Craigslist is one of the incredible success stories of the web. And they do it by thumbing their nose at conventional wisdom. They don’t care about stunning design, complicated systems or making more money. Craigslist is all about functionality. If you haven’t read Wired‘s August 2009 story on Craigslist it’s worth a look behind the veil at one of the web’s weirder successes.

As great a techno wonder as Craigslist is, I hate using it. Why? It’s nothing wrong with the site, it’s the people. Sadly people are often the downfall to many of technology’s innovations. Every time I post something on Craigslist I get countless e-mails with stupid questions, drawn out conversations that don’t go anywhere and time and time again I’m left hanging.

So here’s a tip to improve your Craigslist experience: Be helpful.

Responding to a Craigslist Ad
If you’re responding to something posted on Craigslist, be helpful:

• Read the listing thoroughly and make sure you’re not asking something that’s answered in the listing.
• If you’re looking at a widely available retail product, don’t ask the poster inane questions about it. They’re not a salesperson. Look it up online. Do your own research.
• Don’t contact the person unless you’re ready to buy. It’s OK to contact the seller and ask a few questions, but Craigslist isn’t for window shoppers.
• When you’re ready to contact the seller and buy, get to the point. So many people ask if the item is still available. Assume it is and skip straight to the terms. Don’t prolong the purchase with needless back and forth.
• Don’t leave a seller hanging. If you’re interested in the item, follow through. Overly polite sellers might give you first dibs and lose sales waiting on you. Other sellers will skip to the next interested buyer and you’ll be out of luck.

Posting a Craigslist Ad
If you’re posting something on Craigslist, be helpful:

• Include a picture of your actual item. It may seem like a pain, especially if you’re selling a widely available retail product, but it gives you credability. Here’s the actual product, I’m not making this up.
• Pack your posting full of details. Anticipate questions and include everything you can think of, whether or not it may be relevant. It should go without saying, but be honest.
• Be very specific about your terms. Cash or trade? Pick up or drop off? If you don’t specify you leave the door open to all sorts of wacky ideas.
• As people ask questions, update your listing with the answers. More than likely other people have the same questions.
• Delete your post when the item sells and contact any remaining inquirers to let them know the item sold. A quick one-sentence e-mail blind-copied to everyone will do. No one wants to be left hanging.

Not all my experiences on Craigslist are that painful. But I’ve had enough awkward and pointless interactions to know better. Simply being helpful would have made all the difference.

It’s also worth repeating the standard web advice: be careful.