a behind-the-scenes look at how Ask a Manager runs

Recently I answered a question about the behind-the-scenes running of Ask a Manager, and readers said they’d be interested in an opportunity to ask more. So last week I asked people to post questions they were interested in, and here are a bunch of answers.

Note that I couldn’t get to all the questions (there were over 300 comments there), nor do I think you would have the patience to read all the answers if I did, but I’ve tackled 35 of them. Also, some questions were asked by multiple people with slight variations, so in some cases I’ve combined multiple questions into a single one.

1. How do you decide which questions get posted on the blog? I imagine you have a lot of submissions to go through! What factors decide the ones that get answered publicly?

It’s a mix of what I find interesting, what I think other people will find interesting, whether I feel I have something useful to say, and what the mix of questions has been recently.

Sometimes, too, it’s just what I feel like answering when I sit down to write. If I’m really busy that day, I might go for something short or easy. Or if I read a letter and immediately start writing the answer in my head, I try to commit that answer to paper (well, screen) right away because writing is easier when you don’t ignore that impulse. So what speaks to me when I sit down to write plays a role. I writing a lot each week, and letting myself choose letters that way makes the volume more sustainable.

2. How many questions come in a day?

About 50 letters per weekday (much fewer on weekends – probably because people aren’t thinking about work as much then). That number has fluctuated a bit over the years; at one point pre-Covid it was as high as 75 a day, but it’s stayed around 50 per day for a while.

3. How much time usually goes by between when someone submits a question and when you publish a response?

It varies wildly. Sometimes it’s really fast (within a few days) and sometimes it takes weeks or months.

My backlog is large and I don’t answer in the order things are received. Sometimes I’ll mark a question as one I definitely want to answer, but I don’t get to it for a while (meaning weeks or even months). If you look at the math – 50+ questions per day is 250+ a week, and I answer about 30 a week here – there’s no way to publish quick responses for the majority of them.

4. How often do you respond to letter-writers when it doesn’t end up on the site?

A lot! If I can send someone a quick private response, I’ll try to do that (even if it’s just a link to a previous post that might help). I used to try to do that for every letter but that got overwhelming pretty quickly. I still try to do it when I can, but the overall volume means that more questions don’t get answered than do.

5. How do you handle time-sensitive letters, like the ones where someone has to have a conversation with their employee within the next few days (or sooner) of submitting the letter? Do you ever send an answer privately back to a writer so that they can use the advice right away, and then you can publish your answer a few days later?

Yes! Sometimes I send a quick private answer right away and then write a longer one for publication when I have more time. Or if I already have that week’s content written, I might send the person a response privately and then publish it at some later time.

But there’s also no realistic way to do time-sensitive answers to everything that would need them. In many cases, I will write an answer at whatever point I get to it, figuring that even if I’ve missed the writer’s deadline, hopefully it will be useful or interesting to other people.

Key to all this is that the purpose of an advice column isn’t primarily to provide individual people with answers (if it were, advice columnists would just answer everyone privately). The audience is much broader than that, and I think every advice columnist picks letters and their timing based on what makes sense for the column and the columnist, not by a strict hierarchy of letter-writer need. (I’ve accepted that if I did it differently, I’d burn out and then be answering no one, and I’d guess it’s the same for other people doing this work.)

6. What makes you decide NOT to answer a letter?

A big reason is if I don’t have a useful answer! Sometimes I think it can be interesting to write an answer that says “you know, I’m not sure and here’s why” … but sometimes that wouldn’t be particularly helpful or interesting to read.

Another is when someone writes in on behalf of someone else (like a friend or a partner) and it doesn’t seem like they have all the details. Or when I’ve done similar topics recently. Or if something is very esoteric, to the point that it’s unlikely to be useful or interesting to anyone else (in that case, I might try to send a short answer privately if I can). Some things are incredibly esoteric but still likely to interest other people … but not all of them fall in that category.

7. Is there a letter topic that used to seem very common but is less so now? Conversely, topics that feel prevalent now but were almost never asked in the early days (disregarding clear time-bound issues like Covid concerns before 2020, etc.)?

Interestingly, I used to get a ton of questions about how to follow up on a job application or interview, and I get far fewer of them now. I’m not sure why that changed!

I definitely get more letters about outrageous/weird situations now than in the early years. I think that’s just a function of the site having a larger audience.

