — and if the conversation starts to drag on we at least attempt to move it into a separate meeting or add it to the agenda for our Wednesday strategy meeting.
The second meeting every week is the strategy meeting on Wednesday mornings. We take a deeper dive into bigger topics, with the goals varying from information sharing to decision making to innovation. The exec team and a few key departmental leads are consistent attendees, but we invite other team members based on the topic we are discussing. We have tried the , but it just didn’t work that well for us. Personally, I like the format a lot and still write memos or outlines just to organize my own thoughts, even if they never see the light of day. But after pushing it for a while, it just didn’t stick so we went back to the presentation model.
Every manager holds a 1:1 with his/her direct reports at least once every two weeks; we leave it to the manager whether they want to do them weekly or biweekly. The two should have a shared document where they set the agenda for each meeting and capture any notes or action items.
These meetings should be primarily driven by the direct report, not the manager — what progress have you made toward your goals, any issues that you need help addressing, where your priorities lie for the coming weeks, etc. I still like a model I stole from Gary Swart at oDesk (and I assume he took from someone else) — the “4Ps”. They are Plans (your quarterly goals, you recap them every week), Progress (how you moved things forward since the last meeting), Problems (where you are stuck or need help) and Priorities (where you are focused next). The manager should bring any open questions or concerns she/he has, but most of the agenda should be set by the direct report.
Often 1:1s become status update meetings, and we recommend you use the shared document to cover those items in advance. A recommended cadence would be the direct report shares an updated doc a day or two before the 1:1, with status updates on all key projects and the agenda of items he wants to discuss. The manager then has time to read through the status updates before the 1:1, leaving more time for discussion of the agenda items.
This is our standard weekly all-hands meeting, and the primary goal is information sharing. The standard agenda is:
Business metrics: We highlight progress toward the top 1–2 metrics for the company
What management is thinking about: We can share anything that is top of mind that we want you to be aware of or thinking about as well
Spotlight: We typically present a new product feature or new Skillshare original that we want the company to be aware of (and celebrate)
Housekeeping/announcements: Our opportunity to cover any of the day-to-day details — holidays, office issues, upcoming meetings/events, etc

When we were smaller, we had a dedicated segment for Shout Outs, giving the team an opportunity to recognize each other publicly. It became unwieldy as we grew, so we moved it to a Slack channel for ongoing recognition and celebrating wins, both big and small.
Design an operating cadence that works for your company, with this doc.
This operating cadence works for us, at this moment, but it may not work for your business, team, or culture. This is a snapshot of how we run today—we are constantly updating. And our adjustments will never end, because what worked at 30 employees doesn’t work today, and what works today won’t work in five years. There will always be a need to update, refine, and progress how we operate to make sure we are meeting the needs of the company and the employees.
The important thing is that you are deliberate in your approach, and consistently step back and reflect on what’s working and what’s not. Have suggestions or ideas we should consider? We’d love to hear from you!
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