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Dare to Interview: 'Dare to Ask' Interview with the authors Cait Clarke and Neal Shister

Negotiating for women in this new century.

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This new and much needed book Dare to Ask!, authored by my friends and power couple extra-ordinaire Cait Clarke, a Washington attorney, and Neil Shister, who may be known to many readers from World Trade Magazine.

It’s time for a new book on negotiating skills. The past generation dealt with general psychology and mechanics but never with the gender issues which we are much wiser about today. Though written for women, if you really do want to create a workplace of diversity, you ‘others’ might want to become acquainted with this excellent book.

In addition, women are playing more leadership and representative roles, such as the last three Secretaries of State in the US, corporate presidents, lead legal counsel, sales and trading partnership managers. This book informs us of qualities that women possess which bring a new level of success to the organizations and endeavors they represent.

In the new generation, we want to be clear about who we are and what our interests are. We want to feel that we are above ‘game playing.’ So classes and discussions on ‘negotiating’ skills have kind of fallen out of favor in corporate America. 

However, the concepts in this book are about clarity and honesty, and also about fairness. We have seen many stories in the press and business world on deals going south, since they did not work for both sides. Time for a fresh approach. And this is it!

My interview is with both of the authors, which is interesting, since Neil obviously has a huge respect for Cait, but they both bring many facets to the discussion.

And now to The Interview………..

Please tell our readers a bit about yourself and what led you to write Dare to Ask.

Neil: Cait is the real brains behind DARE TO ASK! She’s a Harvard Law grad who works in the public interest sector. One of the things she does is give leadership and negotiation training. She has long been sensitive to how women get the short end in lots of situations because they won’t negotiate. A decade ago, I had written a ‘how to’ book on negotiating that did quite well, The Ten Minute Guide to Negotiating, and she wanted us to do a comparable book addressed specifically to women.

Cait: Most women hate to negotiate. Of course there are exceptions. But what I see all the time is women who don’t ask for what they want. Men will push back, women will roll over! Why is this case? Well, the research shows that negotiating has typically been a ‘boy’s game,’ done by men according to male rules. That means there’s lots of attitude that shows up at the bargaining table: competition, ‘one upsmanship,’ ‘I win/you lose.’ No wonder women don’t like to negotiate!

I include myself in this group. In the book we tell a story about what happened to me in my first job at a big Washington, D.C. law firm where I didn’t speak up on my own behalf. 

Women pay a big price for this reluctance. In our careers, in our relationships, when we make a big purchase like a house or a car we get treated differently than men. I kept thinking ‘if there was a way to give women confidence in their ability to negotiate, there would be much more equity.’

Neil is a terrific writer, and we decided to do a simple, accessible ‘guidebook’ that would inspire women to ask for what they want and teach them the basic techniques necessary to engage in successful negotiation. 

Our ‘Big Idea’ is that if you re-define negotiating as a win-win ‘Collaborative Conversation’ rather than ‘I win-you lose,’ women have natural negotiating skills—their empathy, their intuition, their ‘gift of gab,’ their talent for teamwork.

A new generation of people are running the business world—from baby boomers to gen x’rs. It’s much more personal, and I think the concept of ‘negotiating’ fell out of favor, but to our loss. Past ‘relationships’ can blindside managers while initiating partnerships, joint activities of some kind, and deals. Everyone wants to ‘feel good.’ And many of these interactions and transactions ultimately go poorly. Any thoughts for this generation?

Cait: That’s a great question, and one I hear often in different ways. Something we’re very big on in DARE TO ASK! is the importance of taking the time to determine what your needs are in a situation. I can’t stress this enough. Too often women just jump into a situation or a relationship or a transaction without first determining what they want to get out of it. So step one is this process of clarifying your interests and requirements. From there, you drill down to make specific demands---we call them ‘requests’ to be non-conflictual. That’s what you negotiate over, these ‘positions’ that you have developed to satisfy your needs.

Don’t feel guilty about having positions you want to satisfy. It’s not a personal rebuke. You’re not ‘disrespecting’ the other side. Just the opposite. You’re saying in effect “to sustain a successful relationship, here’s what I need.” The more specific the better. The other side isn’t necessarily going to agree to all your positions, but at least now you’ve initiated a conversation that is the basis for mutually acceptable expectations.

I need to emphasize that this is a continual process. Negotiating as we define it, as ‘collaborative conversation,’ is going on all the time. Sometimes it’s a formal process, sometimes it’s a quick interaction. 

What’s important is not to trust ‘good feelings and mutual respect’ as the basis for a complicated relationship that is subject to daily stress and pressure. Rather, periodically inventory your needs and then develop positions around them to ask for.

I loved the book and was nervous that now the men can have access to these secrets. But, if the goal is to develop successful win-wins, it might be worth a man’s while to also read and learn—to get more sensitized to their own gender bias.

Neil: I couldn’t agree more. The intention of this book is to empower women for the sake of more equity. Cait closes with a quote from the Dalai Lama: “The world will be saved by western women.” His point, as I understand it, is that by bringing the sensitivity and sense of fairness of women into the social and economic marketplace, all of humanity progresses.

Working on this book made me much more sensitive to the kinds of gender power bias that women suffer from and that men take for granted. And the negotiating techniques themselves are appropriate for anybody—man or woman. Win-Win means just that, the whole that gets divided up is greater than the sum of the parts that either side would get by itself.

How do you visualize this content being used? Do you see a new or enhanced path for yourself after the publication of this book?

Cait: We envision the book generating a community of women helping other women become empowered. ‘Diva Negotiators’ is our phrase. The web site,, features a Woman of the Week and also Peer-to-Peer sections where successful women talk about their experiences as negotiators and share secrets. We want to expand this so it can be increasingly sector-specific and situation-specific to be even more useful. 

We also are starting to give presentations to groups, “Become a Negotiating Diva in 37 Minutes” that distills the contents of DARE TO ASK! down into the essential message. 

We want to keep spreading the word that once women learn how to negotiate—and it’s easy—they don’t have to be afraid or reluctant to ask for what they want! 

You can get Dare to Ask! directly at the web site (for a better price than the book dealers).

Read the book, and let us know what you think!

To view other articles from this issue of the brief, click here.


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