weekend free-for-all – November 17-18, 2018

We are the new cats!

This comment section is open for any non-work-related discussion you’d like to have with other readers, by popular demand. (This one is truly no work and no school.)

Book recommendation of the week: Evergreen Tidings from the Baumgartners, by Gretchen Anthony. A very misguided matriarch grapples with change in her family while writing cheerful Christmas letters.

can I refuse overnight business travel?

A reader writes:

Our company is switching software for our management systems. We have two locations in our area, and the company is telling us that we are to close our offices and all of our staff are required to travel three hours away with two overnight stays to be trained on the new system.

This seems unreasonable to me. We all have families and personal obligations. We will be training with coworkers from this other city who get to go home each night. We do not work in an industry that typically requires business travel so none of us agreed to travel when we accepted our jobs. I realize to many it may not seem like a big deal but to parents with small children and people with pets, this seems unfair. It does not seem reasonable that we have our lives hijacked for three days and two nights. Can it really be more cost-effective to pay for travel, meals, and hotels for five people? Five people who are angry and disgruntled about having this hardship placed on their lives in order to keep their jobs? It really does not seem fair.

I answer this question — and four others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

  • I think my manager is trying to push me out of my job
  • Can I stay in my boyfriend’s hotel room during his team-building trip?
  • My former employer won’t let me back to pick up my belongings
  • Can I ask a resigning employee to leave more quickly?

send me your office holiday stories and questions

I’m working on an upcoming holiday-themed episode of the Ask a Manager podcast, and I want to include your stories about holidays at work: gift exchanges gone terribly wrong … holiday party disasters … the time your boss got drunk at the Christmas potluck and passed out on the copier … Whatever funny or weird stories you have about holidays at work, I want to hear them.

I also want to answer any questions that you have holidays in at work – like whether or not to give your boss or your coworkers a gift, how to get out of working New Year’s Eve, whether you really have to attend the office holiday party – whatever you’re wondering about, send it in.

To submit your stories and questions for the show:

1. Record a sound file on your phone and email it to podcast@askamanager.org.

2. Record them on the show voicemail by calling (855) 426-9675.

Thanks!

open thread – November 16-17, 2018

It’s the Friday open thread! The comment section on this post is open for discussion with other readers on anything work-related that you want to talk about. If you want an answer from me, emailing me is still your best bet*, but this is a chance to talk to other readers.

* If you submitted a question to me recently, please don’t repost it here, as it may be in the to-be-answered queue.

am I a party pooper, can I ask a company to speed up its hiring process, and more

It’s four answers to four questions. Here we go…

1. Am I a party pooper or is this weird?

My company of about 200 employees has a new C-level head of one of our departments. I’m in a different department that works closely with his. Since he started a few months ago, every other week or so he treats his department to something. Sometimes it’s a pizza lunch for everyone, but other times it’s way beyond that; he buys concert tickets for anyone who wants to go to a show with him, takes his whole department out for karaoke and paying for rounds of drinks for everyone, etc. For better or worse, we’re a very laid back company, so the drinking and concerts isn’t unusual for employees to do with one another.

However, his department is 50+ people and he pays for all of these things out of pocket, with no endorsement or reimbursement from our company. He only invites employees within his department. To me, it feels like a perk or benefit being given to a certain set of employees and excluding others. And even if I was in his department, I don’t think I would feel comfortable with him buying me concert tickets out of pocket. The whole thing just seems like he’s trying to buy his employees’ favor. Others in my (much smaller department) view it as a nice way to raise his team’s morale, and that because of the age difference (he’s in his mid-50’s, and the rest of our company averages late 20’s/early 30’s), he’s just trying to seem “cool” in an ultimately harmless way.

Is this something that I’m right to feel weird about? Or is this normal, and I’m overreacting and being a party pooper?

Nah, it’s a little weird. It would be one thing if this were a small team and he were doing it only occasionally — but every other week with a group of 50+ is a huge amount of people and a high frequency. And because he’s paying for it himself, it’s going to seem to at least some people that he’s trying to buy his employees’ favor, as it does to you — and raises the question of why just being a good manager doesn’t feel like enough to him. It’s also going to make some people resentful at what may seem like frequent social demands on them; no matter how laid-back he is about people attending, some people are going to wonder if it’ll look bad if they never participate. (Although I don’t think the part about him only offering it to his employees is a big deal; it’s pretty normal for managers to only do stuff for their teams.)

