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Belinda Oakley: “To build a great team, psychological safety trumps all”

Psychological safety trumps all. No matter the team, no matter the task, no matter the talent… if you don’t have psychological safety you do not have a solid foundation on which to build a great team or a great organization. While it has most certainly been my experience, this one is also backed by science. […]



Psychological safety trumps all. No matter the team, no matter the task, no matter the talent… if you don’t have psychological safety you do not have a solid foundation on which to build a great team or a great organization. While it has most certainly been my experience, this one is also backed by science.


I had the pleasure to interview Belinda Oakley. Belinda Oakley is CEO of Chartwells K12 where she leads a team of 16,000 employees to reimagine the school lunch experience for 2 million students in 4,000 schools (talk about a huge responsibility!). A native Australian with a non-traditional career path, her two decades of foodservice management experience have led her to live on three continents and share unique perspectives and valuable insights to help teams and companies succeed. Whether it’s changing culture or transforming business operations, she believes anything is possible if you stay true to your mission.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Growing up in Australia, I was what many would describe as a ‘latchkey kid’ — independent from the get go. As soon as I was legally able to get a job, I started working in food retail and found that I enjoyed the customer interaction, team environment and of course… the food!

When I finished school, however, I pursued a degree in Psychology because I’ve always been intrigued by human behavior and didn’t view my after-school jobs as any kind of career path. While studying, I simultaneously worked full time as a store manager in Australia’s largest bakery franchise. A year into my degree program, the company offered me a regional leadership position which changed the course of my entire career and ultimately, my life.

Can you share the most interesting story that happened to you since you began leading Chartwells K12?

A couple of months into the role, I received an email from a 20-year associate named Ellen who was retiring. Entitled ‘If You Want to Be Successful’, she shared advice on everything from broadening the inner circle to simplifying the work of our managers to celebrating the passion of our people.

I have referenced that note from Ellen several times and of all the direction and suggestions I received (even from the most senior leaders in the business), I’ve taken her advice to heart the most and it has paid dividends. It is incredible how much you can learn from your front-line associates if you are open to listening. They are the pulse of your culture.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I started as CEO of Chartwells K12, I had just come back from maternity leave and was trying to not only balance my new responsibilities as a mother, but to succeed in the biggest role of my career. I was scheduled within an inch of my life and somehow fit in pumping sessions in the brief windows between. From airplanes to public toilets to sitting in my car, I feel like I had pumped everywhere and still managed to somehow show up at my appointments appearing CEO-like. A few months into the role, I was given an opportunity to speak at a high-profile event; once again, I had back–to-back calls from the moment my flight landed to briefly before I spoke. Luckily, I found 15 minutes when I could pump in the lobby restroom of the conference center since I failed to organize a room or block enough time to use one of the airport nursing rooms. As I precariously positioned myself in the family restroom on the uncovered toilet, complete with speaking notes on my lap and pump balancing on my handbag, I heard the automatic flush. It took a few seconds to sink in and then I sprang up aghast! The back of my dress was saturated and I was scheduled to be on stage in 10 minutes. There was no hand dryer… no one to call… nothing I could do but frantically dab at the wetness with paper towel and imagine the entire audience pointing at my suspect attire. Eventually, I caught sight of myself in the mirror and couldn’t help but laugh. With pumping gear still attached, my dress spun backwards to aid in the clean-up and speaking notes strewn across the floor, there was nothing CEO-like about my appearance. I composed myself as best I could, convinced myself that I could give the entire presentation walking like a crab from side to side and in the forty minutes that followed, did exactly that. No one pointed, and I’m pretty certain no one even noticed. Once I began talking, I almost forgot how mortified I had felt only minutes before.

Only a few weeks later during a presentation to about a hundred regional team members in our organization, I was struck by how many questions centered on work-life balance. People wanted to know if I had a stay at home husband, if I had a nanny for my daughter… they were trying to figure how I ‘held it all together’. I told them the truth about how un-together things often were and made a commitment to share moments like this one.

The lesson for me was to stop pursuing a CEO-like state all the time and just lean in to the messiness. I believe by doing so, I can help my team be more forgiving of their own messiness knowing there is no such thing as perfect.

What do you think makes Chartwells K12 stand out? Can you share a story?

There is no question, it’s our people. The everyday heroes who are making a difference in the lives of millions of children we serve every day. In many of our 4,000 schools, the lunch period is only 25 minutes so it’s not unusual to have more than 300 children arriving at the cafeteria at the same time. While it’s hard not to assume it’s somewhat of a production line, what continues to make me extremely proud is the way our amazing people truly see each and every child. When you think about it, the ‘lunch lady’ (or gentleman!) sees more children in a day than any other member of the school administration or faculty so they really do contribute to the wellbeing of the students — and not just from a child nutrition perspective.

I see the impact that our team makes on students from coast to coast, but one story always comes to mind. Emblematic of so many of our associates, Nancy is a manager of an elementary school cafeteria in Arizona and she happens to have ten grandchildren of her own, but treats every child as if they are one of her grand babies. One day, I was standing in the cafeteria talking to Nancy as the third graders filed out and the fourth graders filed in. Suddenly, I saw a little girl with long brown hair throw her arms around Nancy’s legs and rest her head on Nancy’s stomach. I could have been invisible. Nancy stopped mid-sentence and spoke with the girl for a little over a minute. The little girl looked sad when she came over but as Nancy kneeled down and gave her a big hug, I saw the corners of her mouth turn up. She ran back to her place in the line and Nancy tried to pick up where she left off. I stopped her and asked, ‘is that one of your grand babies?’ Nancy shook her head and said ‘she’s having a hard time at the moment so I just try to give her a little extra love. They all need a little extra love sometimes’.

