The people who created Mailbox are cooking up something new

Gentry Underwood
Jun 18 · 7 min read

Navigator is an AI-powered teamwork assistant that helps people work together effectively. It skillfully handles some of the most important and common tasks at work — like putting together goal-driven meeting agendas, or helping groups make important decisions.

We’re in the middle of an AI revolution — one that’s transforming computers into intelligent machines that drive our cars, spot diseases, and automatically assemble playlists of music we love. And increasingly, machines that are capable of having effective conversations with people.

Navigator is an intelligent machine, carefully programmed to have structured conversations with humans using an ever-growing collection of best practices for working together. These workflows are drawn from the research of scholars and experts, as well as our team’s experience working at Apple, IDEO, Stanford’s d.School, MIT’s Media lab. This is tantamount to coding the world’s streets into a vehicle’s navigation system.

But we’re getting ahead of ourselves…

Mailbox was the product of an experiment. When we founded Orchestra (the startup who created Mailbox), Scott and I had just come from Apple and IDEO respectively. We had held similar roles, designing and deploying internal software systems that helped some of the world’s most effective creative teams be even more effective. We were impressed by the power of software to improve teamwork, and wondered what we could accomplish if we started a company with the same goal.

Orchestra, our team-focused to-do list, eventually evolved into Mailbox, a mobile email client that leveraged the Zeigarnik effect and principles from Getting Things Done to help people stay on top of their inboxes (the place, we’d learned, where most shared tasks already lived). The scale of Mailbox’s success nearly overwhelmed us, and in the weeks that followed launch we decided our best hope for growing the team quickly would be to join forces with a larger and more experienced one.

After joining Dropbox things became more complex. Many on the Mailbox team took on broader roles in the company, while Dropbox’s own rapid growth meant it was just as hard to add people as if we’d stayed on our own. Eventually a company-wide shift in strategy resulted in the app being shuttered and the team redistributed.

Following the wind-down, some of us from the team would go on long walks to debrief and reminisce. And as we talked, we realized that we still had the same itch — we still believed that software was ripe with potential for transforming teamwork well beyond anything humanity had yet seen. And so we decided to try again.

Early human daily life · source

Teamwork is fundamental to the human species. It’s how our earliest ancestors survived in lands full of more ferocious predators. It’s how they — and we — build our homes and communities. It’s how we mastered agriculture and how we put a man on the moon. Teamwork is what makes scientific progress possible and enables religions to function. And teamwork is the common secret behind every corporate success in the modern world.

But we don’t pop out of the womb knowing how to work together. Teamwork is hard work. And the bigger teams get, the harder teamwork becomes. Whereas a team of 10 people might be able to sit around a table to make decisions, a team of 50 doesn’t really have that option (much less a team of 50,000). As team size grows, the amount of work needed to keep everyone in the loop explodes. At some point it simply becomes too much.

Organizational processes

The best solutions humans have come up with to handle the challenges of scaling teams are organizational processes — specific ways of working together that route information efficiently and help us focus finite attention on the conversations that matter most. There are countless processes, but to name just a few: design thinking for product development, OKRs for goal management, Kaizen for continuous quality improvement, and decision quality for decision-making.

Organizational processes are incredibly powerful. They’re why MBA degrees and consulting firms can be so impactful. They’re why people read HBR and keep business books on bestseller lists. Apply a better process and out comes a more capable team.

But as helpful as these methods are, their application is far from consistent. Some teams work together remarkably well; others do not. Some leaders geek out on management techniques; others have no leadership training. Some executives have staff running around doing administration for them; others are left to run teams on their own.

Sometimes the issue is one of familiarity, but often the problem is just that there’s too much to do. Most leaders know that the difference between a great meeting and a terrible one is largely preparation, for instance, but many are just too busy to build agendas and distribute pre-reads.

But what if someone (or something) else handled all that busywork instead?

