Biggest Failure, Biggest Success

Boss, IT Business
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I was chatting with a friend the other day about the typical regrets, wishes, hopes and so on when it comes to work satisfaction. I kind of approach this from a different angle because I mostly see my value / success / failure not in what I have (because I have a lot) but what I’ve been able to help others accomplish.

So here it goes:

Biggest Failure: Inability to convince enough people early enough to go to the cloud. It’s heart breaking to watch so many people close up shop or be fired because Microsoft (and to a smaller degree Google) took their clients. The number of “Hey, my client talked to Microsoft about Office 365 and…” calls has been larger than I’d like to admit and I wish I could have made a better argument, business scenario, profit scenario that would have lead people down the right path. Even after all these years I don’t quite know what to say because I’m confronted with daily “We just sell Office 365” and also daily “Yeah, Microsoft is putting us out of business” to the extent that there is no way to phrase “You are naïve and it’s just a matter of time” in a way to get people to take things seriously.

Biggest Success: Stopped arguing with idiots. I don’t mean just deleting the Yahoo / SMB / MVP accounts in a single click – I mean stopping the argument with the biggest idiot… myself. Overcoming the ego issue of having the single good answer is probably what has lead to most of the success. Embracing failure and not being afraid to fail has made the successful projects amazing while minimizing the stupid loss leaders. Once I figured out how to sleep at night without worrying whether <insert very large bet here> is going to be a winner or a loser, I no longer had to win arguments with myself over whether we keep things going or whether we move on. Being able to build a business on numbers as opposed to the right strategy has been the biggest change in MO since ‘06/’07.

Biggest Surprise: How fast things are happening.