Christy’s Laws of Information Technology Leadership Law #4- Ask Questions

The theory is that there are no stupid questions. Okay, this is not quite true – but more on this later. First, a story.

I had a client a few years ago who was nervous about an interview I was about to do with a difficult business user in the early stages of a project. He asked for my list of questions for the interview in advance. I gave him my list:

“How does your department contribute to the success of the organization?”

“What works well and what areas/products/projects could be improved?”

“What do you need this [new computer system] to do to help you achieve your mandate?”

“What are the risks that I need to consider as we plan for and implement this [new computer system]?”

My client seemed unimpressed with my list and unsure that we would actually need the 2 hours we had booked for this conversation. Of course (because this is my blog entry, not yours), we had a great meeting, garnered the support of the previously difficult business user, and after the meeting, my client told me that he couldn’t believe that we had such a great meeting when I went in with a simple list of 4 questions.

As you can imagine, I actually asked many more questions than just the 4 listed, but all as part of a dialogue. The four questions keep the focus on key meeting outcomes and serve to get the conversation started.

Whether you are collecting business requirements, learning about a vendor proposal, or managing a staff member, asking open-ended, neutral questions is the key. And there’s nothing wrong with asking really basic questions (“why do you do that?”) that drive the discussion back to the first principles – i.e., what are we trying to accomplish with this project/department/product - that can get lost in the urgency of day-to-day operations.

And as for the no stupid questions theory, rest assured that there are entirely stupid questions – questions that demonstrate that you haven’t been listening, or don’t care about the answer you just got, or trick questions that get asked because somebody has a hidden agenda. But those are for a different blog entry.


The Osborne Group has been helping organizations succeed since 1993. Based in Toronto, Ontario, The Osborne Group provides a wide range of professional interim management, project management, and coaching and consulting services to small and medium enterprises, not-for profit organizations, and the public sector.

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