A bit of career advice:
Every day, try to find a little bit of sky that could fall on your project. Then tell your boss about it.
You might think your job was to methodically think through a plan and deliver on it. You might even think you get rewarded for delivering on-time and on-budget, growing leaders, and helping your folks maintain a work-life balance.
Wrong. Delivering the above are table stakes. Expected.
What matters most, especially to executives, is worse case. They/We love Cassandras who foresee land mines, snakes in the grass, and train wrecks.
No matter how remote the risk, bosses will love you for pointing them out.
Of course, you have to then own the risk and make every effort to avoid it.
If you do, tomorrow, you’ll have to find another snake.