Never Car Pool With Your Boss—

And Other Lessons Learned From 40 Years in the Workplace

Part 1

Zig Ziglar said: “You will get all you want in life if you help enough other people get what they want.” I’ve often thought that my purpose in life is just that: to help others achieve their goals and dreams, thereby achieving mine. This series of blog posts on lessons learned from 40 years in the workplace is my gift to those just starting their careers, stuck somewhere in the middle, or reinventing themselves in second and third careers. Enjoy the posts, use what you can, regift or toss out those lessons that you don’t think apply to you. The lessons are in no particular order of priority. Here’s part 1:

Never car pool with your boss

This is another way of saying don’t get too “intimate” with the person who approves your work or leads your team. Early in my career I car pooled with my boss and two colleagues. It was a disaster, although it led to many amusing, almost unbelievable stories, plus content for a retirement roast. My boss was personable and seemed knowledgeable in his field; we liked and respected him, which led to the car-pool decision. What could be wrong with riding to work together and having additional opportunities to discuss business while sitting in traffic? A lot, it turned out.

We found out things we really didn’t want to know about the boss. For example, most mornings he barely made it halfway down the driveway before his wife came out onto the porch in her bathrobe yelling, “did you take your pills?” or “you forgot to take out the garbage.” After dealing with whatever issue she brought up, he got into the car, bringing with him the strong scent of recently fried bacon. My colleague’s theory was that the boss’ wife used his suit coat as a splatter shield. Weather extremes were a trial. He refused to fix a $10 item that would have heated the car during the winter, and rolled down the windows during Baltimore summers rather than run the air conditioning. We even had to plead with him to leave earlier on mornings we were facilitating training sessions. He became a laughing stock rather than a respected leader, and, one by one, each of us came up with a flimsy excuse to exit the car pool.

It was like being in a long marriage, where every little quirk begins to annoy the other party to the nth degree, yet with none of the benefits of marriage (other than a continuing paycheck). We simply knew more than we wanted or needed to know about our leader’s idiosyncrasies. What I learned was: be friendly, helpful, professional with your boss. Discover enough about him or her to understand where the leader is “coming from” and draw the line there. I’m sure I’ll hear from people who married the boss and lived happily ever after, but my experience tells me they’re the exceptions.

Cultivate relationships

This may seem to contradict lesson #1 but you don’t have to be best friends with someone to make their day. If you go the extra mile to offer congratulations, sympathy, best wishes on birthdays and other special days, your colleagues will more likely remember you and help you be successful. Moving up the scale of difficulty, be happy for your colleagues even when they get an opportunity you wanted. Love people even if you don’t always like their behavior. And do all these things with no expectation of returned favors. I’m not suggesting you go for sainthood or doormat status, just take the high road when others take the low. You might be surprised by how many people actually will love you back.

One of my bosses (not the carpool man) was someone I had known since age 3. We worked for the same company for years and developed a great professional respect for each other. Toward the end of my tenure with this company, I had a chance to be promoted, I thought, and then all of a sudden they moved him into the position I wanted, and he was now my boss. Both of us were a bit uncomfortable with the new situation, so we talked openly about how we felt and agreed on how we wanted to move forward. After that, we went on with our work and enjoyed being part of a team that was making a difference. We never had a problem with each other, and he later became—and is still—one of my clients. The trusting relationship we had cultivated over many years helped us get through a rough patch.

A few years ago Linda Kaplan Thaler and Robin Koval wrote The Power of Nice, in which they described how their business became one of the country’s fastest growing ad agencies by being “nice” to people. I remember thinking, finally, someone has acknowledged how powerful it can be to build warm long-term relationships instead of burning bridges on your way to success.


Lessons Learned Part II coming soon.