The key motivators for online holiday shopping are selection, shipping and convenience, and price. Each of these factors can be exploited on your website.

Selection. This means both the wide array of products you can get fron any given vendor, but also thechance that they’ll stock stuff that wasn’t available locally. Don’t be surprised if you get seemingly odd orders from far afield because you happen to still have stock. Once hot products begin to appear, it may be worth pay-per-click marketing to target the vast, but transient, search volume they tend to create.

Shipping Hassles. If you’re buying gifts for distant friends and family, it means you’re automatically making extra stops– wrap the gift, take it to the post office, buy shipping materials. When you order online, it’s just a matter of de-selecting the “billing and shipping address are the same” box and going. This represents an opportunity to upsell gift-wrapping or specially-timed delivery services. In addition, it’s a great trust-building location. Tell me exactly when I can expect my order, and it eliminates any fear I had about pressing “Check out”. Now may also be the best time to consider accepting international orders– a US store getting an order from the UK to ship to a US address may simply be trying to minimize shipping delay and cost on a gift purchase, not a fraudulent use of a UK card.

Price. Everyone’s figured out it’s worth checking prices online, at least, before buying. However, customers have been burned before– they’re more and more aware of what the total cost of an online purchase is– which vendors charge tax, which ones gouged them on shipping last year. While some retailers do “design for comparison shopping engines”– with gimmicks like prices which vary depending on which referer you follow, or hidden charges, greater interconnectedness of customers means that you won’t get away with it for long. If you merely want to please the low-price market without too much complexity, a simple guarantee, prominently marketed, can get the trust factor in a hurry. Circuit City has been out of business for half a decade, and I bet you still recall their 1980s ads featuring the the child being reimbursed after finding his hard-earned Walkman was available cheaper elsewhere.

But aside from the big draw factors, there are some issues that online marketers really need to consider.

The poor economy and resurgence of layaway may have created a difficult-to-handle problem for online retail, which is largely tied to credit cards and third-party payment processors. There’s no direct online equal for layaway, but you might consider offering big-ticket goods on a “Deposit” or “pre-sell” system– sell “deposits” for 20% or 50% of the cost prior to a cutoff date, then reserve stock for those orders, and allow them to buy a “Pay-off” item prior to a deadline to complete the purchase. It’s feasible with even the simplest of shopping carts.

Price isn’t the only way to compete. Shipping and fulfillment can get you valuable edges.

Early in the marketing season, you’re dealing with a significant slice of customers who are handliing gift purchases for abroad– whether it’s military families trying to get presents to Afghanistan, immigrants sending home an offering to their families, or just those who have relatives overseas. A competitive offer and early shipping guarantee can get significant traction there. How many people say “I’d buy that, but I know shipping it to the family back in Cornwall or Guadalajara exceeds tjhe value of the gift?” Use your volume and leverage with shipping carriers to make it affordable, and they’ll buy!

Late in the season, desperation can change the economics of a purchase. It’s December 21. You want to buy the family a nice big TV– 40 or 50 inches. Online might be $100 cheaper, but you’re slapping $150 in FedEx overnight costs to get it home in time for Christmas. Here, retailers with a brick-and-mortar affiliate have an edge by being able to say “We’ll slip it onto the shipment and you can pick it up locally at no extra charge.” Not only does it capture the sale, it gets the customer in the store with a chance he’ll buy add-on goods in a last minute panic.

Now is a great time to push the upsell. Every year has the hot item, whether it’s the Cabbage Patch Kid or the Kinect. If you know you’ll sell your entire inventory of some hot item, this is the time you can also demand customers buy other items– usually with astronomical markup– to gain access to the coveted product. It’s no-lose if you do it right– if your bundle wasn’t compelling early in the season, it may be the only way left to buy for panicked shoppers late in the season facing sold-out signs in other stores. If you do it wrong– get too greedy ($200 of accessories on a $250 item) and people will shun you and you will run the risk of not even appealing to the panicked shopper. Remember, you’re not just competing with Toys R Us anymore, you’re competing with the speculator on Craigslist who will be willing to let his kid moan on Christmas day for the ability to turn a $200 profit on his purchase.

Don’t neglect your mainstream base. This advice holds especially true for businesses with major ongoing sales, or lower seasonal concerns. If you go too aggressively for the holiday sale, you may end up impeding– and increasing the bounce rate– for customers who aren’t interested in your holiday promitoons. If you’re an office-supply vendor, I don’t want to work my way through 300 engraved gift items and tins of stale popcorn in order to get to the toner cartridges. Same thing online– don’t bury the normal navigation and search figuring you’ll be targeting primarily gift buyers, unless you have hard numbers– matching the ongoing site performance– which say it’s worth it.

