Hi everyone! Like it says, I'll answer anything as honestly as I can. Some suggestions: ask about Wildcard, where I'm VP UX; Subtraction.com, where I've been blogging forever; The New York Times, where I was design director for 5 years—or my new book: How They Got There: Interviews with Digital Designers About Their Careers.
First off, thanks for joining us today. We’re happy to be hosting you on Designer News. I’ve got 2 questions:
You have a new book coming out, How They Got There, which is kind of a Founders at Work for designers. What was the inspiration for the book? Was there anyone that you wanted to interview, but didn’t get the chance to?
Between Wildcard, Subtraction.com, Kidpost, and your book, you stay very busy. What are some of the techniques you use for juggling many projects at once?
"How They Got There" was actually inspired in part by "Founders at Work." If you haven't read it, that's a fantastic resource for anyone interested in how tech companies get built, and really how people turn their ideas into reality. I read that several years ago and always wanted to read something similar about designers.
So a while ago, when I was between projects, I decided I would actually take it on and do it myself. I reached out to 14 wonderful designers I know and asked them to each spend about an hour with me over Skype/Hangouts. It sounded like it was going to be a fairly easy project in the beginning, but the editing of all the interviews into readable form was much more work than I anticipated.
I'm really happy with the end result though; a few people who have read the early drafts have said they can't put it down, which is really flattering.
As for how to juggle many projects at once, I don't know any killer secretes. My advice is to be really passionate about each of the projects you take on—there's no other way to get them done than to be able to sustain your enthusiasm through all of the ups and downs.
Also, I guess I've discovered since my wife and I had kids (we have a 5 yr old and twin 2 year olds) that having less time than you would like really forces you to make decisions about how you want to spend your time. I wasted so much time when I had tons of time to devote to side projects; now that I have nearly zero free time, I find myself conversely more productive than before. Weirdly.
Hi Khoi, thanks for doing this AMA. Your wikipedia page mentions that you "remade the way design is practiced at The New York Times". What particularly did you change and why? What was wrong and how did you improve on it?
@Daniel: I'm really proud of what we did at the Times though I tend to get a bit too much credit for it. (No idea who wrote that line on my Wikipedia page.)
That said, when I joined in 2006, the digital design team lacked cohesion, and was separate from the newspaper's art and design team. I rebuilt the team from scratch and hired about 10 or 15 of them, many of who are still there. For a good deal of my tenure, we worked hard on integrating the team into the operations of the larger news and business org. I also tried to make it more fundamentally a product design team than it had been before. That was kind of foreign to designers at the Times; most of them had worked in the more traditional editorial model, which of course produced wonderful stuff for print. But we tried to think of ourselves as designers of digital products more than editorial designers.
Finally, I’ll be able to take something out of my chest: why are your Twitter avatars always pictures of Batman (from the old movies)? Thanks!
It's been my avatar so long that I don't really even remember when I started using it or where I found the image. But I remember when I started using it I decided, “This is going to be my official avatar and I’m going to use it everywhere.” Partly that's because that old Adam West show has a special place in my heart—it's one of the first shows I remember watching as a kid—I wrote a little about this in this blog post. Also, I really liked that old David Byrne quote: “People will remember you better if you always wear the same outfit.” Over the years I've started to introduce actual pictures of my real face in various contexts where I think the Adam West avatar is a little inappropriate, but I'll hang on to it as long as I can.
I was not expecting such an extensive & honest answer… Thank you very much, sir. You made my day. :)
I was fortunate enough to briefly meet you at the Adobe Max conference this past fall. My company, Threadless, also had an iPad app premiere at the conference. We loved working with Adobe to create it.
I love what you are doing with Layup and would love to have some of these functionalities in our t-shirt designing app. What was your process working with Adobe on this app? And, do you know if any parts of Layup's functionality will be available through Adobe's Creative SDK? Or is this app stand alone? Sorry, lots of questions in one. Thanks again!
