The Toast Summit in Toronto. Photo by Ryan Francoz for
Nobody wants to sit in discomfort at work. The instinct often pulls people toward silence, blending in, and staying out of risk. In tech workplaces, many women find that discomfort shows up anyway, woven into daily decisions and career moments. Learning how to lead through those moments has become one of the hardest tests of leadership.
This dynamic was at the centre of a candid conversation at the Toast Summit in Toronto, where women in tech, allies, and those navigating careers in technology gathered for a day of honest dialogue about workplace equity.
Hosted by Toast, a membershipbased collective focused on getting more women hired, supported, and promoted in tech, the event challenged attendees to examine what leadership actually demands inside systems that often reward conformity while punishing dissent.
In a session titled “Showing Up When It’s Hard,” three leaders shared deeply personal stories of how they navigated some of the most difficult moments in their careers. While many organizations promote inclusion on paper, their experiences revealed how leadership is often shaped inside personal risk, uncertainty, and difficult tradeoffs that policies alone rarely address.
For companies serious about retaining and advancing women in leadership, this conversation offered a clear reminder of what leadership looks like in practice.
Here are five leadership lessons that emerged from the panel.
Lesson 1: The most defining leadership moments can be the most costly
In a business culture that celebrates bold leadership, companies often overlook what boldness costs individuals who speak up. Publicly challenging dominant narratives can quickly become reputational and financial risk.
For leaders who hold marginalized identities, these moments carry even more weight, especially when controversy moves beyond professional spaces and into personal safety.
For Samanta Krishnapillai, founder and CEO of Group Project Initiatives, one of those moments came in October 2023.
After posting a public statement addressing the complexity of the war in Israel, she faced a wave of online abuse. She was labelled a terrorist, received death threats, had her personal address shared online, lost clients, and was removed from speaking engagements.
At one point, she was afraid to leave her home, but she didn’t back down.
“I knew what I was doing was right,” she said. “I wasn’t going to let fear stop me from taking up space.”
Krishnapillai spoke openly about how earlier experiences had shaped her ability to endure moments like this.
A decade earlier, she had survived a suicide attempt, and the years that followed forced her to build the tools that would later carry her through public crises.
“Once you’ve done that kind of hard thing, everything else feels more manageable,” she said. “You become really intimate with your shadow self and the things that it says. I’m okay now, but I know what it takes to climb back.”
Speaking up about values or taking a stand on complex issues can carry real consequences for leaders, especially in publicfacing roles. While many companies encourage employees to bring their full selves to work, those who challenge dominant narratives often absorb personal and professional risks that organizations may not fully acknowledge or mitigate.
These moments test not only individual courage but the depth of organizational support behind inclusion and psychological safety.
Lesson 2: Persistence often requires redefining progress
The narrative of “persistence” in business often suggests a straightforward path: keep applying, keep networking, eventually succeed. But for many internationally trained professionals, the barriers are not about effort, but systemic expectations of local experience, credentials, or networks they don’t yet have access to.
This disconnect can quietly push skilled immigrants out of industries that claim to value global talent.
For Luisana Rocha, now vice president of client services at StackAdapt, discomfort came in a different form.
After moving from Mexico to Canada, she assumed her international experience would open doors. Instead, her applications were repeatedly dismissed for lacking Canadian experience.
“How can I acquire Canadian experience if no one is willing to hire me?” she recalled.
Rather than give up, she changed her approach. Rocha took on an unpaid internship, worked retail to support herself, and slowly built a network from the ground up. Even after finally landing a job offer, her progress was nearly derailed again when the employer rescinded the offer due to her immigration status.
Still, she kept going.
“I kept showing up for myself,” she said. “When I see candidates who have moved across countries or industries, I know they’ve built resilience. That kind of experience brings unique value.”
She also spoke about learning to be less harsh with herself in difficult moments.
“I used to replay everything that didn’t go right, constantly questioning what I should have done differently,” she said. “Now I remind myself of what I have overcome already. If I’ve done it before, I can do it again.”
Global companies frequently promote the value of international experience and diverse backgrounds, but many still filter hiring decisions through narrow local standards.
