If You’re Afraid of Feeling Manipulative


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What do we actually mean when we say we’re afraid of feeling manipulative? Today's essay explores how respecting boundaries, avoiding force, and clarifying your intentions lets you ask for what you want without feeling sleazy.

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If You’re Afraid of Feeling Manipulative

How do very successful people ask unapologetically for what they want while the rest of us offer endless caveats or don’t speak up at all?

I’ve been thinking about a topic that came up in my conversation with Gagan Biyani at the Snafu Conference: manipulation.

Gagan has built his career in growth marketing: a subset of marketing and sales where data and storytelling can combine to create exponential user adoption. Gagan did that as the co-founder and CEO of Udemy, on the growth team at Lyft, as the founder of the food delivery company Sprig, and now as the CEO of edtech company Maven.

(Disclosure: I’m an investor in Maven.)

One of the reasons a lot of people are hesitant to advocate for themselves is the fear of promoting too heavily or making promises they can’t keep. In other words, of feeling manipulative.

The Fear of Manipulation

When I asked Gagan about manipulation on stage, he said that a fear of manipulation negates another person’s agency. Each person in a transaction is a sovereign individual responsible for their own decisions, Gagan argued, and manipulation doesn’t give enough credit to their ability to make decisions for themselves.

We can’t manipulate people, and shouldn’t worry about it.

It is true that everyone is responsible for their own behavior. I agree that the very people who are overly worried about manipulating others are the ones who’d benefit from worrying a little less. But as a painfully shy boy who used to be so afraid of being manipulative that I didn’t even try, I’m empathetic to feeling manipulative, as well.

Let’s Define Manipulation

Onstage at Snafu, Gagan said that he’s uncomfortable stating that courses offered by his company Maven will protect students against AI replacing their jobs. He is, however, comfortable saying Maven can help.

For me, it’s helpful to define manipulation. According to the Oxford English Dictionary, “Manipulation is the dishonest or devious control/influence of people or situations to one's advantage.” I’d paraphrase this as lying or deceiving at another person’s expense or my own benefit.

Power dynamics do exist. Buyers can be nudged past their own clarity.

Manipulation is trying to persuade with deception or without taking into account what’s best for the other person.

Boundaries

I’ve written about boundaries, and the ways in which clear boundaries can make negotiation and self-advocacy easier.

Boundaries are the lines someone holds – stated or unstated – past which they don’t want to go: whether in buying a product, going on a date, or just continuing to engage. But boundaries aren’t often explicitly stated. They are usually unstated or even unacknowledged by the person holding them.

The reason sales is stigmatized is because the worst salespeople push boundaries. The telemarketer who won’t stop calling and the used-car salesman who continues to insist on a sale are pushing boundaries; they’re not respecting a clear or unspoken “no.”

For those of us afraid of being manipulative, we’re actually afraid of pushing others’ boundaries.

Don’t Use Force

I first heard the phrase “don’t use force” from Doug Kirkpatrick, and liked the idea enough to write a chapter about it in Responsive: What It Takes To Create a Thriving Organization.

I detest pressure tactics and emotional bullying, perhaps because I was bullied growing up. The absence of force and pressure is the heart of my preferred method of relating, of influence and selling.

Of course, pressure can work. We can compel compliance. But pressuring someone to do something doesn’t feel good for either person during or afterwards. That feeling is what we’re afraid of when we’re afraid of feeling manipulative.

Most of us want to connect with other people. We want to help others. We may also want to be more influential, and even to change other people’s behavior, but we want to do so without judgment and pressure.

Pressure – the use of force to get what we want – is manipulation.

It’s Okay to Be Hesitant

I used to judge myself for my hesitancy to speak up. I compared myself to other people who unapologetically promoted themselves and their work, and found myself lacking.

It is easier to get ahead – to promote yourself, ask for what you want, ask someone out on a date – if you're not worried about being manipulative. But I don’t want to feel sleazy or manipulative. I don’t want to use force.

And as someone who spent years not self-advocating out of the fear of feeling manipulative, I have empathy for that feeling.

The path forward is to respect boundaries, not use force, and challenge yourself to take small steps toward asking more.


3 Things I’ve Loved This Week

Quote I’m Considering

In 2015, tennis player Novak Djokovic was asked about his exceptional success. His response: "I can carry on playing at this level because I like hitting the tennis ball."

Video I’m Watching

Founder-Led Sales with Gagan Biyani at the Snafu Conference

video preview

This interview was ostensibly about growth marketing in the age of AI, but we covered a lot of ground: lessons from Udemy and Lyft, the importance of founder-led sales, why Gagan is an AI optimist, and more.

Personally, I’m rewatching the video to practice and refine my interview technique.

Book I’m Reading

Moneyball: The Art of Winning an Unfair Game by Michael Lewis

I’ve watched the movie Moneyball, but after reading Going Infinite, I was curious to read more of his books.

Unsurprisingly, Moneyball is excellent. The longer format gives time to add color to the hilarious baseball personalities. I’m also fascinated by Lewis’ ability to write so vividly, and in a style that translates so well to the screen.


Want more?

Read these books

Thing Might Work: A Collection of How-Tos is a collection of experiments. These are first-person essays on how to write, fast, raise a puppy, buy a used car, buy a house, tell better stories, sell your work, and navigate change.

Responsive: What It Takes to Create a Thriving Organization isn't just a business book. It is a choose-your-own adventure guide to the future of work.

How to Do a Handstand walks you through all of the steps necessary to go from novice to expert in 20 days.

Responsive Conference 2026

Responsive Conference is coming back in September! With AI and a changing economy, our jobs and careers are changing faster than most of us can adapt. Attend Responsive Conference and learn how to keep up with change.

Until next week,
Robin

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