How to Get Ahead By Simply Asking (The Right Way)

From a discount on your daily latte to a yearly raise at work, learn the best tips on how to get ahead by simply asking (hint: it's easier than you think!).

how to get ahead

To get ahead in life—more money, more opportunities, more freedom—we have to ask for it, and we have to ask in the right way. The problem is, many of us give up before we even start.

Have you heard these statements before?

  • “Oh, I don’t want to ask my boss for a raise. She’s just going to say no.”
  • “What if he says no?”
  • “Why ask? I already know the answer.”
  • “If they really cared about me, they would’ve promoted me by now.”

Honestly, I hear this all the time from friends, family, and colleagues. But listen to this language… what do you notice? Do you see that failure expectation? And how would you react if a friend spoke to you like this?

Perhaps you’d remind them that “you have nothing to lose.” Perhaps you’d remind them that they’re defeating themselves before they even try.

Why do we undermine ourselves?

I’ll use the example of job salaries. According to a 2008 Gallup poll, 51 percent of Americans believe they are underpaid. Now, let’s imagine that some of them could actually get a higher salary if they just asked, but continued to stay quiet. What are the long-term costs of that?

Think of all the thousands of dollars people cheat themselves out of by not knowing how to respectfully and intelligently ask for a raise at work. That could be anywhere from $2,000 to $20,000 per year in missed salary. Add to that the opportunity cost of NOT putting that in investments, stocks, retirement funds, etc. and now we’re talking about an insane amount of money.

But it’s not just wages, is it? What about asking to meet that guy or girl you really like? What about asking someone successful for coffee to learn and grow professionally?


No more wishing and hoping. No more standing in front of the mirror like Robert De Niro in Taxi Driver. I want to talk about the exact reason why a lot of us never ask for what we truly want.

Two main reasons why we don’t ask for what we want


The first reason is that we’re uncomfortable with getting a “no.”

For many people, being rejected is soul-crushing: your cheeks get red, your face gets hot, and you feel like a complete idiot for the rest of the day. (Welcome to the world of Anthony.) Worse, because there’s so much pain and discomfort associated with a negative outcome, we’d rather say nothing than have to struggle with it.

The second reason we don’t ask for what we want is because we don’t know how to ask. For example, they’ll build up the courage to ask for what they want and they’ll march into their boss’s office and demand a raise… then, by 4:55pm, they’re cleaning out their desk and looking for unemployment.

With that mentality, they think that, when you ask for what you want, there’s a winner and a loser — every interaction is adversarial. OR they ask with their tail between their legs and stutter: “I was thinking… maybe… kinda… if you had the time… could you give me a raise?

The result? The question never gets asked.

Today, I’ll solve these two issues so you can start feeling more confident with asking for what you desire — in many different areas of life — and start learning how to get ahead in life.

And I’ll start by defeating your discomfort with “no.” Why?

Because it’s harder.

How to become comfortable with “no”


Back in October and November 2014, I tried the “Coffee Challenge,” created by Noah Kagan. Here’s how it works:

For thirty days, ask for a 10 percent discount on one thing everyday: coffee, food, etc. If they ask why, do not give them a reason.

The point of this challenge is to get over your fear of asking for what you want because you’re almost inviting rejection and failure. After a month, the goal is to acclimate yourself to that sensation.

I mean, it seems simple, right? Anyone can ask for a discount — this should be a breeze, right?


Well, it was harder than it looked.

You could be at a random coffee shop, about to ask for that 10 percent discount, when suddenly you feel a lump well up in your throat, butterflies attacking your belly, and your heart racing. Suddenly, it’s like you’re back in high school and about to give a speech in front of your entire school… in your underwear.

The first few times, I admit, it was like ripping out my fingernails with pliers. As I did more, however, I got more comfortable and start to focus on things like my tone, vibe, and humor and how I responded to their confusion.

Now, here’s the fun part: what were my actual results? (Drumroll please…)

I batted slightly above the Mendoza line. (That’s 20 percent for non-baseball people).

In other words, over 20 percent of the time, someone eyed me up and down, said, “Sure, why the hell not,” and knocked some money off my bill. A few people even gave me far bigger discounts — including one that was 50 percent — just for asking!

Better still, no one laughed in my face. No one spit in my drink (I think). No one jumped over the counter to chase me out of her store with a rolling pin, while shouting obscenities in an Eastern European accent. Usually, when they said no, they deferred to a higher authority: “Sorry I can’t/my computer won’t allow me/etc.”

Here’s what I learned from the Coffee Challenge:

  1. No one cares if you ask.
  2. Just by asking, you get a “yes” more than you think.
  3. You build momentum quickly.
  4. If you do get a bad response, it almost validates you because you start thinking, “Well I’m pushing myself outside my comfort zone. What are you doing?”

But doesn’t everyone know that, Anthony? Yeah, everyone knows it. But how many people truly understand it?

