1. The Fear of Rejection and of Hearing No.

Hopefully, you have enough tools shared in this chapter to arm you against feeling rejected or dejected and you can use this as an opportunity to ask again in the future.

2. You Are Not 100 percent Committed to Your Ask.

A local group that was organizing a 5-k run asked me to come in for the day to speak with their volunteers. There were about 30 volunteers in this session, and they were responsible for asking their friends, family, colleagues, and anyone in their network to sponsor the run at a $250, $500, or $1,000 level. Before I began, I asked them to tell me why they got involved with this group. Many said because a friend asked them to help raise money for the race. Then I asked them what they knew about this group. Many said something very vague like “They do good work” or “It's a good cause.” So I asked them how strong and persuasive do they think their ask will be if they are not 100 percent committed to the mission of this organization? They looked at me with blank stares, and many looked down or looked away. My last and final question to them was “Could this be the reason why they have yet to ask their friends, their family, their colleagues, or their network?”

Whenever you ask, you should be 100 percent committed—all in, with absolute certainty that this is what you want for your organization, your business, your personal growth, and your happiness. When people sense that you are not 100 percent committed, they will very rarely say yes to your ask. I have an expression that has served me well over the years: “When you ask, people see right through you.” They can tell, sense, and read whether you are or are not passionate, committed, convincing, and energetic about your ask. Please do not think you can disguise this, because you cannot. I have been with people who did their best to disguise their discomfort or their detachment with their ask, and it all fell apart. Be the one who is 100 percent committed, own your ask, and watch the response.

3. The Dreaded Quid pro Quo, That You Will Be Asked for Money in Return.

This one is an easy one to overcome. Will you be asked for money if you ask for money? Maybe you will, or maybe you will not. When you are in that situation where someone asks you for money back, you have choices. You can either support or invest in what they are asking or not. But this should not prevent you from pre-selecting who you ask if you really want to ask a person but sense she may ask you back in return. Again, this leaping assumption that if you ask them, they will ask you (so as a result you do not ask at all) is entirely made up in your head. It is an assumption you have created. You may be leaving a lot of money on the proverbial table if you don't ask or choose to ask only the “safer” people who you sense will not ask you back.

Additionally, remember, those people who are closest to you know what you do and that you have to raise money. To leave them out of your asking possibilities distances them. Unless a friend, relative, colleague, or neighbor tells you “please do not ask me for money,” you have nothing to lose and everything to gain. Revisit Chapter 2, “Asking Mantras,” for examples of how you can ask with sensitivity so that you feel good about asking those people closest to you, even if you sense they may ask you in return.

4. The Awkward and Uncomfortable Situation that Results from Asking Your Spouse or Partner for Something Personal.

I am purposely focusing on the personal ask with someone you love because this can be incredibly difficult. There is a lot at stake, because you may put distance into the relationship when you ask for something that is personal and important to you. I know many couples who struggle with getting more time for each other. Life and work get in the way of their time as a couple. If both parties are not on the same page as to how much time is the right time to spend with each other, arguments begin. Worse yet is when one person feels that he or she is spending the right amount of time with the partner and life is just fine, while the other partner is stewing and building resentment to the point of feeling abandoned and taken for granted.

What prevents the ask in personal relationships? First, we all want to have our conversations be nice and loving. When you ask for something that may surprise the other person, or if you don't know whether the other person feels the same way, that's a risk. When it's a risk, we retreat and we don't ask. Second, many times there is an expectation that, since you are so close, the person should do what you want without asking. How often have you heard the questions “Do I really have to ask for it? Shouldn't you know what to do?” The problem with expectations is that they go unspoken. In the example of our couple where one is happy and content with their shared time while the other is building resentment about the lack of shared time, the unhappy partner expects their special one to naturally know that they need more time and to just make it happen.

Without the ask, it does not happen and will not happen. This can all be resolved in a gentle and caring way if the unhappy partner says,

I miss when we do not spend the weekend and a weeknight or two just for ourselves, and I hope you do. Our time together keeps me so close to you and I feel so empty when we do not share that quality time. Can we talk about how we together can work on making that happen?

5. You Don't Know What Amount to Ask.

This can be particularly difficult to determine, and I have seen this more times than I care to in philanthropy. A new potential supporter is identified for the nonprofit. She becomes educated and involved with the organization's mission. After she expresses great interest in helping the organization, it is time to ask her for money. Suddenly, because the development person does not have absolute certainty about what this new prospect can give, even if massive amounts of prospect research have been done previously, the development person postpones the ask. It also happens quite often when entrepreneurs need backers, investors for the business.