@Billy: I talked a little bit about the process in my blog post here and Wired wrote a bit about it in this article. But to recap: Adobe asked me to propose an idea for a tablet app; I worked up some thoughts for an early prototype of LayUp; they assigned an engineer to work with me to rapidly prototype it; we put it in front of a panel users to get their reactions; they then assigned a larger team to it, that I consult with regularly. The whole experience sounds similar to the one you had at Threadless, which is to say it's been a fantastic collaboration. I'm continually impressed with how industrious and effective and clever the team has been in bringing it to life.
As for whether part of LayUp's functionality will be available through Adobe's SDK, I think only Adobe's SDK team can answer that. Speaking only for myself, I imagine that if the answer is yes, it would be a qualified yes—meaning it won't be out very soon. Hope that's helpful.
Thanks @Khoi. We did have similar experiences and it was great. I see they have released a production version of your app. Very cool. Thank you again for the answer.
Hey Khoi! Thanks for doing this
One thing we struggle with as product designers is answering the question of what problem are we solving exactly, and who are we solving it for? Not in the general sense but in a very specific sense especially when building broad horizontal products like Wildcard for example. I wrote a post about this relating to Wildcard.
Could you shed some light on how you guys are approaching this? How do you align your messaging, design, and communication of how the product fits into a users life? Are there any specific things you've learned and can share relating to this process so far at Wildcard? Most people recommend building products vertically (narrowly focused) then going more broad, so I'm curious about how this design challenge impacts your communication and product design decisions
@Joe: This is a really insightful question; thanks for asking it and thanks for your article on Wildcard. You're really right on the money when it comes to the challenge we've taken on—we are trying to solve a very broad problem, which it's our duty to overcome a number of obstacles with adoption and marketing.
We did spend a lot of time early on experimenting with a very narrow focus. Ultimately though we decided that building a broad product was the best way for us to start putting our ideas into practice.
Normally I would be reluctant to follow this approach, but Wildcard the product is not the entirety of Wildcard the company. We have a number of initiatives that are tackling this problem from multiple angles. Specifically we have a partnership program that helps brands get their content into our browser as cards while at the same time readying that content to be compatible with a number of card platforms, not just ours. We also have a developer SDK that is in the works that will make our functionality more portable—it's a pretty compelling argument for our big picture perspective on cards.
All of which is to say we're just getting started. I've said many times that we don't at this problem through the lens of months but rather years—we are trying to effect a fundamental change in how people interact with mobile content, so the initial efforts you see are all foundational, and will evolve and change over time. Hope that helps.
Hi Khoi, longtime reader here.
- What has been your experience in transitioning from designer to design manager? Pitfalls, lessons?
- Do you think older candidates / self-taught designers face a disadvantage vs. kids fresh out of school?
- Has design, like many professions, become something you need to be wealthy to even get started in (or go into debt to do), i.e. going to a recognized school/program, or finding paid internships?
I can't imagine how low-income students could manage it these days.
@AJK: In the same order you asked…
- Transitioning from designer to design manager wasn't that difficult for me in terms of giving up design and being able to "direct" effective design work. But it was really hard for me to learn how to work effectively with people. It took a long, long time—years. In fact I still don't consider myself "done" in this regard.
- First I would say that there are self-taught designers all across the age spectrum. That aside, yes, I do think older candidates do face a challenge versus younger designers, at least insofar as this is true across all industries. One of the most valuable things to any designer is the time and flexibility to learn new skills, ideally without incurring extensive costs relative to their standards of living. Younger designers really have the edge here; they can acquire new skills very quickly with little impact on their standards of living. I wish this weren't true—not least because I'm getting older—but it is.
- No, I don't believe this is true at all. If you look at Behance or Dribbble, you'll see a tremendous amount of self-taught talent, particularly from Eastern Europe and South America. Stateside, it might be a different question—in my experience I've seen relatively little upward mobility in the demographics of designers. At the same time however, I don't think schooling is a prerequisite for design employment; that's been true for the past decade and I don't necessarily see that changing any time soon.
first of all thanks for your work, your books and your particular take on digital design, that shows its graphic design roots in a very wonderful way. your upcoming app for Adobe is great.
While the designer is always more than her tools, do you think that tools like your Adobe app will become more common and more powerful in the next, say five years?