Conversely, now may be the best time for split testing. Statistically valid tests require lots of volume, and the holidays offer it. It’s a good chance to test things like colours, button styles and sizes, and checkout workflows– things which aren’t wildly affected by the change in customer behaviour for gift-buying. But product mixes and layouts– the data is likely to be faulty. Test the wrong thing, and you run the risk of the Homer Simpson investing– “Pumpkin futures have been going up all October, so I bet they’ll peak in January”

Someone actually check a calendar for variable events, people! Channukah can be anywhere between late November and almost the end of December. It’s sort of funny to go into stores when it comes early– still stocking the tie-in products and messaging, but the actual holiday is long over. You’ll be marking that stuff down 75 percent soon enough.

So have a prosperous and healthy Christmas, Channukah, Kwanzaa, and Blood Sacrifice to Lord Ba’al Day.

Choosing how you’ll accept payment early is vital, because each payment processing service has a slightly different interface, and it’s important to pick a cart which can talk to your service. Yes, MOST carts can be extended to handle MOST gateways, but it adds time and complexity.

Second, do you need any special shipping features? Many people don’t think about this until it’s too late. Those slick automatic calculators you see on many large e-commerce sites require a lot of cart support, and a lot of product setup. You have to tell the cart the correct weight and often dimensions of each product, and many shippers require an account setup to retrieve quotes. Other users only need a flat or tiered rate system (“Free shipping over $50″) Either way, knowing your intentions can help choose a good cart. There’s no point setting up detailed weights if you tell us “it’s a flat $10″ on the day before go-live. As a side issue, many of the carts offering sophisticated shipping options also require more configuration and maintenance, on tasks like setting up different shipping or tax zones, or adding offsets (to ensure that you don’t lose money on the cost to ship your packaging materials)

Third, know your marketing model. If you intend to do recurring billing, it immediately disqualifies a substantial set of both carts and payment processors. It’s not something you add on in the last minute. In addition, you may need to decide if you’re selling “Red Widget and Blue Widget” or “Widget: select colour – red or blue”. The latter requires the ability to store, and optionally inventory– by attributes– a feature some carts ignore. If you’re only selling one or two products, it may make sense to find a cart that can be “pared down”– removing distracting questions like “do you want to sign up for a newsletter” or even “add and remove products from an order prior to purchase” to keep the customer on a rigid path to the checkout page.

Why is it important to know ahead of time? If you’re building a cart, a substantial amount of the effort consists of adapting the proposed design to the existing moving parts the cart system provides. Having to tear it all up at 80 percent completion means you’re likely to slip deadlines or lose focus from the meat of the project.

Although the shiny Apple ad may focus on a billion App Store products, the pervasiveness of the web was a key factor in the success of tablets. Much as in the Netbook craze a few years previous– the form factor all but demands easy access to a broad range electronic content. You going to carry around a stack of discs for your paper-thin tablet?

However, just because your content is safely on a website doesn’t mean it’s perfectly suited for the tablet market. There are a few distinct technical and use-case concerns to be worried about.

First, tablets have some rather limited hardware. Many of them feature relatively low resolutions of 1024×768 or less. Even with a high resolution, their small size may encourage use of a small “effective” resolution– bumping up the text DPI to ensure readability. When even the cheapest desktop PC comes with a 1280 pixel or wider, 96 dpi screen, it often becomes difficult to find a layout which satisfies both user types. Adaptive CSS can play a big role here– as most tablet browsers are capable enough to understand media queries.

The second concern on limited hardware comes from poor input devices. You can’t do pixel-accurate work on a touchscreen. And on-screen keyboards range from appaling to merely awful. While this has led to the assumption “tablets are primarily a content consumption device”, it also means even the little bit of content production required in a normal website– enterring billing information, filling out feedback forms, and such. Sometimes you can cheat– geolocate a user rather than soliciting city and state, or punt info collection to a phone call– but sometimes you have to ask “is it worth it to force a user to go through an extra select box mess to get his birthdate when we’re selling him a pizza?”

Second, some UI conventions we’ve become accustomed to on the desktop are simply gone in tablets. Relying heavily on hover or “mouseover” behaviour will fail, as touchscreens are generally not capable of detecting it. They could, in theory, but nobody’s doing it, and even if they did, there’d be a lot of false positives. The multi-touch nature of a tablet screen can clash with the conventional assumptions of “enter an element/exit an element” that assume a single mouse pointer. In addition, some tablet experiences rely on things like styling a selected link prominently to clearly indicate it was pressed– which could clash with your own styling. In many cases, users prefer a “fake native” look, using toolkits like jQuery Touch to produce buttons and controls that resemble those of native applications, rather than a “custom” or “web-styled look”. It’s a classic extension of one of the most basic principles of usability– you want your program- or site- to resemble what the customer already knows.

Third, rich media support is a guessing game. Want to use Flash Video? Fine on a Motorola Xoom or RIM Playbook, not an iPad. On the other hand, the supposedly “universal” HTML5 video can still be bogged down by differences in codec support. Once that’s resolved, you still have further questions: Should the full-screen experience be optimized for a 7″ widescreen (Samsung Galaxy Tab), a 10″ 4:3 screen (HP TouchPad) or a 10″ widescreen (like some convertible Windows tablets)? Do we design around a user on Wi-Fi backed up with a 5-10Mbps residential cable connection and negligible usage limits, or expensive, 1-2Mbps 3G data?

