Dear Dr. Dorothy: Lessons on How to Stop Making Stupid Mistakes at Work

Advice for the ambitious yet confused employee

Pressures at work grow more intense with each passing day, you are stressed and stretched beyond endurable intensity, uncertainty looms at every juncture, your company is doing more outsourcing and threatening your very livelihood. How do you keep up, much less succeed in this new dogged environment? Dr. Dorothy will help you.
The business world has lost its equilibrium, fellow managers. Where once there were quaint “25 Years of Service” ceremonies, complete with a gold (or gold-plated) watch, and General Motors, with good pay, generous benefits and lifetime employment, now we have outsourcing and an abundance of low-wage high-turnover service jobs. Back in what now seems like the ancient dark ages, there were corporate bailouts (please do not infer that Dr. Dorothy wishes to resume this unenlightened and dubious practice), in case some overly ambitious executives took their greed too seriously and risked the hard-working employees’ pension plans. Now we have corporate meltdowns such as Enron or Health South (the list, dear readers, is much much longer, but Dr. Dorothy will not bore you with the horrid details), where thousands of downtrodden and trusting souls have lost their children’s inheritances. And we have hedge fund managers who complain bitterly about having to pay the same income tax rate is the average worker. Indeed! What injustice these heady hedge-funders must feel, being judged by their professional inferiors, these congresspeople and, god forbid!, common voters.
How must the competent, earnest and diligent manager cope with the unforeseen tests and difficulties inherent in this age of globalization? Dr. Dorothy always thought the earth was round, and she had much scientific evidence to justify her assumptions. Now, dear friends, she is told the earth is flat. So she appreciates the stress which you conscientious managers face every day. Honestly, how can you achieve stellar results when some unknown persons are forever moving your cheese, stealing your fish, or hiking into deep valleys where packs of female wolves rove and devour unsuspecting neophyte trainees in one minute?
Into this unpredictable and ever-changing world where WIRED used to have something to do with 25-amp fuse boxes and where My Space usually meant one’s own comfy bedroom, or perchance it indicated a propensity against the marital state, Dr. Dorothy ventures cautiously, dispensing her advice to hapless individuals, these managers overwhelmed with the ever-looming trends, shocked by the future, and gasping for the secret, for the seven habits that will lead them to penultimate success and inner unperturbed bliss.
These thorny tidbits of advice are for the high-performance challenged manager, for the treasured supervisor who dreams vainly of charts and graphs with forever upward lines, but is unreasonably saddled with middling results.
If the patient readers care to go further, you will be rewarded with tart desserts in the form of question and answer. Surely, careful readers, you will see familiar problems, some of which you no doubt fashioned adequately and others left you scratching your heads. Dr. Dorothy encourages you to read the following to either a) resolve your unresolved issues; or 2) to learn how to tackle some thorny issues that don’t seem to go away on their own.

Being a Manager is not as Easy as You Think
Dear Dr. Dorothy,

I got promoted last year to a management position and my employees are driving me nuts! They won’t do what I ask, miss deadlines and make so many mistakes I can hardly believe they get a paycheck from the company. I end up having to re-do their work for them. If I don’t my bosses will get on my case, and I might get fired. But I don’t have time to do their work and mine, nor do I have time to keep explaining to them how to do their work. They are grownups, aren’t they? Why is it so hard to find good help?

Tired of Yelling

Dear Tired,

Dr. Dorothy thinks you need to take some deep breaths and repeat to yourself, “I will learn to delegate, I will learn to delegate.” You have the classic new manager delgatitis condition. You think you can do the work so much better and you constantly get frustrated when employees prove that is true. If these people are that awful, maybe they should get fired. On the other hand, Dr. Dorothy wonders how you got promoted with such a negative attitude towards others. After all, management is getting work done through OTHERS. If you were meant to do it alone, you wouldn’t have subordinates. Get a grip and try some new behaviors. Talk to your subordinates—in a CALM voice—and ask them how you can help them get their work done. Dr. Dorothy thinks they will tell you to back off, that your hovering makes them nervous and less productive. Plus when you do their work for them, it is demoralizing. Help them get some meaning in their work rather than you demeaning them.

Dear Dr. Dorothy,

I never knew management would be so difficult. It looked so easy before I got promoted. Now I see the hard work and daily grind that goes into it. My big problem is that I have a bunch of employees who think they know better than me. How can they, when they don’t have all the information. And someone is always coming in to my office to tell me how we could have done something better. Really, now do I get them to mind their own business?