Secondly, What kind of spaces do you think will be hospitable for editorial focussed graphic design? My question might sound as if it is operating on a (false?) opposition between editorial design and product design, but it does seem that there are some significant differences between the drivers and desires in these two modes.
thanks so much, looking forward to your response, yp
@Yolp: When you say "tools like your Adobe app," can I assume that you mean creativity tools on mobile phones and/or tablets? If so then the answer is yes, I definitely think that the design process will, more and more, start migrating from the desktop to mobile devices, and to the iPad in particular. It's such a powerful, capable tool, and there is so much about our design processes that is inefficient and broken that there's tremendous opportunity for tablet apps to help reinvent the way we tackle design. So yeah expect lots of change in the next five years.
As for your second question, I've been really encouraged by how adventurous digital publishers have been with editorial design in the past few years. There have been some really high profile projects from big name publishers, but what really excites me is how even startup editorial products are embracing the values of editorial design. Pitchfork and The Dissolve come to mind as two publishers producing fantastic content who are frequently applying custom design solutions on a per-content basis, to sometimes stunning effect. I don't really pay as much attention to editorial product design as I used to, but when I see examples like that I sort of wish I were still in the mix doing that kind of work. Sort of!
Hello Khoi, thanks so much for such a considered response. :-) by "tools like your Adobe app" i meant the iPad layout app that you are designing for Adobe. and i was really thinking about the 'automation' of layout tasks that have been traditionally in the designer's domain of expertise. So to put this rhetorically: with the increasing sophistication of machine learning and AI, which areas of the design process do you see becoming more ripe for machine learning "disruption" ?
thanks also for your thoughts on editorial product design. Wanted to ask you more about cultural differences between the editorial world and the engineering heavy UX world, but perhaps i should leave that for another session.
wishing you all the best from Bangalore, cheers, Yolp
@Yolp: I get you now. Yes, in fact I think there will be a lot of automation of tasks that have traditionally been in the designer's domain of expertise soon. Computer vision is a robust field that the product design industry has barely even touched; there are tons of interesting things that could be done with just a fraction of the computer vision technology that's being actively worked on at the moment. Imagine a user interface that truly understands its visual content, and that can automatically adjust itself accordingly. That would completely upend how today's designers think of templates and views; UX would become many times more complex—and interesting, in my opinion. Personally, I can't wait for that.
wow! was hoping, but didn't expect a second response. thanks so much for being so generous with your time and for a considered response.
the italicised "lot" (a lot of automation) in your response, is of course very significant! So UX design will be even more about systems and architecture and meta-pattens etc. But then what about design as form-giving?
Will there be other modalities of doing design which are not UX? while a certain amount of general UX thinking will possibly pervade other design disciplines too, what are the domains where interpretation, form-making, and editorial attention to close reading, textual nuances, and content, will not be subsumed under 'system-think'?
Or in other words, do you think that the tent of Design Thinking is capacious enough to accommodate various forms of design practice? or do you see UX thinking claiming to become the default condition / substratum of all design thinking?
and on a related note, would love to know what do you think Richard Buchanan's idea of design as the 'Liberal Art of Technological Culture'? 
 Buchanan, R. 1992 “Wicked Problems in design thinking”, Design Issues, 8(2): 5-21
I'm not deeply familiar with Buchanan's writings but I do subscribe to his notion that the logical progression of design from a craft or trade to a framework for thinking about most everything we interact with in post-industrial society seems right on (that is, if I'm even paraphrasing it correctly).
In answer to your question about whether UX is going to eventually pervade all flavors of design, I think the answer is probably yes, but not at uniform levels. Software will probably continue to be the most heavily seeped in user experience thinking; marketing design will get progressively more UX heavy as well, as will editorial design, though perhaps not as thoroughly. Design tends to follow the doors kicked open by technology, and technology is certainly imposing more and more systems thinking on everything we do, so there's a certain amount of inevitability there.
a big thank you once again. it has been wonderful to have this exchange with you, and although your last response takes me to yet another set of questions, I will stop for now. On a different note, do hope that you will have time to keep writing books too among all your myriad activities. I enjoy your brief reflections on films on subtraction but I understand that you are perhaps too pressed for time to develop them further. I for one, would really look forward to a book from you that explores design at the intersection of cultural journalism. all the best, Yolp
I'm sorry if I'm a bit late to the party, but I've just got up and into the studio. I am a final year university student and therefore things are really starting to get real. How would you recommend I begin to look around about getting a job somewhere? Or do you think I should stick to freelance? I have had about 3-4 years of experience with various freelance projects now, so I think I should hopefully have enough experience plus hopefully a degree. My work is all on my Dribbble page at the moment (dribbble.com/seangeraghty), do you think this is enough or should I develop a portfolio?
