Flags Don't Fix Things

Borrowed

“For follow-through to serve its function, action must follow analysis. Knowledge without courage isn’t effective.”

From "Execution" by Larry Bossidy, Ram Charan, and Charles Burck [Book]

Learned

Lately, I’ve felt like we’re already mid-week by Monday afternoon. There’s a lot in motion, and it’s moving fast. Fortunately, we’re starting to see our sales cycle gradually pick up. We’ve gotten better at creating momentum by moving conversations forward with clear next steps and involving the team earlier as projects become more likely to sign. Meanwhile, the team has their hands full with client work.

Last week, for example, we launched three websites for Instant Pot, MUSH, and McCormick. In the past, a week like that might have created uneasiness (for myself and the team) from the potential friction of multiple deadlines stacking up at once. But not this time. Each site went live smoothly. No fire drills. No surprises. Proud of the team, not just for the work, but for how they worked together and with our clients.

Weeks like this are energizing. They reflect many lessons learned, the systems we’ve built, the trust within the team, and the progress we’ve made. But even amid all the momentum, or maybe because of it, I’ve noticed something interesting.

It’s in these fast-moving periods that I tend to hear more flags. A concern about timing. A note about communication. A hesitation about scope. These usually show up as a “just flagging this,” shared in Slack or in passing during a meeting. The intention is good. Everyone wants to make sure we don’t repeat past mistakes. But it’s made me reflect on the role of flags and why I’ve come to question their impact.

The phrase “raising a flag” is common in work conversations. Someone notices something that could go wrong and calls it out. It’s positioned as helpful, a responsible heads-up. And on the surface, that’s exactly what it is.

But flags are often where the conversation ends, not where it begins. What starts as a thoughtful observation quietly becomes a form of insurance. If something goes wrong later, the flag can be pointed to as proof: I saw this coming.

Over time, this creates a pattern, one that can be harmful if left unchecked. We become good at naming what might go wrong but not at taking action to prevent it. The flag is treated like a contribution in itself, when it should really be the start of one.

That’s where the tension lies. A flag without a follow-up doesn’t change the outcome. It just marks it. And when that becomes routine (flag, no action, repeat), it reinforces the idea that awareness equals progress.

What would it look like if we approached flags differently? What if raising a flag meant staying with the issue just a little longer? Not necessarily to solve it entirely, but to offer an idea, a starting point, a next step. That shift from observation to ownership can make all the difference. It invites others in. If there’s concern, getting everyone to weigh in on a path forward can be a game-changer.

Luckily, I don’t see this as a habit within our team. But when I do observe it, I try to create space for the issue, and then help shift the conversation toward action. Sometimes that means turning a passing comment into the focus of a meeting. Other times, it’s a Slack message that prompts two or three follow-ups. These are small moments, but they’re opportunities to reinforce a culture of accountability and collaboration.

Often, it’s the little things that make the biggest difference in a team, like how we treat flags. Not as conclusions, but as openings. If we want to keep improving, not just avoiding past mistakes, but actively shaping what comes next, we have to be willing to move beyond observation.

Thought

When I point out a risk or concern, is it because I’m ready to engage, or because I want it on record that I noticed? Am I ready to collaborate on a path forward?