I had a bad leadership experience a couple of years ago and decided to take my career in a different direction and try and re-gain some work/life balance by going contracting. It’s been ok, but not quite the difference that I had hoped. I want to try and get back on the leadership merry-go-round but I worry I’ve burned my chances by stepping away for a while even though I had achieved a lot and had a great looking resume. Any advice?

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Define “bad leadership experience”?

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Toxic company. Endemic problems in the region I inherited which I dared to tackle and try to fix. Apparently I should have just ignored them. I also inherited a load of failing projects which I tried to turn around but I was spread too thinly. The whole thing was a shitshow but the way the company behaved with me was inexcusable. Put me off trying to use my experience to good effect again. However I realised over time it was them, and not me.

Are you trying to go back to the same company/role or are you looking to branch out? My guess is you'll be fine. You'll potentially need to frame up why you went out on your own, but if you can do that positively I don't think that'll be an issue

I’m definitely not trying to get back there. I’m talking about other roles with other companies. Maybe it’s more trying to even get an interview for leader positions at the moment as it seems every role has a million applicants.

You are right to worry. For any leadership team to embrace you and bring you in, they would need to feel confident about trusting you in that role. It’s not impossible. But if you plan to go about this by stressing your past accomplishments and experiences, you are looking at a long and rough road. Google me and take my free training on how to do this the right way.

I'm sorry for your past experience.

My opinion is that you were effectively leading yourself during these last few years of contracting, and I would view it as running your own business. How can you frame the work you've done during this to help you get a first step in the door?

Ultimately, this boils down to: What leadership have you demonstrated in the past few years from contracting? Yes, it's not the same as what an employer will want, but it might help you get a conversation started with a prospective employer.

That said, I suspect you will have to enter a leadership position from "the ground". So, a question to ponder in the background: Would you be happy with doing that?

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