Many people believe that their relationship with their boss — and possibly with any boss they’ll ever have — is going to be strained at best and contentious or dysfunctional at worst. Maybe they have narrow preconceptions (in-laws: all bad; bosses: all bad). Or perhaps they’ve had some horrible bosses and assume that’s simply the way the world works.
But it’s also possible that they’re responsible for at least part of what’s going wrong in the employee/boss equation. They may be new to the workforce and a little naïve or immature. Or they might be longtime employees who’ve fallen into patterns that have worn thin with their boss. If you know someone who has developed a few career-threatening habits, maybe this list will help them gain some self-awareness. I have seen every one of these behaviors over the years. I bet you have, too.
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1: Tell your boss what you think he/she wants to hear
This is an understandable human tendency, and it’s certainly not confined to the employee/boss relationship. Playing spin doctor may be socially expedient in some situations, an act of kindness in others. But in a working environment, you’re not doing your boss any favors if you hold back on what’s really going on. Any halfway astute boss is going to see right through you and perhaps resent you because you lacked the fortitude to deliver bad news or expected him or her to shoot the messenger.
2: Complain incessantly
I don’t know anyone who doesn’t complain at least some of the time — and often with justification. It’s okay to point out concerns and express dissatisfaction or frustration (or even weary resignation) from time to time, especially among peers. It’s how we cope. But constantly whining or carping about how this or that person or policy or situation is making you suffer is likely to drive your coworkers crazy. And bringing those grievances to your boss is going to do three things, all of them bad: Get on your boss’s nerves; convey the impression that you’re incapable of addressing problems in a constructive way; desensitize your boss to anything you say, even when it’s valid.
3: Cast your co-workers in a bad light
Some people go through life attempting to elevate themselves by denigrating the people around them. Even in a relaxed and harmonious workplace, those folks will probably surface and create discord occasionally. In a highly competitive or stressful environment, that kind of poison can turn an office into a snakepit. No (sane) boss wants either scenario. Your boss needs honest, actionable intelligence about staff, vendors, stakeholders, projects, and relationships — not sniping character assassinations calculated for personal advancement.
4: Suck up
I know there are bosses out there who actually DO want their staff to suck up to them, offering false compliments and exhibiting fake interest and concern in their affairs. If that’s your boss, and you have the stomach to play that game, more power to you. But for bosses who aren’t swayed by all that hooey, sucking up is only going to insult them or piss them off.
5: Pretend to be on board with your assignments…
… and then tell everyone who will listen how stupid or unfair or unrealistic they are. Obviously, you don’t want to be sullen or argumentative when your boss explains a task or project for you to take on. Nor do you want to whine to your boss indiscriminately (item #2). But it’s okay to be honest and push back when you see legitimate problems with a particular job. Air your concerns at the outset and work toward a compromise or concession, if you feel that’s warranted. Don’t just smile and nod and slink off to your cube to marinate in unexpressed ire.
Another version of this problem involves accepting an assignment with a full understanding of how you’re supposed to handle it — and then doing whatever the hell you want. This may be a willful response — an arrogant assurance that you know how things should be done, you do not intend to follow stupid instructions, and you know more than your boss about the requirements, the client, and the technology. Or it may be that you don’t have the experience or resources to do it the way you were told, so you try to wing it. Neither approach works. In the first case, you’ll appear insubordinate and untrustworthy. In the second, you’ll appear inept.
This one goes a bit beyond putting a positive spin on a bad situation or telling bosses what they want to hear. We’re talking about flat-out lying — presenting false data, denying mistakes you’ve made, fabricating reasons for absences, and making excuses for late projects. Your boss is almost certainly going to see through you and — just like the moral of a 1950s sitcom — your problems will much larger than they would have been had you been honest in the first place.
7: Don’t meet your commitments
If you can’t be counted on to do what you say you’ll do, you’re going to create a huge amount of extra work for your boss. Not showing up for meetings, not completing tasks, promising solutions that don’t happen, leaving work half done, ignoring client needs — your boss is going to have to follow along behind you to try to keep you on track, clean up the mess, and do damage control.
8: Go to your boss’s boss to discuss your concerns
Chain of command varies drastically from one organization to the next, so it’s tough to generalize here. But even if you work for One Big Happy Family, it’s a good idea to resolve issues at the local level, if possible. Let your boss decide whether and how to escalate matters. Going over your boss’s head shows a lack of faith in his or her abilities, knowledge, judgment, and influence. Of course, if the problem IS your boss, you may have to do an end run to get help with a bad situation. But when that’s not the case, it’s more efficient, honest, and respectful to approach your boss first.
9: Ask your boss to affirm every small action or decision you make
If you’re just starting out in a position, you’ll naturally need a little handholding. Best case, your peers will help you out and show you the ropes. And your boss — at least a good boss — should be available to answer your questions and provide direction. But once you know your job, leave the nest already. Cultivate an effective level of independence. If you can’t move forward on anything without asking your boss to green-light your actions, you’re quickly going to become a liability. I’m not suggesting you become a loose cannon (item #5), arrogant and immune to advice and guidance. But if you’re good at your job, you shouldn’t need constant validation or reassurance.
10: Badger your boss for special treatment
Call it a disproportionate sense of entitlement, a childish need for recognition, an egocentric conviction that your needs come first — the many flavors of the hopelessly self-important. If you’re constantly asking or expecting your boss to make exceptions or confer special favors, you’re being a pain in the ass.