When you feel like you're doing everything wrong.
I have vivid memories of my last boss. He would call me into his office and offer this feedback. "Is everything okay? People perceive you as aggressive." "Of course I am okay!" I might have replied. "Yeah, but people still think you're being aggressive."
Then I would set out and make things better. I would go up to people I thought I had been aggressive with and asked, "Am I aggressive with you? Our boss says I am." "Uhhhhh, no." Then I would receive a phone call from my boss.
Now thinking back, I wish I asked my last boss - and every boss or person I was accountable to - is, "What's one thing you see me doing - or failing to do - that's getting in my own way?"
I got in my own way - going up to people didn't help.
I got in my own way - being unaware did not help me.
I got in my own way - I did not seek out actionable feedback.
Asking the question creates the opportunity for actionable feedback. It invites the boss, coach, or person to be direct, open, and useful.
When you feel like you're doing everything wrong, consider asking someone the question. Be curious. Extract useful information. Then, make a change.
Inspiration for this post comes from Douglas Stone and Sheila Heen's book, "Thanks for the Feedback: The Science and Art of Receiving Feedback Well."