Sort of about rigor — also about tough questions

Over at Signal vs. Noise, Jason wonders about something that perplexes me all the time. Why don’t we talk to each other more?

I’m amazed by how often when faced with a difficult-to-interpret situation, rather than asking someone “What did you mean?” or “What would you like?”, we try to guess. I know I do it all the time. I don’t know why, though.

Jason’s speaking specifically about customers who request additional control over permissions for 37 Signals products. Their reason? They want to prevent users from doing certain things. When Jason suggests that they simply ask those users not to engage in those behaviors, the customers are often shocked. “Hey! Why didn’t we think of that?!”

More of then not, he finds out that the technique works. I would guess that in the instances where it doesn’t work, the ensuing conversation might reveal interesting things about how people want to work together:

Person 1: I’d really prefer it if you didn’t upload files into the Basecamp project that we’re working in together. I find they clutter the space and aren’t always necessary.
Person 2: Oh. Well, that’s interesting. I feel like I *need* to upload files because it’s the only way I can do x, y, and z.
Person 1: Oh! Well, I never thought of that! Perhaps we can come up with a better solution that works for both of us!

I know what it’s like to be in conversation and KNOW I should just follow-up with a question that really drives at what’s going on beneath the conversation itself. But, so often, I shy away from these rigorous encounters.

I suspect a lot of us do. Why is that?