The Workologist: Sharing Your Wisdom, Within Limits

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The Workologist: A Founder Who Can’t Let Go

I’m an interim chief executive at a $10 million-plus company with 30 employees. The founder and 100 percent owner is well past retirement age, and he’s hired a name-brand executive search firm to recruit a permanent C.E.O.; he brought me in so he could learn how to “let go” of running the business day to day.

He thinks he’s done that — but he insists on being in the office and casually talking to employees about what they are doing. This is really confusing the troops, who don’t know how to handle it. I’ve explained this to him, and he’ll pull back for a day or two — but then he falls off the wagon.

The board of advisers and I have tried to get him not to be in the office at all — or only a couple of days a week — and he just will not listen. He has a grandson who loves to play golf with him near the retirement home he owns out of state. Maybe that’s the key? My concern is that we’ll never be able to attract a top-notch C.E.O. as long as he’s meddling — and that I’ll be stuck in this assignment for a long time. ANONYMOUS, BOSTON

The fact that you used the phrase “falls off the wagon” is telling: This gentleman is addicted to running his company, and while you’ve explained to him why it’s a problem, you’re clearly going to have to double down on that strategy. It may even be time for a full-on intervention.

But first, take a moment to empathize your way into his head. Certainly, much of his identity is wrapped up in his company; he may not really be ready to walk away from this phase of his life. I’m sure that he enjoys golfing with his grandson, but it’s possible that he simply can’t envision a world in which activities like that are a primary focus, rather than a pleasurable break from what he really does.

One strategy is to prod him to go cold turkey. Persuade him to spend at least a month at that retirement house, and thus definitively out of the office. Maybe he’ll see the merits of a less business-centric lifestyle.

If he balks, or if this move fails, it’s intervention time. With the board’s support — and, preferably, its involvement — you need to do two things.

First, make clear that you’ll never get the best C.E.O. candidate to take a job that involves the owner’s peering over her shoulder all day. In the long run, that undermines the future of the company to which this founder has devoted his life. And the best thing that he can do for its future is to back off.

Second, be specific about what that means: strict limits on time in the office, specific parameters on employee interactions, a timetable for backing off the detailed updates, firm rules about a transition that will give the new C.E.O. genuine control. You can soften all this with a vision of the very good phase of life that he now deserves to enjoy.

The starker the choice, the more likely that he will either kick the boss habit or acknowledge that this is all a charade and that he can never quit. Either way, make it clear that if he won’t commit to this plan, he’s wasting his time — and yours.

•

The Road Not Taken

I have been in my current position as a writer in a global company’s marketing department for just over three years, and have assumed a leadership role. During my last two annual reviews, my boss told me that he was looking into securing a senior position for me that would entail a bigger cubicle and a raise. Most recently, he asked if I’d be willing to assume the job duties and the bigger cubicle without the official title — or the raise — because he did not yet have the budget. I declined, saying I was concerned that the official promotion would never come through.

Fast-forward a few months, and one of the other two writers in our location has been transferred out as a result of a global reorganization. The new org chart now shows an “open” position that is basically the exact senior-level job that I’ve been promised for the last two years.

I spoke to my boss about the open position — and he said I could apply for it. Am I wrong to feel slighted, or is this the way that large companies operate?

ANONYMOUS, LOS ANGELES

Yes, this is the way many large companies operate. But you’re not wrong to feel slighted. And one way or another, you should be proactive about the situation. At the very least, you should also consider your options elsewhere; in fact, you might want to make that your top priority.

But if you want to keep pursuing a job that’s been dangled before you for a couple of years, you need to get a better sense from your boss about his apparent shift from enthusiasm to neutrality. Possibly, he disapproved of your refusal to take on new responsibility without a better title and more money. Or maybe he just has less influence than the person who’s in charge of all that global reorganizing.

In either case, there’s no way to skirt your core issue. But you can try to address it in a way that stops short of a blunt “I’m entitled!” confrontation. Tell your boss that those past reviews gave you the impression that he thought you were ready for this job — is that correct, or have new concerns arisen? Is there any reason that he now believes you may not be ready for it?

You may not like the answer, and that’s why starting a parallel job search is a good idea. But in the long run, knowing will be better than wondering.

Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld for publication). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

The Workologist: A Bad Worker’s Mad Mom

Dear Workologist:

Seven months ago, I hired a 24-year-old part-time worker to replace someone who was going off to college. The job basically involves billing and database entry. Despite months of one-on-one training, this worker is a disaster. He can’t make a decision without consulting his notes on the simplest of tasks, and is thoroughly unproductive. But he is all I have until I hire someone new.

