Nobody pulls out the chair for you. That is one of the most important things Cassandra Brown has learned in nearly 15 years at Walmart, and it shapes everything about how she leads today. If you want a seat at the table, you have to take it.
In this episode, Target Director of Cybersecurity Defense Bobby Haskins sits down with Cassandra Brown, Vice President, Asset Protection WMUS Stores (formerly Group Director of Enterprise Security Transformation and Support) at Walmart, for a conversation about what leadership actually looks like in loss prevention. The real version, full of imposter syndrome, trust batteries, accidental pivots, and the leaders who changed everything by investing in you when they didn’t have to.
Key takeaways from this episode:
- Leadership shifts from self-betterment to team betterment. The moment you stop saying "they" and start saying "we," something changes.
- Trust is not a one-time achievement. It is a battery that drains and recharges, and the best leaders stay conscious of both.
- Imposter syndrome is not a weakness. If you feel it, you are probably more ready than you think.
The career she didn’t plan for, and why she stayed
Cassandra started at Walmart to pay her way through a psychology degree. She had no intention of staying. Then an assistant manager named Becky Bishop sat her down, told her what a store manager earns, and changed the trajectory of everything.
That is how most great LP careers start. Not with a plan, but with a person who saw something and chose to invest.
"It started as one of the only things in the town I lived in as a way to pay through school. And you start to work for retail and you realize all the career opportunities that await you. She spent additional time with me. She wanted me to grow within Walmart. That's the reason why I got into retail, but it's ultimately the reason why I stayed."
The pivot into AP came the same way, through a leader named Jared who was hard on her in all the right ways. She called him in tears during the first week. She stayed and went on to lead enterprise security transformation across Walmart, Sam's Club, and supply chain. The through line across every move is the same: people work for people, not for job descriptions.
Trust is a battery, not a switch
One of the most grounded pieces of this conversation is Cassandra's take on trust. Not as a principle to aspire to, but as something that actively charges and drains in real time, and that leaders need to tend to consistently.
"There's something in AP where people kind of feel this 'out to get you' vibe. Nine times out of ten, when I'm telling my team about an issue, they say 'I can't get this store manager to buy in.' It's because you don't have their trust. And when you don't have their trust, you can give people feedback all you want, but they're not listening to it."
Bobby adds to this with the trust battery concept. Even when trust is at 100, one moment can drain it. The best leaders notice when that has happened and address it directly rather than hoping it resolves. For Cassandra, that means being honest, having high expectations, and making it clear to her team that when things go sideways, she is going to be there.
Be intentional about where you are going
Cassandra does not wait for the job to give her the experience. When she wanted to understand a part of the business she hadn’t worked in, she called someone in that space and asked to spend time learning from them. When she realized she needed to fill a gap in her leadership toolkit, she created a milestone for herself rather than waiting for a role to force the learning.
"I had that leader at the time who said, what's the last job that you want to hold with the company? And it made me think about, if I want to be this leader of transformation and innovation, what do I have to have on the resume so that I have less imposter syndrome and more experience in the tool belt when the time comes? Some of those pivots were just based on trying to be more intentional about what I felt like I needed to be a better leader."
She is equally direct about imposter syndrome. Feeling it is not a signal to pull back. Citing an idea she encountered in the book The Anxious Achiever by Morra Aarons-Mele, she points out that overconfidence tends to be less connected to actual knowledge than most people think. If you have self-doubt, you are probably more aware of what you do not know, which makes you more likely to do the work to close the gap. Use it as a superpower rather than a reason to hesitate.
Cassandra's advice to anyone sitting with their next leadership decision is simple. Just do it. The “just” is where most people get stuck. Stop there, and nothing happens. Move through it and everything becomes possible.
Watch the full episode to hear Cassandra's philosophy on feedback, why she leads mentor circles as a way to hold herself accountable, what she learned from the worst leaders she ever worked for, and lessons that have stuck with her longer than any advice she was ever given directly.
