Linda Swindling, JD, CSP: How to Ask Outrageously!

Chances are you’ve been there, watching someone else get the promotion or the study abroad opportunity or the picture with Jay Leno that you really wanted, but didn’t have the courage to ask. Perhaps you don’t want to be seen as greedy or aggressive… But the truth is that making the big ask builds relationships and establishes trust. Today’s guest is ready to help you ‘get your ask in gear’ and make those outrageous requests.

Linda Swindling is a ‘recovering’ employment attorney who spent more than a decade honing her skills in negotiation, mediation and dispute resolution before founding the executive development company Journey On in 2000. She has spent the last 17 years working with business professionals to create better working relationships. A recognized expert in negotiation and strategic consulting, Swindling has worked with prominent organizations such as MetLife, the American Heart Association, and the Four Seasons Hotels and Resorts.

A Board-Certified Coach as well as a Certified Speaking Professional, Swindling often serves as a keynote speaker and breakout presenter at regional and international conferences. She brought her expertise to the TEDxSMU stage, where she shared the principles of her latest book, Ask Outrageously: The Secret to Getting What You Really Want. Today she explains how to practice the big ask, the best approach to negotiating a raise, and how to deal with being seen as ‘aggressive.’ Learn to get into the habit of asking, even when you are afraid, and start capitalizing on opportunities to get what you want.


Key Interview Takeaways

Listen to what people say you do well and capitalize on it. It took 22 years of feedback for Swindling to realize that teaching people to ‘ask outrageously’ was her talent.

Get into the habit of asking. Practice negotiation at garage sales and flea markets. You’ll be surprised how often it works!

Determine who is the decision-maker. Go into a situation (e.g.: at the department store) seeking out the person who can say ‘yes.’

If you’re not hearing ‘no,’ you’re not asking for enough. When you are told, ‘No, I really can’t do that,’ ask one more time. Practice until you are bullet proof to the word ‘no.’

When asking for a raise, talk about what you bring to the table moving forward. Rather than listing past accomplishments, explain the value you provide now and how you will continue to generate revenue and make the boss look good.

If you are labeled as ‘aggressive’ for making the big ask, rephrase the comment. ‘Did it sound aggressive, or did it sound like leadership?’ We sabotage ourselves when we don’t use the right language.

Speak your strengths. Remind your colleagues – out loud – about the skills you bring to the table and the role you play in the organization.

Ask for forgiveness rather than permission. If you feel you must clear you actions with a supervisor, articulate your plan and ask if you’re missing anything.

Courageous people feel the fear, but ask anyway. 33% of people who want something big but don’t ask for it watch their opportunity go to someone else, so work through your fear and go for it!

Connect with Linda Swindling

Text ‘ASK’ to 42828


Linda’s TED X Talk

Ask Outrageously: The Secret to Getting What You Really Want by Linda Byars Swindling

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