The Art of the Ask

Why Asking for Things is an Essential Skill You Should Master


Sam McKenzie

3 years ago | 7 min read

As a professional fundraiser, I have to be good at asking for things.

But asking for things is an important skill that everyone needs to be successful. Too many people are afraid to ask for the things they need. This can hold you back, and it opens the door for those who may not be as talented or qualified as you but aren’t afraid to ask.

Just like anything, there are basic strategies that you can use to perform a stronger, better ask that is more likely to get a yes.

Getting Over the Fear

The first step to asking is getting over the fear that prevents you from doing so.

Asking is taking a risk — that the other person might say no. And if they say no, what might they be thinking about you as a person for asking?

That’s what can be scary to people about asking for things, that people might think less of you for putting yourself in that position. Which is actually ridiculous, because everyone needs to ask for something at some point. We all need help.

Just as they say the most successful people fail the most often, the best askers get the most no’s. Being nervous before an ask is normal. Most people are, at least a little bit. While being nervous is ok, being so afraid of asking that you don’t do it will cripple your chances to accomplish what you want.

It really is about mind state. You have to tell yourself that people aren’t saying no to you, they’re saying no to your request. If you asked them something else, they would have said yes.

In Daniel Pink’s amazing book, To Sell Is Human, Pink suggests that before you go into a pitch you ask yourself, “Can I do this?” Provided you are prepared, your brain will begin thinking about all the ways you are prepared, which is a good thought exercise before you go into the meeting as well as boosting your confidence.

Engage and Inspire

This is the fun part. Assuming you are passionate about whatever you want (and if you are not, now is a good time to ask yourself why you are doing this), you now get to transfer that passion to another person.

If you don’t know the person you are asking, the best thing way to start is to find out as much as you can about them. You can do this through conversation, through online research, or asking mutual acquaintances.

If you have the opportunity to talk to someone before you ask them for what you want, start by asking them questions about themselves, where their passions lie, what is important to them, and where their pain points are. Think about how you align and can add value.

Once you have engaged them and found out more about their interests, use what you have learned to inspire them. Share how you will move the needle in the direction of your mutual interests. Talk about the big picture and be ambitious about where you want to end up.

Then, connect it all back to the person you are speaking to. Make it clear that, through their support, you can be one step (maybe a huge step) closer to achieving that ambition.

Your goal is to get the person revved up and excited about what you are doing. The best answer for them to emerge with is, “How can I help?”

Make sure you are always sharing how you will add value, how you will follow up, and what is in it for them.

The person you are asking needs to feel like your relationship is a two-way street-they are contributing, but also getting something in return.

Creating a Yes Environment

As a fundraiser, few moments are more rewarding than when a prospective donor does the ask themselves.

That sounds crazy, but it actually does happen sometimes. Someone will say, “Ok, how much do you need?” before you even ask them for money. Or they’ll say, “Sounds great. I’ll donate $XXX”.

This happens when you’ve created the perfect yes environment. When everything you say and do conveys your purpose and passion and the other person feels it and gets inspired. It’s a beautiful thing.

It’s difficult to manufacture a moment like that, and you can’t predict when it will happen. But there are a few things you can do to create the environment where it might happen. At worst, by setting the right environment you will improve your chances of getting a yes when you do the ask.

To set the right environment, you need to convey a clear sense of purpose, build trust and rapport, and properly set the other person’s sights. It’s possible to do all of this the first time you are meeting someone, although it’s not easy.

To convey a clear sense of purpose, you need to be knowledgeable and clear about what you are talking about. Meaning you can explain exactly what your goals are, what you are doing to achieve them, and where you need help.

Trust and rapport are the foundation of any successful relationship. There’s been so much written on it — if you haven’t read How to Win Friends and Influence People, that’s a great place to start.

But basically, people trust people who they think are like them. They like people who take an interest in the things that interest them.

Some people will lie to accomplish this. This is where the stereotype of the sleazy car salesman comes from, the guy who will say anything to make a sale. Don’t be that guy.

Instead, embrace the fact that we are all human and there is not a person on this planet with whom you don’t have something in common. Find that thing.

Once you’ve built trust and established a purpose, you need to set the other person’s sights. They shouldn’t be shocked when you tell them what you’re asking for.

Be Transparent about Your Intentions

Although it’s related to being clear about your purpose, it’s worth stressing that creating a yes environment requires transparency. No one wants to feel they are being manipulated.

Even when you ask for the meeting, let the person know you intend to ask them for something. That doesn’t mean you do the ask before you have the meeting. For example, if you’re planning on asking your boss for a raise, say something like, “Hey John, I’d love to meet with you to get some feedback on my job performance, to share some ways I think that I can continue to add value and to ask for your support. Do you have 20 minutes on the 30 th?”

Be honest about your intentions and let the other person make a decision — do their objectives align with yours? And if so, to what extent?

You’re looking for people who are all in to what you are doing, and to find that out you need your intentions to be completely understood.

How to Make the Ask

After you’ve laid all of the groundwork by engaging, informing, inspiring with a clear vision, strategy and need for support, all that’s left to do is make the ask.

Keep being clear about your intentions, including that you are about to make an ask. Sometimes, I like to say, “I’m going to let you know what I’m asking for”, or something similar. Usually the person will pay close attention at that point and allow you to say what you’re going to say.

By the time you are going into the ask, you should have already made your case and given the person a sense of what you are looking for. You should have a gotten a sense of how they feel about you and your goals. There should be no more surprises.

Cut straight to the point, look the person in the eye, and make your ask in 2–3 sentences.

Say something like, “As we discussed, over the last two years I have fully achieved my goals. We also agree that I have developed as a leader by taking on additional projects and responsibilities, and if I continue to do so it will be a value add to the company. I feel great about this and would like to ask for a 10% raise to acknowledge my past performance and my increasing responsibilities.”

Then, remain quiet and maintain eye contact until they answer. It’s important to say nothing. If they don’t answer right away the instinct is to say something qualifying, either making your case again or, even worse, lowering your ask amount. This will only weaken your case, whereas saying nothing and keeping the silence will put the pressure on the other person to respond.

The next thing they say might not be an answer. They might ask more questions, or they may tell you they need time to consider it or ask that more detailed information be sent to them for review. Regardless, the person who was asked should always be the first person to speak after the ask.

After the Ask

Asking can be a numbers game — the more you ask, the more people say yes, but also the more people say no. You have to find ways of dealing with rejection because it will happen sometimes. But it doesn’t have to be a bad thing.

Daniel Pink asserts that the best salespeople have an “optimistic explanatory style”, meaning they blame outcomes on temporary conditions rather than permanent ones. In other words, if you ask someone for a donation and they say no, it’s helpful to chalk it up to a specific circumstance (e.g. they don’t have the money right now) rather than a universal one (e.g. that person doesn’t like me).

The more you ask, the less scary it is. Do whatever you have to do to get through the first asks — your palms will be sweaty; you will be nervous and holding your breath. Breathe, open your mouth and get it out.

Even if they say no, asking someone is a win. When you ask, you’ve just taken one step towards achieving your goal.

If you ask in a deliberate, courageous, and thoughtful way, you will have the respect of your audience no matter what the outcome is. If they say no, smile and thank them anyway. Always be classy.

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Sam McKenzie







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