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How Twitter, Dropbox, Airbnb, MailChimp, and other tech companies run design meetings

4 min read
Thomas Sugar  •  Mar 4, 2019
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It’s the designer’s nature to seek creative solutions for everyday problems, and most of us, at least in tech, can say that meetings are an every-dang-day problem. How are we supposed to do great work when our calendars don’t leave room for a bathroom break?

Here’s how designers from seven leading companies—Airbnb, Twitter, MailChimp, PayPal, Hubspot, Dropbox, and Zapier—run meetings that their employees are happy to go to.

MailChimp: Stakeholders only, please

As told by Holly Tiwari, Senior Product Designer:

To make the best use of people’s time, the meeting room at MailChimp tends to be reserved for those who are stakeholders or knowledge-bearers on the project at hand.

“I start with the shortest time and the fewest people possible. When I need multiple people involved in a decision, I’ll break it up into several smaller ‘prep’ meetings with different types of team members—like engineers, designers, and support—since conversations move faster with fewer people involved.

“When I need multiple people involved in a decision, I’ll break it up into several smaller ‘prep’ meetings.”
Holly Tiwari, MailChimp
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Then we have one final meeting to regroup on alignment that acts as a recap for everyone involved. This typically moves things much faster, since the meaty discussions have been hashed out already.”

Holly Tiwari, Senior Product Designer

Tiwari pushes for regular progress reports to all project stakeholders, both within and outside of the design team. These maintain open channels of communication, without paying the time toll.

Even with these reports, feedback sessions were tending to spiral, so Tiwari introduced another feedback mechanism: sticky notes.

“As one designer presents, others capture feedback on sticky notes. We then go around the room and share one note each and the presenter gets to keep the full stack of feedback notes. This captures robust feedback without the need for participants to verbally relay all their notes.”

PayPal: Think in stories  

As told by Jai Dandekar, Design Lead:

At PayPal, our meetings range across a very broad spectrum of topics, as I’m sure you can imagine, yet the customer is still the continuous thread throughout all of them. From design reviews to architecture meetings to roadmap planning, each and every one of those meetings ultimately maps back to doing what’s best for the customer. It is not the charter of design alone to advocate for good user experience. I’ve heard many people from a wide variety of roles (e.g. Legal, Ops, Account Management, Engineering, Architecture, Product Management, etc.) ask the question “Is this a good experience for our customers?” and push for that better experience.

Customers are at the heart of all of PayPal’s meetings; therefore, the company’s “process of discovery” is led by cross-functional teams.

“This cross-functional lens allows us to solve real customer needs in a way that results in tangible business outcomes. Most of my meetings are with folks from across organization, focused on testing, reviewing, iterating on and refining designs,” according to Jai Dandekar of PayPal.

Jai Dandekar, Design Lead

One of the most important factors in scheduling meetings at PayPal is whether people will have enough time to provide feedback, ask questions, and talk out their ideas.

“From design reviews to architecture meetings to roadmap planning, each and every one of those meetings ultimately maps back to doing what’s best for the customer.”
Jai Dandekar, PayPal
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“It’s not enough to see the work; the meeting needs to also accommodate for the time it takes to process what they’ve seen and react to it. Otherwise, the meeting feels rushed and after it has concluded, the sinking feeling that not all goals were reached sets in.” he said.

Jai uses a storytelling approach to guide his meetings. Using the customer’s narrative and real-world situations, he puts himself in the shoes of PayPal users to encourage empathy and increase his colleague’s engagement.

He also adopts a pioneering approach to meetings that veer off-course.

“Tangents usually occur when someone misinterprets the design, sees something they associate with something else entirely, or doesn’t understand the intent of what’s being presented to them. Once the meeting goes off track, I don’t immediately step in because tangents aren’t always a bad thing—if they can lead to productive and meaningful conclusions.”

Twitter: Brief everyone before the meeting

As told by Lisa Ding, Senior Product Designer:

Determining a meeting’s length is surprisingly complicated.

It’s a common misconception among meeting leaders that a meeting should be at least 30 minutes, and max out at 1 hour, with longer meetings involving more employees and higher-level discussions.

“It’s a common misconception among meeting leaders that a meeting should be at least 30 minutes and max out at 1 hour.”
Lisa Ding, Twitter
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At a company like Twitter, though, where employee time is in high demand, it’s rare to find an hour-long window that everyone shares. So, the trick is to brief everyone before the meeting as much as possible—even if that means holding a pre-meeting.

When designers are invited to enter a project after project managers and engineers have determined their roles, that’s what ends up happening. Those pre-meetings assure that by the time all stakeholders are in the same room, they’re also on the same page.

“If the attendee is intimately familiar with the project, I often don’t need to budget extra time. At Twitter, I find that product managers and engineers are already pretty familiar with what designers do. Sometimes, it’s actually presenting to designers who aren’t involved with the project that requires extra time for context, so I’ll budget an extra 10-15 minutes for that.”

Airbnb: End each meeting with feedback

As told by Adrian Cleave, Director of Design:

As companies and projects grow in size and scope, meetings become multi-celled monsters.

