the experts

Andrew Anker is a partner at August Capital (www.augustcap.com), a venture capital firm in Menlo Park, CA. He focuses on internet-related investments, and has funded sites like Emode, Listen.com, Ebates, and Evite. He was previously the CEO and co-founder of HotWired. Andrew has also worked as a programmer and an investment banker.

Adam Berliant is a Group Manager at Microsoft, where he oversees web development for Windows Media. He was previously the lead product planner for the MSN programming team. Before the web, he was a newspaper reporter in Tacoma, WA.

Carrie Bickner is a digital librarian with the New York Public Library. She's an active proponent of web standards, and the online style guide she produced for the NYPL is widely referenced by other sites transitioning to XHTML.

Hilary Billings is the Chairman and Chief Marketing Officer of RedEnvelope (www.redenvelope.com), a specialty gift store. She was previously Senior VP of Brand Development and Design at Starwood Hotels, where she oversaw the development of the W Hotels. Before that, she was VP of Product Design and Development at Pottery Barn, where she was in charge of directing and developing the design of all product lines for the stores and the catalog.

Doug Bowman is founder and principal of Stopdesign (www.stopdesign.com). He was previously Network Design Manager for Terra Lycos, and Design Director for HotWired. He works across media, designing for print and the web.

Rick Boyce is widely regarded as the father of the ad banner. He was a founder and Senior VP of Advertising Sales at HotWired, which introduced the ad banner to the web in 1994. He later served as the VP of Advertising for Lycos, and the president of IGN Entertainment, a network of sites targeted to gaming enthusiasts. Boyce was a founding board member of the Internet Advertising Bureau (IAB). Before the web, Rick was a vice president at the advertising agency Hal Riney & Partners in San Francisco.

Martha Brockenbrough is the former Managing Editor of MSN.com. She's now the principal of Martha Bee Productions (www.marthabee.com), a content and web consulting firm that caters to small businesses in Seattle. She writes a humor column for the online encyclopedia Encarta and another column on motherhood (The Mommy Chronicles). Before the web, she was a high school teacher and newspaper reporter in Tacoma, WA. Her first book, It Could Happen to You: Diary of a Pregnancy and Beyond, was published in 2002.

Sheryl Cababa is a designer for Microsoft, where she focuses on web and product design. Previously, she designed e-commerce sites for Getty Images.

Kris Carpenter is VP of Operations for Grand Central Communications, Inc. She was previously the VP of Excite Products & Services at Excite@Home, where she oversaw product development and engineering. During her five years with Excite, Inc and Excite@Home, Kris also held VP of E-Commerce Products & Services and Sr. Director of Search & Directory Products & Services positions.

Jason Cook is a former producer of Webmonkey. Previously, he was a product manager for HotBot and a production engineer for HotWired. He writes frequently about technology for Webmonkey and Wired magazine.

Cate Corcoran is the former Director of Online Communications for PeoplePC. Before that, she was the Executive Editor of HotWired. Most recently, she worked as a content specialist on the massive redesign and content overhaul of eBay's help system.

Greg Dotson is the Chief Information Officer for Guru (www.guru.com), where he oversees product development and architecture. Previously, he was CTO of Adam.com.

Esther Drill is the co-founder and Editor-in-Chief of gURL.com, the No. 1 site for teenage girls. She's written two books for gURL: Deal With It and The Looks Book.

Janice Fraser is a partner with Adaptive Path (www.adaptivepath.com), a user experience consultancy in San Francisco. She also teaches at S.F. State's Multimedia Studies Program. She started her web career at Netscape, where she pioneered consumer web applications. Before the web, she was managing editor for IDG Communications.

Jim Frew is a designer who splits his time between print and the web. He was previously Design Director at One and ThirdAge, and a designer with HotWired and Wired magazine.

Jesse James Garrett is the author of The Elements of User Experience (New Riders) and a partner with Adaptive Path (www.adaptivepath.com), a user experience consultancy in San Francisco. His site, jjg.net, is a popular resource for information architects, many of whom use his Visual Vocabulary, an open notation system for information architects.

Margaret Gould-Stewart is the former Senior Director of Network Design & Integration for Terra-Lycos. Prior to that role, she was General Manager and VP of Media & Community Development for Tripod.

Lara Hoyem is the senior marketing manager for BabyCenter (www.babycenter.com).

