The Secret Art of Managing Your Boss

The Secret Art of Managing Your Boss

I was at a conference yesterday where I gave a talk about how to manage your boss (irony: my boss asked me to give the talk).  The audience was primarily customer service and accounts receivable professionals and they seemed to dig the stuff I said, so I figured it might be worth posting here.  I use PowerPoint for talks like that, but instead of bullet-pointing people to death with a million slides, I try to compress things into a small number a slides and then talk, talk, talk.  Yesterday's talk took about an hour, but I only had five slides-four if you don't count the 'intro' slide.  But I'm digressing…

Since I was mostly talking, I'll have to work up my notes into something that's readable here.  That's why this is 'part 1.'  There will probably be a total of three or four entries on 'The Secret Art of Managing the Boss' and I hope you find something useful.  This stuff is pointed at the workplace, but as one of the participants noted yesterday, she had about six 'bosses' and this information works well for all of them.  She was talking about her boss at work, her family, her outside commitments-all the places where she had to manage a relationship with one or more people.  These relationships don't need to be unequal, like the boss/subordinate relationship, for this stuff to work.  This advice will be adaptable to any of those situations where you have to work with someone else to achieve mutually acceptable goals.  Actually, I guess it'll work even if you are working toward mutually exclusive goals, but that opens up an entirely new can of worms, so I won't venture down that path.

Three Things
The stuff coming up focuses upon three things.  I kept it to three things because it's often said that in any given line of business you only need to know three things.  The trick is in knowing which three.  I don't know how true that is, but I'm running with it.  The 'three things' in the business of managing your boss are: 1) Understanding Yourself; 2) Understanding The Boss; 3) Understanding The Relationship.  Sounds simple, eh?  Like I mentioned earlier, it's highly compressed. 

There is one other element that I think wraps around these three things and affects them.  That's perception.  Perception will get you every time. As you read this, you probably don't perceive it the same as the next person reading the same words.  That holds true for verbal communication, body language, etc.  Our perception of reality is often very different from the reality that others perceive.  Here's an exercise that has great impact in a group setting because it really underscores how perception messes with us.  It won't be as remarkable as you're sitting there reading this by yourself, but I think you'll get the idea. 

Read the following text:

      Finished Files are the Re-
     sult of Years of Scientif-
     ic Study Combined with the
     Experience of Many Years

Got it?  Makes no sense, huh?  Don't worry about that.  Read it again and just count the number of times the letter 'F' occurs. 

How many did you count?  If you counted less than six, go read it again and count the number of times the word 'of' occurs.  In a group of 20 people, 2/3 of them will see the letter 'F' occurring only three times.  Often, you can have them read the paragraph over and over and they'll still miss the word 'of.'  You probably get the idea, but in a group of people, it's a pretty dramatic example of how all of us perceive reality in different ways.  We'll see things differently from the boss, who will see things differently from our co-worker, and so on.

The Secret Art of Managing Your Boss, part 2

Knowing Yourself
Like I mentioned in part 1, this part is about 'Knowing Yourself.' It's not quite as transcendental as it sounds. Of the three things (Knowing Yourself, Knowing the Boss, Knowing the Relationship), I can never decide which is most difficult. I think it depends upon the person. Some folks, who are naturally inclined to look inward, have an easier time really understanding themselves. Others find it very difficult. Regardless, this part is the one we have the most control over. The other two involve, to one degree or another, some other person's whims and idiosyncrasies, and you'll have little control over that. Knowing yourself, however, is completely accessible. Unless you're a total basket case–then it's only partially accessible. You'll have to pay a therapist to access the rest. I'll leave the basket case determination up to you.

Your strengths are those areas that you either are predisposed toward, or have a clear preference for. Even if you have the preference for a particular discipline or domain, but aren't accomplished yet, you should count that as a strength. For example, if you work in customer service, but have a strong interest in finance, you ought to count finance skills as a strength. An excellent place to begin to research your own strengths, from a broad perspective, is the Gallup organization's book 'Now Discover Your Strengths.' There's more info on their website.

Weaknesses are those areas where you know you either can improve, or where you simply want to avoid. Some folks have no trouble talking to strangers (a strength), but struggle with math, and they may want to avoid situations where they are required to do a lot of math. That's fine. A common misconception of weaknesses is that they taint us and ought to be avoided at all costs—as if admitting a weakness means that you necessarily decrease in value as a person and an employee. That's just simply not the case. Everybody has weaknesses since it isn't possible to be great at everything. Some people are skilled at accommodating and adapting around their weaknesses, but they still have 'em. So relax, everyone has weaknesses and you're not alone.


