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EPISODE 0018 - MAY 1, 2018

Ask A Manager

with Alison Green
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Wailin interviews Alison Green, the advice columnist whose Ask A Manager column offers friendly and practical guidance for all kinds of workplace dilemmas, from “How do I ask for a raise?” to “How can I get out of eating lunch with coworkers?” Alison talks about memorable letters, her community of commenters, and seeking advice from fellow advice columnists. Wailin also shares a story about a particularly horrible day at work where she could have used Alison’s help.

Transcript

(00:00:00) Broken By Design by Clip Art plays.

Wailin: (00:00:00) Welcome to REWORK, a podcast by Basecamp about the better way to work and run your business. I’m Wailin Wong.

Shaun: (00:00:07) And I’m Shaun Hildner. I’m very excited today because you told me that you have an embarrassing story.

Wailin: (00:00:13) Oh, I have a workplace dilemma story that happened to me IRL a few years ago. Today we’re going to be talking about workplace dilemmas, so I wanted to share this story with you, and you can tell me what I should have done.

Shaun: (00:00:28) I can’t wait.

Wailin: (00:00:29) Okay. As some of our listeners might know, I used to work at a large metro daily newspaper before coming to Basecamp to take this job. I was a business reporter and there was this one week where I worked incredibly hard and was almost single-handedly responsible for every story in the Sunday business section. I was really looking forward to getting some feedback from my managing editor about all the work I did and what he thought of the stories. And I thought at the very least I would be acknowledged for the Herculean effort I put in to make the Sunday section look really good because I wrote almost every story in there.

(00:01:08) And… nothing. Like, he didn’t say anything to me. I just started stewing a little bit and I decided to write an email complaining about this to my friend Julie who at that time sat in the cubicle right in front of mine. I typed up this whole thing saying I worked so hard on the Sunday section, I wrote all these stories and no one said anything to me. And I remember I ended the email with something like, I am a very special snowflake and I demand to be acknowledged. So I fire off this email to Julie and then like probably less than a minute later, I got a response from another reporter, a friend of mine in the section and she said, “Did you mean to send this?”

(00:02:03) And I realized—

Shaun: (00:02:06) Oh, God.

Wailin: (00:02:06) —that I had not sent the email to my friend Julie, but in fact I had sent it to a shared email account. This was an email address that was shared by every editor on the business section along with a few reporters and also a couple top editors of the entire paper. Like, I think the managing editor of the entire paper might’ve been on that email address as well.

Shaun: (00:02:38) Oh, I am so uncomfortable just sitting here listening to this story.

Wailin: (00:02:42) Well, what happened was I had a full-blown panic attack—

Shaun: (00:02:45) Oh no.

Wailin: (00:02:45) —and I fled to the ladies room. It was funny because I had a stream of visitors. It was like I was holding hysterical office hours in the ladies room and then I decided I would go over and talk to my managing editor. I walk across the newsroom to where his office is, and he didn’t see me at first or hear me. So I did that awkward, little hoppy dance—

Shaun: (00:03:15) Yeah, sure.

Wailin: (00:03:15) —in front of his office door. And he finally looked up and I was like, “Hi, um, I sent this email. I wrote it in anger. I didn’t mean it, please don’t read it. Just delete it.”

(00:03:34) And he just gave me this look that was a little bit quizzical and a little bit annoyed because I had just interrupted whatever he was doing and I realized that he hadn’t even seen the email. So, he just gave me this look and then was like, “Yeah, okay, whatever.”

Shaun: (00:03:49) That’s very lucky.

Wailin: (00:03:50) So lucky. And I just backed very slowly out of his office and that was that.

Shaun: (00:03:55) Amazing.

Wailin: (00:03:56) What would you have done?

Shaun: (00:03:59) What would I have done?

Wailin: (00:03:59) Yeah.

Shaun: (00:04:00) Oh, I would, um, put in my two weeks immediately and never, never come back. Yeah. It makes me super uncomfortable just like thinking about it.