8. Do you have the questions and answered prepared and automatically set to post at certain times of the day? How far ahead do you write the responses? Meaning, are the responses for this week and next week all ready to post, or do you write a day or two ahead?

Yes. Everything is written ahead of time and set to auto-post on a daily schedule. The schedule is midnight, 11 am, 12:30 pm, and 2 pm ET Monday through Thursday. On Fridays, it’s midnight, 11 am, and 12 pm ET.

I usually write anywhere from a few days to a week ahead. The midnight short-answer posts usually get written only a day or two ahead, and other things usually have a little more lead time. (And then for updates month in December, I set everything up in November and then it just auto-posts all month long.)

9. Do you choose the pseudonyms used in the letters, or do people write their own? I always enjoy when there’s a theme to the names used (like TV characters), and I’m curious if that comes from you or from the letter writers themselves.

Usually any names in a letter come from the letter-writer. However, sometimes people don’t use any names at all and I’ll add names if I think it makes the letter easier to follow.

10. How do you decide when to email someone back for more clarification, vs. answering the question “as-is”? How often does this happen? Do letter writers generally respond when you do? 

I don’t do it often. When I do, it’s usually because it’s a really interesting letter that I’d like to answer but after reading it I have a question that feels central to the answer. Or I’ve started writing a response and then realized, “Wait, there’s a key thing I need to understand before I can continue.” I think people nearly always respond when I write back for clarification – it’s at least 99% of the time if not 100%.

11. How much editing do you do to original questions? Is it just spelling and grammar, or do you also edit for anonymity if the submission has personal info?

I edit for spelling, grammar, clarity, and sometimes length.

I will sometimes take out details that seem identifying, especially if they’re not essential to the question (like the name of the city where the person works or a very specific job title or field that won’t affect the answer).

12. Do you come across any questions that you don’t feel qualified to answer? What do you do with those questions?

Yes, definitely. If I can, I’ll suggest somewhere else they could try instead (often that’s a lawyer). But otherwise that’s part of the group of questions that don’t get answered.

13. It seems like some people send their letters to multiple advice columnists and so we’ll see it appear here and in Dear Prudence and AITA, etc. Does it bother you when people do that?

Nah. There’s no guarantee that you’ll get a response at all when you write to an advice column, so I can see why people might submit to multiple places in the hopes of getting an answer.

14. What is your approach to inquiries which seem too ludicrous to be true? Do you assume that all questions are legitimate?

I assume all advice columnists get trolled sometimes, and I’m sure I’m no exception to that. If I think something is absolutely, unquestionably false, I won’t print it, but otherwise I’m not terribly concerned as long as the answer might be useful or interesting to others. As another columnist – Carolyn Hax, maybe? – has said, “Every letter is hypothetical to everyone reading except the one person who sent it in.”

And I do think some of the stranger letters are still good opportunities to provide useful advice that can translate to less bizarre situations. For example, the letter about the employee who was putting magical curses on other employees – you’ll hopefully never be in that situation, but you might need to deal with an employee who is being threatening toward their colleagues in more mundane ways, and that column at its core is about how to deal with that. I like that approach in general – I think it’s useful to be able to say, “Okay, this is weird, but what’s really the crux of the problem, and how do we talk about that?”

15. Have you ever changed your mind about your advice when the letter writer added more detail in the comments?

Definitely! It can be really hard to know to know what details to include when you write to an advice column. You might pick a detail that perfectly encapsulates the situation to you but which sends everyone reading it off on a wild goose chase. Or you might not think to mention something that ends up being really important. It’s really common to be so caught up in the situation that you figure X is shorthand for Y that everyone will understand, and you don’t realize that it’s the wrong detail to capture that until it’s too late. So yes, sometimes when writers offer more info in the comment section, it can really change things — that’s just an inherent limitation of the format.

16. Are there “best practices” you recommend for asking questions? I’m sure you have to balance what’s entertaining with what’s helpful and what’s broadly applicable to other readers. Should we be really specific to our own situation or try to be vaguer so the Q&A could be more relevant to others?

Be more specific than vague. So often the details of a situation will be crucial in figuring out what next steps makes the most sense, and questions that are overly broad can be hard to answer for that reason. I can always edit out detail if it seems excessive.

17. Has there been an overall shift in the subject matter of the questions? I sense that it started out more about how to get jobs and now seems to be more advice on dealing with different situations within jobs.