When you are in this situation of not knowing how much to ask for try using these words:

Emily, you graciously shared with us that your primary interest in our elementary school is that the children have field trips to cultural events in our city. We have no idea if you can make a gift of this size, but we ask you now to consider making a gift of $50,000 that will cover the costs of two field trips a year for every child in our elementary school. What do you think about this amazing opportunity?

Kyle, I've set up a crowdfunding site for my new business because I'm seeking to raise the remaining $20,000. I have no idea if you could make an investment of this size, but I would love for you to make the first gift on the site for $5,000 so that others will join you and make similar investments of this size. How does that sound to you?

In the example with Emily, it is important that if you know what the person is most interested in with your organization you reference that in your ask. That is what I call “the match.” It matches the person's key interest with an opportunity for your organization or business. In the example with Kyle, it is also a good idea to let the person know that their investment will attract others to give in similar amounts. That is a real multiplier effect. People are often hesitant to give if they think they will be the only one giving. When you say that their investment will attract other investments, that wakes them up and suddenly they are with you in your effort to raise money.

For both of the examples above, I use the phrase “I have no idea if you can make a gift/investment of this size.” If you really do not know, this is a great phrase to use because it is honest. It also keeps the ask in focus. By that I mean you are showcasing and placing the emphasis on the project or program to be funded, not the amount. During your ask, you should make sure the person is really interested in your project or program before you ask for the money to fund it. Suppose in the preceding examples I had said,

Emily, we really need $50,000 in order to give our elementary school children access to three field trips a year.

Kyle, $5,000 will jumpstart my crowdfunding effort. Can you do it?

Do you see the difference between leading and focusing on the amount and not the importance of the projects? When you place all the emphasis on the amount, the person being asked detaches and feels that they are just being asked for their money, not their involvement.

6. You Don't Know Who Should Make the Ask.

Instead of focusing on who should make the ask, flip this around. With each ask, think of the person you are about to ask. The asker then needs to be someone the person knows, likes, and trusts. That's my rule. People feel really comfortable if they are asked by someone they know, like, and trust. The ask does not go well at all if a complete stranger makes it, if the person being asked does not like the asker, or the if the asker is not trustworthy. Every ask requires strategy, so when you are lining up people you would like to ask, consider each person one by one and think of who would be the best person to make the ask. If it is someone besides you or in addition to you, then make sure that person is brought into the process early. For example, if you want to bring on a new board member, committee member, or volunteer and you believe that a fellow board member should do the ask with you, then from the first meeting make sure that board member is with you.

Asks go very badly when a brand-new person is brought in to make the ask. I know this firsthand. I was working with a donor who wanted to make a very large gift to the university. I got to know this donor and his family very well over the course of seven months. We had discussed the parameters of his gift: when he could make it as well as what portion of the gift would come from his liquid assets and what portion from his will. The day arrived when he was scheduled to come to my office so that we could go over the details of his gift and he could sign the gift agreement. A person in a leadership role at the university who knew the donor only slightly called me one hour before my meeting and said that he had called the donor. The donor was coming to his office, so I should deliver the gift agreement to his office but not be part of the meeting. At first I thought this would be great since it is always impressive when a person in a leadership position is involved in high-end asks. Then I got this very uneasy feeling because I did not know what the relationship was between these two men. I asked if I could be part of the meeting, just to listen and to do any follow-up that was needed. The answer was no. (That is an ask right there—asking to be part of an important meeting.)

The meeting took place without me. About one hour after the meeting I received a telephone call from the donor. He was irate, upset, and angry. He told me the university would never receive a dime from him. To this day, I have no idea what happened. Could I have changed the results if I had been in the room? I may never know. The one thing I did learn and I do know now is that it is really important to apply the know, like, and trust, rule when selecting the asker.

7. You Don't Know When to Ask.

I often say if I had a quarter for every time a person asked me “How do I know the person is ready to be asked?” I would own Manhattan! I have an expression and it really applies here: People leave clues; we miss every one of them.

Take this scenario: You are explaining and outlining your project or something you need with a friend. Your friend turns to you and says, “What do you need to make this happen?” “What do you need from me?” or “How can I help you?” Nine times out of ten you keep explaining your need and skip right over this clue. The clue is that they are asking you to ask them for what you want. If you want money, this is the time to ask for it. If you want help, this is the time to ask for it. If you want advice or a referral, this is the time to ask for it. So become that superior listener, and the time to ask will become obvious.

