I had a conversation with a friend the other day that reminded me of some advice that I have given for a long time. My friend is developing a new kind of software and his coders and programmers are constantly telling him that they can’t solve a particular coding issue. He drives them crazy because any time they tell him they can’t do something, he expects them to be able to tell him why it won’t work. They generally can’t immediately answer this question and so they have to go back and figure out why it can’t be done.

I laughed when he told me this, because it’s something I have been telling company owners to do for years and I might even have been the one to tell him to do this many years ago. When somebody tells you that something can’t be done, you need to make them tell you why. Over the years I have found asking that simple question to be one of the more powerful management tools you can use.

So what is the value in knowing why something doesn’t work? I’ve always found a number of reasons for using this tool:

• It helps to turn your staff into critical thinkers, because if they know that they are always going to have to explain why something you want won’t work, then they will learn to ask themselves that question before they come and tell you no.
• And that is important because often, when examining the issue closer, they will find out that perhaps the answer really isn’t no and that there might be another solution they haven’t tried. So making somebody prove that something won’t work often leads to a path to make it work after all.
• But even if it turns out that the answer is no, then looking closely at why a given solution to a problem wouldn’t work will often let you find another solution, or even a partial solution to your problem. I find that thinking a problem the whole way through is a useful exercise even when it doesn’t produce a solution.
• This makes better employees, because it forces them to better understand whatever they are working on.

Let me give a simple example of how this might work. Let’s say you ask one of your technicians to set up some kind of special routing for a customer and they come back and tell you that it can’t be done. That first response, that it won’t work, doesn’t give you any usable feedback. If you take it at face value then you are going to have to tell your customer they can’t have what they are asking for. But when you send that technician back to find out why it won’t work, there are a wide range of possible answers that might come back. It may turn out upon pressing them that the technician just doesn’t know how to make it work – which means that they need to seek help from another resource. They might tell you that the technical manual for the router you are using says it won’t work, which is not an acceptable answer unless technical support at the router company can tell you why. They may tell you that you don’t own all of the software or hardware tools needed to make it work – and now you can decide if obtaining those tools makes sense for the application you have in mind. You get the point: understanding why something doesn’t work often will lead you to one or more solutions.

My whole consulting practice revolves around finding ways to make things work. My firm gets questions every day about things clients can’t figure out on their own. We never automatically say that something can’t be done, and for the vast majority of the hard questions we are asked we find a solution. The solution we find may not always be what they want to hear, because the solution might be too expensive or for some other reason won’t fit their needs, but they usually happy to learn all of the facts.

Give this a try. It’s really easy to ask why something won’t work. But the first few times you do this you are going to get a lot of blank stares from your staff if they have not been asked this question many times before. But if this becomes one of the tools in your management toolbox, then I predict you are going to find out that a lot of the unsolvable problems your staff has identified are solvable after all. That’s what I’ve always found. Just don’t do this so well that nobody ever calls us with the hard questions!