A reader writes:
I need your advice on a situation that I found myself in this week at work. I work for a small business. There are around 20 employees in my office with no HR department. I started as an intern in the fall and was hired early this year. As part of my new job, I am responsible for scheduling one of the partners. This responsibility includes booking his flights and hotels when he travels, which is quite often. Before I took on this responsibility, my boss’ wife was booking his flights for him. When I first started booking his flights, she reached out to me and asked me to call her so she could give me her tips and tricks on getting the best deals, which I did.
My boss is on the road now and before he departed, his wife asked him to put me on the phone with her so that she could give me more advice. I have been following her “advice”: always book airline tickets over the phone, try to see if you can use airline miles that are expiring soon, etc. My boss’ plans changed yesterday and I preceded to change his flights and hotels accordingly. The flight change turned out to be very, very expensive, despite booking a flexible ticket originally. My first priority though is to make sure that my boss gets to his meetings on time, on an airline that he prefers, rather than searching for a long time to get the best deal on another airline. I spent 45 minutes on the phone with his favorite airline trying to get a better deal, but in the end I had to book the expensive ticket and used miles that are expiring next year to pay for a part of it. I did look online at the other airlines my boss likes to fly and their ticket options were even more expensive.
After I booked the ticket, I emailed my boss his new itinerary and cc’ed his wife, which is the protocol that my boss established. She responded to the email and questioned why the flight was so expensive and reiterated that I should call her if I ever need advice on booking tickets.
As I am responsible for scheduling my boss, all of his emails come to my computer as well, so that I can make sure all of his appointments get on his calendar. I don’t snoop through his emails but I do get a notification and a very large preview of every email when it comes into his inbox. After she questioned the price of the ticket, my boss’ wife also emailed him directly to express her “annoyance” with me and how I handled the flight change. She also complained that I did not get the best deal, did not consult her before using airline miles and refuse to call her for advice.
I am not sure what I should do. This is my first job, but I am fairly certain that assistants don’t typically deal with their boss’ spouses and have to call them for advice on booking flights. I know that my priority needs to be getting my boss where he needs to go, when he needs to get there, on an airline he prefers. I don’t know where appeasing my boss’ wife fits in here. Should I try to appease my boss’ wife when booking his flights and let her comments go?
Yes, this is weird. And a bad idea. If this continues, you’ll be essentially reporting to a second boss, one who doesn’t even work for your company and who won’t be privy to other considerations and priorities that you’ll be juggling.
Of course, just because something is a terrible idea doesn’t mean that you can change it, but start by talking to your boss.
Say that you were glad to get his wife’s advice and tips on booking flights, but you’re unclear on whether she will be having a continuing role in managing his travel. Explain that you had assumed that once you were trained, you would be managing the travel, but you’re getting the sense that she’s continuing to oversee it, and say that you’d like clarity on your role and her role, if any. Frankly, you can also mention that you couldn’t help but see her email expressing annoyance that you didn’t consult with her, since his emails all go to you.
Listen to what he says. If he tells you that you’re now managing this and that she should be wrapping up her role in it, then I would say, very nicely, “Does she know that? I want to make sure we’re all on the same page.” (Again, be very nice — bending-over-backwards nice. Making an enemy of your boss’s wife is generally not a great idea.)
On the other hand, if he tells you that she’s going to stay involved in any capacity, then you need to decide how much this bothers you. Is it something you want to push back against, or do you want to suck it up and deal with it?
If you decide to push back, be aware that you might not win, so you want to go about it extremely respectfully. I’d say something like, “I’m concerned about reporting to two different people, and it sounds like I’d be reporting to her on travel and that she’d be assessing how I do. I’m not entirely comfortable with that, particularly since she won’t always be privy to all the considerations and priorities that need to be juggled, and I wonder if there are other arrangements we can make.” But if that doesn’t work — well, then this is the job and you’ll need to decide if it’s one you want or not.
But yes, this is weird.