I know it might seem curmudgeonly to criticize someone who’s trying to do nice things for his team. And his intentions are probably very kind! But managers have to think about the broader ramifications of what they’re doing.

That doesn’t mean this is outrageous or unacceptable or anything like that. And hell, some people might love it. But you’re not wrong to feel a little weird about it.

2. My office has a mandatory employee-spouse dinner — but I’m separated

I’m an attorney in a small office. Every year, the partners plan a dinner for lawyers and their spouses (everyone is married), and attendance is absolutely expected. It’s usually planned months in advance so that everyone, including spouses, can clear their schedule to make it. I just got the email with possible dates in January.

Alison, my husband has been staying elsewhere while we work through stuff in our marriage. I’m keeping it quiet — I’m pretty private anyway — and I DEFINITELY don’t want to discuss my separation at the office while things are still so unsettled. How do I respond?!?

Explain that your husband had a last-minute work emergency or family emergency that he needed to attend to and is sorry to miss it. You’re allowed to create polite cover stories in situations like this, where people aren’t entitled to know the real situation. (And frankly, “He has some urgent family stuff going on that he needed to deal with” is true.)

3. Can I ask a company to speed up its hiring process?

I applied for a job at a small company (15 people) during the end of September. I had a first interview two weeks later, but the second interview took a month to schedule. I’m a remote candidate, but will be in town during the first week of December, so they want to schedule an third interview then. They’ve just gotten back to me asking me to potentially also be available for additional interviews in January. At this point, I would have been in process for four months. They have already told me that they don’t want anyone to start until January. I’m fine with this, but my current contract ends in November, so I do want some certainty about what’s going to happen rather than not knowing through the holidays. How much can I push back and ask them to make a decision in December?

You can’t, really. They get to hire on whatever timeline works for them. That said, if you have constraints of your own that would impact your ability to accept a later offer, you can certainly mention that — but that would be stuff like “I have an offer from another company, but you’d be my first choice. Is there any way of expediting our conversations so that I’m able to give them an answer by December 15?” You can’t do that, though, if your reason is just “I don’t want the uncertainty over the holidays.” (And you definitely shouldn’t bluff and make up any external constraints, because they may say, “We understand, and since we can’t move that quickly, you should take the other offer.”)

The best thing you can do here is to assume that you’re not getting an offer from them and proceed accordingly — which presumably means continuing an active search. (That doesn’t mean that you won’t ultimately get an offer from them, just that you can’t count on it and it’s dangerous to plan as if you can.) It does suck to not know, but that’s the nature of job searching, and you can’t insist that they move faster just to make it less stressful for you.

4. Should I say something about my overly chatty employee possibly bothering a coworker?

I supervise a group of part-time workers doing what amounts to unskilled menial labor. One of the workers, Kent, is an older gentleman who has been doing this job for decades. He is known to be very chatty and a bit of a character. Everyone kind of groans internally when they see him coming because they know they’re in for a 15-minute diatribe on the weather and what kind of wardrobe it calls for.

Another of the workers, Aaliyah, is a (30-something?) woman who is no shrinking violet. They work the same shift all week. Lately it hasn’t been very busy, so there is downtime and Kent seems to spend a lot of it following Aaliyah around, chatting at her. On the one hand, I’m sure this is very annoying, but on the other, she is a full grown woman who knows how to take care of herself and all of the work is getting done. Is this something I should intervene in? I don’t get the impression that his talk is inappropriate, just constant. If anything, this woman is more of a bad-ass than I am so I don’t think she needs me stepping in for her, but maybe the work context changes things?

Yeah, the work context changes things. You see someone you supervise following someone around chatting at her, in what looks like an annoying way. Even if Aaliyah is perfectly able to handle this herself, it’s worth checking in with her and saying something like, “I’ve noticed that Kent is spending a lot of time chatting with you recently. Are you fine with that, or would you like me to talk to him about giving you some space?” Who knows, it’s possible that Aaliyah will tell you that she doesn’t mind Kent. But it’s also possible that she’d like him to stop but doesn’t want to make him feel bad or come across as rude herself or thinks his decades of work there mean people are supposed to defer to him, and that she would be grateful for you to step in. (Even bad-asses suffer from that problem on occasion.)

