How many times do you ask for exactly what you want?

50% of the time?

30% of the time?


How many times have you left a conversation feeling like you let someone else impose their will on you?

Instead of standing your ground, you wilted like a supple fern in a hurricane.

Well, I’m about to make you the hurricane.

(Albeit, a nice hurricane, the kind of hurricane that you’d like to have over for dinner and drinks)

Today we’re going to cover the subtle art of being assertive without being aggressive.

Why does this matter?

Unless you’re Tom Hanks in Castaway, and the only person you talk to is a volleyball named Wilson, you’ll be interacting with other people.

This means you’ll need to:

  • Build relationships
  • Make requests
  • Negotiate favors
  • Champion your ideas
  • Navigate the choppy waters of politics

After reading this, you’ll not only be able to stand your ground, you’ll be able to create win/win outcomes that will build relationships.

No more supple fern.

Image Credit: Jeremy Bishop

Here’s the quick hit checklist to make you 10x more assertive when the stakes are highest.

Lead with empathy.

A smart friend of mine recently said this and it struck me: How often are we approaching conversations focused on other people’s needs first? It’s important to realize that we’re all people, with drivers and needs.

Consider the other person’s perspective before making assumptions about their motives. Maybe they aren’t evil and out to get your job, maybe they just haven’t had lunch yet.

This will be massively helpful for the next strategy.

(Further reading: Win Your Case, Gerry Spence)

Create win-win situations.

This cannot be overstated. Win-win situations are crucial. People need to feel like they got a fair deal. In fact, if you and a friend got $100 to split and they decided that you would only get $20, chances are likely that you would decline the whole deal. Even though you would come out with twenty dollars you didn’t have before.

This article from the Harvard Business Review shows how to tactfully disagree with someone more powerful than you. Subtle things like asking for permission, and not using judgment language create the environment for a win-win.

The more win-win situations you’re willing to create, the more goodwill you’ll create, and people like helping people they like.

Humans are funny like that.

Be willing to negotiate.

Depending on what the situation is, you may be able to “give up” something you don’t feel strongly about to protect something you do value. In negotiation, this is called bracketing. Negotiation is simply artfully uncovering other people’s needs.

(Further reading: Never Split The Difference, Chris Voss)

Keep your emotions in check.

Emotions are great, who doesn’t love watching How To Lose A Guy In 10 Days? (I do.) However, if you’re making a request or a proposal, it may be helpful to avoid visceral knee jerk reactions.

In the The 48 Laws Of Power, author Robert Greene talks about managing emotions:

“If the inner turmoil caused by our emotions trends to make time move faster, it follows that once we control our emotional response to events, time will move much more slowly.”

Simple tools like box breathing come in handy to short circuit the body’s fight or flight response.

Limit qualifying words.

Words that are tentative can kill an otherwise persuasive statement by undercutting your credibility. Avoid using “I guess”, or “Sorta”. Instead, use more powerful language: “Based on my research…” or “In my experience…”

Conversely, if you don’t know the answer to something, be transparent and say “I don’t know.”

Give them options.

This is a little counter intuitive. I mean, don’t powerful communicators impose their will on everything and everyone? Not so much, often, the best thing you can do is present options to people, and let them choose from the choices you’ve provided. This has two distinct advantages:

1. You’re making it easy for them. Most of us make thousands of decisions per day causing ego depletion. By presenting options, they don’t have to think as much. People love that.

2. They are YOUR options. Control the options, influence the outcome. (Caveat: create a win-win situation.)


“What do you recommend?”

You: “Well, as I see it, we’ve got two ways to go, A or B. which one do you think is best for you?”

Silence. It’s golden.

After you lay down the options, shut the mother flipping hell up. You are now entering what I call “the vacuum”.

Your first, second, and third instinct will be to fill it with something, anything.


Let the silence do the work for you. Breathe. Become the silence.

They should be the next person who talks.

With these tools, you are set up for success the next time you need to be assertive without being a jerk.

Next Step

These strategies work best with people you’ve built relationships with.

I made you a free guide to help you get out of your own head and effortlessly join group conversations.

Get it here and start building those relationships.

Originally published at