My Queue

There are no Videos in your queue.

Click on the Add to next to any video to save to your queue.

There are no Articles in your queue.

Click on the Add to next to any article to save to your queue.

There are no Podcasts in your queue.

Click on the Add to next to any podcast episode to save to your queue.

You're not following any authors.

Click the Follow button on any author page to keep up with the latest content from your favorite authors.

Esquire Guy

The Do's and Don'ts of Delivering Disappointing News

Magazine Contributor
Articles Editor, GQ magazine
8 min read

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

You’re not gonna enjoy this column. I couldn’t get my head around the subject until the last minute. Then, people wouldn’t call me back. Also, my computer’s been acting weird lately. And the goldfish died. Everything’s a disaster. But what do you care, right?

What you’ve just read is a horrible way to deliver disappointing news. It goes against each of the Principles of Bursting People’s Bubbles, which are:

Don’t disappoint immediately. Even if you’re sure your answer won’t change. Hear the other person out. This gives you time to compose yourself, and it shows respect.

When you deliver the news, deliver the news. Don’t hedge. Don’t be vague. Don’t make excuses. Don’t say, “I’m not sure how we’re gonna be able to get where you want this to go,” or “So, you know, I, uh, see, there’s this, um, what I’m trying to say is … hey, nice pants!”

Specifics aren’t necessary. A simple, clear reason is enough. You don’t need to supplement it with details.

Be honest. Little white lies are not little. They often open up the conversation and put you in the uncomfortable position of explaining something that isn’t true. Anyway, the truth has the benefit of being based in reality. So it’s rarely confusing. White lies are fantasies that demand further discussion. Why put yourself through that?

Be respectful. Your tone and the substance of your refusal (or whatever it might be) should suggest you understand that this is just one setback in the disappointee’s life or career. They have other things going on, too. Maybe even bigger things.

But the most important Principle of Bursting People’s Bubbles is:

Don’t burst bubbles. There shouldn’t even be a bubble to burst. If you shock people with disappointing news, you’re not doing it right. It should be the culmination of a longer conversation.The news just finalizes things.

Phin Barnes, a partner at First Round Capital in San Francisco, emphasizes the importance of maintaining a rhythm of communication so that bad news doesn’t come unexpectedly. “It’s important to communicate early and often and in a consistent manner,” he says, “so that you don’t have a flurry of engagement, then weeks go by with no conversation, then out of the blue an email comes and you say, ‘Yeah, sorry, we’re not interested.’ We really try to maintain a cadence to the delivery.”

The person you’re disappointing needs to understand that disappointment was always a possibility. That seed should be planted early on. If everything seems great and then all of a sudden … bad news?! “That can sort of feel like a sideswipe,” Barnes says.

All of your bad-news communication should involve empathy, of course. But you can’t be empathetic if you don’t know what the other person has at stake. For Nicholas “Nicho” Lowry, professional disappointer (aka, president and principal auctioneer at Swann Auction Galleries and a longtime Antiques Roadshow appraiser), knowing what someone has at stake is the most important part of the antiques-appraisal process.

“You have to find out what it is they hope they have and what it is they hope to get for it,” he says. “What are their dreams? In their mind, how does this conversation end?” So, Lowry asks a simple question: “Where’d you get it from?” And this, he says, is what defines how they’ll be dealt with.

“If they say, ‘Oh, you know, I got it at a flea market for a dollar,’ then we know there’s no emotional interest vested in it. If they say, ‘My grandmother on her deathbed left this to me, and told me above all else, don’t sell this, this will be valuable someday,’ then we have a whole separate scenario we have to deal with.”

And those of us who aren’t Antiques Roadshow appraisers should do the same thing. We should have a basic understanding of the context of the bad news. We should understand what it means.

How to do it

If possible, deliver the news over email, then talk face to face or on the phone.

We’re more accurate and honest when we deliver news over email. And it allows people to absorb the news without having to stifle a frown or tears … or a scream.

Then, talk about it in real time—once they’ve stopped frowning. Or not. Verbal communication (either face to face or on the phone) comes off as much more sincere and respectful than written. It forces accountability in real time. And it allows people to judge not only the news but the way it’s delivered—the nuances of facial expression or the lilt in a voice.

The point is that you’ve given the recipient of the news time to compose themselves. And you’re making yourself available—and accountable.

Why it's so hard

We’re not wired to disappoint people. We’re wired to say yes, to facilitate, to encourage, notes Vanessa Bohns, assistant professor of organizational behavior at Cornell University’s School of Industrial and Labor Relations. “It really comes down to something pretty basic, which is our need to maintain social connections,” she says.

When we have to disappoint people, embarrassment, shame and guilt emerge because our brains want us to maintain our social connections. The truth is, when we deliver disappointing news, we’re disappointing ourselves.

The way to counteract that is to keep things on track early. Not to over-promise. Not to over-praise. Not to let the bubble form. Disappointing news is not a single event. It should be the last stop in a larger event in which disappointment was always a possibility. You owe it to them. And to yourself.

In Case of Pushiness

Occasionally, people don’t accept disappointment. Here, some suggestions for when things escalate.

Round 1: “Lars, I’ve thought about your proposal. It’s an interesting idea. We don’t have the infrastructure for implementing it right now. But it’s an interesting idea.” (Classic yes-no-yes rejection.)

Round 2: “It’s just that this company—nay, the world—isn’t ready for that level of … involvement.” (Classic It’s not you; it’s, in this case, every person on the planet who isn’t you rejection.)

Round 3: “If only the world were ready for the Lars 3000.” (Classic wish rejection.)

Round 4: “But we don’t know from heating elements at this company. A toilet paper warmer needs a heating element!” (Classic good-natured incredulity rejection.)

Round 5: “If only you’d come to us last week, when we were planning the budget for the next 50 years.” (Classic condition for past acceptance rejection.)

Round 6: “Look, you know I would if I could.” (Classic It’s not me; it’s the system rejection.)

Round 7: “Fine, here’s some money. Go out there and warm some toilet paper.” (Classic total capitulation.)

Key Technical Matters

Disappointing news should be the final message in a continuum of communication that has set the stage for calm acceptance of any kind of news—good or bad. It should not be a surprise.

This requires honesty and candor in all dealings with the other person. And respect. And communication. And perhaps a consolation prize. A corporate gift of some kind. Maybe a personalized tote. 

Remember that disappointment involves embarrassment—for both the disappointer and the disappointee. (Note: Disappointee is not a word.) Your goal should be to mitigate, if not eliminate, that embarrassment. 

So, never dismiss a request upon first hearing it. Even if you’ve made up your mind, allow the person to argue for what they want. Give them a forum. 

Then be forceful but respectful. Be concise. Give a single truthful reason. No white lies. No hemming. And, for the love of god, no hawing. 

Then talk about the future. Look ahead to a world in which this episode of disappointment is but a distant memory. 

Then throw in one of those squishy stress-reliever things. People love those. 

More from Entrepreneur

Jon Horowitz is dedicated to helping brands with grow their social footprint by aligning with influencers and creating innovative content.
In as little as seven months, the Entrepreneur Authors program will turn your ideas and expertise into a professionally presented book.
Create your business plan in half the time with twice the impact using Entrepreneur's BIZ PLANNING PLUS powered by LivePlan. Try risk free for 60 days.

Latest on Entrepreneur