Thanks so much,
I really do think that you should develop a portfolio of projects that you're proud of. I don't think that supplants the Dribbble page; any good employer or client will look at both. But given two designers of equal talent, each with equally impressive Dribbble pages, I personally would go with the one who has gone to the trouble of formulating a coherent portfolio that tells the story of who he/she is and what he/she is good at and where he/she wants to go with that talent.
As for whether to stick to freelance or to go for a salaried job: I know this isn't going to be the answer you're looking for, but it all depends on you and your particular circumstance. Both paths have worked for all kinds of people.
Finally, I don't mean to be crass, but this is exactly what my new book How They Got There is all about. If you want to learn how 14 designers who have "made it" actually "made it," sign up for the release!
Hi Khoi, thanks for taking the time!
You discussed changing the direction of the NYT design team toward more of a "product" focus during your tenure. What are some of the steps you took to achieve this? Were there any specific processes implemented, or was it more of a revised way of thinking?
As design director, what was your involvement like on a day-to-day basis?
@Christian: I'd say that it was "more of a revised way of thinking" than a 12-point plan or anything like that. There are a few things that can effect change in organizations, and I focused on the two that I could impact most immediately: people and values.
For the former, I had the mandate to basically build a new staff;. That's an enormous advantage that not every new design director gets when taking over a new team. There's a truism in political circles that "personnel is policy," and I always liked that idea. If you get the right people in place, everything else becomes much easier.
For the latter, that was made a lot easier once I'd started to establish a foundation of "the right people." But there was also a campaign necessary to educate the organization about how digital products are built, and that was a big part of my job—talking to stakeholders, making presentations, bringing in best practices and speakers etc. That was basically my day-to-day involvement; having the right conversations or introducing the right ideas to help shift the team towards the kind of values that we thought were important.
Hope you're doing well. I'm glad that you're open to share with us.
I've got two questions for you:
How did you start your career as a designer?
When and how did you make your transition from graphic design to web design?
@Min: Great to hear from you. Thanks for the questions.
Well as a kid I was always into art and thought I wanted to be a painter or illustrator, so I went to art school with that goal in mind. But while I was there I tripped into graphic design and realized those were the problems that interested me the most, and that led me to doing design professionally.
I'm very passionate about doing graphic design but I really didn't like doing print design. So the web was the perfect alternative; I could use (most of) the tools of traditional graphic design but in an environment that was much more immediate, and a lot more forgiving in terms of mistakes. As the web matured and designing things became not just about layout but about behavior and making systems, I just got more and more engaged. I consider myself really lucky that I found the right calling!
Hi Khoi. I love your work! What's your top 3 (advices given to you over the years, books, places in NY)?
@Kimberly: I'm not sure these are my top three best ever things, but they're certainly among them.
- Being professionally happy has less to do with what actual work you're doing than it does with genuinely liking the people that you work with —including yourself
- There's nothing better or more valuable than being in charge of your own time. Having a spectacular, well-paid design job that entails constant meetings and travel doesn't hold a candle to being able to hang out in a park on a spring afternoon anytime you like.
- The job of a designer changes every five years. It's very hard to plan for that kind of thing, but knowing that change coming is a huge advantage.
I'd be remiss not to mention that there are tons of similar insights in my new book!
Hi Khoi, hope you're still answering questions! You've obviously seen a lot of digital design practices grow and change over your career. What do you think are the most interesting open problems or areas of improvement in digital design today?
