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Rudolph Araujo's ramblings on the world, my life, my work and oh yeah security!
The Art of Managing Up – When Sucking Up Isn’t Gonna Cut It!

It seems like the latest trend in blogging seems to be coming up with top 'N' lists of things and not to be left out I decided to come up with my own list. Guy Kawasaki is probably the uncontested leader in this area with his Art of Pitching for instance, Joel on Software and the Art of Interviewing if I can call it that. More recently (and really what I think ended up inspiring this post the most) was Mark Curphey with his Top Ten Tips for Managing Technical Security Folks. Anyways so I sat down to think about what is it that I can write about that would help someone reading this post and perhaps strongly related and more importantly – what is it that I know (or at least I think I know) something insightful about!

So here goes – The Art of Managing Up. A lot of focus during management training is always managing down: how to deal effectively with your staff etc. I haven't come across too much on managing up. In fact I personally think this is one of those skills they should teach you in school and college. In my humble opinion along with your core skills – this can be one of the more important factors that can influence career success both if you're the type who likes to stay at the same job for years together or if you're the job hopper who needs a new challenge every two years or so (if you're the type who likes to jump jobs less than every 2 years and it shows like a trend – I would work on that since that is going to be a huge red flag on your résumé!) Needless to say this post will probably be updated every so often so apologies upfront for the repeated entries that might show up in your RSS reader. I should also apologize upfront about the length of this post but hey I figured there was stuff to be covered and I put some pretty pictures ;).

One caveat that I think is important is that all my experience has been with smallish companies, mature startups if you will so it is possible I think that some of the advice below may not apply in your case, especially if work for a really large company. Also I have always worked in technology so this is really focused on developers (and security consultants J) and the like.

So where am I coming from? Well during career I have had the opportunity to work for a number of different managers and each of them had their own management styles which made them a different beast (no offense J) to deal with. For the most part I was lucky to work for people I really liked working for. I might not have agreed with them 100% of the time but I respected their opinions and I think they respected mine. I have also learnt from all of them and all of my coworkers along the way about what works and what doesn't. Some of the stuff below, I have learnt from my own screw ups, others from seeing people around me. So with that said lets dive into The Art of Managing Up.

First for some prerequisites. Essentially without these it wont matter how well or badly you implement the rest of the advice.

Now for the real meat of this post. Let's call this the framework for managing up ;).

  • Be good at what you do – This might seem obvious but it is really important to be good at whatever it is that you do. You are not going to have much success managing up if you don't have the respect of your manager. Let's face it if you are a programmer you better be among the best in at least your team (if not the entire organization or the industry possibly ;)) if you are going to impress and successfully manage your development manager. This is also the part where you get to hear how you need to work smart and not necessarily work hard. In my experience, people who are good at what they do tend to at least appear that they don't need to work as hard to achieve the same results as the other people in their team. With all of this said though your performance is only part of the equation. As my graduation speaker at CMU so eloquently put it being successful is a combination of performance, image and exposure. And surprise, surprise performance isn't even the most important of three! So the rest of this post really focuses on the other two and attitude in general.


  • Listen – don't just hear the boss – This I guess is another cliché of sorts. One thing that I have learnt is that it is always important to read between the lines when the boss says something. This could be in a one-in-one setting or in team meetings. Why is this important? Well very rarely are you going to find a boss that always speaks their mind especially when you or they are new or if they are worried that being blunt might come across as being insensitive. So the trick therefore is to read facial expressions, body mannerisms etc. It's all the stuff they tell you to focus on when you are interviewing someone or going on a first date or dealing with any kind of relationship. Things to watch for expressions like: "Yeah that's great but I think this might be better …" or some other version of that. Well chances are if something else might be better then chances are what you originally did wasn't that great after all. Well don't leave it just at that, first figure out if he / she has a point. Did you really miss some angle? If you don't think so ask the question and make the case for your solution. If on the other hand you agree with the boss then consider the lessons learned from this experience, how can you make sure that next time you do have the truly great solution. Essentially in my experience learning from previous failures, mishaps or even small and seemingly inconsequential mistakes is one of those skills that managers truly appreciate – well the good managers at least J. On a different note, when it comes to listening, try and understand where your manager wants to go strategically and help realize those strategic plans. Often times, they might have a grand vision but possibly may not have formulated all the mini steps it is going to take to get there. Well take the initiative and go beyond the call. Try and see what you can do to help realize their vision. I think it is fair to say that the most successful relationship is one where your personal success makes your manager successful or perhaps it is the other way around. Either way you get the point.


