Two hours in a car with my new boss
May 31, 2011 5:19 PM   Subscribe

Help me survive two hours in a car with my new boss.

After a month at a new job -- a small company where I interact with my boss almost daily -- I found out that my boss and I are going to a meeting several towns away. She will be driving me there and back, and the trip is just over an hour each way.

Though my boss is generally pleasant and seems happy with my work, I'm somewhat nervous about traveling alone with her, for all the normal reasons, like general awkwardness.

What's worse is that my co-worker told me that the boss has admitted that she (the boss) has "no people skills" and "will ask anything." My co-worker personally experienced this on a commuter train ride, which the boss turned into an impromptu performance evaluation, right in front of other passengers.

My question is, how can I prepare myself for this trip? What topics of conversation should I try to focus on -- and avoid? If things start to get weird, how do I handle myself? I've only been at the job for a month so I'm not sure how secure my position really is.

Thanks for your help.
posted by Flying Saucer to Work & Money (16 answers total) 2 users marked this as a favorite
Could you be proactive and discuss things to listen to on the trip? Maybe your boss and you can decide on a podcast or something that will limit the amount of free conversation.
posted by xingcat at 5:30 PM on May 31, 2011 [1 favorite]

Best answer: Spending time with the boss is always a good thing. It helps build relationships and it helps build trust.

The best way to avoid a performance review is to come prepared. Is there something your boss knows a lot about professionally? Something that you can learn from? Have a list of questions handy. Asking about the history of your company is also pretty good.

However, not everybody wants to talk shop all the time. Come prepared with questions about family - everybody likes to talk about their kids and their pets.

Finally, don't shy away from the performance review. It's no big deal. But try to go on the offensive. If the conversation is too much about you, start asking about her (in as polite a way as possible).

Also, be content to sit quietly, and let your boss lead the conversation.
posted by KokuRyu at 5:41 PM on May 31, 2011 [6 favorites]

It's possible that your co-worker has different people preferences than you do. Nobody has no people skills; it's all relative.

Firing you is probably not on your boss's mind. Personally, I'd try to think of the boss the same way I'd think of any other person who I knew as well as that boss. For instance, I'd keep reservations about my new job to myself, but would feel free to share my opinion on how [favorite local sports team, philosophical pondering, etc.]. If the boss tried to steer into conversational territory where I didn't feel comfortable, I'd just try to steer it right back out.

Sometimes I'll ask questions that I wouldn't mind answering that other people would mind answering. I have no problem with them not answering those questions; I'm just looking for a good conversation.
posted by aniola at 5:42 PM on May 31, 2011 [2 favorites]

I often have to deal with this (I work for the railways, which often means 2+ hour train trips with clients) and I hate it, so I totally sympathize.

If I can do work, I try that (not easy in a car). Or sometimes I make my excuses and throw in headphones and (pretend to) sleep.

Podcasts as suggested might be a good idea, or if you feel comfortable about it, suggest that you each make a mix cd of your favorite songs (hopefully this comes across as showing interest in her personal taste).
posted by smithsmith at 5:45 PM on May 31, 2011

Oh, and I sometimes pretend I have an appointment or meeting to get to afterwards so I have to take my own car. That's right. I'm so neurotic I'd rather pay $20 in gas money than suffer a couple of hours of small talk.
posted by smithsmith at 5:48 PM on May 31, 2011

Keep the conversation about work - preparing for the meeting / talking about how the meeting went, asking questions about the company, your department, her experience, the politics etc. Keep asking questions.

If she's a self-admitted "non-people person" then personal questions may not get much of a response and she may not be particularly interested in your personal life.

Getting feedback on your performance thus far is probably not a bad thing - it's in an informal context and will give you an idea about how you're doing and what you need to demonstrate more of - so don't shy away from this if she wants to talk about this.

Radio is always a good thing - masks awkward silences and gives you something neutral to talk about.

