3 Convos You'll Have to Start With Your Boss (Because She's Not a Mind Reader)

Your boss isn’t a mind reader. He doesn’t know what you’re thinking, doesn’t, for example, know that you’ve modeled many of your workday habits about him.

And because he doesn’t know what’s going on in your head—beyond what you explicitly reveal—he can’t possibly make any changes or suggestions that would benefit you. And that means you just end up adopting all his habits and routines because you think that’s the way he wants it.

But what if that wasn’t the case? What if he said the following to you:

1. “You Don’t Need to Mimic My Hours”

Your prime work hours are 8 AM to 5 PM. After 5, or let’s be real, 4:30, the only reason you’re still sitting at your desk is because of a little something called face-time. Your boss typically rolls in the office a little before 9 and never leaves before 6.

Even though your supervisor hasn’t told you that you must be in the office during the exact hours that he is, he also hasn’t told you otherwise. And wouldn’t it be great if he made it abundantly clear that your hours are your hours, and when he comes in and leaves shouldn’t have any impact on when you do (provided that you work at an organization that doesn’t require strict hours so long as you’re completing your projects.

How to Ask

You can straight-up ask your manager if he needs you to be in the office when he is. Say this, “I can’t seem to sleep past 6 AM these days, and I’ve really learned to embrace starting my workday at 8, but more often than not, my productivity drops off by around 5 PM. Is it OK with you if start coming in earlier and leaving earlier?”

If he looks flustered or confused, he probably didn’t even realize what you’ve been doing, sticking around long after you’re done for the day just because he’s still there, and he’ll give you the out you’ve been eagerly awaiting.

If he actually does want you there when he is, he’ll let you know that, too.

2. “It’s OK to Work From Home”

Monday morning, your plane’s just landed after a weekend away, and the first thing you do is check your email and message your boss. “I just got in, but it looks like I am going to be a little late because of traffic.”

You’re exhausted from the red-eye, could use a shower and maybe a short nap before you zero in on the day’s agenda, and you’d rather not drag your suitcase to the office. Honestly, there’s no reason why you shouldn’t just be able to put in a full day’s work from your couch. Thus, you’d love nothing more than for your manager to reply to your message like this, “Why don’t you work from home today. I’m sure you’re tired from the trip, and I can’t see why you must physically be in the office today.”

How to Ask

What if you took a different approach to that “I just landed” email? Try this, instead: “Well, I’m back and was planning on heading straight in, but, honestly, I feel a little grungy and think I’d probably have a more productive day working from home today, if that’s something you’d be comfortable with. I’m going to prioritize [name of item] and will follow-up with [name of other item]. Please let me know if that works for you.”

If she says OK, great. Go home and get set up in front of your computer. And if she doesn’t, suck it up and head into the office as planned. Instead of using energy getting angry, plot the conversation you’ll have at a later point about working remotely on occasion.

3. “Why Don’t You Leave Early Today?”

As much as you try not to let your personal problems get in the way of your work, sometimes it just can’t be helped. You’re doing your best to focus, but it feels utterly pointless. Staring at the computer, you’re basically pretending to look busy and productive while your mind’s consumed by something that feels more important than the weekly spreadsheet.

You’re pretty sure you’re not fooling anyone though, least of all your manager, who’s seen you get up to take more than one distracting call in the past hour alone. Sensing that something’s not quite right with you, wouldn’t it be great if he turned to you and told you that it was no problem if you wanted to call it a day? That you can pick up tomorrow?

How to Ask

Since your boss probably already has an inkling that today isn’t your day, stop pretending like things are fine and send this email:

“Hi, To be completely candid I’m not as focused as I typically am due to personal matters. Do you mind if I head out on the early side today so I can come back fully refreshed tomorrow?”

Keep it short and simple, making sure to add how it benefits your boss, too (you’ll be more productive if he says yes).

Taking initiative when it comes to things like this is a little scary. You don’t know how your boss is going to react, and uncertainty can be frightening. Fortunately, if you can find the right words and a relaxed approach (with an internal promise to yourself to handle whatever response you get with equanimity), you might just get what you were looking for sooner rather than later.

Photo of person courtesy of Thomas Barwick/Getty Images.

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