Ask Outrageously!

The Secret to Getting What You Really Want

Linda Swindling (Author)

Publication date: 06/05/2017

Ask Outrageously!
Stop Holding Yourself Back—It's Time to Go Ask!

The strongest relationships, top sales groups, and most successful organizations have one thing in common: people who have the courage to ask outrageously. This doesn't mean being obnoxious or taking advantage of people. It means not compromising, taking a risk to get what you know you need, not what you think you can get.

Based on Linda Swindling's original research and her experience helping people make high-stakes requests in everything from business negotiations to marriage proposals, this book offers proven approaches to improve your asking and boost your chances of success. Whether you are a professional looking for a bigger opportunity, an entrepreneur striving to build a company, a nonprofit seeking funding, or simply a parent or friend wanting a more fulfilling relationship, it's time to make that big ask! Get ready. Your results will surpass your greatest expectations!

Read more and meet author below

Read An Excerpt


(member price: $17.06)
Free shipping on all orders from the BK Publishers store.
Or find a local bookseller with Indiebound.

Additional Links:

Hire Linda Swindling

Other Available Formats and Editions


(member price: $13.27)


(member price: $13.27)
Bulk Discounts
Rights Information

Featured Books

The Economics of Higher Purpose

Two distinguished scholars offer eight steps to help organizations discover and embrace an authentic higher purpose—something that will dramatically improve every...

Feedback (and Other Dirty Words)

A practical and irreverent guide to taking the sting out of feedback and reclaiming it as a motivating, empowering experience for...

How to Be an Inclusive Leader

We know why diversity is important, but how do we drive real change at work? Diversity and inclusion expert Jennifer Brown...

More About This Product


Stop Holding Yourself Back—It's Time to Go Ask!

The strongest relationships, top sales groups, and most successful organizations have one thing in common: people who have the courage to ask outrageously. This doesn't mean being obnoxious or taking advantage of people. It means not compromising, taking a risk to get what you know you need, not what you think you can get.

Based on Linda Swindling's original research and her experience helping people make high-stakes requests in everything from business negotiations to marriage proposals, this book offers proven approaches to improve your asking and boost your chances of success. Whether you are a professional looking for a bigger opportunity, an entrepreneur striving to build a company, a nonprofit seeking funding, or simply a parent or friend wanting a more fulfilling relationship, it's time to make that big ask! Get ready. Your results will surpass your greatest expectations!

Back to Top ↑

Meet the Author

Visit Author Page - Linda Swindling

Linda Swindling, JD, is a recovering attorney, speaker, executive coach, author, and strategic consultant. She is a Certified Speaking Professional and president of Journey On, a speaking and consulting company. Her TEDx Talk, Why the World Needs You to Ask Outrageously, is scheduled for November 2016.

Back to Top ↑

Table of Contents

Introduction: Ask Outrageously! 1

How to Get Outrageous Results from This Book 11
Define “Outrageous”
No Difficulties Asking? Why You Still Need This Book

Assessment: How Well Do You Ask? 18

1 Proof You Should Ask Outrageously 19
What's Difficult about Asking
Top Ten Reasons to Ask Outrageously

2 Show Up Powerfully 31
Identify Your Strengths Strategies to Convey Confidence

3 The Right Focus 45
Why You Need to Get Over Yourself Prepare to Ask Boldly

4 What's in It for Them? 53
Easy Asks
The Importance of Timing

5 Trust and Respect 71
Manners Matter
“What” and “How” Questions

6 Ask Everywhere—All the Time 93
Talk to Strangers
Raises and Promotions

7 Blocks 113
The ASK Strategy How to Banish Blocks

8 Asking for Others 127
Self-Interest versus Selfishness Wintegrity

9 Authority 139
Dealing with Decision Makers
You Need Help—and How to Get It

10 Tailor Your Ask 153
The DEAL Strategy
Your Communication Bias

11 Calm under Pressure 175
Out of the Ordinary Requests Ask Away or Walk Away

12 Outrageous Results 197
High-Stakes Requests
Best Practices of Master Requesters

A Final Note 209

Resources: Secret Success Tools 211

Acknowledgments 217

Index 223

About the Author 227

Back to Top ↑


Ask Outrageously


Ask Outrageously!

Can you keep a secret?