Mark Hurst is the founder and president of Creative Good (www.creativegood.com), a web consulting firm focused on improving the online user experience. His clients have included Blue Cross/Blue Shield, Gateway, Macy's, Nokia, Disney, MetLife, and Procter & Gamble. More than 30,000 people subscribe to his Good Experience newsletter.

Luke Knowland is the principal of LGK Productions (www.lgkproductions.com). He was previously Director of Web Production and Development at VolunteerMatch. Before that, he was Director of Product Development at Eyetide Media, interface director at ClearStation, and a technical designer for the @Home Network. Before that, he was a producer of Webmonkey.

Mike Kuniavsky is the author of Observing the User Experience, and a partner with Adaptive Path (www.adaptivepath.com), a user-experience consultancy in San Francisco. Previously, he established Wired's User Experience Laboratory, and worked on some of the web's earliest ecommerce sites.

Hunter Madsen has led the marketing efforts for several innovative web start-ups. He was VP of Marketing for Wired Digital, MoodLogic Software, and ImproveNet, before heading up product marketing at H Corporation, a provider of Internet-based data services. Madsen originally began his career at the advertising firm J. Walter Thompson, where as a Senior Partner he founded and directed JWT/Interactive, and developed pioneering online marketing programs for Sprint, Sun Microsystems, the California Board of Tourism, and others.

Matt Margolin is a web consultant living in Oakland, CA. He writes frequently about the web, and is at work on a book about web accessibility. He's also executive editor of the music site, Angry Coffee, and a former senior editor of Webmonkey.

Lance McDaniel is the VP of Creative for SBI and Company, a web consulting firm based in New York City. He was previously VP of Creative for Scient in London, Director of Client Services for iXL in San Francisco, and an account manager with Organic Online in San Francisco. During his eight years working on the web, Lance has helped build and manage sites for a variety of clients, including Disney, Harley Davidson, Levi's, Sara Lee, Starbucks, Star Wars, and Virgin Atlantic.

Noah Mercer is the Chief Technology Officer of Kalat Software. He was previously Chief Technology Officer of Nextdoor Networks, a local services start-up. Before that, he was Director of System and Software Design for The New York Times Electronic Media Co. and Manager of Systems Development for The Washington Post/Digital Ink.

Peter Merholz is a partner with Adaptive Path (www.adaptivepath.com), a user-experience consulting firm in San Francisco. Previously, he was Creative Director at Epinions.com, and a consultant with San Francisco's Phoenix Pop. He lectures frequently on design, information architecture, and site strategy.

Jim Morris is the former Director of Software Engineering for Fogdog Sports and Global Sports, Inc (now GSI Commerce).

Steve Mulder (www.muldermedia.com) is the Manager of User Experience at Terra Lycos, where he leads a global group of information architects and usability researchers focused on increasing revenue by improving the user experience. He was previously an Experience Lead and Information Architect with the web consulting firm, Razorfish.

Peter Naylor is the VP/GM of Advertising Sales for iVillage. He was previously a VP of advertising sales at Terra-Lycos. Before the web, he sold advertising at Vanity Fair and Spin magazines.

Wendy Owen is a principal with Giant Ant Design (www.giantant.com). She was previously the Director of User Experience at Guru, and a senior producer with HotWired, who founded the site Animation Express.

Derek Powazek (www.powazek.com) is the author of Design for Community: The Art of Connecting Real People in Virtual Spaces. He's currently the Director of Online Projects for the Independent Media Institute, a nonprofit company in San Francisco that publishes AlterNet.org. He previously worked with Electric Minds, and has consulted for many corporate clients, including Nike, Netscape, and Sony. He also runs several independent content and community sites, including {fray} and SF Stories.

Josh Quittner is the Editor of Business 2.0. Previously, he was the managing editor of Time Digital. In 1995, he founded the Netly News, Time Inc.'s first venture into original, independent online content, and he later edited Time.com. Over the years, he has written frequently about the web in Time and Wired magazines. His influential essay, "Birth of the Way New Journalism," appeared on HotWired in 1994.

Nadav Savio is a principal at Giant Ant Design (www.giantant.com). He was previously an independent interface designer and a design engineer for HotWired.

