How To Be Assertive Without Sounding Like a Jerk

Let’s get one thing straight: being polite doesn’t mean you’re winning.

If you think tossing some “please” and “sorry” into your sentences makes you sound strong, I have bad news (and a coffee-stained whiteboard that’s seen more debates than Congress) that says otherwise.

Most people think “nice” equals “powerful”, but here’s the kicker: politeness is JUST verbal couch-sitting. The less polite someone is with you, the more power you feel they have.

Challenge #1: “I Don’t Want to Offend Anyone”

Cool, then you’re choosing to be a background character. Politeness is a verbal seatbelt: safe but restrictive. While some cultures bow physically; we all bow with words and hedges.

But the problem? You don’t steer the car in a passive seatbelt.

Fresh Dad Life Parallel: If I don’t tell my kids “We’re leaving in five minutes,” they think it means “five hours later.” The clearer the message, the quicker the action.

Challenge #2: “How Can I Be Direct Without Being a Jerk?”

Simple: drop the verbal gymnastics. No “I was wondering if,” “maybe,” or “just a quick question.” Say it plain and simple.

Examples:​
❌ “Would you maybe consider joining the meeting tomorrow?”
✅ “Please join the meeting tomorrow.”

❌ “I was thinking we could try this approach.”
✅ “This is the best approach.”

Challenge #3: “What If They’re Bossing Me Around?”

If you’re dealing with a clear superior, respect is your power tool. But in the everyday blur of power, owning your voice is your secret weapon.

Challenge #4: “Won’t Being Blunt Backfire?”

Politeness isn’t respect; it’s withheld power. Assertiveness is saying what you need, clearly and respectfully, no mumbling or caveats allowed.

Challenge #5: “How Do I Practice Assertiveness?”

Try this:

• Pick your message.

• Strip it down to the simplest form.

• Drop all the “ifs,” “buts,” and “sorrys.”

• Observe how the room changes when you speak clearly.

Bad Advice Bonus: If your polite requests sound like elevator music (soft and forgettable), it’s time to change the tune.

Final Word: Politeness might keep you comfortable, but it’s directness that commands respect. Own your words or expect to be lost in the noise.

“Be so clear they have no choice but to listen.” — Me, just now.