Facing a Difficult Or Awkward Conversation at Work? You Are So Not Alone

The internet loves the age-old tradition of advice-giving, from columns like Dear Prudence and Dear Polly to forums like Reddit where people are on standby to throw in their two-cents on a given topic. Now take one of the most fraught places in which we can exist—the workplace—and you have a fertile area for wisdom.

That’s the opportunity Alison Green saw when she started Ask a Manager in 2007, beginning with missteps she was seeing in the nonprofit where she worked. These days, Green is a management consultant and an author, and takes to her website to tackle roughly 40 questions a week on work-related topics.

In parsing the dozens of questions she receives each week, Green looks for problems that are “useful, entertaining, and interesting,” she says. Naturally, many verge into the territory of the very weird—from dealing with an employee casting curses on co-workers, to a boss forcing employees to sign up as liver donors—but there also are commonplace questions, for instance about dealing with colleagues who don’t quite understand boundaries.

Most of the issues people ask about are really variations on broader themes. One that frequently pops up: how to have a difficult conversation. “People know, ok, I have to have this kind of awkward conversation, but they don’t know how to do it,” Green says. “I really try to lean heavily on saying: Here’s how you say it. Here’s how it sounds like, here are the words you can use that hopefully won’t make this blow up in your face.”

This area has proved so topical that Green has an upcoming book about language to use in about 200 awkward workplace scenarios. It’s titled Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work. Given that she’s fielded thousands of questions on workplace dilemmas, I wanted to ask Green about what managers and employees often get wrong, and how they’ve left her feeling about the state of the workplace. This interview has been edited for clarity and concision.

Quartz: A lot of the workplace questions you’re handling touch on psychology, ethics, relationships, even politics. What does that say about what it’s like to be a manager?

Alison Green: A lot of the things that are most challenging to navigate at work are interpersonal issues. That stuff is hard. People are weird—and we bring our own weirdnesses to the table. I think if somehow you took the interpersonal out of it, this stuff would be kind of close to formulaic. There are a lot of ethics involved. Your boss is asking you to something that’s perfectly legal but you feel icky about, how do you navigate that? Then you throw in that it’s your livelihood. If you say no, do you still have a job at the end of the day? This stuff is really tricky. I think that’s what makes it so interesting.

QZ: Do you shoot from the hip when you answer these questions, or do you have any books or leaders you consult or whose management philosophies you follow?

For legal stuff I’m always looking up the law, because that’s pretty black and white. Beyond that, I’ve done a lot of work on management coaching and consulting. So I draw on that. But a lot of the questions I get are not things where there are sources you can consult. It really is about drawing on experience working with people. Some of it is what’s worked for me, and what I’ve seen work and not work for other people.

Advice giving is a weird art. When I started, I used to caveat everything. I’m going to give you the answer that’s most commonly true, but you have to also factor in what you know about your boss and your coworkers and the place [where] you’re working.

QZ: There are all these unspoken social norms that reflect the culture of an office. It takes a long time for employees to figure out what those are. Learning what’s considered right or wrong in any given office is really challenging for people.

And some people are better at it than others. Some people are helped by their family background, and other people are disadvantaged by their background. If you grew up in a family where most people didn’t hold professional jobs, you don’t pick it up by osmosis, the way someone else might. It can be really tough to learn—which is a gap I hope my site is helpful in filling in.

QZ: What do managers get wrong most frequently?

The thing I see probably most commonly is that they’re not sufficiently direct and straightforward. Sometimes there things they’re frustrated by or that they’re concerned about that an employee is doing or not doing. Instead of just sitting down and having a matter-of-fact conversation with the person, they let it fester and they stew. And the problem continues because the person doesn’t know they’re doing anything wrong, and the manager gets more and more frustrated. By the time they finally have to address it, it’s become a much bigger problem … and the conversation has a much different tenor than it would have than if they’d handled it earlier on when it was a much smaller problem.

I get so many letters from managers who write in about something their staff is doing that annoys them, and the first question I always ask is: “Have you talked to them about it?” At last half the time, probably more, the answer is “No, I don’t know how to say it.” I understand not knowing how to say it, those conversations are hard, but it’s part of the job, you’ve got to do it.

On the other side of the spectrum is managers who treat their staff like they’re robots, who don’t account for human emotions and the humanity of people working for them. Or they think that their only job is to get the work done, without thinking about the fact that, long-term, if you want that work done well, you need good people to be willing to work for you and to stay working for you. They don’t create an environment that good people want to stay in.

Can you turn a bad manager into a good manager?

AG: Maybe. Sometimes. The person has to be open to getting pretty critical feedback, which is hard for most people to do. It seems to be particularly tricky for bad managers to do it. If you have someone who is open to hearing that they’re wrong, and who genuinely wants to get better and is willing to work at it, I think it can be done.

Most people get promoted into management jobs because they were good at doing something else, and then they don’t necessarily get a lot of training on how to manage well, and it’s a completely different set of skills.

Seeing all these questions come in, how does it make you feel about the state of the modern workplace?

AG: It reinforces for me that we are just all very human. You look at your personal life and you see friends and family members mishandling their relationships or not navigating a situation well. We do it ourselves, we’re all human, we make mistakes constantly. And that doesn’t change when we go to work.

I think people sometimes expect their managers in particular to be perfect, but managers are human. Work is just a microcosm of how humanity messes things up in general.