How We Run Skillshare

Matt Cooper
Sep 20 · 11 min read
The Skillshare team in a recent design sprint

I have the opportunity to meet with other CEOs on a pretty frequent basis. I’m part of a CEO group in NYC that meets monthly for breakfast, attend a few other networking groups that meet several times a year, and each of our investors has an annual portfolio company meeting. A consistent topic of discussion and sharing of best practices is the cadence of how we run the business — annual/quarterly/monthly routines, planning, communications, check-ins, goal setting, etc.

The focus of this post is how we run Skillshare today. I want to emphasize today, as we regularly tweak and update our processes as the company grows and priorities change. Our founder, Michael Karnjanaprakorn, always said that we should work on our culture as we work on our product — always testing and iterating to determine what works and what doesn’t. Our COO, Sabrina Kieffer, and I spend a LOT of time talking through how to make tweaks and adjustments to everything below. We are contemplating changes to the structure below as I write this, so I’m going to type quickly.


Goals of our operating cadence

We have 3 goals in mind as we evolve our cadence:

  1. Consistency of operations: As we scale, it will become increasingly important that we are able to know where our business is heading. We hope that the processes below will drive consistency and predictability in how we execute.
  2. Consistency of strategy: Many high-growth and early-stage companies suffer from ‘strategy of the day’ syndrome, where there is always some shiny new approach to an old problem that feels easier and more exciting than the grind of whatever the company is working on today. We deliberately force some spacing between the big-picture strategic decisions. This spacing ensures that we spend a lot of time thinking about, researching, and debating any strategy shifts. Otherwise, we should be heads down executing the strategy and goals we’ve set.
  3. Balancing short- and long-term: If you are thinking too far out, you miss the issues right in front of you. If you are focused solely on what’s right in front of you, it’s easy to get off track and veer from your long-term strategy. By structuring how and when we focus on short- and long-term goals, we make sure that both get focus 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.

It is important to note that no process is perfect, and it is never as clean as it looks on paper. We are okay with it being messy at times, and there will be situations where we need to deviate from the routines and schedules below. However, enforcing consistency and predictability whenever possible makes everyone’s lives easier. There’s plenty of unpredictability in a high growth business, so we do what we can to be consistent and predictable in how we operate.


Annual and semi-annual routines

Reviews

We conduct our performance reviews twice a year. The review in January is the primary annual review, and when we assess compensation and perform a full 360 peer review. We then do a mid-year check-in review in July, but the focus is on the progress since the January review. We try to keep compensation reviews to January only, so other than promotions or some rare exceptions we do not review compensation mid-year.

We are contemplating moving our review cycle to annual in January with light quarterly check-ins. The reality is managers should be giving regular feedback, and not waiting for an annual or semi-annual review cycle, so regardless of the timing there should be no feedback delivered in a review process that is a surprise to the employee.

Annual planning and mid-year refresh

We start the 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 then 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.

We try to blend the two approaches in our planning process to get the best of both. We start with a broad company-wide survey and typically include some data gathering in our September/October QBR (more below). The management team then takes that input and starts to formulate the general themes and higher-level strategy. We take a few days for an offsite as a management team (along with directors and key stakeholders) in October/November to start building a cohesive plan. We then present the high-level strategy back to the teams in late November/early December for feedback. The teams then work on their departmental plans and the specific things they will execute in support of that strategy.

Engagement survey

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.

OKRs

OKRs stands for ‘Objectives and Key Results’, and they are a framework for tracking goals and progress. The Objectives are the goals you’ve set, and the Key Results are how you will measure progress toward each goal. The model was initially taught by Andy Grove at Intel and later popularized by Google after they were brought over by investor John Doerr. There are countless interesting articles and posts on OKRs and how different companies approach them, so you can learn more with a quick Google search.

We develop our OKRs on a sem-annual basis. We recently went from quarterly to semi-annual, as the overhead of creating them was too high and the changes over 3 months too low for a quarterly model to work for us. We use OKRs 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. We use Lattice to track our OKRs, but a well-designed Google Sheet can be just as effective.

One area of debate around OKRs is whether or not they should be used to assess individual performance and play an explicit role in performance reviews. My view is OKRs are more effective as an alignment tool, and should not be used for performance management. We want OKRs to be realistic but aggressive, and give people the opportunity to take some risks and place some bets. As soon as they become a performance management tool, OKRs become watered down and the sand-bagging begins.


Quarterly routines

Quarterly business review

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.

Roadmap refresh, prioritization

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.


Monthly routines

Monthly All Hands meetings

Once a month, typically on the last Friday of the month, we hijack the weekly Friday Town Hall meeting and do a review of our financials and key metrics and a deep dive into one or two key initiatives. You can think of this meeting as somewhere between the Town Hall and full QBR. It’s 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.

OKR metric updates

Once a month, we ask the team to go into Lattice and update your OKRs. The Lattice system makes it easy to update your Key Results and provide some color commentary on what is going well or not so well. We are looking for a quick update, not a full-blown report, so this should not create a lot of overhead for the team.


Weekly/biweekly routines

Departmental meetings

Every week or two, each team has a departmental meeting. The primary focus of these meetings is 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.

Business operations (‘BizOps’) meeting

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 Chartio dashboard that has the key business metrics, and then a shared Google 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.

Management team meetings

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. These presentations typically are in PowerPoint/Google Slides format. We have tried the Amazon 6-page memo format, 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.

Manager/direct report 1:1 meetings

Every manager should hold a 1:1 with his/her direct reports at least once every two weeks, and 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.

Friday Town Hall

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.


Summary

I think it’s important to wrap up by mentioning this is what works for us, and it may not work for your business, team or culture. This is a snapshot of how we run today, but we are in the process of working on changes and updates. Those adjustments will never end — what worked at 30 employees doesn’t work today with 90, and what works today with 90 won’t work when we hit 150. We will need to continually 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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