I think I still receive around the same number of questions on job-searching as I always have, but I answer fewer of them, just because I’ve answered the job-searching stuff so often (although new variations are always interesting) and the other stuff is often more compelling to me.

18. Do you keep any kind of demographic data or are there any patterns you notice in your letter-writers?

Google Analytics gives me a bunch on readers, although I don’t know how accurate it is. For example, it says that last year, 75% of site visitors were in the US, 8% were in the UK, 7% were in Canada, 3% were in Australia, and the remainder from other countries (with the next highest portion being from New Zealand, then Germany, then Ireland, then the Netherlands). It also says 77% were female and 23% were male (not terribly surprising since advice columns in general tend to skew female). And it thinks 36% were age 35-44, 32% were age 25-34, 12% were 45-54, 11% were 18-24, 6% were 55-64, and 3% were 65 or older.

19. I thought I saw a graph posted here a few years ago showing the increase in visitors to the site, almost from its year of creation. Could we see some visualized statistics again about visits to the site?

Here’s a chart of year-by-year traffic.

20. Have you ever had letters where you’ve wanted to contact the person’s company or a news site for them?

Yes! I did contact the media about this letter, with the writer’s permission, and it did lead to some news coverage. I’ve also connected a handful of other writers with reporters so they could talk to them directly (after reporters contacted me wanting to write about those people’s situations; I then check with the letter-writers to see if they want to be connected), especially in 2020 (when a lot of reporters were interested in companies’ bad behavior during Covid).

21. Why do you bundle small questions together into the daily five-questions posts? I’ve always found these hard to follow: The comments get jumbled, and it’s hard to remember who was OP2 vs. OP3 and so on. By posting each answer separately, you’d have more ad impressions and more updates throughout the day to attract readers. Plus, it would be easier to link back to specific questions, and to remove a single question when needed.

I don’t know if my decision on this is the right one, but my reasoning is that those posts contain a lot of questions that aren’t meaty enough for a standalone post, but work well when combined with a few others. Also, making them each into their own separate posts would mean eight posts a day, which feels like a lot to push at readers. I agree it’s not always ideal for the comment section, but commenters are only a small fraction of total readership so they’re not the only thing I need to consider. All that said … I could be wrong! It’s just what feels logical to me.

22. How do the “you may also like” links at the bottom of posts get chosen? I’ve been wondering this forever. I assume there’s some kind of algorithm, but what is it matching on? Are you tagging keywords behind the scenes to make it easier?

It’s done through a WordPress plugin that generates the posts listed there by matching on title and content. However, I can manually override its selections and put in my own, which I sometimes do.

23. When letter-writers send you updates, how do you match it to their original letter? Do you match email addresses?

I match email addresses. Occasionally someone is writing from a different email address and then I try to match names. Sometimes I haven’t been able to, like with really common names, and then I write back to the person and ask if they can link me to their letter … and then once I know the specific letter, I check to make sure the names are the same in both emails. (So far it hasn’t happened that they’re not, but if it did, as an authenticity check I’d ask if they could tell me the email address they had written from originally.)

24. Have you ever considered switching from ads on the site to a Patreon- or donation-based revenue stream?

From a financial perspective, it doesn’t make sense because the ads bring in more revenue than the other options would.

25. Occasionally, you collaborate with other columnists. How does that process go? In addition – is this a live interview or an email exchange? Seems like it would be a lot of work to transcribe a conversation.

With the exception of the podcast, it’s always been in writing. For example, when Jennifer at Captain Awkward and I have answered questions together, we’ve usually done it in a shared Google doc where we can both add our answers and “talk” that way. Or when Harris at Dr. NerdLove quoted me last week, he sent me an email, we had some back and forth, and he pulled the quote he used from that.

26. Is this truly a one-woman operation, or do you have assistants? If so, what do they do? Do you have help for tech support, ads, marketing, etc.?

The bulk of it is a one-woman operation.

I have an excellent part-time tech person who keeps things running behind the scenes. That’s a bigger job than people probably realize; as the site has grown, its technical needs have become a lot more complex and things that were easy to manage when traffic was lower are more complicated at current traffic levels, with more pressure on the server and databases that keep things running. I also work with a company that manages the ads. That’s it!