Randi Shade is the founder of CharityGift.com, which simplifies the process of making donations in someone's name. Previously, she founded the Texas Commission on Volunteerism and Community Service (under Govs. Ann Richards and George W. Bush), where she was responsible for launching AmeriCorps. She's also worked for Procter and Gamble and Teach for America.

Emily Simas is a former Product Manager for BabyCenter, where she oversaw their multimillion mailing email program. She was previously a content manager at an online education start-up, and before that, a Kindergarten teacher. She also runs leadership programs, and facilitates workshops and brainstorming sessions for corporate and nonprofit clients.

Srinija Srinivasan is the VP and Editor in Chief of Yahoo! She joined Yahoo as employee No. 5 in 1995, and was responsible for the organization and evolution of the Yahoo! Directory. Since then, she has managed a team of editors and directed the development of Yahoo!'s original content.

Pamela Statz ([e-mail]) is a freelance web developer based in San Francisco. She was previously Web Production Manager at Lucasfilm and Production Director at HotWired. Most recently she has worked on a variety of projects from writing, teaching, producing web-based software applications, and building web sites for grass-roots political organizations.

Taylor is the lead interface designer for Secret Level, and principal of Captain Cursor Creations. He was previously a partner at Red Industries, a web development shop in San Francisco, and a design engineer for HotWired.

Evany Thomas is the managing editor of Webmonkey. She's been building web sites since 1995, and her personal site was featured on many leading sites. She was previously a columnist for MSN.

Thau is the Director of Engineering at the All Species Foundation and author of The Book of JavaScript. He's been creating web applications since 1993, when he co-founded bianca.com, the first web-based community. He was previously Director of Engineering and senior scientist at HotWired. He teaches several courses on web technologies at San Francisco State University, and a graduate-level course on database-driven web sites at Mills College.

Michael Twidale is a professor of library and information science at the University of Illinois Urbana-Champaign. He specializes in user interface design and computer-supported cooperative work. He frequently leads workshops on web site usability design and usability testing.

Beth Vanderslice is the former General Manager of Lycos San Francisco, and former President of HotWired. Previously, she was a Vice President at H.W. Jesse & Co. a San Francisco investment banking firm. She's on the Board of Directors for Xilinx, Inc. (NASDAQ:XLNX) and the Bay Area Discovery Museum, and received her MBA from the Harvard Business School.

Jeffrey Veen is author of The Art & Science of Web Design (New Riders), and a partner with Adaptive Path (www.adaptivepath.com), a user experience consulting firm in San Francisco. He was previously Executive Interface Director for HotWired. He lectures frequently around the world.

Omar Wasow is the founder and CEO of BlackPlanet (www.blackplanet.com), the No. 1 site for African-Americans. He's also a TV Internet analyst for Newschannel 4 and MSNBC. In 1993, he founded the virtual community, New York Online.

Kristin Windbigler is the former Executive Producer of Webmonkey. She's currently a freelance web consultant, and based in San Francisco. She's also the founder of HITS, a non-profit offering technology education in rural Humboldt County, CA. Before moving webward, she was an award-winning newspaper reporter in northern California.

Jason Wishnow is the founder of New Venue (www.newvenue.com), the first curated showcase of movies made specifically for the Internet, and the Aggressively Boring Film Festival, the first film festival for the Palm Pilot platform. He speaks and writes frequently about digital video, and his award-winning film, Tatooine or Bust, was one of the first documentaries shot on mini-DV.

Indi Young is a partner with Adaptive Path, a user-experience consulting firm in San Francisco. She's been developing web applications since 1995, for clients ranged from technology start-ups to large financial institutions. Previously, she was a software engineer, focused on user interface design.

Jeffrey Zeldman (www.zeldman.com) is the principal at Happy Cog Studios, a web design consultancy, and the author of Designing with Web Standards (New Riders: 2003). He lectures and writes frequently about web design, and standards in particular. He also runs the popular site, A List Apart (www.alistapart.com), which offers advice "for people who make web sites."

Tim Ziegler is the founder of Family Album.com. He previously founded LostRock.com, which helped independent musicians promote themselves online. Before that, he was Executive Editor of NotHarvard.com (later Powered.com), and Senior Editor of Webmonkey.

expert advice: what have you learned about the web?

"People don't click if they're not sure what they're going to get. That's why it's important to have clear labels."

Martha Brockenbrough

"The biggest mistake you can make on the web is thinking you're done."

