From nosy bosses to late-night texts, Ask a Manager has answers for all your awkward work problems

ByJames Dennin

It seems fair to say that workplace drama is more complicated than it used to be. As companies embrace open-air offices, emoji-fied communications tools and after-hours texting, work arrangements have become more flexible, fluid, possibly even more productive. But at the same time, a new lack of formality has also created problems the traditional corporate nine-to-fiver never had to worry about, like whether our emails have the optimal number of explanation points.

Ten years ago, as the chief of staff for a nonprofit, Alison Green noticed these more casual workplace trends. She created Ask a Manager as a destination for beleaguered employees and managers alike to ask the types of questions that might befuddle even the most seasoned human resources representative. In her earnest, often viral question and answer sessions, Green tackles the predictable problems of how to ask for that raise alongside a new era of workplace woes, from racist memes to armpit hair decorum.

Since then, what started as a relatively humble blog about management and human resources — “Honestly, I thought no one would read it,” Green joked in a phone interview — has grown into something of a phenomenon, particularly one widely shared series of posts from last summer following the saga of a man who ghosted an ex-girlfriend, who later became his boss (we recommend starting at the beginning).

To better understand what this brave new world means for workers and the people who manage them, Mic talked to Green about the blog and her new book, “Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work,” which will be released on May 1. The following interview has been edited lightly for length and clarity.

Mic: What were the main problems you wanted to address in the new book? Were there any common themes about what today’s office workers are dealing with en masse?

Allison Green: The underlying question in so many letters I receive is “How do I talk about this thing to my coworker, my boss, my employer?” Within that, there’s lots of specific letters that have been particularly surprising. The weirdest one that did make it into the book was someone whose co-worker wanted everyone to refer to her boyfriend as her “master,” and people weren’t really willing to do that.

What’s the protocol there? What should a subordinate say to the boss who keeps bringing up their sex life?

AG: With that one you don’t want to hint or dance around it. You’re talking about someone who already is not abiding by the social contract, and so it’s OK be very direct and straightforward: “No one wants to hear about that.” In this case it was a little easier to handle — it was a manager who was writing in about their employee, so she had the authority to go in and say, “OK, you can’t ask coworkers to do this.”

If it’s your boss that’s doing it? It really depends on the impact of what your boss is doing. Maybe it grates on you, but it probably doesn’t matter at the end of the day. If someone’s informal in the more personal way, like asking about your sex life at work — which is a thing that happens — then whether to bring it up depends a lot on how often it’s happening. But if she’s really nosy, like she wants to know exactly what’s going on in that doctor’s appointment, that’s when it’s worth pushing back.

Did workers always have to worry about sex talk in the office? Is it safe to say our workplaces have become more informal?

AG: Broadly, workplaces are getting less formal. And when things get less formal, some people navigate that beautifully and other people really struggle to navigate it, and struggle to know exactly where these new boundaries really are. In open offices you can hear everything, there’s not a lot of privacy, and that can send really mixed messages.

Is there anything that workers who struggle with navigating these boundaries can do about it?

AG: One thing that’s so important is to really believe what you see in the interview process. Workers get so focused on “Oh, I just want the job offer,” and they forget to do their own rigorous screening.

Is the hiring manager polite? Is she being kind of rude or tyrannical? Do people in the office seem happy or discouraged and depressed? What am I seeing about how the employer operates? If there are people in your network who work there, try and get a feel of what it’s like internally. Because a lot of companies put on a shiny, happy face.

Why is it so important to ask questions in your interview? How tough should the questions be?

AG: It’s not just about whether they’re interested in you, you want to be actively evaluating them. So often people don’t ask those questions, they think of the interview as a one-way street, which is how you end up in a job you’re not good at or that makes you miserable.

Kind of related to that are people who clearly aren’t doing that kind of rigorous evaluation, that are giving the answers they think the hiring manager wants to hear. They’ll bluff about their skills, or they won’t ask probing questions. On the hiring manager’s side, you want to see that the person’s actually done their research.

If there’s been a scandal at the company, should you ask about it?

AG: You don’t want to do it just for the sake of doing it, but if you have genuine questions, then yes. You don’t want to be adversarial or confrontational, but you should say, “I’ve read in the news about how you’re grappling with X, can you talk to me about how you’re dealing with it internally?”

What about awkward situations for employees? What’s the right thing to say if you drink too much at the office holiday party?

AG: People’s instinct is to just put their head down and hope that no one will notice, and maybe that will work. But if you’re pretty sure you were drunk and it was noticeable, you need to just address it head on. If your boss saw you, definitely say something to your boss. Maybe even say you’re not going to drink at office events going forward. We’re all human, people will cut you a lot of slack, but that slack will expire pretty quickly.

Have you gotten a sense that a lot of workplace problems happen because people are too scared to bring up issues, even if they’re small?

AG: That’s the biggest takeaway I’ve gotten from ten years of Ask a Manager. People are just sort of suffering in silence and dealing with a lot of annoying or aggravating behavior just to avoid a potentially awkward five-minute conversation.

Most people will not hold it against you forever if you initiate that encounter and if you’re polite and non-adversarial. A lot of people dread confrontation and build it up to a much bigger thing in their mind. So asking a colleague to turn down their music, for example, is a perfectly reasonable request — but they picture this tense conversation even though in most cases that’s not how it goes.

How can young workers in particular be better advocates for themselves? Not just in situations like that, but also when they’re asking for more money?

AG: You do want to show enthusiasm. If you’re interested in the job, that’s a great thing to show because hiring managers want people who will be excited about the work. But that doesn’t preclude advocating for yourself.

A good employer is not going to revoke a job offer because you asked for a reasonable amount of money. They’re not going to take you out of the running for asserting yourself in an appropriate way. And if they do, they will be the employers you want to screen out. That’s really valuable information about the employer — that it’s not the job you want.

What’s the right play in a Barstool Sports-like situation, if you think a hiring manager may be testing you by emailing or texting at odd hours?

AG: Set reasonable boundaries. If you don’t want to be dealing with stuff on the weekends, wait until Monday until you respond. If you must, say you were busy all weekend and you’re just getting back to your email today. And then just see how they respond. If an employer tests you that way, that’s the time to screen out that employer.

Let’s end on a nice note. How can employees help good managers be better at their job? If you had an hour at the end of a week to focus on improving communication with your manager, how should you spend it?

AG: Read things that are targeted toward an audience of managers. That gives you so much more insight into what’s weighing on your manager’s mind and what she thinks and what’s important to her. That will shift your perspective in ways that will be really helpful. Try to think about the whole landscape your manager is thinking about.

April 20, 2018, 11:01 a.m.: This story has been updated.

Sign up for the Payoff — your weekly crash course on how to live your best financial life.