Finally, there’s a lot of new ground in the tablet experience. Customers are still in their infancy when it comes to location-based services. Going whole-hog on them to provide customized content could impress users– if they get it. If they’re surprised with “Special offers around MESA, AZ” it can be an impediment to the desired use pattern, or worse yet, reaches into that “creepy zone” which sends customers running.

The keys to a successful tablet-friendly site are compromise and extensive testing. You can replace mouseover-powered dropdown menus with click-powered flyouts, or better yet, on-page menus. You can stack different media players and fall-through until they work on most of your target devices, but what you can’t do is build an all-singing, all-dancing PC website and then look surprised when it doesn’t fit on the screen and leaves big “plugin goes here” boxes all over the tablet display.

In addition, it must be remembered that the tablet ecosystem is not a monoculture. People often talk of tablets as “appliances” because they’re somewhat consistent in behaviour, without a wide array of customizations and options– but the differences between them makes it difficult to treat them with the same consistency as, say, toaster ovens or irons.

High-visibility outages aren’t new. Sony, in particular, averages one per week. However, only some firms can emerge from them with their dignity– and customer base– intact. Here’s how:

• Tell the truth. From day one. All you need is one tech-savvy customer– or blogger monitoring the system– to call you out and the carefully crafter story goes down the tubes. It’s often humbling for a rich firm to admit “something broke and we’re working on it”, but trying to blame Anonymous, or China, only goes so far.
• Focus on partial solutions. Maybe your hack was vast and you can’t restore everything now. Give the customers what can be restored today and it can help keep rebellion and attrition down. Maybe you don’t need to bring back the online store today, but adding a page where they can check your warranty and products will at least make you look alive and credible. It’s worth an estimate of how long you can leave a customer without service before they can line up a replacement.
• Keep us in the know. Even if it’s just a daily ‘there is no news’ notification, it helps reassure customers that the system is under repair.
• Plan for the worst. Once more, it’s admitting sad truths, but it’s often times better to announce breaches and failures in terms of the worst possible scope. Saying ‘we only lost 2% of users’ today, then amending six times to 3, 5, 7, 10, 12, and 50 gets you the same net damage, but seven hits in the media, and the distrust from lying the first time.

Nobody wants to fail, but if you treat customers with the integrity they deserve, you can at least avoid looking sleazy or incompetent as you patch things together.

However, designing a site to be too much in service of the brick-and-mortar customer experience can be a web nightmare. Here are some issues you might want to avoid.

• Do not assume customers want to be steered into a brick-and-mortar store. Some retailers we’ve spoke with are reluctant– or outright forbidden due to vendor policies — to provide prices online, or even price quotes via email. I guess, if it’s a phone conversation, there’s no evidence you’re undercutting their minimum advertised price. However, this results in a strange “pretend” website full of goods you aren’t allowed to actually buy. Few customers are going to get all excited about a product, and then go offline to complete the research process. If you can’t explicitly say prices, words like “We will match any other authorized dealer” can at least earn you the trust that you’re not going to screw the customer around. As an alternative, perhaps quote a price for a package– which includes some non-MAP-governed items– so you can at least give customers a ballpark. The $2,000 audience doesn’t want $20,000 products, and vice versa.
• Do not stuff the site with brick-and-mortar detail that will become a maintenance hassle. For example, if you have ten locations, it is fair to offer a phone number for each, and perhaps even a location finder. But if you start including hours of operation, don’t be surprised when you’re spending a significant amount of time tending to local closures and special holiday hours. Yeah, you can probably build a special-purpose app to streamline it, but it may be more efficient– if you can’t enforce a standard like “all locations open 9-5″ — to just say “call for hours”, as phone numbers change much less frequently.
• Understand the audience online is not the audience offline. With old media, you bought a region pretty specifically. Nobody in Manhattan buys the Arizona Republic, except when they need to wrap fish. The Yellow Pages stayed comfortably within your service area. Meanwhile, us whiz-bang techno-kids are getting access to retailers all over the world! While you may TARGET Arizona, you can’t (with any degree of technical feasibility) RESTRICT your site to Arizona only. Be prepared for at least some segment of your traffic to have odd questions like ‘Can I get it shipped?’ Sometimes, you may discover there’s actually significant untapped business outside of your local territory, and by expanding or preparing a joint-venture with other firms in the sector, grow your business in new directions.

  You also have to consider if your messages make sense online. You may have mastered a sales process which works well as long as a customer is trapped in your office. When he can go away, compare products and prices, and come back, that sales practice may be obnoxious or simply fatally flawed. Rely on a more informed customer who you can’t snow-job. As a matter of fact, it may also be worth thinking about for your brick-and-mortar sales. Modern technology means you can’t control the message even inside your own office– or haven’t you seen customers grab their iPhone and start comparison-shopping right at your display?

For those businesses still trying to prepare a first web presence, it makes sense to start from the “Web” perspective and then move backwards into how your business can use the tools it offers, not to hope your existing presentation and business model fits online.