The Failures of Leadership in IT: Recognizing Dysfunction and Rising Above It

Leadership failures in IT are not just frustrating—they can be deeply damaging to teams, projects, and entire organizations. Many of these failures follow predictable patterns, driven by leaders who lack technical expertise, resist change, or prioritize self-preservation over team success. Worse, many leaders fail to protect their teams, leaving employees to fend for themselves in environments of unrealistic expectations, poor decision-making, and organizational politics.

This article explores common leadership failures in IT through the lens of archetypes, inspired by Carl Jung’s psychological models. Each archetype reflects a recurring leadership dysfunction, how it impacts teams, and how both employees and leaders themselves can recognize and overcome these flaws.

1. The Shadow King: The Controlling Dictator

Failure Mode: Micromanagement and Fear-Based Leadership

The Shadow King is obsessed with control, often due to personal insecurity. They distrust their teams and rule through fear, stifling innovation and autonomy.

Impact on the Team:

• Employees feel powerless and disengaged.

• Innovation is suppressed because mistakes are punished.

• Team members become risk-averse and avoid taking initiative.

How Individual Contributors Can Work Effectively with This Leader

✅ Document Everything: Keep records of decisions to avoid blame games.

✅ Find Small Areas of Autonomy: Look for ways to take ownership of work without triggering resistance.

✅ Build Peer Alliances: Strength in numbers can help push back against overreach.

How Leaders Can Improve:

✅ Delegate with Trust, Not Control: Empower employees instead of micromanaging.

✅ Recognize That Fear Kills Innovation: Encourage open discussions rather than punishing failure.

✅ Measure Outcomes, Not Process Control: Focus on results rather than minute details of execution.

2. The Perfectionist Leader: A Caricature of Humanity

Failure Mode: Trying to Be Perfect, Alienating Everyone

Impact on the Team:

• Employees feel they will never measure up.

• Communication stops as people recognize that speaking up will be criticized.

• Finger-pointing and criticism of others replaces work.

How Individual Contributors Can Work Effectively with This Leader

✅ Clarify Expectations: Ensure feedback is specific, not an endless cycle of corrections.

✅ Push for Ownership of Your Work: Set boundaries on excessive revision cycles.

✅ Don’t Internalize the Leader’s Standards: Recognize that perfectionism is their issue, not yours.

How Leaders Can Improve:

✅ Embrace ‘Good Enough’ When Appropriate: Perfectionism kills progress.

✅ Trust Your Team to Deliver: If everything collapses without you, you’re failing as a leader.

✅ Be More Human, Less Perfect: People don’t follow perfection—they follow authenticity.

3. The Showman Leader: All Style, No Substance

Failure Mode: Prioritizing Optics Over Execution

Impact on the Team:

• Decisions are made based on optics, not feasibility.

• Technical teams feel undervalued and unheard.

• Employees lose trust in leadership as flashy initiatives fail repeatedly.

How Individual Contributors Can Work Effectively with This Leader

✅ Translate Their Vision into Actionable Steps: Ask clarifying questions about execution and accountability.

✅ Manage Expectations with Data: Use historical project timelines to counter unrealistic demands.

✅ Document Everything to Hold Leadership Accountable: Keep records of shifting expectations.

How Leaders Can Improve:

✅ Balance Messaging with Execution: Engage directly with teams doing the work.

✅ Be Honest About Challenges: Transparency builds trust.

✅ Let Success Speak for Itself: Deliver tangible results instead of chasing visibility.

4. The Sales-Driven Leader: Promising the Impossible

Failure Mode: Making Unrealistic Commitments

This leader prioritizes sales, marketing, or executive relationships over execution. They promise features and deadlines that the technical team cannot realistically meet.

Impact on the Team:

• Engineers are forced into crunch mode to meet impossible deadlines.

• Quality suffers as teams rush to deliver.

• Morale drops, leading to burnout and turnover.

How Individual Contributors Can Work Effectively with This Leader

✅ Insist on Written Scope Agreements: Prevent scope creep with clear documentation.

✅ Use Historical Data to Justify Deadlines: Show real-world project timelines.

✅ Find an Executive Sponsor for Technical Realism: Seek out leadership allies who understand feasibility.

How Leaders Can Improve:

✅ Consult Engineers Before Making Commitments: Reality-check promises before making them public.

✅ Push Back on External Pressure: Manage expectations with customers and executives.

✅ Celebrate Sustainable Success, Not Just Heroic Efforts: Reward realistic planning over firefighting.

5. The Legacy Executive: Out of Touch and Resistant to Change

Failure Mode: Clinging to the Past

This leader once had technical knowledge but hasn’t kept up with industry changes. They resist modern approaches, making decisions based on outdated models.

Impact on the Team:

• Employees bypass official processes to use modern tools.

• Company lags behind competitors who embrace innovation.

• New hires become frustrated with outdated systems and leave.

How Individual Contributors Can Work Effectively with This Leader

✅ Demonstrate Value with Small Wins: Introduce modern solutions through pilot projects.

✅ Leverage Industry Standards: Use external success stories to support proposed changes.

✅ Find Champions Within Leadership: Align with forward-thinking executives.

How Leaders Can Improve:

✅ Stay Curious, Not Defensive: Be open to learning from your team.

✅ Encourage Controlled Experiments: Allow teams to test and validate modern approaches.

✅ Prioritize What Works Over What’s Familiar: Leadership is about results, not nostalgia.

6. The Trickster: The Chaotic Visionary

Failure Mode: Constant Change Without Execution

The Trickster thrives on disruption, always chasing the next big thing—AI today, blockchain tomorrow—but rarely following through.

Impact on the Team:

• Projects are started and abandoned before completion.

• Employees feel whiplash from ever-changing priorities.

• Stability and deep expertise are sacrificed for the sake of novelty.

How Individual Contributors Can Work Effectively with This Leader

✅ Clarify Goals in Writing: Pin down priorities with clear documentation.

✅ Push for Small, Achievable Wins: Insist on delivering working versions before moving to the next idea.

✅ Protect Your Own Career Development: Focus on building skills that will outlast leadership changes.

How Leaders Can Improve:

✅ Limit Disruptions with Structured Innovation: Test new ideas in controlled pilots before committing full resources.

✅ Trust Your Team to Deliver the Execution: Set a vision, then step back.

✅ Recognize That Change Fatigue Is Real: Stability is necessary for success.

Final Thoughts: How to Rise Above Bad Leadership

Leadership failures in IT are inevitable, but suffering under them doesn’t have to be. Whether you’re an individual contributor looking to protect your career or a leader trying to improve, the key is recognizing these patterns and taking action.

For individual contributors: Learn to navigate dysfunction, document decisions, and build networks inside and outside the company. If necessary, prepare an exit strategy.

For leaders: Your role is not to be perfect, nor to have all the answers—it’s to build an environment where your team can succeed. If you see yourself in these archetypes, take it as an opportunity to evolve.

Bad leadership is fixable—but only if you’re willing to recognize it.