(issue 108, page 103)

This is my 35th and final “Corporate Shrink” column. Your questions over the past three years have touched on the widest range of issues: difficult bosses, dysfunctional teams, competitiveness, greed, sex, death, even (perhaps most controversial of all) the use of perfume in the workplace.

My brief answers couldn’t possibly have done justice to such complex matters. While I’d like to believe I’ve been helpful, each question would have been best addressed in a thoughtful conversation–the sort I worry is happening all too rarely in business today. So for my parting shot, I’d like to talk a bit about…conversations.

The ability to converse should be a basic building block of organizations. Healthy conversations allow leaders to lead, followers to respond, negotiators to make deals, salespeople to sell, and researchers to develop ideas. How many meetings have you attended, after all, where the first comment afterward was a judgment on the quality of the conversation? A “good meeting” usually means one in which people felt genuinely engaged, where they learned or accomplished something.

Yet large companies so often operate in ways that thwart good conversations. There are formal processes for everything, with well-intentioned manuals, training programs, hierarchies, and corporate jargon that mostly keep employees from really communicating. We typically assess a colleague’s work, for example, via online surveys, psychological tests, and language that strenuously shuns direct criticism. Anything to avoid taking a colleague aside and telling him what he’s doing wrong.

The best managers know that the discomfort involved in such honest conversation is well worth the resulting satisfaction. Even the well-intentioned, though, face hurdles. One is technology. I love my BlackBerry, but it is too often a substitute for talking. And the rate at which we gather and exchange information long ago outstripped our capacity to talk to each other about it, much less understand it all. At the same time, the explosion in executive coaching, while reflecting leaders’ hunger for conversations about emotionally meaningful topics, poses yet another danger: It brilliantly circumvents the stigma of seeking psychological help, yet it also risks entering emotional territory that should be explored by clinicians trained in the talking cure.

At their core, most of the letters you’ve sent me have concerned the same problem: how to talk with complicated, difficult colleagues. There’s no magic formula for that. But the surest path to a good conversation, I think, is to trust your own curiosity. If you’re having trouble connecting with someone, ask questions until you understand him. If what you’re hearing doesn’t make sense, keep talking until it does. When in doubt, step back, look the other person in the eye, and ask directly, “What just happened here?” Or, “What are we really talking about?”

On the other hand, the hardest part of any conversation is knowing when to keep our mouths shut. The more you know and learn about the other person as a human being, the better the conversation. And the more you can listen without passing reflexive moral judgment on what you’re hearing, or without prematurely going into action mode, the more meaningful the interaction will be.

Thanks for your support over these past three years. Stay curious about your work and never be satisfied by pat answers. The working world is filled with irrationality and emotionality. If you can accept and understand that–and acknowledge your own contributions, however human and imperfect–you and those around you should be happier and more effective. A good conversation is the best place to start.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

As high and fast as I’ve made it up the corporate ladder, I dread going to work. I’m two levels below the CEO, and my immediate boss can’t stand me. Even though she’d never admit it, I can tell she’s envious of my relationships with clients and colleagues. What should I do? (issue 107, page 109)

If it’s any consolation, your situation is not so uncommon. Envy is rarely discussed in corporate circles, but it arises wherever there’s competition and hierarchy – basically, everywhere – and can cause untold misery.

First, a warning: Whenever I hear someone say her boss envies her, I wonder whether there’s some projection going on. Could it be that you’re actually jealous of your boss’s power and success?

But your boss’s envy may well be real; I certainly see it in my consulting work all the time. In the same way that parents can be jealous of their children (think of the dad who envies his son’s athletic prowess), bosses can wish they had some of their subordinates’ talent or energy. That can lead them to act destructively. Even if your boss won’t cop to this motivation, it’s hard to camouflage such powerful emotions.

Be sensitive to your boss’s envy, and don’t rub her nose in your accomplishments, which will only make matters worse. Try bringing her into your network and sharing some contacts. Your success and hers don’t have to be a zero-sum game.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

I am one of several independent contractors who do long-term consulting for a company. I’m a very competitive person, and when our contracts come up for renewal, I tend to do whatever it takes to win–but that bites me in the backside when the other consultants see me as a threat. What is your advice? (issue 106, page 105)

As a consultant myself, I can relate to the pressure you feel to sell extensions of your engagements. This doesn’t present a conflict when a client genuinely needs your services, as they often do. On the other hand, there are situations in which the company really should be able to handle your role internally. If that’s the case, you should let the weaning begin.