Andrew Anker

1. The users call the shots. Users are in control, not you. So you have to focus on what they need, not what you want to do.

   Mike Kuniavsky, author of Observing the User Experience, has watched company after company learn this lesson. From 1999 2000, he did user research for more than a dozen Internet start-ups.

   "Every company I worked with failed," he said. "And they all failed for the same fundamental reason: They hadn't thought about the value they were giving people and whether people wanted that value."

   "So the main thing I've learned is that before you make a product, you need to know that it satisfies someone's need, and that someone will want to pay for it," he says. "This is true for just about any business, but it's especially true for web sites."

   "You have to respect your audience," agreed Jason Wishnow, founder of the film site New Venue. "This is something I picked up as a film director, but it applies to web design as well. You don't need to pander to the lowest common denominator, but you do need to acknowledge that people will visit your site from different computers running different browsers, with different plug-ins, and with different levels of savviness when it comes to interface. You can be creative and accommodating at the same time."

2. Less is more. "I have really learned that less is more," says Janice Fraser, a partner with Adaptive Path who has developed many multi-million-dollar sites. "Doing a few things really well is far more important than having so-called full-featured web sites."

   A simple, pared-down approach benefits both the organization and the user. "The first lesson I learned was that less is more not only in staffing, but in what you put on your web site," said Josh Quittner, who founded the NetlyNews for Time, Inc. in 1995, and is now editor of Business 2.0.

   "Initially, we had no respect for people who were on narrowband connections and 90% of our audience was on narrowband connections. We'd give them junky pages with sound and confetti and huge images. They'd take 45 minutes to download, and we didn't care, because we could do it! We'd have six people producing something that would cost $15,000 and would be seen by eight people. It was crazy. It was cool. It was so stupid!"

   Naturally, he said, it proved hard to build an audience. "So the lesson we learned was: Simplicity. It's not about how much you can put in; it's about how much you can get rid of."

   "Of course, we should have known this. I mean, that's what programming is all about. That's what information technology is all about. That, in fact, is what good writing is all about. It's what you do at Time Magazine: You just keep removing words until you've got something that's so lean, and so mean, and so smart that it's as perfect as you can get it."

   "We should have applied that reasoning to what we were doing on the web...But of course, we were having too much fun."

3. Pay attention to what's working. The web gives you unprecedented opportunities to learn what's working (and what isn't) on your site and in your business. Take advantage of it!

   "Quantitative research on the Internet is so luxurious," said Adam Berliant, a Group Manager for Microsoft who oversees the WindowsMedia web sites. "I cannot pick up an issue of Newsweek and tell you which article was read the most. Or how much time people spent on each article. Or which headline was the most effective. On the Internet, I can tell you what 100% of the people who used this site did."

   "You end up with this ever-building cumulative picture of what works and what doesn't work on a particular web site," Berliant said. "And the beauty of the web over software is I can take that learning and act on it tomorrow."

4. Your site must evolve. In just about every other industry media, retail, software, you name it you produce a finished product and hand it off to customers. But the web is different. Successful site owners learn quickly that the real power of the web is your ability to adapt your site to better serve users.

   "It's the process, not the product," says Andrew Anker, a partner with August Capital. "In almost every other area of business certainly in technology the focus is on the product. But on the web, it's really the process. The easy part is getting the product out. The real challenge is figuring out what you did right and wrong, and changing quickly. The biggest mistake you can make on the web is thinking you're done."

   "A lesson I've had to learn just about every day is you can't focus enough on the boring day-to-day execution," says Omar Wasow, founder of BlackPlanet. "It's important to focus on continuous improvement. The difference between success and failure is in these subtle changes."

5. Amazon gets it right. "One thing I've learned in the last seven years is that Amazon keeps doing everything that you should do, when it comes to website design," said Peter Merholz, a partner with consulting firm Adaptive Path. "You can do a lot worse than starting by copying them."

6. People are the problem. The greatest barrier to web site success isn't technology or funding or usability design. It's people. Organizational politics and inter-departmental turf wars cause companies to stumble more than anything else. "Corporate politics and corporate culture are the biggest problems I have to deal with," says Jesse James Garrett, an information architect and partner with Adaptive Path. "Bigger than any information architecture problem, bigger than any design problem, bigger than any technology problem."

