Ways to Handle Problem Bosses and Keep Projects on Track

Posted on December 09, 2019
Ways to Handle Problem Bosses and Keep Projects on Track

Just as a project team looks to the project manager (PM) for support and leadership, PMs themselves are relying on senior managers. In the instances when a superior is unhelpful it can put the success of a project at risk.

PMs can be seen as the middle children of the corporate world — most likely to be blamed when things go wrong, yet not credited for successes. But a good PM doesn’t want to make excuses or point fingers when a project falls short. Patience and skill will be needed to navigate tricky situations with problem bosses. Here is a short primer about five types of sabotage-prone superiors and how to contend with each using a “boss hack”.

1. The Intimidator

The Intimidator uses their dominating personality to get their own way and shut out different points of view. He or she overrides and contradicts a PM in meetings and doesn’t listen to other opinions.

Boss Hack: Before a meeting, the PM has a pre-emptive discussion to go over points of contention with the Intimidator Boss, so it isn’t done in front of the team. The PM explains the need for getting a variety of viewpoints.

2. The Dreamer

The Dreamer has overly ambitious plans yet is ignorant of a team’s limited resources and tight scheduling. They are well intentioned yet make unrealistic and unexpected demands throughout the project.

Boss Hack: When the requirements of a project change, a PM will need to explain to their boss that more resources and/or time will be needed, which may not be possible. This is known as Change Management, a concept the Dreamer Boss may need to be familiarized with.

3. The Buttinsky

The Buttinsky Boss has serious trust issues. They want constant updates and try to involve themselves in detail large and small, having a demoralizing effect on the team.

Boss Hack: Schedule regular weekly meetings for the Buttinsky Boss to get updates at a designated time. Clarify roles and responsibilities and go over the risk analysis that was part of the planning stage of the project — it’s possible they weren’t involved enough.

4. The Oscillator

The Oscillator is a boss who is in over his or her head. They can be friendly and positive, but change their minds on a whim. They avoid clarifying things out of fear of being wrong and are content to let a team waste time and money taking stabs in the dark, and blame others when things go wrong.

Boss Hack: Set up a meeting to get project goals, scope and other specifications in writing. Presenting examples of possible project processes and outcomes and asking for a reaction from the Oscillator Boss can help. A Project Charter can also consolidate the project requirements on a good footing.

5. The Ghost

The Ghost Boss is out of the picture, leaving the team with a lack of support and direction. A neglected team can grow resentful, especially if the boss’ absence means more work for others or scheduling delays due to incomplete information or a required signature.

Boss Hack: Making friends with the Ghost Boss’ admin assistant can garner useful information about how to get their attention. A PM needs to ask for contingency support and a plan for handling big issues when the boss is away. An empathetic approach is best as there may be legitimate personal or professional reasons for the absences.


The topic of this article is inspired by the curriculum for the Schulich ExecEd program The Project Management Program (March 16-18, 2020). Study practical and effective techniques for the successful execution of any project.