Your personal style refers to your work-style, not your clothes. Do you prefer your workspace quiet or loud? Would you rather receive paper or electronic copies? Would you prefer to read instructions or hear them given? Personal style encompasses all the bits that contribute to a comfortable workplace for you. Explicitly knowing and creating the best work environment for yourself can save you a lot of mental aggravation in the back of your mind.


How you view authority sounds odd, but it's important. Some people have a natural inclination away from authority and then tend to make assumptions about their boss that may not be accurate. Other folks may be inclined to rely too heavily upon authority—seeking a nearly parental relationship, with the same results. Think about how you've dealt with past bosses and understand your tendency. This backward thinking is tough to do and requires absolute honesty, but the payoff can be tremendous in terms of the health of your relationship with your boss.

Yay Me!

Now on to the tipsheet. The tipsheet is arranged in a random order, so don't read into it. The 'Yay Me! File is simply a standard manila folder that you keep good stuff in. Just drop in notes when you've accomplished something great, or if you get an email from a happy customer. Just drop that stuff in the file. Review it when you're feeling low, but especially review it and pass it along to your boss around review time—hopefully your boss is keeping one on your behalf, but just in case, a Yay Me! File is good to keep around. Though your boss ought to be keeping track of your successes and failures, too often they don't. And when review time comes around, the boss will only be able to recall the last few weeks of your performance. If you suspect your boss doesn't keep track of your performance in such a detailed manner, pass him or her a copy of your file a couple of weeks before the review.

Periodic Goals

Establishing periodic goals ought to be something you do in conjunction with your boss, but if you've got a boss who doesn't pay much attention to that stuff, you'll have to take matters into your own hands. Working with some of the ideas that are coming up in part 3, you'll want to establish goals that are in line with your boss's and department's goals and then keep track of progress. Break the goal into discrete tasks that you can spread out over a lot of time. Make it formal—make a spreadsheet, or list it all out on paper, but keep track of your progress, and when you're done, drop that thing in the Yay Me! File.


Dependability seems like one of those no-brainer, common sense things. You know, be at work on time, finish what you say you'll finish, etc. Dependability is a no-brainer, but it deeper implications. Here's the bottom line with dependability: a boss wants to believe that he or she can rely on you or your team. Without that assurance, you will bring micro-management upon yourself. Because if the boss can't depend on you to work reliably, they'll come hang out with you to make sure stuff gets done right. So strive for dependability and discourage your boss from micro-managing.

Double-loop learning

Double-loop learning sounds pretty academic, but it's really simple. It's just thinking about thinking. If you have a historically difficult time talking with your boss, try some double loop learning—think about your assumptions as you enter conversations with them. Think about how you might be bringing previous issues with you. Think about all the factors, large and small, that could be playing a role in how you approach a simple conversation with the boss. That's double loop learning. Just thinking about thinking.

Respecting the org chart

Respecting the org chart is probably the simplest item here. It just means don't jump over the boss's head. Sounds reasonable, but you might be surprised at how many people don't consider the implications of copying the boss's boss on a simple memo. For instance, if your boss's boss sends an email directly to you, it's good practice to reply with a cc to your boss. Keep them in the loop. With that particular scenario in mind, however, understand that if your boss wants their boss to know something, they'll let 'em know. Don't take on responsibility for what you have no control over. If you feel your boss is somehow being negligent and you're certain that they're not passing along vital info, then by all means jump over them, but go easy.

So that's the quick rundown on 'Know Yourself.'

The Secret Art of Managing Your Boss, part 3

Here's the third part of the 'The Secret Art of Managing Your Boss' series. Part 1 is here and part 2 is here. This part is about understanding the boss.  I've included the relevant slide for this section.   Everything that follows comes off the slide.  Click it to get the big version.

Listener or Reader
There's a management theory (hat tip to Drucker) that says that all managers are either listeners or readers.  It's not limited to just bosses, of course.  Everyone can be classified as either a listener or a reader.  The trick is to figure out which kind of boss you have and accomodate their preference.  Listeners need to hear the info first (meetings, phone, hallway, whatever), then they'll be able to consume a written digest.  Readers want the story on paper first so they can have some time to understand the issues and be prepared for a meeting.  Understand the boss's preferred style and use that knowledge to make your life easier.

