Teach me, Obiwan.
January 27, 2012 12:30 AM   Subscribe

I have a new boss. He is awesome. Now what?

My previous boss was awesome too, but he works out of a different city which made things difficult to develop any kind of synergy with him, especially since we were lucky if we could sync our calendars well enough to get an hour-long phone call once a week. My boss before that (the bosses' boss who was filling in) is generally a decent guy, but a TERRIBLE authoritarian-type manager, and has established a culture of fear & CYA. Outside of the office he is the life of the party, inside, you avoid him like the plague. His morals and ethics are not outright bad, but often make me uncomfortable. My two bosses before that were fun, cool, engaging people but were largely inept, ineffectual leaders - almost useless.

My new boss started last Monday, and uhm - wow. I didn't know much about him before he started, but he's made a big impression on me and my team over the last 2 weeks. He immediately jumped in helping us resolve some project issues, he asks very thoughtful questions, we've chatted for 2+ hours multiple times, he's given great advice, etc., etc. Best of all, he's already picked up on our culture issues, process issues, project management challenges, on and on and on - and none of it surprised him and he's keenly aware that there is a lot of work to be done. He's a level-headed, calm, positive, encouraging, knowledgeable, inspiring dude.

Now what do I do?

I've suffered through a few years of poor leadership at this job, 8+ years prior with various other mediocre bosses. I feel I've gotten pretty damn good at working with sucky bosses so now I don't know how to make the most out of this more than competent one.

My instinct is to follow him around everywhere like a lost puppy and ask a ton of questions, but there's actual work to be done and I don't want to set the wrong tone that I don't know what I am doing. But damnit, I'm so effing excited he's here! By the way, it's not just me - all of his other direct reports feel similarly.

How do I best take advantage of having a good boss? What are the best practices here? What kind of questions or feedback should I solicit? How do I not become a brown-noser or be over-eager? He's been hands-on during the crisises we've been dealing with this week, but that is not the norm. I truly feel like I can learn a lot from him and he can help me become a better leader & manager.

Thanks for your help and insight in advance!
posted by SoulOnIce to Human Relations (15 answers total) 14 users marked this as a favorite
I just had an awesome boss last year. I can totally empathise with this. The three things that I did: I tried to be the person I thought she wanted me to be. If I was in a tricky situation - even if my first impulse was to call her/ask her for advice, I would ask myself (seriously!) "What would Connie do in this situation?". Then, if I didn't do it outright, I would then give her a heads up, bundled with my proposed course of action. Finally, I would think about what I really wanted to talk about + questions in our regular meetings.

Don't worry; you don't have to do too much with an awesome boss; that's the beauty of it, they're such great communicators they will let you know what to do, and you'll feel brilliant all the while!
posted by smoke at 1:09 AM on January 27, 2012 [4 favorites]

Why don't you just ask him? In my experience, great bosses want to help people to grow, and are more than happy to help you.

Set up some time with him to talk in private. Tell him exactly what you've written here - "You're the first boss I had who really helped us, I want to learn as much as I can from you but don't know where to start." Most bosses want to set clear expectations to you and will help you.

Personally, I much prefer it when my group asks me these kinds of questions instead of trying to figure it out on their own.
posted by xmts at 3:34 AM on January 27, 2012 [5 favorites]

Do your job. Do it well.

Seriously. You should have less to worry about in the near term, at least, about the culture of fear, etc etc. You should redirect the negative energy you had previously and redirect it into making sure your new boss looks good.

If he's as good as you seem to believe, he should also be one that provides air cover. Which means, he'll provide a layer of protection for you folks. So he's going to need help in looking good. Get stuff done, make sure the immediate impact he's making with you is noticed through his goals and deliverables being seen in a positive light by his bosses.

Also, as xmts says, set up some time with him to talk. You want to make sure what his expectations are, and to help him out be successful, here's the lay of the land as it has been. Don't bash anyone, point out what people's strengths are, and what you see as some of the challenges the group faces.

