Almost all of us have had to deal with a boss whose own management style and set of management skills left something to be desired. Managing up — as it is called — is relatively easy when one’s boss has a skill set, style, and personality similar to our own. But how to manage up when our boss has a style, set of habits, or chronic lack of sound judgment that inhibits and complicates our ability to do our jobs?

In this series of articles under the category “MANAGING POOR MANAGERS”, I will share what hard-won experience has taught me about coping with the less than ideal boss. Begin by asking “does it really matter”? Does this act of bad management seriously affect my ability to do my job, or hinder the performance of my organization as a whole? If it does, then you should act to confront the issue as best you can. If it does not really matter in any significant way, then save your powder for the engagements that really do.

THE BOSS WHO CAN’T DECIDE

The boss who can’t decide is a particularly irritating obstacle when you believe you need permission to act in some way.  Responses like “I’ll think about it”, “I’ll get Back to you”, “let’s hold off on this for a while” or “we should study this some more” can often mean nothing will actually ever happen.  So if you find yourself confronted with this sort of boss, here are some simple suggestions on how to proceed.

First, bearing in mind that you are responsible for your decisions, steel your courage and take some sensible chances on your own initiative. This is hard for many risk-averse managers. But if you believe some action must be taken, that your judgment is sound, that the decision is probably within your scope of authority, and that your boss may sit on the idea, then act on your own best judgment.  You may get your knuckles rapped a few times but nobody can criticize you for lack of initiative.

Second, on those occasions when you conclude that the boss’ approval is absolutely necessary, build the strongest possible case for what you wish to do and emphasize how your action may possibly benefit your boss in some way.  This last little point of emphasis works especially well with a boss keen on looking good.

If several of your colleagues also share your desire for the same action, present your case as a group.  There is always additional strength in numbers.

Finally, cast your presentation of the action you wish to take as “this is what I intend to do and when, unless you object”.  In other words, do not directly ask for permission.  Put your boss in the position of having to say NO.  Although this may seem like a small point, it is actually harder for many bosses to say NO — it has such a sense of finality — than to simply wave their approval.

In the end, with certain bosses, none of the above suggestions may work.  But better to give it your best try, rather than simply letting this challenge frustrate you.

UPDATED April 2026

Categories: Managing & Leading, Managing Poor Management

Tags: advice for managers, advice for managers from managers, bad management practices, best managers, decision making, effective management and leadership, effective managers and leaders, executive leadership, exercising authority, line management, management advice, Managing & Leading