If you don’t have what you really want in your life right now, you probably haven’t asked or you are settling for less than what is available.

Want to know more?

The number of opportunities you miss concerns me. From my experience and research, I know you overlook possibilities well within your reach. When you make requests, you overprepare and focus on areas that don’t get results or a yes. Despite your preparation, experience, and ability, you ignore what matters most.

Want proof?

Examine the recent research. More than a thousand people (1,163 to be accurate) from a wide variety of professions participated in our Ask Outrageously Study. They revealed what prevents them from asking for what they want and the areas in which they weren’t effective when asking. Their responses uncovered major flaws in what we request and how we ask. The data spotlighted big misunderstandings about why people say no. One reason I wanted to write this book was to break these misperceptions and shed light on why your efforts don’t work. I also wanted to let you know that you are not alone. According to our study, 80 percent of us say that we could enhance our results by improving how we ask. The remaining 20 percent say that they ask effectively. Many of their responses imply they wonder why the others do not ask when given the opportunity.

What’s the bottom line?

You stop yourself from making better requests and getting better results. From my experience, backed by our research, I can tell you that you are getting in your own way. Instead, you need to feel the fear—and then ask anyway.

Be the first to ask.

Imagine sitting in the studio audience of The Tonight Show with then-host Jay Leno. Jay comes out before the taping and asks for questions from the audience. Surprisingly, he picks you to ask him a question first. This happened to me. I had two questions: first, I asked about his job, and then I was going to ask for a picture with him on the stage.

Jay responded to my first question. Before I could ask for my picture, he turned and answered another woman’s question. She asked for what I really wanted, a picture with him. As she made her way to the stage, Jay turned back at me. He said, “That’s what you wanted to ask for, isn’t it? A picture.” I nodded and started rising from my chair. He gestured for me to stay seated. Shaking his head, he said words I’ll never forget: “Sorry. You didn’t ask. She did.”

Thinking about that day still gives me a sinking feeling. Instead of asking for what I really wanted first, I delayed and put unnecessary effort into finding out information I didn’t need. I’m not alone in failing to ask for what I really wanted. Our study showed that one-third of people wanted to ask for something big but didn’t. They waited to ask for a raise, a promotion, moving expenses, and even spending money in college. Later, they saw someone else get what they wanted. Like me, they thought about making that request, but didn’t follow through or waited to get more information.

Do your own asking.

When our daughter, Taylor, was four, we took her to a school carnival. There she spotted the face-painting booth and told us, “I want my face painted. I want a butterfly.” My husband, Gregg, said, “Great. Here’s a ticket. Go ask them for what you want. Your mom and I will wait.” Taylor had a different idea. She wanted us to ask the booth volunteers for her. After much protesting and pleading on her part, my husband bent down. He looked her straight in the eye and told her, “Mommy and I don’t want our faces painted. We don’t want a butterfly. You do. If you want your face painted, you have to ask. We’ll be here watching. You will be OK.”

Reluctantly, Taylor walked over to the booth. When her face was painted, she skipped back to us. Taylor was happy about her purple and pink butterfly and proud of herself for asking. She spent the rest of the night asking for what she wanted at other booths. Although it would have been easy for us to ask on her behalf, our preschooler learned a valuable lesson that many adults struggle with: you have to do your own asking.

Asking is not a task to be delegated or avoided. You can’t wait for someone to recognize that you deserve better or to speak for you. When I practiced law, I strongly negotiated and made requests for others. Rarely, though, did I ask for what I needed or really wanted. Although I acted in the best interests of my clients, my attempts to avoid looking greedy or self-absorbed were not in my best interest. Honestly, people would have been delighted to help me if I had asked. My clients received great results. However, my failure to ask blocked me from possibilities that were appropriate and attainable for me.

Ask outside your comfort zone.

My first months in law school were miserable. Those days, I questioned my intelligence and decision to attend. Worse, I sat in classrooms with other students who appeared to understand the lectures. Many of my peers would nod intelligently. A few offered comments to show their grasp of the material.

My classroom strategy was different from that of those confident legal scholars. My plan was to hide my ignorance, avoid drawing attention to myself, and hope the professors didn’t call on me to answer questions.