7. Like begets like. Anyone who's participated in online communities or even published a personal home page has witnessed this phenomenon: what you put out into the world is very often what you get back. "Like begets like," says Derek Powazek, author of Design for Community. "If you put up a web page that says, 'All Republicans are stupid,' and then add a forum, then the responses you get are, 'No. You're stupid.' If you put up a web page that says, 'Here's this emotional rant about being a teenager and being lonely,' you will get back emotional teenage angst. Anything you put out gets amplified and comes back to you. That's the number one thing I've learned."

8. Pull-down menus are not for navigation. "I've learned that you should never use pull-down menus for anything other than filling in forms," says Peter Merholz, a partner with Adaptive Path. "They should not be used as navigation elements."

   'Pull-downs are a highly effective way of burying information that you want your user to see."

9. Section names should be clear, not clever. "People don't click if they're not sure what they're going to get," says Martha Brockenbrough, former managing editor of MSN.com. "That's why it's important to have very clear labels."

expert advice: what's the biggest mistake you see web sites make?

"Sites aren't paying close enough attention to hierarchy. When the user arrives... they have no idea where to start."

Doug Bowman

"Using their site as a teaser area for future, unformed plans, rather than for current offerings."

Srinija Srinivasan

Everyone in the web industry's made their fair share of mistakes, so they can easily spot where others are going astray. What are the biggest mistake that sites are still making?

1. Thinking that they are their users. "The number one misconception that clients have is that they are the target audience for the site," says Lance McDaniel. "But they are not, and their wife is not, and their kids are not. So the biggest misconception is that their opinion matters. We ask them, 'What's your user's opinion? Because we're designing the site for your users, not for you. And that's why you're paying us.'"

2. Not setting goals. "Often, a client's first question is 'How much is this going to cost?'" says Martha Brockenbrough. "But the real question is, 'What do you want this web site to do? What do you want it to do for your business?' I primarily work with very small businesses. And they usually have no idea what a web site can do. They just feel like they should have one. But that's the biggest mistake you can make! You should have very clear goals for what the web site can help you achieve."

3. Lack of focus. "Lack of focus is the major, major, major mistake I see," says Dave Thau, author of The Book of JavaScript and former senior scientist for Nerve and Wired. "Because the medium's flexible, you get the feeling you can do anything. But you only have so many hours in a day." And even if you finish what you set out to do, it isn't always the best thing for your business. Sites often stumble when they're "trying to do too much," says Jason Cook, former product manager for HotBot. "Often, the web site that's fastest, wins. And speed isn't just about download time, but helping people solve things more quickly. You should think about the one or two things that customers want to do, and center your site around that."

4. Obscuring their main purpose. "As silly as it sounds, a lot of sites don't put their primary purpose on their homepage," says Mark Hurst, founder of consulting firm Creative Good. "Or it's there, but it's obscured."

   "The best counter example of this is Google. It puts its primary purpose first, and doesn't distract from letting you know what it is. What's Google? It's a search site. And I don't have to tell you that, because it's kind of hard to miss."

5. Skipping straight to design. "The biggest mistake that I see repeated most often is that people jump too quickly into the design process," says Indi Young, a partner with Adaptive Path. "Because design is something you can see, it's interesting to everyone. Everyone wants to jump to that first."

   "Also, everybody has an opinion about it. Everybody has opinions about colors and fonts and layouts and the balance of the screen. But they skip the functionality stage and start designing backwards. They put the cart before the horse."

   Continuing the analogy, she goes on to describe the cart that such a team might build: "They figure out that the cart is going to have two wheels, and those wheels need to be toward the front, because they're prettier up there. And one wheel is going to be bigger than the other wheel, because we want variety. And the bottom of the cart is going to be made out of a metal grid. So now, here you have this lopsided cart that's really hard to harness a horse to, and you can't hold anything in it, and everything falls out the bottom."

   "Sorry," she says with a smile. "I love analogies."

6. Too much jargon. "One of the hardest transitions for people in a given business to make is from the mind of the seller to the mind of the buyer, and from the language of the seller to the language of the buyer," says online marketing expert Hunter Madsen. "So what you often see in web sites is jargon sometimes hilariously piled upon itself."

7. Lack of a clear hierarchy. "More often than not, sites aren't paying close enough attention to hierarchy," says Doug Bowman, principal of StopDesign. "When the user arrives on a page, they have no idea where to start. Or if they do, the hierarchy's reversed compared to what it should be."