To keep meetings on track, Airbnb’s Director of Design takes the time to classify every meeting in one of four ways:

  • A decision that needs to be made
  • Cascading information
  • Working session
  • Cultural moment
“Having an assigned meeting facilitator is important to gently steer the conversation back to the agenda, make sure time is managed, and that everyone has a chance to be heard.”
Adrian Cleave, Airbnb
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By narrowing down the meeting’s purpose, Cleave can then invite the minimum number of stakeholders required and keep his meetings nimble and effective. He also likes to have a facilitator in each meeting to keep the discussion on track:

“Topics that tend to cause tangents usually relate to either a lack of alignment on the goals or a specific topic that goes down a rabbit hole and gets stuck in the weeds. Having an assigned meeting facilitator is important to gently steer the conversation back to the agenda, make sure time is managed, and that everyone has a chance to be heard.”

Adrian Cleave, Director of Design

Even the best strategy may need further refinement, so Cleave sets aside five minutes at the end of every meeting for participants to give ratings. The participants who provide the highest and lowest scores then have the opportunity to give specific feedback that Cleave can use for planning future meetings.

Hubspot: Ask these four questions before sending an invite

As told by Hugo Welke, Product Designer:

Have you ever had the displeasure of sitting in on a meeting like a silent partner, watching the minutes pass while you wilt away in silence?

That’s why whenever Hugo Welke draws up the attendee list for a meeting at Hubspot, he poses four important questions:

  • Will they have an opinion?
  • Do they want to be involved?
  • Will they contribute or learn something?
  • Do we need to get alignment on the topic?

Anyone who doesn’t meet those criteria is left out of the meeting.

“If things go off on a tangent and the off-topic is an actual blocker to solve the issue that we were trying to solve first, I’m always happy to switch the topic of the meeting and take advantage of the time that we have together to discuss the issue.”

Welke likes to spend the first five or ten minutes of a meeting describing the issue they’ve convened to discuss, and keeps things moving by sticking to the subject at hand unless something more critical comes up.

Hugo Welke, Product Designer

“If things go off on a tangent, I’m always comfortable to ask people to take that offline to discuss and/or if the off-topic is an actual blocker to solve the issue that we were trying to solve first, I’m always happy to switch the topic of the meeting and take advantage of the time that we have together to discuss the issue…I always encourage people to talk and express their opinion and also to listen to other people’s opinion too.”

Dropbox: Invite non-designers

As told by Sheta Chatterjee, Product Design Manager:

“We really want meetings to be as short as possible. 30 minutes of five people’s time is more than two hours of productive work time.”

To encourage efficient meetings, Sheta decides the length according to the purpose. Informational meetings are short and sweet; decision-making meetings, however, are given a full hour.

Sheta Chatterjee, Product Design Manager

Dropbox likes to invite other teams to meetings to help determine whether a designer’s vision is technically feasible.

“If something goes off track, the facilitator will ask to take that topic offline and refocus the agenda.”
Sheta Chatterjee, DropBox
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“When we invite non-designers, we usually go over the project we are presenting on a high-level first. We talk about the core problems, the evidence we have that these are problems and why this project is important. This helps us set the context for others in the room who aren’t as deep in the weeds,” she said.

Sheta usually invites a “facilitator” to a meeting to prevent the session heading off on a tangent and to ensure Dropbox fosters a safe space for all ideas to be heard.

“This person is responsible for ensuring everyone has a voice and the meeting keeps to the agenda. If something goes off track, the facilitator will ask to take that topic offline and refocus the agenda.”

Zapier: Use critique squads

As told by Adam Kaplan, Product Designer:

Have you ever attended a series of meetings with different departments and ended up discussing the same subjects at every meeting? Adam Kaplan has found a simple and intuitive way to improve intra-department communication at Zapier by using “Critique Squads” to share ideas and feedback:

“Every squad is made up of front-end engineers, product designers, product marketers, and UX researchers. Having a cross-disciplinary critique helps encourage divergent design ideas and gives us a better insight into the product initiatives across Zapier…The agenda that I send out allows squad members to prepare for each meeting beforehand and provides guidelines for giving critiques.”

Adam Kaplan, Product Designer

Kaplan believes that his Critique Squads are helping Zapier build a more inclusive and collaborative feedback cycle because the relatively small groups allow every voice to be heard.

“Having a cross-disciplinary critique helps encourage divergent design ideas and gives us a better insight into the product initiatives across Zapier”
Adam Kaplan, Zapier
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Pinstriped: Janus Moller, Design Lead

Here at Pinstriped, meetings are our raison d’etre—so it’s no surprise that Janus Moller has some strong feelings about making them lean and productive.Beyond everything else, he recommends keeping all meetings as short as possible; Janus feels that trimming his meetings down shows respect for the attendees, who no doubt have plenty of other uses for that extra fifteen minutes.

Additionally, he believes that Pinstriped’s agenda timers are another great way to show respect:

“I have always disliked looking at the clock during a meeting. I feel it can be stressful for the participants and I don’t like what it signals. I, of course, use our own meeting tool, Pinstriped, for running my meetings and find that the agenda timers are a much more subtle way of sharing with meeting participants where we are in the agenda and how much time we have left.”

Janus Moller, Design Lead

Janus finds that the agenda timers also inspire participants to keep the meeting on track without prompting, sparing organizers the unpleasant task of cutting off attendees in mid-discussion.

“I have always disliked looking at the clock during a meeting. I feel it can be stressful for the participants and I don’t like what it signals.”
Janus Moller
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Can you run a company without meetings? Probably not. But if you can invite just the right people, draw up a great agenda, and use smart strategies to keep your meetings on time and on topic, you might just develop a new appreciation for the humble business meeting.

Want to read more about running meetings?