There are a lot of things that Slack gives you that email doesn't when you think about internal use. Switching to Slack from email for internal communication gives you a lot more transparency.

If you work at a 10,000-person company, and you're using e-mail as the primary means of communication, then you probably have access to a couple hundredths of 1 percent of all the communications happening across the company. But if you use Slack, you might have access to 10 or 20 percent.

I no longer file expense reports, so I no longer experience the pain of it. What if everyone had a virtual assistant to do that kind of effort... like approving time off or submitting time-off requests? We want to really encourage developers to create cool things for Slack.

Inside all the computers of any large corporation is every decision that gets made. But people spend a huge amount of time trying to find the correct piece of information.

About 80 percent of the photos on Flickr are public and searchable by everyone. In one sense, it's a place where people upload snapshots from the family reunion, wedding or the birth of a baby or something like that, but it's also a place where people go to show what the world looks like to them.

There was a lot of dialogue between the people who were developing Flickr and their users to get feedback on how they wanted Flickr to develop. That interaction made the initial community very strong, and then that seed was there for new people who joined to make the community experience strong for them, too.

I think tech lives inside of a society that still has a lot of systemic racism and doesn't stop at the boundaries of the tech industry. But neither is it especially exacerbated by being around technology. But it is maybe exacerbated by the irrational decision making of people who are trying to make money.

I see all kinds of people work hard all over the world, and some of them are barely making it. I don't just mean subsistence farmers. I mean people in the developed world who work multiple jobs, and because the cost of health care and child care eats up almost all of the living they make.

I can tell people a story that they believe in and get behind. So I'm good at the leadership part. But I've always said that I'm a terrible manager. I'm not good at giving feedback.

In software design, it's all about making a guess, trying it, and then learning from the experience.

I love cities. New York, Montreal, London, Amsterdam, Tokyo, Hong Kong, Singapore, Sydney, Melbourne, Toronto, L.A... but, I do choose to live in Vancouver. It's home.

I feel like the business side came more naturally to me along with the product design side, but managing and effectively leading large organizations of people is something that is perpetually challenging and the topic on which I am constantly looking for good advice.

It's very difficult to design something for someone if you have no empathy.