There was additional pressure to stay silent. Some of my peers reacted negatively to a student brave enough to ask “stupid” questions. This elite group would smirk. They rolled their eyes and shook their heads at the student’s ignorance. The condescending looks created a chilling effect. Each day, I was afraid of professional embarrassment before I was a legal professional. So I hid, took copious notes, and prayed for enlightenment that never came.

One day in my contracts class I felt particularly frustrated and confused. After an internal debate, I decided it would be more expensive and embarrassing to fail law school than to ask a question. Timidly, I raised my hand and asked our professor about the concept of “promissory estoppel.”

Guess what? He was happy to answer. He said it was “a fairly common question.” With his explanation, the concept wasn’t confusing at all. After a month of sitting silently, avoiding eye contact, and feeling intimidated, asking a question finally helped me grasp a legal concept. Understanding was a tremendous relief. The results of stretching outside my comfort zone outweighed the embarrassment. A few professors became mentors once they saw I was interested in understanding the law. Surprisingly, I formed friendships with other confused classmates and several upper-level students. As an added benefit, I found that upper-classmen can tell you about professors and share notes from their first year.

Yes, comments and jokes were made regarding my “stupid” questions and lack of intelligence. Know what? None of those snickering students had the power to give me a grade, grant me an internship, or pay my bills. Once unleashed, I began asking all the time. Outrageously, I asked two famous authors to attend receptions at our law school and speak for free when they came to our university. Guess what? Both feminist Gloria Steinem and Sarah Weddington, a former member of the Texas House of Representatives, agreed to my request. Asking questions and being vulnerable helped me make better grades, rank higher in my class, and land a job when I completed law school.

How does a preschooler’s reluctance to approach a carnival booth or a law student’s fear of asking questions relate to you? Turns out the answer is plenty. Asking outrageously feels intimidating and uncomfortable to the person making the request. Many of us stop ourselves before asking because the request doesn’t feel safe. We are concerned about what others think of us or how prepared we are.

You don’t know what you don’t know.

Elaine Morris, the business coach I hired to help me grow my law practice, asked me a question years ago. “We’ve doubled your revenue. You spend more time with your family, yet you still don’t seem happy. If you could do more of anything, without worrying about money, what would it be?” I answered that I loved presenting at conferences and the training I did for free. She replied, “You know, people get paid good money for that, right?” No, I didn’t. I thought only teachers and professors were paid to teach. I figured the rest of the experts spoke for free to get more clients. Elaine sent me to the National Speakers Association. There, I met several professionals who had transitioned from other areas of business including law and now made a living by presenting, writing, and speaking.

How can you know someone’s answer to a question you haven’t asked?

Don’t assume you know their answer.

Years ago, I called a publisher to complain about a leadership program. I was transferred several times and finally was forwarded to “a leader who would be able to help fix my issue.” After resolving the issue, he asked why a lawyer was interested in a leadership and communication program. During our conversation, we discussed my transition from practicing law to creating executive development programs. Before we hung up, I “outrageously” asked if he ever needed new authors.

Let’s be clear. The request wasn’t inappropriate or rude. However, it was outrageous for me because it was outside my concept of the norm. Asking the editor of a publishing house is not the traditional way books are submitted for consideration. I know you’re not supposed to call up an editor and propose a book. There is a format to submit a proposal. And yet I asked even though I knew better.

Your comfort zone does not define how someone will respond to your request. My request was simply another question to the editor. Yet this outrageous ask gave me an outrageous outcome. This one request led to a published book and then several others. That conversation and the relationships that resulted from that one request became key to launching an executive development company and my professional speaking career twenty years ago. Imagine the power you could have if you felt the fear and asked anyway, without worrying or questioning yourself.

Be courageous.

The fearless have no problem asking. Our son, Parker, has always been a master at making requests. Once, while waiting at a restaurant, we turned around to find him missing. A few frantic minutes later, we saw him sitting in the restaurant eating pizza with a family who had a boy his age. When we went to reclaim our son, we asked how the two boys knew each other. School? Church? Scouts? “Nope.” The mom laughed. “We just met Parker. He asked if he could join us and told us he was hungry.”

As an adult and accountant-to-be, Parker continues his fearless requests. He asked his wife, Victoria, to marry him at a concert. More precisely, he asked her in the middle of the concert … by singing a solo to her … from the stage … in front of a packed auditorium, including several of his friends and a live-streamed audience. There’s more to his outrageous request. A few days prior to the event, he asked the conductor and the band if he could interrupt their concert and propose by singing his favorite song. Oh, and could they learn the music to accompany him? Thankfully, the outcome was good. The band agreed. And she said yes.