For anyone starting over or entering a new industry, building connections matters long before the job offer arrives. Rocha advised using every opportunity to meet people, attend events, and seek out mentors who can help open doors. Once inside an organization, she encouraged women to stay visible, participate actively, and speak up, emphasizing that visibility plays a critical role in career growth.
Lesson 3: Leadership often means shielding your team from the weight you carry
Economic uncertainty, interest rate hikes, layoffs, shrinking budgets — these external pressures often create intense strain for founders and managers. While teams may feel protected from the full financial reality, leaders are left absorbing the risk, making quiet sacrifices to keep businesses alive and teams intact.
Sarah Stockdale, founder of Growclass, built her company through a pandemic, two recessions, and the birth of her first child. The financial strain nearly forced her to sell.
“I almost quit,” she said. “When the Bank of Canada raised interest rates, my son was born the next day. We were running out of money as my customers were getting laid off.”
Instead of exiting, Stockdale chose to stay, after hearing advice from someone at a conference who pointed out that her competitors had taken venture capital while her business was bootstrapped. The message was simple: “Just outlive them. Cockroach it out. Just don’t die until your competitors die.”
Stockdale stopped paying herself, cut expenses, and focused entirely on survival. That discipline carried Growclass through the hardest period, and today she leads a growing team. But even with the business stabilized, she remains deliberate about protecting her employees from that uncertainty.
“I own the business, so I get the stress,” she said. “My job is to create as much psychological safety as possible so they can focus on doing great work.”
For leaders, especially founders, survival often depends on how much risk they are willing to carry personally while keeping their teams focused and protected. The work of leadership in crisis is not only financial but emotional, requiring a deliberate choice to absorb uncertainty so others can stay steady.
Lesson 4: Internal resilience requires deliberate work
The ongoing leadership conversation about psychological safety often focuses on what companies can do. But for many leaders, the work also happens internally.
Managing anxiety, fear of failure, and the pressure to appear steady requires constant attention. Without deliberate tools and support systems, the accumulation of these invisible pressures can quietly erode leadership capacity.
“I have a lot of anxiety and generalized with a panic disorder — it’s like a fun cocktail,” Stockdale joked. Therapy, coaching, and learning to care less about being liked by everyone became essential tools.
“You don’t want to be liked by everyone. If you’re liked by everyone, it means no one loves you. So you need to cultivate a little bit of that antienergy and be okay with that.”
Rocha echoed the need to stay grounded even when drained.
“If I show up to my team just feeling overwhelmed, negative or complaining, that’s really going to spread,” she said. “As a leader, I’m not trying to shy away or hide the fact that things get hard. It’s more about, okay, let’s put some action. What are the things that I can control?”
Krishnapillai added that leadership often requires balancing confidence with uncertainty.
“It’s often a mix of both totally knowing what to do and also having no idea what to do,” she said. “Perspective is from every angle. I think understanding what’s yours to hold, and then how to leverage the different skill sets within the group.”
Lesson 5: Taking up space is a responsibility, not a personality trait
As more companies talk about the importance of diversity in leadership, the conversation often focuses on whether women feel confident enough to step into opportunity. The panelists emphasized that taking up space requires more than confidence. It’s a responsibility, particularly in cultures where less qualified voices often dominate because they speak first and loudest.
“Most people are not as competent as they’re pretending to be,” Stockdale said. “You can take up those spaces and just assume that you know because that guy doesn’t know shit.”
Krishnapillai emphasized that showing up extends beyond personal advancement. “You’re also on Team Humanity,” she said. “Silence is not neutral. You have a duty to show up.”
Rocha urged women not to wait for perfect conditions before stepping forward. “Make yourself visible,” she said. “Participate. Speak up.”
The conversation closed with a shared recognition that discomfort may be unavoidable. But inside those difficult moments, leadership takes shape.
As moderator Christine Tatham, CPO at Redbrick, reflected, “We all have those moments where you feel like you cannot continue. But you can. And often, those are the moments that define you.”
is the official media partner for the Toast Summit.