Seiged in Sacramento

Dear Seiged,

Really, to you! Dr. Dorothy feels she must remind you that giving feedback is your subordinates’ business, especially when it involves projects they’ve been working on. You need to focus on excellence rather than your own ego enhancement. Results will be that much better with more input from the group.
And what, pray tell, is going on, Dr. Dorothy wonders, that your employees are so in the dark, that they have so little information. Shame on you for keeping the knowledge to yourself! No wonder they are in your office so often. They want to know what is going on. Here is Dr. Dorothy’s advice: 1) Hold weekly meetings where you talk AND you listen; b) At these meetings, share information with them, even more than you think they need, because your tendency is to withhold; c) Sincerely ask for their input and feedback; and d) This is VERY IMPORTANT, do not get defensive; listen and accept the feedback graciously; do not go back to your office and complain about what they said, either to yourself or someone else; learn to appreciate their input. Dr. Dorothy assures you if you do these things, you will likely have better results and less stress.

Be Nice and Share
Dear Dr. Dorothy,

I share an office cubicle with Matthew, who leaves his stuff lying all over the place, sometimes on my floor space and even my desk. His stale coffee is awful to smell and I don’t like looking at his moldy donuts. It’s hard to work in this mess! Matthew hates it when I ask him to clean up, and he quotes the company trainer from our orientation program, who talked about the need for flexibility and creativity in our workplace. Am I inflexible? What should I do?
Irritated in Tallahassee

Dear Irritated,
It’s hard for Dr. Dorothy to tell from your letter if you are inflexible in life, but in this case it’s more a matter of calling a slob a slob. The requirement for companies to practice flexibility and creativity do not include allowing a workspace to become a pig’s place. You have every right to expect a minimum level of neatness in your work area, though Dr. Dorothy must caution you to do some self-reflection and determine whether you are compulsively organized. Though difficult to face, if you are a bit neurotic, then lighten up! If you determine you are relatively normal (though who is, really, these days?), then go to Matthew and try to negotiate a “Officemate Contract” that would include not only a minimum level of tidiness, but also such things as how loud to talk on the phone, looking at things on the other’s desk, taking messages, etc. You may need a trusted third-party facilitator from HR, so neither of you starts hurling obscenities. In the event Matthew refuses to discuss such a contract, or your negotiations create more calamity than clarity, you should then ask to be transferred to a different, and hopefully more work-enducing, cubicle. Next time, plan ahead and collaborate on the contract before you start sharing office space. Better yet, Dr. Dorothy recommends that you work very hard so that one day you will have your own office and will no longer be stuck in a cubicle.

If You Can’t Take the Heat

Dear Dr. Dorothy,

I’ve been working in a high-tech firm for several years and am a new supervisor. The work is great, pay is decent and my co-workers are cool. The only problem is nothing stays the same. I thought it was bad before, but it’s even worse as a supervisor. Really, I just get adjusted to a new team, a new cubicle and WHAM! Everything gets changed. It’s like we play musical offices every few months. And now, I’m the one who has to make office assignments, or tell people their work is completely different, or maybe that they just got laid off. My head is dizzy from all these moves and new work assignments. Will it get better?

Whiplashed in Santa Cruz

Dear Whiplashed,

Has no one bothered to tell you we live in an every-changing world? And need Dr. Dorothy remind you that high-tech is the changiest of them all? Really, if you want work stability, try civil service, though even that is less constant than it used to be. In order for high tech companies to stay in business and beat the competition, they have to hustle and flow, which means employees have to constantly learn, adjust, modify and alter. You say it’s worse as a supervisor. Well, I’m sure your mother told you, “If you can’t take the heat, get out of the kitchen.” Dr. Dorothy agrees with your mother. If you can’t take the stress of management, go back to taking orders rather than giving them.

It’s not Fair!

Dear Dr. Dorothy,

The other supervisors and myself go out to lunch together every week or so. It’s time well spent, because we not only resolve some work issues, but it gives us time to bond. Because I am the newest one, I am still trying to figure out how everything works and what the norms are. The first time we went, they decided to go to a rather expensive restaurant, so I only ordered a cup of soup. I am still paying off student loans, so I have to watch every penny. Everyone else was ordering the most expensive items on the list, including $45 glasses of wine. When I saw what they were ordering, I couldn’t imagine spending that much on one meal. Then the waiter came and asked if we wanted separate checks. Being the newest one, I did what I learned and observed others. Imagine my surprise then the ones who had ordered the priciest selections called out, “One check please, we’ll just split it evenly.” At the next outing, I ordered like everyone else, only this time they asked for separate checks. I’ve figured out they mostly (though not always) do the shared costs when two particular people are there, and when we eat at expensive places. It’s really important that I go to these lunches, but I can’t afford those high-flying days, and it’s nerve-wracking not to know which is which. What should I do?

