Overcoming the Shame Spiral to Unlock Growth with Sayle Hutchison
Sayle Hutchison, 15Five’s CFO, is a respected software industry leader. Throughout her career, she’s overseen four different major acquisitions. But, to succeed in an executive leadership position, she had to undergo a process of personal growth and transformation.
On 15Five’s HR Superstars Podcast, Hutchison talked about how she overcame negative self-talk and shame, developed confidence as a female leader in tech, and created a life that felt truly worth living.
Here are some key nuggets of wisdom she shared.
An uncommon upbringing
Hutchison always possessed a strong sense of self. “I always say that your life is this perfect balance between what you can tolerate and what you think you deserve,” she says. “That sense of what I thought I deserved had a high bar for how I expected people to treat me, how I moved in the world.”
Hutchison credits her self-assurance to her unique background. First, she lived for eight years in Saudi Arabia—witnessing firsthand the effects of a restrictive society. Later, she moved to Atlanta, where she had to reconcile the presence of gender inequality in the South with the oppression of Saudi women. “It was really clear about the respective value of the personhood between men and women. And while I can recognize that it was a progression, a clear progression from the Saudi Arabian female experience, it still wasn’t… something I was interested in terms of a model of equality.”
When Hutchison moved to San Francisco, her worldview shifted again. “You had a diaspora of people who had been kicked out of their homes for who they were. [They were] really reclaiming a sense of value and understanding how to achieve self-love even in the face of all this societal pressure,” she notes. The idea of being self-confident in the face of negativity was inspiring.
The path to leadership
Hutchison’s background allowed her to think critically about gender, race, sexual orientation, and how she viewed herself in the world. “It was extremely enlightening for me to see those three snippets of time and those three views of equality as I entered the workplace… Those experiences allowed me to have a view of myself that commanded and demanded equality.”
But Hutchison’s self-belief was not always resolute. She describes a period of deep unhappiness after turning 39. “I didn’t have the patterns of self-help and self-care. I was falling into that traditional trap of a role-based life. So I’m a mother, I’m an employee, and I didn’t have a real personal life… I had to really stop and say, ‘Is this the way you want to spend your life?’”
After reflection and dialectical behavioral therapy (DBT), Hutchison clarified her intentions. “I am the only one responsible,” she remembers thinking. “Irrespective of patriarchy or discrimination, this is a life I am creating for myself… Coincidentally, that’s when my leadership journey began.”
The Defeat Triangle: How women hold themselves back
After managing employees for over 25 years—and reflecting on her journey from financial analyst to CFO—Hutchison has developed what she calls the “Defeat Triangle” to describe how women hinder their professional development.
The first piece of the triangle is the self-defeating inner critic. This voice in your head doubts your abilities. “If you’ve got challenges with your self-worth, this can be a super negative dialogue. It can be a real detriment to your career aspirations and personal happiness in life,” she says. “So, how do you talk to yourself?”
The second is shame. Shame goes beyond the recognition of making a mistake. Hutchison describes it as “violating social norms and then feeling bad about it. And not just feeling bad about what you did, but the end of that conversation is ‘I’m worthless’ or ‘I’m not good enough.’”
The final side of the triangle is perfectionism. Hutchison refers to this concept as a “high bar,” or the feeling that nothing you do will be good enough. “You’re exhausting yourself before you even [begin],” she warns.
For Hutchison, these internal struggles create a spiral of shame—undermining your ability to enjoy life, learn, and embrace your work. In this loop, employees lack the energy to be their best selves or lead others. “You can’t be a leader of other people if your entire dialogue is negative,” she says.
How to overcome the shame spiral
Hutchison argues that anyone who wants to become a leader must confront their internal struggles around identity, worth, and shame.
“When I think about how you really get to the senior level or to the leadership level, it requires so much self-energy and so much self-belief that every person has to go through this journey,” she says. Here, she outlines several strategies for developing personal confidence.
1. Understand your inner dialogue
For Hutchison, the first step is to list your inner thoughts and separate them by shame and accountability. This process will disrupt the “shame spiral” and allow you to focus on areas of improvement. “The shame is so obvious,” she says. “It’s all about ‘I am’ statements and something negative as opposed to ‘I did something. There’s something I need to learn from.’”
Thinking of her daughter helped her process her thoughts. “Would I be proud if Zoe [spoke] to herself this way?” she asks. “Would I think it was actually a helpful dialogue, or is this just self-abuse? You have to unblend those two.”
2. Claim your strengths
The second step is listing your strengths. For Hutchison, knowing your strengths acts as a pillar for self-confidence. “You can’t grow if you don’t have a stable place to operate from,” she says. “So I call it claiming your strengths. Do you know what you’re good at? Are you comfortable with that?”
3. Identify areas for growth
Next, identify the areas where you need to improve. Hutchison stresses the importance of doing this guilt-free. “How do you need to focus your attention and energy to grow your craft?” she asks. Is that an active conversation you can have without beating the crap out of yourself and going into a shame spiral?”
Hutchison recommends leaning on people you trust for support. “I also had a group of incredible women around me who I could speak these lists out loud to and who I could trust to give me honest feedback,” she recalls. Whether it’s a manager, mentor, peer, or friend, leaning on others for constructive feedback is critical.
4. Take accountability
Finally, learning how to take accountability is essential. Hutchison refers to her internal dialogue as her “hall of accountability.” Here, she reflects on what went wrong and how to avoid repeating the same mistakes.
“Then I forgive myself and move on,” she says. “It’s really a sacred part of my practice, and it allows me to stay resilient. I can be the person that can own when I’m wrong. [I] can be wrong without that being an emotional experience for everyone else.”
“Confidence is a personal journey.”
Hutchison emphasizes that personal growth does not happen overnight. She advises to start small, reframing your inner dialogue one thought at a time. “I’m here to tell you, if I can do it, anybody can do it. It’s 100% overcomeable,” she adds. “It’s not easy, but making a personal commitment to moving through this experience is a gift you’ll always be grateful for.”
Listen to the full HR Superstars podcast episode to discover how Hutchison’s journey towards self-confidence empowered her to excel as an executive.