When you can do this, now you start to get ahead in life.

The key, however, isn’t to get 10 percent discounts on a $3 latte. It’s to build up the fortitude to ask for the bigger things in life.

Let’s move on to the next section.

The right way to ask

question mark

Around the same time I asked for discounts, I launched an interview series called GrowthAddiction. Within a few months after I launched, I secured interviews with two New York Times-bestselling authors, successful entrepreneurs, and Airbnb. How?

By asking.

I’ll share the actual mechanics behind asking a question that gets a good response and why it works better than what most people do. As you read these examples, don’t just copy them word-for-word; take time to understand why they work, how they make you look different, and how they create mutually beneficial outcomes.

(A lot of these tips and tactics I learned from Ramit Sethi so I want to give credit where credit is due. Now, on to the tactics.)

Make it a no-brainer

I know someone who worked at a company for years and was bitter that they didn’t get a raise. I asked her if she asked her boss yet. “Well no,” was the answer. “How do I ask? Do I just go in and demand it?”

No, because that’s how you turn it into a battle. And you never want to turn it into a battle.

Instead, make it a no-brainer for your supervisors. Talk to them and tell them you want take on more workload while asking them specifically what it would look like to excel. Then, do a great job and document what you do. Keep track of your accomplishments and some of the ways you’ve added major value to your organization. Also, do your research and see how your salary compares to the market. You might find you’re being underpaid by thousands of dollars.

Then, schedule a meeting with your boss and frame your discussion in a way that says:

I’m super excited to work at this company and I’m getting a great feel for our direction and how to make a solid contribution. In fact, [showing your documents] I’ve made X, Y, and Z accomplishments in the past ___ weeks and I’m really just starting to build momentum. On my end, I want to continue to deliver amazing work and feel great about coming to work everyday… and I’d like to discuss re-pegging my compensation to reflect that.


Now, how does this differ from how other people ask? Example:

Well, I want a raise because I’ve been here for a while and I think I deserve it.

Instead, by following the first example, you position your request for the benefit of the company and supervisor. Here you are, providing all this incredible value, and to push yourself forward and continue to bring 100%, all you’re asking for FAIR compensation.

It’s hard to argue against.

Remember: you have to do the work. You can’t be Peter Gibbons from Office Space, cause havoc at work, and just demand more money. You have to show your achievements and how they reflect in improving the organization, or you have to show that you’re being underpaid compared to other people with the same position and experience.

For my interview series, all I did was tell them I was a fan of their work (which I was), ask for a quick interview, and make it super freaking easy for them to say yes and schedule a time.

Know when to push

There are times you’re at a huge advantage when asking questions. Think about when you call your bank, get your cup of coffee, or go to a nice restaurant. Everything is set up to give you exactly what you want.

In this situation, I’d advise NOT asking questions, but instead, making statements.

Statements are more powerful and confident. If you call your credit card company, don’t ask for a credit limit increase, request one. That way, they can’t say, “no,” because you never asked a question. As the discussion continues, keep making statements about what you would like to see happen.

All you have to do is substitute the words, “Can I…” with “I would like.”

(Also, know when not to push. There are times when a respectful “please,” “sir,” and “ma’am” would do wonders—for example, finding a restroom in Manhattan without paying.)

Know when to shut up


Sometimes, I get poorly written emails from people that want advice. Usually the first half is an incoherent ramble. Then about midway, they realize they wrote too much and equivocate. At the end, they tack on a really vague question like, “So… what do you think I should do?”

I never respond to these.

As much as I want to help — and believe me, I do — it’s far too time-consuming to sift through the email to find out what they really want to ask and answer a question that I could write a ten-volume book series about. On top of that, I don’t want to have them email me again with another long essay.

Stop doing this.

Instead, tighten up your question and make it easier for them to answer. Compare these two questions and see which one you’d rather answer:

BAD: “What should I do?”

GOOD: “I think I should either do X, Y, or Z. I like X more for three reasons — reason 1, reason 2, reason 3 — but I wanted to get your opinion because you’re far more experienced than me.”


  • Understand that getting a “no” isn’t the end of the world. But rather than chanting that to yourself in your head, go out and actually prove it to yourself. I highly recommend trying the Coffee Challenge for one month to train yourself to ask for things from strangers and acclimate yourself to failure.
  • Make a better case for your requests. Ask for what you want in a way that offers value, not takes it. It requires more work, but if you do it right, the rewards can be tremendous.
  • Know when to raise the stakes and take a step back. Some of this is experience, but there are many times when you can make bigger asks: at hotels, when calling your credit card’s concierge service, at fine-dining restaurants, etc. At those times, make statements instead of questions.
  • If you’re asking something from a high-value individual, tighten up your question and make it easy for them. Stop rambling and be very considerate of their time.

If you get in the habit of asking for stuff you want and do it in a respectful and considerate way, you’ll never know what will happen.

Good luck.