How do you navigate the challenges of major career transitions?

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Managing Director in Finance (non-banking), 1,001 - 5,000 employees
Personally, transitioning from a large company to a small one, the hardest part was convincing people that you can successfully take somebody who's lived a life in a big Fortune 500 company surrounded by lots of people and lots of support and suddenly drop to little support where you have to do most of it yourself. I spend a lot of time talking to some of our operating partners about how I went from having a large budget with thousands of people to a small budget a handful of people. My emphasis would always be that I don't really care about what my budget size was. I don't really care how many people I have. But do I have the right people to make the right impact? Do I have the budget dollars to make that happen? At the end of the day, that's what matters most. But it's hard getting other people to see that you can do that because frankly, a lot of people can't. They've been burned by that experience so they really drill in on that side of things.

And more generally, the toughest part is actually the transition itself, because you get yourself all excited about the company. Early on, with the first couple transitions, you do believe the grass is greener on the other side. You come in with lots of energy, lots of excitement, but you suddenly find out you're  in exactly the same spot, except now you don't understand the politics, you don't have the relationships to draw on and you've got to rebuild all of that. And you go, "Okay, but maybe I'm going to learn something in the process here." If you're going to make a transition and I don't care whether it's a transition to another company or to another role, figure out what it is that you're looking to get out of it because 9 times out of 10, it's not going to be exactly what you expected, but if you fully thought through what you're looking to get out of it, you can make sure that at the very least that happens should things not work out the way you expected.
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Former Chief Technology and People Officer in Software, 1,001 - 5,000 employees

Same circus, different clowns.

Managing Director in Finance (non-banking), 1,001 - 5,000 employees


Senior Executive Advisor in Software, 10,001+ employees
The biggest thing that I saw as I moved from one role to the other was that every time you start in a new role, you always start from scratch. Going by John Maxwell’s five levels of leadership work, you’re at level one, which means you have just earned the right to lead. You have a title and everything that you do from there is dependent upon how you operate, what your integrity is and how you want to proceed with the group. It helps to understand that everyone has a right to speak but you need to earn the right to be heard. There is a lot of difference there and that reduces the amount of noise. Unless you are actually trying to improve the value within the organization, just don't make noise for the sake of noise. Growing in the same direction you need to be contributing.
SVP in Finance (non-banking), 1,001 - 5,000 employees
Figuring out if I really wanted to make the transition. In the last several months, I spoke to several peers and their advice is what helped me get there. It was a lot of networking, talking, and learning from people who are doing that today. That insight was really helpful in figuring out, do I really want to do this? Am I ready for this?

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Yes, I’d have several who would fit14%

Yes, I’d have one or two77%

Maybe, but they’d need significant training/mentorship5%

No, we’d need an outside hire5%