8. Prioritizing short-term over long-term goals. "A lot of companies will think in terms of the short-term, quick financial gain instead of the long-term relationship building with users," says Steve Mulder, manager of user experience for Terra-Lycos.

   Information architect Jesse James Garrett agrees. "The worst mistake you can make, strategically, is racing for short-term gains without thinking about the long-term. Running a marathon is different from running a sprint. The web site is not a sprint. The web site is a marathon...One of the reasons people have to hire me is because they didn't pursue a clearly articulated strategy for any length of time. They were trying to run a marathon like it was a sprint. They got a couple of miles into it, they were exhausted, and they couldn't figure out why."

9. Blindly trusting web consultants. Handing off responsibility to an outside firm is always risky. "Consultants make you feel like you can trust them, and that they're going to do whatever is in your best interest," says Pamela Statz. "And in most cases they are. But sometimes they'd rather do stuff that's new and fun. I've seen this happen many times with web development companies."

   "If you're going to pay someone a lot of money to build your web site, it's your responsibility to pay very close attention to the details and decisions regarding the design and technology," Statz said. "Your web consultants cannot read your mind and they cannot possibly understand the needs of your company the way you do."

10. Confusing error messages. Left to its own devices, your server will spit out confusing messages when something goes awry. But sites can customize these messages, if they bother to. "Poor error messaging" is the bee in Luke Knowland's bonnet. "You should realize that someone's going to make mistakes and allow for it. Prompt them about what to do next. This is so easy to take care of it takes 10 15 minutes!"

11. Generic design. "We don't buy dull books or watch plotless, indifferently photographed movies. We don't go out of our way to buy generic products," says Jeffrey Zeldman. "Yet many site owners seem unaware of the importance of creating a strong visual and verbal identity. Of course, your site must be usable. But if it is indifferently written and designed, it will not engage anyone; if it lacks a memorable and appropriate identity, few will bookmark it or remember to visit again. The web is not Muzak."

12. Pretending to be something they're not. No one sees more web sites or more mistakes than the editorial team at Yahoo!, which evaluates every site submitted to their directory. Their biggest pet peeve? Sites that claim to offer more than they actually do. "The biggest mistake I see websites make is using their site as a teaser area for unformed future plans, rather than as a relevant, functional hub for current offerings," said Srinija Srinivasan, editor-in-chief of Yahoo!. "Beyond other media, the web is differentiated by being immediate and interactive. Great websites incorporate that rather than ignore it."

expert advice: what are the red flags that a project is trouble?

"It's easier to collaborate when you're in the same time zone."

Nadav Savio

"Key decision makers who are battling each other. If the marketing VP can't stand the engineering VP, it's not going to end well."

Kristin Windbigler

After working on the web for a while (after working anywhere for a while) you start to pick up the signals that a project is going to run into problems. What red flags do industry experts look for?

1. An unrealistic schedule. "An unreasonable timeline is, to me, the biggest red flag," says Lance McDaniel. "Because if it takes eight weeks, it's going to take eight weeks. No matter what you promise, no matter what the penalty clauses are, no matter when your marketing campaign launch is. If it takes eight weeks to code 8,000 pages in HTML, that's how long it takes."

2. Unrealistic scope. A web project that's trying to do too many things at the same time, without sufficient resources, is setting itself up for trouble. "Unrealistic scope is the biggest red flag," says Carrie Bickner, a librarian and web specialist with the New York Public Library. "I just had a group of librarians come to me with a project idea. I looked at their outline, and I said to them, 'Boy, this is really great, but it's actually five different projects.' So my job is to parcel all that out, and say, 'Now, these four projects would each cost a million dollars. But this one, that might be about $60,000. Maybe there's a grant we could find to do this one small part of it.' Yes, that's usually the problem: An unrealistic sense of scope."

3. Missing early deadlines. If a team doesn't hit the first deadlines on the schedule, it's a warning sign that something's not working. "Missing a lot of early deadlines that's a key indicator," says Greg Dotson, Chief Information Officer of Guru. "Maybe the team doesn't have enough information. Maybe they're not functioning well together. Maybe they don't have enough resources. Or maybe they have too many people on the team, and they're not splitting up their roles properly.