When I was away from the office recently, his mother visited and badmouthed me to one of my colleagues. She left a note for me to call her. When I did, she informed me that her son tells his parents “everything,” and that I should basically stop picking on him. Then she told me not to tell her son she had called.

I am so irate about this mama’s boy that I feel like telling him about the call — and pointing out that it is entirely inappropriate to rely on her to fight his battles. Or should I just zip it and fire him politely when I have found his replacement? Name Withheld, Connecticut

I certainly understand your irritation, which sounds perfectly justified. But I suggest thinking about how you’ll feel about this whole incident in, say, a year.

On the one hand, I’d argue that you have zero obligation to honor Mom’s demand that you observe the code of omerta. However much she may love and admire her son, there is no professional, contractual or even relevant relationship between her and you. And I concede that there’s a case to be made that in the long run you’d do this fellow a favor by pointing out that a 24-year-old shouldn’t tolerate that level of parental interference in his work life.

On the other hand, who cares? Apart from sheer emotional catharsis, what do you have to gain from drawing your employee’s humiliation into sharp relief? Even the idea of rationalizing a confrontation as some kind of tough love doesn’t make much sense. I’m guessing that you care less about your hapless worker’s professional future than you do about finding a replacement.

A year from now, Mom’s drop-by will be just an annoying — and, by then, a possibly amusing — memory, particularly if you have found an excellent new employee. That’s where you should focus your energy.

•

Dear Workologist,

I am working for a well-known Paris luxury fashion house’s Hong Kong office. Recently a human resources officer talked to me about my red bob hairstyle (think Florence Welch) which I dyed a few months ago. I had not heard from my boss or any other superiors that they regarded it as unprofessional; in fact, I have received a lot of compliments from my colleagues on it.

However, the H.R. person said she had heard a lot of discussion about my hair. I replied that my hair color is a personal matter, but she told me that it was not — it could affect the image of the firm. Then she suggested that I change it before I received any formal warnings, and even implied that I could be fired. She said that either brown or black would be appropriate.

I was surprised to hear that a fashion company could have such low tolerance for personal style decisions. Is my red hair too provocative or are my colleagues too conservative?

Lea, Hong Kong

I can’t quite see you from here, so forgive me for dodging whether I find your hair “provocative.” In any case, you need an answer to a different question.

From your description, the H.R. person has been crystal-clear: if you want to work there, you need to conform to certain rules. While it’s interesting to debate the wisdom of that attitude emanating from a fashion house, I’m fairly confident that your chances of saving your hairstyle by way of sparking a cultural shift across an international business are pretty close to zero.

By and large, dress codes remain one of the dreariest quandaries of business culture: They can make an employer seem cartoonishly oppressive, but they persist as a tool for officially addressing workers whose sartorial decisions violate what seem (to managers) like obvious office norms. Sadly, then, I think the answer you need has been made bluntly apparent: What’s more important to you, your hair color or this job?

Now, should you go black or brown and your superiors seem disappointed, you can truthfully explain why you did it — and maybe that will set off an internal debate at your company that leads to a whole new era in dress-code history. Or if that doesn’t happen, it’ll still buy you a little time to find a more fashionably enlightened workplace.

•

Dear Workologist:

I have been in an entry-level administrative job for five months. In most ways, it’s good — fair pay, great benefits, reputable company, decent learning and growth opportunities. But the truth is that I’m not really passionate about, or even interested in, the position or the field. I am already thinking about switching to another field. But I don’t want to look as if I am job-hopping, and I want to be able to demonstrate that I have gained significant skills and performed well in my current position before leaving it behind.  How long should I stay before I move on?

Sarah, Houston

Start looking immediately, and aggressively. If you’re certain that your current field is merely a way station, there’s no reason to delay. Particularly when it’s early in your career (where it seems you are now) there’s no huge penalty for realizing your calling lies elsewhere.

Do your current job as well as you can while you explore other options. You’ll stay in your employer’s good graces, and give yourself the time you need to find your proper path as best you can.

But the important point is to work on that goal right away, rather than worrying about the “optics,” as politicians say. If you put this off until your current job feels intolerable, you’ll end up making a move that’s more about getting out, as opposed to moving ahead. And there is certainly no reward for being able to declare, “I knew this field wasn’t for me, but I dispassionately fulfilled my duties for years anyway.”

Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld for publication). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

The Workologist: You Didn’t Get the Job? Maybe It’s a Good Thing

Dear Workologist:

Someone at a big company that I worked for some years ago recently approached me via e-mail, asking if I would be interested in rejoining. I was. “Fantastic,” this manager replied, and a few days later we spoke over the phone. He sounded pleased, asked me to submit my résumé online to get things rolling, and said human resources would be in touch.

I did not hear from H.R. A week later, I e-mailed the manager who had reached out — and received no response. Another two weeks went by. I called him and left a voice mail message. Late that night, I received a standard rejection e-mail. The job listing had been removed from the company Web site.

I was shocked and hurt that I had not had the courtesy of a phone call or personal e-mail from this manager. I left him another voice mail, asking what had happened and that he consider me in the future. Again: No response.

What should I have done? Does it make sense to try to contact this manager for future work? I don’t want to stalk him. Name Withheld

You certainly have every right to feel bewildered and insulted. But maybe you should also feel relieved.

It’s easy to conjecture all kinds of explanations here, but keep in mind that some of the most plausible actually have nothing to do with you. Maybe this manager lost some kind of internal political struggle about the new position. Maybe he stepped on H.R.’s toes. Maybe he didn’t know that an internal candidate had the gig locked up. Maybe the process always takes months, but no one bothered to tell you. Who knows?

But frankly, no matter what the explanation, it’s lame that he ended a conversation he started with a full-on vanishing act. That’s why your best course might be simply to be pleased you avoided working for this guy, and let the whole thing go. Plenty of companies have strict policies about avoiding communication that could open a can of litigation, but too many managers use that as an excuse to dummy up. You want to work for someone better than that.

Should you wish to resolve the mystery here — which I would understand — you could give that manager one last shot. But do so in a way that removes short-term job-seeking from the conversation. This may sound disingenuous (mostly because it is) but you could try a note that has two themes: Thanks for thinking of me, and would you consider an informal, off-the-record phone call about what went awry here? Indicate that your interest is purely for future reference, not about rehashing this incident. What you really want to do is find out whether H.R. somehow found you objectionable, and for what (possibly misguided) reason.

If the conversation is framed as carrying zero threat to this manager, maybe he’ll be helpful. And perhaps the chat will go so swimmingly that you’ll want to keep in touch about other opportunities. But based on your experience, I’m sorry to say that I think that’s a long shot.

•

Dear Workologist:

I work as an administrator for a medical practice. I earn a decent salary, but not what I think I deserve — and about $6,000 a year less than the other administrator. We are connected to an academic institution, and her salary is mostly covered by the college. But she asked the practice to add 10 percent to that figure, and she got it.

The thing is, she does nothing, basically. She has snowed the entire department and my chairman. She is lazy, not smart, makes personal calls all day long, and doesn’t even have a college education. Yet she earns more than I do.

I just can’t get past it. I am incredibly dedicated, work very hard, manage a staff, run the finances and billing for the department, work with the billing service. My question is, what do I do to make my boss realize he has been completely taken for a ride? How can I get more money? I deserve at least as much as this other administrator.

L.R.H.

Long ago, H. L. Mencken defined wealth as “any income that is at least $100 more a year than the income of one’s wife’s sister’s husband.” Decades later, people with advanced academic degrees came to a not-dissimilar conclusion about the intersection of human psychology, money, and “positional concerns,” by way of a study finding that a surprising number of people would choose to earn $50,000 in a situation in which their peers made $25,000, rather than a $100,000 in a context where $200,000 was typical.

The rationality there can be debated, but I bring it up because any argument you make to your boss needs to set up properly. Right now you are essentially saying: “My fellow administrator is incompetent — so you should give me a raise!” That is not persuasive.

If you believe you should make more money, you need to construct a case that’s tied to you, your abilities, your accomplishments and your worth. Energies devoted to tearing down your colleague are high-risk (you might come across as spiteful, or nuts) with no clear rewards (a co-worker’s faults say nothing about your merits).

In other words, don’t become so caught up in your “positional” concerns that you veer off into a mission that’s less about what you deserve, and more about some abstract pecking order. Ask yourself: Would you rather get a $6,000 raise (tied with your colleague, but making more money than you are currently) or stand pat and see your colleague’s salary reduced by $7,000 (you’d be Menckenesquely ahead, but not bring home a single extra dime). The answer should guide your actions.

If your real objective is to snag a higher salary, perhaps the lesson to take from your co-worker is that she, somehow, persuaded your bosses to give her more money. Maybe you should ask her for advice.

Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld for publication). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

The Workologist: The Clinging Co-Worker

Dear Workologist:

I work in my company’s I.T. area. We are expected to remember a lot of technical information, or know how to find whatever we can’t recall. I have a co-worker who can’t seem to analyze and resolve his own work. He asks the same questions repeatedly, even though 85 percent of our work is documented. By the end of a typical day, I’m exhausted not only from doing my work, but also from helping him with his. How do I encourage this needy co-worker to stand on his own? Pamela, Brooklyn

So often, issues with co-workers are most smartly resolved by channeling your inner diplomat, nudging your adversary into compliance without giving offense. Not this time. You don’t have to be a jerk about it, but you do need to be direct with your needy colleague. Pussyfooting around this problem is not only bad for you and your company — it’s also not doing him any favors.

You can do this by degrees, pushing back on each question with a polite but definitive variation on “I have a lot of work to do right now — you can look that up.”

Or you can use the next incident as an excuse for a serious sit-down: Just as you’ve done here, explain that you can’t do your job and his, and that he needs to get over the hand-holding and do his own work. Don’t make this sound like a threat, because that’s not the idea. You’re just having an honest conversation, peer to peer. The message is not that you won’t help him; it’s that you can’t.

The worst outcome is that if he keeps leaning on you, you’ll have to explain the situation to management. That would be painful, but no one is benefiting from the current situation. And the best outcome — it’s possible! — is that he does shape up.

•

Dear Workologist:

I work for a large city agency. I am considering applying for a position in a different unit. I have contemplated telling my supervisor about my intention to apply, in the interest of disclosure. But I’m not sure this is the best strategy. If I don’t tell her and I get an offer, then it seems that no harm has been done. If I tell her and I don’t get an offer, don’t I risk my future? She might be less likely to promote me or increase my responsibilities. Jean, Brooklyn

It’s almost never a good idea to tell your boss, in effect, that you’re thinking about quitting. And yet people do it all the time, and for one of two reasons. The first is that it’s a tactic for expressing dissatisfaction — the boss is supposed to panic at the idea of losing such a valuable employee, and respond with a promotion, a raise and access to the executive washroom. That’s often a false hope. Indeed, explicitly raising the notion of your departure can be a disastrous starting point for a negotiation. “I have a job offer” carries some weight; “I might be able to get some sort of job offer” does not.

Sometimes, employees tell the boss they’re thinking of quitting out of a mushy sense of obligation. But by and large, employers eliminate emotion from their thinking when they end their relationship with an employee. When they are considering whether to cut ties with their workers, they tend to keep that possibility to themselves. Layoffs are generally abrupt; any prelude to a dismissal is likely to come in the form of an ultimatum-style warning. Rarely do companies say: We’re kind of thinking of cutting your position, but who knows what’ll come of it?

The reverse should hold true for you. Unless your agency requires you to disclose that you are applying for a job in a different unit, you should keep that information to yourself. Telling your supervisor about your plans carries risk; keeping quiet does not.

•

Dear Workologist:

I’ve been an Apple fan/user for many years, and have been fortunate that my employers for the past decade-plus have provided me with Macs for my work. However, I recently started a job that requires me to use a PC. The last time I had to use a Windows-based computer was in the 1990s, so there’s been a steep learning curve that has created a greater drag than I anticipated. My efficacy and productivity are not what I would like. How do I explain this to my boss without looking as if I’m making excuses for my less-than-stellar performance?

B.C.A., Washington

Operating systems come and go, but making excuses without looking as if you’re making excuses is a skill that no technology will ever disrupt. This is an interesting iteration of that commonplace challenge, because it’s probably not obvious to your employer that there’s any learning curve at all. We’re not talking about mastery of some obscure, ultramodern software here. This is Windows, one of the most familiar technology tools in the history of technology tools.

Offer your excuses in overlapping layers of good intentions — what you’ve done and what you’re planning (or willing) to do. Try saying something like: “It’s been awhile since I’ve used Windows, and it’s changed just enough to keep me from being as productive as I usually am, so last night I started brushing up with an online tutorial. Are there other resources you’d suggest to help me get up to speed as quickly as possible?”

Should this inquiry yield a useful answer, great. But the point is that this is a pre-emptive strike: You’re indicating that you know there’s a problem, that you’re working to fix it, and that you would welcome — but don’t require — help.

Whatever you do, don’t wait for a manager to be the first to bring this up — or, perhaps even worse, for one of your colleagues to sit you down and tell you to stop being so needy.

Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld for publication). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

The Workologist: An Awkward Discovery at Work

Dear Workologist:

I recently received a call from a number I didn’t recognize. There was no message, so I Googled the number. One of the search results contained the name of a junior colleague — on what was evidently a site collecting “customer reviews” of escorts.

