Who’s Afraid of the Big Bad Boss? Nine Tips

July 29, 2014 - 4 minutes read


Bosses are inherently intimidating, even though most of them aren’t actually big, or bad.  Still, they are “the boss” and they have a great deal of control over your life, which can make them scary.

I met my first boss when I was eighteen. He seemed nice enough, but did expect a day’s work for a day’s pay.  I had a summer job as a stock boy in a warehouse, unpacking, stocking shelves, and filling orders.

About a month into the job, my family was leaving for an extended weekend vacation. Being so new I was afraid to ask my boss for time off, so on Friday afternoon I slipped out of the warehouse at 3:00 pm, two hours before quitting time.

Luckily, when I returned to work on Monday morning my boss was much kinder than I expected (or deserved). He did point out that “disappearing without notice” was not acceptable, but he later promoted me to running the billing machine when the regular operator left for vacation.

At age 27 I started my own law firm and have been “the boss” ever since.  But I still remember my initial fear about talking to the boss. If you share that fear I encourage you, for the sake of both your career and your company, to talk to your boss, especially if you’ve made a mistake.

As the boss I live in a bubble and seldom talk to any of our 3,000 tenants, our hundreds of suppliers, and even our seven hundred investors. So I need to receive important information and suggestions from my employees.

Several months ago, for example, two of my valued employees entered my office looking like death warmed over.  They had made a $137,000.00 mistake. I’m glad they found the courage to see me at once, because their mistake was growing by $4,000 per day, and we solved it the same afternoon.

If you find yourself in the difficult situation of having to break some bad news to your “big bad boss” here are some tips to make the experience less scary and more effective:

1.    Make a specific appointment for a five or ten minute meeting.  If I’m interested, it will be longer.

2.    Make the appointment for early in the day.  By 3:00 pm I’m tired and more likely to say “NO.”

3.    Tell me in advance what you want to talk about.  Make it as positive as you can.

4.    Suggest solutions.  By 9:00 am I have already heard about enough problems.

5.    Bring a one-page summary with you.  I can read faster than I can listen.  One week later I can read better than I can remember what you said.

6.    Thank me for my time.  We all like to be appreciated.

7.    You might practice your presentation in advance.  This will help you to be succinct.

8.    Be authentic.  People try to sell me something every day, and if I sense they are faking it I will cut them off without a second thought.  Or a second opportunity to see me.  When you are real we will connect.

9.    Remember that you are doing me a favor.  You are helping me to do my job better, and I want both you and our company to thrive.

My philosophy is that we’re all in this together.  As a boss, it’s my job to encourage my employees, to pay them fairly, and to steer clear of disasters.  It’s also my job to appreciate their candor, their courage, and their concern.



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