What if you do not receive these questions and you are still unsure. I have two more tips for you. First, let your instincts be your guide. If you feel the person is ready to be asked, do it. This is what we call the gut test. There is not a whole lot to explain because it is something you have to feel. This requires you to be really focused and present in your conversations and interactions with the person you will eventually ask.

Second, whenever I am stuck and really do not know, I create structure. Years ago I created “Laura's readiness formula.” I have used this as a guide to judge whether a person is ready to be asked so here we go:

A person needs to be educated and to have a certain level of knowledge about your ask. Think about yourself. Would you willingly do something if you did not know anything about it? Probably not. Next, the person needs to be a bit involved. This naturally varies from person to person, but my rule is that the larger the ask, the more involvement is needed. If you need a relative to take care of your children while you are having surgery and recovering for a few months, that relative really needs to be involved. He will need to know your children's schedules, what they eat, when they sleep, what after-school activities they do, what they like to do in their free time, and how many hours they are allowed on their smartphones and video games.

The hardest part of this formula is inclination. Visualize a playground with a seesaw that right now is perfectly level. If you think the person is inclined to be asked and your instincts say the person is inclined, then you need to ask and the seesaw goes up. If you think the person needs more information or has not given you any signs that they really can focus on your ask, then the see-saw goes down. If you are really stuck and it could go either way, here is one of my favorite questions to ask; I call it my “inclination test:”

Laura, when and if you were ready to [fill this in: invest with us, make a transformational gift, join our team, have the discussion with your mother-in-law about drawing up a will, ask your teenager to get a job, or explore alternative care with your doctor] what would that look like?

I love this question because it resolves the inclination question along with so much more. The first part is using the person's name or title. When anyone hears their name they wake up, and now it is time to move quickly to get to the transformational question. The second part is when and if. That expression lets the person know that you are interested in their timing. If they respond, “I have no idea, I haven't given it any thought” the person needs more education; so you go back and provide more information. If the person says, “Gee, I always thought I would do x,” then you know the person is ready because they have been giving this much thought.

The third part is your ask without sounding like an ask. In the preceding example—“when and if you were ready to invest with us”—in essence you made the ask: Invest with us. Now all you have to do is fill in the level of the investment and you have your ask. The fourth part, “What would that look like?” gets the person to visualize. The very words “look like” give the person the opportunity to visually imagine what that investment would look like.

The fifth part of this formula is assets. If your ask is for money, you should have some idea that the person can give you money. Again, as stated in item 5 regarding the reasons people do not like to ask, if you think the person can support you but you don't know the exact amount, take the first ask opportunity and say “I have no idea if you can do this” and then state the specific amount. If the person has previously shared with you that they have invested x amount with another company or person, then you should be pretty certain that they can make the same level or larger with you.

8. You Have Never Given the Size Amount You Need to Ask.

There was a time when we used a very old fundraising rule: You could not ask for an amount if you had not already given that exact amount. For example, if you were asking for $100,000, then you yourself needed to have given $100,000. While this was an admirable rule, it quickly faded because many volunteers in leadership positions could not make the size gift or investment that the organization needed. So here is the way I resolve this issue. Anyone can ask for an amount that is much larger than what they could do if they ask the right way. The word to use is stretch, and this is how it is used:

Bill, I've made a stretch investment with the company, and I hope you will join me with an investment of x.

Casey, I've made a stretch gift to this organization that I love, and I hope you will join me with a gift of x.

Even if the person asks you the exact amount that you gave or invested, you can look them in the eye and be perfectly honest. Your amount was a stretch for you. By that I mean that you gave or invested with an amount that was larger than you originally thought possible. It tells them and shows them your commitment to the ask.

9. The Person You Want to Ask Gets Asked All the Time.

We call this “tripping over the big fish.” Every town, every region, every state, every nation has them—the known philanthropists and investors that people line up to approach. Remember when people discovered that Bill and Melinda Gates and Warren Buffet had money to give and invest? Practically every nonprofit requested a grant, and every company wanted to align with them. Next came the big start-ups in Silicon Valley who found themselves being showered with requests to be honored at a gala or given an award. Now, it's any successful entrepreneur. But let's say you want to approach one of these high-profile people because they may be a good fit for your ask. I believe honesty wins the day. I would be right up front and say:

Ms. Wonderful, we know you get many, many requests, but we truly believe we have an opportunity that is perfectly aligned with your key interests. We do not take lightly that we may be a long shot to get your attention and consideration but we promise it will be well worth your time. Would you be willing to meet with us for 15 minutes?