An all-time favorite robotic teammate · source

Automating best practices

For the last few years our team has been experimenting with ways of using software to facilitate better teamwork. Like a rag-tag band of Edisons, we went looking for that ideal product: something that would be easy enough to adopt that curious teams could start using it on their own, while powerful enough to transform the ones who did. After some 200 experiments, we seem to have found a formula that works: robots.

OK — not robots exactly, but their software equivalent: teamwork assistants. Robot-like virtual team members, carefully programmed to guide teams through best practices for working together, just like a human might.

For example, a teamwork assistant can suggest questions to ask in a 1-on-1 meeting to build trust or foster career growth, and can adapt those suggestions based on the relationship between the two people meeting.

Additionally they can do the important-but-rote work necessary to facilitate these processes — like gathering answers to those questions ahead of time so each person can digest them before the meeting.

It might feel far-fetched to imagine working alongside a ‘robot’, but in many ways it makes the perfect teammate. It’s always available. It can have multiple conversations simultaneously. And it’s proficient at running repeatable processes (like gathering feedback, organizing meeting agendas, or facilitating a group decision) in consistent, reliable ways.

Imagine an assistant that’s programmed to add career support into every 1-on-1 meeting

Meetings that matter

While our long-term vision for Navigator is to assist with all kinds of teamwork, we’ve started by teaching it to help facilitate productive, meaningful 1-on-1 and team meetings. Meetings are high-leverage moments in teamwork — exceedingly painful when run poorly, and exceedingly powerful when run well.

The secret to well-run meetings isn’t a secret at all, it’s just a lot of work — the kind that often slips through the cracks when teams are busy. Great meetings require preparation ahead of time, both in gathering input and distributing pre-reads. They require good structure and organization during the meeting to make sure everyone stays focused, and someone has to keep track of what happened during the meeting and who agreed to do what afterwards. This is the kind of work most humans don’t like doing, and the kind that Navigator is very well-suited to handle. Win/win.

Before each meeting Navigator reaches out to attendees and gathers discussion topics, organizing them into a goal-driven agenda that it distributes as a pre-read. During meetings it provides a shared surface for capturing notes and action items as they emerge. Afterwards Navigator follows up with everyone, sharing what was captured with each attendee. Then before the next meeting it circles back, checking in on progress and repeating the rest of the process.

We’ve been developing Navigator for the past year or so with 50+ teams of all kinds, spread across the United States. Teams in large corporations and small startups, educational and non-profit institutions and numerous churches. The results have been very encouraging.

Each week 80% of meeting organizers and 40% of participants work with Navigator to prepare for their meetings. And in qualitative interviewing we’re seeing transformation: teams report more productive meetings centered around focused conversations that all attendees feel invited to participate in. That’s a big deal.

Meetings are more productive when the purpose of discussion topics are clear

Say Hello

We’ve designed Navigator to always be learning. Every day we’re teaching it, both to improve what it already does and to give it new skills and abilities. Right now we’re focused on 1-on-1 and team meetings; soon we’ll support other types of meetings, as well as related processes like decision making, feedback gathering, and problem solving. Our goal is pretty simple: help Navigator become the world’s best teamwork assistant.

And that’s where you come in. It’s our job to teach Navigator, but what we teach it will be a result of what users teach us. And while there is still a lot to do, we’re encouraged enough by early testing that we’re ready to invite more teams to try the service.

If you’re curious about how a robotic assistant might help with your team and 1-on-1 meetings, please visit Navigator and say hello. The service is free while we’re in beta, with no obligation to continue (we’re planning to make a paid version available later this year). Our only request is that you let us know what you think.

On behalf of the team — and Navigator — thanks. We’re pretty excited about the road ahead.

Thanks to Anthony DeVincenzi, Tony Devincenzi, Colin Dunn, Claire Rudolph, Belinda Preno, Heath Packard, Stephanie He, Enrique Allen, and Scott Cannon

Gentry Underwood

Written by

Entrepreneur and designer

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