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We had a great time catching up with many of you at last night’s GeekWire Meetup. A big thanks to everyone who came out to the event at the Zillow HQ in downtown Seattle.

Apart from the networking, the beverages and the games the highlight of the night was a chat between former Microsoft design director Bill Flora and Jonathan Sposato, the startup veteran and GeekWire chairman.

Bill Flora and Jonathan Sposato at the GeekWire Meetup

See a video of their discussion above, thanks to Akaash Saini, and edited excerpts from the conversation below. Photos of the evening are courtesy of Richard Wood. Thanks also to sponsors Microsoft Hotmail, Odin Brewing, and  Alexandria Nicole Cellars.

During the chat, Flora talked about topics including the spread of the Metro design inside Microsoft, his heroes in the design industry, advice for up-and-coming designers, and his favorite apps these days from the perspective of design — including a shout-out to his former Microsoft colleagues behind the Paper app for iOS.

Sposato: One of the things that I hear all the time, from having worked in software is this notion that designers are divas, that they’re kind of hard to work with, there’s a lot of drama. I’d like to know from your perspective, No. 1, is that true, and No. 2, from a designer’s perspective, what advice would you give to the non-designers in the office — engineers, marketing folks, program managers — in terms of how best to work with designers.

Flora: I think some of us are both right and left brain folks. I’ve been at Microsoft, and I’ve recently left, I was there for 19 years. Some of us need to be both right brain and left brain, work with both sides of the fence, and I enjoyed that part, I really enjoyed digging in deeply in some of the development capabilities, as well as being the designer, and at Microsoft being able to manage all those issues. So for me, it was a good experience, because I was able to handle all those dimensions.

But there was some really talented people that I really worked to insulate from the big corporate culture. We can still bring a lot of value out of them, if they can be insulated the right way. Just because they didn’t plug in perfectly with how things are done at Microsoft didn’t mean that Microsoft really couldn’t get a lot of value out of them, so as a manager I really tried to attract these people and let them work on Macs …

Sposato: Did anybody come after you?

Flora: No, not until after I left.

Sposato: We’ve gone from a time where UI design, user experience is very flat and simple, and that over time, culminating with things like Windows XP, Vista, everything has dimension and drop shadows and feels tactile, and it’s like a solid 3D object.

Now, it seems like we’re going back to simple again. … Why is that, and where are things headed?

Flora: I would say a lot of it is in reaction to the other, where you get something so rich, you want to stand out. For me, that’s been one of my motivations for design. With Encarta Encyclopedia, we had Windows 3.1 look and feel to deal with, and I didn’t want anything more than to get away from that as quickly as possible. People were arguing over how many pixel shadows we could have on the gray buttons. I just wanted to get rid of all of that.

And I would say a lot of the thinking behind Metro and this flat, clean, open world came in reaction to a lot of the shiny buttons in Apple, a lot of the glassy floors and brushed metal, using all these industrial design metaphors for software. I thought, software is mature enough now stand on its own, and we’ve got screen resolution now that can accommodate a lot more content, and we’ve got bandwidth that can handle content, so at some point, it felt like with some of these things, we can take a different approach.

And the approach really with Metro was taking some cues from just good print design, with good typography and good layout. You didn’t need a box around everything in print design. In software we started by 640×480 and we had to delineate all that space, and we put boxes around everything, and that’s how code worked. At one point we wanted to get out of the boxes. Let’s do curves! And the devs said, we can’t do curves. Finally, finally development was able to do curves for us, and then we were like, actually we don’t want curves anymore.

I think that some of the things from print design that had all this real estate, and you could accommodate more white space, and you could have more content, freed us up a lot.

I compare us to Apple a lot, because in a way it was trying to be a differentiation from that. We were so simple and clean and basic, you just have a few elements to work with, like typography and the content that you have, and the structure and the layout. Where do you get that emotion, that emotion that you get with a shiny button and a glassy floor and things like that? Well, now we’ve got more powerful platforms and we can bring motion into the experience. So having something flat, simple, clean, paired with good motion really allowed us to be something different.

Sposato: That’s another dimension altogether, the motion and the speed.

Flora: Huge dimension.

Sposato: A lot of us find the Metro design so radical, I don’t think it’s overstating to say that particularly for Microsoft it’s such a radical change. What are some of the risks for Microsoft having rolled out such a radical approach to something that impacts Windows?

