When you’ve got someone by the balls, squeeze.
Now think about your users and your web application. Are you squeezing ’em?
Web applications typically do a very poor job of motivating users immediately after they sign up. Sign up for any web application you want and they generally drop you into a dashboard or timeline-like display with absolutely no clue what you’re supposed to do next. So you click around aimlessly, check a few things out, lose interest and leave. Now try getting that person back!
If you’re building a web application you need to show people what they’re supposed to do. Squeeze.
Once you’ve got someone into your web application and they start using it, they’re demonstrating a level of commitment. And considering most people only use a handful of applications a day, if they use your web application with any frequency (even early on) that commitment is pretty serious. So squeeze! Go for the ask and encourage (force?) your users to help you in some way. If your web application requires users to share things with others in order to increase usage and adoption then you have to ask them to share. More than that, you have to build the sharing functionality directly into the daily flow of your application’s use. Putting a “like” button somewhere doesn’t count. Get obsessed with viral loops and how you’re going to drive activity in your web application directly through its core feature set; directly through its core DNA. Laurent Kretz has a good article summarizing many of the tactics you can use in a social app for it to work. It shows you the extent to which you have to think about these things, test them and most importantly embed them directly into the daily flow of use for your application.
Just look how much effort retail stores go into when designing a location. And just think about all those little goodies they’re selling right at the cash register. Retail stores spend a lot of time on location design to maximize how much money they take from your wallet to put in theirs. Why should web applications be any different?
It’s better to beg for forgiveness than ask for permission. Mark Suster shares a great story about his own experience with that mantra. And I believe the same holds true with your users. Sure you don’t want to piss them off. And having them publicly complain about you is scary. And there are lines not worth crossing. But if you don’t take advantage of your users to your benefit and ultimately theirs (I’m not saying you should take advantage and not deliver the goods!) then you’re losing out.