Excellent post. I'm a self-taught geek as well. I got a summer job at a software company when I was 19 and never looked back. (Besides, I could never explain why I was going to school for chemical engineering and existential philosophy in the first place.) Certifications and 16 years of experience later, I still grapple with where I truly fit.

You discuss the problem in terms of DBAs and DBA Management, and it's certainly valid for those domains. But I'm working through it from the Product Management side. I had the opportunity to spend a lot of time working directly with clients so I heard exactly what people needed, saw how they used the applications daily, and could see the gaps and solutions. It's exactly the knowledge you need to make the right product strategy decisions. So then I was given the role to make product strategy decisions and I spent less and less time with the clients directly. I encouraged feedback from Implementers and PMs, but it still felt removed and the answers didn't come quite as easily. I read a lot and research and listen, but I still don't feel like I know as much as I did. Finding a Business Analyst or PM who can hear what the client isn't saying and then articulate it has been the key. But intuitive, perceptive technicians aren't very common, and it takes time to ferret them out. So perhaps you already have the answer - find someone newer in the field who is fresh with the technology but able to grasp the strategic aspects, and become a team. You both learn from each other.

This discussion has brought me to an interesting question. Of the people you consider great at their technology jobs, how many of them have a background in pure technology?

~Jessica