Wailin: (00:04:09) Yeah. I feel like you’re going to quit your job just hearing the story.

Shaun: (00:04:12) Right.

Wailin: (00:04:12) ‘Cause you just don’t want to work with me anymore.

Shaun: (00:04:13) The fear is real.

Wailin: (00:04:15) The amount of secondhand embarrassment I’m projecting on you.

Shaun: (00:04:18) Maybe you wish that there was a place that you could ask for advice on this kind of thing.

Wailin: (00:04:22) That’s right. And so today I was really excited to be able to talk to Alison Green. She is a professional workplace advice columnist who runs the very popular site, Ask A Manager. I mean Ask A Manager was around when this happened to me, but I wasn’t reading it then. Otherwise I think that would have been a really good resource and I would have written in immediately.

(00:04:42) But, Alison also has a new book out called Ask A Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life At Work.

Shaun: (00:04:52) All right, well let’s hear it.

Wailin: (00:04:54) I wanted to start with what you were doing before you did the column because you mentioned in your book that you were the Chief of Staff at a nonprofit lobbying organization and I was wondering what was that job like?

Alison: (00:05:08) Yeah, so I was actually in that job when I started Ask A Manager, and this was a really fun and challenging position, basically doing the day-to-day management of the whole organization. So, making sure that we’re hitting our goals, dealing with hiring, dealing with coaching, making sure that managers are managing their teams effectively and tons and tons of problem solving.

Wailin: (00:05:31) Was providing advice part of your job description when you were still the Chief of Staff or was it just a role that you evolved into you because you are naturally good at it?

Alison: (00:05:42) Well, both, really. So I coached the managers on our staff who are leading their own teams to try to push them toward sounder management practices. And I think too, like many managers who like managing, I really enjoyed the mentorship part of managing. So I think I naturally gravitated toward a mentor type role with people who were interested in it. Not everyone wants that of course, but, I think you see that in a lot of people who really like managing one of the pieces of the job that they like the most is being able to problem solve with people and give advice and kind of step back from the day-to-day rush of the work to talk about bigger picture career issues.

(00:06:22) So I started Ask A Manager, actually in, gosh, it’s been 11 years now. I started in 2007 while I was at that job because I kept seeing people, fellow staff members, and also job candidates, making choices that weren’t getting them the outcomes that they wanted. And I thought if they had more insight into the way a manager or a hiring manager thought they might navigate issues that come up at work differently and get better outcomes.

Wailin: (00:06:50) What did you find were some of the biggest blind spots? Like the top couple of things that employees seemed to not understand about the manager mindset or the way that managers have to operate.

Alison: (00:07:02) Sometimes people are very hesitant to ask for what they want or to speak up when they disagree with a decision or the way a project is unfolding and they just sort of assume, well, if my boss wanted my input, I’d be asked for it. You see this more when people are sort of junior level, but it’s not exclusively confined to that professional stage. And, really if you’re a good employee and you approach things professionally and collaboratively, a good manager does want to know what you want and does want to hear your input. It doesn’t mean that you’ll get what you want every time, or that your input will always be used, but you should at least be heard out and it shouldn’t be a problem that you’re speaking up. It should actually be welcomed and I think the people who have the most successful careers in the most effective relationships with their managers are actually people who, who do speak up pretty freely.

(00:07:55) I think the key in doing it is to frame whatever you’re saying from the perspective of what makes the most sense for the organization and why. Rather than just, I want X, because your boss is going to need to take the perspective of what makes the most sense for the organization. So, if you start there, the conversation is likely to be a more effective one.

(00:08:18) That said, sometimes something really does just come down to I want X and there isn’t anything more to it. And it’s okay when that’s the case, to be straightforward about that. I mean, if you’re in pretty good standing with your boss and you have some credibility built up, sometimes it’s okay to say, you know, I know this doesn’t sound like a big deal, but I would really love it if we could try doing X instead.

