Be More Confident and Assertive at Work

Being too agreeable can limit your career – Issue #99

Most of us enjoy being liked by others. It’s human nature to want to belong and to be welcomed by the tribe.

Long ago, those who were not accepted were banished and often perished. So, it’s perhaps not surprising that we often strive to be agreeable.

However, this trait of agreeableness doesn’t do much for your career, and it may even hurt you personally. It’s challenging to get what you want in life if you’re not assertive.

For example, those who are too agreeable often earn less. People tend to treat you like a pushover, and then you end up frustrated and confused about your lack of progress.

I enjoy making people laugh. Probably too much.

In another life, I might have become a standup comic, like my friend Sarah Cooper. It probably stems from wanting to be liked. I know that I was too agreeable when I was younger.

I became less agreeable as I grew older. I wanted to achieve certain things in my life and career, and that meant that I had to take the bull by the horns and go after it. I also had to be more direct in my relationships, firmer with my requests, learn how to negotiate better, and know where my line was.

There are times that you can’t take “No” for an answer. If a situation isn’t working out for you — despite all attempts at negotiation — you must be ready to walk away. You have to move on to better opportunities.

So, how can you become more assertive? How can you truly improve your self-confidence vs. playing around with a few confidence hacks?

Here are some suggestions.


Boost your self-confidence

I talk with my leadership and career clients about writing the “Story of You.” I ask them to do this because we sometimes forget everything we have accomplished. We gloss over all of the great things we have achieved in our lives, big and small.

We’ve all been on a more fantastic journey than we realize. We’ve had life experiences that we have mostly forgotten or taken for granted. We’ve accomplished things that we no longer feel are worth mentioning.

Yes, there are always things you can do to develop your confidence further (e.g., improving your health and fitness, acquiring new skills, continually educating yourself). However, writing the Story of You will immediately elevate your confidence because it captures the decades of accomplishments and work you’ve already put in.

Find some time in a quiet place and start capturing your story from the beginning. Your holiday vacation away from work should help with this task.

It’s useful to talk with friends and loved ones who have known you since you were very young. They will remember achievements, strengths, and talents that you have forgotten or don’t notice.

This process will take some time. You can’t write the story of your decades-long life in one session.

But, get started and keep updating it over the next few weeks or months. Documenting your life is a surprising confidence builder.


Invest in your health

It is easy to underestimate the effect fitness can have on your sense of confidence. We all accept that being healthy and fit are essential, but I don’t think many of us connect that with how assertive we feel that we can be at work.

I let my health slide during the decades of my corporate career in Silicon Valley. One year I finally had enough and began a mission to recover my fitness, which is a little more challenging after 40.

However, it worked. I lost over 40 lbs, became even stronger and healthier than I’d been in my 20s, and I’ve maintained that lifestyle ever since.

I have more energy every day, feel better overall, look better, and it impacts how I carry myself. I wasn’t anticipating that I would start acting more assertive and confident in almost every situation. It was an unexpected benefit, but an invaluable one.

This isn’t just a personal observation with an N of 1. Research has found that physical activity can positively impact self-esteemreduce stressimprove brain functionincrease assertiveness (perhaps due to improved perception of body image), and more.

We know that exercise and eating healthy have numerous physiological benefits. However, it is also becoming more evident that you can boost your self-confidence and assertiveness with increased physical activity as well.


Banish your impostor syndrome

I wrote about how I overcame my Impostor Syndrome. I discarded the labels that the world had imposed on me and dug deep to identify my core truths. I set myself free from the layers of “camouflage and defense” that we tend to build up to protect ourselves from being hurt.

Face yourself head-on, look deep inside, and think long and hard about who you are.

  • Not who you wanted to be or thought you should be.

  • Not who you may have aspired to be, or even pretended to be.

  • Not the layers upon layers of your identity that you’ve developed since childhood.

Stop defining yourself by who you think you should be, or the expectations that others have placed on you. Stop letting yourself be judged by talents and skills that you secretly feel you don’t have. 

Instead, center yourself on the deep truths that have been core to who you are for as long as you can remember. Your truths will reveal themselves as consistent threads that keep cropping up in how you work, live, and interact with others. Center yourself on who you truly are.

The critical point is that someone else’s recognition or praise doesn’t generate the core truths about yourself. They can’t be taken away by someone else’s criticism, either. Failure doesn’t affect them.

Discard the labels and assessments being used to try to measure you by what you are not. You can’t be revealed as an impostor for something you no longer define yourself as being. It is incredibly liberating.

