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Project Manager Challenge: Dealing with Difficult Conversations - LiquidPlanner

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Project Manager Challenge: Dealing with Difficult Conversations

Difficult Conversation

Rewarding a team member for a job well done or promoting an outstanding employee is easy.  Counseling a poor performing employee, addressing a sensitive issue with a peer or trying to find a solution amongst two conflicting project team members is not.  The reality is no matter how uncomfortable these conversations can be, we all can relate to being found in them.  The outcome of the difficult conversation all depends on how you handle the discussion.

Instead of providing you with a generalized set of cliché guidelines for handling difficult conversations, we wanted to find some real-world situations and share the way project managers in the field handled their difficult conversations.  Of course we changed the names and paraphrased a bit but as you read these examples, think about how you’d react and respond.

Situation #1: Poor Personal Skills

Joe was a knowledgeable employee who had strong technical skills who was often asked to be a guest speaker at technical conferences.  Despite his technical strengths and contributions, he thought his compensation was low. Joe apparently knew his pay was lower than average because he talked to his peers.  Joe came into my office to address the issue.  I gave him an honest evaluation of overall performance, not just his technical ability.

Joe’s major issue was his terrible interpersonal skills.  Technically he was one of the stronger individuals on the team but his personal interactions actually hurt his performance.  Being technically astute, Joe often liked to demonstrate his technical expertise by criticizing other people’s ideas publicly.  He thought he was helping by finding the optimal solution but those actions ended up alienating him from the team.  Joe didn’t take the feedback well, got quite emotional and left work for the day.  He eventually transferred to another department.  Three years later, I ran into Joe and he actually thanked me for having the courage to tell him the truth.

Joe needed a fresh start in a new project team to build new relationships and try a more subtle approach to finding the right technical solution.  He realized trying to outshine his co-workers with his expertise wasn’t helping his career or his reputation. He found that by asking probing questions rather than putting down other people’s ideas, he was still recognized as a technical expert that people wanted to engage rather than avoid.

Key Lesson Learned: Tell the person the truth even if it may hurt their feelings in the short term

Situation #2:  Peer-to-Peer Combat

I had two employees who always differed in opinion and often verbally argued in front of the team.  Both employees were seeking the best solution which they vocally defended, but the constant fighting was disrupting the team.  I brought both of the employees into the office and asked “Which one of you should I fire first?” Both employees had important jobs but neither of them looked beyond their own objectives to see the big picture.  Ironically, they both started defending each other, indicating that losing either of them would hurt the team.  I also agreed, and the two decided to prepare their own points of view and bring them to me for discussion.  I also had them include thoughts from the opposing point of view so they could see beyond their own ideas.

Key Lesson Learned:  Help team members see the big picture and look beyond their own point of view.

Situation #3: About Last Night

Several team members got together after work and one employee had too much to drink and insulted a female employee with an inappropriate remark.  One of the other employees contacted HR about the inappropriate behavior.  HR wanted to fire the employee and I had a couple of days to resolve the situation.  I discussed the situation and the employee admitted fault and indicated that he had apologized to the employee.  I spoke with the employee who reported the issue to HR and asked why he reported it if it wasn’t his business.  I also spoke with the insulted employee and she was ok after the sincere apology.

HR still wanted to punish the employee with a two week suspension with no pay.  I didn’t agree with HR – what happens off the clock between adults is their business.  HR continued to argue but fortunately, I had the final word.

Key Lesson Learned:  Listen to all sides of the story, take personal situations into considerations and support your people.

Common Themes and Approaches

In all these examples, the managers faced difficult situations that required objectivity, honesty and respect for their team members.  By showing respect for the other person, focusing on the desired outcome with emotion and avoiding the “Us versus Them” mentality, the managers were able to a have a difficult conversation.  There is no guarantee that the other person in the conversation won’t try to press your buttons or try to threaten, cry, shout or make accusations, but by avoiding assumptions and applying these key lessons learned, you can successfully have difficult but meaningful conversations.

In preparing for a difficult conversation, it is helpful to ask yourself the following questions:

  1. What is the problem?
  2. What would the other person think the problem is?
  3. What is the desired outcome?
  4. What relationship do I have or want to have with the other person?

In several occasions, I even wrote out the answers rather than mentally reflect on them.  You may also consider asking your counterpart to bring their own responses in preparation for the discussion.

Recommended Resources

Below are just a few recommended resources to help you prepare for difficult or crucial conversations.  I’ve found them helpful in providing some guidance to handling those situations that are never defined in a project management book.

After all, no one said it was going to be easy, but it will be worth it.

Dr. Andrew Makar is an IT program manager and the author of several Microsoft Project Training tutorials.  Additional project management tips can be found at  Special thanks go out to Johnn Audtrisch for his contributions to the article.


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