Square pegs are a controversial element in most organizations. Traditional organizations want everyone in the organization to be a “round hole”. They have little tolerance for square pegs. However, the creative organizations are the opposite. They not only tolerate square pegs but appreciate what square pegs can contribute to the organization when managed properly. In a number of cases employees who consider themselves round holes wake up to discover they are in fact square pegs. One of the events that produces this seismic shift is the arrival of a new boss or new manager. Behavior that was welcomed and encouraged by the old boss is suddenly at odds with the new boss. In these situations both parties frequently don’t understand the cause of the problem but certainly understand there is a problem.


Bosses are often described in the extreme, either as a devil or an angel. Most bosses are neither extreme. They are complex human beings. And these human beings have certain traits and ways of approaching the work. Some managers prefer to review things in writing. If the prior manager was someone who was visual the people reporting to her understood that memo’s and white papers were critical to getting things done. JFK was an example of an executive who appreciated reviewing things in writing. When the new manager represents a new style the organization must react and adapt to the new way of working. Using the previous example LBJ was an executive who needed to hear things. He detested reading memo’s and the like.

New managers, or new bosses rarely compare and contrast themselves to their predecessors. The onus for adapting to change falls to the organization. Thus a brilliant memo writer who flourished under the previous manager is likely to suddenly find it difficult to understand why they are no longer considered a valued employee and someone who did not do well with the previous manager is considered the key employee. A round hole is overnight a square peg.

The situation can be avoided by adding one item to your job description: managing your boss. The new boss is not going to change to adapt to you. They received their promotion by following a particular process and regimen. You must adapt to the boss. You must change.

There are two critical yet simple items to have success managing your new boss. First, an awareness that people, including bosses are different. Become cognizant of the differences from the old boss to the new boss. It may be as simple as realizing the flow of information has shifted from written to verbal. It could be that the new boss prefers morning meetings. Seek out the differences.

Second, discipline yourself to change to meet the new paradigm. It might be frustrating that your brilliant writing skills are no longer an edge for you but if that’s the case adapt to it. You might not be a morning person and might have to alter your habits, but do it if it helps the communication with your new boss. The key: you can manage your boss if you are willing to make the effort.

I’m working on a new book called “The Square Pegs” that deals with managing the various square pegs in an organization. The first square peg you should learn to manage is yourself, particularly when situations such as the above occur.