Back when I was sewing FUBU hats in my mom’s living room, I didn’t have a fancy office or a big team. But as the business grew, so did the team. And I quickly learned that leading isn't just about making decisions; it's about asking the right questions. Over the years, from FUBU to Shark Tank to CEO Access and dozens of ventures in between, I've discovered that the most effective CEOs I’ve worked with aren’t the ones doing all the talking; they’re the ones asking questions that unlock momentum.
Here are five questions I regularly ask my team to keep us aligned, motivated, and moving forward:
1. What's One Thing Slowing You Down Right Now?
At one point early on, we were stuck—production delays, missed timelines. It wasn’t until I straight-up asked the team what was blocking them that I found out a supplier was dropping the ball. We fixed it, fast.
Try this: Don’t assume you know the bottlenecks. Ask. Then remove them.
2. If You Had My Job for a Day, What Would You Change?
This one always opens up fresh thinking. One time, a junior team member suggested a new marketing angle. We tested it. It crushed.
Try this: You hired smart people—let them think like a CEO once in a while.
3. What are our customers telling us—directly or indirectly?
The smartest businesses stay locked in on what their customers actually need, not just what they think they want. I’ve seen countless entrepreneurs on Shark Tank miss the mark because they built something for themselves—not their audience.
Try this: Ask your team what trends, complaints, patterns, or requests they’re hearing. Your next move might already be hiding in plain sight.
4. Where Are We Winning—and Why?
When we saw FUBU sales spike in certain regions, we didn’t just celebrate—we dug into the data. That insight helped us expand smart, not just fast.
Try this: Don’t just ask what’s working. Ask why it’s working—then do more of it.
5. What's One Idea You Haven't Shared Yet?
Sometimes, the best ideas don’t get shared until someone gives permission. One of our most successful product launches came from a team member who just needed to be asked.
Try this: Make it safe—and expected—for your team to bring ideas to the table.
Final Thoughts
Leadership isn’t about having the loudest voice in the room. It’s about creating a space where your team’s voices can be heard—and then actually listening. You want to build something that lasts? Start with better conversations.