27. If money were no object, what tasks would you most like to outsource to someone else?

Comment moderation. It doesn’t make financial sense to hire someone to do it, but I’d love not to have to do it myself. Also, possibly SEO, which I know very little about and spend no time on. The site has done fine without it, but if money were no object I’d hire someone to do it and would be curious to see what kind of results they got. It would also be nice to pay someone to do the projects I’m never going to get to – things like creating a site FAQ or pulling together more “best of” compilations like this one.

28. Are there any plans for an update to the comment system to improve the user experience — for example, adding features like being notified if someone replies to a comment one has made?

That’s a good example of the sort of thing I mentioned above that that were easier when the site got less traffic; we used to have exactly that feature and then it broke under the weight of the traffic once it grew. Trying to fix it broke other things.

Every so often I do look around to see if there’s a better commenting system available, and every time I am surprised by how limited the options are unless you’re willing to (a) pour major money into it or (b) compromise people’s anonymity. Right now the one we’ve got is the best of the options, given the various constraints in play. I definitely wish it had more flexibility though.

29. I’m sure there’s a lot of work that goes into running the site that we don’t see, beyond writing answers and posting them. Can you talk about some of the other work you have to do behind the scenes?

• Reading and responding to emails
• Keeping emails organized and categorized so they’re not in chaos later when I’m pulling things out to answer
• Tech stuff – everything from figuring out why the site is suddenly running slower than normal, to talking to my tech person about something that has stopped working or an improvement I’m hoping we could implement, to dealing with an issue with my web hosting company, to solving an issue with the email newsletter, to investigating and responding to tech problems that readers report, to dealing with major outages (some weeks nothing falls in this category and other weeks it can take up an enormous amount of time)
• Working with my ad network (reporting bad ads, tweaking ad configuration, etc.)
• Lots of little tweaks to the site – adding links to updates from the original letters, keeping the archives page updated, fixing broken links, etc.
• Sending people links to my response when their letters have been answered
• Comment moderation
• Managing the AAM Facebook and Twitter pages
• Working with sponsors on sponsored posts
• Doing occasional interviews with journalists who are writing on various work topics
• Sending takedown notices for (rampant) copyright violations

But writing answers is the most time-consuming work.

30. What work are you doing in addition to AAM now?

I do management consulting, mostly for nonprofit managers. For many years I did that work through The Management Center, helping to teach managers how to lead teams – everything from how to hire well, delegate work effectively, give useful feedback and develop people’s skills, address problems, build cultures that support high performance, and much more. One of my favorite things I did there was to create and run a management hotline, where managers could call and get advice on challenges they were dealing with, and I’ve made that a big part of what I do with my own clients now – real-time “let’s work through this very specific problem you’re grappling with.” I also write regular columns on workplace issues for Slate and New York Magazine.

31. How do you keep up with changing professional norms, both in hiring and more generally?

The consulting work I do keeps me pretty steeped in it. It also doesn’t hurt to read hundreds of letters a week from managers and employees about what’s going on in their workplaces! But that’s always a question that’s on my mind, especially because I’ve been trying to decrease the amount of client work I do. And definitely if my advice here stops resonating with people, that’ll be a sign the site has run its course.

32. Did you ever have any nervousness when you first started off, like “am I the right person to be giving this type of advice?” To be clear, I think the blog is amazing and your advice is spot on, it’s just that any time in my career I’ve considered taking a leap, especially to something a little different like trying to get into consulting, I’ve worried that I’m not “enough” of an expert or that other people won’t think I am, and I’m wondering if you’ve ever faced those kinds of thoughts and how you worked through it?

I absolutely had doubts! I’m not a perfect manager or a perfect employee. I’ve made a ton of mistakes! I think that often helps in advice-giving though; mistakes are how you figure stuff out. And sometimes recalling what my own thought process was that led me to a mistake makes it easier to spot when someone else is heading for the same land mine, and to try to steer them away from it.

But yes, it’s weird to hang out your shingle and announce that you’ll give people advice because, as you say, who is anyone to decide they can do that? It’s one reason I try as much as possible to explain why I’m advising what I’m advising – I want people to be able to see what my thought process is so they can decide if they agree with it or not.

Something that has been key to me feeling good about continuing with the site has been the people writing back in and saying, “Hey, I took your advice and it worked and things are better now.” If that stopped, I would rethink things. So with your own leaps, you might think about what signs you can look for that will help you know it’s working or not working.