Oh, and don't fall asleep with your mouth open and dribble. It's not good. Trust me.
posted by finding.perdita at 5:48 PM on May 31, 2011

Best answer: Since you've only been there a month, I wouldn't worry about a spontaneous performance review. Are there any genuine questions you have thought of since you started that you would like to ask your boss? Asking a question to show off or criticize/confront a policy is likely a bad idea at this stage in your position, but if you have a true question that won't be confrontational or show-offy, I'd use the opportunity to ask it.

Otherwise, sometimes people who admit they "have no people skills" will take direction from others in conversation and social situations. I agree with KoKuRyu that you should be prepared to let your boss lead the conversation, but you have the right and ability to steer the conversation to where you feel comfortable, as long as you show respect.

Good luck and let us awkward internet introvert voyeurs know how it goes!
posted by shortyJBot at 6:26 PM on May 31, 2011

Questions that encourage technical gossip are probably a good bet - things like the history of the company (naming names), why the founders thought it was a good idea, what the competition is up to, juicy dirt on the competition, freewheeling reminiscing about colorful characters in the company/industry's history, that sort of thing. It's not directly personal so nobody in the car will get offended by poor social skills, but it's deliciously satisfying gossip nonetheless. Plus, it's the kind of thing you're not likely to talk about at the office, so it's a great way to get up to speed on the backstory and "inside baseball" stuff that will make you an insider sooner.
posted by Quietgal at 7:24 PM on May 31, 2011 [2 favorites]

Oh, I do this quite a bit-- the awkward two-hour drive with your boss. Don't worry! One hour will go by quicker than you think (consider that a solid 5 minutes on each end will be spent just navigating) and it will help you build a stronger relationship with your boss. My suggestions are:

* Check the weather for next week. (This is lame, but just wait. You're going to talk about the weather.)
* Review the biggest news stories over the past two weeks or so. Find two stories that you think you can competently talk about (maybe Apple's announcement next week? Or whatever) and skim the other headlines. It sucks if your boss is like "Did you hear the latest in Libya?" and you're like "No, actually, I prefer to watch cartoons after work, so I know nothing about the outside world." It's much better to say, "Hmm, I hadn't. I've been so focused on the upcoming Apple announcements! But tell me about Libya!"
* If your boss is into sports, check the sports headlines.
* Think of a few client/project-specific questions.

Questions you should consider that are work-friendly:
* This is a nice car. How do you like this car?
* How long have you been with (company)?
* What were you doing before you started here?
* What are you doing this summer? What did you do last summer? Last weekend? Next weekend?
* Is your family nearby, or do you need to travel to visit them?

Finally, always remember:
"I'm enjoying my position here, I'm learning a lot, I'm glad to be part of the team and I hope you'll let me know if there are ways I can keep adding value."
posted by samthemander at 8:01 PM on May 31, 2011 [6 favorites]

You could suggest early on that you've been taught that engaging the driver in conversation distracts the driver, so you routinely try to avoid doing that. And then, you can sit quietly, contentedly, and silently admire the scenery. Answer direct questions or comments made to you succinctly, yet thoughtfully. But do not ask any questions, or initiate conversation in the car.

Be socially chatty at the destination, and at your return point. Make a point of following up with comments/questions about the trip and the meeting, to your boss the next day at work.
posted by paulsc at 8:13 PM on May 31, 2011

Seen any good movies lately?
Try any good restaurants lately?
Read any good books lately?
Go to any concerts/shows/plays/theater/etc. lately?

Think of the sorts of topics that you talk about when you're getting your hair cut - benign but universal questions that hopefully feed into other topics.
posted by gatorae at 8:31 PM on May 31, 2011 [1 favorite]

Is this a new destination for her? For you? Can you ask (or talk) about what location X is like?

Also, I hope you won't have to use this tip, but if you're driving in car with a boss who's a frighteningly distracted driver, offer to check their Blackberry for them. For your own safety.
posted by deludingmyself at 9:04 PM on May 31, 2011

I like the suggestion of specific topics that others have already suggested. Alongside a willingness to let her/him do some talking and all of those more regular conversational things I would suggest that you think about something that you know a bit about that is easily approachable and interesting to others. For example, I regularly chat with people I don't know well about my slowly-being-built apartment, my time working Turkey and my bike-riding to work. I can waffle about these for a while and they are fairly easily interwoven into most conversations (Turkey less so, but that one gets around so I get asked about it). What I like about these is that they have the capacity to get at least a good paragraph's worth of conversation out of them, and I am confident talking about them.

