Welcome to our new Friday Column to give you workplace advice and coaching, “Dear Dana”! Every Friday I’ll be answering your letters outlining the challenges you have dealing with difficult bosses, challenging colleagues and other tough situations at work. Please write in and tell me about a frustration you’re facing at the office. I’ll publish a response every Friday and we’ll also be discussing these topics on our Tuesday Coffee Break talkshows with our guests! I can’t wait to hear from you! – Dana Theus
Dear Dana, My boss is driving our team crazy with the emails she sends us in the middle of the night. It’s not uncommon for her to ask for a response by 8am. Keep in mind, our official office hours are 9-6pm. She also emails my team directly and they come to me panicked in the morning because it’s 9:15am they are just getting to email and feel guilty because they didn’t see her 2am request. My team is coming to me for solutions and I’m not sure what to do. I have the same questions: Should I talk to her and ask her to stop? Should I ask my team to forward her emails to me and check-in frequently during the all night? I hardly get enough sleep as it is. Help! – Panicked in Seattle
I feel your pain! I had a boss like that who was hired under orders from the CEO to “clean up the marketing department” right after our internet startup’s IPO. She came from a company which was notorious for round-the-clock work, and she honestly believed her 2am emails with requests for 7am answers were some kind of kick-ass work ethic. Sadly, her style conflicted mightily with my preschool-kid schedule and 45-minute commute. It’s an understatement to say it sucked.
From reading your letter, it sounds to me like you have two problems.
First, work-life balance boundaries.
Here’s what’s probably going on. Your boss is under pressure, is sacrificing her own work-life balance and is probably worried about getting a call on the way in to the office from her boss asking for an update. If she is stressed, you don’t want to trigger her into even more stress (which she may take out on you or your team unwittingly, or wittingly if she is bully-behavior-prone). And don’t trigger yourself and feel anxiety with thoughts like, “I’ll get fired if I don’t respond to every midnight missive by 4am.”
Like I always say, detrigger yourself early and often because it’s unlikely you’ll get fired over this and when you’re detriggered you’ll find it easier to let go of the 3 A’s (anger/annoyance/anxiety) so you can see your options more clearly. For all you know, your boss is just trying to see how far they can go before you establish a boundary. (Not terribly proud to admit I’ve done this before myself…ahem.) But even if your boss is just testing your boundaries, she is still likely to get nervous and put you in the “not my best team member” category if she doesn’t feel like you’ve got her back. So your challenge is to make sure you work out an “I’ve got your back” agreement with your boss that supports the boundaries and work-life blend you and your team need.
What will it take for her to feel l like you’ve got her back?
Unfortunately, I don’t have any insight into this – there are too many factors. You simply won’t know until you ask her. The best way to approach her is to go into a meeting with a proposal that you believe is responsive to her needs and respectful of you and your team’s work-life needs. Start by talking to your team to understand what their work-life needs are. Maybe some people are willing to be responsive in the off-hours if they get flexibility options during work hours. Maybe this is a trade-off you can make, personally. Use this info to help you develop your proposal. Start your conversation with your boss by saying you know it’s important for your team to be responsive to the business even when the business isn’t 9-5 but the team is struggling to figure out what is urgent and what can wait ‘til regular business hours.
Make your proposal and be willing to negotiate.
Also, allow yourself (and/or your team members) to give a “promise-by” response, which simply says, “Got your message. Need to do X, Y, Z before I respond. Will respond by TIME/DATE.” The key to making the “promise-by” response work is you’ve got to follow up with integrity. If you say you’ll respond by 11am today, then be sure to respond by 11am today! You can also add a “prioritization option” in there, which says, “I’ll respond by 11am today, unless you feel this is more important than my meeting with Customer X in which case I’ll need to find someone to meet with them. Please let me know by 8am if you or someone else can take the customer meeting.” Giving your boss choices like this pushes options at her, which she may or may not take advantage of, but at least you’re giving her the chance to do her job and make decisions.
The second problem I see: end running.
Your boss is doing an end run around you by going directly to your team in ways that make them uncomfortable and confused. While you don’t necessarily need to be in the middle of every communication when things are functioning well, in this case they aren’t. The good news is that this gives you an opportunity to make yourself more valuable to your boss personally and strengthen her belief that “you’ve got her back.” However, it also means stepping up to some additional responsibility. A good solution is to ask your boss to cc you on all requests to your team (and ask team members to forward them to you if the boss forgets). This allows you to set priorities for your team and when it’s not clear to you, get with your boss to have her help you set priorities. This prioritization can feel like a thankless task if your boss isn’t good at it, but think of it as the reason you get the big bucks. When you do it well, it burnishes your personal brand.
Should you respond via email or in person? Yes. In the event the boss is extremely unreasonable and you end up in discussions with HR for any reason you need things like this documented. That said, you can nip a lot of problems in the bud face-to-face. When you have the option, use face-to-face and then follow up in email to confirm your agreement.
Incidentally, when I was in your shoes, I followed a lot of these strategies and made my new boss think highly of me while managing to keep my team sane. Once we were in sync I quit, in part because of her slave-driver mentality. I didn’t leave her in the lurch and to this day we are friends and professional colleagues, having helped each other in various business capacities over the years. It can be done.
Good luck earning the big bucks!
P.S. – What’s your workplace challenge? Write in and tell me about a frustration you’re facing at the office. (It’s anonymous!)