Suppose that you met someone at a trade show who months later emails you about a business opportunity. You remember little about the person. After five minutes of digging, you find that you friended the contact on Facebook a few months ago and followed them on Twitter. You’ve since tuned them out, but, man, that business proposal looks hot. You want to respond without revealing how little you remember, and without spending a lot of time reminding yourself. You also want to know enough about the person to decide if they’re worth a reply. If only there were some way to put this information somewhere on your Gmail page so you don’t even have to open a new tab to find it.

A new web app wants to be that tool. It almost succeeds. Rapportive is a Gmail-specific, free add-on for Chrome, Firefox, Safari, and Mailplane that gives you information about your email contacts in the sidebar where you’d usually find ads.

Here’s what my Gmail looks like after installing Rapportive and opening a recent conversation with fellow Reputation Management contributor Rebecca Kelley:

Rapportive screenshot

Rapportive screenshot

In the right sidebar, there’s a profile for Rebecca. If her avatar image is actually a picture of her face, I can recall what she looks like, and I see where she’s from. At some point, I also recorded her current position, right into her Rapportive profile. I see I’m following her on Twitter, and a Facebook friendship request is pending. If I had a LinkedIn account (which I don’t), I’d see even more information about her.

Installing Rapportive is uber easy. First, you go to their website. Second, you click on the giant orange-creamsicle-colored button that says “Add Rapportive to Gmail.” Third, depending on what browser you’re using, you’re brought to another page with further instructions. For Chrome, all you do is (fourth) click the orange-creamsicle-colored text link that says Chrome Extensions Gallery. Finally, after confirming that you’re on Rapportive’s Chrome Extension’s Gallery page, click the giant button that says “Add to Chrome.” You’re good to go.

With the basics out of the way, I’ll review some of Rapportive’s features that are relevant to reputation management. The key point is that Rapportive can influence your reputation in two ways. First, Rapportive purports that you can use it to make your email more personal. Second, other people use Rapportive, and they might see (and collect) information about you that they’ll see every time one of you emails the other.

Using Rapportive to Improve Your Reputation?

A number of Rapportive’s features are useful for managing your reputation via email. Rapportive sells itself as a method to make your emails more personal. If I hover over the Twitter link in Rebecca’s Rapportive profile, I see some of her most recent tweets. Perhaps I can induce something about her mood, or reference in my email something funny or thought-provoking that she just tweeted.  This isn’t so easy with Facebook. It would be cool if I could see whether or not Rebecca and I have mutual “likes,” or if I could see some of her recent posts. But I don’t. I have to click on the Facebook icon, which just takes me to Rebecca’s Facebook page. Well, why don’t I just Facebook message her then? The other problem is that, if you aren’t linked with that person on a social network already, you don’t see much about them that they don’t share publicly. So why don’t I just Google that person?

A more useful feature for Rapportive than its social network links is the ability to write notes about your email contacts, which Rapportive saves into a virtual rolodex. For example, I could write down on Rebecca’s profile that she participates in Ironman and other -athlon and -athon sorts of endurance competitions. Cool, I’ll remember to ask her if she’s been training or raced lately the next time I email her. This gives her the impression that I remember details about people that  I’ve met only a few times, so I must have a mind like a steel trap. It also flatters her that I remembered something about her in particular. But be careful. You can quickly cross the line from making your email more personal to just sounding creepy. One problem is that the notes feature of Rapportive is tucked down at the bottom of the profile, beneath all that semi-functional social network junk. I have to scroll down within Gmail nearly all the way to find it. Again, why didn’t I just Ctrl+T a new tab, then Google and Facebook search Rebecca?

Another issue that Rapportive thinks they’ve fixed but haven’t is that it is most useful when you are looking at an existing email conversation. If, like me, you use Google’s new Facebook-message-inspired email composition interface (because it makes way more sense given the way most people use email nowadays, and you can have more than one composition page open at a time), you don’t see any information about a person in the composition box. So all those notes you took time to write on someone’s Rapportive profile? Yeah, you can’t see them unless you want to go back to the constraint of having one email composition page open at a time. Lame.

Using Rapportive Because Other People Use It?

Despite its limitations, Rapportive was acquired by LinkedIn. Congrats to the Rapportive team. What this means for you is that some of your email contacts and leads might use Rapportive. Thankfully, you can optimize your Rapportive profile to make it look pretty. You can make sure your avatar isn’t embarrassing. You can add current occupations. You can make sure that you aren’t tweeting too many obscenities (unless that’s okay in your field) because, remember, an email contact could be reviewing your tweets as they read an email from you. You can only take control of and edit your Rapportive profile if you are a Rapportive user. So my advice is to get Rapportive for this reason, and only this reason.