You Need To Ask For Things And There’s A Right Way To Do It

If you want to be successful, you need to ask yourself some questions.

Like: What am I afraid of? What have I got to lose?

You often hear the late Steve Jobs quoted on this point:

Remembering that you are going to die is the best way
I know to avoid the trap of thinking you have something
to lose.

He’s right, of course, but alas, most of us prefer to think that death is something that happens to other people.

Besides, Mr. Jobs was a billionaire. 😊

Why don’t we ask for things?

Anthony Yeung says we fear losing face. Being embarrassed. Getting rejected.

We’re uncomfortable getting a “no,” so we stay silent to make sure we don’t get one.

Mr. Yeung took the Coffee Challenge. I’d never heard of it. It’s a “failure game” created by entrepreneur Noah Kagan.

For thirty days, you ask someone for a 10 percent discount: on a coffee, a donut, whatever. You don’t give a reason, you just wait and see what happens.

The idea is to get comfortable with being uncomfortable; to get comfortable with getting a “no.”

At first Mr. Yeung suffered extreme anxiety. Eventually he got more relaxed. He also got the 10% discount a little over 20% of the time. Once he got 50%. You never know.

My favorite part of Mr. Yeung’s post was his contention that we don’t ask because we don’t know how to ask.

We think there has to be a winner and a loser. We think asking has to be adversarial. “I want a raise. I’ve been here awhile, and I deserve it!”

Or else we telegraph defeat as a foregone conclusion: “I was thinking, kinda hoping, maybe you could, uh, give me a raise?… maybe…??”

A better way: have a plan. Do your homework. Be ready to make your case. Make it easy for people to say yes.

Take asking for a raise (or, if you’re a new grad, negotiating your starting salary):

Best-selling author Ramit Sethi says that 80% of the work needs to be done before you walk in the room.

Margaret Neale, a professor at the Stanford Graduate School of Business and co-author of Getting (More Of) What You Want, says it’s not enough to figure out how much you want.

You need to figure out what the company wants, and what your boss wants: what their problems are, what their goals are.

Here’s a key point: view negotiation as collaborative problem-solving. You’re trying to achieve a win-win (which also means you’ll avoid coming off as too greedy or demanding).

Unless your market research shows you’re being drastically underpaid (and you’ve got the numbers to back you up), take a long-term approach:

Tell your boss you want to exceed expectations. Ask what it will take to do that. Get hard numbers if you can. (Perhaps it will involve taking on more work.)

Then go out and do the work. Document what you do. Keep track of your accomplishments and how you’ve added value to the company.

After three months, ask for a meeting. Show your boss how you’ve hit the numbers and exceeded expectations. Say you’re excited to be part of the company and look forward to new challenges– and that you’d like your salary to better reflect that commitment.

You’ve done the work and you can prove it. You want it to be a win-win. You’ve made it hard to say no.

The key take-aways for me:

1. You have to be brave and ask for what you want.

2. “Bravery” is synonymous with tolerating discomfort. (Getting a “no” is not the end of the world.)