Imposter Syndrome
IT'S NOT A FLAW. IT'S A FLAG.
It’s a sign that your highest-potential people are stepping up, innovating, and leading in ways they’ve never had to before – the gateway to fearless leadership.
What are you going to do about it?
Whether you’re leading a team of one, your family, a department, or a Fortune 500 company, fearless leaders change the world. But becoming fearless isn’t about averting fear. It’s about embracing play and curiosity, and building R.E.A.L. Confidence™.
An estimated 75% of executive women report experiencing imposter syndrome.
But what if it’s not something to overcome—but rather something to embrace?
Imposter syndrome shows up at the edge of growth.
When people are:
- Stepping into roles they’ve never held before
- Leading in industries or environments where they’re underrepresented
- Navigating uncertainty, innovation, or cultural headwinds
- Doing things that have never been done before
In other words: Exactly the kind of work you want them doing.
"I’m planning to listen to this recording again and dive into the exercises even further. For me, this was definitely one of the most beneficial workshops that has been offered!"
So how do people make this shift from fearing
imposter syndrome to embracing it?
They build R.E.A.L Confidence™.
Over the last decade, I have worked 1:1 with hundreds of women. I have spoken to thousands. And do you know the number one thing they all struggle with?
Confidence.
It doesn’t matter how many people they manage. It doesn’t matter what credentials they have. It doesn’t matter what trophies are on their bookshelves.
Confidence is the number one challenge for most of the women I’ve spoken with struggle with.
And the truth is, in many cases, the more accomplished an individual, the more likely they are to experience feelings of being an imposter.
Studies show that high achievers are most likely to experience imposter syndrome. Actually, 70% of all people (yes, ALL people) have experienced imposter syndrome at some point. We just know that women are more vocal about it. 75% of executive women have expressed experiencing this at one point or another.
Why most trainings miss the mark…
You see, many workshops, keynotes, and trainings focus on “fixing the person” and “solving the problem.” But isn’t that a bit contradictory to embracing each individual? And aren’t we looking for a transformation, not a bandaid solution?
I thought so.
One of the greatest compliments I’ve ever received? A mentor once called me fearless.
But fearless doesn’t mean without fear. It means acting anyway—especially when you’re not ready. That’s what this work builds: a strong sense of self and a deep self-trust that powers courageous, value-aligned, fearless leadership.
Confidence isn’t built through theory—it’s built through practice. R.E.A.L. Confidence™ combines play, psychology, and identity-level transformation to create lasting results.
What is R.E.A.L. Confidence™?
One of the most transformational experiences of my life were my years immersed in Chicago’s improv scene where I learned to take action without knowing what was going to happen next. That’s why we intentionally integrate play and improv into the work we do in this program to tap into the kinesthetic elements of activating our brains and our bodies. I spent years entrenched in every improv theatre Chicago has to offer from iO to The Second City to The Annoyance and everything in between.
The R.E.A.L. Confidence™ Experience blends behavioral science and playful improvisation to help women step into fearless leadership.
This work is:
- Rooted in psychological research
- Backed by proven tools and frameworks
- Energized by improvisation and play
- Grounded in identity-level transformation
- Designed to move people from insight to action
Participants learn how to:
- Reconnect to themselves and define success on their own terms
- Establish unshakable self-trust using behavioral and mindset tools
- Act despite uncertainty using improv-inspired action-taking
- Lead for aligned impact—with clarity, confidence, and compassion
Wanna shake things up and build R.E.A.L. Confidence™?
CHOOSE YOUR OWN ADVENTURE
The R.E.A.L. Confidence™ Paradox: Why Imposter Syndrome is the Gateway to Fearless Leadership
90-Minute Workshop | Onsite or Virtual
This interactive workshop invites high-potential women to reframe imposter syndrome—not as a flaw, but as a flag, a signal they’re on the right path. Through the lens of improv, psychology, and personal leadership, they’ll learn how to start leading with fearlessness.
- Includes R.E.A.L. Confidence™ Reboot Guide
- Ideal for ERGs, women’s summits/conferences, team off-sites
- Workshop follow-up typically includes company or association-specific 6-week cohorts
The R.E.A.L. Confidence™ Cohort
6-Week Virtual
The cohort takes the workshop deeper—embedding the learning into real-world leadership.
Designed to help women leaders take action before they feel ready, this experience blends improv exercises, behavioral coaching, and identity work to create internal transformation.
Participants will:
- Build confidence through practice, not just pep talks
- Clarify what fearless leadership looks like—for them
- Reframe fear as a compass, not a constraint
- Strengthen self-trust and psychological safety
- Use improv exercises to turn doubt into decisions
- Practice leading from their core values, not credentials
- Join a supportive, honest, growth-minded cohort
Two formats available:
- Corporate or Association specific cohorts (recommended post-workshop)
- Entrepreneur Cohorts (stay tuned for announcements)
Exclusive Executive Roundtables
90-Minute Virtual Roundtable Discussion
For HR, DEI, L&D, and Talent Development Leaders
Before booking the talk or cohort, many companies opt into an exclusive, 90-minute virtual roundtable to:
- Explore how imposter syndrome manifests across your organization
- Understand the R.E.A.L. Confidence™ framework
- Connect with peer leaders facing similar challenges
These invite-only sessions often catalyze larger organizational conversations around retention, leadership development, and inclusive culture building.
The R.E.A.L. Room (Coming Soon)
Virtual Community & Continued Support
Want to keep exploring fearless leadership and building R.E.A.L Confidence and connections?
Join a monthly curated community of women leaders to:
- Deepen the R.E.A.L. Confidence™ framework
- Learn from guest speakers
- Participate in guided reflection and breakout discussions
- Network and build connections across industries
- Practice courageous conversations and risk-taking in a safe space
About the Creator
Kiley Peters is a strategist, international speaker, and serial entrepreneur who has spent over a decade building businesses, mentoring women, and learning—over and over—that confidence doesn’t come before action. It comes from it.
With years of improv experience at world-renowned theaters like Second City, iO, and The Annoyance, Kiley brings sharp insight, honest storytelling, and deep empathy to every stage she steps on.
She created R.E.A.L. Confidence™ to give other women what she spent years building: the tools to lead with conviction—even when the path is unclear. And she has traveled this path numerous times as a creative, entrepreneur, CEO, and a woman forging paths where there were none before.
Fearless leadership isn’t about eliminating fear.
It’s about embracing play, exploration, and self-trust to lead fearlessly.
WHAT NOW?
