How to Motivate and Empower the Five Most Challenging Workplace Personas

At the beginning of my government career, I often worked with people labeled “challenging.” They were difficult to work with, would disengage from the team and cause disruption. It wasn’t until I became a senior leader and led multiple city and statewide projects that I realized most people are not bad employees. They just needed to be managed, motivated and engaged differently to become contributing team members. 

Often, leaders give up and stop encouraging employees they feel are difficult to manage. However, spending a little time identifying the driving force behind the employee’s disruptive actions — and helping them redirect their perceived negativity — not only demonstrates your leadership ability but can make a difference in their engagement levels.

Opening a dialogue and using the below guide can help turn disengaged and seemingly difficult employees into team players and project champions. 

• The Challenger

What they might say: “Why are we doing it this way?”

Engagement Style: Constantly asks for clarification on why certain activities are needed.

Employees displaying challenger behavior might need to feel heard or genuinely do not understand their assignment. Improving the challenger’s engagement level takes patience. 

To help challengers use their skill of asking questions, assign them the task of identifying what questions the team might get from anyone reviewing the project. That information could help the team anticipate risk and be used to develop better status reports and business case documents.

• The Saboteur 

What they might say: “This is never going to work.”

Engagement Style: Constantly disagrees with the leader.

I know it is hard to believe, but the saboteur’s behavior might be out of fear. Fear of losing their job if the project is successful. Fear of not fully understanding how to perform their assigned task.  

To turn the saboteur’s negative energy into a positive one, try talking to them to learn the source of their opposition to their assigned task(s). Maybe more training is necessary to help them feel more comfortable. Perhaps they need to understand what happens to their job after the project ends.

• The OMG

What they might say: “This project is going to cause so many other problems.”

Engagement Style: Constantly points out what could go wrong.

Instead of being dismissive, keep listening to the OMG, as they may identify a problem or risk you overlooked. Give them the task of thinking through all the things that could go wrong and possible solutions if the situation occurs.

• The History Professor

What they might say: “We already tried this in 1982!”

Engagement Style: Constantly brings up what was tried or done in the past.

The history professor usually has a wealth of historical agency knowledge, including past mistakes, lessons learned and people to know.

Instead of becoming frustrated with the history professor’s comments, allow them to demonstrate their expertise by documenting the lessons learned from past projects, noting what worked and what didn’t.

• The Show Me The Money

What they might say: “I just don’t see how this will improve anything.”

Engagement Style: Is not motivated until they see results. 

As a leader, you must engage this person often and provide frequent updates on the small wins and milestones as the project progresses. Usually comes around quickly when they become more aware of the frequent changes