Wailin: (00:08:38) Yeah, I mean, one thing that really struck me about the advice that you give in your book and the advice you give every day via your column, is that when you provide some suggested things to say they’re so direct and assertive but they’re also so pleasant. I just feel like that tone is so difficult to hit, where, you’re not making it super personal or super emotional, but you are stating in unequivocal terms what your needs and your wants are. I just find that to be so tricky to do in all kinds of interactions.

Alison: (00:09:13) I think people really struggle with it and you’re right, it’s not just at work, it’s in personal relationships too. I think the tone to use almost all of the time is the same tone that you would use for anything less sensitive, you know, the same tone that you would use to say, hey, I’m having trouble with the software, can you help me figure it out? So, it’s just collaborative. It’s not awkward and emotionally fraught. It’s just, hey, here’s this work problem. Can we figure out how to solve it?

Wailin: (00:09:39) And so what did your company think when you started the advice column?

Alison: (00:09:43) Well, so when I started the column in 2007, I did it anonymously for about the first year. In part because I thought it would be really weird for my coworkers to know that I was running this advice blog. I just thought it would be like a strange dynamic. And then I dropped the anonymity about a year in because the column started getting syndicated by other publications and other publications started asking me to write similar columns for them. And you can’t normally do that anonymously. So, I attached to my name and I thought it would be strange at work. It actually wasn’t that strange. I used to think… are people I work with going to send in their own letters to me? Asking for advice about me? Because, I would do that if my boss were running an advice column. But as far as I know, no one ever did that.

Wailin: (00:10:38) And then, when did you decide that it was time to leave that job and be able to do this full time? Was that a really big transition?

Alison: (00:10:45) Yeah, so it was about three years after I started Ask A Manager, and the site had really taken off. Within a few years I started getting just tons of letters and the traffic was building, and I was being asked to write similar types of columns for other publications. And I had been doing a little bit of management consulting on the side and I thought there’s maybe enough here that I could cobble this all together into some semblance of a business, thinking at the time that the bulk of it would be consulting with other organizations and that the, the Ask A Manager stuff would be just kind of on the side. And, I was pretty sure, I mean it felt like a huge leap. I was pretty sure I would try it for six months and then have to go back to working a normal job because it wouldn’t really work out.

(00:11:33) But, here we are eight years later and it has worked out really well and I am still doing the management consulting, but the Ask A Manager stuff has taken up an increasingly large portion of my time.

(00:11:45) You know, when I started the site, I thought, oh, I’ll just do this for a few months and get it out of my system and no one will read it. And that’ll be the end of that. What I didn’t anticipate was, it turns out, I think there’s a real hunger out there for a place where people can go to ask very nuanced work questions. You know, there’s tons of places where you can go to find out, how do I ask for a raise? Or, how do I write a cover letter? Even like how do I work for a micromanager? But there isn’t a lot of places you can go to ask much more nuanced, personalized things. You know, I’m allergic to my boss’s perfume and she’s very petty about people bringing up any kind of complaint. What do I do? Or, I drank too much at the holiday party and now everyone is giving me the cold shoulder. How do I navigate those? You know, those sorts of very specific questions and that has really become the bread and butter if the site.

Wailin: (00:12:37) So, does the management consulting tend to be a little bit more general, then? You’re coming in at a high level to provide advice on management and mentoring. Whereas, the advice column you are getting the hyper-specific ones, like some of the ones I’ve seen recently was somewhat an employee wrote a memo about ghosts in the building. I mean I’m assuming you don’t get a lot of dilemmas like that to deal with in the management consulting.

Alison: (00:13:01) I do not get a lot of questions about ghosts in the building. That was a great letter. But, you know, a lot of it is very specific questions that managers have that are not that different from the types of managers questions that I answer on the website. There’s just more of them to come in in a series, but most of it is… So, the consulting that I do isn’t what people typically think of as management consulting, where you come in and you observe and you crunch their data and you hand them a bound report at the end of three months. Mine is really, it’s almost more similar to coaching, in that I’m just working through very specific concrete problems with managers that they’re grappling with.

