The Best Ways to Tell the Hard Truth at Work

Ms. Kunish, a product manager, waited a few weeks to watch Mr. Dolci in action. “I needed to know he wouldn’t throw me under the bus” for offering criticisms. He didn’t.

She challenged Mr. Dolci directly after he nixed her proposal during an executive-team meeting to include a drill bit with one of ​the company’s closet-shelving products. She asked to see him in his office after the meeting and made her case again, citing customer data.

Mr. Dolci says he saw that she was right, but didn’t agree immediately. “I pushed back and she stood her ground,” Mr. Dolci says. He has since promoted her twice, to brand director. “It’s important to me that employees have the courage to disagree with me,” he says.

Giving candid critiques is essential to solving problems on the job. It’s an especially hot topic at tech companies, with their flattened hierarchies and ceaseless time pressure. Employees may care deeply about their team’s results and depend on their colleagues to do well, but hesitate to criticize them for fear of sparking conflict, hurting feelings or being seen as a jerk.

Airing disagreements face-to-face prods managers and employees to examine their assumptions and make better decisions, says

Michael Roberto,

a management professor at Bryant University in Smithfield, R.I., and an expert on decision-making. “You have to remember you’re on the same team and you’re trying to strengthen each other’s argument—not win the argument,” he says.

Asking permission before offering feedback can be helpful, says

Achim Nowak,

a Hollywood, Fla., executive coach. “Instead of pouncing on the person, say, ‘I have a couple of thoughts I’d like to share with you. Is this a good time?’ ” he says. Prefacing your remarks with, “I’m sure you’ve thought about this already,” can lend humility, Mr. Nowak adds.

Bosses who want honest feedback often have to ask for it, welcome it warmly and listen carefully even when they disagree, says

Kim Scott.

She is the author of “Radical Candor,” a best seller about how to give honest feedback at work.

Art Karoubas, vice president of product at HighGround, a Chicago maker of employee-engagement software, asks employees every three months how he can be a better manager. He listens when they challenge his plans. “Even if I’m 100% convinced that my idea is the best idea, I open it up and ask, ‘What do you think?’ ” he says. Then he follows up with questions.

He listened recently to an employee who objected, saying that the team was planning to roll out a new software feature too fast. That started a conversation on his team about a broader change the employee thought was needed to improve the product, Mr. Karoubas says. They released the new feature on time, but laid longer-term plans to make the additional, broader fix.

Akhila Tadinada, a director in Redmond, Wash., for

Hitachi

Vantara, says she invites employees to challenge everything. She was reluctant to back an engineer’s recent proposal to build an online marketplace for the company’s industrial applications, saying customers wouldn’t be interested. The engineer argued that it could be a helpful innovation. Although she was still skeptical, she gave him time to build a prototype and test it. The completed product was a big hit with executives at a recent customer conference.

Avoid turning criticism into a personal attack, Ms. Scott says. She recommends following a “situation, behavior, impact” formula: Describe the situation where the problem behavior occurred, the person’s specific actions and their impact. Instead of saying, “You’re sloppy,” say, “You’ve been working nights and weekends and it’s starting to take a toll on your ability to catch mistakes in your logic.”

It’s important to know the person well enough to anticipate his or her response, Dr. Roberto says. “You have to determine who can handle more radically or brutally candid criticism, and who needs a gentler approach,” he says.

Ted Devine

tries to hire employees who will thrive in the candid culture at his company, Insureon, an online small-business insurance agency in Chicago. “You have to build one-on-one relationships with people so they trust you. But also so you can push them,” says Mr. Devine, the company’s CEO.

Belen Tokarski, Insureon’s chief administrative officer, says she enjoys a challenge, but facing Mr. Devine sometimes feels like “walking right into a fire.” Her team recently missed one of its quarterly targets because she reassigned a few employees to closing sales.

“Why did we do that?” Mr. Devine asked. Ms. Tokarski defended her decision, and Mr. Devine told her, “OK, fine. These are battlefield decisions leaders have to make.”

But he didn’t pretend to be happy, he says. When employees slip up, “I don’t want them expecting me to say, ‘Hey, you missed your numbers, come on in, I’m going to buy you a beer,’ ” he says. “But I want them to give me bad news. The rule is, don’t surprise me. Talk to me about it so I know and can try to do something about it.”

Write to Sue Shellenbarger at sue.shellenbarger@wsj.com