They're both right, of course.
At the one extreme, the outsider sees the organization as a sum of component parts. S/he isolates and evaluates the value of those parts against a desired framework.
--The "big data" specialist asks: Given the people, processes and technologies in place right now, how do we synthesize and analyze it so as to arrive at useful insight on demand?
--The marketing specialist looks at these same elements and asks, where is the unified narrative we can call an identity? How can we make it comparable to or distinct from other entities claiming to do the same?
--The human capital specialist studies the place and wonders, how we can make the most of the talent that is there - to make people most productive?
These filters are like different kinds of eyeglasses the outsider wears. None of them are right or wrong. It's just a matter of knowing when you need sunglasses, bifocals or 3-D.
Of course the head of the organization should integrate all the above and more -- budget, facilities, contracting, and so on -- and be able to wear one or multiple hats as needed.
In short, leaders and experts employed by the organization must be able to think like outsiders.
On the other hand.
Inside the organization there is a built-up well of culture that is normally impenetrable to the outside.
Once within the castle's walls, sure you can learn pretty fast what to say and how to say it so as to "pass" as one of the group.
But it is only through an extended period of immersion that you really become an insider.
And the more time you spend in the confines of the culture, the more you socialize with others inside it, the more your mental models are shaped by its axioms and priorities, the deeper you go.
At some point you may only hang out with people from the inside. Which would make you an inbreeder.
Outsiders and inbreeders typically dislike one another, or at least have a healthy disrespect for what the other represents:
--To the inbreeder the outsider lacks character (loyalty) and brains (intellectual depth).
--To the outsider the inbreeder lacks character (judgmental) and brains (provincial).
But the only way an organization can move forward, especially during times of external disruptive change, is for the inbreeders and outsiders to form an alliance.
--The inbreeder admits that they don't know all there is to know in the world and that at least some people "grown" outside the community can be trusted to help them.
--The outsider admits that a certain amount of "inside baseball" is critical to knowing how to actually do any work on the ground.
The outsider is the anthropologist. The inbreeder is the tribe.
As long as the outsider acts in good faith, and the inbreeder provides a supportive environment for the outsider to acclimate, the "marriage" can work very well.
The product is ideally a next-generation version of the original organization. One that has shed its worst failings, adopted new features that promote its mission, and reinforced its protection against destructive outside (and inside) forces.
Every ecosystem has its mutant tulips. The trick is to remember that their perspectives are often key.
*All opinions my own. Photo by Steven Begin via Flickr: http://m.flickr.com/#/photos/stephenbegin/3531418453/