How Trivia, Blobfish, and Weekly Demos Keep Our Product Inclusive

Learn how Square Root’s Product Managers foster inclusion + innovation during Weekly Product Demos all while having fun, too.

Kelsey Peterson
8 min readAug 12, 2020
Square Root Radicals gathered together for a Weekly Product Demo

Every Friday, our team comes together, caffeine in hand, for an hour-long product demo. It’s an opportunity to see, learn, and interact with newly finished or still-in-development features. The latter part is important to highlight. We demo in-progress work for all the Radicals (our moniker for employees) to garner feedback and fuel creativity. Demos are an opportunity to take advantage of the diverse perspectives of our team. They’re also one of the many reasons we recently landed on the Fast Company Best Workplaces for Innovators 2020 list.

For our product team (dubbed the Blobfish herd), keeping everyone in sync with the product’s direction is a key part of the role. It’s more than just building a nice, big roadmap with a lot of details, dependencies, and estimates. It requires constant communication, adaptation, and presentation to help bring our product’s vision to life.

Our Weekly Product Updates are designed to provide this communication + a strong feedback loop for new features, especially those in the works. I sat down with our product managers — Herschel Kulkarni, Taylor Coppock, and Ryan Andrews — to discuss why the Weekly Product Demos are so impactful, how they differ from other startups + companies, and why trivia makes the perfect icebreaker.

But first, what is a Weekly Product Demo?

For our Radical team, it’s the perfect time for any department (aka, our herds) to:

  • Share updates from the past week;
  • Collect feedback, align the entire company, and think about the impact of our projects + actions;
  • Embody our values and think about how someone will experience a new feature, idea, or design.

Why have a Weekly Product Demo?

Taylor: I love building things and showing them off. There’s nothing worse than a cringe-y dry demo that falls flat, but there is nothing more energizing than the feeling of others celebrating decisions you made and nodding their head with the direction you’re taking a product. If you’re not having these conversations weekly, you’re missing out. A lot changes in a week. I currently manage two Dev teams running 2-week sprints, so there is no lack of product updates ready every Friday. One team is building workflow products that naturally tell a story. The other team might be boosting up Permissions, which deserves more product story attention. These may be fully tested workflows, running on a developer’s local machine, or might be rough mockups. But each one is valuable in their own right. The most effective method of sharing the information is during the hour-long Weekly Product Update. It allows us to dive into complex topics and elevate from awareness to understanding. Spending an hour thoroughly understanding the future direction of the product saves so much more time down the road.

Ryan: I think there’s something about just having everyone’s attention. There’s an expectation during the Weekly Product Update that you are there to get the latest updates in and around the product. It’s not just some message blasted out via email or Slack that interrupts people’s normal schedule. Attending this session is part of everyone’s normal routine.

Who attends the weekly product demos?

Ryan: The whole company — the CEO, our sales and Customer Success teams, QA engineers, or those that handle Marketing + Operations (our Tamers of Chaos). Every Radical on our team is encouraged to attend. For us, having the entire team present is crucial to our product’s success. We want everyone, no matter their role, to be in sync and contribute to our product offering.

Taylor: And most weeks, the whole company actually attends. Radicals can join the meeting on the road or even when they are at client offices. With one rule, don’t join while driving!

Is it sometimes difficult to have a worthwhile update every week?

Taylor: Forcing ourselves to think critically about what to include every week matches the skill-set we use in our daily job. The challenge is showing off incremental progress towards a larger company objective that doesn’t conflict with the development cycle. Some epics will be shown multiple times as new decisions and improvements are made, so the challenge is being transparent and direct without being too repetitive. We move fast at Square Root! But an effective product manager will be able to craft a story to share with the company each week.

Herschel: Yeah, it can be tough, but it forces us to think about the most important thing each week. That means ruthlessly prioritizing what we’re giving our energy to, so while you can’t always make everyone happy, the weekly product demo pushes the big question, “Does this create value for our customers?” to the forefront. We strive for lively discussion at the product updates; that’s a marker that our team cares about the problems we’re solving. If we hear crickets we know we’ve missed the mark.

Product Managers Herschel Kulkarni (left) + Ryan Andrews (right) enjoy co-working from Square Root’s craftsman-style houses pre-pandemic.

How does this differ from a traditional Scrum Sprint Review?

Taylor: Traditional reviews are dry and often just presentations. It’s easy to forget what’s behind the words when they only read a Powerpoint about goals accomplished during a sprint. During the Weekly Product Demos, we focus more on the impact to the product that occurred in the previous week rather than a cohesive view of the slated work for the 2-week sprint. Those happen in other conversations, like our herd’s Retrospectives.

