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

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, COO Sabrina Kieffer and I consistently meet 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.
The problem is that you need to
plan for these future process changes
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.


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
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
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.

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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