The Power Of Ask


I was afraid to ask my boss for a raise. I was afraid to ask my girlfriend to move out. I was afraid to ask Claudia to marry me. I was afraid to ask Dick Costolo to write the foreword of “Choose Yourself!”

I’m always afraid to ask people for favors. Or to do something that would benefit me.

So this was the magic technique, in the first two scenarios above: I quit my job (maybe my boss would counteroffer). I moved to another city rather than ask her to move out.

He did counter-offer and I stayed. We did remain broken up because it’s hard to maintain a relationship in different cities.

I don’t know if this counts as “asking for something” but it was certainly an “aggressive-passive-aggressive” way to ask for what I really wanted.

I have this tendency to think of myself as a “giver”. Even a “super-giver”. But it’s not true. Sometimes I have to ask. We all live in a society where it’s just as important to ask as it is to give.

It almost makes me feel like a fraud when I have to ask for something.

When I was in tenth grade I asked Nadine to go out with me. I think she dropped one of her books when she ran away. I took it as a good sign that she didn’t give an instant “no” but just ran instead.

I was impressed with how athletic she was. The way she darted in and around the swarm of teenagers who were at this point all looking at me.

People pray and ask God for things. This is too easy. He doesn’t answer and only in movies does he give any sort of sign. And you have about 50-50 odds of getting what you ask for, give or take.

One time when I was selling a company I started, I felt I was not entitled to ask for something unless I lied.

For instance, a potential buyer asked me why I wanted to sell.

I said, “Because I think my company is now at a level where it can grow really fast if partnered with a bigger company.”

HA! What a load of BS. I came up with that one on the fly.

But what if I had just said, “I want to make a lot of money and I want you to give it to me.” The only real answer. Then what? He didn’t buy my company anyway.

It’s like talking to a girl at a bar. Something I’ve never been able to successfully do. There’s an entire cottage industry of pickup lines that supposedly “work”.

I hate to say it: but I’m pretty sure none of those lines work. In part, because I’ve used many of them. And in part, because people aren’t like robots. There’s no buttons to press and then the robot comes to life.

A woman pretty much knows what you want when you go up to her in a bar. Even if you ask nicely, you’re just asking for one thing, no matter what vomit comes out of your mouth and into her face.

So I decided to make a catalog of what “Asks”s work and what doesn’t. You’re welcome to share more types of Ask if you want.


Like, if I want something from Claudia but I’m afraid to say it. There’s a slight chance that if I’m COMPLETELY SILENT for 48-72 hours then she might guess what I want and then do it.

This technique will ruin your life.


This is maybe even worst than the Passive Aggressive Ask. First off, people say “it doesn’t hurt to ask” precisely when it does hurt to ask.

You’ve just given them a problem. Now, if they say “no” they feel like a bad guy. And if they say “yes” they will hate you and you will end up not getting what you wanted.

One time someone wanted to guest-post on my blog. He said, “it doesn’t hurt to ask”.

I have never had a guest post on my blog and suggested he would be even better off if he went to a blog that regularly had guest bloggers.

He ended up writing an entire post about what a jerk I was. So it did hurt to ask. It didn’t hurt me. But it hurt him because it ruins his ability to ask me (or other people) anything in the future.

Often when you do the totally unprepared Ask thinking, “it can’t hurt” then not only will the person look down on you (hurt), but you also slander yourself (hurt) and ruin your chances of later Asks or friendship or whatever.

Only do the “It doesn’t hurt to ask” technique if you’re ready for a 95% chance of “no” and you’re actually willing to be hurt.

This leads to:


If you’re willing to handle lots of Nos, then ask a lot of people. This is like cold calling. Or asking everyone on the street to have sex with you. Eventually, unless you are me in both the above scenarios, someone will say “yes”.

In fact, it’s good practice to do this Cold Ask in situations where

a) you don’t really care about the person you are asking or what they think of you. “it doesn’t hurt”

b) you are asking for something trivially small.

The “cold ask” is a useful technique for another purpose – to practice breaking out of your comfort zone.

It’s a useful exercise, for instance, to go to a distant mall, stand by an escalator, and ask everyone coming down if they will have coffee with you.

This is a good way to break out of the shy comfort zone that so many of us deal with every day. You won’t be shy if you do this. I’ve done it and it works.


You would think begging is the worst. I’ve tried it.

I went down to Wall Street once. I wore a suit. I asked everyone going into the New York Stock Exchange if they would give me $5.

Nobody gave me five dollars. One guy got very upset. He said, “no” to me and left and then he came back and said, “what is this for” and he raised his arm as if he was going to hit me.

The wrong place to threaten violence is on Wall Street. There’s about 5000 police and guard dogs there. So I wasn’t worried.

I asked about 100 people for $5. One guy gave me money. He had $1. He gave it to me. He was a homeless guy sitting against a wall.

