Change Leadership

Troublemaker or Troubleshooter?

3 min read

Why your toughest critics may be your most valuable allies.

Troublemaking vs. Troubleshooting: The Leadership Skill of Listening

“I want you to give me a reason to fire Alison,” a project manager told me.

Before I could respond, he launched into his frustration.

“She never has anything good to say about the new system. She focuses on every flaw. She’s going to turn everyone against it.”

Curious, I reviewed the project’s chat streams. Alison was indeed pointing out issues, but the majority of her comments were constructive. More importantly, her concerns weren’t simply complaints; they identified potential pitfalls. She wasn’t tearing the system down. She was troubleshooting: identifying risks that could affect customer adoption and undermine promised benefits.

A team member speaks up and gestures while making a point in a meeting as colleagues listen thoughtfully

That’s a critical distinction.

Troubleshooting

Supports success.

Troublemaking

Undermines it.

Listen for the Troubleshooting Tells

So, how can you tell the difference? Listen for these troubleshooting tells:

  • The criticism is specific.
  • It’s framed as a request for clarification (“Help me understand this…”).
  • It’s constructive and often comes with a reasonable suggestion.
  • It aligns with goals, KPIs, or governance.
  • It identifies a potential risk rather than simply expressing personal frustration.
  • It’s presented as an observation or opinion, not a personal attack (“In my experience…”).

On the flip side, people who are undermining a project may rely on vague, sweeping criticism without engaging in problem-solving. You might hear comments like:

  • “This looks terrible.”
  • “Our customers will hate this.”
  • “I said from the start this wouldn’t work.”
  • “Who approved this?”
  • “This is a waste of my time.”

But words alone don’t tell the whole story. Even an emotional or poorly expressed objection may point to a legitimate problem.

The distinction becomes clearer when leaders explore the concern, examine the evidence, and observe whether the person is willing to help resolve the issue.

Listen to Understand, Not to Rebut

People on the front lines are often the first to spot missing requirements or functionality gaps.

The best leaders don’t listen just to rebut; they listen to understand.

When you remove ego from the equation and focus on the value of feedback, you don’t just build better projects—you build a culture where critical thinking and problem-solving thrive.

The next time someone like Alison challenges a new initiative, ask yourself:

Is she causing problems, or is she trying to prevent them?

The difference could determine the success of your project.

Cirrus Change: Every Team can be Ready for Change

Melinda Starkweather is co-founder of Starkweather Association Services and developer of the Cirrus Change Readiness platform. She is a coach and speaker on change management.

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Cirrus Change Readiness helps leaders find where people and workload risks hide before they slow a new system or initiative.

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