Do you know people who ask all the time, without hesitation? Watch them. They may be young children who wear you down with their questions until you say yes. Maybe they are friends, a significant other, or a salesperson. Perhaps they run their own businesses, are decision makers in associations, work as service providers, or request funds on behalf of non-profit organizations. They regularly ask outside most people’s comfort zone, and they often get what they want.

Remember to ask.

Conducting the research for this book required an outrageous ask from me. It was ten days before the meeting with the publisher and two weeks before my TEDxSMU talk on this topic. During both presentations, I was presenting the final findings of our Ask Outrageously Study. The problem was that we hadn’t reached our goal of 800 research responses. After three months, 562 participants had given us great suggestions, but that total fell short of the sampling size I wanted. Unlike the past two studies for books I had written, this survey was not gaining ground and time was running out.

Finally, I posted my issue in a social media group. Putting all pride aside, I asked my female speaking colleagues what actions they would take to hit the 800 goal. And I confessed I had only a short time frame. Can you guess what question they asked me?

Yep. They wanted to know, “Have you just asked?” Honestly, my answer was no. Consider the irony for a moment. I was speaking and writing about how to ask outrageously, yet I hadn’t asked others for help. My friends told me what I tell others: ask people directly for their help. Don’t try to provide information and value first. Lose the fluff. Don’t hide the request. Instead, just ask for what you really want.

In a matter of minutes, one of my speaking friends had drafted a sample request for me. She told me to tag friends and ask them to tag ten of their friends. Even though I didn’t want to bother people and I felt uncomfortable asking, I took a breath and posted my request. And then I witnessed the power of asking outrageously in action. Within days we hit the 800 mark and then unbelievably 1,000. A week later, we closed down the study with 1,163. My being a little vulnerable and asking more than doubled the results.

For years, I’ve watched myself, my clients, and people I love fail to ask or settle for less than we wanted. So, I started probing and did the research.

I wrote this book on how to ask outrageously because:

  • I was curious and furious that the people I care about often go overlooked and unrewarded for their efforts and talents. I wanted to correct misconceptions about why their requests don’t get a positive response and to help them focus on what really matters.
  • I wanted to acknowledge those who taught me the power of being courageous, outrageous, and stretching outside my comfort zone. I also needed reminding of the power that comes from being vulnerable and asking for help.
  • I wished that this book had existed years ago for me to read. Knowing how to request without reservation would have saved me thousands of dollars. The energy I spent could have been used in much more productive ways. Asking outrageously would have helped me avoid years of uncertainty, self-doubt, and the headaches resulting from trial and error.
  • I learned through the years that leaders, mentors, and coaches want to help people they lead. They care about people’s growth and development and about achieving success. (Outrageous Request Alert : How much more effective could your people be if they understood how to ask? What would be possible if you gave a copy of this book to all those you manage and influence?)
  • I hope the strategies and insights will shortcut your learning. It’s important to know you can dramatically improve your ability to make requests. Also, I know you can influence not only your situation but create opportunities for others in a way only you can.

Ask Outrageously


Proof You Should Ask Outrageously

There is magic in asking. The people with the best results are those who have the courage to feel the fear and ask anyway. They win more by being willing to push the envelope. They learn to ask for a little more and explore possibilities. They become more comfortable with taking risks and even hearing no.

People in history—from politicians to rock stars to Nobel Peace Prize winners—have had great success making outrageous requests. Having the courage to ask creates unbelievable results. A simple request can challenge injustice in the name of human dignity, generate significant medical advancements, create new ways of doing business, and impact communities. Consider these historic requests.

Rosa Parks asked, “Why do I have to sit at the back of the bus?” and her request led to changing racial segregation laws to protect the rights of all citizens regardless of race.

Louis Pasteur asked, “What causes wine to sour?”—a request that led to the discovery of how to destroy bacteria, which evolved into pasteurization technology to keep food safe. Mary-Ellis Bunim and Jonathan Murray asked MTV, “Can we create an unscripted television show that follows the life of strangers in a house?” The result led to The Real World and the genre of reality TV. (Arguably, some results are more notable than others.)

