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.

On-the-Job Blunders

A friend called me last week in a panic. “I screwed up big at work and I think I could get fired over this.” I listened to the situation. Yes, she might have missed some protocols in carrying out a project (an expensive project) but no, she wasn’t going to get fired. I helped her strategize.


1) Be calm. Walk around the block and lose your mind for a minute. But as soon as you’re back inside and dealing with the situation, you need to be calm.

2) Take ownership. If it’s your blunder, own it. Use simple language. “This was my error.” Even if it’s not yours alone (it never really is when you’re working on a team) don’t blame others. Throwing a colleague under the bus will reflect most poorly on you.

3) Determine the root cause. This is tech-speak for figuring out why it happened. If it’s a one-off mistake on your part, say so. But if it’s a procedural issue and is likely to happen again, figure out why it happened and change the methodology. Again, this is not about blame, but about improving overall business practices.