Wailin: (00:13:41) And I’m interested in how your job has evolved over these last 10 or so years. Has the kinds of questions you’ve gotten changed? I mean, I assume some of the principles underlying principles are still roughly the same. You’re looking at communication and you’re looking at how to separate emotional from work and things like that. But are some of the specific scenarios pretty different? The ones that you get now versus the ones you’re getting 10 years ago?

Alison: (00:14:07) You know, there’s a few things that I’ve noticed that have changed. One is the economy. So, when I started the site, it is 2007, so a year later we’re plunged into recession and for many years after that, my mail was just full of very desperate letters from people who were in just a terrible situation with their job search, especially if they had graduated around that time. They graduated into a terrible job market, and really were having trouble getting hired. Or from people who had a job, but it was a pretty unpleasant situation for them. And it was just feeling impossible to leave because the job market was so tight at the time. And that has really changed in the last year or so. I think the, the market has really changed for the better for our, for job seekers and employees. So, that’s reflected in my mail.

(00:14:59) And then I think there’s a few other trends too. One is, there’s been such a move in the last 10 years toward open plan offices where everyone is just in one big room and so, many people hate that. It works for some people, but for a lot of people it’s just a hard environment to work in. There’s so many distractions and you don’t have any privacy and you can’t focus. So, I’ve seen more and more complaints about that.

Wailin: (00:15:21) Have you gotten more questions about navigating tone in chat rooms and other forms of communication that aren’t email?

Alison: (00:15:30) Yeah, like Slack, and things like that. I do see it come up more. I don’t know that the answers to those are that different than they are for email, but yes, certainly changing technology is reflected in my mail.

Wailin: (00:15:42) And, in those 10 years, has your approach to giving advice changed?

Alison: (00:15:47) That’s a great question. Yeah. I think in a few ways. Earlier on I used to be very quick to say, well this is a terrible situation and your boss is awful. You should just—you should leave, you should find a different job and go. Very often, that is the answer, but it can’t be a pat answer. I mean, I think you have to approach it with an understanding that you can’t leave a job every time something is hard. And, people don’t always have the luxury of having enough options that they can leave anytime soon. And so, I do still quite frequently say ultimately, at the end of the day, this situation isn’t going to change and you have to decide if you can live with it or not. And if you can’t, then start thinking about changing jobs. But, I think I have more of an appreciation now that it’s not quite that easy and that people really need advice for the piece of this while they’re still there.

Wailin: (00:16:40) Yeah. Does it force you to be more creative about, okay, here are some things maybe you can do to mitigate the situation if you really can’t leave?

Alison: (00:16:47) Yes, and I think a big part of it is mindset. That sometimes getting really, really clear on why you’re choosing to stay, even if it doesn’t feel like you’re choosing to stay, because you’d like to leave. But you are choosing to show up there day after day and it’s probably for the paycheck or it might be because you’re getting some sort of great professional benefit by being there that will make your job search in a year much easier. Or, maybe you have a great commute. Maybe it’s five minutes to get to work. There’s, always some reason. It’s usually the paycheck, but sometimes there are others. And, if you can get really clear in your head on why you have chosen to make this trade-off, sometimes that can make it more bearable and make you feel like you have a bit more control.

Wailin: (00:17:26) And you have this really interesting section in the book where you talk about how your thinking on the pay gap has changed and the advice you give for women especially. Can you talk about that a little bit?

Alison: (00:17:37) Yes. So, I frequently get questions from people who aren’t necessarily bringing gender into it, but who just say, I’m really upset because I found out that my colleague is making significantly more money than me and we’re doing the same work. And, my answer used to be, well, you can take that as background information. It’s actually very helpful background information to know how much your company is willing to pay for this particular job. But you shouldn’t, when you go to your boss, you shouldn’t reference your coworker salary because they could be earning more than you for all sorts of reasons. Maybe they negotiated better when they are hired or maybe they have more difficult clients or a particular degree that the company really values for example.

