How to Be More Assertive When You Have a Controlling Boss


Controlling boss


Profile Picture
June 12, 2024 at 7:42PM UTC
Assertiveness is something we're taught about from the time we're kids — we're taught that assertiveness means being bossy. When you were growing up, if you were like most little kids, you were probably very clear about what you wanted and not shy about asking for it. “Hey everybody, we’re going to climb that hill over there. Now. Come on, let’s do it!” And off you ran with the other kids mumbling under their breath about how bossy you were.
The next time, one of them said it out loud, telling you, “You’re so bossy! I don't want to do that!” And, unfortunately, if you were often bossy, it’s likely that the teacher heard about it, too, and may have even mentioned it to your parents who then scolded you at home. 
And so, you are silenced. 
Let’s say you made it through the tweens unscathed. Another hurdle was the teenage years. You become so concerned that your friends won’t like you anymore that even the slightest hint that you are too bossy makes you change your behavior, tone of voice, eye contact, body language and overall communication style. You try to fit in and not hurt other people's feelings. 
Are your parents/friends/teachers/other people trying to silence you? No! It’s just that criticism doesn’t always go hand in hand with explanations about how you can more effectively lead. Why? They don't always know how, so they can’t tell you how.  
We end up silenced adults, unsure about how to voice our opinions without coming across as… you guessed it, bossy. One of those "assertive people" in life with too much confidence.
Enter your boss, a controlling type. She’s sometimes called bossy, too, but she wasn’t silenced. She’s very clear about what she wants and spends all day telling you what to do. 
A passive person who works for a controlling person faces a special kind of misery. So how can you be more assertive with this other person in your workplace situation? 
1. Be clear about what you want.
Start by being clear in your own mind about what you want. 
Let’s say your boss wants to review your emails before you send them to clients. 
You go home every night and complain that your boss is so controlling! 
Think about what you actually want in this situation. Do you want to be able to send emails without having her review them? 
Be sure that what you want is actionable. That is, it must be something that your boss can do. Saying, “I want you to stop being controlling” is too vague. But saying, “I’d like to be able to send these emails without you having to review them” is clear. 
Once you’re clear about what you want, think about what they want. 
2. Understand their "why."
Why is your boss asking to review your emails? Don’t just guess, because most of the time your guess will be wrong.  
The only way you can know for sure is to ask her. 
Start with, “I’m curious…” which helps you come across as actually curious rather than defensive. Compare, “I’m curious…why do you want to read my emails to clients before I send them?” versus, “Why do you want to read my emails to clients before I send them?”
3. Listen to the reasons.
Once you ask “why”, you’ll start to understand the deeper reasons behind a controlling person’s behavior.
Sometimes the answers will be related to a bad experience she had, “My last assistant sent emails full of grammar mistakes to our clients and it was so embarrassing.”
Is very different from, “I want to be sure you’re saying the right thing.” 
Which is different from, “I almost got fired last year when my assistant sent the wrong price quote to a client.” 
Now that you know what the issue is, you can come up with solutions! 
4. Ask what it would take.
Start brainstorming solutions to controlling behaviors. Your script might sound like this, “I understand that you’re afraid I’ll say the wrong thing. I’d like to be able to send these emails without you reading them. What would it take for me to show you that I can do this?”  
Or, “What would it take for you to feel confident that I’m ready?” 
Asking for the other person to think through what it would take for you to take control will help them feel like they have control over the process of letting go. 
And voila, you’ve asserted yourself without being bossy or aggressive! 
Three tips to being more assertive...
1. Stop using softeners.
When you live in a world where being likable is as important as being competent, you’re walking on a high wire that at times feels impossible to steady. “Don’t say this” or “Say it that way” becomes overwhelming! 
Removing some common softeners will help you come across as more confident and assertive. 
Some of the softeners most commonly used are words like, “just” as in, “I just need a few minutes of your time,” or “I’m just checking in on that project.” 
What to say instead: “I’d like ten minutes of your time” or “I’d like an update on that project.” 
“A little bit” as in, “Can I get a little bit of feedback?” or “I’d like a little bit of your time next week” or “I’d like to present a little bit of data in the meeting today.” 
What to say instead: “I’d like your feedback” or “I’d like to get half an hour on your calendar next week” or “I’d like to present the top three points of data in the meeting today.”  
“I’m sorry” when used for anything other than an actual apology, as in, “I’m sorry, can I get a few minutes on your calendar today?” or “I’m sorry, I have an idea” or “I’m sorry, I was in the middle of a sentence when you interrupted me.” 
What to say instead: Just remove the “I’m sorry” part and you’re good to go!
2. Don't take no personally.
When you have a controlling boss, you will likely have to ask multiple times to get what you want. Part of asserting yourself is understanding that it’s usually not about you. 
When you get a “no”, rather than assuming the worst, ask why. 
Rather than going to the dark side and assuming you did something wrong, use the same skill you learned in section 1 and ask, “I’m curious... why…” 
Let’s say you asked your controlling boss if you can have the authority to sign for deliveries. She says, “No.” Instead of spiraling into self-doubt, knowing that of you hadn’t spilledt coffee on that client report last week, she’d trust you to do this… ask! 
“I’m curious, why won’t you let me sign for deliveries?” 
Listen to her response. 
3. Be resilient and ask again.
After you’ve found out the real reason behind a “no,” use, “What would it take…” to get agreement on next steps. 
In our example above, your next step is to ask, “What would it take for mebe to show you that I can do this?”  
Get specific action steps to prove you’re ready to be trusted.  
Don't give up! It may take you many times to start using these tips and scripts in a confident way. New behaviors take practice for you to feel comfortable and for them to work.  
Nothing works 100 percent of the time in life, but even if these tips and scripts on how to be more assertive with your communication style, tone of voice, body language and eye contact only work some of the time, you’ll find yourself feeling more confident and become a more assertive person in the end. And, yes, you can even become an assertive person with a controlling boss!
What tips do you have for people looking to work on their assertive communication and assertive behavior?
Melissa Hereford is a negotiation expert who will teach you to respond clearly, calmly, and effectively so you can get more of what you want, all while building stronger relationships. Get your free negotiation script at 

Why women love us:

  • Daily articles on career topics
  • Jobs at companies dedicated to hiring more women
  • Advice and support from an authentic community
  • Events that help you level up in your career
  • Free membership, always