Outrageous Outcomes

There is a snowball effect when you begin to ask outrageously. What may be a simple request often grows into several requests. Asking can evolve into negotiations involving bigger stakes than you thought possible.

Want a secret only those who make high-stakes requests know? Asking outrageously feels the same, no matter the dollar amount or the consequences. The adrenaline rush, the fear, the excitement, the quickening heartbeat, the change in breathing, and the concentrated attention feel the same. And people who ask outrageously receive unbelievable results in all areas of their lives. Often, the most meaningful outcomes are personal ones.

After years of no communication, I called my son and apologized. I asked if we could start over. He let me speak to my grandson for the first time. My grandson is four years old.

I asked my boyfriend when he thought we should get married. He proposed the next week. He had paid for the ring six months ago but didn’t think I was ready and was waiting.

I asked my parents if I could borrow the money to make a down payment on a house. Instead of loaning it to me, they gave me the money. They had wanted to help me but didn’t know how. I’d still be living in an apartment if I hadn’t asked.

Other outrageous outcomes begin with requests that are business related:

I asked my partners if they were willing to expand by opening an office in San Antonio or Austin. They agreed and we opened offices in both cities.

After seventeen years of thinking about it, I approached physicians in other medical practices. I asked if they were interested in how we handled our back office and our methods for collecting payments. That request led to an entirely new business, which has generated millions of dollars.

In the past, a supplier and I did a lot of business together, but we had a falling out. I went to her booth on the trade show floor and asked if we could put our grievances aside and do business again. We just filled our largest order yet.

During a break in the negotiations seminar, I went into the hall and made a call to ask for a reduction in our medical equipment rental fees. We now are paying 30 percent less for the same equipment. I locked down the price for the next three years, and it only took one phone call.

What’s Difficult about Asking?

More than 96 percent of those surveyed said they could have improved their results by asking for a little bit more or by taking more of a risk (see Figure 2). Almost a third said they could have increased their results by at least 50 percent. According to the study, the top reasons people hold back or don’t ask are:

  • I 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 .
  • 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 you from receiving results well within your grasp. And “overwhelm or bug the person I’m asking” ranks as significantly more difficult than “be told no.” Seems odd, right? People would rather be told no than feel they are bothering someone to get what they want.

The Ask Outrageously Study reveals people are worried about the wrong things. For instance, people think their requests are denied because:

  • The other person lacks all the information needed.
  • The timing is wrong.
  • The person I’m asking doesn’t want to spend the money.

Actually, the top two reasons people report saying no when approached are that the person making the request:

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

News flash: We are focusing on the wrong things. The research shows that there is no correlation between why people say no and why people think they are told no. Most people don’t know the true reasons that their requests have been denied.

The primary reason people say no is when a person “is asking for something inappropriate” (with 36 percent reporting it as the primary reason). However, when given the opportunity to select “inappropriate” as a reason their requests are denied, only 4 percent of people thought it was the answer. (See Figure 4.)

To further support this disparity, 31 percent of respondents report saying no if they “don’t like, trust, or respect” the person making the request. However, only 5 percent of people think that they’re told no because the people they’ve asked “don’t like or respect me.”

The study also showed 79 percent of people feel more confident and prepared when they have all the information needed.

What a tremendous disconnect between perception and reality! What good is preparing with all the information needed when you are asking the wrong person for the wrong thing? How does all that research data help when the person you ask doesn’t like, respect, or trust you?

What are the consequences of not asking?

Not getting what you want or living with outcomes determined by someone else is draining. Patiently waiting for someone to recognize your talents or give you a break is frustrating for you and those around you. You miss out when you don’t ask. Do any of these situations seem familiar?

You’ve seen a promotion or your dream job handed to someone without your credentials or experience.

A coworker is given opportunities to travel or be involved in a project you would love to do.

You decide a person is too popular or good-looking to date someone like you. And that person ends up dating one of your nerdy friends.

A friend receives a better hotel room or an upgraded airplane seat. You took what you were assigned.

Someone else makes a major life decision for you without consulting you.

Not making requests works to your disadvantage in other ways too. When you repeatedly consider making a request and fail to ask, you send the message that you are satisfied. You signal that you’re not ready to move forward right now. It’s like preparing for a journey and stopping just steps away from your destination. Here’s what some of the survey respondents said about their reluctance to ask.

