I get called out by others for overthinking - until the risks I've pointed out become reality
It's all relative - one person can be thought of overthinking and the other person can be thought of as a 'cowboy' and just winging it
It's all relative - one person can be thought of overthinking and the other person can be thought of as a 'cowboy' and just winging it
There right balance of action and caution is the thing that enables you to move forward quickly without blowing up.
It also "takes all kinds" on a team since different people have a knack for one or the other. The problem happens because most people fall in love with their preference and are blind to its downsides.
A quick tell is - whenever someone's justification for something blowing up is "oh but I have a bias for action" -- they are basically oblivious to their recklessness and underthinking. Whenever someone says "oh but I am much more cautious and thoughtful than these cowboys" they are oblivious to how little they do (vs could be doing) because they are paralyzed by overthinking.
The person I like to work with is the one who says "man, I have a bias for over/under thinking but I try to catch myself in situations where it's not appropriate"
What has consistently helped in winning trust when providing feedback is pairing any concern with either a qualification (blocker/aesthetic/security), a solution, or both. Then, you not only expose the thought process behind your perspective that they've missed something - with which your audience may not agree, but can judge in earnestness - but also your intention to help and support their vision.