I admire your competitiveness, but if you truly do “whatever it takes to win,” there’s good reason for rivals to look askance. It’s one thing to assertively pitch a client to renew your contract and another to actively muscle other contractors out of the way. If you’re doing the latter, I can’t blame them for trying to block your path. Sell yourself on your merits rather than by tearing down or interfering with your competitors. There might be room for everybody–and even if there isn’t, dialing down your competitiveness could help preserve your reputation and relationships.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

I’ve been working with my boss for 14 years, and sleeping with him for 7. Recently he stopped wanting sex, although he still wants to see me. I know he’s involved with two younger women who don’t work in the office. I like my job and he pays me well, but being exposed to his personal activities is disturbing. Should I quit my job and leave town? (issue 105, page 99)

That’s like asking if you should tidy up your room on the Titanic before it sinks. A better question is this: Why did you get and stay involved with your boss in the first place? Don’t assume you know the answer. It’s a complex question – possibly with deep psychological underpinnings – that deserves thorough exploration. I’m concerned about your potential for self-sacrificing, even self-destructive, behavior and your apparent lack of self-awareness about it.

Granted, you were both willing participants, but as the boss, this guy clearly had the upper hand in the relationship. He sounds exploitative, and he doesn’t seem to have much compunction about letting you in on his other affairs.

Severing your ties to him now is only the beginning. I’d recommend that you get yourself to a good psychotherapist who can talk you out of this mess, then guide you to an understanding of what led you into it in the first place. Leaving your job sounds inevitable, although skipping town may only prove a doomed attempt to meet an emotional problem with a geographic solution. Gaining some insight might help you move on without having to move away.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

We’re in a conundrum that so many early-stage companies face: No one will invest unless we have customers, but customers want to see that we have enough resources. This catch-22 has been going on for a year; we’ve even attempted to offer customers stock–to no avail. How do we communicate confidence in our venture? (issue 104, page 108)

Well, nothing breeds success like success – but that doesn’t exactly help, eh? Assuming you have a good product or service to sell – you do, right? – then it’s time to reevaluate your pitch in the cold, hard light of day.

First, consider the possibility that you’re sending mixed messages. Your questions suggest that your management team itself might lack confidence in the soundness of the venture. If so, that’s something you could be transmitting inadvertently to customers. Authenticity is hard to fake. Perhaps you need to fix something about your offering before you can make it sound more compelling.

Alternatively, you could be coming on too strong. That’s perfectly understandable; it can be a way of overcompensating for the very real uncertainty that surrounds an early-stage company. But if you aren’t acknowledging even a modicum of doubt, then potential buyers might sense an attempt to cover something up.

Worse yet, your team’s neediness could be fueling a vicious circle of fear and desperation. Customers and investors pick up subliminally on your edgy cues and back off–which sparks even greater internal panic. Stop the cycle before it wreaks more damage: Take a step back, see if any of these symptoms resonate, and take the necessary medicine.

My boss and I used to be on the same floor, allowing us to work very closely and bounce ideas off each other every day. He was promoted and moved to a new building five miles away. I got his old job, but I’m now his only direct report not located in his building. How do I maintain our relationship?

Congrats on your promotion! Now you need to come to terms with the prospect of getting by on your own. I suspect that’s part of the package. Yours isn’t an uncommon problem. You thrived in your previous working relationship, but your promotion means taking on more responsibility and mentoring subordinates the way your boss did you. Remember, it’s not the five miles that matter: Your role in the organization is more important than physical proximity in determining your level of interaction. And while his other direct reports may run into him more often, you have the benefit of greater independence.

Here’s the important psychological point: Success, in this case promotion, frequently brings with it some sort of loss–of secure relationships and of comfortable work demands. The sooner you reconcile the loss of the old, the more you’ll flourish in the new.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

I’m worried about keeping up with all of the advances in technology and the effects of globalization. Should I be? (issue 103, page 140)

Yes, no, and maybe. There’s no question that we live in a rapidly changing world without the predictability that midcareer executives from prior generations enjoyed. But you can control something: yourself and your personality. So I’m hedging my answer.

First, the yes. You should worry in the sense that it pays to put in the effort to follow as closely as you can what’s happening around you. I’m convinced that in the future, the most successful among us will be those who understand that they are citizens of the world. Keeping up with the effects of globalization takes both openness and work–openness to learning, reading, and seeing the world, and work to adapt to the competitive, intellectual, and cultural shifts before they bite you in the rear.

Now, the no. If you’re an engaged manager or leader, the technology will find you. What interests me is how the pace of technological development has long outstripped our human capacity to use that technology, including our brains’ ability to process information and to do actual work. That’s why we’re so overwhelmed by those hundreds of emails on our handhelds. Being realistic and discriminatory about which new technology to employ may be a more important skill than embracing it all.

Finally, the maybe. By the time we’re midcareer, our personalities are largely set. The biggest variable in all this change is you, especially your personal flexibility and your open-mindedness to listening and learning. These qualities are hard to teach and even harder to acquire as we age. But for an ambitious, driven executive, they’ll make or break your career. I’ll go even further: With rapid globalization and technological innovation, the more you can tolerate or even enjoy ambiguity, uncertainty, and change, the more successful you’ll be.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

I’m new to cold-calling at a financial-services firm. From a psychological perspective, what’s the most effective etiquette for a successful cold call? (issue 102, page 104)

If one size really fit all, then cold-calling would be easy. But it’s not enough just to be polite. The best etiquette strategy is one that adjusts on the fly, based on careful listening and empathizing with the other person.