There’s also the question of whether you want Kent doing this, even if Aaliyah doesn’t mind. Is it worth talking to Kent about giving people more space in general? I can’t say without more context, but if you’ve got an employee who’s regularly annoying people, you do have standing to ask them to rein it in. (Within reason, of course. To some extent, we’re all going to need to work with people with odd quirks, annoying personalities, etc., and we shouldn’t demand that people sanitize themselves to the point of perfect uniformity. But if he’s routinely annoying or distracting people, that’s something you can and should bring up.)

an overly cheerful executive keeps ordering me to feel great

A reader writes:

What’s the polite way to tell a coworker to stop ordering me to be happy? Recently, I had a very painful thing happen one morning before work. I cried on my way in, but by the time I got there I had cleaned myself up and looked normal, though I was still hurting. No one noticed I was any different, but one of my executives (she’s not my direct boss, but she is senior to me) is an overly cheery person. She’s the kind of person who will come by and tell someone to smile because “it’s not so bad.” Or, if she asks how I’m doing and I say “I’m okay,” she’ll say “Just okay?! Surely you’re fabulous, right?!” Even though I find her a tad annoying, I usually go along with her.

But I don’t know how to deal with something like that when I’m going through something in my personal life and I don’t particularly feel up to it. I can perform my job duties, remain pleasant, and keep my crying to a minimum (like I said, no one even noticed anything was wrong with me), but how do I tell someone to back off and stop urging me to be cheerful? Is there a way to say, without having to dive into details about my personal life, “I’m going through something right now, so could we lay off?” (Especially when that person is senior to me.)

Ugh to this and all who say it: “Just okay?! Surely you’re fabulous, right?!”

What is up with people who feel the need to order others around them to perform a visual representation of cheerfulness? Why can you not be absorbed in thought / thinking about something serious / reflecting on something upsetting / focused on work and not on shooting beams of sunshine into the room / grieving a death / feeling ill / worrying about your rent / worrying about a difficult assignment? Why are these people uncomfortable with expressions that are simply neutral/thoughtful/focused/tired/worn/human?

The men-ordering-women-to-smile version of this is particularly offensive in its sexism (and note that men rarely if ever tell other men to smile), but your colleague’s version of this is highly irritating as well.

Frankly, it would be a great service — to her and to everyone she interacts with in the future — if you did reply with something that makes it clear that This Is Not The Day For This, Jane.

Some options:

* “Sometimes I’m not fabulous, no.”
* “I just had some very upsetting news.”
* “No, but I’d rather not discuss it.”
* “I’m dealing with something I’d rather not get into.”
* “I’ve just had terrible news.”
* “I’m sure you mean well, but that’s a very difficult comment to receive when you’re in the midst of something genuinely upsetting.”
* A pained non-smile and raised eyebrows, paired with no verbal response.

If Jane genuinely does mean well and just has never thought through how her attempts at forced cheer are coming across, responses like these might jog her into reassessing the habit. But it’s also possible that some of these responses could alienate her and cause her to become snotty to you or to think of you as a problem (which is not great if she’s senior to you), so you’d want to factor that into your thinking about which might or might not work for your context.

my job changed … and now I hate it

A reader writes:

Three years ago I had a job that paid well, but was tedious and unfulfilling. I left that job for a similar but much more creative position at a significant pay cut. It was worth it because I loved my new job… until recently.

For the last 4+ months, I’ve been doing the same work I was doing at my previous tedious job. It’s expected that everyone on the team eventually has to work on a boring project for awhile. But this time the drudgery is showing no sign of letting up, it’s my only project (unusual), and it often requires me to work late nights. I am miserable and feel am I past due to be put back on the kind of projects I was hired to do.

This week I found out that this project will be going on for the next three months at least, and then will continue indefinitely, and they don’t have any plans to take me off it. I feel like they’ve pulled a bait-and-switch on me, knowing my past experience, and that I’m being used to keep their cash-cow client so the rest of the team can pursue more creatively fulfilling projects.

What’s the best way to approach my manager about this? I’m not willing to continue doing this project, especially not at my current salary, although I would be willing to split my time between this project and others for a modest pay raise. I’d also be willing to stay at my current salary if I knew I’d be taken off the project permanently after the next three-month cycle. However, I don’t think anyone else on my team is skilled enough in this kind of work to keep up with the project’s demanding timelines.

I answer this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

educating my ignorant but well-intentioned collaborator is exhausting me

It’s the Thursday “ask the readers” question. A reader writes:

I have a long-term mentor-esque figure who I used to work for and have benefited from in terms of professional connections. Earlier this year, he approached me about collaborating on a project that was right up my alley. I had some hesitation because of our differences: me, a queer woman in her late twenties; him, a straight man in his forties, which I worried would make for a weird power dynamic, not to mention a potential disparity in fluency on topics like gender, sexuality, etc., which were tangentially related to the project.