@Celine: Yes, still answering questions! What's most interesting to me today is evolving the way we access the information that's relevant to us on mobile devices. We're still just in the first decade of this, and there's still so much further to go. This also happens to be the problem that we're working on at Wildcard—trying to figure out a "third way" between native apps, which offer the best user experience on mobile but are inconvenient to access, and the mobile, which has tremendous breadth available at an instant, but is a pretty terrible user interface. So deep linking, cards, the portability of rich functionality—all that stuff I find really fascinating. And it's only going to get more interesting too with new devices like Apple Watch and Android Wear and whatever else comes along in the next few years. Our current models for how we use mobile computing are going to change dramatically before this decade is out.
Thanks for doing this! Loved your contribution to the NYTimes.
The expectations of the audience naturally ebbs and flows, evolving over time.
What's your philosophy on pure, unseen innovation versus willingly accepting the tried and tested? And if it applies, how do you strike a balance?
@MH: I want to say "You've got to have a balance of the two." But that sounds glib. Maybe I can give you a more insightful answer if you can give me a specific example where a designer has to choose between one extreme or the other (or find the right balance)? For what it's worth, I admit to being a pretty conservative designer (though that doesn't describe me politically).
As a PM, I guess naturally I'm looking at it strictly from a product context. So I'm always trying to anticipate whether a new flow, or UI element, or feature will be good for my audience. In a perfect world, the design would conform to every person's mental model perfectly, in their own unique way. Of course, that's theoretical.
But sometimes people want, or enjoy being surprised with an experience they've never seen before. When is that appropriate? I feel like the easy answer is to say "test it, quantify it, whatever yields the highest results in the winner". I don't like to frame design problems in that context all the time though.
I suspect you would agree that there's not a single universal answer to that question, so forgive me if I sound like I'm punting a bit on anything definitive. However, it just so happened that this morning I read a piece at The New Yorker about how Netflix balances its formidable data resources with human judgment when it comes to making its original programming decisions. When programming chief Ted Sarandos was asked about this, he said:
“It is important to know which data to ignore,” he conceded, before saying, at the end, “In practice, its probably a seventy-thirty mix.” But which is the seventy and which is the thirty? “Seventy is the data, and thirty is judgment,” he told me later. Then he paused, and said, “But the thirty needs to be on top, if that makes sense.”
I like that formulation, personally. My thinking has always been, "We use data to inform the process, but in the end the product is for humans, so a human needs to make the final decision."
My answer has probably drifted a bit too far into the man v. machine arena to be really relevant to your original question, though. I think what you're asking is how you know when people are ready for a new approach. I think that has everything to do with knowing who your user is, and what their tolerance for novelty is. Hope that helps.
Hi! I'm such a big fan of your work! It has the world to do with the designer I am today and I'm super thankful.
Perhaps the thing the resonated with me the most from the work you did/talks you gave was the idea of Minimal Input, Maximum Output.
Where did the idea come from? Does it have anything to do with Buddhism?
@Nir: I'm not sure where that idea came from to be honest. But I think about getting the most out of the least quite a bit. When I was at the Times I talked a lot about trying to achieve "a maximum of elegance with a minimum of ornamentation," which not only fit the Times brand really well but was an extension of my whole approach to design. After all the name of my site has been Subtraction.com—a kind of obvious nod to minimalism—for a long, long time.
This is a dumb question, but I'm just wondering your opinion since I encounter this frequently and was a huge fan of your book on grids for web. What do you have to say to designers who are opposed to using grids?
@Jacob: Not a dumb question at all. I'm obviously a big believer in using grids; I tend to feel lost when I'm not using one. But I'm not really dogmatic about whether everyone needs to use one or not. I tend to think that what works for you, works for you. That said, I rest assured in the knowledge that even if a designer thinks he or she doesn't design with a grid, they really are. A grid isn't just a tool for designers; it's a subconscious expectation that the audience/reader/user brings to any design solution. So whether you say you do or not, you're still using a grid.
I'm curious to hear: when you say that you encounter this frequently, are you actually meeting/working with designers who are actively advising you not to use grids?
I think I feel the same way as what you're saying, once you put 2 elements on a page, they have some kind of relation to each other, so these designers are essentially making a grid as they lay things down. It sounds like that's what you're saying. The issue I have with that is when they don't follow the structure they've begun establishing.
