The Person You Want to Ask Is Going Through a Rough Time

I had a visit scheduled with a couple who wanted to make a very large gift to an organization where I was working. We had been discussing exactly what they wanted to do, but we had not solidified the exact amount. They needed time to meet with their financial planner and to work out some details with their other philanthropic priorities. When I arrived at their home, only the wife was there, and I assumed the husband would be arriving any minute. We began making some small talk about the summer and the weather, but I noticed she was a bit distracted. Then the telephone rang, and her face looked very distraught. She hung up the telephone and continued our conversation. Something still was not right. I said to her that I had wanted to talk with her and her husband about some ideas I had in mind for their prospective gift, but it was not the right time. I let her know that I sensed she was dealing with something very important and troubling and that we could do this another time. She looked relieved and hugged me as I left, and I told her that our organization was there for whatever we could do to help her with her situation.

Now this may be an obvious case of bad timing, but I do know some people who would have asked for the large gift, specifying the amount and purpose just to get it out and then leave. Some people have the anxiety rush to ask, and then they feel their job is done. How insensitive would it have been if I had asked her right in her moment of distress? The point is to gauge the level of how present the person is when you are about to make your ask. If they seem distracted, aloof, unfocused, or preoccupied, your ask will get lost and will be meaningless. I believe it is always best to say you wanted to share with them an opportunity or wanted to ask them for feedback or help, but it can wait; they come first.

You Are Not Ready or You Are Unsure of Your Ask

The second instance of when you should not ask is when you are unsure of your ask. Let's say during a staff meeting your boss revealed that the company is opening up a new branch and that it would be determining who should lead this upcoming project. This assignment would be perfect for you because you would love to relocate and gain additional managerial responsibilities. You make an appointment to see your boss to ask her if you can be chosen to lead this new project. Your boss asks you why you want the assignment, what three things you will do to make this branch the most profitable in the company, what strategic and critical skills you will share with your new employees, and what partnerships you will form in this new community. You had not prepared for any of these questions, so to ask for the job now would be fruitless. As you will read in Chapter 4, “How to Be an Exceptional Asker,” without preparation, there can be no ask. This illustration highlights the importance of preparing inside and out before you ask. This situation could be saved by stating that the boss's questions were excellent and that you would come back in a few days with answers to those questions and any others she may have, and then you would ask for the job.

Your Ask Will Be Confusing

The third instance of when you should not ask is when you will be confusing the person you are about to ask to the point where they could not possibly make a decision. This happens often when two people are doing the ask. For example, let's say you are a board member and you want to bring a fellow board member with you to ask a colleague to join the board. You sit down with your prospective board member, and you explain the rules and responsibilities (i.e., that all board members need to attend quarterly meetings, they must be assigned to a committee, they must attend special events, and they are expected to make a meaningful annual gift). Your co-asker jumps in and says that while they do want everyone to give each year, not everyone does, and some attend events and some do not. Your prospective board member then has a quizzical look and asks whether she has to give each year and states quite frankly that special events are not her thing, so if she joins the board can she skip the events? Both board members look at each other and say they really don't know, but don't worry something can be worked out. How much a person is obligated to give each year and what the expectations are in terms of participation are very critical pieces of information any board member needs to know before making a major commitment to a board. This illustrates how confusing conversations and unclear facts can muddle well-intended asks. I am by no means suggesting that you need to know every fact and figure before you ask, but you do need to know the important elements of your ask. In this case, the board members should have had a clear and consistent idea of what the roles and responsibilities were for becoming a board member before they ask someone to be a board member. If the person being asked wanted to know some things in addition to the roles and responsibilities involved, that's fine; in fact, it could add to a meaningful conversation.

The bottom line is that if your ask will confuse the person being asked or contradict previous conversations, you must get your facts lined up before you ask. Otherwise you will be spending a lot of time during the ask sorting out the confusion, which really will dilute the impact and power of your ask.

The Quality of Your Life Is Determined by the Quality Questions You Ask Yourself and Others

I must say this is one of my more recent asking mantras, and I just love it! Think about it; questions are so powerful and quality questions are electrifying. Quality questions bring you closer to the person you want to engage. They say to the person, “You are important and meaningful to me and I want to know you better.” Quality questions I like to ask people are:

What is the first memory you had when you knew it was important to give back?

