#29 The Boss Factor: Sabotaging Projects from the Inside

In project management, trusting leadership should be the foundation for success. But what happens when decisions from the top create more chaos than clarity? How far should you go in following your manager’s lead, and when is it time to push back?

We often assume that leaders have the experience and vision to set priorities, allocate resources, and guide the team toward success. But sometimes, those very decisions become the reason projects fail—or worse, the reason you end up constantly cleaning up someone else’s mess.

The Thin Line Between Trust and Questioning:

As employees, we’re taught to trust that our managers know what they’re doing. After all, it’s their job to see the big picture and make strategic calls.

But what happens when those decisions repeatedly leave you stuck in crisis mode?

I’ve been in situations where my role as a Project Manager gets derailed by poor decisions made higher up. Resources are reassigned without notice, priorities shift without proper communication, and tasks end up duplicated or poorly executed. In a perfect world, this would be a rare occurrence. But when it becomes a pattern, the tough question surfaces:

Should I keep trusting that “they know what they’re doing,” or step in before everything falls apart?

Passive-Aggressive Sabotage or Simple Mismanagement?

Here’s the tricky part—how do you know if this is just disorganization or something more toxic? In complex work environments, it’s not always easy to spot the difference between genuine mistakes and subtle sabotage.

Red flags to watch out for:

• Consistently being assigned poorly structured or problematic projects
• Priorities constantly shifting without clear communication
• Receiving contradictory instructions that create confusion or conflict
• Decisions that directly impact your performance, leaving you to fix the fallout

When the same issues happen over and over, it’s no longer just bad luck. It’s a sign that something deeper is broken.

How to Handle Leadership Failures:

Calling out your manager isn’t easy. It can be seen as challenging authority. But staying silent can be even more damaging—to the project and your own sanity.

Here’s how to handle it without lighting fires:

1. Use Data, Not Emotion: Stick to facts when raising concerns: “This change caused a two-day delay in the timeline” hits differently than “I’m frustrated because this always happens.”
2. Offer Alternatives, Not Just Criticism: Rather than directly questioning decisions, present options: “Would it make sense to adjust this approach to avoid potential delays? I’m concerned about the impact on delivery.”
3. Document Everything: Keep records of instructions, changes, and communications—not as a weapon, but as protection if things go sideways.
4. Know When to Escalate: If the same mistakes keep happening and are impacting the team or client, sometimes you need to escalate. Do it tactfully, positioning it as a process improvement, not a personal attack.

The Direct Impact on KPIs, Timelines, and Deliverables:

Poor leadership doesn’t just cause frustration — it hits where it hurts most:

• KPIs get skewed when shifting priorities make targets impossible to meet
• Timelines stretch endlessly due to back-and-forth changes and unclear directives
• Deliverables suffer as resources get misallocated or bottlenecked
• Budgets spiral out of control when mismanagement leads to costly fixes

When leadership becomes the problem, even the most skilled PMs struggle to hit their targets.

When Company Culture Fuels the Problem:

Some organizations thrive on open communication and encourage questioning across all levels. Others see it as a threat.

The result?

• Employees stay silent to avoid conflict
• Leaders continue making poor decisions unchecked
• Projects fail—not because of poor execution, but because of bad strategy

Understanding your company’s culture helps you figure out when to speak up—and when to cut your losses.

If you’re leading a team, ask yourself:

• Do I listen when my team raises concerns?
• Am I open to adjusting my decisions if new information comes up?
• Have I built a culture where people feel safe to question respectfully?

Good leaders don’t fear being questioned—they welcome it. Because real leadership is about guiding the team toward success, not just protecting your ego.

Not every manager is a true leader. Some prioritize their image over results; others simply lack the skills to handle complex projects. As Project Managers, we often end up playing the role of the fixer—the one who patches things up so the project stays afloat.

But here’s the thing: you don’t have to accept that role forever.

Real project management isn’t just about timelines and resources. It’s about knowing when to speak up, when to step back, and when to push for what’s right—even if it means questioning the person in charge.

How do you handle poor leadership? Where do you draw the line between trust and pushing back?