Before you end, just re-iterate what he expects of you.

Now - these things can go a couple ways. If he gets the support of his upper management, it could go well. If they come down on him for making waves, it'll depend on what he wants to do. Remember he has bosses to answer to, as well, so supporting him is a big part of it.
posted by rich at 4:28 AM on January 27, 2012 [1 favorite]

Best answer: 1. Do your work.
2. Provide accurate accounts of how you spend your time and what you are working on.
3. Be funny but professional.
4. Over time, describe the roadblocks which impede your performance. Treat this like an ogre or like an onion. There are many layers, peel them back one at a time.
5. Properly praise your co-workers directly to your boss.
6. Get organized, stay focused.
7. Keep them abreast of the big issues, not your day to day stuff - unless your day to day stuff is at risk of impeding timelines and/or becoming a big issue.
8. Don't badmouth people, clients, other branches of your organization - let your boss figure it out.
8a. Corolary: sometimes it is appropriate to help someone encounter difficult branches of your organization on small tasks so that they are prepared and not blindsided by the difficulties other people will present.
9. Do not badmouth your boss from 2x ago.
10. Don't say "that's not how we do it" unless your new boss is asking how to do something. If your new boss is telling you how to do something, appropriate questions are "how high?" and "for how long?"
11. Clarify. Clarify what your task is, the task that is being asked of you, and any expectations your boss or you may have.
12. Inform your boss of adjustments to timelines from changing priorities.
13. If you want to eventually be a manager or a leader, or take "the next step" in your career, tell your boss in a 1:1 session and ask them what steps they took to do it, for constructive advice on how to get there, and what they would estimate an appropriate timeline for you to get there would be.
posted by Nanukthedog at 4:40 AM on January 27, 2012 [20 favorites]

Remember all those things that you knew were good for the company but didn't do when your bad boss was around? Do those things.

Remember all those things that you didn't want to do and knew were bad for the company but did anyway when your bad boss was around? Don't do those things.
posted by valkyryn at 5:26 AM on January 27, 2012

Best answer: At the risk of being a wet blanket, you do seem a bit puppyish. Be careful not to develop a work-crush or any other sort of crush. Keep personalities out of it, including the bad bosses from before. If I inherited a team of people, I'd welcome a few conversations that are part getting-to-know-you, part learning the ropes, and part learning the you-are-here, meaning what's been done right, wrong, etc.

But if it got laid on a bit thick by a subordinate, I'd become a bit worried - what is his or her motive? Remember, he has a lot of other things to figure out as well. Also remember the difference between being friendly and being friends.

I'd concentrate on continuing to do your work properly, with an eye toward making improvements as you go as you are enabled to do so by a boss who sounds like a good listener.
posted by randomkeystrike at 6:08 AM on January 27, 2012 [5 favorites]

I have an awesome boss and get where you're coming from. But yeah, don't overdo it. Just show up to your meetings prepared, ask good questions, and listen to the answers. Know your own work really well and identify your chronic problems and challenges.
posted by Miko at 6:15 AM on January 27, 2012

Do your job.

Focus on doing your job. You already know how.

You have a ton of time to learn things from your new boss, so keep that in mind. You don't have to absorb all his knowledge at once (nor is that possible, nor do either of you have time for that). When you have questions -- real questions, specific questions -- ask him. Otherwise, hold off on the mentor stuff for a while. Eventually, sure, have coffee with him and talk about big picture things concerning you, but let him get settled in and let yourself get settled in with him as your boss first.
posted by J. Wilson at 6:18 AM on January 27, 2012

On badmouthing: I refrained from talking about my bad boss to my good boss for about 6 months. I let my bad boss's demotion and their new level of interaction speak for itself. Only after I was prodded on multiple occasions, and my new boss stopped describing my old boss's methodology as "...interesting..." and started saying he was short-sighted and that he understood the demotion. Only then did I let it slip that my old boss was an idiot.
posted by Nanukthedog at 6:36 AM on January 27, 2012

Seconding some other people, I would SELECTIVELY run the occasional plan by him, having prefaced it with the fact that he's new and you want to make sure you're in sync with the way he wants things done. You're putting yourself out there, in that he might learn he disagrees with your decision making, but it's likely he'll agree with at least your thought process and appreciate that you want to take things in his preferred direction, yet come to him with a thought-out plan.