Under-manage and Over-manage
Does your boss over-manage or under-manage?  Over-managers tend toward micromanagement–they want to be involved with task-level stuff. Under-managers tend toward being uncommunicative as to their expectations.  They'll generally leave you alone to wonder what's next.  You can deal with both of these scenarios by understanding the 5 responsibilities of a manager over there on the right side of the slide, and by understanding the manager's problems.  With over-managers, you'll need to demonstrate the dependability I mentioned in part 2, and you'll need to demonstrate a clear grasp of the details of your task.  Then you need to gently point the boss's attention back to process details and away from task details.  With under-managers, you'll need to insist on completing the feedback loop.  That is, you'll want to ensure that your communications with the boss consist of your message/question, their response, and your confirmation of the response.  Or the other way around–you respond to their question and insist on a confirmation.  Always remember that communication feedback is a three step process.

What's the problem?
Knowing your boss's problems and/or pressure points can make a big difference in both how you approach the boss and how they perceive you.  When you can empathize with the boss's plight, you're in a better position to make their worklife easier, since you'll be in a better position to know what kind of support they need and how best to deliver it.  Is your boss frantically cobbling together spreadsheets for an upcoming meeting and letting the office Kleenex supply fall below acceptable levels?  Step up, offer your services, and tell the boss you have a plan for Kleenex acquisition.  When you do this, however, take particular care to not simply give the boss a 'heads up' that the office is out of Kleenex, but to provide the solution as well. Ideally, it's a three-part email message, or verbal pitch: 

  1. First, define the problem: Out of Kleenex. 
  2. Second, provide a brief analysis of the situation: the office supply coordinator is temporarily overextended and should receive relief, which this memo proposes.
  3. Third, pitch the solution: detail how you can provide needed relief for the boss–note that you know the appropriate account numbers for ordering Kleenex, that you know the vendor contact info and that you know how and where to receive the shipment.

If you can discern your boss's problems, and plug the gaps for them in this manner, you'll have given them a gift beyond understanding. They may not even realize what you've done, but you'll realize the fruits of your labor through improved relations with the boss.

5 Responsibilities
The right-side box on the slide lists the five responsibilities of any given manager.  There's a good reason for remembering these, and that's to help keep your boss on track.  Lots of bosses are easily sidetracked into micromanaging or under-managing and by keeping these responsibilities in mind, you'll be better tuned into their problems and pressures, as well as better tuned in to what you are expecting to recieve from the boss.  So here are the five, with brief descriptions…

Meet the needs of the organization and employees
If ever there was a recipe for stress and discontent, this is it.  The needs of the organization aren't usually neatly lined up with your needs.  In fact, they're frequently mutually exlusive.  And your boss sits there, in between you and the organization, trying to serve both (if you're lucky–if you're like most folks, your boss is only focused on serving the organization, since if it was the other way around, they'd be fired).  Understanding this single responsibility of managers may be enough to get you thinking about aligning yourself with an organization that truly acts on the values it espouses, and holds it's managers accountable to those values.  Such organizations exist, though they're far from the norm.  If you are fortunate enough to already be working at such an organization, then this managerial responsibility is probably nearly transparent to you.  And your boss probably is tuned into this responsibility, and has the organizational support to back them up when they (surprise!) put your needs ahead of the organization.

Ensure problems are solved
This is a no-brainer, right?  Maybe.  Here's the problem with this responsibility: a lot of managers accept that problem-solving is part of their responsibility, but they ignore the altitude at which they ought to be operating.  Many managers, especially those that have "risen up the ranks," tend to problem solve at the task level, instead of at the process level.  The reason is because the task-level is so familiar. It's an easy challenge, since oftentimes these managers have attained their current positions because of their ability to problem-solve at the task level.  So it's a comfortable place for them to hang out.  But it's an inappropriate place.  Managers ought to be pulling back and problem solving at a process level.  When you know this, you can recognize when the boss has wandered away from their neighborhood and you can gently guide them home.  It's perfectly fine for the boss to throw a few tips your way–that's the benefit of experience.  But ultimately, your tasks belong to you.

Ensure expectations are clear
Why is this so hard for managers?  As you'll see in part 4, the fault for unclear expectations may not lie entirely with the boss (hint, hint).  You can do your part to help extract the information you need.  Earlier I mentioned the three-step communication feedback model.  This is pretty much where it becomes critical, and where you can help the boss stay off your back.  If your boss is prone to under-manage, then force the three-step communication feedback.  It works in one of two ways: you initiate, or the boss initiates.  If you initiate, then you'll expect a confirmation from the boss regarding what you said (your message).  Once that confirmation is received, you affirm receipt of the confirmation.  Now you've sent the message and you know the boss understood it, and the boss knows you know.  If the boss initiates the message, then be sure to give them the confirmation that you heard it, as well as any questions (now you're initiating a message again) you have about their message.  Be sure to get that final confirmation of understanding from the boss.  Basically, in order to manage the boss with respect to expectations, you've got to drive the communication process.

