When Pride Gets Quiet: How to Lead High Performers Who Withhold Mistakes
Pressure can cause team members to feel the need to perform
Ritika Vijay
, Fri 13 June 2025
On the surface, Micheal looked like a dream hire. As the VP of Technology at a fast scaling fintech firm, he moved fast, delivered faster, and held his team to exceptional standards. Colleagues praised his work ethic. The CEO trusted his judgment implicitly. Micheal didn’t just meet deadlines, he bulldozed through them, building systems that scaled and workflows that hummed with efficiency.
But there was something building slowly.
It wasn’t anything major at first. A bug in the product’s dashboard that should’ve been caught. A delay in a data migration project with no proactive heads up. A misconfigured server that took days to surface. These were minor errors, but they shared a troubling theme: no one knew about them until they became unavoidable.
Micheal’s instinct wasn’t to hide. It was to fix it. Quietly. Silently. After all, in his mind, owning mistakes was a weakness. Admitting fault would diminish his authority. The less leadership had to worry, the better. But that’s where the danger crept in: small mistakes left unspoken that compounded over time. And for a business growing fast, every day a mistake goes unaddressed is a day risk quietly metastasizes.
Why Pride Fueled Silence Poses a Business Risk:
When Micheal chose not to surface small mistakes, he didn’t do it out of malice, he did it out of a sense of responsibility. But that sense of “I’ll fix it myself” gradually evolved into a pattern of withholding information. In a leadership role, withholding, even unintentionally, becomes dangerous not just for the team, but for the organization.
Delayed Visibility = Escalated Cost: What starts as a minor issue can quickly evolve into a major operational disruption when not surfaced early. Small bugs become cross functional fire drills simply because leadership wasn't informed in time.
Poor Data Leads to Poor Decisions: When issues are hidden, leaders make strategic decisions based on incomplete or inaccurate information which impacts everything from resource allocation to investor communications.
Silence Breeds More Silence: When a senior leader withholds problems, it sets a cultural precedent. Teams may follow suit, eroding trust and psychological safety. Without a culture of transparency, systemic risks go unnoticed until they explode.
How to Lead Through Pride: 5 Steps to Support High Performers Who Struggle with Transparency
When a high performing employee begins withholding mistakes out of pride, leaders must act quickly, but thoughtfully. Here's a clear 5 step approach to address the issue while preserving trust and performance:
- Start with a Personal Check In
Before assuming the worst, pull the employee aside, and have a transparent conversation of what is going on. It could be work related stress or a personal issue. Showing empathy, not suspicion opens the door for honest dialogue and signals that you care about the person, not just the output.
- Coach to Understand the ‘Why’
Dig deeper into why mistakes weren’t communicated. Avoid blame, instead, ask, “What made you feel like you had to handle this on your own?” Often, pride is a shield for fear or pressure. Use coaching to uncover the root cause and align on shared expectations.
- Redefine Strength and Normalize Vulnerability
Clarify that real leadership isn’t about perfection, it’s about visibility. Frame early communication as a strategic behavior. Then model it yourself. Share your own mistakes in team settings and how transparency helped prevent larger issues. This redefines what “strong leadership” looks like. Opening up to that vulnerability will also build a stronger relationship.
- Create Regular Spaces for Open Conversations
Build simple routines that make it easy, and expected, for your team to surface issues early. Something as quick as a weekly 15 minute “Red Flag Roundup” can give everyone a low pressure space to share blockers or risks. Pair these check ins with transparent performance updates so everyone knows how their work stacks up against expectations. When transparency becomes part of the rhythm, it feels safe and normal.
Make it a point to praise people not only for delivering results, but for speaking up when something’s off, even if they had a hand in the mistake. When someone flags a problem early, thank them publicly. This shows the team that being upfront isn’t damaging, it’s leadership. Over time, this reshapes the culture from “look perfect” to “work smart and stay accountable.”
Final Thought: When Pride Clouds Visibility, Performance Suffers
High standards are an asset, until they’re paired with ego that discourages openness. Even top performers can become blind spots when they value perfection over transparency.
The takeaway for leaders is clear: Don’t wait for avoidable crises to expose cultural weaknesses. Create an environment where speaking up is rewarded, not penalized. Redefine strength as accountability, not invincibility. Because in business, it’s rarely the initial mistake that causes the most damage; it's the silence that follows.
