In the last 3 years while working with Saflink, Verdiem, and Invisible Software Inc, I’ve been through the legalities, and process of acquiring several US working visas … L1-B, H1-B, and 3 TN’s. Oh, and I was also working with Microsoft on getting TN status to work with them.
Here’s the top 5 things I’ve learned:

1. Although big, scary, and intimidating, Imigration officers are your friends.
Yup, those guys sure know how to make a person feel guilty …. Even if there’s nothing for you to feel guilty about. Each time I get through the application interview, I feel a bit dirty. I feel like I’ve done something wrong … even though I haven’t. But …. I’ve learned that these guys actually are your friends. While it seems like it, there, not actually out to get you, or to stump you on your work history, or job role. They’re simply looking to do their job, and gather the information they need to stamp your working visa.

2. These guys have heard about google.
It really floored me the first time I applied for a visa with Invisible Software the information they had on the company and myself. They knew who worked for the company, where some of the people had worked before, when I’d worked with some of the people currently with the company, information of the product. While I knew that they had access to immigration information, I’m not sure why I figured they didn’t have access to google, and the wealth of information available for anyone on the internet.

3. Make your application package complete and professional looking.
While working at Saflink, we had several lawyers draft up the documentation needed for application. The lawyers coached me on how to conduct myself during the interview. Immigration officers spend their days reviewing and conducting these interviews. Make it easy on them by having all of your documentation ready, ordered, and professional looking. When applying with Invisible Software, I had the needed documents, but they didn’t have the look of something placed together by lawyers. It makes a difference

4. They mainly just want to know that you’re not sneaking into the country.
This may seem stupid to say, but it took me a while to realize this. Meeting the requirements of a NAFTA position and proving that your company has the ability to pay you, isn’t their way to best have fun with a stressed out traveler. It’s not a game of *how can we stump them* that they like playing. At the root of these questions is “Is this guy trying to game the system and create a porous border for himself?” Did this guy just doctor up documents for himself, withdraw $50 and show up at the border?

5. Just tell the truth
This of course seems obvious, but when under the critical eye of the scary Immigration officer it might seem tempting to stretch truths to make the process easier for yourself. Invisible Software is a small software company. It’s received funding (but not like Verdiem ala Kleiner Perkins) and is financially stable (but not like Microsoft), but not at the same level as Microsoft. While it’s tempting to claim billions in funding, and Microsoft revenues, there’s nothing wrong with just saying “Invisible Software received funding that will provide runway for at least a year, and the goal is that revenue will extend the runway. Currently there are only non-paying beta users, but there will be a paid version available in the future.”