If you're worried you're not showing him how much you appreciate him, don't. That likely is obvious.
posted by troywestfield at 6:46 AM on January 27, 2012

I have a boss like this; always there for you, always willing to pitch in and figure things out, etc. But, he wants everyone on my team to get to the place where they are only coming to him with the hard stuff. The people in my group who get the promotions and the best projects are the ones who work independently, make their own decisions, and give him updates regularly. The ones who have been stuck for years are the ones who can't advance a project on their own even after years of coaching.

So, yea, I am just echoing the other folks who say not to overwhelm him with your enthusiasm.
posted by cabingirl at 7:39 AM on January 27, 2012

I had the best boss ever. I nearly cried when he left. He was so afraid to tell me too because he knew I was going to be screwed with the reorg after he left. He was right.

Here is what I did.

My job. Be enthusiastic, do research, bring new ideas to the table, keep trying
Be professional to others. Your attitude to others does come around. If you're nice, professional and he/she sees that, when you come to a jerk, the boss will stick up for you, not the jerk.
Be honest, open yet professional.
Sense of humor at least in my case worked
Without being a jerk about it or a know it all, call others out on their b.s. We had a vendor say that no agency provided comps to clients. I knew that was wrong. I showed sample comps from my former agency.
If you can save money or make money, show those ideas.

I saved the company $60k out of a $140k budget. Not bad.
posted by stormpooper at 9:48 AM on January 27, 2012

Don't keep thinking of interesting questions to ask him, that will drive him insane! Also no small gifts, sulking when he doesn't reply to emails that don't need a reply, competing with others for his attention, or stopping by just to say hi frequently. Being a great employee is all you need to do.
posted by meepmeow at 10:22 AM on January 27, 2012 [1 favorite]

Best answer: My instinct is to follow him around everywhere like a lost puppy and ask a ton of questions, but there's actual work to be done and I don't want to set the wrong tone that I don't know what I am doing. But damnit, I'm so effing excited he's here! By the way, it's not just me - all of his other direct reports feel similarly.

As often as possible, just go shoot the shit with him or whatever...I have a great boss, and sometimes I'll open the conversation with wine tastings or tennis, just to put everything at ease and make sure they don't feel like you're making them the ANSWER MACHINE OMG.

Also, this person is new, and even though they might be super knowledgeable, they're just getting their feet on the ground and might be reluctant to do anything against established policy or history until they've figured things out first.

You have to be really careful to learn exactly how they want to work -- I had a boss I liked who randomly got upset with me for cc'ing him on emails -- he felt like it was a passive aggressive way of telling him I wanted him to do the work for me. Historically, I had done things like that at other jobs just because managers wanted a sense of what was going on. I still do that. But that one guy REALLY did not like that, and since we were new to working with each other I didn't know why and he didn't know why I was doing it and it wasn't great for our relationship going forward.
posted by sweetkid at 10:45 AM on January 27, 2012 [1 favorite]

Read some articles on How to Manage Your Boss. Analyse your boss' style. How much information does he want? Start giving him lots of information, and ask him to let you know what level of detail he wants. No surprises - let him know of trouble spots. Ask him for some time so you can review the work you're doing, so you can be sure you're doing the right work. He may be swamped with people doing this, so give him some time to get up to speed.

Look at his record and see where he has expertise that you lack. Ask him for coaching, if he has time and inclination.
posted by theora55 at 2:23 PM on January 29, 2012

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