Also, in case this helps you decide to leap, I think it’s so normal to feel the kind of trepidation you describe (and I worry a lot more about people who don’t feel any).

33. I would love to know how you organize and manage your inbox. Are you in inbox-zero person? Do you have staff to help you read and flag questions? Do you sort questions into potential categories or types? Flag others for long answer vs short answer? Multiple folders to organize ones you’re answering vs ones you are not? I am a huge nerd for organization and knowledge management, would love to hear how you approach, filter, and respond to the deluge of questions you no doubt receive.

I use an entirely different email program for AAM mail than for my regular email, so it stays in its own separate area. Everything I think I might want to answer stays in my in-box and gets a tag of some sort – different ones for short-answer posts, standalone posts, “ask the readers” posts, high-priority letters that I want to answer in the next batch, and so forth. That way it’s easy for me to see what’s available to choose from when I’m writing. I put updates into their own folder so they’re all in one place when I want to do an updates post.

I do that all myself, because the process of sorting through everything that comes in feels so valuable. Not only do I want to use my own judgment to decide what I’ll answer, but it’s so useful to see trends in questions, even ones I don’t answer. I think if I let someone else filter the mail for me, I’d have much less of a view into what’s happening out there and what’s on people’s minds.

34. What has changed in the time you’ve been doing this? I know the answers have felt more pro-labor over time … and I know that my own feelings have followed that same progression. Is that just the reaction to the way the world is or were there things that specifically triggered that change?

A decade and a half of reading my mail, for one thing – you can’t read years worth of letters from people being screwed over by their employers and not have that affect your thinking. (Or if you can, you should not be in this line of work.) That accelerated during the pandemic, when some companies’ choices made the cataclysmic effects of capitalism on workers really stark.

Also … personal growth. When I started the site, I was writing from the perspective of someone who the system had more or less worked for, and I believed more than I should have that what worked for me would work for others. Now I’m much more aware of all the people who it doesn’t work for, and all the reasons why, and I hope that’s reflected in what I write here (and I hope I will always be a work in progress too).

35. Can you please please give us a profile complete with photos on each of your cats please?

Yes, let’s get to the important questions!

Olive

Almost 10 years old, the grande dame of the house. She is very beautiful and requires that you treat her like a queen. She will hiss at you for absolutely nothing and then rub against your hand a few seconds later. She loves my husband.

Eve

Almost 7. May not be a cat; seems more like some strange little creature you might find in a forest or visiting from another planet. Very scampy, full of energy, lives life by rules no one but she understands. Has monkey-like climbing abilities, is a skilled parkour enthusiast, and likes to chase and be chased. Believes deeply that might makes right.

Sophie

Almost 5. Very smart, loves affection, prefers to be cuddled up against someone at all times. (Unfortunately her body is a small furnace.) Likes to stare way too intensely at people and animals she doesn’t know. Will politely tap you when your attention is required. Extremely chonky. Bonded to Hank. Was a teenage mother to Wallace and kept the two of them alive on the streets until a kind person rescued them.

Wallace

Almost 5. An affectionate goofball, but also a distinguished gentleman. Loves to fetch. Fell into the bathtub last week and had his dignity injured. The friendliest of the crew to human visitors, and functions as the welcome wagon for any new cats and helps them feel at ease. Sophie nursed him until he was almost full-grown, a la Robin Arryn.

Laurie

Believed to be 5-ish. Shy with humans but loves other cats. However much love you’re picturing, it’s more. Spent months meticulously plotting to become Eve’s friend; pulled it off and is now the only cat permitted to curl up with her. Took me months to gain his trust and whenever I thought I finally had, he would randomly act like he’d never seen me before. Now loves to flop over and kick with joy. Named after the neighbor boy from Little Women. Bonded to Wallace.

Hank

Believed to be 5-ish. Deeply sensitive and full of love. My husband, who is his soul mate, says, “His eyes reflect depths of emotion beyond human ken, and has a plaintive meow that approaches supersonic. Has Jon Snow level brooding if he feels affronted (exactly what affronts him is still being studied and collated). At all times desires either affection or a heavy blanket to doze under (has a cozy snore). Loves a warm hand on his belly.” Bonded to Sophie.

(Olive, Eve, Laurie, and Hank were foster fails. Sophie and Wallace are from a rescue group.)