Episode 7: Why Leaders With Heart Provide Safe Spaces For Their People

Leadership is not about perfection. It can be tough and messy. This journey of being a better leader has a lot of hills and valleys, and we have to be able to take those punches as we go and continue to be there for the people we are leading.

Our guest for this episode is Sarah Bierenbaum. Sarah leads a section of the Customer Success team at Olo, a SaaS company in NYC; she’s a Senior Director overseeing a team of 20. Her leadership career has ranged from theatrical stage management, to general management, to her current role in tech.

She believes if we take the time to understand each other as human beings, we will build a better world.

Today on the podcast we talk about her leadership style, where her drive comes from, the importance of empathy and how she creates safe spaces for failure.

Click the play button below to listen to the rest of the episode!

The Space to Fail

An extreme interest in other people is what drives Sarah to be a leader. She has always felt that understanding each other as human beings is how we build connections, find creative solutions and do great things.

If you’re trying to solve a problem or trying to accomplish something, you are doing so with other humans. For her, a big part of leadership is understanding the people she’s collaborating with and figuring out how to use their different skills and unique qualities to accomplish something they couldn’t do on their own, or with a different set of people.

Her work history is somewhat unusual for someone working in the startup world. She spent 15 years or so working as a professional stage manager. She had a Masters in Fine Arts in Stage Management and so she spent a lot of time working with artists and supporting them artistically.

Sarah-Bierenbaum-Quote-Card

A huge part of a stage manager’s role is to create an artistically safe space for all of the different people in the room and outside of the room, to try and fail, and try again, until they create something amazing.

There’s a lot of supporting space for failure, which has always been at the heart of leadership for me. Share on X

Sarah’s leadership style

“As much as possible, I try to lead by asking questions and listening. When I hear what my team – or whoever it is I’m talking to – has to say, I try to repeat that back in a way that helps that person understand what I’m hearing, what they said, and hopefully can also guide them to coming up with solutions.”

I like to understand and help the person I’m talking to understand, and ideally help them come up with a solution and support them in the solution that they want to try. Share on X

Ask for feedback when things go wrong

Sometimes, leaders mess up. But when they do, they’re quick to become aware of it, and they ask feedback from their team about where they went wrong and what they can do to improve. Share on X

When Sarah handled a meeting in a way that made members of her team feel frustrated, she asked them to give her feedback and how she could do better.

It’s empowering for team members when leaders ask for feedback from them, because they know that their words are going to mean something to you. Share on X

Mentions

Connect with Sarah on LinkedIn

Becoming Unshakeable Podcast

With Heather R. Younger

Becoming Unshakable is the podcast for leaders, creators, and changemakers who know TRUE LEADERSHIP starts from within.

Each episode explores what it takes to lead with resilience, compassion, and purpose while staying human through it all.

Through candid conversations with executives, frontline leaders, coaches, and everyday heroes, Heather uncovers the real stories behind growth, compassion, setbacks, and transformation.

From navigating change to creating emotionally safe cultures, Becoming Unshakable reveals what it really takes to create leaders—and organizations—that can’t be shaken.

Hi, I'm Heather

I've been through every type of
ORGANIZATIONAL CHANGE
you can think of.

Layoffs, reorgs, mergers, acquisitions and major technology shifts. More than 20 years leading teams through high-stakes situations where results mattered, people depended on me, and decisions couldn't wait.

Those years taught me how to lead. But they also showed me the hidden cost of always being the one who holds it all together.

During our second reorg in less than a year, I walked out of a meeting with no say in what was happening, just marching orders. When my team asked how the meeting went, I should have said, “Give me 15 minutes to process this.” But I didn't. Instead, I let them absorb every ounce of my frustration.

Then I saw their faces.

The people who looked to me for stability had just watched me unravel. What was that teaching them about their ability to handle the pressure?

That moment changed how I saw my role as a leader. Leading teams isn't only about grit or resilience. It's about how your presence builds the trust your team needs to function when things get hard.

Today, I help organizations build unshakable leaders, teams, and cultures. Because when leaders become the calm teams can count on, organizations don't just survive change, they come out strong enough to handle what’s next.

Heather Sitting
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Contact Heather Today!
+1 403-398-8488

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Contact Heather Today!
+1 403-398-8488

Contact
Contact

I'm really interested in...

(select all that apply)*

I can be reached at...

Additional Comments