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Is productivity software making us less productive?

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I'm Ezra Klein, and I'm addicted to productivity software. Evernote, Google Drive, Momentum (particularly the Chrome extension aimed at to-do lists, but I also use the habit-tracking iOS app), Fantastical, Slack, Dropbox ... I use it all.

But I'm particularly addicted to Trello, which is a visual task board where I organize everything from pieces I want to write to movies I want to see to meetings I need to attend. And I'm not alone. The company recently announced it's hit 10 million users, and it launched a new, more powerful product for enterprise users.

Michael Pryor is Trello's CEO, and so he has an unusually clear vantage point into the habits of, well, productivity app addicts like me. So when I got a chance to sit down with him recently, I asked him whether he thinks people using all these productivity applications are actually making themselves any more productive — or whether we've just found a new and more socially acceptable way to waste time.

Pryor, happily, was willing to entertain the question. A transcript of our conversation, edited for length and clarity, follows.

Ezra Klein

I use Trello and I use Evernote, and now I have Slack and Momentum and Google's suite of services, and simply keeping them all updated and current takes a lot of time. Do you think there's a point of severely diminishing returns? Is there a point where people get too into all this productivity software and it all becomes a drag on their productivity?

Michael Pryor

Absolutely. One of our first products was a bug tracking application for software developers called FogBugz. When we built it — this was a decade ago — the bug tracking app that everyone used was a thing called Bugzilla, and, basically, when you went to make a new bug, you had to fill in, like, 40 fields. It was things like, "What computer version is it, which operating system, what was the priority, what was the severity," and developers hated it because it took 20 minutes to enter a bug. So they just wouldn't use it. So in our product, you basically make a bug with just a title. That's the only thing you need to supply. If people need the other information, they'll be able to get it.

With Trello, the idea was to make a collaboration app that was visually restricted. Essentially, how much stuff you can put on a board is limited because it just gets overwhelmingly difficult to put more than what you see on the board itself.

There are people who get a lot of enjoyment out of spending all this organizational time keeping their life in perfect order, but that's not how I operate. For me, it's a matter of just prioritizing. There's way too much stuff, so I have to pick out what's important right now for me to focus on.

Ezra Klein

I have this theory that people overestimate the hassle of how hard it is to fix things when they go wrong and underestimate the hassle of the buildup of small things we do every day to keep them from going wrong. I feel this way about a lot of zero-inbox efforts. I think people overestimate the difficulty of just searching to find things in your email, and they underestimate the hassle of constantly, continually, killing or sorting every piece of email they get. When you add all that up, it's a really big cost.

Michael Pryor

I think you told me before that you just never clear your inbox.

Ezra Klein

Absolutely never. I use Gmail, and it's got that priority inbox function. It's actually pretty good. I find there's very little that slips through that I wanted to see. But the problem for me is it's become good enough that I really don't check the non-priority inbox, so I have no idea what's slipping through at this point.

Michael Pryor

Right. I'm exactly the same way.

Ezra Klein

But I think that's a good example. The work of checking the non-priority inbox to make sure I never miss an email I wanted to see is much more than the work of apologizing if somebody sends me an email that I didn't get. Related to this, you use Slack, right?

Michael Pryor

Yes.

Ezra Klein

What is your confidence level that Slack is productivity-enhancing rather than productivity-depressing for your employees?

Michael Pryor

This is tricky. One thing I notice is that most of the chat activity is actually direct messaging in our organization. Like, 70 percent. You could sort of read that either way. Are people just chatting and gossiping and talking? Or are they just actually getting work done and it's perfect because now it's not interrupting anybody else? So there's that.

In our particular case, our company is half-remote. If everyone were in the same office, I think the way we use chat would be a lot different. For now, there's a certain element of talking about not-work stuff that's appropriate and part of building a relationship with the people you work with. We would need that a lot less if people were all in the same space.

So I think Slack has allowed us to be a remote company and be more connected than we would be otherwise. If we didn't have chat, I don't know if we would be able to be completely remote. We'd have Trello, where we would be doing our actual work, but it would be much harder to have a sense of culture and community in the company.

Ezra Klein

We're 95 percent in the same office, and it's I think a real testament to what a usable, delightful product Slack is that it has almost entirely overtaken vocal communication. We joke that meetings are just live Slacks. The reason I worry about Slack is I think it's created a weird third category of work-like goofing off. It's created this thing that you have to pay attention to, and it feels like it's part of your job to pay attention to it, but primarily what's happening in it is not that relevant to your work.

You look in your Slack sidebar and there are all these messages you haven't read. It gets under your skin. People really feel like they need to be following it. They're working on something and then they click quickly back to Slack to make sure they're keeping up, because it feels like if you don't keep clicking back, you're going to fall irretrievably behind and come back and have a million messages to read. That's work they're doing, and it's work they're feeling tired from doing, but it's not helping the organization or them very much.

Michael Pryor

Yeah. I agree 100 percent. It's not really Slack, it's chat, right?