Broke in Tacumseh


Dear Broke,

You are on the horns of a Dillweed. It wouldn’t be so bad if you could predict which type of payment was coming which day, but this group has too many loose canteloupes. You are on the wrong end of equity theory here, as there is little fairness in how the payment system operates. If you were all equals--which in theory you are, as managers of similar rank, but as the newest person, you are still no doubt low on the totem-pole—Dr. Dorothy would recommend you bring it up to the group. In this case, though, what would happen is the higher-ranking (socially, though Dr. Dorothy believes they must really be low in class), free-spending loose cannons would dominate the conversation, eloquently explaining why their method is more sensible (even if it really makes not sense at all). Therefore, you should go to one person whom you trust, who likes and respects you, and who is respected by this group, and you should calmly and matter-of-factly share your concerns. Dr. Dorothy cautions you not to get overheated during this explanation. Then ask the trusted colleague for advice and, if it feels appropriate, you could ask this person to bring the topic up with some of the others, people you don’t feel as close to, while you talk to the ones you are comfortable with. Because this non-equitable practice has been going on for a while, and because your group has what Dr. Dorothy thinks are bullies in sheep’s clothing, this is definitely not a topic to bring up in the entire group. That is, until you do your networking. Remember decision-making theory. This is not a G2 decision. But Dr. Dorothy speaks with confidence that this is a gee-whiz situation.


Dear Dr. Dorothy,

I work in a graphics-design house and recently got promoted to management in a different department. My colleagues are cool and my boss is great, except about one thing. In the two evaluations I’ve had, he rates me as “above average,” even though I work my butt off and spend extra hours getting all the work done. He doesn’t seem to notice. Joshua, one of my fellow-managers, though, goes fishing with the boss every weekend, often when I’m in the office making sure the projects are all managed well. As far as I can tell, Joshua does no better than me in the work, but he sure does better on schmoozing, so he gets “superior” ratings from the boss. I’d like to spend time with the boss outside of work, too, but I am female and he is married and I think that might look suspect. What should I do?

Fishless in Wyoming

Dear Fishless,

Dr. Dorothy has no way of objectively knowing whether your work is equal to Joshua’s or not. You merely believing this to be the case is not sufficient evidence. Perhaps your work IS better than his, perhaps not. Your work could be actually inferior, too. Why are you spending so many more hours than Joshua? Are you less efficient in your work? Dr. Dorothy wonders if you spend too much time complaining to colleagues about your unfair treatment, rather than doing your work. Let’s assume for now your work is as good as Joshua’s, except for one vital area: You are not as good of a networker. And need Dr. Dorothy remind you how important it is for managers to create positive networks? Shame on you for forgetting this vital principle. Because Joshua has done better in managing his relationships with the boss, Dr. Dorothy believes Joshua is being evaluated according to the Halo Effect, which means his work is seen in a more positive light. You need to develop a more positive relationship with the boss, too, despite your fears surrounding his marital status. There are more ways to interact with the boss than throwing anglers into the lake. Offer to take the boss out to lunch, or to a business breakfast. Invite he and his wife to your place for a dinner party. Send birthday cards to his kids. But don’t stop with the boss. Start networking with other colleagues, otherwise Dr. Dorothy fears you will be complaining about a similar situation in five years.

When the Tough Get Going

Dear Dr. Dorothy,

As a new manager, I am learning a lot. One thing is that there are different kinds of people. All of my subordinates have been in their jobs longer than I have and their behaviors, well, let’s just say sometimes I feel like I am back in junior high school. Two people in particular trouble me. They are very controlling and are not nice to people who march to a different drummer, as they say. Sometimes I think they are bullies, and I’ve seen them really be mean to co-workers who disagree with their ideas. It really hurts the morale of the group, because lots of people are plain afraid of them. What should I do?

Walking on eggshells in Washington

Dear Walking;

Dr. Dorothy thinks you might be leaving out one important fact: that YOU are afraid of these two bullies. Otherwise you would have already taken care of the problem and not be asking for advice. These two sound are classic High Mach types, whose currency is power and who wield it ruthlessly. They operate best in loosely structured environments, where they get little, if any, consequence for their damaging behaviors. Clearly, your predecessor was not into consequences. Your job as boss is to make them feel some effects to their negative interactions. If they keep getting away with it, they’ll keep doing it, and the morale will continue to plummet. High Machs usually need loosely-structured systems to operate, so get some controls in place. Dr. Dorothy urges you to take control of the environment, because if you don’t, they will.

