Learn to question your questions in IT

Recognizing what you don't know is deceptively difficult, but it's often the difference between project success and failure

No matter what you do in IT, one certainty persists: You will have questions. Very few tasks and zero projects come completely packaged and ready to go -- one item or another will always requires further definition. But the key to moving through that process effectively is to question your questions. The ability to construct the right query is an undervalued talent indeed.

I see this all the time. Meetings are held about one project or another, defining a business need, an IT need, or a technical requirement, and the majority of the meeting addresses the plan to achieve the stated goal. However, in many cases nobody gets around to framing the right question leading to an answer that might actually reach the goal.

This might be as simple as “How do we build a tool to allow our support staff to more efficiently help our customers?” or “What’s the best way we can shore up our DR strategy in the short term?” Those are high-level questions that can lead in any number of directions, but at least they’re clearly stated. Closer to the ground, asking the right question can mean the difference between a successful outcome or a waste of time and money.

As an example, we might want to color outside the lines a bit and adapt a piece of software for a task other than its primary purpose. This is a common occurrence. However, we don’t know if it’s possible to do what we need. Thus, we head to Google and start framing searches to find out if anyone else has traveled this road before and how they solved this particular puzzle. Since we have some knowledge of the tools at hand, we start by constructing queries referencing the tools we have in mind and keywords related to our desired goal. Oddly, however, we find little or nothing that ties the two together. No matter how we frame our question, there’s nothing out there.

Now, we are faced with a quandary: Are we trying to do something that’s never been done before, or are we simply asking the wrong question? The latter is true more often then not.

Perhaps if we’d dispensed with our assumption that the tools we are trying to adapt even can be adapted and started with a higher-level question, we might find that in fact there is no reason to adapt our current tools because there happens to be another tool designed explicitly for our needs. We didn’t know it existed because we were looking at the problem with a false sense of familiarity. Sometimes, not knowing about a particular technology can be a benefit -- and frankly, the world would be a better place if more people had a better understanding of what they don’t know.

If you take this perspective to your workplace, you can see these situations developing. It becomes clear that those who come up with the best solutions start with the best questions. It really is as simple as asking “How do I make an omelet?” rather than “I have a backhoe, how do I open eggs easily?” In too many situations you’ll find someone spending days trying to figure out how to adjust the hydraulics, when a better question would have put them on a much more productive path.

This way of thinking is deceptively challenging. We all tend to lean into problems with the weight of our experience and seek the answer in what we know. After all, tangible success with our past approaches is why we value those experiences to begin with -- we go with what we know.

However, we should all have a tool in our arsenal that allows us to toss our perceptions aside and wipe the slate clean at certain times. The views from that angle can be wildly different. While that new perspective in itself might not lead us straight to the correct answer, it can save us from beating our head against the wall with the wrong approach.

If you find yourself stuck in a loop, trying to determine the best approach to a problem, it's time to question your questions. It’s an easy exercise, but a surprisingly difficult habit to forge.