How do you know when to leave a role?

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Board Member, Former CIO in Software2 years ago
I like to make the provocative claim of being a quitter. I quit my job at KLA-Tencor in 2009 so that I could go back to business school to figure out what I wanted to do next. It was that moment that helped me find Facebook. Had I not done that, I don't think I would have been on the path that I'm on now. I joined Facebook in 2010 and stayed there until the end of 2016, when I quit again.

I quit Facebook in 2016 to start Woven, a productivity software startup. We were a calendaring solution, and I ran that for about four and a half years until we sold it to Slack. So even though I joke about quitting, a big part of my life story has been about making space for what's next; when I did that in 2009, it paid off in huge dividends. And the same was true for leaving Facebook. Now I'm making space again. 
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Director of Technology Strategy in Services (non-Government)2 years ago

When I was made redundant from a role in a bank, I was able to take 56 weeks' salary and leave to do my own thing the way I wanted to. I know many people see it as a bad thing, but it was a great opportunity for me. You're not often given a paycheck and told, "Go away, we don't want you anymore," so I took that.

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CTO in Healthcare and Biotech2 years ago
For me, it's when I'm not happy in the role, it could be several factors that push me to acknowledge that I'm not happy anymore. It could be that my Manager has not the same values as I do, also that there is persistent chaos & lies in the team which I'm not fond of. If I don't feel challenged anymore, to me it's time to find new ventures.
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Director of IT in Software2 years ago
When you are not happy anymore,m and when you stop feeling supported by your boss/company. When you stop learning and progressing.
Director of IT in Educationa year ago
When you feel that there is no value addition happening from your side, then it is clear that your role can become redundant to the organization. Self performance survey from your clients may help to decide it. Once you are very much sure of the same, then it is better to leave that role.
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Director in Manufacturinga year ago
My reasons have varied

Bored with the role
Team was downsizing
Lack of promotion opportunities
Saw a role posted I thought I would enjoy
And rarely- disagreed with my bosses “style of leadership “
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