Adeptness at delegating is one of the toughest skills for IT managers to develop. Why? Because you learn very quickly in technology that whatever it is, if you do it, it will be done right. During your nonmanagerial life, you learned that allowing others to participate in a project that you’re responsible for is a sure way to have problems.

Then, suddenly, you’re a supervisor, and your whole world changes. Now you’re being held responsible for a much bigger segment of work, and you must use others to get the job done. “Yikes, why did I take this job?” you wonder. “How do I ensure that these people know what to do? How do I verify that they do things right?”

There are books, articles and courses on this subject that can be very useful as you begin to learn how to manage. But for me, there was one important question that I always asked myself: How do I know when I am delegating enough?

I think that the answer is very simple: You are not delegating enough if the questions that you are getting are easy for you to answer.

Yeah, that’s right. As a manager, you have time for only the tough questions. If you are handling the easy ones, then you are wasting time on matters that should be handled at a lower level and the productivity of your group will suffer.

Here’s how to evaluate your delegation propensity. If your subordinate comes to you with an easy question, then there are two possibilities. First, the subordinate doesn’t have the confidence to make the decision and wants validation from you, the boss. In this case, you must be careful not to answer the question but to tell the subordinate that he should trust his own instincts and make the call. In this way, he will have an opportunity to grow as a person and will begin to gain the confidence that he’s lacking. You also will be able to monitor his decision-making ability.

The second possibility is that the answer was indeed simple but you didn’t share the necessary information, requiring the subordinate to ask the question. This may mean you retain some information in order to feel that you have not lost control, but it causes your people to be frustrated and to feel that you don’t trust them. It’s important for you to disclose to your subordinates all of the information that they need to do their jobs.

Well, then, if you tell your subordinates everything, what’s your job? Don’t worry. There is always more to do. The main role of the boss is to work at the intersections. By that I mean that any organization must interact with peer organizations to get the job done. This is where the supervisor can have the most impact; it’s not where subordinates should spend their time. When you hear the phrase “That’s above my pay grade,” this is exactly what it means. This is the boss’s turf, where relationship-building and mutual understanding create successful projects.

So the next time you meet with a subordinate, ask yourself this: Is the question too easy, and if so, should he have known the answer, or is it my fault that he doesn’t? By analyzing each of these encounters and taking the appropriate actions, you will grow your people and improve the productivity of your organization.

Of course, once you have accomplished this, you will have time for only the tough questions. That will make your days harder and your nights more sleepless. That sounds like an accurate description of management to me. Welcome aboard!

Paul M. Ingevaldson retired as CIO at Ace Hardware Corp. in 2004 after 40 years in the IT business. Contact him at

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