But I have always had positive experiences with him and he hasn’t been my boss for years. He also encouraged me to challenge him if I had concerns — my comfort with these topics was part of why he asked me to collaborate, since he wanted to make his project more inclusive and knew he wasn’t the best person to do so. As a bonus, because he’s seasoned in his field, there was a high chance it would actually come to fruition and be profitable. So I said yes.

Well, it’s since become clear that his familiarity with engaging topics around women, queer people, and trans people is a lot more elementary than I anticipated. As a result, I’m spending a lot time engaging with and editing the parts of his work that are inadvertently sexist, queerphobic, and transphobic. He acknowledges my notes and I can fix them as I please, but they’re not really sinking in in any permanent way and I don’t think I have the bandwidth to continue playing the role of educator on top of my half of the project longterm.

How do I back out of the project respectfully? We have a positive history and his intentions are good — kind of like when your grandpa never learned that you shouldn’t use “transexual” anymore or thinks non-straight sexualities are exotic and defining personality traits. It doesn’t make it okay, but it’s a matter of ignorance versus outright maliciousness. But I’m not really eager to say, “You aren’t educated enough on basic feminist vocabulary or LGBTQ people, and I didn’t sign up for so much emotional labor. But don’t worry, I don’t hold it against you because it’s clearly a generational thing!” So, I’m at a loss.

Is there a way to step down in a way that doesn’t burn this bridge or put me in the position of having to explain in detail the ways I think he’s insensitive and uneducated?

Readers, what’s your advice?

my interviewers didn’t hang up the phone after my interview, my boss can’t move past a mistake I made, and more

It’s five answers to five questions. Here we go…

1. My interviewers didn’t hang up the phone after my interview

I had an interview today that I thought went well — right until the end. I was prepared for all questions, had a few on my own to ask (thank you for the great interview advice by the way – I wasn’t at all caught off guard by anything thanks to your tips!), I projected myself as confident and able to handle the job. Brilliant!

The interview itself was over Skype, and for some reason when they disconnected the program, only the video shut down. I sat there in absolute silence listening as they discussed the previous 20-minute meeting. I didn’t know what to do! If I tried to disconnect, they would know for sure I was still able to hear them, so I froze.

I don’t think I did as well in the interview as I thought. What I took as confidence they called “control issues” and the main takeaway was they thought they might have problems keeping me low-key enough for the position. I’ve never been told I was controlling before, so I’m not sure how to take that, but my initial thoughts are I certainly have not landed this position.

My question is, what should I have done? Should I have interrupted them as soon as I realized I could hear them all talking and they were unaware I was still on the line? Do I email them back and tell them that I actually overheard their discussion and let them know I’m not really a control freak, I was trying to project confidence and obviously failed at that?

Oh no!

Yeah, ideally you would have either disconnected as soon as you realized you were hearing what was supposed to be a private conversation or spoken up right away so they knew you could still hear them, although I can certainly understand how you ended up sitting there frozen.

I would not email them and explain you heard the discussion; it’s going to raise the question of why you stayed on and listened. And to be clear, a lot of people would have found it hard to resist the temptation too — but the fact that you didn’t is not likely to go over well with the people you listened to.

Instead, I’d just take this as a behind-the-scenes glimpse that you normally don’t get to have. Unfortunately, that glimpse may or may not be useful, though. Maybe you really did come across as overly controlling … or maybe these people react that way to appropriate amounts of confidence (which might indicate that they penalize employees who dare to be confident or assertive too, in which case, it’s better that they screen you out). It is worth reflecting on whether there might have been something in your manner that a reasonable person could have misinterpreted, and maybe seek feedback from someone whose judgment you trust and who you know will be candid with you. But otherwise, sometimes hiring managers just get it wrong, especially when all they have to go on is a 20-minute Skype conversation.

2. My manager can’t move past a mistake I made

What do I do when my manager won’t forgive me for a mistake? It’s part of my job to send out correspondence and various paperwork to clients every month. A few months ago, I made a careless mistake that caused me to send some paperwork to the wrong client. This was a problem because the client saw sensitive information that they should not have seen. My manager told me about it, and I was mortified at my mistake. We were lucky in that the client was not upset and worked with us to resolve the issue, but it could have gone much worse.