When and if we form this partnership, how do we fulfill each other's expectations?

What does money mean to you? (You knew I would ask that one from Chapter 1.)

If and when you were to do something transformational with us, what would that look like?

When you give us money, where do you think it goes?

What would it take for you to say yes?

Where are we on your top philanthropic priorities?

This is truly so important to us; is it as important to you?

These quality questions invite people to reflect on what is important to them, and it gets very quickly to the heart of the matter—your ask. They enable you to learn so much more about the person that it's like having a window into their soul. You could ask dry and factual questions in a business setting, but it's so much more enriching when you connect personally and build trust and loyalty with your boss, clients, co-workers, family, and friends. That is why you ask quality questions.

The second part of this asking mantra is the questions you ask yourself. Do you challenge yourself enough by asking yourself the right questions? In order to be an extraordinary asker (as you will read in Chapter 4), you have to be prepared to ask yourself the right quality questions:

Am I a good listener?

Do I believe 100 percent in my ask?

Am I giving this person my undivided attention?

Am I present in all my asks?

Am I persistent, not pushy, when I ask?

What did I learn from this experience and how can I use it going forward?

Who can help me navigate this situation?

Do my sincerity and energy shine through when I ask?

I have so many more that I use, but this should give you an idea of the quality questions you can and should ask yourself every day. Here is an example of how this can increase your success, which in turn increases your quality of life. A major food retailer was looking for a consultant to help them form a charitable foundation. They invited me to apply to be their consultant. Before the interview, I asked myself many questions, such as “Why do I want this job?” “Why should they hire me?” What distinguishes me from the pack?” and “What if they make enormous demands that I know I can't deliver?” During the interview they asked me what would be my fee. I share with them that I work on a retainer basis and gave them my retainer fee. One person on the search committee asked me why I thought I was worth my monthly retainer? It was a variation of the question I had prepared to answer but in much less gracious terms. So I thought to myself, “Do they really know who they are asking this question of—an attorney and the expert on the ask?” As you can see, I have a healthy ego, but I thought this question was in really bad taste. I contained myself and thought for a few seconds about my response. To my surprise I turned it around and asked him if he had researched or Googled me prior to the interview? He said he had. Then I said to him, “You already have your answer. You should hire me and at my retainer fee because I am the best and your work requires the best.” Four days later, I got the consulting job. I asked myself the right questions, which mentally prepared me to deliver that answer confidently, not obnoxiously or seemingly unprepared.

Focusing on these questions has put my asking skills on a whole different level, which is why I say it determines your quality of life. It greatly enhanced mine, and I'm counting on it to enhance yours.

When You Ask for Money, You Are Not Taking Something Away; You Are Giving an Opportunity

This asking mantra gets my second vote. I've used this one for over two decades, and it's the one that make people stop and at least give asking for money a try. Many people have told me that when they ask for money they visualize it leaving people's pockets, wallets, bank accounts, and retirement accounts and taking precious resources away from their family, travel, enjoyment, faith, creativity, recreation, health, and education.

Many people have the hardest time asking the people who are closest to them for money. You may want to ask a neighbor to buy a book of raffle tickets for your block association, a co-worker to sponsor you in a race, a colleague to buy a table for your gala, friends to give to your crowdfunding website, or a relative to invest in your business. All of these asks get blanketed with your emotional connection to the person you want to ask. You start to do what I call “fill-in-the-blank fundraising” and leap to assumptions before you even ask. You assume the person will feel awkward and uncomfortable, not want to do it, turn around and ask you for something, or, worse yet, put distance in your relationship. You make all these assumptions, and you haven't even given the person the opportunity to hear what you have to say.

Whenever I hear someone say they can't ask a close friend, relative, neighbor, or colleague for money I change their minds by sharing the following. When you don't ask the people who are closest to you, they think there is a circle of people richer, smarter, better, and more important to you than they are and they are not in that circle. Take a deep breath and re-read that sentence because it is true. I have asked many people who were not asked how they felt when someone they knew very well needed to raise money for either an important cause or a personal project and they were not asked to help out. They felt left out and not important. The worst part is that it makes them feel that they are not rich enough to be asked.

