Introduction: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!

Linda