Sometimes, you just have to be the bad guy. Businesses often need one person who is challenging the norms of the group, and forcing creative thinking. A common term for this person is "devil's advocate." But I've never really liked language that makes people who challenge authority seem sinister, or somehow opposed to the company.
A recent article/interview in the McKinsey Quarterly magazine [note: free registration required] sheds new light on this important organizational role. Since McKinsey consults with large companies, the article focuses on the chief financial officer as the owner of a company's decision-making process. Many smaller companies, of course, do not have a CFO as such, but they need an alternative voice just as bad as larger companies do. In fact, I would argue that the company's early stages absolutely require a strong voice to challenge leaders to rethink ideas. Resources and capital are too precious to squander on a poorly debated concept.
If you can hire someone who isn't afraid to challenge conventional wisdom, bring that person on your team. For smaller companies, a more economical solution may be to bring someone onto your team as a part-time or contract management advisor. An independent voice, and eyes that see your company freshly, offer different, possibly valuable viewpoints, without making current managers feel nervous about their own standing. This person also can talk more candidly, on an individual basis, with the owner or other management members to balance company politics, individual points of view, and the overall company vision.
Your company also can develop this type of expertise through internal activities. Encourage your finance professionals to take positions outside finance and accounting. My most valuable experience while at John Deere -- my previous duty station -- came as a project lead on a SAP implementation project. I was forced to venture outside of the finance function and work with professionals across all areas of the company. I have also seen CFOs spend time in marketing, business development, and even engineering. (A former Deere CFO started his career as an engineer, as did General Motors' current CFO.)
My friends at Free Agent Academy always advise us to "seek wise counsel." Recognizing and accepting different viewpoints -- even if they seem to run counter to the prevailing sentiment -- ultimately will lead to better decisions across the company.