Questions Behind Closed Doors

Roberto Giannicola
Dec 3, 2025
4 min read

Today’s a bit different.

I’m answering questions I hear most often in coaching sessions, workshops, and behind closed doors with leaders who won’t ask them publicly.

Some of these are questions from dominant leaders, others come from HR professionals and team members trying to navigate these intense personalities without getting steamrolled.

I’ve kept the answers short and direct. If something hits home, the linked newsletters go deeper.

Think of this as your quick reference guide for the patterns I see every single day in my work with brilliant but difficult leaders.

About Me

What’s your Enneagram type? Type 8. The Challenger. The intensity is real, and I’ve learned to channel it rather than let it control me. This is me

Why do you only work with “difficult” leaders? Because I was one. I’ve been the guy pushing people away with intensity, thinking control was strength. I’ve stumbled, caused discomfort, and learned to upgrade. Now I help leaders make that shift before they lose what matters most. This is me

What’s your biggest mistake as a leader? Taking my armor home. I controlled weekend plans the way I controlled projects, until people stopped offering input because it didn’t matter anymore. That woke me up. The Armor That Followed Me Home

Questions Dominant Leaders Ask Behind Closed Doors

“My team says I’m intimidating. So what?” It’s costing you the one thing you can’t afford to lose: their honesty. When people manage you instead of being real with you, you’re leading blind. [See the real cost] Brilliant But Difficult - And Afraid of Irrelevance

“Why should I care about feelings when we have deadlines?” Because you can’t logic people into motivation. Your technical brilliance got you here, but it’s becoming your leadership blind spot. [Full breakdown] You’re right. And that’s the problem

“I’m not controlling, I just have high standards.” If everything funnels back through you, if people walk on eggshells, if they don’t bring you problems, you’re controlling. The data from 360 reviews doesn’t lie. [See the patterns] From Control to Connection - whitepaper

“How do I shift from giving orders to building trust?” Stop seeing people only through their current limitations. When you approach your team with doubt and control, you create resistance. Approach them with trust and belief; that’s when transformation happens. [Learn the shift] Shifting from Control to Trust

“People say I have ‘Resting Tough Face.’ What’s the problem?” You have one-tenth of a second to make a first impression. Your intensity reads as a threat before you say a word. That’s not strength; it’s a wall between you and influence. [Master your presence] One-Tenth of a Second. That’s All You Get

“How do I know if I have a dominant style?” Take the assessment, 18 questions, no email required. Or have your team rate you. The gap between how you see yourself and how they experience you is where the work begins. [Take it now] Everyone Thinks You’re an Arrogant Control Freak

“My resistance to change comes from protecting standards. Right?” Yes, and it also comes from defending your limitations. Every time you say “That’s just how I am,” you dig yourself deeper into isolation. The deeper you go, the lonelier it gets. [Stop digging] (Argue for Your Limitation and You’ll Win. Alone

“If I delegate more, won’t things fall apart?” You’re already the bottleneck. The question isn’t whether to let go, it’s whether you’ll transform that fear into trust and watch your authority grow instead of erode. [Break free] Classic Roadblocks of Dominant High-Impact Leaders

“Why do people see me as arrogant when I’m just confident?” Because confidence invites collaboration. Arrogance shuts it down. You think you’re being direct, they think you’re dismissing them. The blind spot is that everyone sees it but you. [Close the gap] Everyone Thinks You’re an Arrogant Control Freak

“How do I lead without demanding compliance?” When you demand immediate compliance, you miss something far more important: the person’s potential to grow. If you want trust and growth, your path needs to match them. You can’t build trust through control. [Learn how] Shifting from Control to Trust

“I want my team to step up, but they hold back. Why?” Because you’ve accidentally created authoritarian dynamics. When questioning you feels risky, people stop thinking around you. They’re not lazy, they’re responding to what they sense. [See the pattern] Are You the Leader Everyone Fears?

What HR & Team Members Ask

“How do I tell my boss they’re the problem?” Lead with data, not feelings. Show them what their behavior is costing in turnover, delays, and team performance. Use their language: outcomes, impact, results. [Full approach] Classic Roadblocks of Dominant High-Impact Leaders

“When is dominant leadership actually toxic?” When it’s driven by fear instead of vision. When people comply instead of committing. When the armor becomes authoritarianism. [See the warning signs] Are You the Leader Everyone Fears?

“How do I get heard by a dominant leader without getting steamrolled?” Hold your ground, calmly, confidently, strategically. Use their first name, not their title. Ask disarming questions. Make them pause and think. Don’t match their energy with more noise. [The complete guide] How to Engage with Dominant Leaders – Dos and Don’ts

“I can’t say no, I’ll let people down.” That’s not generosity. That’s fear. Every yes you give when you mean no costs you energy, focus, and integrity. Directors and VPs struggle with this, too. Your boundaries aren’t selfish, they’re essential. [Learn to say no] You’re Not Generous, You’re Just Afraid to Say No

“My boss dismisses my ideas. What should I do?” Prepare thoroughly, back your ideas with data, and don’t back down. Show them what vulnerability looks like. Call out behavior when it’s out of line, firm, polite, and direct. They’ll respect you more. [Learn the approach] How to Engage with Dominant Leaders – Dos and Don’ts

“How do I influence a resistant colleague without authority?” Let go of past judgments. Meet them in the present moment, acknowledge their expertise, and frame change as an opportunity to expand their strengths, not a threat to their status. [The approach] The Power of the Now to Turn Resistance into Alliance