(00:18:19) And all of those things are true, but there’s been so much attention paid to the gender wage gap in recent years that, don’t think that can be the answer anymore. If there is a gender disparity there, that has to be part of the conversation. And, so in that case it does make sense to reference what your coworker is being paid when you raise this with your boss.

Wailin: (00:18:37) And how has your relationship with the commenters evolved? Because now you have this extremely active community of people who like to weigh in and offer their advice and are always asking for updates and really get into the stories. What have you learned from them and how do you think you’ve been shaped by them?

Alison: (00:18:54) The comment section has been one of the greatest parts of doing the site. And such a surprise. I mean comment sections, get such a bad rap because so many of them are just terrible. I mean, you never want to wade into comments on like Yahoo News or YouTube. They’re just terrible.

(00:19:13) Somehow, though, the comment section on Ask A Manager has evolved into, for the most part, a pretty civil, pretty thoughtful, smart group of regular commenters. And, it’s such a joy as a writer to be able to get so much instant feedback when you put something out there into the world. They will tell me what they think of it and sometimes it’s good, which is very gratifying. But, sometimes it’s not. Sometimes people disagree and that is really helpful. I mean, I don’t have the market cornered on knowing everything there is to know about workplace advice. And it’s so helpful to be able to hear, oh, I, you know, in my industry this would be really different. Or, I think you’re looking at this wrong because of X, Y, Z.

(00:19:56) So, it’s great to have a group of people who give that kind of immediate feedback. And I think it’s great for letter writers too because they’re not just getting my perspective. They’re able to get the perspective of all of these different people from different walks of life.

Wailin: (00:20:09) Yeah, I mean it’s really remarkable how vibrant and kind the comment section is because I could also envision the comment section of an advice website going south so quickly. Right. But you’ve cultivated something really different on Ask A Manager.

Alison: (00:20:25) Yeah, it’s interesting. And, that’s not to say that it doesn’t still have those moments of judginess, because they are definitely there. But, for the most part, it has a culture of being pretty kind and really trying to act in the interest of the letter writers. So, trying to be constructive. I’ve definitely had letter writers who my response kind of took them to task, because they had done something pretty callous or wrong-headed and they didn’t seem to have any understanding of that. And, for the most part, commenters are pretty good about being constructive in those situations. But not always. There are definitely times where I’ve had to step in and say, you know, hey, this is someone who’s writing and asking for advice and they will never read another word here if they get savaged.

Wailin: (00:21:13) What letters have stayed with you or made you wonder about the people involved after you’ve answered them? Do you ever… are you ever just driving or making a cup of tea or something you’re like, oh, I wonder what happened to that person who wrote me in 2012. I wonder how they ended up.

Alison: (00:21:28) Yes, absolutely. There is one letter years ago from someone who had an employee who was telling her coworkers that she was putting magical curses on them. And, to add to it right after she said it, a couple of them got sick, like seriously sick where they’d missed a week or more of work and so they were freaking out. They really thought she was putting curses on them and the manager writing in was like, how do I even begin to handle this? So, I thought that was fascinating and not the kind of thing that you think is going to come up in your job normally.

(00:22:02) I had one last year that actually went viral cause I think this is just taps into so many elements that people find just frustrating and interesting, from a guy who had been in a relationship with someone, a serious relationship 10 years ago, they’d been living together, and he just completely ghosted her.

(00:22:19) She went away for Christmas and while she was gone, he moved out of the country. He didn’t leave a note, he didn’t—nothing. He just up and left and 10 years go by and he’s at a job and he finds out that the new person coming in to be his boss is this ex who he ghosted 10 years ago.

(00:22:38) And so he wrote to me saying, how do I, what do I do? How do I navigate this? And, that one I thought was just fascinating. I mean, first, the idea of treating someone like that who you are in a serious relationship with 10 years ago and not during the ensuing years, having bothered to reach out and try to repair the damage he must’ve done. And then the karmic aspects, too, I mean, and there’s such a poetic justice there, I think for people who’ve been mistreated by an ex to find out that you’re suddenly going to be their boss.