Ezra Klein

Yeah, it's all chat.

Michael Pryor

Since we both use Slack, that's why we're saying Slack. I think a lot of the software developers have gotten very good at quitting out of chat and setting aside large amounts of time to not be distracted by that. It's like, don't just read about work, go make work — go make stuff that's going to make people buy more of our stuff.

Ezra Klein

One of the things I think about with all this software is the tyranny of the to-do list. There's a bias toward highly structured things that can be broken down into a task versus more unstructured work that doesn't easily break down into tasks but might be more important.

So, for instance, if I have a piece to edit, that's very easy to put on my to-do list, and very easy to keep in front of me until I get it done. Spending two and a half hours just reading things that catch my eye isn't really a task in the same way — there's no deadline, no one is making me do it — but it's important for long-term creativity. But because I have this huge to-do list of discrete tasks, I worry my time is biased against more unstructured kinds of work and learning.

Michael Pryor

I think part of the trick to getting stuff done is having the right perspective. At Trello, we have a board for the whole company that describes our current goals, basically, and how the projects we're working on are accomplishing those goals. But there's not a lot of meat in that board; if you wanted to actually know what was going on with any one of those particular projects, you'd have to drill down to a different board. So that allows me to look at the company from a broader perspective and not be inundated with all this information that's coming across at too low a level of detail.

But I've gone in my career from being a developer where I was writing code and producing things to now being in a position with a lot more interruption. My calendar is just full, people have questions, problems come up, etc. I don't have those big blocks of time to get creative work done, so that part of my job just suffers. I don't get to write code anymore, because I'll just never be able to cordon off enough time to do it.

In your particular case, you're talking about reading stuff on the internet. Even if you don't block off time for that, I'm sure that you would start to feel if you were losing touch with what was going on. It would be very apparent to you. You wouldn't have to schedule it.

Ezra Klein

I'm not sure that's right. There's a superficial level of knowing what people are talking about on Twitter; that's easy to keep up with. But I think the cost of not having that unstructured research time is that I don't find an insight I would have discovered a couple of years ago, and I never know I didn't have it. I think it's very hard to come up with new ideas if you're just pulling the exact same information everyone else is pulling.

But this is one of the problems I have with services like Twitter. I think one thing the computer age has done is give us these really powerfully habit-forming information services that trigger this feeling that if you don't check in every couple of hours you're going to miss things forever. And I think that biases our information consumption in pretty bad ways.

I have a stack of books on my table, and I know they're going to be there tomorrow and next week and next month, so it's easier for me to put off reading them than it is to put off reading Twitter or Facebook or these things that feel more ephemeral. And I wonder if I'm doing a good job getting the best kind of information or if my informational consumption has become just way too oriented toward things that have that ephemerality to it.

Michael Pryor

Yeah, I find myself taking in information in a lot smaller chunks. Now you get a copy of Harper's and if you want to read one of the articles, it's like, "Oh, now it's going to be a 10-page thing," but after you do it, it feels so different and so much more tangible than the enjoyment I get through my Twitter stream.

But here's a good thing that came out of this. I look at my daughter, and she has this iPad in front of her. And I think back to when I was a kid and we had the TV in front of us, essentially. And at least with the iPad, it's actually much more active. The iPad feels like a better interaction than if she were just watching TV.

That said, reading a book is very similar to TV in the sense that reading is a very solitary activity. But we have this nostalgia for reading. I don't know what it is about that that we've elevated that experience over watching television.

Ezra Klein

It sounds to me that there are two kinds of distinctions here. There is fast versus slow kinds of information, and then different levels of interactivity. With the iPad versus the television, you might be dealing with very similar kinds of information, but the iPad has a higher level of interactivity. Reading a book versus reading Twitter is about a harder, slower kind of information as opposed to a faster kind of information, and that's where I think you're probably having more cost right now.

I think that interactivity of media is rising, but the difficulty of that media is probably going down. I feel it in myself. I feel less able to read a hard book that requires many, many hours of serious engagement to process than I did seven or eight years ago, and I wonder what it's going to be like to grow up in a world where you may never really need to do that because the dominant approach to being informed will just never require that.

Michael Pryor

Yeah, there's something about the creative emptiness that you're given when you read a book — the fact that you need to fill in so many different things in your head and your brain is sort of exercised in a way that TV doesn't do or even the iPad doesn't do. It does feel a little bit like exercise.

It seems like there's something in human nature that's drawing us to this shorter dopamine hit of the Twitter feed or the Facebook post or the interactions that are very short and not very deep.

Ezra Klein

Let me ask you one more question and then you can get on with your day. What do you believe about being happy at work that other people don't believe?

Michael Pryor

This is really evident in New York when you go into any office space, but I think that to be both happy and productive as a knowledge worker, people should have an office with a door that closes. These offices with open desk plans are really disruptive — I think there's so much energy being spent to avoid being interrupted, and that energy could be better spent on producing things and being creative.

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