Chapter 22
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 Who’s the Boss Around Here?


In This Chapter
  • Being assertive with your boss
  • Smile when you say that
  • Give-and-take often extends beyond the lines of authority
  • Showing the boss how much more you can absorb
  • Working together for higher productivity
  • Influencing your boss for his or her own good


“Of all the gin joints in all the world she has to walk into mine. You played it for her, you can play it for me. If she can take it, I can take it. Go ahead Sam, play it!”

—Humphrey Bogart, as Mr. Rick, in Casablanca

“Of all the people in the world that you may be least inclined to be assertive with, your boss is at the top or near the top of the list. If you can be assertive with others, you can be assertive with your boss. If your boss can be assertive with you, you certainly can be assertive back. Go ahead Sam, or Samantha, be assertive!”

—Jeff Davidson, as author, in The Complete Idiot’s Guide to Assertiveness

In recent years there have been all kinds of books with titles such as Never Work for a Jerk, How to Manage Your Boss, and Influencing Others When You Are Not in Charge. The underlying theme, I suppose, because I didn’t read any of them, is that in any boss-employee situation there is give-and-take that often extends beyond what the employee might surmise. In other words, you have more leverage when it comes to working with your boss than you might presume.

The chief way to wield this leverage is by being assertive. Obviously, there are some things you wouldn’t dare try with your boss that you can get away with when dealing with others. In this chapter, I’ll explore how being assertive can help you to enjoy all the potential bennies!

Okay, Rehearse Your Lines

You hear about it all the time. Someone has to go in and talk to the boss, and they fret for days before the big event. They practice in the mirror, talk to their spouse, even talk in their sleep. Clearly, for many of us, talking to the boss can be an anxiety-laden event.

Understandably, a range of anxieties and concerns can bubble to the surface when it comes to having to be assertive with your boss. After all, he or she has authority and leverage over you that other people simply don’t have. For example, your boss may:


  • Have the power to fire you, and fire you on a moment’s notice without even consulting anyone else.
  • Conduct performance appraisals of you that dramatically impact your ability to advance in the company, or conversely, keep you stagnant.
  • Define your job responsibilities. Indeed, he may have personally written your job description, or perhaps he used to do your job.
  • Schedule your work activities. In this respect, your boss may have control over each and every hour that you spend at work, what you work on, how quickly you have to work, and what resources you’re provided.
  • Have leverage over what benefits you receive.

As if this weren’t enough, in addition to the authorized power that your boss is likely to have over you, he may also have other forms of power, including the following:


  • She may be older, wiser, and likely to be earning more. Depending on your interpersonal dynamics, that could mean you’re intimidated by your boss.
  • Your boss could be physically imposing.
  • Your boss might have connections throughout your organization or profession or industry that you don’t have and are not likely to acquire.
  • Your boss may have a working style that is radically different from yours.
  • Your boss may have a style of interpersonal communication that results in anxiety and frustration for you.
  • Your boss may have vastly different expectations from your own as to why you were hired, what you’re supposed to do, and how you’re supposed to perform.

These factors and many others add up to the likelihood that on occasion, if not often, you’ll have some difficulty in asserting yourself with your boss! Despite all of the advantages your boss seems to enjoy, you have some leverage too. As such, you may want to do some exercises in preparation for the times when you’ll wish to assert yourself.

First, Know Thyself

Please get a blank piece of paper and a pen. On the top page, write “Outstanding Attributes.” Now, list everything you can think of about yourself that is outstanding, particularly your innate skills and attributes. For example, your list might include wit, charm, stamina, endurance, tolerance, and affability.

You might add phrases such as “keen powers of concentration,” “the ability to set priorities,” or “the ability to meet deadlines.” The list you generate should contain at least 15 or 20 items. Many people can reach 30, 40, or more. If you can’t think of that many, refer to Chapters 5–8 on self-confidence for ideas.

Professional Skills

When you’ve finished with this list, write another heading, “Specific Skills.” Now list every blessed thing that you’ve learned professionally over the past several years. For example, do you know how to use Microsoft Word 9.0? List that. If you know how to use Internet search engines, include that as well. Run through all the software that you know how to use, office equipment that you can operate, and office procedures that you are knowledgeable about.

