10 Steps for Handling Those Conversations You Don’t Want to Have

How to manage the most difficult, delicate, distasteful conversations
September 3, 2015

Kathi Elster, a New York management consultant, is paid to have the kinds of conversations no manager or business owner wants to have. She was hired by the head of a law firm to interview his staff and uncover why he was experiencing nearly constant turnover. If those interviews required discretion, they were a romp compared to the conversation Elster then had to have with the lawyer himself, sharing her findings that the steady exodus resulted from his frequent and profane outbursts, which left his staff feeling verbally abused.

Some of the workplace interviews that Elster is enlisted to conduct center on highly sensitive issues such as inappropriate dress or personal hygiene. Once she was tasked with confronting an employee who spent hours a day locked in the office’s only restroom, forcing co-workers to exercise extreme self-control.

“Managers tend to avoid having these uncomfortable conversations,” Elster says. “Given everything else you have to do during the workday, it’s natural to want to push them to the bottom of your to-do list. But the issues that need to be addressed don’t go away. And by the time managers or business owners get around to these conversations, the other person often feels blindsided because the problem has been going on so long.”

Outsourcing or dodging difficult conversations is a perilous gamble. In business, being adept at navigating the hard talks can mean the difference between flourishing and folding. A decade after Douglas Stone, Bruce Patton and Sheila Heen published their best-selling Difficult Conversations: How to Discuss What Matters Most, they reissued the book with a new preface and a stern warning. Businesses have devoted the last 20 years to technological innovations, streamlining processes and cutting costs. With little left to cut, they write, breakthrough performances in coming decades will require dealing with conflict and differences effectively. Leaders and companies that can adroitly confront what matters most, the authors conclude, “will leave their competition in the dust.”

In case you think you can get promoted past having to manage awkward tête-à-têtes, the opposite is true. “As you become more senior, you spend more time having difficult conversations,” Heen says. “That’s because these conversations get kicked up to you, and handling them well is a core competency for senior leaders and entrepreneurs. The inability to do that is one of the most common reasons people don’t succeed: They have a great capacity to drive revenue or a keen understanding of a market, but they’re not prepared to handle these conversations skillfully.”

And the skills that come into play when negotiating a difficult conversation with an employee are the same ones that you’ll need when handling a challenging topic with your business partner, clients, stakeholders, spouse or friends.

Here are the 10 vital steps for navigating sticky personal and professional conversations—or moving “from dread to said,” in the words of Donna Flagg, communications specialist and the author of Surviving Dreaded Conversations: How to Talk Through Any Difficult Situation at Work.

1. Summon your inner warrior. Firing an employee, telling a longtime vendor you’re cutting your orders by 80 percent, confronting your business partner about what you believe is unethical behavior, or even talking to your neighbor about a barking dog: All are situations that trigger trepidation. “We may be rejected or attacked,” Heen and her co-authors write. “We might hurt the other person in ways we didn’t intend, and the relationships might suffer.”

“These conversations take courage, and often that’s missing,” says Steve Albrecht, who holds a doctorate in business administration and is a San Diego-based human resources consultant who specializes in high-risk workplace behavior such as violence, substance abuse and bullying. “People will have two examples of bad behavior, but they tell themselves they’re going to wait until they have five before they bring it up. They’re holding out for the perfect time to have the conversation.

“And you know what? There is no perfect time. When I’m called in to handle these conversations, things have gotten so bad that sometimes people or departments aren’t speaking to each other. I don’t mind the work, but I often feel the problems could have been solved six months or a year ago if bosses behaved like bosses and partners had the guts to talk to each other.”

2. Be proactive. When people develop their skills in having difficult conversations, they end up with fewer crises, Heen says, because they’re responding sooner to developing problems. “We don’t do the calculations accurately,” she says. “We know the risks of raising a difficult topic, but we ignore the bigger risks of avoiding a conversation.” Plus, Heen says, we rob the other party of the chance to improve things (the neighbor trains his poodle to stop barking at every passing car) or make accommodations (a project manager adjusts a product launch when he’s told the prototypes are taking longer than expected).