Another guy gave me a hot dog.

So begging works.

Why does begging work? Because you’re actually giving something to the person you are asking.

What are you giving? Status over you.

If I ask Claudia to see the movie “Superbad” for the tenth time and she says no and I say, “PLEASE! PLEASE! COME ON!” then she knows she will gain some status over me if she says “yes” and that she can cash that status at some later point.

For the homeless person on Wall Street, who is so used to having his status trampled on, I gave him a chance to have status over me and he was happy.

But for the person who responds to a Begging Ask, don’t forget that Status inflates like a dollar. Over time it becomes worthless so you have to use it while you still can. Remember that, Claudia!


This ask is pretty bad. If you do this for me, then I’ll do X for you later. It’s almost like begging but with everything clearly outlined in advance.

You would think, this seems fair, it’s like bartering.

No it isn’t. It’s more like a bad negotiation where the side being asked is at an unfair disadvantage since he has no time to evaluate the value of what is being bartered.

Since abstract things are hard to value on the spot, one side will end up feeling ripped off. Usually the side being Asked.

So you are actually insulting the person you are asking. It won’t work.


Now we’re starting to get into some decent ask techniques.

If you can truly convey that there’s no pressure on them saying “yes” or “no” then you preserve the relationship if they say “no”.

In fact, in some cases you even make it better.

1) You show that you respect the person’s right to say No

2) You can follow up with later No Pressure Asks and even deepen the relationship.

This worked well for me, for instance, when I wanted to sell a company, was told “No” and then was able to follow up with monthly updates for over a year before they got interested again.

In fact, I’ve probably used this technique successfully on many important occasions. It even works in online dating. You stay in the “online friend zone” until lightning strikes. Actually, that’s never worked for me but I hear that it does.

It’s hard to convey “No pressure”. Because there’s always a tiny bit of pressure.

One way to do a no-pressure Ask is to ask for advice.

For instance, I can ask a buyer, “What would you do if you were me and you wanted to sell your company?”.

Or you can ask a client, “What else would you recommend I do to improve my presentation to ANY client so that I could potentially ask for more business.”

This is really no pressure. They don’t have to respond. Or, they can feel pleased that you give them status (status they rightly deserve) and respect their status so much that you aren’t directly asking.

It’s like they are the sun and you can’t stare straight at them. That’s the no-pressure Ask.

Often a response in the “no pressure ask” results in you getting more business from the client. They feel flattered and they instantly want to help you.


This is the Hare Krishna technique mentioned in Robert Cialdini’s book.

When the Hare Krishnas asked for money, they would get nothing but NOs.

But when they gave a little flower first, they got billions.

Once you give something in advance, the brain naturally wants to give back and show that it is a good member of the herd.

But here’s the trick: if you ask immediately, then I personally think it’s a little too slimy. Like the Hare Krishna trick.

The key is to do a “Give” and then forget about it. And then a month, a year, a decade later, come back with the “Ask”.

A Give creates potential energy in the future. An Ask turns the Potential energy into Kinetic energy.

I hope I’m getting that physics analogy right.

Create as much potential energy as possible every day with many Gives. Store up your Asks for when you need them.


This is THE most powerful ASK and almost always works. Particularly when combined with the “NO PRESSURE” Ask.

A few months ago I flew to visit Amazon and visited many of their departments where they showed me what they were working on.

If I had just called them and said, “I want you to spend your whole day showing me what you are doing” I would never have gotten a response.

Instead I spent a long amount of time thinking of good ideas I could build or they could build that would help them with one aspect of their business. If they were bad ideas, or if I didn’t put the time in, they never would’ve responded.

I gave them value. And I said, “No pressure on responding. These are now your ideas for free.”

A few months later the head of business development called me and invited me to visit. Which I was happy to do. I spent the day at Amazon and then saw the very first Starbucks.

It was a simple ask but it involved about ten hours of work on my part plus a lot of experience dealing with subtleties in the Amazon experience.

So maybe about 100 hours worth of work to ask to visit Amazon’s headquarters and learn how I can publish books better.

If you want someone to spend one hour of their life helping you, then you need to spend 10 hours of your life, at least, helping them IN ADVANCE and with NO PRESSURE.

Every ASK that has created immense value in my life, even millions of dollars, was a result of me doing ten times the amount of work first, for free, before I got the door even slightly open.

_ _ _

If you are like me, you feel like you have to give and never ask. Or you feel afraid to ask. Or you are shy to ask. I am shy to the point that sometimes I even cry, I’m so nervous before I ask for a favor.

When I asked Claudia to marry me, I probably put in at least a 1000 hours of hard work and sweat. Fortunately, that was enough for her to say “Yes” in one second.

But first, she made me promise to let her die first. Well, we’ll see if I can live up to that Ask.