Then list any other professional skills that you have, such as mastery of a foreign language, the ability to use other equipment, and so on. This list may exceed 30 items and if it’s double or more, all the better!

Who Can I Turn To?

Finally, under the heading “People,” make a list of the empowering people in your life—those people who have an effect on your professional and personal life. This should include everyone you can get on the phone and share information with at the touch of the keypad. It also includes any mentors that you have, coaches, advisors, team members, or helpers of any nature.

This list, too, may reach 30 people or more. If you’ve been in the working world for a while and have been fairly active in your industry or profession, your list could exceed 100 people. You have my permission, however, to stop at about 50 or 60 names.

If you find it hard to list 30 people, set a lower goal, such as 10 or 15.

Go Away, Come Back Another Day

When you’ve completed all three lists, put the page away, and take it out another day to review it. This list serves as a reminder of who you are, what you can do, and who you know. Think of it as a resource tool, a confidence booster if you find yourself being less assertive than you’d like when confronting your boss.

Recalling the words of Dr. Janet G. Elsea in Chapter 13, you cannot not communicate. In other words, every time you speak to your boss, regardless of the actual words and phrases that you use, you’re communicating. If you’ve recently reviewed your resource list as well as Chapters 5–8 on self-confidence, your sense of self-confidence and assurance will come through to your boss the next time you’re in conversation.

Bricks and Mortar

In addition to preparing a resource list, you should begin laying the groundwork now in conversations with your boss. This will come in handy later, for those times when you seek to assert yourself. Here are a variety of tips for doing so:


  • Praise your boss when he merits praise. Many employees forget that the boss is a person, too, who needs psychological strokes just like everyone else.
  • Assemble your evidence. If you have a point to make, come in armed with supporting evidence.
  • Do some pencil pushing. If it’s not clear whether the department is going to pick Plan A or Plan B, map out the costs and benefits as you see them and present them accordingly.
  • Don’t dump on your boss. Your boss is not a shoulder to cry on for what went wrong at home or at work. Yes, depending on your relationship, you certainly can seek empathy from him on occasion. He may be the type with whom you can commiserate. Generally, though, keep your lamentations brief and move on to what’s next. Keep thinking solutions.
  • Use “we” and “us” phrasing instead of “I” and “my.” Think, speak, and convey “team.”
  • Pace your communications. Don’t overwhelm your boss with more than she can comfortably take on at one time.
  • Take personal responsibility for any department-wide activities or projects in which you’re participating. Take responsibility when things go wrong as well. Nothing lays the groundwork faster and more effectively for you to be assertive than when you have a reputation for taking full responsibility for your actions.
  • Don’t drone on. Present your situation or problem as succinctly as you can.

By engaging in these behaviors, you’ll find that often you have more latitude later, when you may need to assert yourself.

Emulate Your Boss’s Communication Pattern

Martha Peak, group editor at American Management Association Magazines division, said in an editorial in Management Review (February 1995): “Correctly sizing up your boss’s communications preferences may mean the difference between getting your project off the ground or watching it fall moribund before it gets a fair chance of survival.”

“The most effective style is not one that follows some preferred textbook approach,” says Peak, “but rather, one that the listener is most attuned to.” Thus, if your boss prefers that you sit down and chat for a few minutes, get good at doing that. If he prefers that you stand by the door and give a quick report, so be it.

The Good, the Bad, and the Beheaded

Convey the good and the bad as it transpires. If you have to deliver bad news, however, it’s best to have a strategy already mapped out.

Too many employees are afraid of falling prey to the Persian Messenger Syndrome. As the story goes, in ancient times, whoever brought bad news to the king was beheaded. Soon enough, no one brought bad news to the king.

The great paradox of this situation is that to be an effective king, or a boss for that matter, one has to have accurate information about what’s happening in the kingdom, or in the department. If your boss is only being fed good news or a sugar-coated version of what’s happening, he’s likely to fail as a leader.

If you’re the one staff person who can deliver bad news without blinking and also have some ideas or solutions to impart, you’ll have far less trouble when you need to assert yourself in major ways, like asking for a raise.

