Most companies say they want their teams to take more risks. Then someone actually does, but the idea, campaign, or product doesn’t land – and suddenly the organization remembers why it felt safer not to try in the first place.
Tariq Hassan kept noticing that contradiction.
"You go into town halls, and you talk about it," he told Fahad Khawaja on the In Community podcast. “People would nod and smile and feel great, [then they'd] leave and go back to their day-to-day job, and things wouldn't change.”
Hassan, Chief Marketing and Customer Growth Officer at Wendy’s, saw this pattern at Petco and later at McDonald's, where he was Chief Marketing and Customer Experience Officer, US: leadership told people it was safe to take a swing, while the day-to-day reality made them believe otherwise.
A former manager gave him a simple framework that’s helped him to shift this — say it once, say it twice, and then put an action behind it.
A Quarterly Review for Failure
At McDonalds, Hassan's leadership team implemented a structure where they regularly gathered to review nominations for what he called "the absolutely greatest failures of the quarter."
The language was intentional. He called them the Amazing Almost Awards, and there were actual criteria for winning.
Was there a clear objective? Was there a cross-functional team? Were people kept informed along the way, so nothing landed as a surprise? And importantly, was there "some form of exhaust from the experience" the organization could build on or deliberately steer around next time?
If you’d taken a thoughtful swing, missed, and created something everyone could learn from, you were eligible.
That's a very different message from putting "FAIL FAST" on a wall.
Where It Came From
The part of Hassan's story that doesn't usually show up in a marketing case study: he's dyslexic, having been diagnosed his senior year of high school. It took most of his professional career, he says, to move it "from something I kept secret to something that I actually recognized as one of my natural superpowers."
"For a long time the biggest byproduct of my dyslexia was my own fear," he said. "Fear of how to navigate it, and then fear of being outed about it, like I might be broken or something. And it wasn't until I started to embrace that and create my own psychological safety that I started to take chances."
Then the connection, in his words: "I think it's why I leaned so hard into this dimension of fear removal."
The Amazing Almost Awards were the institutional version of something he'd already had to build for himself.
What Makes the Risk Affordable
A culture that tolerates failure still needs something underneath it, and for Hassan that's always been data.
Petco is where he proved the case. He went to the company's CTO and asked for a technology-led conversation about customer experience, which the CTO told him no CMO had ever done with him. What came out of it was a view of the business down to the individual pet and its owner, and that view reshaped product, services, and how the brand talked about itself.
But he's specific about how data earns its keep. "You've got to challenge the intimacy behind the data," he said. "Data in and of itself is not always just a straight red, yellow, green light response to things.”
His concern is what happens as AI absorbs more of the decision-making: "We're on the precipice of creating organizations that are all just structured around the data making you do things."
A team that only moves once the numbers have pre-approved the move isn't taking a risk. It's just executing.
The Lesson for Anyone Running a Team Right Now
Companies that stop taking risks rarely actively decide to stop doing so. Instead, they often don’t build the cover that makes failure survivable for those making day-to-day decisions on the ground in the organization.
At Petco, that cover was data. At McDonald's, it was a trophy for the best failure of the quarter.
Everyone else's version of this is likely to look different. The key to remember is this: right now, there are a lot of smart people sitting on good ideas, willing to take calculated risks but waiting for permission to say them out loud and to take action without the fear of what may happen as a result.
