Charismatic Assholes

Me: Okay, okay — I know you’re buttering me up before you slap me in the face with a big number. Why don’t you just say it. Maybe it won’t even sting.

They laughed. Then dropped the price.

After the call, someone asked me: “How do you get away with that?”

I shrugged. “I just said the thing everyone was thinking.”

That’s the superpower: being a charismatic asshole — the kind of person who bulldozes with a smile.

Dominance Signalling

Boldness feels like brilliance. It’s evolutionary. We mistake confidence for competence — especially when the stakes are high.

📚 One study found that people rated those who spoke first and most often as more capable. (Anderson & Kilduff, 2009)

In a sea of overthinkers and disclaimers, the person who just says it — wins attention.

They cut through the fog.

Certainty is magnetic.

Even when it’s borrowed. Even when it’s fake.
That’s why we crave job titles, five-star reviews, and 30-day guarantees.

Certainty soothes us — even if it’s just good packaging.

The Warmth–Competence Tradeoff

Harvard psychologist Amy Cuddy found we size people up in two ways:

• Warmth (“Do I trust you?”)

• Competence (“Do I respect you?”)

Ideally, you want both. But when the pressure’s on — Deadlines looming. Deals on the line.

We default to competence.
In crisis, we’d rather follow someone sharp than someone soft.

Decisive beats delicate.

How can we do both?

But unchecked dominance can backfire.

Without context or care, it slides into aggression — and aggression without rapport shuts people down. If the person you’re speaking to is insecure, uncertain, or already on edge, forcefulness won’t land — it’ll repel.

That’s why I’ve come to believe: assertiveness alone isn’t enough. The real superpower is combining strength with softness. Clarity with charm.

It’s why I aspire to be what I jokingly call a charismatic asshole — someone who can say the hard thing, but make you laugh while hearing it.

They’re not bullies. They’re not tyrants. They’re disarming. Persuasive. Sharp — but rarely cruel.

What makes them effective is the mix:

• Charm: Humor, warmth, emotional intelligence.

• Dominance: Precision, conviction, calm control.

They don’t explode. They deliver. Sometimes it’s a joke. Sometimes it’s a truth bomb.

But it’s always intentional.

Tools they use?

• Humor to lighten the punch.

• Framing to align on goals.

• Selective fire — they don’t argue for fun. Only when it matters.

It’s not about being loud. It’s about being undeniably clear — and oddly likable while doing it.

Moments to be the Charismatic Asshole this city meeting needs but doesn’t want

• When the room is stuck:

  “We’re circling — want me to throw out a next step?”

• When people spiral in vagueness:

  “What’s the actual decision we need to make here?”

• When everyone’s hedging:

  Drop the ‘maybe.’ Say: “Here’s what I think we should do.”

• When someone needs a nudge:

  “You’re smart — I think you’ve got a stronger take than that.”

• When energy drops or tension builds:

  “This is feeling like a hostage negotiation. Let’s simplify.”

• When action beats agreement:

  “Let’s make a call and adjust if we’re wrong.”

• When the truth needs saying:

  Say the thing everyone’s thinking — with a grin.

Parting words

In the modern workplace, being endlessly accommodating doesn’t make you admired — it makes you forgettable.

Master the art of the charismatic asshole — and you’ll find people don’t just tolerate your honesty… they crave it.

Until next time,

Ajay