So, what strategies can you employ for delivering bad news? Try following this plan:

  1. Start with some good news.
  2. Give the bad news, and follow it with some possible solutions.
  3. End with some other good news.

Going for the Big One, Asking for a Raise

Earlier I asked you to develop a resource list that contained a roster of your attributes, acquired skills, and human resources. Concocting that three-part list undoubtedly took a few minutes, but if you did it (did you do it?) and review it often, it’s likely you will experience the benefits.

Now, I’m asking you to create another list, and this one is going to take a while. I call it your “Internal Achievements List.” It is a clear, detailed, and accurate list of what you’ve done for your team, department, or division in the past six months, year, or two years.

Here are some examples to get you started:

January—Received credit as one of eight associates contributing to the annual report.

January—Appointed by team as chair for the first-quarter meetings.

February—Completed second appearance before industry council representing the organization’s philosophical viewpoint.

March—Participated in the reorganization of the department library.

Armed with such a list, you will be your most effective self when asking for greater rewards due to your contributions and value to the organization. Memorize these before sitting down with your boss. You can also type them up concisely so that you can position a single piece of paper on your lap and look down to see an instant reminder of all you’ve accomplished.

Here are some examples of assertive language that you can use, having discussed your various contributions to the organization:

  • “In light of what I’ve presented, I think that my request is fair and certainly merits consideration. Can we get back together on this at this time next week?” (Use this approach with a boss who is highly organized and detail-oriented.)
  • “I’ve stated my case clearly. I’m trusting that you’ll do what’s best for you, me, and the organization. I believe I’ve earned this; now it’s a matter of making it a reality.” (Use this approach with a boss who is very loyal to the organization, perhaps having been employed there for 10 years or more.)
  • “I appreciate your listening to me. I know you’ve got lots of important issues to deal with, but understandably, this is an extremely important issue to me. Can we wrap this up in the next couple of days?” (Use this approach with a boss who maintains a clear desk—someone who doesn’t let issues accumulate.)
  • “Hey, I know I’m asking for something significant, but I also believe that I’m more than worth it. Besides, once I get this, I won’t come in here with this issue for at least another three months [said jokingly].” (Use this approach with a boss who appreciates a sense of humor.)
  • “There it is, all laid out on the table. I’m trusting that my points were clear. I think my case is pretty much irrefutable. I know you’ve got a lot of other things on your mind right now. By taking care of this one quickly, [said in a light, good-natured way] you’ll be able to turn your attention back to everything else.” (Use this approach with a boss who is analytical in nature and who will probably assess your request point by point.)

Obviously, some of these statements work better with some boss’s personalities than others. Without meeting you or your boss, I can’t tell you what approach will be most effective with your boss.

Mastering the Performance Appraisal

Depending on the size and nature of your organization, you may receive an annual, semiannual, or quarterly performance appraisal. The appraisal might be tied in to a raise or be independent of it.

Some people look forward to performance appraisals—especially if they’re linked to raises. Also, for many people it’s the only time they get positive feedback from frantic, overextended bosses. Hence, a performance appraisal can be a positive experience. But for many people, this may not be true. You probably don’t enjoy performance appraisals. Your boss probably doesn’t like them either. This is why you should make the performance process far less upsetting, and, in fact, even somewhat enjoyable, by asserting yourself!

The Man with the Plan

As you would do when asking for a raise, bring along your Internal Achievements List. In addition, spend 10 or 15 minutes a few days beforehand mapping out a little strategy:


  • What issues is your boss likely to bring up? How would you respond?
  • What didn’t you do so well that might be a topic of discussion? How would you skillfully address shortcomings and offer solutions that minimize or eradicate them in the coming period?
  • What if your boss says something you think is inaccurate? How would you respond? How will you maintain your level of composure?

Mentally rehearse what you’ll say in each instance, so that you’ll feel confident and do your best when it counts—during the actual appraisal.

Equal Footing

It’s vital to remember during a performance appraisal that you’re not some waif who by the grace of God was given this job, and every now and then given a cookie and a pat on the back for your efforts. Your performance is being appraised so that you can obtain feedback, formulate strategies for improvement, and understand your role and position in the organization.

Concurrently, your boss gets your views on how you’re doing, which can be valuable information for him. He also gets the opportunity to learn more about his effectiveness as a boss, and the opportunity, potentially, to reward you.