  • Under promise and over deliver – Cannot be said enough. Always, always set expectations. This goes way beyond just managing up but with regards to this I have always found that it is best to be conservative in your expectation setting. Essentially if you think you can achieve something in 10 days well say it will take 12. Those extra two days are not meant for you to be slacking off ;) but more for you to look good when you do in fact get done in 10 days. That's the key in your mind this is still a 10 day task. A lot of people in my experience tend to do the opposite, and I am as much guilty of this as the next guy. The temptation is to think that being aggressive in setting expectations will win us the goodie points, problem is that only works fine when we can achieve those expectations. The one time you slip a date, it hurts a lot more with all the times you did make the date put together. Now of course the trick here is to not take this too far i.e. don't set expectations that just seem like your lazy ;). I guess it is something that you learn from experience – what your limits are and how much can you achieve in a given amount of time.


    UPDATE (based on input from JD Meier at Microsoft): On a related note it is also important to know what to promise. This is where it is important to understand what is it that makes your boss successful and how can you help to make him / her successful. This is many ways the main mechanism to make sure your manager is going to be happy: something you excel at makes him / her look great before his / her manager. One other thing that JD brought up that I think also falls in this realm and is perhaps not completely clear in the paragraph directly above is that you should not be afraid to pushback at your manager to prevent your plate from over-spilling. It does go back to the under promise and over deliver. It is too late at the end of the project to say "well, I really thought it was too much work and I wish I had told you that at the beginning". Resetting expectations and negotiating and prioritizing tasks with your manager are key aspects of a successful relationship – as long as again you are not doing it to avoid work but to produce higher quality work.


  • Over-communicate, always – Most managers I have worked with probably had their biggest irritant as not being "in the know". For better or for worse always over communicate. This includes both times when you are doing well and when you are struggling. For instance, if you are running behind on a schedule, let your manager know early rather than later. This goes back to the under promise and over deliver again. A lot of times we tend to think that we will be able to catch up, but like anyone who has debugged that last, nasty memory leak, sometimes things go wrong and you don't catch up. Guess what you would have been a lot better letting the boss know right the first instance you knew you were slipping. Same thing with good news sometimes, don't wait for this to be your big surprise. Remember this is your boss not your grandparents! If it turns out he / she would have rather had you working on something else again your surprise might work against you.


  • Argue like hell but when the decision is made get in the boat and row – This is something one of my first managers used to say. The idea being don't be afraid to speak your mind and argue your point – in fact if you think you will "not get away" with ever disagreeing with your manager perhaps it is time to look for a new job. Now with that said, after the decision is made learn to accept the decision and work to make it successful. Don't be rooting for failure just to prove yourself right even if you are 100% sure you were and are right. In my mind when a team fails, you aren't going to become a superstar by saying "I told you so". If this does happen too often though one might question whether your manager is even open to suggestions and ideas or is this one of those autocratic managers who "never needs to listen" or "always has the best idea" again maybe it is time to move on (see the section about liking something about your boss and mutual respect above).


  • Pick your battles – Along similar lines as above, if you are going to put the stake in the ground for something make sure it is a battle worth fighting. And what defines "what is worth" well that's for you to judge. It might be the free drinks being taken away or it could be using a specific technology development platform. If you fight for everything pretty soon no one is going to be asking for your opinion anymore.


  • Ask for responsibility, don't wait for it to be given to you or expect it will happen automatically at some point – This one is probably one of the most important in my mind. Again one of my first managers gave me this advice. A lot of times as employees we tend to be shy to ask for more responsibility lest we "speak out of turn" or "step on anyone's toes". The problem though is if you don't ask for more responsibility in my experience no one will give it to you. Sure you will get a tad more responsibility (if at all) each time the annual reviews come around but if you are looking for faster career growth that is probably not going to be fast enough. Now granted there is also some risk with this approach, so you better be good at self assessment – how much responsibility can you take and accomplish successfully so that your boss is left impressed and not disappointed. Ask for only as much as you can take and deliver on it. Then maybe you can ask for more. I think to some extent though you should not be afraid to fail, it tends to make you a bigger risk taker but then risk takers only look good as long as they don't crash and burn ;).