4. A leader who can't say no. "If your product development person can't say no to people who ask for features, that's a red flag," said Peter Merholz. "You need someone who can say 'No,' because what's being requested doesn't match the vision of the product. When it comes to a web product, probably the single most valuable thing an organization can have is a product manager who can step back and see the whole picture: the design, the technology, the business. A product is most likely to succeed when there's a single vision driving it."

5. A vague or poorly defined product. "The first thing I look at is the quality of the definition of the product," says Noah Mercer, former software director for The New York Times and The Washington Post. "An ill-defined product just makes me extremely nervous. An ill-defined product with no one around to define it makes me more nervous. An ill-defined product with someone around to define it who doesn't have the time or skills to do it makes me want to run away in panic."

6. A geographically dispersed team. "Distance, I should say, is a big red flag," says Jim Morris, Director of Software Engineering for Fogdog sports. "If I can do a project with me and my engineer, it has a high rate of success. if I have to work with someone back east [Morris is based in California], it's going to have a lower rate of success. If it involves a systems administrator from back east, even lower because they're very busy and they get distracted very easily. "It's easier to collaborate when you're in the same time zone," says Nadav Savio, principal of Giant Ant Design. "There's a direct correlation between how many time zones you're off and how much harder it is."

7. Imbalanced or uncollaborative team. "When one department or discipline has too much power, you have problems," says Luke Knowland, former Director of Product Development for VolunteerMatch. "Web development done right is so interdisciplinary. Everyone has to be responsible and accountable to each other. It's important to have respect. But engineering teams and design teams almost never respect each other.

8. Dependence on a new technology. The biggest red flags for Taylor, a design engineer who's worked on many cutting-edge sites, is reliance on unproven technologies. It's a problem, he says, "if the success of the site or the entire business hinges on a certain deal coming through, or a certain technology being adopted. Beware new technology. Most new technologies, like most new businesses, fail."

9. Turf wars and personality conflicts. Successful web projects require collaboration. But if individuals or departments are fighting for dominance, that gets in the way. "Most of my red-flags are personality-related," says Indi Young. "One is turf wars. That happens a lot between engineering and design, engineering and marketing." Personal conflicts can also get in the way. It's a problem, when you have "key decision-makers who are battling each other," says Kristin Windbigler, former Executive producer of Webmonkey. "If you go into a meeting and it's obvious that the marketing VP can't stand the engineering VP, it's not going to end well."

10. Unclear reporting structure. "A huge, huge red flag is when there's not a clearly organized chain of command for who gets to make decisions," says Tim Ziegler. "The lack of a clear decision-making structure and someone with the authority to mediate conflicts is just death." It's a problem in any company, he says, but it's amplified on technical projects: "There's always competition for backend resources and for development resources. And someone has to mediate that. Otherwise, you're left to fight it out in the trenches."

11. Unrealistic expectations. Sometimes, companies have expectations for a site that far outstrip its ability to deliver. "When clients say, 'We want to change our brand image, so build us a new site.' That's a red flag to me, because you're not going to change a brand image through the web alone," says Lance McDaniel. "If a client isn't taking into account the $350 million they're spending elsewhere, and they expect your $100,000 web site to change the world, that's usually a red flag."

12. Crazy visionaries. "I tend to stay away from companies where projects are being led by crazy visionaries," says Kristin Windbigler. "I've already seen behind the wizard's curtain."

expert advice: one piece of advice for someone launching a web site?

"Get over yourself! This is not about you. You need to think about your user and their goals."

Cate Corcoran

"Keep it simple. Start small, learn from your mistakes, and grow incrementally"

Omar Wasow

Hindsight is always 20/20. And every web veteran would do things differently were they relaunching past sites. Here's their advice for you as you launch your web site.

1. Know your user. This is probably the biggest single piece of learning throughout the industry. Almost every successful web site starts with a strong sense of who it's for. "You have to be really truthful about who your customer is, and what your business stands for in the eyes of that customer," said Hilary Billings, chairman and chief marketing officer of RedEnvelope. "Know who your customer is, and what they need from you. And let that guide you. Don't try to outsmart your customer. Build a business for them."

   "Know who you're building the site for, and why you're building it," says Mike Kuniavsky. "Know that very, very well. And give yourself enough time to know that before you pick up Dreamweaver and start building the site."