Provide feedback
This is a similar sort of "feedback" from the feedback implicit in the three-step communication feedback model.  This kind of feedback takes place at a higher "altitude," though, than personal communcation strategies.  Good managers are in regular communication with their team regarding progress being made toward any current goals or deliverables.  This really goes hand-in-glove with the clear expectations responsibility, discussed earlier.  If the team feels like they're floating–not really knowing whether they're doing good work, or even the right work, then the team isn't receiving sufficient feedback, or feedback of a high enough quality.  If the manager can't perform this responsibility, then you can drive the process by hooking back into the three-step communication feeback model. 

Manage process
This is the final responsibility and is a frequent stumbling block for many managers–especially those who have risen up the ranks due to their skill at managing tasks.  The temptation to drop back to task-management can be very strong, because process management is difficult, abstract, and frustrating.  Task management, in comparison, can be difficult and frustrating, but it's rarely abstract.  There's really not a good reason, organizationally speaking, for a manager to work at a task level.  There are plenty of justifications for it, though.  Most common among these is an inadequate staffing level due to budget crunches.  The manager may feel that they need to take on task-level responsibilities because they can't ask you to do any more, since you're already overburdened.  This is a roadmap for disaster.  When the manager is focusing at a task-level, they aren't focused on the process-level, and management suffers because of it.  What can you do?  Same stuff we've already covered.  Namely, knowing what the manager's problems and pressure points are and working to fill gaps when you can; being committed to clear communcation regarding responsibilities; being dependable; understanding where the organization or department is going, and how your tasks are the breadcrumbs along the path.

The Secret Art of Managing Your Boss, part 4

So here we are: the final installment of 'The Secret Art of Managing Your Boss.' I hope the previous three posts were helpful ( part 1, part 2, part 3). The previous two "things" (Know Yourself; Know Your Boss) kind of talked around the actual relationship with the boss. Now, in part 4, we can address it directly. I'm leaving the slide graphic out of this post, since it doesn't really add anything—there were only four bullet points and they're listed below.

Context and Content
When communicating with the boss (or anyone), there are two things to keep in mind as you consider what's taking place (remember double loop learning?): context and content. Content is the actual message that is being communicated—thoughts and ideas. Context consists of the situations, feelings and environments that surround the content. Most folks only think about the content of the message without explicitly acknowledging the power of context, even though they are impacted by it. You're wise to pay attention to both elements. Context, like perception, is a shifty devil. Situations and environments change in the blink of an eye, and what was once unthinkable, becomes standard operating procedure.

Problem Clarity
Irrespective of what type of boss you've got—a reader or a listener—you've got to be able to not only identify problems, but also to identify solutions, and other variables that impact the situation. The best way to do this is to pitch a proposal. And the best way to pitch a proposal is to adopt the classic three-part memo. Here's a template for your use—it's in Microsoft Word and you can just file it away and reuse it as needed. The basic idea, though, is to break apart the pieces of the message. There should be a block of text that describes the problem, a block of text that does a brief analysis of the problem, and a block of text that details the proposed solution. Each should build upon the other, in order to make a bombproof case for change. This way of organizing information is called "chunking" and "info-mapping." Tech writers excel at this kind of stuff.  Learn more at (no affiliation, I just admire their methods).

Goodwill Account
The goodwill account isn't anything you can quantify or put your finger on, but it's something to be aware of. Pretty much everyone keeps track to some degree of who's done what for them. Those who have done something for me have a balance in my goodwill account. Those who haven't, don't. It's much easier to say no to someone who doesn't have a balance. The '7 Habits of Highly Effective People' book has a specific name for what I'm calling a 'Goodwill Account,' but I just can't remember it. Actually, I can't remember much from that book, aside from 'Sharpen The Saw.' What's that tell you? Being aware of both your balance in your goodwill account with your boss, and being aware of how you treat your boss due to their balance, is a good exercise. It's nothing that needs to be addressed explicitly (someone in a seminar asked me if they should keep a spreadsheet of the goodwill account—not a good idea), but you ought to check in and see how the account is informing your interactions with your boss.

Here we are again, with our old friend Mr. Feedback. By now you ought to have a good grasp of feedback at both the task and process levels and how you can use feedback to keep your boss accountable. In my estimation, the two largest leverage points for managing your boss are continuing to seek to understand your own self, and becoming an expert at appropriate feedback interactions. Use appropriate feedback to help your boss help you.

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