How to Gain Confidence at Work Without Performing It

By Matteo Cassese. I coached executives and founders, consulted for unicorns like Netflix, and I still had to burn my own business down to learn this.

If I could give you unshakable confidence. Would you challenge your boss? Would you launch a new product? Would you change your career?

I’d love to hear what you would do if you had all the confidence in the world. We don’t dare to start our own businesses. Most advice says: project confidence. This talk pulls that apart.

Why “Fake It Till You Make It” Stops Working

It works, until it doesn’t. My business was struggling. I was trying to follow formulas for success. And I never knew the next month where the money would come from. I always came to the work with a sense of insecurity that my insecurity would make me good. Here’s what that belief actually did. If I doubt myself, I will strive and I will do a better job, and this is how I underserved my customers because I made the scope of work small. And it doesn’t stop there. Those who appear overconfident are just performing certainty while being equally disconnected. Real confidence isn’t swagger or certainty about the future, it’s the quiet knowledge that comes from listening to yourself. That’s what performing confidence actually was. At the time, I was on stage selling you something. And there’s nothing to sell. That’s the trade fake confidence makes.

The Confidence Paradox

Most probably you know this story already. The Emperor’s New Clothes. This is a story of overconfidence, but we don’t want overconfidence, actually we want the courage to be confident. Here’s the difference. The insecure is only worried about other people, what would they think of me. The overconfident is only worried about themselves. I’m thirsty, I want a beer, and everybody wants a beer, and so I’ve ordered beer for everyone. The confident is in fact vulnerable, tells other people how they are feeling. They have empathy for themselves and empathy for other people. Often times we see the overconfident as confident, instead the real confidence comes from vulnerability. That reversal is the whole point.

Confidence Is Downstream of Something Else

Here’s where that confidence actually comes from. You need to be extremely confident about who you are, about what you stand for, about your why. I have total confidence in the person, I have low confidence in the artifact. That calibration runs through everything. The only thing that changes is how much confidence I am putting into my presence. My life wasn’t built on confidence. My life was built on decisions. And looking at my decisions, I realized that I was confident. That’s not self-belief. That’s self-knowledge. It’s when you have the feeling that you are doing something that aligns with who you are. That’s what gut feeling means here. The expert doesn’t realize when they’re experting, because for them it’s as natural as breathing. It’s like the fish in water, you never see what you’re immersed in.

Four Things That Actually Move It

Test yourself before you read the list:

• In your last hard meeting, were you managing what they thought of you, or saying what you saw?
• Confidence in the artifact, not in yourself?
• Has more preparation ever actually removed the feeling?
• Do you know what you are unshakeably confident about?

Here’s what actually moves it.

Calibrate Your Confidence

I have total confidence in the person, I have low confidence in the artifact. Here’s how that plays out. I’m extremely confident in the energy that I’m using. I’m not so confident that this slide is actually working. I have a very low confidence how I’m saying what I’m saying. You should be confident in your team, but a little less confident. And you should be confident in the audience that you talk to, but not as confident as in you and your mission. When we talk about the product, the launch, the campaign, the artifact. Have low confidence.

Let Your Projects Fail, and Measure Them

Allow the products of your ingenuity to fail, allow yourself to learn from them. This is vulnerability, this is courage, this is the absence of overconfidence. Let your projects fail. Allow yourself to learn, allow yourself to measure.

Tune Down Distraction

Tune down distraction. I delete social media apps, I listen to fewer podcasts, I watch less videos, I spend more time by myself, I go on walks. If you do them regularly you will get into the Gap. In the Gap you’ll have access to your intuition.

Stop Asking Permission

Three years ago, I was speaking but I was asking for permission. Oh, will you trust me? Will you trust me to go on your stage? Oh, you are so kind. You have given me space. I am so grateful. And I’m not asking for permission right now. I’m done selling. I’m done convincing people. I’m here.

What Changes When You Stop Managing Perception

Here’s what that feels like from inside. Forget about being useful. Remember to be there, to be one, to be clear, to be accessible, to exist in front of your client. I’m done selling. I’m done convincing people. I’m here. It’s important who you are and how you show up, but it’s really not important what you say. Nothing has really changed. There’s still a degree of uncertainty where the next leads are going to come from. But there is a different person running this business. And I probably 10xed my prices in the process. There is a way of doing the shallow work, for lack of a better word, in a deep way. Just by showing up in a deep way, in a complete way, in a way where you can see everything. Just by doing the work at the terrace, on the terrace in the garden, rather than hiding in a cubicle in an office. That’s presence. That’s what changed.

Common Questions About Confidence at Work

Is it normal to feel unconfident at work even when you are good at your job?

The expert doesn’t realize when they’re experting, because for them it’s as natural as breathing. It’s like the fish in water, you never see what you’re immersed in. Unless you have the whole world queuing at the Wisdom Palace waiting to meet you, you’ll always stop yourself: that comes easy to me, I don’t believe that’s a big thing.

Does “fake it till you make it” actually work?

I always came to the work with a sense of insecurity that my insecurity would make me good. If I doubt myself, I will strive and I will do a better job, and this is how I underserved my customers because I made the scope of work small.

How do I look more confident in meetings?

It’s important who you are and how you show up, but it’s really not important what you say. Not tactics. Presence. The confident is in fact vulnerable, tells other people how they are feeling. They have empathy for themselves and empathy for other people.

What is the difference between confidence and overconfidence?

The insecure is only worried about other people, what would they think of me. The overconfident is only worried about themselves. I’m thirsty, I want a beer, and everybody wants a beer, and so I’ve ordered beer for everyone.

How long does it take to build confidence at work?

You will change over time, but you don’t change so quickly. The only thing that changes is how much confidence I am putting into my presence. Confidence is being able to make decisions based on your gut feeling. That’s the honest answer.

Can confidence be learned, or are some people just born with it?

All children are perfectly confident. The problems they have are caused by us, the adults, because we tell them they have to shut up, be quiet, sit down, and listen. That’s the moment where you start losing confidence. Society is also to blame.

See where your confidence is misplaced. Not where you think it’s missing. Take the free leverage assessment. No pitch. Just a clearer picture of where you stand.

Explore more

• Entrepreneur coaching: one to one for founders
• Executive presence: how you show up
• The leverage assessment

About Matteo Cassese

Business coach, keynote speaker, and mythmaker, Matteo helps leaders thrive in chaos and conflict. Twenty years across tech, film and consulting, seven of them at Warner Bros., founding-team at Netflix Italy, and advisory work for Sony, LinkedIn and Heineken. Berlin based. His unique perspective as a queer nerd passionate about mythology and technology creates a safe space for leaders to be vulnerable and reach their full potential. Read more about Matteo.