“Jazz It Up”
“It’s Not There Yet.”
“I Don’t Like It.”
“Can I See Some More?”

It’s not easy for a writer to hear these. But it’s not that I have a problem with making changes. In my career I’ve probably made more than 25,000 changes. It’s that this kind of feedback is so vague that by itself, it does nothing to help ensure a better product for the next round.

Therefore, what we need to do is probe deeper with questions that draw greater specificity out of clients, even if it has to get slightly uncomfortable or difficult. If you’re an AE or Creative Director, you owe this to your team. There have a been a few times where said AE/CD flippantly replied “figure it out,” to my request for greater detail. But perhaps they were too scared to ask the client. After all, how dare we ask the people paying us for more information so that we can do our jobs well for them.

We can complain about this status quo or we can take the reins with questions like:

“Can you tell me more about that?”

“Which part in particular are you not liking as much?”

“I have no problem doing more, but I want to make sure we’re efficient with our time. In order to do that, what types of words and images would excite you?”

“Pretend someone is giving a testimonial about your brand. What are they saying?”

“Knowing we can’t do the exact same thing, what types of brands do you imagine when you consider what you’d like this brand to look and sound like?”

You may not get the answer you’re looking for in the first sentence. That’s not the point. The point is to get them talking and talking and talking. Because somewhere in there, as their voice inflection changes, their eyes get wider and their body language becomes more animated, lies the passion of what that client really wants to achieve. I’m not saying to literally repeat what they say. I’m saying to pay careful attention to what they seem to value most in the language and design direction.

I once had a Creative Director who said, “It’s not there yet,” as her feedback on most things. I kid you not. But after bashing my head against the wall, I decided that blaming her for the inability to articulate her feedback wasn’t going to get me anywhere.

Instead, I had to be like a “60 Minutes” journalist – Mike Wallace was the very best at this – interviewing a tough subject who didn’t want to give up the goods.

Study these people and I mean the really, really good ones.

They’re not satisfied with one word answers. They probe deeper to get a good story. In your case, it’s even more justifiable to probe because you’re not trying to catch someone in a lie. You’re trying to get the juicy details that will benefit the client, even if they don’t know how to explain that benefit themselves.

Posing deeper questions like this without making them too uncomfortable is really an art form – whether it’s a Creative Director, Account Exec., client or prospect. But the insights are in there and worth the trouble of extracting. Don’t give up. You’ve got the best of intentions and it’s worth pressing for the good stuff to help people shine – and by the way, you’re one of those people too.

Here are a few examples of the Master Questioner in action (Think you’ve got it rough with your subject? Check out Wallace’s toughest interviews):