You know, as I do, what the alternative sounds like. The cold-call recipient feels like he’s talking to a dispassionate automaton replaying a script (which he often is). So what to do? Pay attention. If the person you’re pitching sounds rushed, acknowledge that and cut to the chase. Otherwise, you’ll come across as clingy and annoy your potential customer. If your target seems more formal, address him or her by Mr. or Ms. (There’s no quicker way for a telephone rep to turn me off than by addressing me as if we’re old buddies.) Most of all, try not to take it too personally when your cold call gets the cold shoulder. It comes with the territory.

I’m finishing my MBA but struggling financially until I get my first job. I have aging parents and an unsatisfying personal life. I’ve tried to solve my problems by applying for jobs, but I still feel terribly isolated. Any advice on how I can cope with this?

If it’s any consolation, you’re not alone. Lots of people experience feelings of isolation at different times, and it can be painful. This is clearly a tough time, filled with uncertainty about your future, torn between feelings of responsibility for your parents, and your commitment to improve your own life. And not having someone to share your voyage with makes it all the more difficult.

Time and perseverance will undoubtedly help on the work front, but ultimately that may be the easy part. Caring for elderly parent–and dealing with your guilt if and when you choose not to–is more complicated. Consider the possibility that unresolved anger from childhood might interfere with your freedom to be responsive to their needs now. And given all that’s on your plate, it might help if someone else, like a sibling, could look after your parents until you’re on more solid ground.

Your unsatisfying personal life might be the most complex part of all. There’s no rational reason why you should be alone. But we know that being successful, or even being highly responsible, doesn’t guarantee intimacy. For some, it comes effortlessly. For others, emotional blocks can make intimacy feel unattainable or dangerous.

Although these issues probably aren’t helping matters, don’t assume that they’re the cause of your unhappiness. It may be that your inner emotional life will improve once your external circumstances stabilize. But if you still feel isolated, you might benefit from speaking with a qualified psychotherapist who can help you figure out why you haven’t found a partner to help you through life’s rough patches.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

Our charismatic and talented CEO, whom we all thought would lead us well into our uncertain future, just announced he’s resigning to work for the competition. How do we cope? (issue 101, page 107)

When a beloved CEO leaves precipitously, he bursts the shared illusion that you’ll have him forever. We tend to idealize good leaders, blinding us to the fact that they’re in it not only for us but for themselves, too. When he quits to take a bigger job, your initial (and understandable) shock gives way to a mix of betrayal, anger, sadness, loss, uncertainty, and disorientation. You might be surprised, though, by how quickly these feelings pass.

Think of this as a chance to take a hard look at your organization, including your own role in it. Ask yourself what problems and opportunities may have been concealed by your idealization of the CEO.

Undoubtedly, there will be speculation about why he left, which can take the form of collective self-doubt. Was it solely to further his own career, or did he know something you didn’t? Presumably there will be an interim boss in place while the company searches for a new one. Both the temporary CEO and the successor should pay close attention to the aftereffects, traumatic or not, of the former boss’s exit. That said, no one, not even the top dog, is indispensable, and most organizations are more resilient than their employees think. Some do even better under new leadership.

The bottom line? Pay attention to your feelings and don’t sweep them under the rug. Make sure you don’t turn your anger at the old CEO against others in the company. In the end, you’ll come to remember that being a CEO is just a job. He was your boss, not your daddy.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).

I’m the sole woman on a five-person sales team. We get along very well, but the guys occasionally go to a strip club. They invite me along, but of course I always decline. Is there anything else I should do? (issue 100, page 105)

Men! Well, asking them to consider after-hours activities that are a bit more inclusive wouldn’t be a bad start. If their G-string galas offend you, it’s certainly your prerogative to speak up. If their behavior doesn’t bother you, and you’re comfortable being part of what sounds like an effective team, I’d leave well enough alone. But if you’re feeling left out of essential conversations, or if you think they view you in the same shallow way as they do strippers, then you and the guys should have a good heart-to-heart.

If you go this route, be careful how you put it. The success of your team depends in part on the soundness of your interpersonal connections. Explain that you’re not passing judgment on your colleagues’ right to visit these establishments–but that it makes you uncomfortable being invited to something they know you’ll turn down.

Of course, that raises the question of why they’re inviting you in the first place. My bet is that your male colleagues treat you like one of the guys most of the time, but on their nights out they’re trying to get a rise out of you. Also, some men patronize strip clubs as a way of dealing with their anxiety about intimate relationships, including with each other. If you really want to shake up the guys, you might lay out the theory that they’re inviting you to cut the latent homosexual tension between them. Or better yet, insist that on their next night out you all go see male strippers.

Dr. Kerry J. Sulkowicz, a psychiatrist, psychoanalyst, and founder of The Boswell Group LLC, advises executives on leadership, management, and governance. Send him your questions about the psychology of business (shrink@fastcompany.com).