All of this points to the notion that you want to engage in this discussion as someone on an even plane, almost an equal partner to the performance appraiser.

If performance appraisals are a time of high anxiety for you, Marsha Reynolds, a personal and business coach based in Minneapolis, Minnesota, has an idea that’s an interesting variation on an earlier theme. She suggests that you make a brief roster of your strengths, such as intelligence, compassion, and creativity. Put these on a pocket-size card. Then, before you enter some potentially intimidating situation, whether it be a performance appraisal or a phone conversation, find a quiet place and actually read the card out loud, saying “I am” before each item.

By the time you get to the end of your list, Reynolds says that your sense of self will be stronger. You’ll approach the encounter feeling powerful and centered.

Taking the Reins

Here’s how to get the best from your performance appraisal, stand up for yourself if necessary, and leave the meeting feeling good about what transpired:

  • Listen as closely as you ever have listened to anyone speaking to you. Take notes. Write like a son-of-a-gun. Take down as much as you can.

    There aren’t many other times in life when you get such pointed, potent information about your capabilities and performance. (If you could tape the performance appraisal all the better, although I doubt that many performance appraisers would be comfortable having such a device present.)


  • Take responsibility for whatever did not go right on the job, when in fact it was your responsibility.
  • Remain on an even keel. Don’t get flustered or upset if you hear things that you think are inaccurate or overly critical. You’ll have your turn to speak.
  • Ask probing questions that require more than a yes or no answer. For example, rather than asking, “So, you’d like the quota to be above 10 percent?” to which your boss could respond yes or no, try asking, “What do you see as the optimal quota target and how do you arrive at that?”
  • Recap what you learned during the performance appraisal. If there are any action items that you and your boss agreed on, reiterate your willingness to initiate them.

Preempting the Appraisal Process

Why wait for an annual, semiannual, or quarterly appraisal? Get in the habit of producing your own. Yes! On a weekly, monthly, or other interim basis, provide your boss with a one-page, unsolicited appraisal of your performance. Make it as accurate and as objective as you possibly can.

At first, your boss may be a little dumbfounded that you even went to the trouble. Assuming you aren’t explicitly told to stop, by the third or fourth time you’ve done it, your boss may begin to expect it. Thereafter, he may even look forward to it.

When the formal-appraisal time rolls around, guess what? More than half the stuff that you’ve submitted makes its way back to you as part of your boss’s feedback. In other words, you get to assert yourself in a grand way. You end up influencing, if not dominating, a process you might have once feared.

When You’re Asked to Do Too Much

When you’re asked to take on too much at work, stay too many hours, or handle more than you’re comfortable handling, the ability to assert yourself is valuable indeed. Suppose you work for a boss who’s a full-fledged workaholic. How do you keep your job, turn in a good performance, maintain sufficient relations, and still have a life? You say “no” without having it sound like “no”:


  • “That is something I’d really like to tackle but I don’t think it would be in our best interest since I’m already on xyz.”
  • “I can certainly get started on it, although because of the abc deadline and the xyz event I’m certain I won’t be able to get into it full fling until the middle of next month.”
  • “If we can park that one for a while, I’m sure I can do a good job on it. As you know, I’m already handling the hij and wouldn’t want to proceed unless I could do a bang-up job. If you need to have somebody get started on this right away, I wouldn’t hesitate to suggest Tom.”
  • “I’m not sure what level priority this should be in light of the lineup I’m already facing.”

Don’t Wimp Out on Yourself

You don’t want to fall into the trap of declining every time you’re asked to take on more work, because it can have ramifications on your career health and peace of mind. Too many professionals today, fearful that they may lose their job as well as health insurance and other benefits, suffer various forms of work-related abuse because they lack the ability to assert themselves.

