How will we know if we made a mistake?

We are interviewing for a project next week. If we are successful, this project will be a feather in our cap, a project we can do really well, and an opportunity to define the future of the organization that will hire us. It is this third item I wish to think about here.
This organization has been around for a while, executing its mission in a kind of casual manner. It’s buildings, up until recently, were three-season buildings, meaning they were not usable in our Maine climate during the winter. People went there during the summer, their families in tow and essentially on vacation while the breadwinner did his (almost always a he) thing. New construction a few years back created space for year-round endeavors. These new buildings looked, as much as it was possible, like its three-season predecessors. As the organization becomes more focused, more sophisticated, and more successful at its year-round mission, the question arises: should its physical plant continue to evoke a past, or press on to a new and more meaningful future?
My argument is the organization should embrace change. It should not build super-modern buildings for the sake of looking super-modern, but it should not be afraid if it is best served by buildings that appear to signal a break with its past.
If in 100 years, someone looks back at the history of this organization and notes the buildings that mark milestones in the organization’s evolution, will they look at this current building project as a significant inflection point?
The question for those who design buildings is this: By urging clients to embrace a new aesthetic, are we running the risk of making a mistake? I think the answer is yes, if all we are doing is arguing for a different style to mark an inflection point. If, however, we are asking a client to be open to a new style because that style is better able to answer new needs, then we have not made a mistake. We have opened some eyes, and history will judge us to have made the right choice.

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Principal at Sealander Architects, Ellsworth Maine. Revit guru. Married with 3 children. Avid gardener. Lived in San Francisco for nine years. Master in Architecture from Columbia University Bachelor of arts in religious studies, Wesleyan University. Graduated Staples High School, Westport CT. Hope to spend some time in Hokkaido before all is said and done.