  • I wish I had the courage, but being told no cripples me.
  • Ninety percent of the time I’d rather go without than to ask for a favor.
  • I was taught to be happy with what I have.

By not following through with your request, you never know for sure what is possible. And the people with authority to grant or deny your request have no idea of your preparation or desire to have something different. By not asking, you’ve removed that person’s chance to consider your request and give you an answer.

Asking is a brave act.

What if you were brave?

Asking outrageously requires vulnerability and giving up some control. Sometimes you have to risk looking stupid or hearing the word “no.” The best results come from minimizing the unknowns, structuring the elements you can control, and then simply having the courage to make your request.

If you are worn out from thinking about requests you don’t make, tired of just accepting what you are given, and ready to improve your results, you might want to try asking for what you really do want.

Top Ten Reasons to Ask Outrageously

  1. Shockingly good outcomes. It’s not unusual for people to ask for something they feel is outrageous and then report the person on the receiving end wasn’t shocked at all by the request. Often the person asked is delighted to help or wondered why the request wasn’t made sooner.
  2. Evidence of passion. When you clearly show your interest, it is contagious. People will know you are engaged and invested in getting better results. By asking, you indicate that you know what you want, are ready for a change, and want to achieve big goals.
  3. Powerful appearance. People who make bold requests improve their chances of being heard. By asking powerful questions, you improve your ability to influence and show confidence, no matter what the subject.
  4. Receive an answer. By asking, you obtain a reply, even if it’s “no” or “not yet.” With an answer to your request, you can adjust, adapt, and move ahead. You can save time, resources, and mental effort. Most importantly, you stop wondering what could be if only you had the courage to ask.
  5. Build trust. When you request what you want up front, people stop searching for your hidden agenda. Others want to help you more because they trust you more.
  6. Level the playing field. Asking questions helps decrease any real or perceived power imbalances. Instead of accepting what is presented, asking questions lets people know you do your homework and are prepared to debate if needed.
  7. Avoid wasting time. Asking allows you to avoid spending time with the wrong people. You’ll quickly determine who can and will assist you in achieving the outcomes you want.
  8. Receive more than requested. When you find the courage to ask outside your comfort zone, you discover the limitations you imagined aren’t always real. Asking allows you to maximize the possibilities and gives you more options.
  9. Feel fantastic. Perhaps the most remarkable result is how people feel after they ask. When you feel the fear and ask anyway, you gain confidence and a greater sense of worth.
  10. Earn respect. People enjoy dealing with others who encourage them to think bigger. People with high potential want leadership models who successfully take risks, impact others, make effective decisions, and exceed expectations.

Make Asking a Habit

Condition yourself to ask outside your comfort zone on a regular basis. Start with safe requests. Ask for more in your personal life and watch your results improve in business too. And get comfortable with the word “no.” In fact, if you are not hearing no, you are probably not asking for enough. Keep asking until you get the no.

When you concentrate on making requests as a habit, asking becomes second nature. If you can become more comfortable asking everywhere, you’ll ask when it really counts. In the heat of a big request, you will achieve results others can’t conceive at the time. Stay open to receiving results that surpass your greatest expectations.

Lead Others to Ask

Ask the people you are leading or coaching to take the free assessment “How Well Do You Ask?” (page 18) or online at Review the results of their assessment and the Top Ten Reasons to Ask Outrageously (page 26). Ask them, “Where would you like to focus on asking for more?” “What reasons resonated the most with you?” and “What results would be possible if asking became a habit?”

Outrageous Review

Simple questions in history have led to outrageous outcomes.

Most people don’t ask. They wish they had the nerve to ask for something big but don’t ask or settle for something safe. They wait too long to ask and watch someone else ask and get what they really wanted. They feel stuck when it is time to move on or advance.

There is a disconnect between why people think they are told no and why they are actually told no. The success of your request is not just about gathering more information, timing, and funds.

Your precise word choice, fear of bothering someone, or looking foolish should not be your primary concerns.

Improve your outcomes by focusing on the real reasons people are told no, which are 1) the request is inappropriate; and 2) the person being asked doesn’t like, respect, or trust the person making the request.

You can increase your wins and improve your results by asking outside your comfort zone. When you concentrate on making requests as a habit, asking becomes second nature.

