By Wendy Widom, CBS Social Media Editor & Heather Sadusky, CBS Apprentice

CHICAGO (CBS) — This morning, when CBS 2’s apprentice Heather Sadusky stopped by my desk, I opened the conversation not by asking about her evening or praising her latest article, as I should have. Instead I said, “Oh wow, I like your necklace.” It was, by most measures, a female empowerment fail.

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Is complimenting a girl or woman on something external such a big deal? It’s a question that physician, author and parenting expert Dr. Deborah Gilboa — Dr. G. as she’s known to her 12,800 Twitter fans — touched upon last night at Second City, during her show about raising respectful, responsible and non-bratty children. She confirmed what I surmised: girls are praised way too often about external qualities and this habit, no matter how well-intentioned, may hurt or hinder them later on.

As Heather and I dug into the pros and cons of complimenting girls and women, we decided to record our conversation, which we’re sharing below. The similarities and differences in our outlooks — as a 20-something recent college grad and a 40-year-old mom working full-time in a tech role – may surprise you.

Wendy: What came to mind when I complimented you on your necklace?

Heather: My first thought was thank you! I rarely wear jewelry to work so it was nice to be noticed for my put-together look.

Wendy: When I said I shouldn’t have commented on something superficial, what did you think?

Heather: I understand why. It’s an external feature, not a compliment to my being. But I don’t think it was necessary to apologize for saying it. Compliments makes people feel good, especially girls.

Wendy: I often watch with fascination as young women navigate a world in which they’re expected to be the smartest in the room and look like Beyoncé. What kind of pressures do you feel?

Heather: There’s definitely pressure to be both and a lot of times it’s unrealistic. The hard part is that the pressure comes from many different sources: the media, peers, friends and loved ones. People want you to be a better you, but for various reasons.

What about you? Does it persist? Will I still feel pressure to be intelligent, beautiful, the whole package, twenty years from now?

Wendy: The answer, sadly, is most likely yes. My peers and I spent way too much of our 20s and 30s worried that we didn’t measure up in our looks, our popularity or our careers. Interestingly, this took place even when we knew rationally that we were attractive, nice and smart.

Even now, it takes a confident woman to say she doesn’t care if people notice she’s still carrying five extra pounds of baby weight, her house is a mess and she’s struggling to get her career back on track. There is frustration, a reluctant acceptance of the status quo and sometimes there is even shame at where we’ve ended up, which I worry we are passing along to you.

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Heather: This touches upon a similar topic I’m wondering about: in order to achieve a higher professional status, you need to be physically attractive.

Wendy: Studies seem to indicate a connection between attractiveness and salaries. When you add in how woefully under-represented women over 40 are in the media (TV, movies, magazines, etc.), the picture that emerges is pretty bleak.

National Women's History Museum And Glamour Magazine's 3rd Annual Women Making History Event - ArrivalsFortunately, however, we have role models like Diane von Furstenberg, Geena Davis and Amy Poehler, who are boldly speaking up about gender issues in our society, especially in the media. We also have a mentor right in our building, President and General Manager of WBBM-TV Marty Wilke. But we need more women to say – and believe – that getting older should be embraced and celebrated.

Heather: I think we have the wrong kind of role models. There are plenty of successful women in the spotlight, but very few are entrepreneurs or politicians…

Wendy: Or CEOs. The other part of this issue is women and competition. We need to do a better job supporting each other. Some women tend to see our resources as finite and perceive another woman’s success as threatening to their own. Do you see that among your peers?

Heather: Yes, it’s true. It’s the same thing; if she looks good, then I automatically look bad. She looks skinny and that makes me fat. It goes beyond our peers. I see it in every generation, even between generations. Do you feel that way towards younger women?

Wendy: I consider myself lucky because I have no desire to look like I did in my 20s or 30s. None. Zilch. I think the biggest disservice Andy Cohen and shows like the Real Housewives have done to women and to our society is convey that older women have a desperate desire to be or look young. I love being almost 41 and am excited about this new era of my life.

I wish our society saw women over 40 as smart, accomplished and, yes, even beautiful. I think there will always be a desire to feel beautiful; we just need to do a better job creating realistic expectations of what beauty is and put that lower, way lower, on our list of priorities.

Do you think we’re headed in the right direction?

Heather: I feel confident and I have friends who feel confident. I don’t worry about being perfect; I concern myself with being happy. As for the bigger picture, I think women are getting there, even though progress is slow. When I look at my younger sister’s generation, I know the fight is far from over.

How about you?

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Wendy: Strangely, I am optimistic, perhaps because I have a daughter and want her future to be filled with limitless opportunity. I think we’re hitting rock bottom now and that things will slowly improve. I see the brave young women at Northwestern, University of Chicago and Columbia University demanding that colleges hold perpetrators of sexual violence accountable. I see more women taking leadership roles in government and running companies. I also see women making an effort to support each other, no matter where we are in life. There are many challenges facing women, but our voices are growing stronger every day.