The Obstacle in the Mirror: A Leadership Question Every DMO Should Ask

“What’s the biggest obstacle in your way?” It’s a simple question. But when you ask it with real intention—in a quiet moment, behind a closed door—it becomes a powerful mirror. For destination marketing organizations, asking this question as a leadership practice can reveal more than data ever could. Most DMO leaders are busy. Your calendar is a game of Tetris: board meetings, budget presentations, media requests, community events. But busyness can sometimes hide the very obstacles that keep your organization from growing, evolving, or truly connecting with your destination’s soul. Start by asking yourself: What’s the biggest obstacle in my way as a leader? Is it lack of funding? Outdated perceptions of your destination? A disengaged board? An unclear vision? Maybe it's fear—of change, of failure, of disappointing the people who trust you. You don’t need to answer out loud, but you do need to answer honestly. Now take that same question to your team. What’s the bigg...