Confronting the Boss

A friend asked me the other day, “Have you ever had to confront your boss?”

I laughed. “Yes, pretty much in every job I’ve ever had.” 

I’ve never been afraid to go head-to-head with the boss. Most of the time this just means bringing unknown issues into better view so they can be quickly problem-solved. Sometimes it means a difficult negotiation.

Either way, talking to the boss should never be viewed as a risk to your job security as long as your approach is reasonable and respectful, as long as you "play nice."

In my friend’s case, she wasn’t getting enough hours at her job and was at risk of losing benefits—a scary proposition for a single mother of four.

I listened to her situation. It all came down to better communication. No problem. She was in great standing with the company, with an excellent performance record. But actually, there was a problem. She was angry and was at risk of bringing that anger into the conversation.

First, she felt like she shouldn’t have to ask her boss to give her what she viewed as her basic right as an employee—40 hours a week. "I shouldn't have to beg for it," she said. Second, she felt her livelihood was being threatened, a fear that can evoke strong reactions in the best of times.

Here’s some of the advice I gave her and have given other friends in similar situations.

1. Be professional and impersonal

I advised my friend to deal only with the facts of the situation. She needed to ask her boss what they could do to ensure 40 hours per week. You can’t assume that your boss always has your best interest at heart. Sometimes—most of the time—you have to fight for yourself. Do this by speaking in terms of what’s good for you and the company.

Be impersonal. It's inappropriate to step in the door with the line, “Baby needs a new pair of shoes.” It’s understood that most of us have dependents, bills, and challenging financial demands. It’s understood that we all need health care coverage. So don’t blanket the facts with personal worries or unchecked anger that can make the conversation more emotionally charged than it needs to be. Assume that your needs are universal. Assume that your needs deserve to be met.

2. Strive for solutions

Once the problem is clarified, move quickly toward your statement of intent. “I want to find a solution.”

Whether you’re having an issue with team performance, communication, salary or job environment, be ready to find a quick solution that will benefit everyone. It’s important not to dwell too long in the things that are not going right. Of course, it’s a relief to finally speak your mind. But don’t indulge, unload or gripe.

Walk through the door with some creative solutions. Be ready to forgive and forget. Your boss doesn’t like a complainer and doesn’t want to sit through a therapy session with you. (Believe me, I’ve made these mistakes. Argggh.) Just try a simple statement, “What can we do to improve?’

3. Know your professional boundaries

Your boss is neither your friend nor your enemy. Your boss is someone who shows up to work with the ambition of doing well, meeting goals and keeping his or her job. When negotiating difficult situations, it’s important to remember that your boss, at all costs, is protecting his own sense of well-being. Sometimes your boss has it right, and sometimes not.

During college, I was waiting tables at a small, family-owned restaurant. The owner habitually asked her waitstaff to bring a few bags of coffee to her house whenever she ran out. These requests came more frequently as she began divorce proceedings with her husband. In short, she was barely keeping it together and began to rely on her employees as her personal support structure.

Although the owner’s house was only 5 minutes away, my co-workers complained bitterly about the errand. As I didn’t believe in silent suffering, I boasted that I would deny the boss’s request. One night near closing time, I got the phone call that forced my hand. The owner ran through her nightly check-in and then said, “Oh, and by the way, have one of the girls bring over some coffee for me. I’m out again.”

“I would be happy,” I said quickly, “to hand the phone over if you’d like to ask someone this personal favor.”  I listed off the names of the other gals who were working that night. "You could ask Jennifer, or Sally. Robin is here too." There was stony silence on the other end before my boss hung up.

I was applauded that night, but the gals were careful not to reveal themselves as my ally. The boss stormed around in a crying tirade for three days and on the fourth day called me into her office. She lectured me about “being a team player.” 

I was unrepentant. “It’s not about team work. You’re asking for personal favors. Your employees are afraid if they don’t do what you ask, they’ll get fired.”

I wasn’t worried about getting fired because I knew I was right. And so did she. I kept my job and there were no more requests for coffee.

I’d like to say that these sorts of misuses of power only happen in small business, but unfortunately not. One of my friends, an administrative assistant at a very prominent corporation, has been asked to go gift shopping, pick up dry cleaning and yes, even dog sit for her boss. Unfortunately, against her own good judgment, she has done all of this—partly because she was grateful to have a job in this economy and partly, because she was  under the mistaken impression that her boss was her friend.

Not so. Her job is now being threatened and her boss, for whom she’s done so many personal favors (on and off the clock), is not standing by her side. In fact, because professional lines were blurred, the relationship has deteriorated into an embarrassment for both of them. 

When it's revealed that you're doing something outside your defined job responsibilities, you've only yourself to blame. You will always be held accountable for actions that are not in the best interest of the company.

So remember to always establish and maintain clear boundaries with your boss. You can have warm, personable relationships. But don't get chummy. Avoid half-drunken heart-to-hearts at Friday Happy Hours. Avoid invitations to Saturday afternoon sailing trips or evening cocktail parties.

Because when push comes to shove, you have to rely on a professional code of ethics. No amount of warm fuzzies felt during Happy Hour will help you out when your job's at stake. Sticking to this code at all times will help ensure that you maintain mutual respect, and also help you keep your legs underneath you even in the worst-case-scenario.

4. Use resources as necessary

If you’re in a very tricky situation, be smart about using your resources. The rule of thumb is to respect the hierarchy. Try first to speak with your boss. If this fails, you might have an informal meeting with HR. If it comes to it, you might need to make a formal case with HR’s help, at which time your boss’s boss will be looped in.

In my case, after failing to make headway with my boss directly, I went to HR. Luckily, my HR person had an impeccable sense of integrity. She negotiated the issues with an objective, yet empathetic perspective and escalated the situation as was appropriate for my interests, and company's best practices. I was grateful to have her as such a trustworthy resource.

NOTE: Remember to be very careful not to blab to other colleagues. This is perhaps the most difficult thing to do. But it’s imperative. If you have a true confidante who’s working at your level, then you might want to share the situation and get their feedback. But don’t talk trash about your boss at the water cooler. It will bite you in the ass.

So while "confrontation" is often perceived as a dirty word, I like to think of it as opportunity. Nobody's a mind-reader and nothing is truly self-evident. You have to speak up in order to get what you need. An earnest one-on-one with the boss will not only pay off, it'll keep the paychecks coming.