The Leadership Masks We Wear: How Authentic Leadership Coaching Can Help Us Safely Reveal Ourselves
During my startup fundraising days, I wore what I now call the "Masculine Mask" — I cut my hair short, dressed like a dude, and put on the high-energy fist-pumping persona that investors expected.
Thirty pitches in with zero traction, I stood in the bathroom staring at a stranger in the mirror who was trying desperately to fit someone else's mold of success. Who was I?
By this point in the fundraising process, I was tired of pitching the same story, I had been rejected a whole bunch, and I felt like shit. I had followed everyone’s advice to the tee, why wasn’t it working?
It was the final pitch when I decided I didn't want to die with my mask on.
When the Foundry investors at the table asked what kind of company I wanted to build, I took off the mask and told them the raw truth: I wanted to build a love company.
That authenticity — that moment of showing my actual face — was what finally connected. They led our Series A shortly after. Looking back, this was one of my earliest experiences in what I now understand to be authentic leadership coaching principles at work.
Why We Mask Up
We wear masks for a reason. Think about it — when you're on stage, in front of people with their judgments, their love, their hate — it's natural to put up protection as a shield. Our primitive brains are wired to keep us safe from social rejection.
But here's the tricky part: this protection still needs to look good. So we seek external validation for what "good leadership" looks like. We emulate the Steve Jobs and Elon Musks of the world, thinking their masks will fit our faces.
I’m a half Chinese-half Jewish woman — Jobs’ mask was never going to fit my face, and there’s a good chance it doesn’t fit yours. Why? Because you aren’t Steve Jobs.
You are you, with your own family of origin, scripts of success, heartbreaks, and passions. There is no other mask built for you than your own face. Authentic leadership coaching helps leaders reconnect with this unique core.
The longer we wear masks, the more attached we become to them, even as they numb our insecurities. We stop using our emotions and intuitions that are hidden behind the mask. We default to what the mask would say it wants.
During my startup CEO phase, when people asked what I wanted, I said brightly, “To be a public company CEO!”
Holy hell, now I know what public company CEOs have to deal with and I cringe at what I thought I wanted. That job would not suit me.
Masks rob us of intimacy and connection — not just with our own desires but with others. People can’t properly see us and what we long for. Our breathing becomes labored, our expression constrained, but few people can tell.
And here's what's worse: others can sense when you're wearing a mask. There's a concept my coach calls "emotional wifi" where we're all plugged in together, picking up subtle cues from each other.
When you as a leader mask up, it signals to everyone else that it's not safe to be authentic. It’s why authentic leadership coaching often focuses on helping leaders model vulnerability to create safer, more connected workplaces.
The Leadership Mask Framework
I've noticed several common masks that leaders and entrepreneurs tend to wear. Do any of these sound familiar?
Know someone who resonates with wearing a mask? Please share with them!
How Masks Take Hold
The entrepreneurial masking journey typically unfolds in three distinct phases:
Phase 0: The Masks of Early Life
Most entrepreneurs I work with have had tough childhoods. Some were promoted to adults pretty early in life, and they got used to taking responsibility. They developed the Caring, Stoic, and Omniscient Masks quite young and out of deep necessity for their survival.
Phase 1: The Unmasked Beginning
Most entrepreneurs start their businesses from an authentic place. They're genuinely excited about their idea and the impact it could have. They're curious, open, and their enthusiasm is infectious precisely because it's real.
Phase 2: The Mask Adoption
As they start scaling, external expectations creep in. Investors want to see confidence. Recruits want to see stability. Clients need to believe you're experienced. So the masks come out.
Phase 3: The Stuck Mask
This is where things get dangerous. That mask you've been wearing becomes so familiar that it fuses to your skin. Even when you feel burnout or misalignment creeping in, you don't know where to begin unmasking. Here’s where authentic leadership coaching can be transformational, helping leaders distinguish their true selves from the personas they’ve been performing.
The Power of Removing Masks
I worked with a founder who wore the Positivity Mask religiously. She thought she was being motivational, but she was actually gaslighting her team.
When she finally dropped the mask and got real with her team, something remarkable happened. She earned their trust, brought them in to solve the company's hardest problems, and created genuine alignment.
This was a scary process for her, but working through those dark feelings — much like the work we do in authentic leadership coaching — brought her back to connection with her team and herself.
To be fair, she also lost a couple of team members who wanted the comforting lies. While that sucked in the short-term, it was also a blessing for her culture.
I experienced this unmasking myself during a particularly dire fundraising period. To my surprise, when I showed my fear, my team responded with loyalty and compassion. That authentic leadership moment shaped our company culture more than any strategic plan could have.
When Masks Are Useful
I'm not suggesting we burn all our masks in a ceremonial bonfire. The truth is more nuanced — sometimes masks serve a temporary purpose or help us grow into new capacities.
Authentic leadership coaching teaches that discernment is key: knowing when a mask is a helpful tool for growth versus when it becomes a harmful shield.
The Unmasking Process
Unmasking isn't an overnight process — it's a journey. Here's the process I guide my clients through:
Awareness
Name the mask
Identify the core emotions being covered
Create safety to experience those emotions
Practice authentic expression
Throughout this process, authentic leadership coaching plays a crucial role in creating the emotional safety needed to navigate these shifts.
Show Your Face, For Us All!
The tech industry has its share of popular masks, but beneath these personas is something far more powerful. Your unmasked leadership — your authentic leadership — has a power no mask can replicate.
Eventually, the goal is to lead fearlessly with your true face. And if you’re looking for support in that journey, authentic leadership coaching can be one of the most powerful investments you’ll ever make.
Because no mask, no matter how impressive, will ever be as powerful as your authentic self. The world needs the spice and variety that only you can bring.