I’m often asked by people if a startup really can compete with a behemoth software company like Microsoft?  After all, couldn’t Microsoft just turn their attention on any startup and squash it like a bug?

In theory, possibly… but in reality, not likely!  Big companies are usually so full of bureaucracy they can’t even do small things right (or fast).

For example, I recently spent several hours wrestling with Microsoft’s Xbox LIVE billing system simply trying to purchase an Xbox LIVE Gold Account.

Hey Microsoft, want to know how to double Xbox LIVE Gold Account sales overnight? Stop making it so hard to accept our money!

Seriously, I’m sure there is a product manager somewhere inside Microsoft’s bureaucracy looking at the Xbox LIVE sales numbers and pondering what new marketing plan could move the needle on her product sales and achieve her quarterly MBO objective but that product manger is obviously not using her own product!

When I work with entrepreneurs who are looking for ways to increase their product sales I’m always surprised how few of them have taken an objective look at how their own product is purchased.  Simply watching someone try to buy your product can be tremendously enlightening.

We make assumptions every day that customers are just like us when in reality they are very seldom anything like us.

In this example, Microsoft completely blows the customer experience (way beyond usability).  No startup should ever make these mistakes:

1)   If you offer a payment option button make sure the payment option connects you to a website page that exists (really?)

2)   Once you fix this problem make sure that you can actually process the credit card when someone fills out newly created page (amazing)

3)   If you offer online chat support provide connections to people who are paid to help you and do not connect with other frustrated users (your killing me!)

4)   I liked the option to fill out a form to have a tech support agent call you back when they are free but why not enable the button so you can submit it?  (OMG!)

5)   Always good to give someone who calls the phone support directly the same “we’ll call you back” option via your automated phone system but when you do call them back don’t dump them back into the wait queue again!  (this has now become personal)

6)   When your tech support agent does finally answer the phone please don’t insist that the customer registers more secret answers to secret questions before helping them… and if you do please do not act confused when matching the secret answers to the secret questions (secretly hoping a meteor will kill me now)

7)   When your customer politely asks how your tech support agent can easily register the same credit card and the customer, despite hours of trying, could not don’t simply shrug and say – “yeah, that seems to happen a lot, is there anything else I can do for you today”?

Customer experience is critical for being a successful company and those that don’t understand this are doomed.

Seeing the problems Microsoft is having simply processing payments on their website makes me feel pretty good about doing battle with giants.