I was a research analyst at Sanford Bernstein, and I was asked if I would consider becoming director of research. I was flattered, of course. But I didn’t want the job. What I really wanted was to be associate director of research. And I wanted my mentor — the guy who hired me — to be the main guy.

It seemed to me that this would be a great answer. A baby step into leadership for me; with the cover of a someone else who would have to be the real boss. I could be a COO type; he could be the CEO type. He could make the big decisions; I could help him and offer him counsel.

So why didn’t I want the top job?

And it just seemed, you know, more ladylike to be the second in command, rather than to be the big boss.

After all, I had seen the caricatures of women bosses; none of them at that time were great. (It was the 1990s — though we could have a long debate on how much this one has changed.)

And I had grown up in the South, where I was taught that I should strive to be likable. To be the boss might mean being on the outside of my group of peers. I had been on the outside before, having been bullied in middle school, which was no fun. And I had been on the inside before, as a cheerleader in high school — yes, seriously — and it was much more fun.

But the associate director of research option wasn’t available; senior management wanted me to take on the lead role. They thought I could do it.

How did I get the courage to take the job? I went into active risk management mode, comparing the upside of this decision to the downside. And then I worked to reduce the risk of the move.

So what was the upside? A big new learning experience and the opportunity to have an impact on the investing community, and thus on individual investors. Pretty cool.

The downside? Perhaps being deemed one of the “not likable” caricatures. And public failure.

I pushed on this some more: What would happen if I failed? Well, I’d been a successful research analyst, so I was pretty sure I could beat a partial retreat back into that job, if need be.

What happened after I took the job

There were some tough times from then on for me personally (a few cranky analysts made it clear I was no longer “us,” but had become one of “them,” as I’d fretted about) and for the business (we made the controversial business decision to get out of underwriting, given the client conflicts of interest, and lost analysts and revenues from it, before the strategy worked).

But perhaps my most important leadership lesson was that not being “liked” by everyone wasn’t terminal for me. And that the coaching aspects of leadership were an incredibly rewarding way to spend my days.

So, as I’ve moved on to additional leadership positions, I’ve been less hesitant. But I’ve employed the same risk management approach in each leadership role as in my first: identify the upside and the downside, and then work to reduce the risk.

Take over management responsibility for Smith Barney and turn around its research business? Upside: stretch myself to lead a business at large scale, through turbulence. Downside: public failure and humiliation. I decided to do it.

Take over management responsibility for Merrill Lynch after Bank of America acquired it? Upside: have the opportunity to restore a storied brand after the subprime crisis and reverse its exodus of financial advisors. Downside: public failure and humiliation. I decided to do that, too.

Launch Ellevest? Upside: make a real difference in closing the retirement savings gap by making a dent in the gender investing gap. And, while doing so, help women reach their financial goals and positively impact their lives. Downside: again, public failure. Oh, and humiliation, too.

On each of these, working to reduce the risk was always the next step, after accepting the job.

The answer? Always, always, always, it was about getting the right team in place, with the diverse skills to bring out the best in each other.

And that has meant diversity in every way: putting together a team of people who grew up in the business and people from outside of the business; optimists and pessimists; risk-tolerant and risk-averse; diversity of gender and skin color; diversity of education; diversity of background; diversity of age.

I have been part of teams that have not had this type of diversity; and it frankly just felt easier, on a day-to-day basis, because we all agreed so much of the time. But, in my experience, it is only by pulling in the full range of opinions and perspectives that the full range of business options and alternatives can be explored. And only in doing that can risk be reduced.

Get this right, and this will help you get a lot of other things right as well.