Rather than waiting as costs escalate, let a client know that you’re running 20 percent over budget. When you have the conversation, offer a solution: presenting ways to trim the budget for the final phases of the project, proposing to share the cost of the overages, and outlining a strategy for ensuring your cost projections are accurate on future projects.

Albrecht agrees. If you want to avoid having big, difficult conversations, he suggests having smaller, frequent conversations. Supervisors should coach employees on a daily basis, and partners should regularly check in with each other on goals and strategies. “Be vigilant,” Albrecht says. “Pay attention to what people are doing and how they’re doing it. Make small suggestions rather than storing them up for a major performance review or strategy session six months down the road. Like sailing, if you don’t make minor midcourse corrections, you find yourself drifting in the opposite direction of where you intended to go.”

3. Set the stage. Plan the conversation. You don’t want sensitive discussions to be triggered by a spontaneous exchange during a meeting. If you have to share unwelcome information, be sure you initiate the conversation. “Do not have the person to whom you’re delivering the bad news be the one to approach you,” says Flagg, who also runs The Krysalis Group, a New York-based consulting firm. “If you do, you lose the opportunity to set up the conversation properly, which is the single most important thing because it sets the tone for what follows.”

Pick a private setting that allows you to talk without interruption. Establish the agenda immediately. When Elster had that turnover conversation with the lawyer, she began, “You and I are going to have a difficult conversation so I need for you to listen to me without jumping to conclusions.”

If you’re having a difficult conversation with your business partner, you might be tempted to do it during lunch or over after-work cocktails. Albrecht suggests you set the right tone by talking in the office. “This is a crucial business conversation, so make it about business from the start,” he says. He suggests saying something to your partner like, “I need to talk to you right away. Let’s go into the conference room and close the door.”

4. Be direct and clear. Sometimes in an attempt to make a conversation less uncomfortable or unwelcome news more palatable, we try to be diplomatic or tactful. That can backfire. “Tact is well-intended,” Heen says, “but it can often mean that you’re being indirect” and can be misunderstood.

Say an employee is chronically late. In an effort to be benevolent, you might make a general declaratory statement, for instance: “It’s really important for people to be here and show up for meetings in a timely way” or “I rely on people being here during the workday.” Or to establish empathy, you might tell a story about yourself. For example, you’ve gotten complaints about an employee taking days to reply to emails or calls, so you say something like, “When I was starting out, I didn’t realize how important it was to get back to people right away.”

In both cases, you think you’re being clear, Heen says, “but the person on the receiving end doesn’t know you’re talking about her, or she’s not really listening to you.”

5. Be concrete about what you have observed. Offer specifics rather than generalizations and don’t use labels to describe behaviors. Let’s go back to the constantly tardy employee. If you say, “You’re always late,” you’re creating room for your employee to dismiss, debate or ignore you. I’m not always late, he might think. I got to the office five minutes early today. Specific examples are far better: “You were 20 minutes late on Monday and 30 minutes late on Tuesday. You’ve showed up 10 minutes late for the past three weekly meetings.”

Use the same approach for inappropriate behavior such as workplace drinking. “Here’s specifically what I’m seeing that would lead me to believe you have an alcohol problem,” you might say. Then, Albrecht says, describe what you’ve observed: “You smell like alcohol. You threw up at work the other day, and it’s not because of the flu. I’ve caught you sleeping at your desk. Someone saw you drinking something in the parking lot that didn’t look like coffee.”

If your company has a policy of offering employee assistance for substance abuse, discuss that on the spot. And let the employee know the consequences of his behavior: “If I suspect that you’re drinking again, you’re putting your job at risk.”

