Becoming More Assertive: Why It's Worth the Work

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The importance of becoming more assertive can not be stressed too much if you have goals of improving your personal relationships or your work environment. Or both. This is true for you and your partner, your children, your in-laws and parents. For your friends and acquaintances. It’s helpful with your boss and it’s helpful with people who report to you. Clients, peers. 

Assertiveness is a win-win if I’ve ever seen one and this post is going to show you why becoming more assertive is worth the work.

Assertiveness vs. Everything Else

Assertiveness means different things to different people.

If you’re kind of a shy guy who regularly tells others that plans are up to them, and that you’re ok with anything they decide, you’ll view assertiveness very differently than if you’re the kind of person who has strong feelings about how a project should be run.

Maybe you’re the type of person who feels that others rarely listen to you. It’s more than a little frustrating that you watch people make avoidable mistakes over and over again. You don’t think it’s even worth the energy to explain your idea. They’re going to shoot it down anyway. Ok, maybe they’re right. Maybe your idea isn’t so great. You spare yourself embarrassment by not putting that idea out there or get taken advantage of

Or you’re the guy who, unless you’re loud and forceful, no one seems to pay attention. If you’re in charge, you get angry pretty damn quickly when other people are questioning your authority. Better to just make demands and let them figure it out. You’re certain you have the best solution anyway. What’s to be gained by listening to everyone else discuss ideas when they are just going to come around to yours by next week? You’re the boss, right? You tell them what to do. 

Assertiveness is the perfect blend of taking care of yourself while, at the same time, taking other people’s feelings and needs into consideration. Becoming more assertive not an easy thing to do and it’s possible to get lost in 1) taking care of yourself at the expense of others, or 2) taking care of others at your expense.

The Role of Confidence in Becoming More Assertive

Confidence is often a part of assertiveness (but not always.)

It’s hard to be definitive and direct about what you want if you’re not sold that you deserve it. Confidence is often what has done that sale.

Aggressiveness can be a mask when confidence is lacking. If one of the outcomes of aggression is to intimidate, stop people from questioning you, stop having to make a case for why you should have something or should do something, aggression can get the job done without becoming more assertive. If you’ve scared and intimidated someone you’ve usually stopped them from challenging what you say.

Confidence isn’t always lacking in aggression, but the over-confidence we often see in the aggressive person can be compensating for the lack of it. Just look to anyone who leads by fear instead of by respect. Keep people afraid and there won’t be space for disagreement.

Does your boss keep a lot of people around who always say “yes” to him or her? Do the bosses you know seem to grow from being challenged by what someone who reports to them says? It’s a very different atmosphere if you’ve worked in an environment when the person in charge really takes in what others bring to the table.

Managing & Parenting: Similar Styles

Some of us have never had the experience of a boss who really values our input. Often people don’t even question this. These work environments certainly aren’t encouraging of people becoming more assertive. You’re supposed to hate your boss. You’re supposed to begrudge what he or she says. It’s normal. Isn’t everyone at the bar complaining about the same thing?

We can see why we’re so used to some of those other methods of leadership when we go back to those original supervisors: our parents.

There are three types of parenting styles that are often talked about:

  1. Authoritarian,
  2. Authoritative, and
  3. Permissive.

The permissive style is seen in those parents who are uncomfortable with being the authority and setting limits–they give in to their child and the child doesn’t get to learn how to sit with difficult feelings or what it’s like to have someone say “no”–and follow through with that “no.”

The authoritarian parent is the dictator. No questions asked, it’s my house, just do what I say. If not, there is often a strong, scary punishment to follow. Sometimes this is even given for rules that weren’t yet established. The authoritarian parent’s prerogative is that the children not only must listen to him or her, but they need to instinctively know or infer what that parent wants them to do at all times. Or else. 

The authoritative* parent is the one who provides rules that make sense. They’ll explain the reason for them–up to a point–and sets consequences if they are not followed. This style of parenting can hold someone accountable, but also listens to and accepts the feelings which may have led to the rule breaking. You’re never the “bad kid” with this kind of parent, although you may do unacceptable things that have consequences. Suffice it to say, no one parent is always the authoritative one who does everything perfectly so call off the shaming police if you’ve said “Because it’s my house, that’s why” at one time. If it’s your weekly go-to because of frustration, let’s talk.

Authoritative parents may be more confident, but that doesn’t mean they don’t doubt themselves. They overthink sometimes, they second guess and Monday morning quarterback their own decisions–but they are still going to make decisions with the information they have. They’re going to change things if need be. They’re going to say they’re sorry, they’re going to say they’re wrong, they’re going to say, “This sucks, but this is what we’re doing because it’s the best course of action right now.”

They’re assertive.

Getting Rid of Resentment

Spend some time considering what you’re parents’ parenting style was. Maybe they had different ones that complemented each other. Maybe one enabled the other. 

How might their style of interacting with others have influenced you? You not only experienced that interaction with them, but you watched them interact with each other, or with your siblings. Even if you’re an only child raised by a single parent, you observed how he or she interacted with peers and with your friends. And permissive and authoritarian parents are not the best models for becoming more assertive. 

Do you see any common dynamics with how their parenting style has filtered into your interactions with colleagues, friends, partners, and your kids?

If you’ve been having trouble being assertive you may feel you fall into one of two categories: the aggressive person or the  passive person. You may think those two character traits are at opposite ends of a spectrum, but they have one thing in common, at least, and that is resentment. Those who are aggressive are usually more in touch with this than those who are passive, but if you dig deep, that resentment is there.

And it comes out, whether slowly seeping (passive-aggressiveness, sarcasm, perhaps even in depressive symptoms) or violently exploding.

You’re Not a Kid Anymore, Kiddo!

The fact that your voice didn’t matter when you were growing up does not mean it doesn’t matter now that you’re an adult. Have you surrounded yourself with people who still don’t value your opinion or people who try to walk right over you when you talk? Do you still feel you need to fight to get heard or that you need to “go along to get along”?

If the people in your life are worth your time and if they respect you, then they probably want to hear more from you.

So this post isn’t How to Be Assertive. Look for that in the posts to come. This is the Why Be Assertive and why it’s healthier than aggressiveness.

By becoming more assertive you can stop being resentful and you can start having better relationships.

I told you it’d be worth it.


If you’d like to talk more about becoming more assertive, or about anything you’re struggling with, please don’t hesitate to send me an email or give me a call.

*I know, the spelling is similar. I often confuse these two, which is unfortunate. Let me know if you come up with a better term.

Justin Lioi, LCSW is a men’s mental health and relationship expert based in Brooklyn, NY (and online throughout New York State and internationally.) He received his degree from New York University and has been working with men and their families for over 10 years. Justin is on the Board of the National Association of Social Workers and writes a weekly column for the Good Men Project called Unmasking Masculinity. He can be found on local and national podcasts talking about assertiveness, anger, self-compassion, all with the goal of becoming the man you want to be. He works with all men but has a particular focus on providing counseling for fathers (and guys hoping to become dads!)