THE ASK—it's two sentences and a question.

10. The Presumption that the Person You Are Asking Does Not Have That Kind of Money.

Presumptions can kill us! Before we even pick up the telephone or send an e-mail or text, we are off to the races in our minds that the person we want to ask doesn't really have that kind of money so why bother. This is what I call the presumptive projection. It happens most frequently in two situations: (1) we want to ask the people we are close to but protect them from being asked if we sense they may not have the assets and, (2) we make a quick judgment about the person's ability to give money without having a conversation.

For the people who are close, we project that it is not good to ask them for money now. Perhaps their children are in expensive private schools, someone lost their job, their father needs to be placed in a nursing home, a child needs to go to boarding school, or they have been rejected for additional health insurance. Or we may read that a person we want to engage and ask just got a divorce, their company has laid off 100 employees, or he or she has invested heavily elsewhere.

When you find yourself in this situation, very honestly ask yourself this question: “Are the facts deterring you, or are you projecting that if you were in these situations you would not want to give or invest?” The projection comes and starts with you. You instantly put yourself in their shoes; in essence you become them and then you make decisions for them with that person having never been asked!

Again it is how you ask with all the sensitivity in the world that makes this all possible. My suggestion, and it has worked for me, is to say:

Leslie, I cannot imagine what you are going through right now; your strength is beyond comprehensible. I've been working on/involved with a few projects that, even though the time might not be ideal, I think you would really want to be involved with at some level. If this is not a good time, please let me know; otherwise may I have the opportunity to share this with you?

11. The Surprise Response that Will Catch You Off Guard.

Will you be caught off guard when you ask? Of course you will, time and time again. That is part of the asking learning process. The more responses you hear, the better your asks become. In Chapter 4, we will go into great depth about how you can prepare for all the responses you may hear and how to respond. As a teaser, here is a story about one of my craziest responses and how I addressed it.

I was in charge of a very large capital campaign. When the time was right, we had a meeting with a trustee whom everyone loved and admired. He had been a trustee for over a decade. When we asked for a $2 million gift to help kick off the success of the campaign, an amount that matched exactly what he wanted to fund for the campaign, he put his hands behind his head, slid down the seat, and said, “What makes you think I have that kind of money?” I was blown away. What do you say to that? We all knew each other so well. The person who did the ask with me was someone our trustee knew, liked, and trusted. What one could have said was, “Well, we've researched you over these years and we know you have the assets,” but that is not what you want to say. Instead, I said, “We have no idea if you can do this size investment, but you know you are the one everyone looks up to and admires to make this campaign a success.” He left abruptly, and we thought this $2 million gift opportunity would never happen. Three days later he called me and said, “I'm in.”

The moral of the story is to make your ask regardless of the response you think you will hear. Every response is a moment to perfect your ask.

12. Knowing the Exact Words You Should Use When Making an Ask.

I have to admit I struggled with this many times. You meet people you want to ask, and in your head you keep hearing “But I know they want to hear certain words” and you can't find them so you don't ask. Well, I'm here to tell you there are no magic words, but there are words you can use that will mirror their tempo and sensibility and will resonate with the person you're asking. In Chapter 5 I will synthesize this for you. It is all about active listening and selecting words you are comfortable with using and that you feel will resonate with the person you wish to ask.

13. The Possibility that the Person Will Give You in Time What You Want without Asking for It.

I call this the ask without the ask. Then I tell everyone that the ask without the ask will result in no money or tremendous disappointment that you did not get what you wanted. This happens in three situations: (1) you feel so close to the person that you believe they will naturally know what you want and do it; (2) you overthink every angle of the ask and so much time goes by that it will miraculously come up at some point in your conversation; and (3) you have engaged and cultivated the person so much that your actions are your way of asking. Avoid all three of these mindsets and activities at all costs.

You do more harm than good when you assume, procrastinate, or overextend yourself in activities without speaking about your ask. You send mixed messages when you do these things and they totally confuse the person. I was with an attorney who was doing very well at his firm but, naturally, wanted more clients. So during a reception I asked him how things were going. He said really well; he had just booked a country club for the day, invited all his present clients, and “they never put their hand in their wallet” the entire time. I said that's terrific and then asked him if he had the chance to chat with them one on one to ask them to send him some people who may need his services. He looked at me quite surprised and said, “I didn't need to. They got the message.” Months later I spoke with him and asked him how many new clients he had gotten from that event? I think you know the ending of this story without me telling you: none. So I coached him to remember one unique thing about each person or something they said and then call them and say,

Thanks so much for your valuable time at the club. I recalled that you (something unique about them/something they said) mentioned your daughter was visiting college campuses—my niece is doing the same thing. Can we get together and compare notes? I'd love another perspective on this important decision.

