Ep 92 Career: How to deal with difficult and creativity killing people

Show notes

Creativity is messy. It’s subjective. And when you put strong opinions, egos, and ambiguity into the same room, it’s only a matter of time before you run into difficult people. In this episode, Stephen breaks down the psychology behind difficult work relationships, identifies the four main personality types you’ll encounter, and shares practical strategies for dealing with them productively.

Why this matters:
You can’t do great work without trust. And trust breaks down fast when collaboration turns toxic. Understanding personality dynamics isn’t just EQ—it’s essential to protecting your team, your creativity, and your sanity.

Key Segments:

1. What “Difficult” Actually Means

• Distinguishing between unprofessional (HR-level) behavior and difficult personalities.

• Difficult people kill creativity, crush team spirit, and only want their way.

2. The Four Workplace Personality Types

• Passive: Avoid conflict, downplay their needs, often ignored or overruled.

• Aggressive: Loud, dismissive, dominate conversations, control-oriented.

• Passive-Aggressive: Agree publicly, undermine privately. Politically slick, emotionally slippery.

• Assertive (ideal): Balanced, direct, respectful, collaborative. Speaks up without tearing others down.

3. Spotting Difficult Behavior

• Always making it about “I want…” or “I need…”

• Refusing responsibility and blaming others.

• Treating opinions as facts.

• Using tone and intimidation to silence input.

• Undermining others behind the scenes.

4. Productive Tactics to Handle Difficult People

• Start with yourself: Reflect on your reactions, hot buttons, and assumptions.

• Put the shoe on the other foot: Try to understand their emotional POV.

• Seek second opinions: Get trusted, honest feedback before acting.

• Focus on facts, not emotion: Don’t cloud the issue. Stay centered on the work.

• Have 1:1 conversations: Don’t escalate too soon. Avoid public confrontations if possible.

• Use “we” not “I”: Frame the issue as a team challenge, not personal conflict.

• Focus on 1-2 core behaviors: Avoid laundry lists. Keep it actionable.

• Watch their actions, not words: Some will say the right things and never change. Stay alert.

5. When the Soft Skills Don’t Work

• Use customer testing as a tie-breaker.

• Involve difficult people early to build buy-in.

• Change your process: structure brainstorms, rotate airtime, set boundaries.

• Mirror their behavior back: “What if I did what you’re doing?”

• Redirect energy to people who want to collaborate—let outcomes drive organizational jealousy.

6. The Real Goal: Be Effective, Not Right

• Creativity isn’t about ego. It’s about team progress and better outcomes.

• Humility is the hallmark of true talent.

Closing Truth:

“Everyone’s been the difficult person at some point. But don’t let them stop you from being creative. Try to help. Try to connect. But if they won’t change, protect your peace.”

Call to Action:

• Take inventory of your team dynamics.

• Try one technique this week. Or better yet, be the person who helps the difficult ones evolve.

Tagged as:
collaboration skills creative resilience creativity challenges difficult colleagues handling criticism managing difficult people personality types productive teamwork Stephen Gates The Crazy One podcast workplace personalities workplace success