How you ask the people who are closest to you is the key to including them and giving them the opportunity to invest in your cause or in you. Here is how I ask people for money who are close to me, and it has worked successfully for the people who use this approach:

Marty, you know I am on the board of the theater and have been for over eight years. We are celebrating our 50th anniversary with a spectacular retrospect of our top productions on October 15. I have no idea if you are interested in supporting this anniversary celebration but can we have a conversation and talk about it?

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

I select my words very carefully. I lay out what my role is within the organization and why this is important to me and then invite my closest people to join me in the conversation about their possible support. It's one of my favorite asks. Trust me; I learned this from all my mistakes. I am on several boards, and I do a lot of fundraising for them. When I share these fundraising events with my friends and family after they have happened, most of them say to me they would have loved to come or would have loved to have supported it if they had known. What they are really saying is “Why didn't you share this with me before? I would have participated.” What they are really saying is why didn't you ask me? Clearly, I missed the moment to present the opportunity to my friends and family.

Here is another example you can use:

Brittany, while we have been friends since high school and this may seem awkward, I didn't want to exclude you from sharing my excitement about my new virtual-reality sunglasses. We are at the point where we are seeking some strategic investor partners, and I thought of you. I would love to have you involved so can we talk a bit about it and see if you have any interest in investing in our new product?

Again my words are carefully chosen. I get out right away that it may be “awkward” and that I didn't want to “exclude” her. I share with Brittany that the timing is right and that I'm at the point where we need investment partners. If I hadn't selected these words, she might assume I've asked a million people and she was the last one. I use the words “strategic investor partners” because that lets her know it's not just the money we are seeking, it's also her critical and strategic thinking. My ask is an invitation and an opportunity to invest.

THE ASK is an opportunity. It takes nothing away and is filled only with possibilities.

THE ASK Is a Conversation, Not a Confrontation

I have experienced plenty of asks over my career, and the ones that bother me the most are the ones that come across as confrontational. No one ever intends to do that, but it is either the asker's nervousness or overly zealous nature that makes it sound and feel harsh. Here are some examples of what I mean:

Bill, you just have to do it. You know and I know it's the right thing, so that's a yes?

Sarah, I don't need to repeat myself, but you will say yes, right?

Kyle, if you can't do it, we have to close up shop, and you would not want that, would you?

Jennifer, your business partners are in so I don't really have to ask you, do I?”

These examples are not exactly the rapport-building, harmonious relationship building we were looking for during the ask. These may be well-intended asks, but they come off as harsh. I've asked people afterwards who have been asked this way to describe how they felt, and they generally compare it to a tennis match. I speak, you speak, I speak, you speak, back and forth, back and forth. By the end of three rounds of this type of talk the person being asked is completely clueless as to what the person is asking.

So I want you to think of every ask as a conversation. It is circular and inviting. The ask should have a warm tone. It should contain a bit of information you know about the person or their interest, which is directly tied to your ask. For example (and this is an easy one), if you know the person loves to play golf and you are running a charity golf tournament you could say, “I know how much you love golf, and I'm sure your game is much better than mine. I'm helping the club to run a benefit golf tournament that supports children with cancer, and I think you would really enjoy yourself and meet some new business contacts. It's the second Friday in May—might you be interested in playing for a great cause?” Think of what could have been asked using this same example: “It's golf time and I've got just the tournament for you. At the club we have a spectacular day lined up and it has your name all over it. Are you in?” That approach can work for some but when it comes to asking for money, the lighter and more personal touch always wins the day. Even if you know someone inside out, they do like to be asked in a conversational way that gives them the opportunity to ask questions and to make thoughtful decisions.

My advice is that you become aware of the words you select and the manner in which you deliver them when you ask. No one wants to feel as if their back is against the wall, an enormous spotlight is beaming on them, and then they have to make a split-second, on-the-spot decision. Conversational tones, reinforcing the match between the person's interest and your opportunity will get you much further to yes for your ask.