Why You Should Give the Gift of Encouragement


Just as important as the work you do is the person you bring to work. Your mood, outlook, and actions echo out to those around you.

One of the best ways to contribute to your surroundings to give the gift of encouragement.

There are sincere dangers in making “Great work!” an expected platitude. Let’s be clear: when everything is great, nothing is.

But I believe most of us give (and get) less encouragement than we’d like, in work and life.

One likely source of this problem is the Prisoner’s Dilemma nature of encouragement. A thoughtful compliment, for example, actually involves a bit of risk, when you think about it:

  • You could come off too strong. Good intentions in hand, you sing the praises of someone you admire with overblown language and end up making things a little weird.
  • They may feel embarrassed. Despite being flattered by what you said, the complimentee may not know how to react. They jokingly brush your comment aside, which hurts your feelings.
  • They don’t appreciate what you said. Fortunately, far rarer than the other two, there are and will be instances where your belief in someone is well understood, and they just don’t care.

In short, encouragement gone wrong can feel like a loss. Imagine that.

This was made clear to me after a friend recently tried to give me a compliment; I nervously made a joke to break the tension I felt (see point #2), and they rightfully responded: “Don’t make nice gestures a losing proposition for me.”

When You Needed It Most

Acknowledging that encouragement isn’t without downside reduces the guilt of not giving it away as freely as you’d like.

That addressed, you, like me, probably still want to offer up more of it. Encouragement makes people feel good and can build bonds to weather the toughest of times — it’s a “do unto others” principle that never goes out of style.

To spot opportunities, I try to recall moments where having someone in my corner made all the difference. Or, those times where I wanted nothing more than to have support, but didn’t.

Small gestures count for a lot. The first comment I ever received on my blog came from “Anonymous,” who offered up praise for an impassioned first attempt, and then continued with some helpful critique. What a classy move — we will never know each other, but it meant a lot to me. In that fragile state, one mean comment may have stopped me in my tracks.

Whenever one of my teammates writes for the Help Scout blog, I try to remember that initial anxiety of putting thoughts to page for all to judge. Recently, I’ve been collecting the feedback I’ve seen about their pieces on social media and wherever else, and I send it to them via email a few weeks after the piece has been live. With this gesture, I’m just the means for encouragement to find it’s way to the person who deserves it.

There are far deeper moments to be had, for sure. But the best way to start off is to start small.

You’ll Make It

Coach Jim Valvano wholly inspired my thinking on this topic through his talks on gifting confidence through belief.

He describes folks with this ability as “one of those people who, after you speak to them, you always feel better than before.” Even if the conversation is hard, even when discussing your current failings, you always leave their presence with sights set high and the belief you can get it done.

Valvano’s most poignant take on this idea comes from a speech he gave in 1987 on the most meaningful gift his father gave him:

My father had a heart attack and he died. I lost my best friend in the whole world. This is not a sad story, it’s a happy story, but I was knocked for a loop. Those of you who have lost a loved one know what that’s like.This was the first time in my life, and I didn’t know how to handle it. With him gone, I was missing … I couldn’t understand what it was I was missing. What was it? I didn’t see him all the time, I was traveling a lot. And then it hit me, what it was he gave me. I think it’s the most powerful gift I’ve ever received. And it’s a gift I find we don’t like to give to each other, both in our business and our personal lives. I’ve spent two years trying to give this gift to other people.

The gift my father gave me every day of my life was he believed in me. My father believed in me.

He believed in me when I failed. He believed in me when I wasn’t as fine a son, friend, husband, father as I could be. And I’ve done all of that. But he’s the one person who when I didn’t measure up to my standard or someone else’s standard, he’d look me in the eye and say, “You’re gonna make it, I know you are. You’re gonna make it.” It’s the greatest thing.

And I said to myself, “How many people do I give that to?”

My own players, how often when they make a mistake am I critical, but never, ever look them in the eye and say, “You’ll make it, I know you will. I know you can. I believe it.” How many people who I work with do that? How many people who I work for do that?

Oh, it’s an incredible gift, and I’ve worked two years now to add it to my personal philosophy.

Give the gift of encouragement whenever you can. Stay honest with yourself: it’s not an effortless gift to give, but it’s far too valuable to be so rare in this world.

Truman Capote said it best: “Anyone who ever gave you confidence, you owe them a lot.”

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Gregory Ciotti is the lead content strategist at Help Scout, the invisible help desk software. He writes about marketing, customer success, and workplace culture on the Help Scout blog.