How do we judge the deal and the person without going numb?

You sit across from a partner, a hire, a vendor. The document is in front of you. The person is in front of you. Your team needs you to catch the flaw in the deal and the flaw in the character — and you worry that doing this job long enough will make you hard, suspicious, unable to trust anyone again. This is not a trade you have to make. The people who go cold did not become clear — they became lazy. It is easier to distrust everyone on principle than to look carefully each time. Sharp judgment takes more effort than a closed fist, not less. Working with others will not do this work for you, but it can catch what you miss alone. One of you reads the terms. Another watches the tone. Compare notes before anyone decides. Do this enough times, and clear-eyed becomes the habit — not cold, not naive.