Seven Tips on Navigating Sticky Workplace Conversations

The following information is used for educational purposes only.


Seven Tips on Navigating Sticky Workplace Conversations

By Kelly Eggers

No matter how you might try to avoid them, at some point in your career you will need to have difficult conversations with your boss. It might be asking for a raise, delivering bad news or explaining you can't get all of your assignments completed. How you handle these conversations can make the difference between a positive or negative outcome.

Jodi Glickman, a former Goldman Sachs investment banker and founder of Great on the Job LLC, has written a new book, Great on the Job, which delves into how to have an effective communication strategy at work. She provides step-by-step guidelines on handling tricky situations.

"Your success has almost everything to do with your day-to-day interactions," says Glickman.

FINS talked with Glickman about how to communicate with your boss to reinforce the idea that you're an invaluable asset to the team, regardless of what bad news you're conveying. Here are recommendations on how to handle seven typical sticky situations.

When You're Trying to Start a Conversation


Make sure first that the person you're speaking to is ready to listen by asking if they have a few minutes to talk, says Glickman. "Everyone has been on the receiving end of a phone call or a knock at the door where the person doesn't ask you if you have time to speak," says Glickman.

Not only is it rude, she says, but it indicates that you don't value their time as much as you value your own. After you've introduced yourself and briefly indicated the purpose of your call, ask: Do you have a minute to speak? "It's polite and courteous, but it's also a good business decision," she says. "There's nothing worse than if the person you're talking to is saying to themselves 'I don't have time for this conversation.'"



When You're Trying to End a Conversation


Just as important as setting a positive tone at the beginning of a conversation is ending it in a way that invites another discussion, Glickman says. "You always want to be planting the seed for next steps," she says, rather than awkwardly parting ways with no indication of when they'll hear from you again.

The best goodbyes consist of a "thanks" and some indication of forward momentum: when you plan to follow up, offering to pass along relevant information, or letting them know you'll keep them posted on the status of an assignment. "Notice in life that when there's no forward momentum, there's a sense of 'where do we go from here?'," she says.



When You Want to Pass on a Project


When you've got a long to-do list or are simply frustrated with work, there are ways to effectively communicate that with your boss. The key concept here is ditching "no, thanks" language in favor of "sure, but also" statements. Glickman calls it redirecting -- you're happy to take on the assigned task, but you're interested in working on something new and different in the future.

"It probably won't happen immediately, and it's not an 'either-or' scenario -- it's an 'and,'" she says. But if you've got your eyes on an overseas assignment or presence at a client meeting as you sit behind a mountain of data-entry and memo requests, tell your boss that you don't mind the busy work if you get to do the more exciting stuff, too.



When You're Trying to Provide a Quick Update


The times and places you choose to communicate are just as important as the content of your messages. "You might think it's okay to go to your boss every time you have a question," says Glickman, but it's better to ask first if that's their preference before you inundate them with one-line e-mails throughout the day.

"Find out how your boss wants to be communicated with, and then do it," she says. "Do they want you to call with questions as you have them, or would they rather you bundle them up and reach out to them once a day with everything you need them to weigh in on?"

Forward momentum is as important here as it is during goodbyes. "If you go and tell your boss that you've completed a project, they will ask you what's next," she says. "Think about those next steps first so your boss doesn't have to."



When You Have to Explain Something Complicated


The general sharing of information in the workplace is like an omelet, says Glickman. "When you give someone an update, you shouldn't start by telling them about the eggs and cheese or butter and milk," she writes. Instead, you want to "lead with the punchline." Start with the point -- that is, the fact that you have just finished making the most fabulous, delicious omelet -- and then hone in on the details of how you made it and what you put in it, rather than building up suspense and anticipation.

She says that the same rules apply to your personal elevator pitch. "It's all about your destination -- where you're going, what you're excited about now -- not about where you came from and where you've been," Glickman explains. "People are going to be more interested in what you do now and what you want to do going forward before you tell them where you came from. It inverts the order in which most people talk about themselves," she says, but it helps connect the dots between the old and the new much more effectively.



When You're Raising an Issue


Your communication style can make or break people's perception of your ability to manage a crisis or bring attention to a potential issue. "If there's a problem, you have to highlight it as soon as it arises," she says. "Don't hide behind bad news." Glickman says it's about pinpointing the issue, explaining how it might have happened or why it's about to go wrong, and proposing a reasoned solution.

Many people's first instinct when there's a problem is to wait until it surfaces to others to avoid being the bearer of bad news. Glickman says that's the wrong way to think about it. "Transparency is valuable," she says, "but it goes beyond just being honest. It's also being forthright and a person who shares information proactively."



When You Don't Know the Answer


No one knows how to do absolutely everything. When you don't know something, the best way to deal with it, says Glickman, is to be enthusiastic despite bewilderment. "Enthusiasm goes a long way in the face of an 'I don't know,'" says Glickman.

Ask for help intelligently. Follow up a "This sounds like a great assignment, I'd love to help," with a request for an example, a contact recommendation, or a template, Glickman suggests. "If they don't have any guidance, tell them you'll spend some time thinking about it, and you'll come back to them to find out what they think about the direction you're taking," she says. "You want to make sure you're doing what you're supposed to be doing."


In today's economy, being the hardest worker or the most educated in your group isn't a sure-fire guarantee that you'll be scaling the corporate ladder briskly. Business is inherently personal, and if you want to come out on top, you need to not only be good at doing your job, you need to be good at telling people about it.