Ryan: There are also presentations from Radicals who are not working in a traditional two-week development sprint. For example, our design team has shown mockups of upcoming data visualizations to receive feedback before those changes go into a development sprint. Changes to marketing materials + our website have also been demonstrated to the entire company. It is a full circle picture of the product.

Herschel: Also, we ask trivia questions every week at the start of the meeting to get the creative juices flowing!

Speaking of trivia, how did that come to be?

Ryan: This started when the company had a “Trivial Pursuit” themed quarter, but everyone seemed to like it so we kept it as a great warm-up/ice-breaker as we kick off the meeting. It’s a different theme every week — sometimes tied to current events and other times just totally random. It’s sort of secret insight into what the product managers are thinking about lately, too.

Herschel: I’m terrible at coming up with topics and running trivia. I didn’t realize it was a talent until Ryan brought the house down week after week. One week I had to end my trivia with, “Which one of the PMs do you WISH ran today’s trivia?” I’ll let you guess who had the most votes.

Who demos these new features + enhancements?

Herschel: All Radicals have a chance to show off what they’ve been working on, including engineering, data science, marketing, and design. As Product Managers, we set the customer-centric context for the teams in and out of the demos, which empowers everyone to contribute. Giving customer context is the most valuable thing we can provide Radicals, especially our technical teams, so they can make thoughtful architecture decisions + think creatively about customer challenges. We do this by storytelling the customer journey, inviting all Radicals to join user interviews (dubbed Adventures in Empathy), and reviewing workflow usage. To come full circle, when work is shared at the demo, Radicals share their work in the context of its customer impact.

With everyone currently working remotely, how have these updates adapted?

Ryan: Thankfully, we already had some remote Radicals, so our updates have always been conducted with remote work in mind. All of the slides, roadmaps, and feature demos are shared in a virtual meeting. Questions can be asked in the meeting chat (or out loud), with us as moderators, calling out questions, and moving the meeting along when needed.

What are the most challenging aspects of presenting + demoing remotely?

Taylor: We’re storytellers. Removing the audience required us to interact in other ways. The 3 of us monitor the chat and video to ‘read the room’ so we can identify the parts where we need to dive deeper. It’s a challenge to balance all of the voices during the demo to ensure there’s diversity in who’s speaking. Encouraging all Radicals to write questions into the chat makes it easier for us to include their discussion into the update. But not being in the office removes the quick hallway chats immediately before + following the update.

Ryan: Ditto to what Taylor said. Sometimes I will present a slide and speak for a minute without any immediate feedback. Not being able to see the audience is tough. It can feel like you’re talking to yourself. I miss the pre-pandemic live faces of Radicals looking back at me.

Product Manager, Taylor Coppock, brainstorming with Software Engineer, Margarita Tijerino, in one of our cozy, Craftsman-style houses in Austin, TX.

What are the most valuable aspects of our Weekly Product Update?

Taylor: Even remotely, the feedback energizes us! It trickles into our Friday Slack conversations all day to help us feel more connected. Everyone wants a better product and to provide the right amount of constructive criticism.

Herschel: It forces us to focus. Focusing on the most impactful customer problems can be a challenge. But the Weekly Product Update makes the entire company think about and ruthlessly prioritize those problems.

Ryan: I deal mostly with data and backend pieces of the product. The exercise of explaining very technical updates to an audience forces me to highlight meaningful value — this process carries from idea to planning to execution. I’m always thinking about messaging and value: What details and key aspects are valuable for other Radicals? How were these new achievements customer-inspired? How do they tie back to our mission, vision, and values? These are just some of the questions that need to be addressed.

I hope you’ve enjoyed getting to know our Blobfish — notably their tight-knit, fun-loving chemistry which makes our Weekly Product Demos so memorable!

It’s important to create an inclusive space so everyone (no matter their role) can help shape your culture + product. Radical experiences, inclusion, and innovation are all intertwined — this is one of the many ways our team works to tie our actions back to the heart of Square Root’s values.

Square Root is a diverse team in Austin, Texas building data-curation software for the automotive + retail field. Interested in becoming a Radical or working with us? Get to know our team, learn more about our values, and why we’re named a Best Workplace for Innovators by Fast Company!

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Kelsey Peterson

People + Culture leader ~~ Singer-Songwriter ~~ cat mom