Once you identify your core truths, own them, and base your identity upon them, you can no longer experience impostor syndrome, and that enables you to be incredibly confident and assertive about what you want and deserve in life.


Be aware of how you speak

Many people use hedging phrases and unnecessary qualifiers in their communication, myself included. I think we naturally try to soften the request or demand.

We think that these phrases build rapport, when, in fact, they make us look uncertain and weak. I’m sure you are familiar with a few of these:

– “I think…”

– “I feel like…”

– “It would be great if…”

– “I should be able to…”

– “Basically…”

– “Honestly…”

– “Apparently…”

Plus, we tend to sprinkle our conversation with any number of verbal tics and vocal fillers such as:

– “Ummm…”

– “Like…”

– “Soooo…”

– “…you know?”

– “…right?”

You’ll have a better chance of identifying these issues if you speak more slowly and give yourself more time to think. We tend to babble when we are nervous, so slowing down is helpful regardless.

Make great use of silence when you want to pause and resist the urge to fill the gap with an “Ummmm.”

I know that it is hard to be fully aware of your speaking style and issues. You can record yourself speaking, and I highly encourage that you do this with video. That will allow you to simultaneously assess your verbal tics and fillers, as well as your body language, which I bring up in the next section.

You can also ask a trusted friend or loved one to give you feedback. Be prepared for this, and keep an open mind.

It’s not comfortable hearing about the speaking issues undermining your perceived confidence. However, identifying and overcoming them with practice will help you become more confident and assertive later.


Notice how you behave

So many people appear to lack self-confidence because they act uncertain and uncomfortable in conversational situations. Amy Cuddy’s research on body language talks about how the “power pose” can boost feelings of confidence.

While the validity and replicability of this research have been debated, there is no doubt that your body language does, in fact, impact how others perceive your confidence (and more).

This body language can include how you stand, your posture, where you place your hands, and how you move while you speak. However, it also includes something as simple as eye contact.

I’ve written about the power of eye contact before. In general, good eye contact may make you seem more confident, likable, attractive, trustworthy, attentive, and memorable.

Given this impact, it is a real shame that few people look each other in the eye during conversations. I think we’ve all noticed that trend. Eye contact should be made about 60–70% of the time during a discussion to create a sense of emotional connection, yet we are only doing it 30–60% of the time.

Knowing this, you can make an active effort to increase your eye contact with others while you’re speaking. Doing so will immediately improve your appearance — and feeling — of self-confidence and assertiveness.


Have clear goals in mind

What do you want? What do you really, really want?

Things aren’t going to end well if you go into a discussion or negotiation with a fuzzy outcome in mind. This is especially true if you’re an introvert.

Introverts don’t feel comfortable just winging it during a critical meeting. We need time to prepare and collect our thoughts, which helps us feel more confident during a discussion.

Create a specific and structured request for the outcome you desire. Nothing makes someone look less confident than not being able to answer, “What do you want?

I’ve been in entirely too many meetings with frustrated executives listening to rambling requests. Eventually, one would say something like, “Stop. Just stop. What in the hell are you asking me to do?

You should also be prepared with a clear and supported justification for your request. Research shows that simply adding a “because” statement to a request dramatically increases the likelihood that someone will grant your request.

Some examples from their findings:

  • Excuse me. I have five pages. May I use the xerox machine?” (60% compliance)

  • Excuse me. I have five pages. May I use the xerox machine, because I have to make copies?” (93% compliance)

  • Excuse me. I have five pages. May I use the xerox machine, because I’m in a rush?” (94% compliance)

This can be as easy as changing your request from “I need to take Friday off” to “I need to take Friday off because my mother will be in town.”

You don’t have to overdo it with your justification. You don’t need to create a long list of reasons.

Pick your top three that will have the most impact. Have others ready if you need to tap into them during the negotiation.

It also helps to visualize a positive outcome. See yourself being confident, assertive, and achieving your goals.

“Two reasons for visualizing are to recognize what you want when you see it and so you’re ready for the situation or result when it shows up.”


Know what you’re willing to concede

Create a list of what you absolutely require long before going into any discussion or negotiation.

This ties back into the precise goals you have in mind before the meeting. You want to know exactly what it is you are asking for before the conversation starts flowing.

Then, add items to the negotiation list to sweeten the deal for yourself. For example, you know that you want a 10% raise and will settle for nothing less. However, a 15% raise would certainly be nice and not out of the question. Start there with your negotiation, but keep in mind that you are willing to concede that extra 5%.

It helps to visualize two buckets for your requests.

One bucket is for your foundational request. These are the must-have items that you can’t concede.

