Interview with Linda Swindling: On getting what you want by asking outrageously

Vera: ‘Ask Outrageously’- that’s the bold title of one of your books. Most people fear rejection and therefore do not ask. What does it mean to ask outrageously?

Linda: For the purposes of this book, “outrageously” is defined as making a request outside your comfort zone.  There is a difference between outrageous and obnoxious. This is not a suggestion to be negative, deceitful or take advantage of others. People who ask outrageously are surprised by the positive outcomes and relationships which result from requesting more than usual.  Some typical results reported by people who were challenged to ask outrageously in 24 hours are; given raises and promotions, created a new business and granted real estate including a new home.


Vera: You say that if we don’t have what we want in life it means we haven’t asked or are settling for less- is it that binary?

Linda: Our research results support this conclusion. In fact, more than 96% of those surveyed said that they could have improved their results by asking for a little bit more or taking more of a risk. Almost a third said they could have increased their results by at least 50%. According to the Ask Outrageously study of almost 1,200 participants, the top reasons people report they hold back or don’t ask is:

  • It will frustrate or bug the person I’m asking.
  • I will use the wrong words.
  • I will embarrass myself or look stupid.
  • I will be told “No.”

This self-monitoring and reluctance to ask prevents us from receiving results well within our grasp. We don’t want to inconvenience others. But actually, the top two reasons people report they say, “No” to requests is when they are approached by someone who:

  • Is asking for something that is inappropriate or I can’t give them.
  • I don’t like, trust or respect.


Vera: One of the strategies you propose is that one ‘shows up powerfully’ when asking – what does that look like in practice?

Linda: Showing up powerfully means you convey confidence. The ability to show up powerfully and command attention develops over time. Here are strategies you can practice- Pretend you are a host at dinner party or a reception, when making presentations, remind yourself the information you are presenting is extremely important, mimic the body language of the most powerful people you know.


Vera: Some hesitate to ask because they might feel they are being too self-centered. What’s the difference between selfishness and self-interest?

Linda: Asking for your interests is simply attempting to get the best deal you can. That’s ok. One possible solution to a reluctance to make personal requests is to consider who else your requests affects or benefits. For example: When you risk asking a question in class, you are helping the other students understand material they might miss. When you speak up in an intimidating board meeting, the answer often helps other members of the group with an important decision. When a client wants you to reduce your reasonable fee for no legitimate reason, you can ask yourself an important question. Do you prefer to donate your time to someone who received value and has the funds to pay you or would you prefer to donate your time to a non-profit who can’t afford you?

There is a benefit to clearly asking for what you desire. You attract more of what you truly value as well as support to help you obtain it. Once you start requesting on behalf of yourself, others start supporting your efforts. If people know you want something and respect you, they go out of their way to help you achieve your goal.


Vera: High stakes requests are your speciality. What’s the best way to handle those in order to increase chances of getting a yes?

Linda: When you approach bigger or high-stakes requests, the preparation is more involved. You think through more stakeholders’ positions or issues. However, don’t let the increased scrutiny and multiple interests overwhelm you. Just break down the big request into smaller ones. Continue to ask questions and take calculated risks. Interestingly, people’s personal attachment to outcomes in high-stakes requests can decrease. For instance, if the request involves a million dollars, a $10,000 variance is not a large concern. In some ways, high-stakes requests are easier because people are more focused on the larger outcome instead of the smaller pieces.

Playing it safe will get you more of what you already have. If you really want your situation to change and become all you can be, you have to ask for something different.  People who are Master Requesters will tell you that really big requests may require some calculated risk-taking and begging for forgiveness after the fact.  


Vera: What role does negotiation play in the “asking process” and how does one know where to focus?

Linda: Asking questions is the language of negotiations. Men and women can be uncomfortable with the term “negotiation.” Call the negotiation process “influencing” or “requesting” instead. You are making a series of requests. You ask questions to identify another’s interests. You provide information to him or her. Together you decide if the requests make sense and you can agree. All the while, you attempt to build or strengthen a relationship.

Focus on WHAT You Really Want. Why waste your efforts over preparing a request that won’t help you?  Name your request, determine your good reasons for pursuing it and describe how you know you’ve reached your outcome. Knowing in advance what you want is the first step in articulating it and achieving it. Before making any request, big or small, ask yourself: What do you want? [Name it], Why? Or what are the good reasons? And is this worth your time and effort? Also consider how the person you are requesting might view your request.


Vera: Let’s say one has asked for something several things and gotten a no. Is there anything one can do to get a ‘yes’ after getting several ‘nos’ from the same person on the same matter?

Linda: Maybe. Maybe not. Wouldn’t it benefit you to find out? The problem is many of us settle for “no” and don’t ask about the good reasons supporting the denial.  If you get a “no,” you can ask about the decision. You can ask, “I’ve heard you say ‘no’ several times can you tell me about that?” or try, “I don’t want to be a pest. I’ve come to you on a number of occasions, can you see anything that would persuade you or help me be better prepared?” Then listen, really listen to their responses without judgement. You may find out you are asking the wrong person or for something they can’t give you. You may be asking at the wrong time. You may need to improve your background, research, support, gain additional buy-in or present your request in a different matter. Or…you may find out that this person would not say “yes” to this request no matter what you presented. All of this information is valuable to help you determine your next best request or path.


Vera: How do you handle the pressure that I assume would come from having to get ‘yeses’ from your request considering you teach others on this?

Linda: People do watch to see if I ask, what I ask for, and the results I receive. Actually, the pressure is more internal. I like to “win” and always think there is a better result. My task is to know when I need to stop wasting time or attempting to maximize and enhance a result that can’t be improved. Like others, I need to remind myself to slow down, take a breath, and remember that my request has probably been asked by others. More often though, asking is a game for me. I like to help people and know that most people like to help others. People can’t help you if you don’t tell them what you want. Making requests is a fun and honest way to connect and form relationships. I continue to be surprised by the amazing results that come when you Ask Outrageously.


Linda’s profile

From the Courtroom to the Boardroom, Linda Swindling, JD, CSP knows firsthand about high stakes communication and influencing decision makers. She began negotiating first as a successful attorney and mediator and later as a keynote speaker, executive coach and strategic consultant. Called ‘One of the country’s top experts on communications’ by the Network for Executive Women, Linda is a past-president of the national speakers Association/North Texas and a TEDxSMU presenter. She is the author of 20 books, including Ask Outrageously, the secret to getting what you really want and stop complainers and energy drainers. More about Linda from


For more information on Vera Ng’oma’s work and resources in leadership, personal and career development and excellence building visit and