Last week, my boss missed a scheduled call. I sent him an email after 10 minutes of waiting, then texted him after 30 minutes, but got no response. I called and left a voicemail saying we could do it another day. He called me back an hour and five minutes late and, without even acknowledging or apologizing that he’d missed our time, proceeded to dive into the agenda.

I have two questions. First: Is there a standard for how and when to follow up with someone who is late — especially someone in a position of power who has information you need? Second: Why don’t people apologize for being late or missing appointments? Should I have called him out on it?

Emma: I did a quick Google to see if there was any Official Protocol for this type of thing. In 2016 The Chicago Tribune quoted a business etiquette expert(!) that “after 30 minutes you’re good to go,” so I think your instincts were spot on. The 7–12 minute mark is also when I send my first inquiry into the void. If I don’t hear back by 20–30, I consider it a bust and usually send an email with new times I’m available to regroup. Granted, this isn’t much help if you really need them to show up for you. It’s frustrating to wait, it’s even worse if they don’t acknowledge it, and you can absolutely call your boss out on it. I will admit I do not have a long history of this kind of confrontation. I’m getting better at it.

Andy: Yes, this is a question of power — the boss doesn’t have the same consequences that their reports do. In the past, I would have said it’s risky to call them out. Today, I say: Take the risk. You have all the usual channels. What email would you send to your report about a missed meeting? You can send that same note to your boss:

Hi Boss,

When are you next available to meet?

Since we didn’t have our meeting today, we are at risk of missing Tuesday’s submission deadline, and would have to pay $500 in late fees. I’m blocked on XYZ Project until we meet.

This is my top priority. I can move anything on my calendar.


Or, you can just ask for what you need over email:

Hi Boss,

Here’s the information I need for next Tuesday’s submission — please respond by EOD Friday. If you want to go over it in person, let’s reschedule our meeting. My calendar is updated.

[Bulleted list of information]


Emma: You get to choose your own spice level on this. I’m most comfortable around two stars and therefore tend to couch my confrontation in (sometimes feigned) curiosity: “So glad I could get ahold of you. How are things going? Did something unexpected come up?” I like that this gives me intel on what else is going on — more context! — as well as very naturally opens the door for them to own their lateness.

Andy: I also support a full five-star spice level: “Hey boss, our meeting was supposed to start at 3p. What’s up?” Fair warning: Your most important meeting may not be your boss’ most important meeting.

Emma: If in-the-moment isn’t your style, 1-on-1s are a great time to clarify expectations: “Hey, I’m curious what you’d like me to do if you’re running very late for a meeting, like last week.” Remember, it’s your job to do your job and that sometimes means getting them to do theirs.

My company just went through a pretty dramatic round of COVID-related layoffs. My job is safe! But when I found out I wasn’t being laid off, I felt more disappointed than relieved. Any advice? 

Emma: It’s time to start looking for a new job! This is a huge and intimidating undertaking that I suspect you’ve been putting off for some time. Feeling disappointed means you were waiting for your circumstances to make a decision for you. I’d argue they still have. You have fully confirmed you don’t want this job.

Andy: You can’t un-know the truth in your heart. I recommend some journaling about what your hopes were for your post-layoff life: What were you going to do with the time? What was your next career move? Ask yourself how you can still do those things. What steps do you need to take to get where you want to go? How can you create your own severance package that’ll launch you forward? You’ve got this.

Last year, I was contracting with a company I really like. I was mostly working with Team A, but spent a couple of weeks helping out Team B when Team A was slow. Team B wasn’t great — their processes were pretty chaotic and the person who would be my manager isn’t someone I would thrive under (poor feedback, virtually zero coaching). That said, the stuff Team B works on is cool, and doing it with them would be great for my career. Should I go for it?

Andy: Absolutely go for it! Applying for a job doesn’t mean you’ll get an offer. Applying doesn’t mean you have to accept an offer. And accepting a job doesn’t mean you have to keep it. You’re not locked in. Of course, there’s the question: Can you afford to be choosy?

Emma: I am all for applying to every job that is cool and at a company you like and would be great for your career. The real decision will be whether or not to accept an offer should you get one. I really don’t like having a bad boss, and knowing I was walking into one would also give me pause. Then again, “getting your foot in the door” at a great company is a perfectly reasonable career strategy. Then again, you don’t know if quickly quitting a team to try and join another will taint a future application. Then again…

Andy: Any job is kind of a crap shoot. Personally, if I wanted to hire someone and they had worked on (and then left) what I knew to be a chaotic dysfunctional team, I’d be more interested in hiring them to my team, not less!

Emma: Same. Let us know how it goes!

I got this email from one of my new direct reports this morning. How would you respond? I don’t want to fuck this up.


I wanted to let you know I just found out I’m pregnant. It’s typical to wait 12 weeks to notify you, but I thought it was important to share since I’m starting to feel a little unwell. I’ll work through as much as possible so as to not affect work, but wanted to make you aware of my current situation.

Emma: My hunch is that this is your first pregnant report. You know it’s a fraught topic; you’re aware that most parental policies, particularly in the US, are not great; you know you will have to make accommodations and change things on your team; and you’re feeling a little shaky on “the rules.” I appreciate that you don’t want to fuck it up. The fact that you felt that zing of anxiety over a fairly straightforward email shows that you care.

Andy: Yes, exactly. And that straightforward email should have three parts: Your first move is congratulations! Then, a confirmation that you’re here to support her, and finally, a request to book a meeting to talk about the details. Here’s what I might write back:

Congratulations on this news! I’m so sorry to hear you’re feeling unwell. Let’s book a meeting to talk about the details. When you’re ready, I’d also love to set up a meeting with Tara, our HR business partner, who can share more about our company’s parental policies and ensure you’re getting any support you need.

Emma: Your report gave you the gift of time by announcing her pregnancy early. Between now and that first meeting, read up. Don’t reveal this person’s news, but talk to other managers and people in HR. You don’t have to go it alone — looping in HR is key — but I want you to feel confident. These resources can be a helpful starting point, then keep going.

Good Boss Achievement Stickers: Grab Bag Edition

A digital sticker sheet with five stickers [1] a red chili pepper labeled Spicy captioned "gave five-star feedback" [2] a ouija board pointed labeled "all signs point to I don't want this job" surrounded by a crystal ball and crystals [3] a persons hands "making resumes rain" captioned "never don't apply" [4] a woman looking at a disassembled table captioned "didn't know" next to a happy lady next to a built table labeled "Found out"