  • Don't take anything seriously when the boss is yelling – Let's face it we have probably worked at least someone who is a screamer ;). Typical scenario is they are having a not so great day – perhaps their boss is leaning on them too hard. Anyways you go in to get something reviewed and they find the smallest of issues and begin to yell, insults and the like. What I have learnt is people usually don't mean all of what they say when they are throwing an anger fit. In fact more often than not they are in fact explicitly looking to be hurtful just to make their point! I believe the best thing to do in these situations is to duck for cover at the earliest possible moment i.e. just keep quiet, keep your cool and get out of the firing line as soon as possible. Don't take anything that was just said to heart but wait for a day or so and then go back in to have a chat and present your point. Before doing that though sanity check your argument or whatever it is you were presenting with a co-worker who will give you an honest opinion. If you believe you were just the victim of collateral damage then by all means attempt again when heads are cooler. The main thing though is to never let someone in such a position either bully you or make you feel real bad or insulted. Needless to say if this happens way too often then maybe you should be looking for a different boss and leave him / her with a free voucher for anger management classes on your way out ;).


  • Don't burn your bridges – At many points in this post I have (sometimes half jokingly) suggested it might be time to move on. The fact is at some point the time might come for you to look for greener pastures. When this does happen make sure you handle it as best possible. Be flexible with your exit plans and don't leave in a huff or with a pile of unfinished work left behind for someone else to cleanup. Avoid also any nasty arguments with either your coworkers or your boss. It is common to assume that "hey I don't have to work with them anymore I might as well give them a piece of my mind". In my experience no matter how bad they were it is probably best to not burn any bridges. Hey you never know when you might have to come back to them or need a reference from your ex-manager or (and it has been known to happen) six months after you leave company X to join company Y, company Y hires your ex-manager from company X and suddenly he is your manager or perhaps your manager's manager again.


  • Don't compete with your coworkers – To be quite honest I wasn't too sure about putting this one in. I think in life you are always competing with people around you. The aim though is to keep that competition healthy. Bottom line is try to work hard and make yourself look good rather than spending your effort making the other guy look bad. Why is this important from a managing up perspective? Well it is because the best managers I have had the opportunity to work with have immediately since this for what it is and you end up doing yourself a disservice more than anything. Let's just say it's kind of karmic thing. You can bet that if you are spending time trying to throw your coworkers under the boss before your boss they are spending at least the same amount of time if not more doing the same to here. And no matter how good you guys are at your jobs, the fact is that is not a conducive environment for the best productivity so give it a rest and let everyone's skills and work do the talking!


    UPDATE (based on input from JD Meier at Microsoft): Turns out sometimes you might have to compete with your co-workers, for instance, during the brain storming phase of a project where people might present many different ideas of which one will be selected or if you are competing for budget or resources. In such cases certainly put you best foot forward. But again once the decision is made like I said above get in the boat and row. Verbatim from JD since I could not say it any better: "At the same time, be a mentor and team player for your team mates. It's a better long-term strategy than trying to out-do. As far as true competitiveness -- internalize your bar. Make sure you are constantly becoming a better you … a little bit at a time. The little bit adds up. It's how John Wooden built the winningest basketball team. He made each player focus on their own improvements." I think his last point is especially key – always compete with yourself.

Footnotes: One of the best classes I took at CMU was Organizational Power and Politics. A lot of the learning I did there was relevant in a very real way in my daily life and in my career. Some useful reading that came out of there was the work of Robert Cialdini. If you haven't read his books on influence you should. Another interesting learning was the Stanford Prison Experiment and of course what class in politics is complete without a reading of The Prince. The course text was also great which was by Jeffrey Pfeffer - Managing With Power: Politics and Influence in Organizations, another must read.

Posted: Saturday, July 14, 2007 12:34 AM by rudolph
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