Ever since then, I have been extra careful and have made sure to pay better attention to what I’m doing, and I have not made the same mistake again. The problem is that my manager still comments on and brings up my mistake, even months later. When I do the monthly paperwork, she will always remind me, multiple times, to double check and not mess anything up.

It’s not that I don’t take responsibility for my mistake, because I do, which is why I’ve been, and will continue to be, very careful not to repeat it. But I can’t help but feel like my manager doesn’t forgive me and that she’s holding this over my head. Maybe I deserve this for making such a mistake, but I’m not sure. How do I go about addressing this, if at all? Should I not say anything and just hope she eventually forgives me?

If this was a very serious mistake, it’s understandable that she’s worried about making sure that it won’t happen again — and she’s not in your head, so she doesn’t necessarily know what you’re doing to ensure that it doesn’t. But the way she’s going about this isn’t particularly useful. Just reminding you not to mess things up isn’t going to be especially effective.

What she should be doing is talking through what you’ll do differently to make sure it doesn’t happen again. Since she’s not doing that on her own, though, you can do it! Try saying something like this to her: “I want to let you know what steps I’ve taken to ensure that doesn’t happen again. I think before I was sometimes letting my mind drift when I put the client packets together, and I realize now I can’t do that. So I’m staying very focused when assembling these materials, and I have a checklist for each client that I check off as I put their packets together. I’m also double- and sometimes triple-checking everything before it goes in the envelope. I know how seriously I need to take this, and this new system is working really well.” (Or whatever your system is. If your system is now just “I pay more attention,” that itself may not be enough to set her mind at ease, so if you come up with concrete steps, it should help.)

That said, she still may remind you to double check. I wouldn’t see that as her holding it over your head, and instead just see it as her natural concern that a client relationship was potentially jeopardized. It should go away in time, but if it’s still happening a few months from now, you could say, “I get the sense that you’re still very worried about the care I’m taking with these materials. Is there anything you’d like me to do differently so that you can be confident I’m on top of it?”

3. Interviewer wants me to do a 30-hour, $2,800 project for free

I freelance on the side and am currently looking for a new full-time job. I got a second interview for an eLearning Developer position. Before the interview, they asked me to do a “sample task”. I’ve been asked to do pre-interview tasks and assessments before and they usually only take an hour or 2 at most. I got the “sample task” for this interview and it was essentially: create an entire 30-minute learning module with video, graphics, at least 2 interactions, voice over, and an online discussion community. If this was for a freelance client, I could bill this “sample task” at $2,800 (and would take over 30 hours of my time). This seems outrageous to me.

I offered up my portfolio as an alternative (I already include all the components they are asking for) and they still want me to do this sample project. It seems like they are trying to get free work, but some family and friends I’ve talked to say I should just bite the bullet and do it because it’s “normal”. What are your thoughts?

Nope, not normal. Asking you to do a smaller piece of work so they can see you in action — yes, good and normal and useful. But that should be an hour, two hours tops, and it should be clear that they’re not asking you to do anything they actually might use.

I’d say this: “I’d normally bill close to $3,000 for this work and it would take 30+ hours of my time. I absolutely want to get you what you need to be able to assess my work though. Would it work for me to do a piece of this rather than the whole, such as (suggest specific piece here, one that would be more reasonable)? Alternately I’d be glad to show you projects I’ve done that include all of these components.”

But if they insist, you’ll have to decide if you’re willing to walk away from the job over it. If you have other good options, you should.

4. I’m leaving in two weeks and my employer has no plan to replace me and is piling work on me

I work at a small nonprofit as the only person in my department due to the departure and non-replacement of the other people who were once part of it, with my responsibilities requiring vastly different training than the rest of the employees on staff. This includes any and all money-related duties, especially donations that flood in at the end of the calendar year.

I gave a month’s notice to make sure everything was taken care of to best set up my position for my successor but have been informed that the organization has no plans to replace me, requiring me to write an extremely in-depth succession plan and do a considerable amount of set-up for the next five years for the parts of my job that would have required overlap training to hammer out. My boss has put even more work on my overflowing plate, including projects that will be starting after my departure because she “doesn’t know who else to give them to” and has given unrealistic expectations of my capacity to work on these projects to the people we have hired externally to help. Am I being unrealistic in thinking that there should be an exit plan on her part?

