Every Morning, My Boss Gives Us an Unfiltered Look Into His Email Inbox. I’ve Seen Things I Shouldn’t Have.

Good Job Someone needs to stop this. Photo illustration by Slate. Photo by Rawf8/Getty Images Plus and Stanislav Shkoborev/Getty Images Plus. Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily. Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!) Dear Good Job, I work in a mid-size business (about 16 to 20 people on site any given day), and we have a new boss. He’s an older man (mid-50s to 60s), and while he’s very knowledgeable about our sector, he doesn’t seem as well-versed in technology. Every morning we start with a daily meeting where we lay out our goals for the day, what progress everyone is making on their projects, or anything else the teams need to know. This involves a large projection screen connected to a laptop. Every morning, the boss plugs the screen into the laptop, and then has to go into his email to find the instructions to open the company software, and then another email to get the password. He inevitably opens multiple emails trying to find what he’s looking for, and it all comes up on the big screen. We’ve caught glimpses of professional email exchanges that should be private, including about staff members. We’ve also seen some very nasty personal emails with a woman I assume is his wife that really should have been private! It can get extremely awkward. No one wants to give the new boss a heads-up because this guy has a temper. He wants to just get on with his own work and doesn’t like being “interrupted” by staff, even if it’s important. Obviously, he can’t be flashing his private and work emails for everyone to see, but he’s going to need to be walked through the process probably multiple times, and no one is volunteering. What should we do? —Email Flasher Dear Email Flasher, Congratulations on not giggling, snorting, or rolling your eyes whenever your new boss starts a meeting. Even though he’s too oblivious to be embarrassed, I hope you and your colleagues appreciate how this display of incompetence confirms your impressions of him. He’s too proud to ask for help and so temperamental about “interruptions” that no one volunteers to help. It would be tempting to just pop some mental popcorn and enjoy his blundering, but other people could be harmed—nobody wants all their co-workers to accidentally see their performance evaluations. Plus, he’s wasting your time every morning. Does your business have any staffers who handle information technology? If so, ask them if they can figure out a solution. They might be able to set up a simpler system for the projector, automate the process on your boss’s laptop, or just print out instructions that they leave in the room. (That’s not great operational security, but it’s better than what you’re dealing with now.) Could they show him how to log in to the company software before he starts projecting his screen? If there’s no IT department, do you have human resources? If so, tell HR about the security breaches (because that’s what flashing confidential documents amounts to). They might be too intimidated by the boss to intervene, but you can try. If your boss has an assistant (what a miserable job that must be), ask them to offer to set up the projector ahead of the meeting, which they can present as a way to save the boss’s valuable time. Assuming you’re better at operational security than your boss, you could set up an anonymous email account to alert your boss’s boss that the new guy is projecting professional and personal messages for all the staff to see. While you’re at it, document examples of his temper tantrums and anonymously inform the boss’s boss about those as well. Even if your boss eventually figures out how to use the projector, and even though he knows your sector well, his disdain for other people means he’s unfit to lead. Please keep questions short (<150 words), and don’t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication. Dear Good Job, I retired a few years ago from a career that required close attention to detail, expert organizational skills, working well with the public, an adherence to established rules and policies, and a can-do attitude. I was a librarian. Because of these skills, a family friend-in-law asked me to help him out during his busy season as an accountant. I thought, sure, why not make some money during winter and early spring? I hated it, mostly because I had never before experienced a micromanager at his level. He was always walking around like his hair was on fire. On top of that, there was no logical filing system. Had it been extremely difficult to learn, I would have at least gotten used to it eventually. But nothing made sense. Phone calls had to be written down and then entered into an Excel file, and then typed into an email concerning who had called when. A longtime former employee visited once and remarked that it had been this way for at least 40 years. Nothing is digitized, and everything has to be copied in duplicate “just in case.” Some files are full of scraps of paper and can be 200 pages. His office looks like his file drawers exploded. I can’t imagine being a client and having confidence that my information was being curated professionally and carefully. It is no coincidence that his clients have been going there for decades, and they seem as hesitant to change as he is. The pay was fine, and I love a challenge. He’s been hinting that he wants me to come back. How do I set boundaries about how I can work most effectively? I can’t spend three to four months always behind, thinking I did something wrong, and appearing like I cannot learn new ways of doing things. I found aspects of it soul-crushing. Can I say something like, “How do you feel about giving me a month’s head start and allowing me to organize the flow of files from drop-off to final signing?” He will almost certainly say no. The family has told me how much he raves about how I saved him, and how he benefited from my help in the office. —MLS Not CPA Dear MLS Not CPA, Are you sure you want to return to a job where you’re micromanaged, required to use archaic record-keeping systems, and soul-crushed? Extra pay and challenges are nice, but feel free to say, “Thanks for hiring me last year. I learned a lot and appreciated the challenges, but I won’t be able to join you this season.” If he pushes, you can say you don’t have the time or capacity, or mention that you want to focus on some other projects this winter. If you do think it’s worth another go-round, your offer to organize the office ahead of the busy season is generous, and it would pay off many times over for your family friend-in-law’s accounting practice. Sure, it’ll make it a little more awkward to say you can’t work there after all if he refuses, but you can still do so: “Thanks for the offer, but the job is more stressful than I anticipated, and I don’t think it’s a good fit for me this year.” If you’d be willing to work there again even with the chaos, try changing your perspective. Last year, you felt behind, thought you were doing things wrong, and worried that you gave the impression of being unable to learn new systems. This year, you know those things aren’t true. The boss raved about how much you helped the business. If you can tell yourself you’re doing the work just fine, and the hair-on-fire problems are his, not yours, the job might feel less soul-crushing. Thank you, by the way, for sharing your story of applying your skills to a new kind of work. We hear from a lot of people who want to change careers: teachers, nurses, people working in tech, people running a small business, people who want to run a small business. Slate ran a whole series on “Second Acts” careers a while ago. It’s great to hear from someone who tried something new and succeeded … even if it didn’t feel like success at the time. Sign up now for Slate Plus to read all of our Good Job columns for the week. Dear Good Job, When, if ever, is there a legitimate reason for an employer to include a consumer credit report in their background screening process of potential employees/candidates? As a person in the throes of a job search, I thought I’d struck gold by simply arriving at the in-person interview stage. I was also pretty uncomfortable with submitting my government-issued I.D. through an online platform, given the innumerable data breaches happening over the last few years. I recently read in a tech magazine about a case of driver’s licenses for sale on the dark web due to a breach. I can’t help but wonder how secure that image of my ID is going to be, but what choice do I have? I need to work. —Is This Legit? Dear Is This Legit, You’re right to be suspicious. Scams keep getting more sophisticated, and you’ve probably seen plenty of scams that target people who are looking for work (which Slate investigated). Before you provide identification or financial information to any potential employer, make sure they’re a legitimate organization, and if so, contact their human resources department to confirm that the request is real. Employers are required to check your ID and confirm you’re eligible to work in the U.S., but that’s typically done after a job offer. Some also run credit checks, usually for positions that involve financial decisions or require security clearances. It’s discriminatory in practice, and some cities and states have outlawed it, so check whether you’re protected by local laws. Good luck out there, and keep your shields up. —Laura More Advice From Slate My half-brother is marrying the bridezilla from hell, “Denise.” She wants a princess wedding but they don’t have two pennies to rub together so she constantly leans on our local community for freebies. Denise actually went to several restaurants and offered them exposure if they sponsored her wedding… Advice Workplace Jobs