Workplace Sabotage: Is It Happening Right Under Your Nose?

How Accidental Self-Sabotage Might Be Quietly Killing Your Company's Potential

In 1944, the OSS (predecessor to the CIA) distributed a classified field manual to its spies. The manual outlined tactics for sabotaging enemy organizations from the inside.

These tactics included behaviors like:

Insist on following every rule, even when shortcuts are more efficient
Play dumb, even when you understand
Constantly bring up off-topic issues that derail conversations
When asked simple questions, give long-winded, confusing responses
Rehash decisions that have already been made

It was an espionage playbook for sowing dysfunction and inefficiency.

Here's the troubling reality—these same behaviors appear constantly in today's organizations. Not deliberately, of course, but with the same damaging effects. I call it "accidental self-sabotage," and it's particularly common in fast-growing startups where processes struggle to keep pace with expansion.

Sound Familiar? The Hidden Costs

Consider your own workplace. Have you noticed these behaviors cropping up in meetings and daily operations? Tangential issues constantly derailing discussions? Simple questions met with convoluted, hard-to-follow explanations? Decisions that were settled weeks ago being repeatedly reopened?

These patterns drain more than time. They erode productivity, deplete team morale, and directly impact your bottom line. For startups and scaling companies, where resources are precious and speed is essential, this hidden inefficiency can mean the difference between success and failure.

Root Causes and Practical Solutions

Accidental sabotage can stems from multiple sources: well-intentioned but excessive structure, risk aversion among employees, or outdated processes that persist after their usefulness has ended.

Some practical steps startup leaders can implement quickly:

Use a clear decision rights framework (like RACI) that reduces bottlenecks by defining who makes which decisions
Institute quarterly initiative reviews to identify and eliminate redundant projects that consume resources
Ask frontline employees to identify "stupid rules" that slow them down—they tend to feel bureaucratic friction first
Invite experienced employees to review onboarding processes to ensure you're not teaching new hires counterproductive behaviors
Throughout these processes, focus on identifying problematic behaviors rather than labeling individuals—it's simply more productive

These operational fixes can help. But for growing companies, there's another critical factor at play.

The Leadership Development Opportunity

Many startups and growing companies hire or promote technically brilliant individual contributors into management positions without proper leadership training. This can be particularly challenging for fast-growing tech companies, where technical expertise is abundant but leadership experience may be limited.

Without adequate leadership skills, organizational patterns emerge: micromanagement becomes common, communication breaks down, and delegation happens inconsistently. These patterns—not necessarily the individuals themselves—become sources of accidental sabotage.

Leadership development can be a powerful antidote to this problem. With proper training, managers can learn to recognize and reduce accidental self-sabotage. They can develop essential skills in systems thinking, clear communication, effective delegation, and collaborative problem-solving.

For startups especially, where small teams have outsized impact, improving leadership capability can create exponential returns.

Transform Your Managers, Transform Your Results

That's where I can help. I work with growing companies to help technically skilled managers become effective leaders. My workshops don't offer abstract theory. They provide practical frameworks your managers can implement immediately to reduce friction and boost productivity.

Participants leave with a shared language for problem-solving and actionable tools they can apply the very next day. This is particularly valuable for distributed teams or those experiencing rapid growth.

Ready to Reduce the Sabotage?

Join me for an upcoming workshop:

In-person Workshop – I run a public version of our foundational workshop in Petaluma, California twice a year. It's a great opportunity for SF Bay Area leaders to boost their leadership skills while visiting wine country.
Virtual Workshop – Quarterly, I run a virtual version of this foundational workshop online. Perfect for distributed teams.

Early bird discounts are available for both options.

Don't let workplace sabotage hold your company back. Schedule a conversation with me to discuss your specific needs or go ahead and reserve your seats today.

Many thanks to Maria Ginsbourg for her help with editing and creative-thinking tasks!

The leadership development curriculum I teach—including the battle-tested Leadership and the Middle Path—was designed and developed by world-class organizational development expert Chris Holmberg of Middle Path Consulting.