Nope. But that’s their problem, not yours, and you shouldn’t move the burden over to yourself. You don’t have to work extra hours or take on extra stress to do everything that they’re piling on you. It’s fine to tell your boss, “I won’t have time to do all of this before I leave. What would you like me to prioritize?” If she tells you “all of it,” then say, “I want to make sure I’m flagging for you that I’m not likely to get to all of it, so that you’re not planning around it all being able to be completed in the amount of time I have left. I’ll start with A, B, and C, and then if I have time once that’s done, I’ll spend any remaining time on the rest. But let me know if you want me to prioritize things differently.” And then stick to that.

By the way, even in organizations that do replace people, it’s pretty normal not to have the replacement start before the outgoing person leaves. The point of a notice period (even one-month notice periods) isn’t to do training overlap, since hiring someone and waiting for them to start often takes longer than that. The point is just to get your projects in decent shape and leave behind some decent documentation for the next person (but without requiring the exiting person to work longer hours than usual). So don’t stress over that piece of this.

5. When can I check back with this company about their hiring decision?

I have been talking with a company for a couple of weeks now about potentially being hired. They said that they should know for sure about what is going to happen early this week. Monday was a bank holiday for them, and I haven’t heard anything yet. I was wondering when it would be prudent to follow up with the company? If I email them today, is it too soon?

Friday at the earliest. Hiring often takes far longer than people think it will, even the people setting the timelines. Always add at least a few days to whatever day they tell you to expect to hear back before you even start thinking you might hear something soon (and even that won’t always be enough; sometimes you have to add a week or two or more).

I lied to my boss and said I’ve been doing a task I haven’t actually done

A reader writes:

I started at my company in an administrative role and was quickly promoted to a highly technical role, which came as a challenge. My technical experience being quite limited, I met with some freelance consultants to go over the nuts and bolts of the role. I was scrambling to understand a lot of information very quickly, and when my boss asked me early in the training process if I had been trained on one specific task yet, I confused knowing what the task meant with actually knowing how to do it, and I said yes.

I know I should have cleared it up once I realized later that day that it wasn’t true. But I was learning so much so fast and had to get through everything with the freelancers in the time allotted. I figured the freelancers would cover this eventually. But they didn’t, and I forgot about this, and then training ended. Weeks passed, and then out of the blue my boss asked me how this task has been going. I panicked. I didn’t lie but I didn’t tell him I haven’t been doing it.

It’s a recurring task that only needs to be done every once in a while, and it’s just about checking up on one element of our technical set-up, so I said something like “Good thinking, I should take a look at how things are going with that.” So … sort of implying I had done it before. Which isn’t honest, I know!

Right after that, I tried finding guides and tutorials online and in local organizations for professionals in this industry. But I can’t find anything. I know that I have to say something now, but I’m terrified.

How can I fix this? Can I fix it? If you were my boss, would you ever be able to move past this if I came clean and took the steps to learn it now? I’m in a panic and I just want to make it right.

You can fix this.

Go back to your boss and say this: “I realized I misunderstood what you were asking me earlier when you asked how the X work was going. I went back and took a look at my notes and realized the the consultants didn’t actually cover that with me, and I want to get trained on it as soon as possible. Do you think I could get a little more time with them for that, or is there someone else who can go over it with me?”

The good news here is that you didn’t say “Yes, I’ve been doing it.” You said, “I should take a look at how things are going with it.” It’s easier to turn that into “Whoops, I took that look and realized I need training.”

And yes, it’s true that when he asked earlier if you’d been trained on it, you said yes. That’s not ideal, but you wouldn’t be the first person to have just lost track of what you had and hadn’t covered so far during an intense training period. (And in your case, it sounds like it was just genuine confusion, not a deliberate lie.)

The most important thing here is to talk to him about it as soon as possible. Talk to him today. Because the longer he thinks this is being covered when it’s not, the more potential there is for real problems to result (or just for him to be much more concerned when he finally does learn about it).

But also — figure out why, when he asked you about it the second time, you panicked and didn’t tell him the truth. That’s not a helpful instinct to have, and it can really come back to bite you if it happens again. One time you can fix, but multiple times will worry your boss and potentially cause real problems for you and your work. And plus, it was unnecessary! It would have been fine to just say, “Oh no, I just realized that we didn’t finish covering that — I’ll need to call them and find out what I need to do.” That kind of thing happens, and it’s much, much better to be transparent when it does. So it’s important to figure out what led you to respond the way you did, dismantle whatever assumptions were in play that caused it (for example, that you’ll look incompetent if your boss sees that you’re not perfect), and shift your mindset to one where you truly believe that you’ll come across better — and do your job better — if you’re honest and transparent, even when you’ve made a mistake.