Awkward! The blog to ease that horrible office conversation no one wants to have

From the receptionist who can’t stop hugging people to co-workers’ racist Halloween costumes, Alison Green’s Ask a Manager blog takes a boss’s-eye view

Overhead view of four persons working at desk in architects office
‘The most common stuff is: I have a terrible boss, what do I do? I want my co-worker to stop doing this annoying thing but I don’t want to say anything to them about it?’ Photograph: Chris Sattlberger/Getty Images/Cultura RF

Is it OK to have a Christmas party at Hooters? How can I tell my co-workers their Halloween costumes are racist? I accidentally hugged the CEO. How embarrassed should I be?

These are the kinds of questions that often land in Alison Green’s mailbox. Green is the manager behind the popular Ask a Manager blog, which she launched almost 10 years ago while working at a not-for-profit organization in Washington DC and now attracts 2 million visitors a month.

It all happened on a whim, she says. Frustrated with seeing people “both in the hiring process but also internally within the office” make bad choices, Green decided to start a blog.

“The common denominator with all of this stuff is that you don’t understand how your manager or your interviewer is thinking. I thought there is a place to give insight into how managers and how job interviewers think. And really on a whim – my boyfriend had gone out and I was bored – I put together the Ask a Manager blog,” she says. “I didn’t think anybody would read it. I had no idea how I would go about getting an audience. I figured I would do it for maybe three to six months and get it out of my system and then I would be done and move on with my life.”

Yet people did find it. Of the 2 million visitors she gets a month, about half have never visited the site before. “I am not clear on how that happened,” she laughs. “I didn’t do any SEO [search engine optimization] or any of that stuff you are supposed to do to build an audience. I think I got really lucky with the timing. Somehow people found it and started sending in questions.”

Green now receives 50 to 60 questions a day, answering just a fraction. The thing that sets her blog apart, she says, is the ability to answer a question about specific situations with several twists.

“If someone doesn’t read the column, they might think: ‘Work advice? That sounds really boring.’ But when you read it, it’s not really just work advice. It’s interpersonal advice. It’s advice about your own personal issues that are causing problems for you, maybe in your career. That’s so much more interesting than talking about how to make your résumé,” she explains. “There is real hunger out there for a place that people can go to ask really nuanced questions.”

For inspiration, Green draws from Washington Post’s advice columnist, Carolyn Hax.

“What she had done for me is really drill in my head that you have to confront the reality of your situation, not what you wish your situation were,” she says.

When selecting letters from readers to answer, Green often looks for awkwardness. “There is a really uncomfortable thing going on and everyone feels awkward about it and the only way you are going to get it to stop is if you are willing to suck it up and say something that no one wants to because it’s a horrible conversation to have,” says Green.

One of her favorite letters was from someone who worked at an office where the receptionist kept hugging everyone who came to the office. “And not just a quick hug, like a full body-hug where she would hold on for like a full minute. People were really uncomfortable and no one knew what to say to her and they were worried their appointments didn’t want to come to their office any more,” she says. Her advice: talk to the receptionist. Have the awkward conversation and move on.

“Some of the drama is very soap opera-ish. I have a real taste for the weird and so if I get a crazy letter, it goes straight to the top of my list. I love the crazy letters. I always wonder: ‘Am I pushing the balance too far in that direction?’ But people really like it. It makes it so much more interesting. I have people say to me all the time that reading the column makes them appreciate their own workplace and their own boss.”

Much has changed in the job market since 2007 – the unemployment rate went up, then down. Co-working spaces became trendy and the threat of robots taking over our jobs became slightly more real. Yet at the core of it, people still worry about the same stuff, says Green.

“The most common stuff is: ‘I have a terrible boss, what do I do? I want my co-worker to stop doing this annoying thing but I don’t want to say anything to them about it, is there a magic pill?’ Those haven’t changed and probably will never change. There is stuff that changed around the edges. A year after I started we plunged into a recession, and that had a huge impact on the job market, and so the nature of the questions that I was getting for a few years was upsetting and stressful, really. There were people who had been out of work for years,” she says.

“I am still talking to millennials who can’t get job in their field because when they graduated, they graduated into a terrible recession and they have been working at Starbucks for several years and now no one will hire them for the job they got a degree in. I have also seen things getting better post-recession. People are also more willing to leave bad situations than they were in the middle years that I was writing.”

There have been other changes too. There are more questions about telecommuting and perks that disappeared during the recession and haven’t yet made it back. There are also a lot more questions about animal-friendly offices and how to navigate them.

“The most interesting was probably from someone who went to work in an office that was dog-friendly and a bunch of people brought their dogs in and she had really debilitating allergies. The company did not want to work with her on it and legally they had to accommodate her. But people were pissed. People felt like they had come to the company specifically because it was dog friendly and she was ruining it. It became a very hostile environment for her,” Green explains. “She ultimately had to leave over it because there was such a huge clash of her interest against their interests. You can kind of see where they are coming from too – it’s their culture.”

For Green, who at 43 has spent most of her life working at and with not-for-profit groups, doling out advice in a friendly conversational manner – (“It’s sort of like answering an email from a friend,” she says) – feels like working for a cause, “doing good in the world”.

“I think as long as it continues to feel like that, I’ll keep doing that,” she says.