I have no desire to see this person’s career affected by private activities that don’t affect his work — but I certainly don’t want a client Googling around and finding the same thing. I think I have three options. I could tell him and see if he can clean it up, change his number, etc. (We’re not friends, and this would certainly be mortifying for all involved.) I could talk to his supervisor (with whom I am friendly). Or I could just pretend that I never found it and tell no one. That’s what I’ve done so far.

Matt, Brooklyn

Clearly, the easy path is the one you’re on — but it’s obviously bothering you, and I understand why. That said, you don’t have all the facts, and this whole scenario sounds bizarre. I’m certainly no expert on such sites, but the idea that someone would use his real name and phone in that context seems extremely unlikely. Maybe this guy is a victim of some kind of crossed wires. The Internet, after all, is thick with bad information.

Either way, the bigger issue is what to do when you stumble across embarrassing information about a colleague online. Start by asking what you’d want to happen if the situation were reversed: You’d want to know, right? But that doesn’t mean a confrontation: You could go to your colleague and simply ask if the number you have in your phone is his. Whatever the answer, you then can neutrally describe your experience: call from strange number; Web search; this guy’s name on a site where he might not want it to exist. End the conversation on a note that’s blunt about the stakes but that makes it clear that you’re trying to help, not get him in trouble or even establish whether what you found is true. “It’s crazy what ends up on the Web, and who knows how it gets there, but it might be a good idea to change your number so none of our clients, or anybody else, gets the wrong idea.”

You’ve given him the chance, and the extremely strong motivation, to take care of the problem immediately.

•

Dear Workologist:

I work for someone with “anger issues.” He constantly demeans employees who report to him, and some who do not. Recently he was very angry with me over a perceived slight — a paperwork misunderstanding — and told me off in front of a co-worker. Later, he came into my office and picked up where he had left off. I was sitting with my legs crossed, and at one point he demanded that I uncross my legs when speaking with him. When I next saw him, he acted as though nothing had happened.

Should I report this to the human resources department at my company? I could be opening a can of worms that might make it difficult to get another job.

Ed, Los Angeles

If you’ve daydreamed about writing a pilot for an HBO drama about a terrible workplace, your boss has given you solid-gold material with that leg-crossing thing. That’s the good news. The bad news is that if you haven’t been daydreaming about some other job, maybe you should, even perhaps somewhere else within the company.

With that in mind, the first step toward addressing this through official channels is to take advantage of your own uncertainty: have an informal conversation with someone in H.R. about ground rules for lodging a complaint. Don’t name names, but make the outline of the “hypothetical” problem clear.

If Mr. Anger Issues routinely comports himself in the manner you describe, it will not — or should not — be breaking news to H.R. One hopes that the department already has an eye on him, recognizing that a single toxic manager can set off a discontent contagion. That you value your position enough to proceed with caution suggests loyalty that your organization should value; if two or five or seven or more employees are reconsidering that loyalty in the wake of demeaning encounters with one individual — and wasting company time while obsessing about it — the math gets pretty easy.

But it’s possible that your H.R. department isn’t that clever. If the response is a rules-and-regulations wall of indifference, back off and consider your new choices. Stick with a company that’s more concerned with bureaucratic niceties than a functional workplace? Or focus on finding a new situation?

•

Dear Workologist:

My business is about helping inventors, makers and entrepreneurs share the stories of their innovations. After long days studying new products, my team proposed making one of our own. It’s a kegerator — a beer keg/mini-fridge hybrid. Kegerators are nearly de rigueur in many start-ups, and as C.E.O. of a young, hard-working team, I am loath to discourage any off-hours social activity or creative enterprise.

But in our company we have 10 interns, and some are underage. I spend my “off hours” with teenagers and young adults, as I have three sons — and that is enough parenting for me. Do you think I would be dodging such responsibilities at the office by blessing our Kegerator Krew?

Jules Pieri, Somerville, Mass.

You certainly have no responsibility to add parenting to your C.E.O. duties. But there is that pesky rule-of-law thing: A 20-year-old intern who flunks a breathalyzer shortly after a company-kegerated wind-down from a hard day’s work in your offices would definitely be your problem.

That doesn’t mean you can’t have an office kegerator. But while you are not your employees’ parent, you are also not their pal: you’re the boss. Laying out the dos and don’ts is your job. The good news is that being a parent is actually helpful: What rules would you expect your sons’ employers to have in place in a similar situation? The answer to that hypothetical is exactly what you should do.

Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld for publication). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.