6. Separate intention from impact. People’s intentions are invisible, Heen says, so don’t try to guess what they are. Instead focus on the consequences of their behavior. Rather than saying, “Apparently you don’t think it’s important to be on time” or “You think your time is more valuable than anyone else’s,” try something like, “When we wait 15 minutes for you to arrive before we start the morning meeting, that causes us to run late all day.”

Focusing on impact is critical when having a conversation with a business partner or a team member who holds the same rank as you. These are harder conversations than those with people who report to us, Albrecht says, so we’re even more likely “to beat around the bush.”

When you have an issue with a peer, open the conversation with a line like, “I need to talk to you as my partner and my friend.” Offer examples of the objectionable behavior—“You told three off-color jokes at the pitch meeting last week.” Then move on to how it might be hurting business. “Nobody laughed, and two people on the client side told me the jokes made them uneasy. If clients don’t feel comfortable with us, they’re not going to give us their business.”

7. Shift from a blame conversation to a contribution conversation. Rather than assuming a problem is entirely the other person’s fault, own your part of it, Heen advises. You might say something like, “I should have brought this up six months ago. Perhaps you didn’t realize how important it is for us to keep to our schedules.” Remember, she continues, the conversation isn’t about blame; it’s about fixing a problem. If you take some accountability that often makes the other person more willing to accept responsibility for his  part.

8. Adopt an and stance. Using and can be the verbal equivalent of uncrossing your arms. It conveys a posture of being open to the other person’s point of view while not abandoning your own, Heen says.

Listen to the difference in these two sentences to a staff member. “You come up with really great big-picture ideas, Jody, but you need to pay attention to the details of projects, too.” Then the alternative: “You come up with really great ideas, Jody, and you need to pay attention to the details of projects, too.” It’s easy to imagine that the first statement, with its tacit criticism, is likely to make Jody feel defensive. The second sentence doesn’t diminish Jody’s contributions and is much more likely to open up a back-and-forth about the tools she needs to follow through on her creative ideas.

Heen says the use of and acknowledges someone else’s point of view without “diminishing the power you have to implement your decision and to be clear that your decision is final.” Take the painful conversation of letting a longtime supplier know you’re cutting back on orders. “I’m reducing our orders because it’s the right thing for the bottom line of the company right now, and I understand that’s disappointing to you. I know you’ve stood by us when we were just starting out, and I still need to make these cuts.”

9. Strive to be a good listener rather than an artful persuader. In the classes on negotiation that Heen teaches at Harvard Law School, she tells her students something surprising: Advocacy is the strategy of last resort. “If you’re trying to persuade someone who’s neutral,” she explains, “advocacy can be effective. But if they have a different point of view, it’s highly ineffective.” In these situations, “the most persuasive thing you can do is be open to persuasion yourself.” That’s because when you’re trying to change someone’s position, you’re not listening—“your internal voice is too active,” Heen says. What’s more, when you’re pushing someone to switch to your perspective, they’re going to push back.

“I’m more likely to persuade you if I’m listening,” Heen says. “Listening is the most persuasive weapon.” It sets in motion the social norm of reciprocity and heightens the odds of reaching agreement on a dispute.

10. Recognize that some difficult conversations will not have happy endings. Albrecht was once hired to talk to the founder of a tech company who greeted employees exuberantly. “He was this really big guy, and he’d hug everyone by lifting them off the ground,” Albrecht says. “It was terrifying. Men found it emasculating, while women thought it was inappropriate touching.” The board of directors wanted the behavior stopped.

“I told this guy that it was great that he was enthusiastic, but his behavior had to end,” Albrecht says. “The company could get sued if employees considered the hugs harassment. Valuable employees might leave. And in a highly competitive marketplace for talent, hiring people might become difficult. Customers and clients might hear about it and not want to bring their business to the company.”

The outcome: The hugs continued, and the founder was fired from his own firm. 

How are your conversation skills? Make sure you know the 5 common mistakes people make in conversations—and break the worst habits.

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