Here is some additional language, mildly more forceful, that you may need to draw on, depending on circumstances:


  • “I’m stretched out right now to the full extent of my resources and I’m fearful that if I take this on, not only will I not be able to give it my best effort, but the other things I’m handling will suffer as well.”
  • “I’m going to request that I not be put on assignment jkl, if that’s okay with you. I’ve been going long and hard for several months now and if I don’t regain some sense of personal balance I feel I’m putting my health at risk.”
  • “Is there anyone else right now who could take that on? I need to get a better handle on what I’ve already been assigned. In a couple weeks, or perhaps a month or two, when things calm down, I may be able to work something else into the lineup.”
  • “I wish I could—I’ve been burning the candle at both ends, and if I start to burn it in the middle there will be nothing left.”
  • “I’m honored when you ask me to take on some tough assignments, because that means you have strong confidence in me. By the same token, I think you’ll agree that I have a good idea of when it wouldn’t be prudent for me to handle another responsibility. This is one of those times.”

Asserting Yourself in Dire Situations

Suppose your boss is one tough son-of-a-gun and despite your protestations to the contrary keeps piling on the work and responsibilities. No matter how effective you are at asserting yourself and how often you do it, you seem to be besieged with more assignments, more projects.

If this is the case for you, the first thing is to stop and assess the situation. Here are the basic options:


  • You can leave your present position, department, or organization. This is radical, but sometimes it’s the best alternative.
  • You can push for a compromise situation in which you take on some of the new work. Or, you take all of it on, but you receive additional resources such as more staff people, a bigger budget, or more equipment.
  • You can knuckle under and simply take on the added assignments with no additional resources.

Since the middle option is most desirable in those situations in which your boss simply won’t stop dishing out the assignments, assert yourself for the purposes of at least making your situation easier. Here’s some language you can use if you’re willing to only take on some of what’s been assigned:


  • “I believe I can handle the stu assignment, but the rest simply has to go to the other department. I’m snowed under now and it won’t be of any value to anybody if I can’t deliver.”
  • “Of all these projects, which is the one that is most important? That’s the one I probably ought to tackle, and we need to assign the rest of these elsewhere.”
  • “I can appreciate what you must be up against. I’m already working over the max, but I would like to help you by taking on the xyz assignment.”

Using this kind of language doesn’t necessarily mean that you would be happy to handle the assignments, but that you’re doing what you can to accommodate your boss given your already demanding workload.

Get the Resources You Need

Having adequate resources to tackle what’s assigned to you can be important. You already know how to structure your requests. The only thing I have to recommend at this juncture is to prepare a memo that will help your boss understand and accept your resource requests. By putting down on paper precisely what you need and why, you give your boss the ammunition he may need to “make it so.”

For example, you could compute how many hours would be necessary to tackle the new assignment, how much that would cost in terms of bringing another staff person on board, and what the overall return would be. Proceed in a similar fashion if you need a bigger budget in general, new equipment, or other resources to be successful in handling the added assignments.

When Nothing Works

If the situation looks untenable—no level of assertiveness on your part is sufficient—you may be forced to either consider leaving the organization, getting transferred elsewhere, or taking on the extra work against your better judgment.

If you take on the extra work, do so for a finite period of time, until you can make a major job change. When you see a light at the end of the tunnel it makes whatever you have to endure in the present a little more tolerable. Your long-term health and well-being are far more important than any job situation in which they are put into jeopardy.

If you have to take on the work, but you don’t want to make a major job change, keep in mind that even crunch periods come to an end. Hang in there!

A Parting Word

John Caposy, author of Why Climb the Corporate Ladder When You Can Take the Elevator?, has some sage advice, particularly when dealing with your boss, with which I will close this chapter:


  • “Most consultants first ask corporate executives what advice they are seeking and then later give them that advice.” (Do you see any corollaries here with giving advice to your boss?)
  • “A career should be a quest not for perfection, but for a high batting average.” (I’ll bet this one applies to you all day long.)
  • “If you think something is wrong, it probably is.”
  • “Better to ask twice than to lose your way once.”

The Least You Need to Know

  • Draw up a list of who you are, what you can do, and who you know, and use it as a resource tool and confidence-booster when being assertive with your boss.
  • Before asking for a raise or listening to a performance appraisal, plan what you’re going to say and how you will respond.
  • Preempt and dominate the performance appraisal process by conducting your own appraisal and delivering the summaries to your boss.
  • If you’re asked to take on a large burden, ask for more resources.
  • Your long-term health and well-being are far more important than any job situation in which they are put into jeopardy.


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