How do you become assertive/confident?

What is the/your trick to be the person in the office who is assertive/confident and nonchalant when speaking with the CEO of a real estate development shop? How do you speak to him, ask questions in a manner which you aren't intimidated by him/her?

I see people in the office who have a friendly relationship with the partners, MD, CEO like they just crush it. I don't want to be seen as the reserved, quiet person who doesn't speak out enough and ask questions especially if the founder is chill. Thoughts?

 
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The first and most important thing is not to try and be someone that you're not. Anyone who spends more than a day working with you will see straight through it, and it's going to make your day to day miserable to constantly try and pretend.

Generally in life we think that others think way more about us than they really do. Do your thing. Do your homework and learn as much as you can about your product type, market, role, etc. Be a voracious reader. Grab drinks/coffee/lunch with coworkers and peers in the industry as much as possible, with the goal of asking questions and learning as much as possible rather than trying to be impressive. You'll never be the smartest person in the room and, if you are, go to a different room.

Nobody's expecting you to be some gunslinger that's nonstop wheeling and dealing. Just do you.

 
Dry Dropper:
The first and most important thing is not to try and be someone that you're not.
This. Be yourself. Don't compare yourself to other people. Go all in on your strengths.

CRE point about knowledge and relationships is very good also.

I would add that the importance of taking care of yourself outside of the office cannot be overstated. Work out every day. Be social. Learn. Meditate if that works for you. Doing shit every day to improve on a personal level will help you develop natural confidence which will keep you in the best possible mindset to grow professionally. Your confidence will grow organically over time and you will maximize your chances of capitalizing when opportunities present themselves.

 
Dry Dropper:
Do your homework and learn as much as you can about your product type, market, role, etc. Be a voracious reader. Grab drinks/coffee/lunch with coworkers and peers in the industry as much as possible, with the goal of asking questions and learning as much as possible rather than trying to be impressive.

This is great advice. Nothing is more annoying than someone who tries to be impressive. It comes off as disingenuous to your superiors and your peers will loathe you. If you are passionate about learning and enjoy what you're doing that will naturally shine through and people will be able to detect that. All the fake posturing and validating is just insecurity. Confidence is being able to have a normal conversation about someones weekend, asking thoughtful questions about a deal, knowing the basics when your name is called in a meeting, etc.

 

To be honest, I struggled with this a lot when I was younger. Now, my friends and coworkers often say that confidence is one of my strengths. What changed? 2 things. First, know your shit. If you know, and I mean KNOW what you’re talking about, then you get less nervous. Second, once you realize that no matter how senior, everyone is just a person who’s trying to learn or hear what you have to say. Fake it till you make it. You don’t have to “be” confident to project confidence. Once you start to fake the confidence, it begins to manifest in other parts of your personal life as well. After a little, you just become naturally confident. Own it. Internalize that you deserve to be there. Imposter syndrome happens to everyone. You got hired for a reason, now go and show them that reason!

 

Honestly, I don't think there's anything wrong with being quiet and reserved, that's also a positive force and perfectly admirable. Trying to show off or insert yourself awkwardly is far worse. It doesn't sound like you're the odd genius staring at the floor! If you seem engaged and interested, and are trying hard & performing well, people in time will engage you. Having a warm, open smile and making eye contact is sufficient, being a positive presence. Don't force it and just allow things to progress in time, naturally and with sincerity. As said above, just be yourself. It's always safe as an icebreaker to ask a Sr. person about their kids, what sports, where in school, etc - everyone loves to speak about their fam.

 

This. The most impressive guy I've worked with in my career rarely spoke during investment committee. But he knew his stuff, and when he felt that he actually had something to add he spoke and everybody in the room listened. He could change the tone of a deal discussion with a single sentence. Not even our CEO had that ability.

 

I would say I naturally am someone like the OP and improved. I’m still not a talker for the sake of it, but in my sphere of influence, I know my shit. I have a good memory when it comes to numbers, so I can rattle out stats and important deal points easily in the heat of the moment (work on that). Also, fix your head set and phone so your voice sounds louder to others on conference calls (tip for you) if you are naturally soft spoken.

I’ve also worked in the chummy world of a big office. At some point, you might realize that you like working in smaller teams where your worth is really just your performance and how you get along with people (not trying to be the golden boy). In a bigger office/organization (I use the term bigger loosely because some companies have that culture of Hunger Games - big or small), people tend to hide their cards and there are more games. It’s necessary to play the game there for longevity.

Just be you. Don’t be afraid of your boss. It’s hard sometimes they are either hard to read or have a reputation of being sort of mean; but they sense fear, and don’t be fearful or else it will be self fulfilling. Get your good experience. Build your relationships by being in the “fire of battle” or in the trenches. You’ll earn the most respect that way, by being dependable and competent. Ultimately, you’ll know what environment you like and would thrive in.

Have compassion as well as ambition and you’ll go far in life. Check out my blog at MemoryVideo.com

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