Reader Question #2: Asking for vacation time from the boss who won’t plan ahead.

A reader (!) writes:

Dear Captain Awkward:

My boss dislikes planning ahead, and likes to keep her options open; my coworkers and I need to plan our vacation days long in advance because of our other jobs & commitments.  Do you have advice for handling the boss?

Yes.  Yes I do.

Assuming your boss knows about these other commitments and isn’t just passive-aggressively trying to remind you that she wants to be your priority, your boss sounds like she fit into a category that I’ll call The Disorganized Micromanager.  She is too disorganized to know what she’ll be doing when you need that vacation day three weeks from now, but she’s afraid to let go in case she does need you and so is behaving like a control freak.  Is she otherwise bad at delegating?

In my experience, having employees helps a person get organized in three important ways.  1) They do that big pile of stuff that you can’t/don’t want to do,  2) You have to get organized enough yourself to break off discrete chunks of work and delegate them, and 3) If you’re really disorganized your assistant will know and you will feel their disdain at your incompetence. Managers should theoretically be good at this stuff, but the fact is sometimes they aren’t, and I’ve certainly found myself in situations where there is a bright shining face looking up at me saying “Give me stuff to do!” and it takes a lot of mental energy to climb out of my own giant pile of work, look at the bigger picture, and let something go.

So:  Managers should be really good at handling this stuff, but sometimes they aren’t, and they make everyone around them nuts. You will be better at handling your boss if you accept that sometimes you need to manage her.  A good way to manage a relationship with someone who likes to keep everything open-ended but who also can’t let go is to ask yourself, “What are this person’s fears and anxieties?”

• Fear that the day will come around and something that’s not on the schedule now will be on the schedule and she’ll be understaffed?
• Fear that your outside commitments are more important than your job with her?  Trying to find a way to exercise control and remind you that she’s boss?
• Fear that you guys might find out that she is afraid to schedule time because you’ll find out that she’s disorganized and can’t plan ahead?
• Does she have extensive outside commitments herself and is afraid that if you guys take too many days off it will impair her own flexibility in her life outside of work?
• Have there been major problems or issues that came up when you or your coworkers were out on vacation that your boss had to handle or that affected the operations of the business?

The thing about anxiety is that it doesn’t have to be rational or based in truth in order to have power over us. But if you can put yourself in her (possibly crazy) shoes and try to figure out “What is she afraid will happen if she agrees to this vacation schedule now?” you’ll be in a better position to craft something that anticipates and meets her needs.

Okay, now for some more specific stuff you can do:

1. Does your organization keep a communal calendar where everyone can see it?  Is the schedule of what you do regular and predictable?  Do you have big monthly or annual events that require all hands on deck?  If not, maybe your first step is to create one and place everything that you know about onto it.  Congratulations!  You now keep the company calendar!  You just took a huge planning weight off your boss’s shoulders, and you now control the flow of information about what’s coming up.  Once you guys figure out which days you’ll be off, you can also enter that into the schedule (I suggest color-coding) so that your boss can plan around it.
2. If one of your boss’s anxieties is “But I’ll be understaffed!” make sure you coordinate with your coworker to make sure that your time-off requests don’t overlap.
3. Think about how  you present the request.  Maybe for your boss, “These are all the days I’ll need off for the next 6 months!” is too much information.  Maybe it feels like too many days off.  Maybe presenting it as the “Vacation Schedule” is ticking her off in some way, like “God, why are they so obsessed with vacation?  They should be giving me their Schedule of Working Hard!”   Is your boss an email person or a in-person person?  By which I mean, I have certain coworkers who want to be emailed information or requests so that they have everything in writing and can process on their own schedule, but I also work with people where it’s far better to make requests in a conversation and then follow up with email.  Because they never check their email, or because of weird tone issues, or they just want the big picture first and will worry about the details second and if you start with the details they get bogged down in them.  You have to know your audience.
4. Have you asked her how she’d like to handle vacation requests?  “Hey Boss, Coworker and I have been looking at the schedule, and we’d like to nail things down with you to make sure that you’re fully staffed and covered, especially for ______ (upcoming event or priority).  Do you want us to email you or should we schedule a meeting to talk about _____ (vacation, upcoming priorities)?  We need to hash everything out by ____ date.” If this is a sticky wicket every month, and you all know that it is, what would you lose by saying “Boss, it’s time for us to nail down the schedule again.  I know that last month it was difficult for us to work something out in a timely manner.  How do you want to handle that from now on?”