2. Build a site for the user, not you. "Honestly, my advice would be something like 'Get over yourself,'" said Cate Corcoran. "This is not about you. You need to think about your user and their goals." Similarly, you need to make sure you're building a site that someone needs. "Don't invent the gadget and then try to find a market for it," says Randi Shade, founder of CharityGift. "Find an unmet need, and develop a solution to meet that need."

3. Let your site evolve. Don't try to launch a polished, finished site. "Rather than try to build the perfect system, do something faster and fix it later," says Nadav Savio, principal of Giant Ant Design.

4. Know your business. It's less important to know the web than it is to know your own business. "Make sure that you know your business, and know your customers, and know what goals you're trying to accomplish with this web site because the web site is a tool for your business," says Noah Mercer. "If you have that stuff nailed down and usually you don't the web site is the easier part of things. The harder part is really knowing what you're trying to do."

5. Always make a plan. It's important in just about any endeavor, and it's crucial for web sites. "Take the time to plan," advises Lance McDaniel. "Spend twice as much time as you think you need to figure out what you're trying to accomplish as a business. Because all the problems that you don't solve up-front will add time during the build, and make it twice as expensive."

   "Do your homework," advises Adam Berliant, a Group Manager for Microsoft. "Building a website is not like sitting down at a canvas and painting a picture of whatever comes out of your head."

   "That's why so many dot-coms failed," Berliant said. "They didn't do their homework. They weren't sure who their customers were. They weren't sure if their goals were realistic. They weren't sure how it was all going to work. But you can take care of a lot of that up front, if you do your homework."

6. Start small and keep it simple. It's easy to get swept away with big plans for a big site. But on the web, smaller is usually better. "Keep it simple," advises Omar Wasow. "Start small, learn from your mistakes, and grow incrementally. It's really easy to spend a lot of money on something that's massively useless. So try to have real clarity about what it is you're trying to do, and do those few things well."

   Keeping a sharp focus is helpful in more ways than one. "Think small," says Josh Quittner, editor of Business 2.0. "Think small in every way. Create a web site that's really as simple as you can possibly make it. Make it as obvious as you possibly can, and don't expect that because you're in a space where 100 million people can see you that 100 million people will see you.

   The bigger your site is, the harder it is to get attention. But if you have a really wonderful, small, beautifully designed, simple-to-navigate, obvious site that provides real value to whoever you identify as your market, people will find it, and sooner or later it will take off."

7. Make your site easier to use. The easier you make it, the more people will participate, says Mark Hurst, founder and CEO of consulting firm Creative Good. "The web is too hard to use," he says "That's what's holding back businesses the companies that do business on the web. The key piece [they're] missing is the user experience. A quick and easy user experience. "

8. Copy your competition! You probably don't want to completely copy a competitor's site, but feel free to borrow! You definitely want to learn from what's out there, before you build your own. "Find a site doing something similar, and learn everything you can from it," says Evany Thomas, managing editor of Webmonkey. "View source. The web is all about viewing source."

9. Collaborate. The web requires a multi-disciplinary approach. And this means not just assembling a complete team, but helping them to communicate. "Do as much as you can to have all the disciplines being represented talk to each other," says writer Matt Margolin.

10. Mind the details. A lot of things small and large have to come together to create a successful site. You'll need to make a lot of decisions in the course of developing a web site. "Make sure that everything the user experiences on your site is the result of a conscious decision on your part that nothing is there by accident," advises Jesse James Garrett.

11. Test your site. No matter how many sites you've built, you can't know how a given site will be used until you see someone try. "Have your mom test it," recommends Derek Powazek. "My mom is my best beta tester. The smarter she gets about the web, the worse of a tester she is."

12. Make sure you have authority. Web projects are notorious for their convoluted reporting structures and unclear chains of command. When you take on a site, make sure things are clear. "For the project manager, make sure you have enough authority over the project," says Pamela Statz. "Before you get involved, make sure you're introduced to the team and to others in management as the person who's in charge."

13. Register variations on your domain name. When you're choosing your domain name, remember that people won't always type or spell things correctly. "Register all the misspellings of your domain name," advises Cate Corcoran. "And the dot-org, dot-com, and dot-net addresses too."

    A site that does it right? Crate & Barrel. "Crate & Barrel knows that no one knows how to spell the word 'barrel,'" Corcoran said with a smile. "How many R's and how many L's? So you can type in anything that's somewhat close to Crate & Barrel and still get to crateandbarrel.com."