Before taking a leadership job: Ask to see the financials
Really. Ask for the financial reports. Don’t be shy.
Case in point: I once applied for a job and was able to get a copy of some recent financial reports. But I couldn't make heads or tails of the reports. So I showed them to an auditor friend of mine and he couldn't either.
During the job interview, I asked each person about the reports, about the organization's financial health, the cash position, etc. They couldn't give me a good answer either.
Come to find out, while the organization wasn't in financial jeopardy, it had a very unhealthy culture around money. The unclear financial reports might have just been the result of 10-20 years of amateurs trying to make Quickbooks do things that Quickbooks was never meant to do, but I can't rule out the possibility that the finance committee hadn't intentionally made the reports worthless so that the board would have to defer to the finance committee before making any financial decisions. Without a doubt, the finance committee chair was the polar opposite of financial transparency and essentially had a veto over any money decisions the organization made. He had his own personal mission: never, ever spend any money.
It took a couple of years of concerted effort, but we eventually brought the organization around to a much more balanced and healthier culture around money.
The finance committee chair stormed off shouting "I predict doom!" More than a decade has passed and his prediction still hasn't come to pass. In fact, the organization had been slowly declining but today, because of those changes, is doing well.
Lessons learned:
Definitely ask for the financial reports
Expect a full and transparent discussion of the organization's financial health
If anything smells fishy, expect the worst and plan accordingly