Tips for working through issues with your boss

It’s a common question: “How do I get my boss to change his behavior?”  Tied up in that question are all the anxieties about how the boss will respond and fear that the messenger will be shot. As a result, many employees say nothing, letting the negatives pile high until they just can’t take any more and then they explode, and their worst fears come true.


Here are some common mistakes I’ve seen and what to do instead:


Going around the boss to his or her manager, before talking with the boss directly, first. (This goes for talking to Human Resources, too.)


While it’s easy to see why you might want to avoid a confrontation, it almost always escalates the problem if you involve outsiders. The original issue becomes secondary to the anger your boss will feel for being exposed to HR and his or her manager.


If you don’t at least try to raise your concerns with your manager, you will look as though you are na├»ve and unprofessional by not giving your boss a chance to solve the problems first. You don’t want to look like a tattler, who won’t take responsibility for doing whatever you can to resolve the issue.


Even if you think your boss will react poorly, it’s still an important first step to have the conversation. If you do take the issue to HR or to his or her boss, you will be able to say you did what you could.


What to do: Schedule some time with your boss, to meet face to face. But wait until you are fully prepared to discuss the matter, because if he or she says, “I have time now and I insist that you tell me what this is about,” you’ll be ready.


Speaking to your manager when you are angry or hurt.


This is a really bad idea for all the obvious reasons. By the time the dust settles, things are said that stick long after the issue has died away. It’s much better to rant at the cat or your significant other until you can look at the issue with a more objective perspective. I recommend at least one day, maybe two or more, depending on how worked up you are.


What to do: Write down the behavior and how it affects your work or makes you feel. Put it away. Take it out a day later and isolate the key message you want your boss to understand. Share it with someone who is objective to make sure it does not sound blaming or judgmental.


Saving up wrongs until you can’t take any more and then letting the boss have it.


Anyone who has been on the receiving end of someone with bulging eyes who is hurling a long list of saved up hurts, knows why this is doomed.  “And another thing…and another thing…” may feel good to the person who is venting his or her frustrations but it feels overwhelming and unfair to the person under attack. It is bound to get a defensive response.


What to do: Start with something that is more easily fixed. Once you make progress on that and there is a foundation of progress and no ruffled feathers, you will feel safer moving on to the next issue. Also, be willing to help fix it any way you can. For example, “Would it help if I took the lead and gathered agenda items for you? That could help our meetings be more focused.”


Threatening to quit in a fit of rage or trying to call his or her bluff.


In an angry exchange, you may be tempted to take your ball and go home, since it’s the only real power play you have as an employee. In the heat of the moment, your boss may just take you up on it—even if he or she doesn’t really mean to but it will be too late to take back. And if you really don’t have a job to run to, it could be a foolish threat you will regret.


What to do: If emotions are getting out of control, stop the meeting by saying, “This is unproductive for both of us. Let’s forget it until we’ve cooled off,” then walk away.


Blaming every problem on the boss, without taking any ownership for your part in the process.


Face it. It does take two to tango. Rarely have I seen a boss/employee conflict where the employee doesn’t play at least some role in problem.


Talk with an objective colleague or friend and ask the person to play devil’s advocate with you and take your boss’s perspective. You may uncover how you are adding fuel to the fire.


What to do: When you approach your manager, use I statements, rather than you statements. For instance, “I know you’re busy, but when my proposals sit in your office for long periods of time without a response, it’s not only frustrating to all the people on my committee who worked on it, it makes me look ineffective. Is there something I can do to help you expedite the process?”


Talking negatively about your boss to other people in the organization.


If you are this frustrated you have let your emotions spill out of the box, and it will splash on you. Unfortunately, bad mouthing your boss will also leave a toxic trail back to you. It inevitably will be mentioned to your boss and –no matter how guilty your boss is—end up looking like you are part of the problem. Why? Because people will think you are politically ignorant about the main rules of organizational behavior. They will distance themselves from you because, like a rabid skunk, you are acting in an unpredictable way and they don’t want to be near someone who could spray them.


What to do: Follow the steps above so that you are perceived as objective and professional. That way, the only issue on the table is your boss’s behavior, not how you mishandled the situation.

Joan Lloyd is a Milwaukee based executive coach and organizational & leadership development strategist. She is known for her ability to help leaders and their teams achieve measurable, lasting improvements. Joan Lloyd & Associates, specializes in leadership development, organizational change and teambuilding, providing: executive coaching, CEO coaching & leader team coaching, 360-degree feedback processes, retreat facilitation and presentation skill coaching and small group labs. Contact Joan Lloyd & Associates at (414) 573-1616,, or 
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