I don't think you should assume that your boss wants to do all the talking and that you can sit back and politely go along with it. Great (if slightly boring) if this does happen but conversations are work, and I would want to show that I could hold my own end of the bargain.

Probably you will have long periods of silence, too, which I think is fine as long as they're not happening really early. 2hours is a lot of conversation with that power dynamic.

Finally, if you know of other similarly good wholesome and interesting things that your boss could talk about (their recent trip to... their background in....) these can show that you are interested and grown up too. I wouldn't recommend doing research or anything. That would be weird. But I think that part of coming across as professional and capable is the ability to make this kind of small talk, and lead the way if necessary. It sounds like a great opportunity. Good luck
posted by jojobobo at 11:46 PM on May 31, 2011

About a month after I made a hire of a mid-level manager-type that reported directly to me, I had to take a 2-hour roadtrip with that person. That roadtrip was great for our working relationship, because it really helped us to get to know each other better, helped my manager understand where I was coming from and what my background and perspective was, and lots of other stuff. So look on this as a HUGE opportunity, even if you both might suck at small talk.

I thought the most interesting things/helpful stuff for these situations is to exchange stories. Not in an interrogation or interview-type situation (heh, no cross-examination, please) but that's how you get to know someone and being in the car is great for that.

So it sounds hokey, but we talked about things like the year the other guy spent working in a foreign city, his side-business in a totally unrelated field that he had for a few years in California. Things where he did most of the talking for 5 minutes or so. And I told him about some of my wackier war stories/litigation cases and some of my non-work-related side interests.

He also interrogated me on some work-related politics and long-term planning, but I think ultimately that was a lot less interesting than the "get to know you better" stuff we wound up doing.

Now, some caveats. Despite the direct-reporting relationship, the co-worker in question and I are within 10 years of age and some similar tech backgrounds. If your boss is a LOT older than you are, then it could conceivably be a bit more awkward and you might have to work harder to find commonality. But I'd still say that the "getting to know you" aspect / opportunity still applies.
posted by QuantumMeruit at 8:30 AM on June 1, 2011

I really wouldn't worry about it - got several lifts home per week from my boss for a few weeks earlier this year and we ended up talking about all sorts of stuff or just listening to music. And yes, I did get a performance review, which was ok. It was just the two of us and she's a very busy lady so getting to talk to her at length about some things was actually quite helpful.
posted by koahiatamadl at 1:57 PM on June 1, 2011

Response by poster: Since you asked, shortyJBot, here's a recap.

The whole experience was almost entirely awkwardness-free. Early on in the car ride, my boss told me that she valued my work and wanted me to be sure to let her know if I felt she was giving me too much to do - which is an actual danger. We had had a bad moment the week before and she brought it up and apologized for her side of it, and I apologized for my side. We talked about where we driving to, which was a new area to me; I had just moved to take the job. We discussed the future of the company - it's small and reasonably young - and where she sees it headed, and my role in it. All very positive (and I'm not implying that I'm a model employee or that she's the perfect boss). I talked about my new apartment and how I was exploring the new city, asking her advice on a few matters. She talked about her kids; I talked about my wife.

We had lunch after the business meeting, which I was unready for, but it was with the client, so we were both able to focus on him. And the meal was pretty good, and free.

On the way back, we both checked in with the office, which meant phone calls and emails, so that took up most of the return. It was a warm day, we had had a big meal, and the meeting had gone well, so there wasn't much else to discuss.

A bad car ride might not have cost me my job, but it would have made for a painful two hours in the car and who knows how many weird weeks in the office, so I again want to thank the Ask MetaFilter crowd for helping me feel better about, and prepare for, this experience.
posted by Flying Saucer at 5:16 PM on June 5, 2011

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