Wailin: (00:23:08) I remember this letter vividly because it dominated the conversation in my corner of the Internet when it came out, and then a month after the first post, the letter writer sent Alison and update on a situation and addressed some of the criticism he’d gotten from the commenters.

Alison: (00:23:24) I actually was really surprised that he sent in an update because he had gotten so much attention on the Internet from people who were not as nice to him, that I didn’t think he would, would volunteer to come back and talk about it again. So I thought it was interesting that he took the time to send in an update and potentially open himself up to that again. It’s interesting when something goes viral. I never know when it’s going to happen. In retrospect, I can see why that one did. The karma aspect of that I think is pretty irresistible to people. But yeah, it’s interesting. There’s good and bad. I mean I think people think, well it must only be good. Your traffic goes up and you’ve got the ad revenue and those things are all great. There’s downsides too. I mean, you were talking about the fact that the comments section at Ask A Manager has the sort of cultural norms of being kind and civil and smart. But when you have a letter go viral, you get an influx of new commenters who don’t know those norms, who, who can really inject a very different vibe into the comment section for that period of time. So, I had to do a lot more moderation that week.

Wailin: (00:24:30) You’ve now been running your own business for the last decade. Have there ever been times where you’ve wanted advice?

Alison: (00:24:38) Oh gosh, all the time.

Wailin: (00:24:40) And where do you go?

Alison: (00:24:42) I go to colleagues and friends and sometimes family members. I think it’s tough as someone running your own business to find people who have that same experience and can speak firsthand from a similar place. And especially with something like an advice column, like that’s such a weird business. I have a real yearning, actually, to find some way to connect with other advice columnists, because I think there’s so many unusual things that are unique to doing this kind of work that I’m desperate to talk over with other people because… I mean even just stuff like how do you manage your mail? Or, how do you tell if a letter is fake? It’s not a popular enough field that there are resources out there for that kind of thing.

Wailin: (00:25:25) How do you tell if a letter is fake?

Alison: (00:25:27) I just go on gut instinct and I’m never quite sure. I mean I’m sure that I have inadvertently printed a fake letter at some point because I think every advice columnist gets punked at some point and that’s fine. I’m not too worried about it. I figure if it’s useful to someone then that’s still worth doing. But you know, sometimes I’m wondering about the veracity of a particular letter, but I think that’s probably true. So I go ahead and print it and then there’ll be like 10 people in the comment section who say, Oh yeah, the same thing happened to me. So, I think there’s a lot of weirdness out there and sometimes something seems like it can’t possibly be true, but we should not underestimate how strange life can be.

(00:26:09) Broken By Design by Clip Art plays.

Shaun: (00:26:11) REWORK is produced by Wailin Wong, a very special snowflake who demands to be acknowledged, and me, Shaun Hildner. Our theme music is Broken By Design by Clip Art. Alison’s website is AskAManager.org. She’s also on Twitter @AskAManager, and she has a podcast called, you guessed it, Ask A Manager, which you can find everywhere you find our podcast.

(00:26:34) Her book is out now and we’ll link to all of these things in the show notes for this episode, which as always you can find at rework.fm.

(00:26:42) We’ll also link to the viral column about the guy who ghosted on his ex-girlfriend. The next episode of rework will be another mailbag where Jason Fried and David Heinemeier Hansson will be answering questions from you, the listener, and this time we have a very special treat. Alison from Ask A Manager will be weighing in on some of those questions as well. You won’t want to miss it.

Shaun: (00:27:10) Her book—

Wailin: (00:27:10) Is that a weird thing to say?

Shaun: (00:27:11) No.

Wailin: (00:27:11) Okay. I interrupted you, I’m sorry.

Shaun: (00:27:14) Uh, I have some advice with a hostile coworker.

[laughter]

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