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The Art of Asking: how to get people to say yes to everything you want


Writer Paulette Perhach has mastered a secret art; the art of asking and getting what she really wants as a result. Here she explains how you too can ask for the world - and get the ‘yes’ you want to hear. It's all in the way you frame it...

I’m sitting in a conference room with my boss and the boss’ boss, a no-nonsense kind of guy, and I’m asking for what I really want.

I want to work from home, two days a week, at least. I don’t like offices much. I can’t keep thinking of faces to make the fifth time I pass someone in the hallway. I keep going for raised eyebrows with that nameless, tucked-in smile kind of face.

Plus, I want all the benefits of working from home: yoga pants, cursing at emails out loud instead of under my breath, and bathroom breaks without having to scope out the stalls like a ninja waiting for a lag. I want all those nice things.

No one else in the office really works from home. There is no official policy about working from home. I’m just asking. And he’s saying yes.

I can’t believe it. I got what I wanted. How did that happen?

Truth is: It didn’t just happen. I had studied the art of asking. 

Business meeting

The art of asking is an art I hadn’t known existed until I stumbled upon it. The ask is trying the knob on that door between where you are and where you want to be, to see if it’s locked or not. Increasing your asking skills is like acquiring a set of lock-picking tools for that door.

There are laws, and there are rules, and I’ve found most rules are only human. I got a sense of this young, when I would talk my parents out of punishments and curfews.

I don’t want to be one of those people who thinks the rules don’t apply to them in that ugly kind of way. I don’t cut people in line or steal. I don’t take things from others.

But when there is something I want, and it’s not going to hurt anybody to try to get it, I’m more bold than ever when it comes to asking for it. And I do so using the principles I’ve learned about the art of getting people to say 'Yes'.

Office post-it Yes

So many times we think there is a fence blocking us from that better job, that business deal, or the arrangement we want most with our partners. But I’ve found that when I poke at that fence, it’s usually just an illusion, like the perceived rule that I have to be at the office to work.

The universe is way more malleable than we think. You just have to learn to prod the right spots and in the right way, and it will give.

Here are the rules I’ve learned about the art of asking:

1. Start with why. Your first step is to find the overlap between what you want most and what the person who can give it to you wants most. Make that the basis for your request. In his wonderful TED Talk, Simon Sinek talks about how leaders urge people to act. He says to give them a 'why' behind the plan, a reason for it, and this reason will urge the people you want to say 'Yes' and act in your favor. The why is attached to our emotional core, Sinek says, which is why we should go for the deepest reason first. For my boss, I started with the idea that I wanted to work for the company for a long time. For him then, the why was the benefit of knowing that my position was covered, and they wouldn’t have to replace me.

2. Frame the question in your favour. Even if the person you’re asking stands to lose something, frame the question in a positive way. The way I framed my request was that I would save an hour and a half commute each day I worked from home, and that would make my job more sustainable through the grad school program I was starting (another hint-hint: I won’t quit any time soon). I didn’t highlight that they would lose face-time with me or that I would miss meetings. I kept it positive and focused on what they stood to gain from it.

3. Anticipate and answer their exceptions before they have a chance to bring them up. People don’t like change in general, and usually when you’re asking for something, it’s going to involve a change. I assured the big boss that I would be available at all times for phone calls and that I would answer emails within two hours. I guaranteed him that I would come in for any emergencies. If you leave the askee with no more questions or objections, they might find no reason not to say yes.

4. Start with the small yes and grow to the big yes. When people say yes to something, they like to stick with that answer. So you can get a small yes, and keep extrapolating, which is something sales people do all the time. For example, if you’re asking to work from home a few days a week, you can ask your boss: You believe in work-life balance, right? If he or she says yes, you can keep going from there.

5. Cite trusted sources. People can argue with you, but it’s harder to argue with research, statistics, and Harvard professors. I didn’t need this for my pitch, but I had at the ready Daniel Pink’s research on results-only work environments, and my record of sales. I prepared like a lawyer making a case, ready to do so as needed.

Asking for what I wanted scared me at first, but as I worked in the quiet of my apartment, with a great mix of alone time to focus and strategising time at work, I realised my life had moved a few degrees toward the one I really want.

Asking had been worth it, and learning how to ask had made all the difference.

It’s not that all you have to do is ask. All you have to do is ask well.

The books that can help you get what you want

If you have a serious ask you want to make, for a raise, for a new arrangement with your partner, or for a business deal, here are some books that can help you get what you want:

Book shelf

Influence: This book was written by Robert B. Cialdini, a man who kept saying yes to things he didn’t even want. He found out how people got him to say yes, and used those tricks to help the reader be more convincing.

Fierce Conversations: Asking is made of conversations, and Susan Scott here teaches you seven principles to guide each one toward what you want.

The 4-Hour Workweek: Tim Ferriss dares you to ask for a lot: freedom, time, and a life bursting with experience. This book was the one that inspired me to ask to work from home.

Start with Why: Simon Sinek’s book on how to get people to follow your lead and say yes passionately to your ideas.

The Art of Asking: Amanda Palmer talks about trusting your own life’s purpose enough to go after it and let people help you get there. 



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