The Question You Need to Ask to Achieve Your Goals

Do you know what question you ask the most?

If you want to achieve your goals — faster, with better results, and with a bigger impact — you have to give your brain what it wants: the answer to one all-important question.

Oprah Winfrey saw it in action with every show she did. She hosted the most talented, intelligent, daring, and accomplished people. They always looked great. They were always a hit with the audience. Well, almost always. I’m sure it was exhilarating for them, but it didn’t stop any of them from asking her the most important question after the show: “How did I do?”

Want to make progress? Answer the most important question: “How am I doing?” Click To Tweet

It’s a necessary, important question—the perfect question. We need feedback to know whether we’re doing the right things. It’s why we compete. It’s why we have grades. It’s why we want our bosses to give us a pat on the back or at least some direction. Even Clarence the Angel asks it of Joseph in It’s a Wonderful Life.

The first time I heard the Oprah story, in an interview or article, I thought it was sort of funny or cute. Oh look, successful people are a little insecure, too. And then I remembered an important lesson taught to me by New York Yankees legend Bullet Bob Turley. He spent his life surrounded by winners in every world—sports, business, entertainment, politics. When I asked him what made them different, he told me that none of them really thought they were that good. And every day they worked at improving.

Because that’s how you make progress and achieve your goals!

Serial winners don’t assume anything. They don’t assume they’re doing great and are on track. They don’t assume that they’re heading in the right direction. They don’t assume that they know what they need to know. They don’t assume that they’re always nailing it.

Instead, winners look to their environment and ask, “How am I doing”—over and over. And they aren’t afraid of the answer.

They use the answer to make adjustments that lead to faster progress.

If you aren’t getting the feedback you need to know how you’re doing on your goals, you’ll lose your motivation, you won’t know whether to adjust your activity, and you won’t make much progress. Here are two ways to set yourself up for success on your goals by getting regular feedback.

1. Measure what you can.

I’ve never seen a high-achiever who wasn’t totally locked in on the numbers. Numbers don’t lie.

For a lot of our goals, we can set specific, measurable, time-bound goals. Make sure you do this whenever you can—and set goals for results and activity.

Then you have to decide what information you’re going to track. What information is easily available that will give you a good sense of whether you’re making progress? Is it financial data? Is it data on key deadlines that you’re hitting or missing? Is it data on your health? What information do you need to answer the question “How am I doing?” with confidence.

Once you know what you’re going to track, decide how you’re going to track it: What makes sense? Daily, weekly, monthly? On your calendar? In a spreadsheet? In a special database (like accounting)? What is easiest, makes the most sense for the information, and will allow you to review it quickly.

Finally, figure out if you need help from other people to track it. This might be true if you’re an entrepreneur or business leader. You might have to get people excited about what your tracking and why, and make it easy for them to help. Remember, simplify, simplify, simplify. Only go after the information that will actually tell you if you are on track to achieve your goals.

2. When you can’t measure, ask human beings.

We can’t always measure progress with numbers. Some of our goals require subjective feedback from the people who matter most—those on the receiving end of whatever it is we’re delivering. When that’s the case, you need to ask them for that feedback if you want to achieve your goals.

Yes, there are ways to put measures on most things. A restaurant can ask people to fill out surveys. They can use a tool like Fred Reichheld’s Net Promoter Score, asking “How likely is it that you would recommend us to a friend or colleague?” And they do. But throughout the night, the manager also circulates, asking the patrons, “How was everything tonight?” He’s not just being friendly, you know.

Start asking the people who matter how you did—your boss, your spouse, your kids, members of your audience, your followers. Try to get them to be honest with you. The best way to do that is to actually listen to their feedback and thank them for it.

The important thing to know is that when serial winners ask the question, they’re not looking for false validation. They really want to know the answer, even if it’s not great. Next week, I’ll explain what they do with the answers. For now, if you want to achieve your goals and win more in all areas of your life, figure out whether you’re getting the best answers to the big question.

If you know people who are stuck because they aren’t answering this question, please email or share this article with them.

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Taylor Williams

This reminds me of the sharpen the saw/axe story. Anyone know that one?

Basically one person works as hard as they can all day long without taking a break and the other takes short breaks to sharpen their saw. At the end of the day, the one who took breaks and sharpened the saw got more done.


EXACTLY!!! I think taking a time out to evaluate and adjust pays far more dividends than blindly pushing forward. It’s all about staying SHARP!

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