Power and How to Get it

Dear Dr. Dorothy,

My boss sent me to a “Leadership for New Managers” training program. It was fun to travel and stay in a nice hotel, and the program was interesting. But some things I’m having trouble implementing. The instructor told us we should get as much power as we can and he gave us some strategies. One of them is about making people wait for you, to show how important you are. Another is to take up more space at the lunch table, or to sit at the head of the table in the conference room, and to talk more than anyone else, to try and be the center of attention. Maybe I am not leader-material, because I just can’t see myself doing these things. Should I quit my job?

Wondering-if-I-have-it in Walla Walla

Dear Wondering,

Dr. Dorothy thinks rather than quit your job, you should dust off some of the management books you read in college, anything that might have talked about how power is more than domination, and how sustainable power means you respect other people, while you are busy networking and developing power through social relationships. The ideas you were taught fit more into a 1980’s seminar, and author Wayne Dyer would be proud. But Dr. Dorothy thinks the person who should quit the job is that instructor. This is the new millennium, after all, and you need to put your energies into collaboration (creating allies) and continuous learning, creating situations for reciprocity, becoming more likable, becoming better at asking for what you want, and increasing your expert and referent powers, not measuring how much real estate you are taking up in the restaurant.

The Other Teams Could Make Trouble for Us if they Win--Yogi Berra

Dear Dr. Dorothy,

After I got promoted two months ago to a management position, I’ve scheduled weekly meetings with our group, so we can go over what we accomplished during the past week and what our goals are for next week. Sometimes the meetings go over time, but it’s REALLY IMPORTANT for everyone to participate and get their ideas out. Many meetings are actually quite exciting, with lots of new ideas being proposed and brainstormed. The problem is one of my employees who keeps complaining that the meetings are “not focused” and they get “too touchy-feely.” He says there are no action items and no follow-through at the next meeting. I definitely DO NOT agree. How can you have a good team if you don’t pay attention to people’s ideas and also their feelings? People NEED to be HEARD and APPRECIATED. How do I make this guy see we can’t just have FACTS ONLY meetings?

Team-Builder in Toronto


Dear Builder,

Dr. Dorothy can see you have yourself convinced of the rightness of your actions. But beware the self-righteous outlook! Your troublesome employee may actually be your godsend (isn’t that often the case that your calamity is your providence?) and help you to see the error of your ways. Ah, you are shocked that Dr. Dorothy would suggest such a preposterous notion? Consider that your idea of total participation, with lots of brainstorming and being focused on listening to all and appreciating everyone could, in fact, lead to chaos. The fact that your employee does not see action items or follow-through concerns Dr. Dorothy. Yes, she agrees, you do need to consider people’s emotional needs, but without follow-up, your meetings are little more than verbal partying. Lots of fun, but no work accomplished. So Dr. Dorothy asks you to listen to this employee, just as you do to others in the meetings. Listen without defensiveness. Then follow his suggestions. Also, and this Dr. Dorothy tells you from the bottom of her heart, please try writing without an obsession to capitalize.

Dear Dr. Dorothy

I am the new restaurant manager in a hotel/convention center. We have a fabulous and highly-rated facility and I aim to keep it that way. The reason I am writing is that my direct reports, all supervisors, can’t seem to get it right, no matter how many meetings we have going over all their mistakes. The restaurant sometimes takes 90 minutes to bring a meal to the table, room service sends the wrong food, and meeting-refreshment orders get confused. My boss has told me to come down hard on them and I have, and he’s very proud of how strong I’ve become. But in one of our daily meetings, they just weren’t being responsive to the continuing problems of getting the work done adequately. So I told them right there they had to work six-day weeks until they start to do their jobs right. All they did was balk at this command, even though I told them not showing up on Saturday would be the same as resigning. I just don’t get how they can be so good on some days and so awful on the others. Should I fire them all and start over?

Wit’s End in Wichita

Dear Wit,

Who assigned you to be the Punitive Parent to your employees? Oh, Dr. Dorothy forgot: your boss. The two of you are colluding and creating a hostile work environment, though Dr. Dorothy sees clearly that you two feel like the victims here. Does Dr. Dorothy have to remind you about the terrible teachers you had in high school, who humiliated you in front of the class, and how discombobulated you became, making it more difficult to get your work done? Your job is not to humiliate, but to solve the problems at hand. It does not help the situation that your boss seems to be the reincarnation of Machiavelli. Here are some ideas from Dr. Dorothy: During the next meeting ask questions, find out what is going on, where the breakdowns occur. Ask your people what they would do to design a better system. You are too quick to admonish. Dr. Dorothy suggests that good managers rarely need to raise their voices to a higher decibel. Here is her formula, which you should memorize: More questions equals less yelling. Now if Dr. Dorothy could only get your boss to learn this, too.