stuck in the middle

You all are such good advice-givers, I thought I'd run another one by you. There's also an update on yesterday's situation at the bottom.

There's a lot of back story here I could get into, but I won't. I'll sum it up: Gary, my boss, hired his best friend (and now my friend) Emily, as his second employee to help him run his business two years ago. I was next about 3 months later, a stranger to both of them, but now a friend as well. They never learned how to communicate as anything other than friends, which at first was fine, but now that there are close to 20 of us in the office, and stress has been through the roof lately, it causes problems. And I'm smack-dab in the middle of them, both as HR and as their mutual friend.

Emily says Gary takes her for granted, and Gary says Emily doesn't follow all the steps and rules that she should. Emily thinks Gary doesn't listen to her, doesn't believe her, and dismisses her too often, but Gary thinks that Emily should open her ears and listen to all the instructions and not take everything so personally.

They're both flighty as hell, late everywhere they go, change their plans on the fly, and have a great time together socially. But in the work environment, unless they're creatively problem-solving something together, with no time constraints, or budget for that matter (when does this ever happen? never), they can't seem to communicate.

And I've found myself in the middle. Here's the current problem: Gary needed to go visit a client, and being Gary, he waited til the end of last week to plan the trip for this week. Emily was already at a client's office last week so the plans for this week were made without her input. Gary assumed Emily would go, but she had already made plans for the week including follow-up meetings with the client she was just with and putting together an ad that we need to submit by Friday. So she did not go. There was talk on Monday, just before Gary left, of Emily flying out Wednesday. She agreed to this, but Gary and Emily got in a fight later that day because he promised to help her with a document for a client but ran out of time because of other meetings. Somewhat in retaliation, it seems to Emily, Gary hasn't called Emily since. Gary's assistant sent him an email yesterday to ask what travel plans had been made for Emily but got no response. This morning, Emily texted Gary's partner, Wade, who's with Gary, (why not text Gary himself... well Emily believes she's getting the silent treatment, so she's giving it back) to say "I'm pretty sure I'm not going to the client's office, but some notice would have been nice." She received a text back that said "I'm pretty sure you are going next week." Emily is now up-in-arms thinking that Gary, again, is making travel plans for her without consulting her. And she's still waiting for help on that same document.

I was tired of hearing it, and I needed an answer on something else from Gary as well, so I sent him a pretty stern email about how he needed to make more time for us when he's out of the office because we can't function for long without at least some input. He finally called the office, a little sheepishly, and is being passed around on the phone now. Emily's turn, and she's being pretty short with him. "Yes," "no," and "okays" with small explanations in between. Not rude, but maybe a little curt-- not her normal self. But at least she's getting the answers she needed to her questions. One problem solved.

I have no idea how to get them to better communicate. They're teaching each other how to treat each other, playing "silent treatment" games, like little kids. They went to lunch one day last week to try to hash it out, and they came up with a safe word one is supposed to say to the other if one starts to feel they're slipping back into bad habits. We can see how well that's going.

Most of the time it's ok, there are just flare-ups. It's definitely worse when Gary is gone because his scarce free time is even more hard to get.

Emily and I just made a run to Sonic. A cocktail would have been better, but milkshakes will work in a pinch. She felt better after her call with him-- all she needed were a few answers, and he was nice to her. Simple, but it solved it. I'm still trying to figure out either a) how to get out of the middle without pissing either of them off and still being their friend or b) how to get them to better communicate, which is what I really want because it would improve our company too. Any words of wisdom?

Update on yesterday's post:
I let it go. For now. I'm doing exit interviews next week for all of them, and I plan on bringing up his absences then. He just submitted his self-review form to me and on it it states that he'd like to continue to work for us until he graduates in December... apparently he missed a couple classes that he didn't realize until a couple weeks ago. Bummer for him. So I'm going to have to both let him down easy, as we don't want to keep him on, and try to teach him a lesson at the same time. Fun for me. I'm chalking it up as a learning experience, and that's made me glad for it.