Smart Asks

  • What would I ask for if I were brave?
  • What am I unsatisfied with at work or home?
  • When I fail to ask, what message am I sending?
  • How can I develop trust and respect from the person I’m asking?

Ask Asks

  • If you haven’t taken the assessment “How Well Do You Ask?” (page 18 ), please take it now. Then look at the results to determine your current skill level.
  • Look through the “Top Ten Reasons to Ask Outrageously” (page 26 ). Identify the top two reasons that resonate with you.

Look through the “Top Ten Reasons to Ask Outrageously” (page 26). Identify the top two reasons that resonate with you.

Secret Success Tools

Download the song “If I Were Brave” by Jana Stanfield and Jimmy Scott for free at

Ask Outrageously


Show Up Powerfully

Knowing how others view you is important when making powerful requests. Your family and your friends know the “real” you. However, when you are asking others, there is a good chance you are meeting for the first time.

A few brave souls can ask confidently without assigning much significance to being turned down or how others think of them. One out of five of the study participants reported they have no difficulties asking anyone for what they want. Here are some of their responses to asking outrageously.

  • I have no problem asking for what I want in a business setting … most people will answer anything I ask, even if it doesn’t pertain to the specific request.
  • The worst response you can get is a no, so why not ask?
  • I know to start asking questions even if I’m not sure what the right question is. Opening the dialogue often takes me in unexpected directions and to answers I didn’t know I wanted.

Master Requesters

You may live with a courageous asker. Often, family members, even very young ones, are convincing and tenacious. Think of children who really want a toy or a treat. Their ability to connect, stay the course, and ask questions is entertaining. The word “no” doesn’t intimidate them. They concentrate on what they want and are persistent in their pursuit. Master requesters know requests are situational and can vary depending on the people and issues involved. They consider the best methods to relate to the person who has power and change their approach as needed. They are curious and very creative in asking an unlimited supply of questions. And they are successful more often than not.

Without reservation, they ask for a little more. They ask for better terms or greater outcomes. Observe them as they ask for information, favors, or special treatment. No one intimidates them. No request is too small or too large. They know the more they ask, the more they can learn or gain. While others are gathering unnecessary data or waiting for perfect conditions, master requesters make an initial request and move on to ask elsewhere.

Often their success in business can be tied to a willingness to ask for what others won’t. They are respected. People are willing to answer their questions and go the extra mile to help them. Study the masters. Watch people who bravely make requests and follow their lead.

How do you show up?

When you meet a stranger, what would be his or her initial impression of you? Your initial impression goes beyond how stylishly you’re dressed or if your hair looks great that day. Do you portray confidence, trust, and approachability? Master requesters know exactly how they show up the first time. Through the years, they have listened to feedback and observed techniques that work. These masters recognize when they appear intimidating and take action to lighten the conversation. They know if they seem young or inexperienced, and they choose whether to correct or use that perception. They make a conscious effort to be approachable and to help others feel comfortable.


Approachability goes beyond professional attire and a well-groomed look. An approachable person:

  • Smiles and makes eye contact.
  • Has a firm handshake and is polite.
  • Helps others feel comfortable and heard.
  • Develops an engaging presentation style.
  • Consciously uses positive body language.
  • Uses proper grammar, spelling, and language.
  • Responds in a timely manner to emails, phone calls, and other communication.

First impressions are made in thirty seconds or less. Spend more than thirty seconds getting ready for them.


Nona’s legal assistant scheduled an appointment with a new client. When business owner Bob Smith arrives for his appointment, Nona greets him warmly: “Hi, Mr. Smith. I’m Nona. Welcome. Let’s go back to the conference room.” Confused, Bob looks at Nona and asks, “Are you going to take me to see the employment attorney?” Nona smiles and laughingly responds, “Here I am.” Bob, not smiling, says gruffly, “Young lady, I’m here about a serious business matter. I need to see someone with experience.”

Nona may have some cultural biases working against her. She is a woman in what some consider a man’s field and appears young. Nona didn’t add to her credibility with her lighthearted introduction. She created the impression she was subservient by addressing Bob formally and introducing herself using only her first name. Bob may therefore doubt whether she has the required knowledge and experience to handle his issue.

