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 INSECURE BOSS

Maturity is an ideal quality in any manager. Among the most obvious signs of maturity is self-confidence, a trait I like to call “comfortable in their own skin”.  But what if your boss seems uncomfortable in their skin, insecure and uncertain about their performance as a manager? What if you always feel you are walking on egg shells when dealing with them?  The following few suggestions may help you navigate such a relationship,

First, abandon any hope of fixing this boss.  Although many secretly believe they can fix almost anything, other people must fix themselves.  Whatever lies behind someone else’s lack of confidence or insecurity is beyond our understanding, so don’t go there.  Better to work on a coping strategy with such a boss.

Second, avoid behavior likely to foster your boss’s feelings of uncertainty and insecurity: being overly confrontational; openly challenging them in public; bragging to them about your own accomplishments; or being unnecessarily critical of what you believe are their shortcomings.  Some honest disagreements with a boss are inevitable but avoid excess.

Third, Look for opportunities to affirm your boss’s accomplishments, sound decisions, good advice, and positive behavior. Positive reinforcement, provided in a timely manner, is a powerful motivator and confidence builder..

Fourth, look for ideas and initiatives that you and your boss can both share. Having a sense of shared commitment to something, makes a bright idea seem less threatening to an insecure manager..

Finally, and perhaps most important of all, do not engage in frequent discussions with your colleagues in which you share your negative thoughts, criticisms and frustrations with your boss.  Such negative chatter has a maddeningly predictable tendency to somehow circle back to the last person you would wish to share it with.  Such circled-back comments hardly bolster a boss’s self-confidence. They are counterproductive to your objective of an effective working relationship and could easily poison permanently your relationship.

UPDATED April 2026

Categories: Managing & Leading, Managing Poor Management

Tags: advice for managers, advice for managers from managers, behavior change, best managers, effective management and leadership, effective managers and leaders, line management, management advice, Managing & Leading, Self-Management