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Ready For Anything

How and Why to Offer Words of Encouragement

Magazine Contributor
Articles Editor, GQ magazine
7 min read

This story appears in the October 2015 issue of Entrepreneur. Subscribe »

Encouragement. It sounds like such a small thing. Subtle. Cute. It’s what we do with timid kittens.

But encouragement isn’t cute—it’s fraught and powerful. When you’re encouraging, you’re instilling courage. That’s huge. And that’s hard. And it’s way more compelling than motivation.

Motivation doesn’t depend on circumstances. Motivation is for people who are already inclined to try to succeed.

The commencement addresses that go viral are always more encouraging than they are motivational. The speakers recognize a specific concern—like needing to get a job or facing an uncertain future—and discuss ways it can be overcome. They don’t offer some vague challenge like “surmounting an obstacle” or “seizing upon your dreams” or “surmounting your dreams by seizing upon an obstacle” or whatever the current motivational clichés are. Do these addresses involve motivation? Yes. Are they “motivational” in that unctuous way that motivational things are? No. Commencement addresses make listeners accountable. Encouragement inherently involves accountability—and not just for the one being encouraged. The encourager is accountable, too.

How To Encourage

Praise the actual. If you read all the research on motivation, it pretty much comes down to this: Praise works better than criticism.

“We all have an emotional tank. It works like the gas tank of a car. There has to be way more tank-filling than tank-draining,” says Ruben Nieves, former Stanford University men’s volleyball coach and current national director of training for the Positive Coaching Alliance, a nonprofit organization based in Mountain View, Calif., that focuses on teaching and encouraging positive character-building in youth and high school sports.

Acknowledge the potential. Encouragement involves the acknowledgment of a negative thing—that the people being encouraged don’t know they’re not doing (or trying to do) the thing they should be doing. They might think they’re doing just fine, that they’re being appropriately effective and ambitious. Encouragement often involves bursting a confidence bubble.

To be encouraging, you must believe two things to be true. One, the person is not trying hard enough, which is probably not something the person wants to hear; and two, if the person tried, he or she could do great things, which is good. The key to encouraging is to deliver the bad news in a way that doesn’t force the person to dwell on inadequacies. The key to encouragement is tact.

Says Whitney Wolfe, founder and CEO of Bumble, a dating app: “Start off by telling them their strong points and acknowledging their efforts and talents. ‘You’re extremely creative and you’re brilliant, and you’re wonderful at coming up with new ideas.’ And then from there you can say, ‘I would love to see you be able to segue that into a more organized manner.’ It’s very easy for people to kind of lose track of what they’re doing right and what they’re doing wrong.”

Challenge specifically. You motivate generally. But you must encourage specifically. This holds the person accountable. “You should ask this person for help.” “You should go after that job.” “You should consider switching to this career.” Like that.

“For example,” says Wolfe, “‘I think you have the potential to be a fantastic leader and to have three people work under you … but in order to do that, I think we need to improve upon your time-management skills, your organization skills,’ vs. coming at them saying, ‘You’re disorganized.’ Approach it from a potential route.”

Why It Matters

Encouragement means empowerment, says Samir Nurmohamed, an assistant professor at the Wharton School at the University of Pennsylvania.

“A lot of it comes down to guided autonomy,” he says. “So, on the one hand, we know from research that people are much better at work when they feel empowered, which consists of having meaning on the job, a sense of autonomy, a sense of confidence, and also an impact on what you do and the people you’re trying to help. Yet you don’t want to feel so autonomous that you have no direction. It’s one thing to feel autonomous in terms of your motivation, but it’s another thing to be autonomous and go in the wrong direction.”

You have to discourage before you encourage. That challenge is scary—for both parties. But the reward is sweet. Not only have you helped someone achieve a goal; you’ve helped someone achieve a goal that he or she didn’t previously have. That’s not merely motivational—that’s magical. You’re a wizard, a coach, a seer and (if we’re being honest) kind of a pain, all at the same time.

Key Technical Matters

Encouragement has two parts: pointing out potential and challenging the person to succeed at a specific goal.

You have to point out what it is you believe the other person could do. And you have to challenge him or her to do it. Which is why it’s so much more meaningful than motivation.

You can motivate anyone. You can encourage only someone you actually believe in.

Encouragement requires specificity.

You don’t encourage someone to succeed. (That’s motivation.) You encourage someone to succeed at a specific task or job.

You don’t encourage people to “do it.” (That’s a potential criminal charge, depending on what “it” is.) You encourage people to do that thing you think they are prepared to do but that has never occurred to them.

Behind every successful person is someone who said: “You should try this. I think you’d be good at it. And here’s how you should try.”

That last part is important. Encouragement without guidance isn’t encouragement. It’s discouragement. “Here’s what you’re not doing! Bye!”

When you encourage, you don’t just change how people work. You change the way they perceive their abilities. Which changes their careers. Which changes their lives. Which is a really big deal.

DIY Pat On The Back

Encouragement requires that we tell people they aren’t realizing their potential and then challenge them to achieve their goals with a specific plan. But what if no one is doing that for you?

  • Determine that you know how to do pretty much everything that’s required in your work.
  • Realize that this is obviously absurd and that there is so much more you could do!
  • Pretend you are your own supervisor. Adopt another personality if you have to. Stern taskmaster. Benevolent mentor. Bumbling villain—Dabney Coleman in 9 to 5, say. Whatever you want to do here is fine. You want to put on a different outfit? Put on a different outfit.
  • Realize that you were really good in your high school production of Bye Bye Birdie and that maybe you should’ve stuck with that.
  • Enough with the wistfulness.
  • Answer common questions used in workplace self-assessments: “What am I good at?” “What do I need to improve?” “Do I make use of available resources?” “Do I ask questions when I need help?” “Do I examine current best practices?” “Am I proud of my work?”
  • Add this question posed by Denzel Washington as legendary high school football coach Herman Boone in Remember the Titans: “Will you ever quit?”
  • Answer: “No.”
  • I can’t hear you.
  • “No!”
  • Write down the steps required to achieve your new goal.
  • Give yourself a deadline.
  • As you get up to leave, walk yourself out while placing a hand on your shoulder.
  • Shake hands with yourself.
  • What, are you a method actor now?
  • Whatever. Just get to work, Denzel.

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