To salvage this meeting, Nona isn’t disrespectful, but she is assertive. “Bob, I have practiced law for six years. I am a partner and no one has more experience with employment matters at our firm. However, we do have lawyers who are older. If you prefer, we have an attorney in the office that is twenty years older than I am. While he doesn’t have a background in employment law, he did pass the bar a few months ago. Which of us would you like to speak with today?” Bob wisely choses Nona; and Nona learned a big lesson in first impressions.

When you know you don’t look the part, be strategic and know your stuff.


Joe Solinski is successful asking potential clients to become immediate clients. “First impressions are important. I give prospects a history of our twenty-year-old company so they know we have the experience and expertise to do anything they need to get their properties in order.” A seasoned presenter, Joe translates complicated situations into easily understood language for the non-engineering executives. He interjects humor to break the ice. Joe uses photographs to show his firm’s creative solutions to challenging and complex construction problems.

Also a competitive bodybuilder and musician/singer, Joe is aware his appearance can be inconsistent with more conservative expectations. “I know I have long hair and don’t look like most owners of commercial consulting firms, and that is certainly my choice. I have to be who I am in order to be the best I can be for our clients.” Joe adds, “The most stern and challenging clients in the initial meetings are usually the ones that remain clients for life.”

Identify Your Strengths

Understanding the strengths you bring to the table is one of the first ways to increase your power when asking. People downplay their gifts and natural abilities. If you are approachable and naturally friendly, you may not count those traits as talents or strengths. Or if your gift is to understand complexities and numbers, you may wish for better presentation skills. Being well rounded is overrated. Being an expert at what you do well is how you get the most compensation. Concentrate on those strengths and develop them.

Own Your Strengths

Determine two of your strengths and use them in a conversation with others at least three times. Here are some ideas you can use to fill in the blanks.

  • My job here is to ____________ and _____________.
  • I really enjoy ______________ and ______________.
  • People depend on me to ________ and ___________.
  • Example: My job here is to think logically and to check our quality.


Think back. Have you been told you have a talent that you know you’ve never developed? For instance, has someone told you that you are confident or good at organizing? How did you respond to that compliment? Did you thank the person or internally question his or her observation? Maybe you know others, even relatives, who you think are much better at that skill. That person doesn’t know that your big brother is the really confident one in the family or that your dad is the neat freak. People’s evaluations of you are based on their experience of the community as a whole. The people who are complimenting you just know you.

Identify Your Strengths and Talents

Look through the following list of characteristics or qualities. This is a small sampling of strengths and talents you may possess. Decide which apply to you.

  • Adapt to change
  • Analyze
  • Coach
  • Communicate
  • Connect with others
  • Contribute to a team
  • Create
  • Explain
  • Facilitate discussions
  • Influence others
  • Initiate
  • Innovate
  • Lead
  • Listen
  • Make decisions
  • Manage projects
  • Manage risk
  • Negotiate
  • Present
  • Resolve conflict
  • Set goals and strategy
  • Solve problems
  • Support systems
  • Troubleshoot
  • Understand technical issues
  • Others: ____________________________________

If people recognize a strength that would be helpful for you to possess, decide to adopt it. Start by observing people who have developed that talent and model your behavior after theirs. Use the language they use to ask and respond to questions. Observe how they manage stress or react when surprised. Ask yourself, “What would they request in this situation?” Then just ask as they would.

If others are spotting a talent or characteristic, there is a strong likelihood you have it. Find ways to strengthen and develop those gifts.


Have you heard words used to describe you that make you cringe? Before you try to eliminate or change that behavior, pause. Often, strengths that were undeveloped behavior when you were younger become valuable assets when you are older. Being bossy as a child can morph into being a leader who makes impactful decisions. The class clown becomes a master storyteller and marketing expert. The child who cries too easily grows into an empathetic adult with an intuition about angry customers or the best way to serve disaster victims. The youngster who took apart everything to see how it worked becomes an engineer or a business strategist.

Instead of dismissing a trait of yours, decide how that description could be upgraded or adapted to serve you better. When would that quality be great to have? What training do you need to make it a superpower? Watch strong people who use their similar characteristics or power for good. Adapt the positive aspects of the trait to serve you better. Rein in the less desirable aspects and upgrade the beneficial behavior. Keep those stronger descriptions in mind when you make requests.