Flora: Metro was a little more quickly adopted across the company than I thought it would be. I thought we’d be arm-wrestling everyone. One of the higher-order goals was to get Microsoft products to start to feel like Microsoft products — a family, it came from one company.

It’s set up where different groups do their own things, and you’ve got lots of variety of different designs. So one of the benefits of this is it does feel like it comes from one company.

Some of the risks are, I think, greatest with Windows, of course, because that’s the biggest behemoth and you’ve got all this legacy. So I think some of that risk was mitigated by the Windows team for Windows 8 by keeping their classic mode, and not making radical changes there, but doing more of the radical changes with the touch UI.  I think that’s one way the company is trying to mitigate that.

But to be honest, there might have been more risk to not do anything if you’re Microsoft at this point. The approach with Metro was more bottoms-up rather than top down. We worked with design teams around the company, and they really craved some direction, some leadership. If they felt like there’s momentum in this direction, they could talk to their leadership and say, well, instead of what you would like, there’s momentum behind this particular direction. So it empowered the design teams. And it was design principles that they all seemed to value and recognize, so it helped.

Sposato: When you look at the end result now, are there things that were missed opportunities, or that you wish had been done, that didn’t quite make it?

Flora: I would say Windows Phone is probably the best example of this Metro language being expressed, because they had a value system within that organization that allowed design and dev to iterate and iterate and iterate, and get it really refined. Because when you’re working with so few elements like Metro, the fit and finish has a much more important role to play, the craftsmanship is what also brings the emotion to it. Metro is on of those things that’s easy to do poorly, I think. You need to have the right eye, you really need to have the right level of craftsmanship. So I think that’s one of the biggest risks at the company — not every organization there is optimized to deliver on high-end fit and finish. They’re more optimized around delivering as many features as you can, and we have to cut some of this fit and finish stuff. So Windows Phone really had a different take and a different attitude. They really had to compete, so I think that’s what they embraced, more of that high-end fit and finish, which needs to be baked into the whole organization to work.

Sposato: What are your honest professional opinions of some of the work that other software companies are doing? What do you think of Google’s designs or Apple’s?

Flora: It’s interesting — I’m starting to see Google clean things up, and open things up and simplify things. It’s really great. It used to be, two or three years ago, Google was arguing over exactly what shade of blue should our link be. Now they’re taking some cues, like Metro did, from print, and for more real estate, keeping it really simple.

I do think the advent of mobile has really played a role in the approach people are taking to software user experience, because you’re forced to make things really simple to work. I think that played off well with some of the PC and desktop stuff. So I’m impressed to see Google out there.

Other things that stand out for me, there’s Paper, which is a new iOS app. Like Instagram, they picked one key activity and really did it really, really well. And it stood out. Clear is another UI on the iPhone that really stood out, because it didn’t use the iPhone system UI, it just went out on its own and tried its own world, its own system. So I admire people that really try their own thing, and do something a little bit new and different.

Sposato: number of people in the audience tonight are designers or budding designers, at various stages of their careers. What advice would you give them as they develop their careers and think about what they should work on to have the kind of career that you’re having?

Flora: I had a special career at Microsoft because I started really early on. When I got there I was designing dialogue boxes and toolbar buttons. One of my claims to fame is the Office indent toolbar button, if you’ve ever used that? It still lives! Would I recommend starting your career off at Microsoft and staying for 19 years? Not necessarily. It’s kind of a unique weird thing. …

Really I think a startup is an intimidating environment. If I were starting off, I would want to make sure I’ve got some mentors and some more experienced designers that can really show me the ropes. You can get lost in a startup, you can get lost in a big corporation, so I would look for people that can help mentor you, and trust in you and be a heat shield for all the crap that happens.

Sposato: If you could travel back in time and have dinner or coffee  and chat with any great designer or architect and really pick their brain and have them be your mentor, who might that be?

Flora: That’d be pretty easy. Probably Buckminster Fuller, just because he’s a maverick and a genius. He approached things differently, he didn’t just extend what was already there, he took a big leap and tried something different. And he was a crazy guy too. So probably Buckminster Fuller, or Ray Eames.

Sposato: How about someone present day?

Flora: That’s harder. I thought you might ask that. Yves Behar, Jawbone, Jawbox. Saul Bass. I love motion and graphic design, and he was one of the first pioneers there.

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