Then at the meeting, once the attorney had established a stronger rapport with each prospective client, I told him to share a short story about the work he does and then ask for the business. Don't leave the ask to chance or think time or actions will fill in for your ask.

14. You Asked This Person Before. It Did Not Go Well, but You Have a New Project that Is Perfect for Them.

What I like about this situation is the determination. Imagine that you asked someone for something and it did not go well, but you want to go back with another idea. Bravo! Here is an example of taking on this kind of risk but getting great results. A Broadway producer was in my class, and when it came time for the role playing with an ask he needed to do, I said OK, cue up the class. He said that he had asked a wealthy businesswoman who loved theater and that she had invested in two previous plays and both times the plays had a short run and closed. Her investments never yielded a return. He was working on a new play and he was most certain that the theme of the play would resonate with her core principles that she shared with him many times.

I must say he did an amazing role-play ask. He first told her she had every right to be disappointed in the past plays and he was very grateful to have her precious time. Next he outlined in one sentence the theme of the play and with tremendous enthusiasm stated that it matched her most important values and beliefs. Last and for the grand finale, he asked her for a $20 million investment and said that he wanted her as his key partner.

You now see how two sentences and a question can even be applied when you have the urge to win someone over; explain the past, state that it is a perfect match because you listened carefully to the person's values, and then make the bold ask. So what did our lady investor say? She said she would give him $10 million to start and that he better not blow this one. When and if she was convinced the play would do well, she might give more.

If you truly feel that you have a wonderful opportunity for someone but they either have turned you down before or were unsatisfied with previous results from prior asks, do make the ask. My caveat is to be on your guard not to overexplain the past or exaggerate the new offer.

15. The Person You Want to Ask Is a Much Better Asker than You.

I was consulting with a very well-known nonprofit, and one of our prospects was a very well-known hedge-fund owner and philanthropist. He had never made a gift to this organization, but we have heard from several reliable sources that he loved our mission. I wanted the president or a trustee of the organization to make the call and see our hedge-fund prospect, but they wanted someone on the staff to see him first and determine whether he was really interested. If he was interested, they would follow up. From the start I did not think this was the best approach, because I believe that in this instance and someone of this stature, you may only get one chance to see. Be that as it may, it was my job to prepare a staff member to get the appointment with him. She was terrified. He had a reputation of being very unpredictable in meetings and worst yet, he was a superior asker. You don't get to be in his shoes without asking and winning at the game.

We worked on what the staff person would say if she had a 15-minute meeting, a 20-minute meeting, or a 30-minute meeting. I felt like I was back at the attorney general's office practicing my oral argument at the Court of Appeals for the Third Circuit. You stand in front of a podium with three lights on it—green, amber, and red. The moment the red light comes on you are dismissed, and any word you utter will not be considered part of your argument. What terrified my staff person the most was that our hedge-fund man would know she was there to eventually get money from him. She also worried that he would press her into a corner and demand she make the ask. So we practiced that many times over.

She did get the meeting and it did last 15 minutes. There was no small talk at all. He told her to get right to it, so she made the ask and she did it well. He turned her down immediately, and barely made eye contact with her as he was focused on some documents on his desk. He said he had people who could do the same thing we were asking for at a 10th of the price. She countered that he had the first shot, and since he was turning it down, this project was so important to the organization that we would turn to other supporters. Well that got him. He demanded to know the names, and she refused for confidentiality purposes. She closed with saying he and his company would have been perfect for this gift, and if he changed his mind to let her know within the week. I was so proud of her, and she felt like, well, $15 million bucks, our ask price. Later, we were fortunate enough to meet a person who loved the project and agreed to fund the costs. We heard that our hedge-fund man was furious. I have to admit we were silently happy when we heard that news.

Even if you know or have heard that the person you want to ask is a better asker, ask anyway. You will always walk away with more self-esteem because you did it, and I guarantee it will be quite the learning experience.

So there you have it, 15 reasons why people do not ask but now you know how to overcome each one if and when they should arise. You have nothing to lose and everything to gain. Don't let one of these reasons stand in the way of your happiness and your success.