Day Two: Freelance Frustration

18 11 2008

Clarifying questions are clotheslining my projects. It’s not that I refuse to ask clarifying questions or somehow think asking questions is beneath me. I usually feel like I have a good understanding of the project until I’m in the throes of it and realize I don’t get it at all. So I guess what I don’t get is why it takes me so long to figure out why I don’t get it. Does that even make sense?

Perhaps it’s cockiness or slight overconfidence. Maybe I want to believe that I understand the project in its entirety so that I look smart only to frustrate myself later on. I think it has more to do with how I complete projects: I have to “see” the parts to think about them. Until I start working on a project, all I have is a request or an assignment on a piece of paper. It isn’t real yet. By the time it is, though, I always feel like it’s too late to ask those clarifying questions for fear that people will say, “Well, why didn’t you ask that in the beginning?” Still, isn’t it better to ask questions eventually than to not ask them at all?

Intellectually, I know that assuming to understand something is about the worst thing you can do, yet I keep doing it because it’s easy. Coming up with questions and being thoughtful about the intent of the project and the work it entails is hard. So, maybe I should try explaining how I operate to the people work with, something along the lines of ‘Yes, I’m nodding my head in the meeting and no, I don’t have questions right now, but will once I start shifting the pieces around in my mind and on paper’. Then again, the way I operate could happen much too late in the game, especially if the project isn’t urgent. Plus, that’s me expecting them to do things my way. That’s not how this business works.

After googling ‘how to ask clarifying questions’, I stumbled on this article on Stepcase™ Lifehack that actually speaks to the opposite end of my dilemma, management. The part that caught my attention was buried in the eighth paragraph (emphasis mine):

An easy to remember, and very effective strategy in avoiding misplaced clarifying questions is to deal with only one question at a time in a conversation (also smart in keeping to one subject at a time, and getting it actionable before proceeding). You do this, by letting the speaker finish whatever they’re saying before you say anything, and you train yourself to get better at sensing those times when they’ve stopped talking, but they’re actually silently thinking of the next thing they’ll say. Learn to get comfortable with silence; consider it to be thinking time versus your next opportunity to speak.

Could it be my need to fill up the silence in my meetings that keeps me from thinking about and asking clarifying questions? Have I really convinced myself that I understand everything to avoid silence and take away my opportunity to think about the project? That’s deep. No, that’s scary.

What to do, what to do? I can’t think of a time I asked clarifying questions to build a model from. Not off the top of my head, anyway. The most I usually ask is: 1) what’s the deadline, 2) how many words, 3) do you need pictures 4) what’s your budget. Way to be client oriented!

I know. I’ll open it up to you, my few readers out there. Sure, questions differ based on the project, but what are your top five clarifying questions? Bonus question: what’s the most thoughtful clarifying question you’ve asked (you know, the one that elicited a genuine ‘That’s a great question!’-type response from whomever you were working with at the time) and how did you come up with it?

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