The Square Peg
September 10, 2026
Sometimes in B2B technology selling, both sides, the client and the solution provider, can be doing their best and still feel frustrated.
You think you are selling a proven solution. The customer thinks they are buying something tailored exactly to the way they operate.
At first, the gap looks small. A few changes. Then a few more. Every review uncovers another requirement. Months later, you realise that what they need is so different from what you actually built that both sides are now trying to force a fit.
It is the classic square peg and round hole problem.
The mistake is to assume that because the customer has the same broad problem, they must be the right customer for your solution.
Sometimes the product is good, and the customer need is also perfectly valid.
But they simply do not fit each other.
And continuing to force the fit does not create value. It creates frustration.
One of the harder lessons in enterprise selling is knowing when persistence creates value and when it only prolongs a poor fit.




