I love reading interviews of fellow designers, but let’s be honest: the average blogger is not in danger of winning the Pulitzer prize any time soon.

It’s natural to be nice and respectful towards people you admire, but when you put yourself in the interviewer’s seat I believe you need to know when it’s time to stop pulling your punches.

I mean, does it help you in any way to know that Designer X uses a MacBook Pro for work (who would’ve thought!), walks his dog every day at 9 (so that’s the secret of his success!) and likes to listen to Portishead while designing? (And all that time I’ve been listening to Massive Attack! I’ve got it all wrong!)

So my message to interviewers: you can still ask designers about their setup and daily routine, I won’t mind (I’ll just skip those questions). But in addition, I’d love it if you could also ask questions that dig a little deeper.

Here are a couple suggestions:

• What are some products or designs that you think are overrated or just plain bad?
• On the other hand, what are some designs you feel are underrated?
• If you could redesign any product, what would it be? Why?
• Which companies do you feel truly understand and value design?
• Which other designers are you jealous of? Who do you look up to?
• Do you have personal projects? Ever thought of founding your own startup?
• What are your biggest frustrations with the current state of web design?

You could even *gasp* try to be a little mean. For example:

• What do you consider your biggest profesional failure or regret?
• Why do you think [a project the designer was involved with] failed?

Or even worse, ask about private things, like money:

• How much money do you make per month on average?
• What’s your hourly rate? How much were you charging when you started out?

I’ll leave it up to you to know where to draw the line. I just feel that we’ve erred on the side of being too nice for so long that it might be nice to turn the heat up a little from time to time!

P.S.: Not that anybody asked, but here are my own answers to these questions:

• Bad design: Cameras. I feel like every single digital camera I’ve ever used has a horrible, unintuitive UI. For me that’s a big part of why cameras are getting their lunch eaten by the iPhone.
• Underrated design: I have no idea. Who comes up with these questions?!
• A product to redesign: Skype, just so that for once I could have a chat sessions with my mother that doesn’t end abruptly when she clicks the wrong button by mistake.
• Companies that get design: Obviously Apple. AirBnB is another one. Also Square. Also, it’s easy to forget this, but most non-tech companies have great design and communication (i.e. almost all fashion companies, for example).
• Designers I admire: I love Rally Interactive‘s work. Also everything by Josh Hemsley and F-I.
• Personal projects: I don’t want people to accuse me of adding that question just so I can sneak in a bit of self promotion, so I’m going to skip that one…
• Frustrations with the job: Probably the sheer number of different things you have to master if you really want to be in control of a product. That’s why I’m very interested in initiatives like Node.js which let you at least use the same language for the client and server side.
• Biggest regret: I regret not thinking “hey, I can do this!” earlier in my life. I was passionate about the web from age 16, but it took me almost 10 years to realize I could make it my job.
• Failures: How dare you! None of my projects ever failed!
• Salary: Right now, about $2000 from eBook sales and Folyo. When I was freelancing, a little more.
• Hourly rate: I started out charging $50/hour, and now charge $150 (believe me, seeing how much I sucked when I started, I’m at least three times as good now!).