No one's actually advising me not to use a grid, but when I've talked about it with designers at various places I've worked in the past (or just design friends), some people will say they don't need them. It's a hot issue on my mind whenever I see grids not being followed where they already exist, because it makes sites harder to update for future designers when there isn't consistent spacing.
Usually these conversations come up when people ask me for feedback and the most obvious fixes I see are adding structure by aligning objects more to a grid, then the person I'm reviewing either seems to not understand how grids work and/or thinks they just don't need to establish that structure and follow it for all their pages.
Some very talented designers produce wonderful work without any substantial adherence (or understanding) of grids. You can't argue with that. There's nothing inherently wrong with a designer's work just because he or she does not use grids—the absence of a grid does not make a wonderful work less wonderful somehow.
On the other hand, learning how to use grids is, for most of us, a great method of becoming a better designer. It's just a really valuable, useful, rewarding tool for almost any designer. And, I would say, there are lots of designers who would do much better work if their practice was underpinned with a nuanced understanding of how grids work.
So I dunno maybe some of those designers you work with who don't use grids are geniuses who don't need them. Or maybe they're not! I'm pretty sure I know which classification I would put money on if I were a betting man. You?
Yea, I think that's the best approach, that it's important to learn how grids work, then afterwards decide whether to use them or not. I think that applies to most best practices in any craft.
The only real problem I encounter from people not using grids is when it's a large group of designers are making pages for a site and someone doesn't follow the grid so there needs to be custom code for that page, and other globally used elements / widgets don't fit, which then cause other issues that need custom fixes + custom code—which is a little more of a team work flow issue than something a single designer would have to deal with on their own.
Team work flow is a huge issue in design production. Someone should write a book about that!
I'd like to know your thoughts behind simultaneously running a blog that is quite based around your personality and interests, while at the same time not having much in terms of your design work online? Is it that you more of a manager now? You strike as someone who still makes things, so I guess this is me asking why we can't get some awesome case studies of some of your work :)
@Anthony: That's a great question that I'm actually realizing no one has asked me before. I think the main reason I don't have my work up as an online portfolio is that it takes a lot of time—I think every designer would agree that putting together your own portfolio is one of the hardest design problems out there.
Also, I suppose I'm lucky in that I haven't really needed to get hired for work based on a portfolio in a number of years. That doesn't mean I shouldn't have a portfolio available; I probably should nevertheless. I guess I'm mostly just lazy!
That said, I do keep telling myself that I want to create a directory of all my projects over at Subtraction.com someday soon. Not quite a portfolio, just an index of things I've done that people can try out. One day.
Excited about the new book. You're definitely one of the more active designers that I follow on blogs/social media and have always written/posted really insightful but accessible stuff, so I just want to say "thanks" and "please keep it up!"
You've written some stuff about using Sketch and Photoshop's "largely useless features" for interface design. What's your typical workflow like these days? What are you spending the most time on at Wildcard or side projects?
@John: Thanks for the questions.
I spend a lot of time in Sketch. I'm a huge fan. Most everything I design, whether for native apps or for the web, starts there. I'll break out Photoshop or Illustrator to create assets for what I'm doing in Sketch, but I rarely do any actual UI design in those applications though.
That said, I'm doing more and more design with a product that I've been working on with Adobe called LayUp. It's an iPad app that turbocharges the brainstorming stage of the design process—there's a video at that link that shows how fast it can be to get an idea out of your head, onto the iPad screen, and then pushed off to one of Adobe's desktop apps. I use it to capture new ideas really quickly. The Adobe team has been phenomenal in building it, and I'm hoping that a public beta will be out pretty soon. It's starting to change up my workflow, and I think it will do the same for lots of folks.
As for what I spend most of my time on: Wildcard for sure. We bit off a huge challenge there, and there's tons of work to be done until we can say we're even halfway there. It's also the most fun of all my projects in the sense that I'm working with a great design team (my colleague Steve Meszaros and a freelancer) and a phenomenal engineering team. In fact, we're hiring another designer if anyone out there is interested.