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Are Your Tools Fit for Purpose? Try Them On Like Clothes

Assessing whether your enterprise tools still fit is like trying on clothes. First: do they still fit? Then: are they actually useful? Nostalgia is not a procurement criterion.

By Shailin Dhar

Every enterprise tool (the ERP, the SaaS stack, the supplier you have used for a decade) should be tried on like clothing. There are two questions, in order. First: does it still fit? Second: does it have real utility? You have to answer them in that sequence, because a garment that no longer fits has no utility to argue about.

Here is the part nobody says out loud. When a person is in shape, ill-fitting clothing is simply "not a fit." The jacket is wrong; you set it aside without a second thought. But when a person is out of shape, the same ill fit gets blamed on the body instead of the garment. The mirror becomes an accusation. And so the jacket stays in the closet, defended, because getting rid of it would mean admitting something about yourself.

That exact shame lives quietly inside ERP and supplier selection. A tool no longer fits the company it is dressing, but nobody wants to say so, because the tool was chosen by someone still in the building, or by the person now defending it. So the misfit gets rationalized. We restructure the process around the software. We blame the team for not "using it right." The garment is fine, we insist; the body is the problem.

  • Fit is objective: does the tool match the shape of the business as it exists today, not as it was when you bought it?
  • Utility is secondary: only worth evaluating once the thing actually fits.
  • Nostalgia and sentiment are not corporate decision criteria. "We have always used it" is a feeling, not a fact.
  • Shame corrupts procurement: when the misfit gets blamed on the org instead of the tool, you buy the wrong thing to protect the last wrong thing.

The fix is unglamorous. Take the tool off the pedestal and hold it up against the body you have now. If it does not fit, that is not a verdict on your team. It is a verdict on the garment. Say it plainly, and you can buy something that actually fits. Keep flinching from the mirror, and you will keep dressing a growing company in the clothes of a smaller one.

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