I’ll probably end up devoting a whole post to this, but in a situation where there is conflict one of the best things you can do is stop assuming how other people will react and just ask them for their best-case scenario. It gets people to stop dwelling on things that won’t work and it forces them to articulate a vision.  “In a perfect world, where you get everything you want, how would this unfold?”

I saved this one for last, because I think the above suggestions are probably the most constructive and friendly, but one way to get someone who has a hard time making decisions is to a) frame the question as a choice between two options and b) present it less like a request and more as an FYI.  And this is definitely a strategy that lends itself to email.

“Dear Boss,

Given (upcoming event that your boss really cares about) and (upcoming priority that your boss really cares about), Coworker and I would like to let you know about our work schedules now so that you can plan.

You:  (Dates)

Coworker:  (Dates)

The last week of the month I could take off either the Wednesday (date) or Thursday (date).  Do you have a preference?

Best,

You.”

You’re telling, not asking.  You’re entitled to x days off and you’re letting her know what they are, but in a way that shows you are sensitive to her priorities.  You’re giving her a defined area to express preference and control and framing it as an either/or choice – not “Can I have a day off during that week?” but “It can be Wednesday or Thursday. Pick one.”  And you’re putting it on her to raise concerns if she has any.  Otherwise you can assume that’s the schedule.  And you’re not being high-handed.  You’re doing her a favor by presenting the information to her in a way that she can quickly process it and not get bogged down in all the possibilities, which is maybe what she needs even if she doesn’t know it.

Now a true master of passive aggression can still keep dithering, so some gentle follow-up may be required.  But I would not do this too far in advance and I would do it in a specific, not blanket way.  Don’t write and say “Okay, since I didn’t hear anything from you I’m assuming that all those dates for the next six months are okay!” You’ve come so far, why would you panic her now?  I mean, go about your life, plan your other commitments, assume that those will be the days off, and then a week or so before send her an email about something else you need to talk about, and then include something at the end, like “Just to remind you, I’ll be out of the office next Tuesday, but Coworker will handle this if any calls come in while I’m out.” If you get friction, pull out the initial email where you sent all the dates, and say “I’m really sorry if this inconveniences you, but based on our discussion of (whenever that email went through) I went ahead and scheduled (outside commitment).” And then put it back on her.  “How would you like me to handle that next time?”

Okay, one final final final thing – just a basic etiquette thing from someone who has had many jobs at the same time where some of them are dream jobs and some of them are just paying the bills, and also the experience of asking time off from work so that I can…do other work:

Love the one you’re with. By which I mean:  Limit how much you talk about your outside jobs and commitments when you’re at your present job.

My worst temp job ever involved 1) shredding documents 2) in a closet 3) for 27 business days 4) working under a mincing control freak who would occasionally sneak up outside the door and then abruptly open it so that he could remind me that “Team Players don’t wear headphones at work!” and then report me to the temp agency.  For listening to music.  In a closet.  While I shredded documents.  While I’m pretty sure Team Players also get health, dental, more than $9/hour, and a work environment that is 1) not a closet and 2) free of constant emotional abuse from a tiny mean man with a soul patch, and while it may have helped my fragile self-esteem to remind myself that I’m “really” an artist, my coworkers did not want to hear about it.

Your boss doesn’t necessarily need to know why you need the time off or the reminder that you’ve got better things to do.  If you are entitled to the time, just request the time and keep the request focused on her business and her priorities.