The second bucket is for your nice-to-have items. These are the ones that you are willing to give up, if necessary.

If you don’t identify these two different buckets, it is too easy to get flustered and caught up in the heat of the debate. Lose focus, and you will lose ground on something critical for you. You have to know where you want to draw a line in the sand.


Establish where your line is

Yes, concessions are normal. But, you’d better have a line. When you don’t, you walk away disappointed every time.

The more aggressive individual will push you back past that line. It’s the nature of debate and negotiation. The more confident and assertive person will keep pushing for the biggest win.

Some say that you should never have a “walk away” point, but I disagree.

For example, I’ve found that my career advanced the most when I knew my line during promotion discussions and offer negotiations. I knew what was acceptable for my next move (e.g., role, title, compensation) and what fell beneath the line.

It would have been easy to become flustered when someone offered a much larger signing bonus for a role that wasn’t the level that I wanted for my next move. Who doesn’t like more money?

However, I had already established my walk-away point when I was feeling very calm, rational, and planning out my future career path. That made it more of an objective, quantitative decision.

My hard line is X on this must-have item. They refuse to offer more than X-1. Therefore I say, “Thank you for the offer, but I know that I should have X, and I have clearly justified X. I’m going to decline and accept an offer from company ABC who is offering me X+1.


Face your worst fears

Identify the worst-case scenario.

What happens when you are confident, push back, and you don’t get what you want? What happens if you’re assertive and it blows up in your face?

Those fears are what has held you back in the past. Those fears have eroded your confidence and kept you from being more assertive. Identify them, face them, and create your contingency plan.

If I do x, they do y, and z happens, then I’m going to do this, and it will be ok.

I always have a backup plan to respond to a potential failure. It reduces the initial shock if and when failure does occur (e.g., I anticipated this might happen). Plus, it helps you fall back to your Plan B and quickly recover.

Another powerful exercise is to face down your worst fears that may or may not have anything to do with your professional life. 

Conquering a fear of public speaking will help you both professionally and personally, of course. However, overcoming a fear of heights by taking a skydiving lesson may not have much to do with your professional life.

Yet, conquering any fear and becoming stronger — no matter what it is — will contribute to your overall sense of empowerment and self-confidence. 

Being assertive in a meeting will seem like nothing after you’ve jumped out of an airplane and survived. In fact, many of the things that seemed so overwhelming and stressful before may now seem like trivial issues.


Enjoy your new level of confidence

I must admit that I’m sometimes surprised by the level of confidence I feel at this point in my life. Maybe it’s partly due to growing older.

Maybe it’s also partly due to my improved physical health and strength. And, perhaps it has something to do with tapping out of my old career path and creating my own business.

However, more than anything, I know that it is because I have accepted who I am and who I will never, ever be. I’ve made peace with that.

I’ve stopped feeling like an impostor. I know what I’m good at doing — really good at doing — and I focus my energy there. 

I’ve stopped trying to be anything that I am not. I’m also brutally honest about what I’m not good at doing.

Once you have identified your core truths and strengths, you can claim them and own them. You deserve to feel confident about them.

Knowing that, and using the techniques I’ve discussed here, you can move forward with becoming more assertive about what you want and deserve both professionally and personally in life.


Reminder: I have a private Facebook group for my premium subscribers. If you’re not already part of my Slack community, the group is an excellent place to have more in-depth discussions on newsletter topics, ask and answer more questions, and also for me to get guidance from you about how to continue improving the newsletter for you. Join if you’d like to participate.


Quick Tip

I have an amazingly simple and effective tip for you that will immediately increase your confidence and assertiveness at work:

Stand up in meetings when you can.

This won’t be appropriate for every single meeting. However, you can take advantage of this tip when you are presenting, want to take control of a meeting, or have the opportunity to speak at length.

Stand up to speak to the room. Walk around a little. Make eye contact with people as you are talking.

Go to the whiteboard and use simple diagrams and sketches to ask questions, make a point, or clarify an issue. The person who controls the whiteboard controls the meeting.

All eyes will focus on you. They will immediately see you as more assertive, confident, and perhaps even dominant.

For example, I was once in a meeting when a grumpy executive was trying to derail my presentation. He was dismissive and combative.

I walked from the front of the room to where he was sitting. I silently stood over him as he was speaking. He visibly leaned back and moved his seat a little, somewhat surprised by my presence.

However, it changed the dynamics of the conversation. He stopped being so aggressive and let me finish what I was saying.

Look for an opportunity to stand up and talk in one of your next meetings. Take note of how you feel (e.g., your confidence level) and how the people in the meeting respond to you.


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