This is what makes Chartwells K12 stand out. Our people will always take the time to make the difference. Every child, every meal, every day.

Are you working on any exciting new projects now? How do you think that will help people?

We’re on a mission to reimagine school dining and recently launched an exciting new program in our high schools called Student Choice. We want the cafeteria to be a place students want to be, not where they have to be, and that starts with giving them a choice in the experience. Student Choice kicks off with a tasting event that is a lot of fun… we’ve created multiple restaurant-inspired concepts featuring menu items that are good for you and taste great. Over the course of a week, students get to try each of them and vote for their favorite.

Once the votes are tallied, the cafeteria is transformed into that restaurant which the kids just love. Because so many kids are scheduled from morning to night, the lunch break is so important. Making the cafeteria a place where they truly feel heard builds confidence and encourages connection. I think we all benefit from a world in which the next generation feels more connected, confident and heard.

What advice would you give to other female leaders to help their team to thrive?

Be you, 9 to 5 and 5 to 9. People are watching and in today’s digitally enhanced world, I think we need role models who are not just inspiring because of their intellect or talent, but because of their humanness. By letting yourself truly be seen, you unconsciously give everyone permission to show up differently. When people believe they can be their real selves, they give more. As a result, you get a more connected, inclusive and courageous culture.

What advice would you give to other female leaders about the best way to manage a large team?

Listen, share the feedback and facilitate team norms as soon as possible. No matter the culture of the organization or team, this has always worked for me. I’m a big believer in meeting people where they are. Beginning by listening to individual stories is a great way to mine for insights while allowing people the chance to be heard. From there, I like to bring the group together to share the key learnings — it’s amazing how similar people’s experience can often be and there’s great power in connecting the seemingly disconnected. I use a simple “Stop, Start, Continue” exercise to get underneath what’s getting in the way. Flip that feedback to an affirmation and you have team norms… a common agreement on how each member of the team needs to behave in order for the team to be successful. In doing this first, you move a long way towards psychological safety which is at the heart of most performance or behavioral issues that will come up down the line.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are probably three — all bosses at different stages of my career — who have contributed significantly to who I am as a leader, a mother and a wife. One served as a mentor, the other a best friend and the last, my champion. Leaders hold such a significant amount of power over people — both inside and outside of working hours. The ones who wield it for good raise you up to be more than you thought you could be while the others can leave you questioning everything. Having worked for both at some point in time, I’m grateful for the three that stand out who ultimately brought out the best in me.

How have you used your success to bring goodness to the world?

As a leader, I see my responsibility as much more than just business results. I believe I have an incredible opportunity, along with an equal responsibility, to empower my people to become more than they ever could have imagined — both at work and at home. I lead mothers, fathers, sisters, brothers, daughters, and sons, and I think of them in that way, first and foremost. This changes the way you lead and I believe, it changes futures.

For me, I have always felt an equal sense of both debt and destiny about my leadership position. Debt in that great leaders have changed the course of my life and I feel compelled to pay that forward every day. Destiny in that what started as a latchkey kid working a food retail job was guided from Australia, to the United Kingdom and now the United States to continue that mission. Over the past twenty years, I believe I have helped countless people experience true belonging, connection and success and I have no doubt many are out there paying it forward as we speak.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example, if possible.)

  1. Psychological safety trumps all. No matter the team, no matter the task, no matter the talent… if you don’t have psychological safety you do not have a solid foundation on which to build a great team or a great organization. While it has most certainly been my experience, this one is also backed by science.
  2. Being kind is more important than being nice. Recently, Kim Scott wrote a book about this very trait called ‘Radical Candor’. She says it best when she explains it as the “ability to challenge directly and show you care personally at the same time”. People will grow and teams will transform if you can prioritize this.
  3. When you get furious, get curious. We are hard wired to make assumptions and that often gets in the way of good decision making if you don’t override your instinct to judge. I use this as a fun way to remember to stay in “learner mode” by continuing to ask questions when you feel triggered or frustrated.
  4. No one can strike the balance for you. My husband heard this early on in his career when discussing work-life balance and I try to remind myself and my teams of this regularly. Burnt out talent is no good to anyone. We have to encourage our people to prioritize living a life they love.
  5. Failure is inevitable so let go of perfection. Brene Brown calls it the physics of vulnerability — if you are brave enough often enough you will fall. I think it’s extremely helpful to keep this in mind and create a safe zone if you strive to promote a culture of innovation.

If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Owning our stories and telling them because as Mr. Rogers said, ‘there isn’t anyone you couldn’t love once you’ve heard their story’. I think learning to love your own story helps put away some of the armor you’ve built up. The less judgmental you are with yourself, the less you’ll be with others.

What is your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our Light, not our Darkness, that most frightens us. As we let our own light shine, we unconsciously give other people permission to do the same.” I cannot tell you how many times I have summoned courage from Marianne Williamson’s quote. It was shared with me in my early twenties by someone who saw more in me than I saw in myself at the time. I think a lot of leaders and in particular, female leaders, feel the need to play small at times for fear of standing out or speaking out too much. This continues to remind me to be kind to myself in times of self judgement and encourages me to shine on.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why?

Arianna Huffington or Brene Brown, because they both changed my life. First and foremost, I’d like to thank them while I continue to glean as much as I can from their wise words. In the meantime, they will remain my role models.

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