I've noticed something about myself that I don't particularly like.

When somebody tells me, "Absolutely. No problem. We do this all the time," I immediately feel better. When somebody says, "I think we can do it, but let me check a few things first," I start having doubts. Which is strange, because the second guy may actually know more than the first.

Suppose I'm talking to two contractors about a renovation. The first one walks through the property, looks around for fifteen minutes, and tells me he can finish everything in six weeks. No hesitation. No complications. No worries. The second guy spends an hour looking at the plumbing, asking about permits, checking the electrical panel, and wondering whether the walls are hiding something unpleasant. He says eight weeks. Maybe ten, depending on what we find.

Guess which contractor I'd rather have a beer with? And guess which one I'd probably hire if I weren't paying attention? Confidence is a wonderful product. People love buying it. And I suspect I've bought my share. But then there's the opposite problem: the strong, silent type. He comes in, looks at the problem, grunts something, does the work, hands me the bill, and leaves. Maybe he's brilliant. Maybe he's the best contractor in Miami. I wouldn't know. He hasn't told me anything.

Now, strong, silent types are wonderful in a mining disaster. When I'm trapped underground and somebody is digging me out, I don't particularly need a lecture about geology. Just get me out. But in most other business situations, I'd occasionally like to hear a "why" and a "because." Why are we replacing this? Because the old one can't be repaired. Why does it cost so much? Because the cheaper solution will fail in two years. Why do you need another week? Because the concrete hasn't cured, and I don't intend to pretend otherwise.

I'm not asking him to expand the universe every time I ask a question. I don't need a forty-five-minute history of plumbing every time somebody fixes a pipe. But I do need to understand what I'm paying for. And here's something peculiar. Even excellent work, if it isn't explained at least a little, can leave me feeling ripped off. The contractor may have done everything perfectly. The price may be fair. The result may last twenty years. But if all I get is a bill and a shrug, I don't know whether I've paid for expertise or simply been charged a lot of money.

That's not necessarily the contractor's fault. Maybe he thinks the finished work should speak for itself.
And in a perfect world, perhaps it would. But I'm not a contractor. That's precisely why I hired one. If I could recognize every clever solution and appreciate every difficulty he avoided, I probably wouldn't need him in the first place. So perhaps explaining the work is part of the work. Or maybe I'm just uncomfortable paying for something I don't fully understand. Not selling me something I don't need. Not talking me into accepting a ridiculous price. Just helping me understand the value of what he actually did.

But there's an opposite danger. Some people are wonderful at explaining things they don't understand. They have an answer for everything. They make complicated problems sound simple. They know exactly which words make me comfortable. And suddenly I'm paying for a performance instead of a solution. It happens with lenders, brokers, contractors, real estate agents, practically everybody. The person who tells me exactly what I want to hear immediately seems more competent than the person who makes me uncomfortable.

Am I buying expertise, or am I buying relief from uncertainty? There's a difference. Of course, confidence isn't automatically ********. Sometimes the guy who says "No problem" really has done it a hundred times. He recognizes the situation, knows the obstacles, and has already solved them for other people. Meanwhile, the fellow who needs three weeks to investigate every little detail may simply be inexperienced, indecisive, or afraid of taking responsibility.

I don't want to confuse caution with competence either. There's a reason we pay experienced people good money. Part of what we're buying is their ability to make decisions without rediscovering the entire universe every Monday morning. So maybe the question isn't whether somebody sounds confident. It's what his confidence is based on, and whether he can explain it. Has he done this kind of job before? Can he tell me what might go wrong? Can he explain why he's recommending one solution instead of another? Does he know the difference between something he knows and something he's assuming?

And here's a test I particularly like: what happens when I ask him a question he can't answer? Does he say, "Good question. Let me find out"? Or does he immediately invent an answer because admitting uncertainty would ruin the performance? I think the ability to say "I don't know" is one of the most underrated professional skills. Of course, saying "I don't know" twenty times during a ten-minute conversation isn't particularly reassuring either.

That's the problem. I need somebody who knows enough to be confident, is honest enough to know where that confidence ends, and is willing to explain just enough that I can follow him. And I have to remember something else. I'm not immune to this myself. I've been in business long enough to know how tempting it is to reassure a customer before I've examined every detail. Nobody enjoys being the person who slows down a deal. Sometimes "We can make this work" is a conclusion. Sometimes it's a sales pitch. And sometimes it's just hope wearing a nice suit.

So when somebody tells me, "Absolutely. No problem," maybe I should stop feeling relieved for a moment and ask: "What makes you so sure?" And when somebody tells me, "Let me check," maybe I shouldn't immediately start looking for another guy. But I don't think I should have to choose between the smooth talker and the silent genius, either. I want somebody who can do the job - and tell me why he did it that way.

I don't want to pay somebody just to make me feel confident. But apparently, I don't like paying somebody who doesn't make me feel confident, either.

Now there's a problem.