Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Cindy Whitehead, chief executive officer of the Pink Ceiling, which finances and supports innovations for women. To read the complete interview, check out other articles, and obtain subscription information, please click here.

Photo credit: Earl Wilson for The New York Times

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What were your early years like?

I had a nomadic childhood. I moved every year from the fourth grade through my senior year of high school. My father was with the State Department. We spent some time in upstate New York, where I was born. We bounced back and forth between there and Washington, D.C., and then overseas in both the Fiji Islands and in Italy.

How did you feel about moving around so much?

I went kicking and screaming every time because I’d finally get established and then we would move again. But in hindsight, it’s made me good at observation, pretty good at appreciating different points of view and hugely adaptable.

Tell me more about your parents.

They have very strong personalities. My mom is the quiet power, with a lot of compassion for others. She has always found a way to give back. My dad has a strong will to challenge the status quo. He was deeply a public servant who believed it was his duty to instigate change.

What was your first formal management role?

I had a sales team at Dura Pharmaceuticals. It was fun. The people in the group were very quirky, and they all were self-made. If someone is self-made, the skills they used to get to that point are going to ultimately make them successful in a team-based environment.

How do you determine if they’re self-made?

I’ll explore it in a conversation. How did you grow up? What did you do to first make money? I’m listening for whether they created their own destiny. If they’ve got that, they have that passion and that drive to pave their own path. Those are my kind of people.

Other lessons you learned early on?

I learned to speak up. I talk to a lot of women about that today. They often use all these qualifiers — the apology before they ask a question, or they’ll say, “Can I ask a question?” You just did. Ask the question. I learned to push myself out of my comfort zone, because if I had something to say and didn’t say it, I would stew on it.

You’re on your fourth company that you’ve started. Have you noticed big changes to the culture as they’ve grown past certain milestones, in terms of employees or revenues?

I have this wish to never go above 50 employees. Above that, there is a shift in the personal interaction you have with them. Below that, I can still remember your dog’s name and whether you just had a baby. At a certain size, you lose some of that.

I love knowing everybody. My quirk is that I nickname everybody who works for me, and I don’t know if I can nickname 250 people the same way I can with 50.

How do you come up with the nicknames?

Through the stories they tell over time. There will be something that is very memorable that totally captures them. It becomes a big thing the day you are nicknamed, and everybody knows the story behind why you get that nickname. You can literally go to company events and we only call each other by our nicknames.

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To read the complete interview as well as Bryant’s interviews of other executives, please click here.

Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times’ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.com that he started in March 2009. In his book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews of hundreds of business leaders. To read an excerpt, please click here. To contact him, please click here.