You see the project going down a bad path…

You did some initial research, not comprehensive (obviously) due to time constraints, the project is already in motion after all, but it’s enough to confirm your suspicions (or bias, or intuition) that something is not right and needs fixing.

Voice too many concerns, or a concern too big, and you’ll grind the project to a halt. The gaze of the entire organization, the ire of management, all falls on you. A spotlight of insecurity begins to shine. Does your bank account have the social capital to cover this debit? Is this political suicide? Have you sufficiently divorced your concerns about the project from the personalities working on the project?

After passing all internal checks and you still feel compelled to say something, you attempt to pump the brakes of an already moving machine. Ideally it’s like the sport of curling, a few gentle sweeps to correct the course of the already in-motion object. But if your blaster is not set to stun, you end up scorching every participant in the project. It has to be perfect, no margin for error. Overly couch your language, you subvert your own message. Overly assertive (or even just competent at your job), you’re seen as an asshole.

For me, it takes an immense amount of mental and emotional energy suggest a departure from the plan. I don’t mind if the plan changes, but I don’t want to squelch the fires of progress.

Some people excel at overcoming this mental hurdle. Their brain works different, I guess. No hesitation, a mountain of chutzpah, a wellspring of radical candor. They vocalize opposition to sentences mid-flight. They stop meetings to question the entire premise of a project. They burn piles of money on conference room tables for enjoyment. They have wit, and drive, and gall. The ghost of Steve Jobs, smiling and applauding their warpath.

Is it possible to be this? Am I this? Do I want to be this?