Sprint Planning at Wistia: Why the Team Slows Down to Move Faster

Andy Cook
September 6, 2018
Interview with Molly Wolfberg

We sat down with Molly Wolfberg, Senior Product Manager at Wistia, to dig into how her team sets priorities and executes on the right things.

As a longtime Tettra customer, Wistia is bullish on effective documentation and prioritization. These good habits enable them to innovate quickly, a requirement in the video hosting space. As the market leader in business video hosting, Wistia needs to stay ahead of changes in SEO, video quality, and smooth playback.

The product team at Wistia ensures they’re at the cutting edge by operating in an intentional way. Molly shares that sometimes, being intentional means slowing down. Their highly organized sprint planning process lets them move faster in the future.

“We do quarterly planning, and within that, we do project-based weekly sprint planning. So we have 2-4 designated projects we want to accomplish each quarter.”

As a senior product manager, Molly gets involved in every step of the process. She invests significant time in the high-level planning of the sprint, as well as the more granular tasks that the team sets out to accomplish within each task.

For example, as Molly explains, A/B testing might be one of the goals for the quarter. She thinks through the user experience and needs in a strategic way:

“At the highest level, we’re trying to think through the goal of A/B testing: what do people need, in order to evaluate which video performed better.”

In this case, there are so many ways you could build an A/B testing tool for Wistia. By starting with the goals that the customer wants to achieve and considering how the product can help, you end up refining the options and gaining a clearer idea of what is required.

Communicating the High-Level Strategy

In some ways, Molly works backward when sprint planning. She often begins by thinking about what she wants customers to read – or even say – about the feature or product the team is building. Molly refers to this as a “launch blog post”

“I try to write a short blog post. What would people talk about? I do this early, before the product or tool even exists.”

The launch article will usually be around 3-4 paragraphs, which is enough to act as guidance for the lead engineer and designer on the project. This serves to align people around the customer’s the pain point or opportunity. It allows the team to more clearly envision the strategy and what they’re working towards.

Following on from the high-level strategy, the team sits down and discusses some of the details. They think through positioning and any technical limitations of the tool or product. Designers and engineers work together to generate an idea of what things might look like. With this work completed, the team is ready to start getting input from other sources.

Seeking Feedback from the Frontlines

Molly mentions something at the forefront of the product team’s mind: feedback and input from the people who buy and use the Wistia products. Often, the best insight comes from the sales team, since they’re speaking with prospective users on a daily basis.

“We might ask the sales team – did anyone lose a deal because we didn’t have this feature, and then interview those customers. We try to use all of our customer-facing teams to dive into what makes the most sense.”

They use this user research to inform the feature’s technical needs and design. They continually seek more feedback until the team feels confident about the nitty-gritty of the project. Once they achieve this point, they can truly move into sprint planning.

How Sprint Planning Starts

Sprint planning begins with an engineer who builds the technical spec. This might live in various places like GitHub, Google Docs, or Tettra. The engineer will document things like:

  • The technical implications
  • The “must-haves”
  • The “nice-to-haves”
  • The components of the user interface

Once the information has been gathered, Molly breaks things up into quick user stories. These allow the team to break the project into smaller chunks that fit into sprints. In our example about A/B testing, this might be: ‘As a marketer I want to be able to test two video thumbnails against one another.’

The team uses Clubhouse to manage the sprint planning process. It’s basically like a smaller JIRA tool, according to Molly. They use it to manage user stories, how long sprints will take, how long the full project will take, and how many sprints are required to complete the full project.

This process usually begins at least a full month before the team is even ready to start breaking things down into weekly tasks.

Weekly Meeting Cadences

The team uses a weekly planning meeting to assess where they are and what blockers – if any – have arisen. Molly and her team sorts through the top priority issues and user stories to make sure they have enough information for an engineer to start working on the task.

This planning meeting usually happens on a Monday and is led by the product manager. It’s fairly cut and dry according to Molly. They move fast, covering only the most important things like key goals for the week.

They hold a similar meeting at the end of the week. This “grooming meeting” is generally led by the tech lead with help from the Product Manager. It’s often more technical and is focused on making sure the engineering team has what it needs to hit the ground running at the start of the next week.

Planning to Reach Goals

Historically, one of the key factors that has slowed down or weakened the effectiveness of the team is insufficient planning. The engineering team has struggled when product fails to allocate time and resources to high-level planning.

“Spending the initial time thinking about the project at a high-level is really important. It sets you up for a successful project that hits the goals that you need it to in the scheduled time.”

Having clarity about key goals is also crucial to the success of a project. If the success criteria are set out clearly from the start, it doesn’t matter what shape the project takes, as long as success can be measured at the end. They measure their success using a variety of tools and metrics, mainly ones supplied through Clubhouse. For example, a burndown chart helps you estimate how long a project has left based on what you’ve achieved so far by using a point-scoring system.

All of these catch-ups, meetings, planning phases, and sprints come together to form a strong quarterly process. A good process, paired with strong documentation, ensures Molly and her team accomplish what they set out to achieve. Carving out more time initially in an investment in the team’s future success. As Molly and the group at Wistia have discovered, it’s often critical to slow down in order to move faster.